EP3655402A1 - Substituted 3-heteroaryloxy-1h-pyrazoles and salts thereof and their use as herbicidal active substances - Google Patents

Substituted 3-heteroaryloxy-1h-pyrazoles and salts thereof and their use as herbicidal active substances

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Publication number
EP3655402A1
EP3655402A1 EP18737304.8A EP18737304A EP3655402A1 EP 3655402 A1 EP3655402 A1 EP 3655402A1 EP 18737304 A EP18737304 A EP 18737304A EP 3655402 A1 EP3655402 A1 EP 3655402A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
methyl
alkoxy
nmr
pyrimidin
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Withdrawn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
EP18737304.8A
Other languages
German (de)
French (fr)
Inventor
Michael Charles MCLEOD
Jörg Tiebes
Ralf Braun
Roland Andree
Ling Ma
Hansjörg Dietrich
Anu Bheemaiah MACHETTIRA
Elmar Gatzweiler
Christopher Hugh Rosinger
Dirk Schmutzler
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 AG
Bayer CropScience AG
Original Assignee
Bayer AG
Bayer CropScience AG
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Publication date
Application filed by Bayer AG, Bayer CropScience AG filed Critical Bayer AG
Publication of EP3655402A1 publication Critical patent/EP3655402A1/en
Withdrawn legal-status Critical Current

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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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-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
    • A01N43/72—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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • C07D403/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
    • Y02P60/20—Reduction of greenhouse gas [GHG] emissions in agriculture, e.g. CO2
    • Y02P60/21—Dinitrogen oxide [N2O], e.g. using aquaponics, hydroponics or efficiency measures

Definitions

  • the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
  • this invention relates to substituted 3-heteroaryloxy-lH-pyrazoles and their salts
  • Some of the known active compounds can not be produced economically on the industrial scale because of difficultly accessible precursors and reagents or have only insufficient chemical stabilities. For other active ingredients the effect depends too much on environmental conditions, such as weather and soil conditions.
  • heteroaryloxypyrazoles which are specifically substituted in the 1-position of the pyrazole with carbamoyl and claimed as herbicides.
  • Heteroaryloxypyrazoles named in the 1-position of the pyrazole specifically with alkynyl radicals are substituted and claimed as nitrification inhibitors.
  • WO2003 / 144309 Heteroaryloxypyrazole be named, which are specifically substituted in the 4-position of the pyrazole with aminopyridines or aminopyrimidines and claimed as protein kinase inhibitors with pharmaceutical benefits.
  • JP2000 / 095778 Heteroaryloxypyrazole be named, which are specifically substituted in the 4-position of the pyrazole with imidazoles and 1, 2,4-triazoles and claimed as fungicides.
  • substituted 3-heteroaryloxy-lH-pyrazoles or their salts are particularly suitable as herbicidal active ingredients.
  • the present invention thus provides substituted 3-heteroaryloxy-lH-pyrazoles of the general formula (I) or salts thereof
  • A is oxygen, -S (O) "-, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond
  • n 0, 1 or 2
  • Q 1 represents an optionally substituted aryl, heteroaryl, (C 3 -C 10) -cycloalkyl or (C 3 -C 10) -
  • the radical Q 1 is not imidazole or 1, 2,4-triazole, is an optionally substituted heteroaryl, each ring optionally having up to 4 substituents from the group R 7 is substituted hydrogen, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (Ci-C 8) cyanoalkyl, (Ci-C8) hydroxyalkyl, (Ci-C 6) alkoxy - (Ci-C 6 ) -alkyl, (Ci-C 6 ) -haloalkoxy- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkylthio (Ci-C 6 ) - alkyl, (Ci-C6 ) -Alkylsulfmyl- (Ci-C 6) alkyl, (Ci-C 6) alkylsulfonyl (Ci-C
  • R 1 and R 2 together form an alkyl (CH 2 ) m ring where m is 3, 4 or 5,
  • R 3 and R 4 independently of one another represent hydrogen, hydroxyl, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy (Ci-C 6) alkyl, (Ci-C8) alkylthio (Ci-C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfmyl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, ( Ci-C 8) haloalky
  • R 3 and R 4 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms, or
  • R 3 and R 4 together form a (C 1 -C 3 ) -alkylidene radical or (C 1 -C 3) -haloalkylidene radical,
  • R 5 represents hydrogen, (Ci-Cg) alkyl, (Ci-Cg) haloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) - Halocycloalkyl- (Ci-C 6) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) haloalkoxy (Ci- C 8) alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, (Ci-Cg) -Alkylsulfmyl
  • 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 2 PO 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 2 PO 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.
  • Sulfonklareamide or carboxylic acids may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate are compounds in which the azide 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 ammonium salts, for example with cations of the formula
  • R a to R d are each independently an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and
  • Alkylsulfoxoniumsalze such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
  • substituted arylpyrazoles of the general formula (I) according to the invention may be present in various tautomeric structures, all of which are of the general formula (I), depending on external conditions such as pH, solvent and temperature.
  • Preferred subject of the invention are compounds of the general formula (I) wherein
  • A is oxygen, -S (O) "-, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond,
  • n 0, 1 or 2
  • Q 1 is an optionally substituted aryl, heteroaryl, (C 3 -C 10) -cycloalkyl or (C 3 -C 10) -cycloalkenyl, each ring or ring system being optionally substituted with up to 5 substituents from the group R 6 ,
  • each ring or ring system is selected from carbon atoms and 1-5
  • each ring or ring system is optionally substituted with up to 5 substituents from the group R 6 ,
  • radical Q 1 is other than imidazole or 1, 2,4-triazole, groups Ql to Q-10
  • R 1 and R 2 together form an alkyl (CH 2 ) m ring where m is 3, 4 or 5,
  • R 3 and R 4 are each independently hydrogen, hydroxy, halogen, (Ci-Cg) alkyl, (Ci-Cg) - haloalkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (Ci -C 6) alkoxy- (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy (Ci-C 6) alkyl, (Ci-Cg) alkylthio (Ci-Cg) alkyl, (Ci-Cg) -alkylsulfmyl (Ci-Cg) -alkyl, (Ci-Cg) -alkylsulfonyl- (Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C3 -Cg) -cycloalkylcarbon
  • R 3 and R 4 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms,
  • R 3 and R 4 together form a (C 1 -C 3 ) -alkylidene radical or (C 1 -C 3) -haloalkylidene radical,
  • R 5 represents hydrogen, (Ci-C 8) -alkyl, (Ci-C8) haloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) - Halocycloalkyl- (Ci-C 6) - alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) haloalkoxy ( C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl,
  • R 6 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) - alkenyl, (C 2 -C 8) alkynyl , (C 2 -C 4) haloalkenyl, (C 2 -C 5) haloalkynyl, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, (Ci-C 4) haloalkoxy (C -C 4) alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, (Ci-C 8) - Alkylsulfmyl- (Ci-C 8) alkyl, (Ci-C 8) - Alkylsulfonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alky
  • R 8 is hydrogen, amino, hydroxy, cyano, formyl, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (Ci-Cg) - cyanoalkyl, (Ci-C8) hydroxyalkyl, (C -C 8) alkoxy- (Ci-C 8) alkyl, aryl (Ci-C8) alkyl,
  • a particularly preferred subject of the invention are compounds of the general formula (I) in which A is oxygen, sulfur, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond,
  • Q 1 is an optionally substituted aryl or heteroaryl, each ring optionally substituted with up to 5 substituents from the group R 6 ,
  • radical Q 1 is other than imidazole or 1, 2,4-triazole;
  • Q 2 stands for the groupings Ql to Q-4 specifically mentioned in the table above,
  • R 1 is hydrogen, (C 1 -C 3 ) -alkyl, (C 1 -C 3 ) -haloalkyl, (C 1 -C 3 ) -cyanoalkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 3 ) -alkyl, (Ci-C 4) haloalkoxy (Ci-C 3) alkyl, (Ci-C 4) alkylthio (Ci-C 3) alkyl, (Ci-C4) - Alkylsulfmyl- (Ci-C 3 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl- (C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -cycloalkylthio (C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -cycloalkylthio (C 1 -
  • R 2 is hydrogen, halogen, cyano, (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -haloalkyl, (C 1 -C 5 ) -cyanoalkyl, (C 1 -C 5 ) -hydroxyalkyl, (C 1 -C 4 ) Alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkoxy- (C 1 -C 5 ) -alkyl, (C 1 -C 4 ) -haloalkoxy- (C 1 -C 5 ) -alkyl, aryl- Ci-C 4) alkyl, heteroaryl (Ci-C 4) alkyl, heterocyclyl (Ci-C4) - alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) -cycloalkyl- ( Ci-C 5) alkyl, (
  • R 1 and R 2 together form an alkyl (CH 2 ) m ring, where m is 3, 4 or 5,
  • R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl,
  • R 5 represents hydrogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, aryl (Ci-C 3) alkyl, heteroaryl (Ci-C 3) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (Ci-C 4) alkylcarbonyl, (Ci-C4) haloalkylcarbonyl, formyl, (Ci-C4) alkoxycarbonyl, (C 2 -C 4) - Haloalkoxycarbonyl, (C 2 -C 4) -alkylaminocarbonyl, (C 3 -C 6) -dialkylaminocarbonyl,
  • R 6 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 8) -alkyl, (Ci-C 4) -haloalkyl, (C2-C4) - alkenyl, (C 2 -C 4) -alkynyl, ( C 2 -C 4) haloalkenyl, (C 2 -C 4) haloalkynyl, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (Ci-C 4) alkylthio (Ci-C 4) alkyl, (C1-C4) - Alkylsulfmyl- (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl ( C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbony
  • R 9 , R 10 , R 11 and R 12 independently of one another represent hydrogen, halogen, cyano, (C 1 -C 4) -alkyl,
  • A is oxygen, sulfur, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond,
  • Q 1 is an optionally substituted aryl or heteroaryl, each ring optionally substituted with up to 5 substituents from the group R 6 ,
  • the group Q 1 is other than imidazole or 1, 2,4-triazole, groups Q-11 to Q-14;
  • R 1 is hydrogen, methyl, ethyl, isopropyl, (C 1 -C 2 ) -haloalkyl, cyanomethyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 2 ) -alkyl, (C 1 -C 4 ) -alkylthio ( Ci-C 2) alkyl, (Ci-C 4) -Alkylsulfmyl- (Ci-C 2) alkyl, (C 1 -C 4) - alkylsulfonyl (Ci-C 2) alkyl, arylmethyl, (C 2 - C 6) alkenyl, (Ci-C 6) -alkoxycarbonyl, (C 3 -C 6) - cycloalkoxycarbonyl, (Ci-C6) alkoxycarbonyloxy (Ci-C 2) alkyl, (Ci-C6) alkylcarbonyloxy (C 1 -C 2 )
  • R is hydrogen, halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -cyanoalkyl, (C 1 -C 4 ) -hydroxyalkyl, (C 1 -C 3 ) alkoxy (Ci-C 4) alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci C 4) alkyl, (C 2 -C 4) alkenyl , (C 2 -C 4) -alkynyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) haloalkynyl, (Ci-C6) - alkoxycarbonyl, (Ci-C 6) alkenyloxycarbonyl, ( C 2 -C 6) -haloalkoxycarbonyl
  • R 1 and R 2 together form an alkyl (CH 2 ) m ring, where m is 3 or 4,
  • R 3 and R 4 independently of one another are hydrogen, halogen, methyl or ethyl
  • R 5 is hydrogen, methyl, ethyl, formyl or acetyl
  • R 6 is hydrogen, halogen, cyano, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C 3) alkoxy, (C1-C3) - haloalkoxy, methyl-S (0) n , where n is 0, 1 or 2, R 10 is hydrogen, halogen, cyano, methyl, trifluoromethyl, methoxy.
  • An extremely preferred subject of the invention are compounds of the general formula (I) in which A represents oxygen, sulfur, -CH 2 -, -NR 5 - or a simple bond,
  • Q 1 is an optionally substituted aryl or heteroaryl, each ring optionally substituted with up to 5 substituents from the group R 6 ; and in the case where A is a single bond, the radical Q 1 is other than imidazole or 1, 2,4-triazole;
  • Q 2 stands for groups Q-11 to Q-13
  • R 1 is hydrogen, methyl, ethyl, isopropyl, difluoromethyl, 2-methoxyethyl, 2-methylsulfanylethyl, benzyl, vinyl, allyl, tert-butoxycarbonyl
  • R is hydrogen, cyano, methyl, ethyl, propyl, trifluoromethyl, cyanomethyl, cyclopropyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, amino, acetylamino, or R 1 and R 2 together form an alkyl (CH 2 ) 3 ring
  • R 5 is Is hydrogen or methyl
  • R 6 represents hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy,
  • R 10 is hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy.
  • alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms eg (but not limited to) (C 1 -C 6) alkylsulfonyl such as methylsulfonyl, ethyl sulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1, 1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentyls
  • 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.
  • alkylthio alone or as part of a chemical group - is straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cio) -, (CI-C ⁇ ) - or (Ci-C4) -alkylthio, e.g. (but not limited to) (ce-Ce) -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1 Dimethylbut
  • Alkenylthio in the invention means an alkenyl radical bonded via a sulfur atom
  • Alkynylthio represents an alkynyl group bonded through a sulfur atom
  • cycloalkylthio represents a cycloalkyl group bonded through a sulfur atom
  • cycloalkenylthio represents an above
  • Alkoxy means an alkyl radical bonded through an oxygen atom, for example (but not limited to) (C 1 -C 6) alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy , 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy , 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-
  • Alkenyloxy means an alkenyl radical bonded through an oxygen atom
  • alkynyloxy means an above an oxygen atom bonded alkynyl group such as (C 2 -C 1 0) -, (C 2 -C 6) - or (C 2 -C 4) alkenoxy, and (C3-C10) -, (C 3 -C 6) - or (C 3 -C 4 ) -alkoxy.
  • Cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom and cycloalkenyloxy denotes a cycloalkenyl radical bonded via an oxygen atom.
  • the number of C atoms refers to the alkyl radical in the
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of carbon atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • alkynyloxycarbonyl the number of carbon atoms refers to the alkenyl and alkynyl in the alkene or alkynyloxycarbonyl.
  • the number of carbon atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • 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
  • optionally substituted aryl are also Vectorcyclische systems, such as
  • aryl is usually also of the term Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio , Haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalk
  • Alkylaminocarbonyl cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
  • heterocyclic radical contains at least one heterocyclic ring
  • heterocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P
  • N, O, S, P saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom.
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • optionally substituted heterocyclyl also become
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 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 are to be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2 or 3-yl, 2,3- dihydro-lH-pyrrole
  • 3-membered ring and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
  • 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-I or 2- or
  • 6-yl 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl;
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, l, 4,2-dioxazolidin-2 or 3 or 5-yl; l, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazine-3 or 5 or 6-yl; l, 4,2-dioxazine-3- or 5- or 6-yl; l, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1,
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • the 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. For example, at N and S, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • -N (O) and -S (0) groups both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie.
  • Heteroaryls according to the invention are, for example, 1H-pyrrol-1-yl; lH-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazol-1-yl; lH-imidazol-2-yl; 1H-imidazol-4-yl; lH-imidazol-5-yl; lH-pyrazol-l-yl; lH-pyrazol-3-yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-l, 2,3-triazol-4-yl, 1H-l, 2,
  • Carbon atoms part of another aromatic ring they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatic.
  • quinolines e.g., 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 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-indol-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-benzothiophene-2-yl, 1-benzothiophen-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5 yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazole
  • Benzisoxazol-7-yl 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1, 2 benzisothiazol-7-yl.
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted and is referred to in the latter case as “substituted alkyl”.
  • 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.
  • the prefix "to" closes also the combination of different alkyl radicals, z. For example, methyl (ethyl) or ethyl (methyl).
  • Haloalkyl means by the same or different halogen atoms, partially or fully substituted alkyl, alkenyl and alkynyl, for example monohaloalkyl
  • ( Monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. B. CCl 3, CC1F 2, CFC1 2 CF 2 CC1F 2, CF 2 CC1FCF 3; Polyhaloalkyl such. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3; The term perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, it being possible for the corresponding fluorine atoms to be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, for example CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated
  • Hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, wherein all other optional 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 complete substitution of halogen with the participation of at least one fluorine atom of the straight-chain or branched chain.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl, and the same applies to haloalkenyl and other radicals substituted by halogen.
  • (C 1 -C 4) -alkyl denotes a short notation for straight-chain or branched alkyl having one to four carbon atoms corresponding to the formula
  • Range indication 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.
  • the hydrocarbon radicals such as alkyl, alkenyl and
  • Alkinyl radicals even in composite radicals, the lower carbon skeletons, for example with 1 to 6 carbon atoms or in unsaturated groups having 2 to 6 carbon atoms, preferably.
  • Alkyl radicals also in the Compound 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. Preference is given to radicals having a double bond or
  • alkenyl in particular 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 cumulated double bonds, such as 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, for example (but not limited to) (C 2 -C 6) alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl , 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3 Pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl -2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl
  • C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 Pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1 - Ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-2-pentynyl
  • cycloalkyl means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl,
  • Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on
  • polycyclic aliphatic systems are also included, such as, for example, bicyclo [1,1.0] butan-1-yl, bicyclo [1,1-0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl , Bicyclo [1,11] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1 ] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantane-1-yl and adamantane -2-yl, but also systems such.
  • spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl.
  • 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 substituents having a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene, are also included in the case of optionally substituted cycloalkenyl the explanations for substituted Corresponding to cycloalkyl.
  • substituents having a double bond on the cycloalkenyl radical for example an alkylidene group such as methylidene
  • Cycloalkylalkyloxy means a cycloalkylalkyl radical bonded via an oxygen atom
  • arylalkyloxy means an arylalkyl radical bonded via an oxygen atom
  • Alkoxyalkyl means an alkoxy group attached via an alkyl group
  • alkoxyalkoxy means an alkoxyalkyl group bonded through an oxygen atom, for example (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl means an alkylthio radical bonded via an alkyl group
  • Alkylthioalkylthio means an alkylthioalkyl radical bonded via an oxygen atom.
  • Arylalkoxyalkyl stands for an aryloxy radical bound via an alkyl group
  • Heteroaryloxyalkyl means a heteroaryloxy group attached via an alkyl group.
  • Haloalkoxyalkyl means a haloalkoxy group attached and "haloalkylthioalkyl” means a haloalkylthio group attached via an alkyl group.
  • Arylalkyl means an aryl group attached via an alkyl group
  • heteroarylalkyl means a heteroaryl group bonded via an alkyl group
  • heterocyclylalkyl means a heterocyclyl group bonded through an alkyl group.
  • Cycloalkylalkyl means a cycloalkyl radical attached via an alkyl group, for example (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylpropyl l -yl, 3-cyclopropylprop-1-yl.
  • Arylalkenyl is an aryl radical bonded via an alkenyl group
  • heteroarylalkenyl denotes a heteroaryl radical bonded via an alkenyl group
  • heterocyclylalkenyl denotes a heterocyclyl radical bonded via an alkenyl group
  • Arylalkynyl denotes an aryl radical bonded via an alkynyl group
  • heteroarylalkynyl represents a heteroaryl group bonded via an alkynyl group
  • heterocyclylalkynyl means a heterocyclyl group bonded via an alkynyl group.
  • haloalkylthio alone or as part of a chemical group - is straight-chain or branched S-haloalkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cs) -, (CI-C ⁇ ) - or (Ci-C4) haloalkylthio, for example (but not limited to) Trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
  • Halocycloalkyl and “Halocycloalkenyl” mean by the same or different halogen atoms, such as. B. F, Cl and Br, or by haloalkyl, such as. Trifluoromethyl or difluoromethyl, partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • trialkylsilyl alone or as part of a chemical group - is straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as tri - [(Ci-Cg) -, (Ci-Ce) - or (Ci-C4) -alkyl] silyl, e.g. (but not limited to) trimethylsilyl, triethylsilyl, tri (n-propyl) silyl, tri (iso-propyl) silyl, tri (n-butyl) silyl, tri (1-methylprop-1-yl) silyl, Tri- (2-methylprop-1-yl) silyl, tri (1,1-dimethyl-1-yl) silyl, tri (2,2-dimethyl-1-yl) silyl.
  • the compounds of the general formula (I) can 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 general 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 distinguished from those in the
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants become.
  • 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.
  • the purification can also by
  • Suitable isolation, purification and stereoisomer separation methods of compounds of general formula (I) are those which are well known to those skilled in the art from analogous cases, e.g. by physical methods such as crystallization, chromatographic methods, especially column chromatography and HPLC (high performance liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods, residual mixtures may optionally be removed by chromatographic separation, e.g. at chiral solid phases, to be separated.
  • chromatographic separation e.g. at chiral solid phases
  • the present invention also claims processes for the preparation of the compounds of the general formula (I) according to the invention.
  • the compounds of the general formula (I) according to the invention can be prepared inter alia starting from known processes.
  • the synthetic routes used and investigated are based on commercially available or easily manufacturable building blocks.
  • alkylating agents such as Q 2 -X, wherein X is a leaving group
  • copper (I) salts are prepared.
  • the base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium).
  • the copper salts may be copper halides, such as cuprous iodide.
  • the reactions are generally in an organic
  • Solvent such as acetonitrile or dimethylformamide
  • Solvent such as acetonitrile or dimethylformamide
  • the pyrazoles of the general formula (E-III) can be prepared via a dealkyation of the pyrazoles (E-II) in the presence of acids such as, for example, hydrobromic acid.
  • the reactions are generally incorporated in an organic solvent such as acetic acid
  • the pyrazoles of the general formula (E-II) can be prepared via a Bisalkytechnik of pyrazolones (E-I) in
  • Presence of bases and Alkytechniksstoffn such as R'-X, where X is a leaving group can be produced.
  • the base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium).
  • the reactions are generally carried out in an organic solvent, such as acetonitrile or tetrahydrofuran, at temperatures between 0 ° C and the boiling point of the solvent.
  • the pyrazoles of the general formula (I) can be prepared via an alkylation of the pyrazolones (Ia) in the presence of bases and alkylating agents such as R'-X, where X is a leaving group.
  • the base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium) or an amine (such as triethylamine). The reactions are in the
  • the pyrazoles of general formula (Ia) can be prepared via deprotection of the pyrazoles (E-VI) in the presence of acids such as trifluoroacetic acid.
  • the reactions are generally carried out in an organic solvent, such as dichloromethane, or in
  • the pyrazoles of the general formula (E-VI) can be prepared via an alkylation of the pyrazolones (EV) in the presence of bases and alkylating agents such as Q 2 -X, where X is a leaving group.
  • the base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium).
  • the reactions are generally carried out in an organic solvent, such as butyronitrile, acetonitrile or dimethylformamide, at temperatures between 0 ° C and the boiling point of the solvent.
  • the compounds of the general formula (EV) can be obtained by reaction of the building blocks (E-IV) with
  • Hydrazines such as NF NH-PG, where PG is a protecting group.
  • the hydrazines used in this case can be present in free form or as salts, for example as Hydrochloride.
  • an organic or inorganic base such as triethylamine.
  • the protecting group PG may be, for example, benzyl or 4-methoxybenzyl.
  • the reaction is generally carried out in an organic solvent, such as ethanol, at temperatures between 0 ° C and the boiling point of the solvent.
  • Keto esters of the general formula (E-IV) are known from the literature and can be prepared, for example, according to the methods described in Tetrahedron, 1982, 38, 85-91, J. Am. Chem. Soc. 2013, 135, 14556-14559 and similarly described methods. As known to those skilled in the art, the ketoesters E-IV may also be present in their corresponding other tautomeric form.
  • the pyrazoles of the general formula (Ib) can be prepared via a substitution reaction of the pyrazoles (E-IX) with sulfur nucleophiles such as Q 2 -SH in the presence of bases and copper (I) salts.
  • the base may be a hydride salt of an alkali metal (such as sodium).
  • the copper salts may be copper halides, such as cuprous iodide.
  • Reactions are generally in an organic solvent, such as
  • the pyrazoles of general formula (E-IX) may be prepared by iodination of the pyrazoles (E-VIII) with a suitable iodinating agent, such as iodine, in the presence of ceric ammonium nitrate.
  • the reactions are generally carried out in an organic solvent, such as acetonitrile, at temperatures between 0 ° C and the boiling point of the solvent.
  • the pyrazoles of the general formula (E-VIII) can be prepared via an alkylation of the pyrazolones (E-VII) in the presence of bases, alkylating agents such as Q 2 -X, where X is a leaving group, and copper (I) salts become.
  • the base may be a carbonate salt of an alkali metal (such as for example, sodium, potassium or cesium).
  • the copper salts may be copper halides, such as cuprous iodide.
  • the reactions are generally in an organic
  • Solvent such as acetonitrile or dimethylformamide, at temperatures between 0 ° C and the boiling point of the solvent carried out.
  • the pyrazoles of the general formula (Ic) can be prepared via a Suzuki reaction of the pyrazoles (E-IX) with boronic acids such as, for example, Q 2 -B (OH) 2 in the presence of bases and palladium catalysts (such as PdC ⁇ dppfXCFhCL) ) getting produced.
  • the base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium).
  • the reactions are generally carried out in an organic solvent, such as dioxanes, at temperatures between 0 ° C and the boiling point of the solvent.
  • the base may be a hydride salt of an alkali metal (such as sodium).
  • the reactions are generally carried out in an organic solvent, such as acetonitrile, tetrahydrofuran or dimethylformamide, at temperatures between 0 ° C and
  • the pyrazoles of general formula (Id) can be obtained via a Buckwald-Hartwig coupling of the pyrazoles (E-XI) with aryl halides or aryl triflates such as, for example, Q l -X in the presence of bases, palladium catalysts (for example tris (dibenzylideneacetone) dipalladium (0)) and ligands (such as
  • Example Xantphos are produced.
  • the base may be a phosphate salt of an alkali metal (such as sodium, potassium or cesium).
  • the reactions are generally carried out in an organic solvent, such as toluene, at temperatures between 0 ° C and
  • the pyrazoles of the general formula (E-XI) can be prepared via a reduction of the pyrazoles (E-X). Such reactions are known to the person skilled in the art and are described, for example, in WO2008 / 8375 A2 and WO201 1/3065 A2.
  • the pyrazoles of the general formula (E-X) can be prepared via a nitration of the pyrazoles (E-VIII). Such reactions are known to the skilled person and, for example, in
  • the sulfones and sulfoxides of the general formula (If) can be prepared via an oxidation of the pyrazoles (Ib). Such reactions are known to the person skilled in the art and are described, for example, in Eur. J. Med. Chem. 2014, 71, 168-184 and Org. Lett. 2013, 15, 3994-3997. Selected detailed synthesis examples of the compounds of the general formula (I) according to the invention are listed below.
  • n-Bu unbranched butyl
  • n-Pr unbranched propyl
  • i-Pr branched propyl
  • c-Pr cyclopropyl
  • c-hex cyclohexyl.
  • the reaction mixture was treated again with dimethyl sulfate (6.8 ml, 72.4 mmol, 2.0 equiv) and stirred at 70 ° C for a further 3 hours and then cooled to room temperature, added water and dichloromethane and then the phases were separated. The aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then washed with water and sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated.
  • aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were then washed with water (x3) and sat. Sodium chloride solution (xl), dried over magnesium sulfate, filtered and concentrated.
  • Tris (dibenzylideneacetone) dipalladium (0) 49 mg, 0.054 mmol, 0.05 equiv
  • xanthophos 62 mg, 0.11 mmol, 0.1 equiv
  • potassium phosphate 455 mg, 2.14 mmol, 2.0 equiv.

Abstract

The invention relates to substituted 3-heteroaryloxy-1H-pyrazoles of general formula (I). Disclosed are substituted 3-heteroaryloxy-1H-pyrazoles of general formula (I), their use as herbicides, in particular for controlling weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The present invention further relates to herbicidal and/or plant growth-regulating agents comprising one or more compounds of general formula (I).

Description

Substituierte 3-Heteroaryloxy-lH-pyrazole sowie deren Salze und ihre Verwendung als herbizide Wirkstoffe  Substituted 3-heteroaryloxy-lH-pyrazoles and their salts and their use as herbicidal active ingredients
Beschreibung description
Die Erfindung betrifft das technische Gebiet der Pflanzenschutzmittel, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsern in Nutzpflanzenkulturen. The invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
Speziell betrifft diese Erfindung substituierte 3-Heteroaryloxy-lH-pyrazole sowie deren Salze, Specifically, this invention relates to substituted 3-heteroaryloxy-lH-pyrazoles and their salts,
Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide. Process for their preparation and their use as herbicides.
Bisher bekannte Pflanzenschutzmittel zur selektiven Bekämpfung von Schadpflanzen in Previously known crop protection agents for the selective control of harmful plants in
Nutzpflanzenkulturen oder Wirkstoffe zur Bekämpfung von unerwünschtem Pflanzenwuchs weisen bei ihrer Anwendung teilweise Nachteile auf, sei es, dass sie (a) keine oder aber eine unzureichende herbizide Wirkung gegen bestimmte Schadpflanzen, (b) ein zu geringes Spektrum der Schadpflanzen, das mit einem Wirkstoff bekämpft werden kann, (c) zu geringe Selektivität in Nutzpflanzenkulturen und/oder (d) ein toxikologisch ungünstiges Profil besitzen. Weiterhin führen manche Wirkstoffe, die als Pflanzenwachstumsregulatoren bei einigen Nutzpflanzen eingesetzt werden können, bei anderenCommercial crops or active substances for combating undesirable plant growth have some drawbacks in their application, be it that they (a) no or insufficient herbicidal activity against certain harmful plants, (b) a too low a range of harmful plants, which fights with an active ingredient (c) have too low selectivity in crops and / or (d) have a toxicologically unfavorable profile. Furthermore, some agents that can be used as plant growth regulators in some crops lead others
Nutzpflanzen zu unerwünscht verminderten Ernteerträgen oder sind mit der Kulturpflanze nicht oder nur in einem engen Aufwandmengenbereich verträglich. Einige der bekannten Wirkstoffe lassen sich wegen schwer zugänglicher Vorprodukte und Reagenzien im industriellen Maßstab nicht wirtschaftlich herstellen oder besitzen nur unzureichende chemische Stabilitäten. Bei anderen Wirkstoffen hängt die Wirkung zu stark von Umweltbedingungen, wie Wetter- und Bodenverhältnissen ab. Crops to undesirably reduced crop yields or are not compatible with the crop or only in a narrow application rate range. Some of the known active compounds can not be produced economically on the industrial scale because of difficultly accessible precursors and reagents or have only insufficient chemical stabilities. For other active ingredients the effect depends too much on environmental conditions, such as weather and soil conditions.
Die herbizide Wirkung dieser bekannten Verbindungen, insbesondere bei niedrigen Aufwandmengen, bzw. deren Verträglichkeit gegenüber Kulturpflanzen bleiben verbesserungswürdig. Verschiedene Schriften beschreiben substituierte Heteroaryloxypyrazole. In JP2002/348280 und J. Pestic. Sei. 2004, 29, 96-104 sind Heteroaryloxypyrazole als Herbizide beschrieben, die in der 4- Position des Pyrazols mit Carbamoyl- oder Acylaminoresten substituiert sind. In JP07285962 werden Heteroaryloxypyrazole benannt, die in der 3 -Position des Pyrazols spezifisch mit Wasserstoff oder Halogen substituiert sind und als Herbicide beansprucht werden. In WO2002/066439 werden The herbicidal action of these known compounds, in particular at low application rates, or their compatibility with crop plants, should be improved. Various documents describe substituted heteroaryloxypyrazoles. In JP2002 / 348280 and J. Pestic. Be. 2004, 29, 96-104 heteroaryloxypyrazoles are described as herbicides which are substituted in the 4-position of the pyrazole with carbamoyl or Acylaminoresten. JP07285962 names heteroaryloxypyrazoles which are specifically substituted in the 3-position of the pyrazole with hydrogen or halogen and are claimed as herbicides. WO2002 / 066439
Heteroaryloxypyrazole benannt, die in der 1 -Position des Pyrazols spezifisch mit Carbamoylresten substituiert sind und als Herbicide beansprucht werden. In WO2016/124769 werden Named heteroaryloxypyrazoles which are specifically substituted in the 1-position of the pyrazole with carbamoyl and claimed as herbicides. WO2016 / 124769
Heteroaryloxypyrazole benannt, die in der 1 -Position des Pyrazols spezifisch mit Alkinylresten substituiert sind und als Nitrification Inhibitors beansprucht werden. In WO2003/144309 werden Heteroaryloxypyrazole benannt, die in der 4-Position des Pyrazols spezifisch mit Aminopyridine oder Aminopyrimidine substituiert sind und als Proteinkinase-Inhibitoren mit pharmazeutischen Nutzen beansprucht werden. In JP2000/095778 werden Heteroaryloxypyrazole benannt, die in der 4-Position des Pyrazols spezifisch mit Imidazole und 1 ,2,4-Triazole substituiert sind und als Fungicide beansprucht werden. Heteroaryloxypyrazoles named in the 1-position of the pyrazole specifically with alkynyl radicals are substituted and claimed as nitrification inhibitors. In WO2003 / 144309 Heteroaryloxypyrazole be named, which are specifically substituted in the 4-position of the pyrazole with aminopyridines or aminopyrimidines and claimed as protein kinase inhibitors with pharmaceutical benefits. In JP2000 / 095778 Heteroaryloxypyrazole be named, which are specifically substituted in the 4-position of the pyrazole with imidazoles and 1, 2,4-triazoles and claimed as fungicides.
Substituierte 3-Heteroaryloxy-lH-pyrazole oder deren Salze als herbizide Wirkstoffe sind dagegen bisher noch nicht beschrieben. Substituted 3-heteroaryloxy-lH-pyrazoles or their salts as herbicidal active ingredients, however, have not yet been described.
Überraschenderweise wurde nun gefunden, dass substituierte 3-Heteroaryloxy-lH-pyrazole oder deren Salze als herbizide Wirkstoffe besonders gut geeignet sind. Surprisingly, it has now been found that substituted 3-heteroaryloxy-lH-pyrazoles or their salts are particularly suitable as herbicidal active ingredients.
Gegenstand der vorliegenden Erfindung sind damit substituierte 3-Heteroaryloxy-lH-pyrazole der allgemeinen Formel (I) oder deren Salze The present invention thus provides substituted 3-heteroaryloxy-lH-pyrazoles of the general formula (I) or salts thereof
worin wherein
A für Sauerstoff, -S(0)„-, -C(R3)(R4) -, -NR5- oder eine einfache Bindung steht A is oxygen, -S (O) "-, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond
mit n gleich 0, 1 oder 2,  with n equal to 0, 1 or 2,
Q1 für ein gegebenenfalls substituiertes Aryl, Heteroaryl, (C3-Cio)-Cycloalkyl oder (C3-C10)-Q 1 represents an optionally substituted aryl, heteroaryl, (C 3 -C 10) -cycloalkyl or (C 3 -C 10) -
Cycloalkenyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist; Cycloalkenyl, each ring or ring system being optionally substituted with up to 5 substituents from the group R 6 ;
oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring oder für ein gegebenenfalls substituiertes 8-10-gliedriges bicyclisches, heterocyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten können, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können; und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR8) und S(=NR8)(=0) gewählt werden können; jeder Ring oder jedes Ringsystem ist optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert; or an optionally substituted 5-7 membered heterocyclic ring or an optionally substituted 8-10 membered bicyclic heterocyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms independently of one another up to 2O - Up to 2 S and up to 5 N atoms may contain up to three carbon ring atoms independently from the groups C (= 0) and C (= S) can be selected; and the sulfur ring atoms may additionally be selected from the groups S, S (= O), S (= O) 2, S (= NR 8 ), and S (= NR 8 ) (= O); every ring or every ring system is optionally substituted with up to 5 substituents from the group R 6 ;
oder für ein 8-10-gliedriges bicyclisches, carbocyclisches Ringsystem steht, das ungesättigt, teilweise gesättigt oder vollständig gesättigt ist, und das mit bis zu 5 Substituenten aus der Gruppe R6 substituiert sein kann, or is an 8-10 membered bicyclic, carbocyclic ring system which is unsaturated, partially saturated or fully saturated, and which may be substituted with up to 5 substituents from the group R 6 ,
und wobei für den Fall, dass A eine einfache Bindung representiert, der Rest Q1 ungleich Imidazol oder 1 ,2,4-Triazol ist, für ein gegebenenfalls substituiertes Heteroaryl steht, wobei jeder Ring optional mit bis zu 4 Substituenten aus der Gruppe R7 substituiert ist, für Wasserstoff, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-Hydroxyalkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)- alkyl, (Ci-C6)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)- Cycloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Cycloalkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)- Cycloalkylsulfonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-C6)-alkyl, (C3-C8)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Haloalkenyl, Tris-[(Ci-C6)- alkyl]silyl-(C2-C6)-alkinyl, Carboxyl, Carboxyl-(Ci-C6)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)- Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-C10)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C6)- alkyl, (C2-C8)- Haloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C2-C8)-Alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Dialkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C8)-Alkylcarbonyloxy-(Ci-C4)-alkyl, (Ci-C8)-Alkoxycarbonyloxy-(Ci-C4)-alkyl, (C3-C6)-Cycloalkoxycarbonyloxy-(Ci-C4)-alkyl, (Ci-C6)-Alkylsulfonyl, (Ci-C6)-Haloalkylsulfonyl, Arylsulfonyl, Phthalimidomethyl steht, für Wasserstoff, Halogen, Cyano, (Ci-C6)-Alkyl, (Ci-C6)-Haloalkyl, (Ci-C6)-Cyanoalkyl, (Ci- C6)-Hydroxyalkyl, (Ci-C6)-Alkoxy, (Ci-C6)-Haloalkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkoxy-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)- alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)- Halocycloalkyl-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Haloalkenyl, (C2-C6)- Haloalkinyl, Tris-[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, Carboxyl, Carboxyl-(Ci-C6)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, (Ci-Cg)- Alkoxycarbonyl, (Ci-C6)-Alkenyloxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C3-C8)- Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C8)- Haloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C2-Cg)- Alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Dialkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C10)- Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, Amino, (Ci-C6)-Alkylamino, (C2-Cio)-Dialkylamino, (Ci-C6)-Haloalkylamino, (C3-C8)-Cycloalkylamino, (C2-C8)-Alkenylamino, (C4-C10)- Dialkenylamino, (Ci-C6)-Alkylcarbonylamino, (C2-Cio)-(Dialkylcarbonyl)amino, (CI-CÖ)- Haloalkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, (N-(Ci-C6)-Alkylcarbonyl)-(Ci- C6)-alkylamino, (Ci-C6)-Alkyl-S(0)x steht, and wherein in the case that A represents a single bond, the radical Q 1 is not imidazole or 1, 2,4-triazole, is an optionally substituted heteroaryl, each ring optionally having up to 4 substituents from the group R 7 is substituted hydrogen, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (Ci-C 8) cyanoalkyl, (Ci-C8) hydroxyalkyl, (Ci-C 6) alkoxy - (Ci-C 6 ) -alkyl, (Ci-C 6 ) -haloalkoxy- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkylthio (Ci-C 6 ) - alkyl, (Ci-C6 ) -Alkylsulfmyl- (Ci-C 6) alkyl, (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl, (Ci-C 6) - cycloalkylthio (Ci-C 6) alkyl, ( C 1 -C 6 ) -cycloalkylsulfmyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -cycloalkylsulfonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 8) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) - halocycloalkyl, (C 3 -C 6) -Halocycloalkyl- (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, tris - [(Ci-C 6) - alkyl] silyl (C 2 -C 6 ) alkynyl, C arboxyl, carboxyl (Ci-C 6) alkyl, (Ci-C 8) alkylcarbonyl, (Ci-C 8) - haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (Ci-C8) alkoxycarbonyl, ( C 2 -C 8) - haloalkoxycarbonyl, (C3-C8) -cycloalkoxycarbonyl, (C 2 -C 8) -alkylaminocarbonyl, (C3-C 1 0) - alkylaminocarbonyl, (C3-Cio) cycloalkylaminocarbonyl, (Ci-C 8) alkoxycarbonyl (Ci-C6) - alkyl, (C 2 -C 8) - Haloalkoxycarbonyl- (Ci-C6) alkyl, (C3-C8) -Cycloalkoxycarbonyl- (Ci-C6) alkyl, (C C 2 -C 8 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 3 -C 10) -dialkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 3 -C 10) -cycloalkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (Ci C8) alkylcarbonyloxy (Ci-C4) alkyl, (Ci-C 8) alkoxycarbonyloxy (Ci-C4) alkyl, (C3-C6) cycloalkoxycarbonyloxy (Ci-C4) alkyl, (C -C 6 ) -alkylsulfonyl, (C 1 -C 6 ) -haloalkylsulfonyl, arylsulfonyl, phthalimidomethyl, represents hydrogen, halogen, cyano, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) Cyanoalkyl, (C 1 -C 6 ) -hydroxyalkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (Ci -C 6 ) - haloalkoxy- (Ci-C 6 ) -alkyl, aryl- (Ci-C 6 ) -alkyl, heteroaryl- (Ci-C 6 ) -alkyl, heterocyclyl- (Ci-C 6 ) - alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) - Halocycloalkyl- (Ci-C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, tris - [(ci) C6) alkyl] silyl (C 2 -C 6) alkynyl, carboxyl, carboxyl (Ci-C 6) alkyl, (Ci-C 8) alkylcarbonyl, (Ci-C 8) haloalkylcarbonyl, (C3 -C 8) cycloalkylcarbonyl, (Ci-Cg) - alkoxycarbonyl, (Ci-C6) alkenyloxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C3-C8) - cycloalkoxycarbonyl, (C 2 -C 8) - alkylaminocarbonyl, (C3-Cio) dialkylaminocarbonyl, (C3-C 1 0) - cycloalkylaminocarbonyl, (Ci-C8) alkoxycarbonyl (Ci-C6) alkyl, (C 2 -C 8) - Haloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 8 ) -cycloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -CG) -alkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 10) -alkyl) Dialkylaminocarbonyl (C 1 -C 6) -alkyl, (C 3 -C 10) -cycloalkylaminocarbonyl- (C 1 -C 6) -alkyl, amino, (C 1 -C 6) -alkylamino, (C 2 -C 10) -dialkylamino, (C 1 -C 6) -cycloalkylaminocarbonyl- (C 1 -C 6) -alkyl; ) -Haloalkylamino, (C3-C8) -cycloalkylamino, (C2-C8) -alkenylamino, (C4-C10) -dialkenylamino, (Ci-C6) -alkylcarbonylamino, (C2-Cio) - (dialkylcarbonyl) -amino, (CI- CÖ) - haloalkylcarbonylamino, (C 3 -C 8) -cycloalkylcarbonylamino, (N- (C 1 -C 6 ) -alkylcarbonyl) - (C 1 -C 6 ) -alkylamino, (C 1 -C 6 ) -alkyl-S (0) x ,
wobei x gleich 0, 1 oder 2 ist, oder  where x is 0, 1 or 2, or
R1 und R2 zusammen einen Alkyl-(CH2)m-Ring bilden, wobei m gleich 3, 4 oder 5 ist, R 1 and R 2 together form an alkyl (CH 2 ) m ring where m is 3, 4 or 5,
R3 und R4 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-Cg)-Alkyl, (Ci-Cg)- Haloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkoxy-(Ci-C6)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfmyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-Cg)- Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-Cg)-Alkoxy, (Ci-Cg)-Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-Cg)- Cycloalkylthio, stehen, oder R 3 and R 4 independently of one another represent hydrogen, hydroxyl, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy (Ci-C 6) alkyl, (Ci-C8) alkylthio (Ci-C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfmyl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, ( Ci-C 8) haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C 4 -CG) - cycloalkoxycarbonyl, (C2-C8 ) -Alkylaminocarbonyl, (C3-Cio) -dialkylaminocarbonyl, (C3-C10) -cycloalkylaminocarbonyl, (Ci-Cg) -alkoxy, (Ci-Cg) -alkylthio, (Ci-Cg) -haloalkylthio, (C 3 -Cg) - Cycloalkylthio, stand, or
R3 und R4 gemeinsam einen 3- bis 6-gliedrigen carbocyclischen Ring oder einen 3- bis 6-gliedrigen gesättigten heterocyclischen Ring mit bis zu 2 Sauerstoffatomen bilden, oder R 3 and R 4 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms, or
R3 und R4 gemeinsam einen (Ci-C3)-Alkylidenrest oder (Ci-C3)-Haloalkylidenrest bilden, R 3 and R 4 together form a (C 1 -C 3 ) -alkylidene radical or (C 1 -C 3) -haloalkylidene radical,
R5 für Wasserstoff, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)- Halocycloalkyl-(Ci-C6)-alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-Cg)-Alkylsulfmyl- (Ci-Cg)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)- Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Formyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-C10)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl steht, für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-Cg)-Alkyl, (Ci-C8)-Haloalkyl, (C2-C8)- Alkenyl, (C2-C8)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C5)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfinyl- (Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)- Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-C10)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)-Alkylsulfmyl, (Ci-C8)- Haloalkylsulfmyl, (C3-C8)-Cycloalkylsulfmyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-C8)-Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (C2-C8)- Alkenyl, (C2-C4)-Haloalkenyl, (C2-C5)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (C1-C4)- Haloalkoxy-(Ci-C4)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfmyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)- Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)- Cycloalkylthio, (Ci-C8)-Alkylsulfmyl, (Ci-C8)-Haloalkylsulfmyl, (C3-C8)-Cycloalkylsulfmyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (Ci-C8)- Alkylaminosulfonyl, (C2-C8)-Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, und für Wasserstoff, Amino, Hydroxy, Cyano, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-Cs)- Cyanoalkyl, (Ci-C8)-Hydroxyalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, R 5 represents hydrogen, (Ci-Cg) alkyl, (Ci-Cg) haloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) - Halocycloalkyl- (Ci-C 6) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) haloalkoxy (Ci- C 8) alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, (Ci-Cg) -Alkylsulfmyl- (Ci-Cg) alkyl, (Ci-C8) alkylsulfonyl ( Ci-C 8) alkyl, (Ci-Cg) alkylcarbonyl, (Ci-Cg) - haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, formyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8 ) - Haloalkoxycarbonyl, (C 4 -C 8) -cycloalkoxycarbonyl, (C 2 -C 8) -alkylaminocarbonyl, (C3-C 1 0) - alkylaminocarbonyl, (C3-Cio) cycloalkylaminocarbonyl, represents hydrogen, halogen, cyano, nitro, formyl , (Ci-Cg) alkyl, (Ci-C8) -haloalkyl, (C 2 -C 8) - alkenyl, (C 2 -C 8) -alkynyl, (C 2 -C 4) haloalkenyl, (C 2 -C 5) haloalkynyl, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (Ci-C 8) - Alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfinyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl- (C 1 -C 8 ) -alkyl, C 8) alkylcarbonyl, (Ci-C 8) - haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, carboxy, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C 4 -C 8) -cycloalkoxycarbonyl, (C 2 -C 8) -alkylaminocarbonyl, (C3-C 1 0) - alkylaminocarbonyl, (C3-Cio) cycloalkylaminocarbonyl, (Ci-C 8) alkoxy, (Ci-C8) -haloalkoxy , (Ci-C8) alkylthio, (Ci-C8) haloalkylthio, (C 3 -C 8) -cycloalkylthio, (Ci-C 8) -Alkylsulfmyl, (Ci-C 8) - Haloalkylsulfmyl, (C3- C 8 ) cycloalkyl sulfmyl, (Ci-C8) alkylsulfonyl, (Ci-C 8) haloalkylsulfonyl, (C3-C8) cycloalkylsulfonyl, (Ci-C 8) alkylaminosulfonyl, (C 2 -C 8) dialkylaminosulfonyl, or (C 3 -C 8) trialkylsilyl, represents hydrogen, halogen, cyano, nitro, formyl, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) - alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 5) haloalkynyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (C 1 -C 4) - haloalkoxy (Ci-C 4 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfmyl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl- (C 1 -C 8 ) -alkyl Ci-C 8) alkyl, (Ci-C 8) alkylcarbonyl, (Ci-C 8) haloalkylcarbonyl, (C 3 -C 8) - cycloalkylcarbonyl, carboxyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8 ) - haloalkoxycarbonyl, (C 4 -C 8 ) - cycloalkoxycarbonyl, (C 2 -C 8 ) -alkylaminocarbonyl, (C 3 -C 10) -dialkylaminocarbonyl, (C 3 -C 10) -cycloalkylaminocarbonyl, (C 1 -C 8 ) alkoxy, (Ci-C8) alkylthio, (Ci-C8) haloalkylthio, (C 3 -C 8) - cycloalkylthio, (Ci-C 8) -Alkylsulfmyl, (Ci-C 8) -Haloalkylsulfmyl, (C 3 -C 8 ) cycloalky lsulfmyl, (Ci-C8) alkylsulfonyl, (Ci-C 8) haloalkylsulfonyl, (C 3 -C 8) cycloalkylsulfonyl, (Ci-C 8) - alkylaminosulfonyl, (C 2 -C 8) dialkylaminosulfonyl or ( C 3 -C 8 ) -trialkylsilyl, and represents hydrogen, amino, hydroxyl, cyano, formyl, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -cycloalkyl, C 8 ) -hydroxyalkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkyl,
Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Cycloalkyl- (Ci-C8)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)-Halocycloalkyl-(Ci-C8)-alkyl, (Ci-C8)- Alkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, Tris-[(Ci-C8)- alkyl]silyl-(C2-C8)-alkinyl, Tris-[(Ci-C8)-alkyl]silyl steht. Die Verbindungen der allgemeinen Formel (I) können durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SO4, HsPO i oder HNO3, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie zum Beispiel p- Toluolsulfonsäure, an eine basische Gruppe, wie z.B. Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. Geeignete Substituenten, die in deprotonierter Form, wie z.B. Sulfonsäuren, bestimmte Heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -cycloalkyl- (C 1 -C 8 ) -alkyl, ( C 3 -C 8) halocycloalkyl, (C 3 -C 8) -Halocycloalkyl- (Ci-C 8) alkyl, (Ci-C 8) - alkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 2 - C 8) alkenyl, (C 2 -C 8) -alkynyl, tris - [(Ci-C 8) - alkyl] silyl (C 2 -C 8) -alkynyl, tris - [(Ci-C 8) - alkyl] silyl. 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 2 PO or HNO 3, or organic acids, e.g. For example, carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which in deprotonated form, such as sulfonic acids, certain
Sulfonsäureamide oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Salzbildung kann auch durch Einwirkung einer Base auf Sulfonsäureamide or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of a base
Verbindungen der allgemeinen Formel (I) erfolgen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin und Pyridin sowie Ammonium-, Alkali- oder Compounds of the general formula (I) take place. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
Erdalkalimetallhydroxide, -carbonate und -hydrogencarbonate, insbesondere Natrium- und Alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and
Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der azide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate. These salts are compounds in which the azide hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre Ammoniumsalze, zum Beispiel mit Kationen der Formel  Alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
[NRaRbRcRd]+ worin Ra bis Rd jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Arylalkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und [NR a R b R c R d ] + wherein R a to R d are each independently an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and
Alkylsulfoxoniumsalze, wie (Ci-C4)-Trialkylsulfonium- und (Ci-C4)-Trialkylsulfoxoniumsalze. Alkylsulfoxoniumsalze, such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
Die erfindungsgemäßen substituierten Arylpyrazole der allgemeinenFormel (I) können in Abhängigkeit von äußeren Bedingungen, wie pH- Wert, Lösungsmittel und Temperatur in verschiedenen tautomeren Strukturen vorliegen, die alle von der allgemeinen Formel (I) umfasst sein sollen. The substituted arylpyrazoles of the general formula (I) according to the invention may be present in various tautomeric structures, all of which are of the general formula (I), depending on external conditions such as pH, solvent and temperature.
Im Folgenden werden die erfindungsgemäß verwendeten Verbindungen der Formel (I) und ihre Salze "Verbindungen der allgemeinen Formel (I)" bezeichnet. The compounds of the formula (I) used according to the invention and their salts are referred to below as "compounds of the general formula (I)".
Bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Preferred subject of the invention are compounds of the general formula (I) wherein
A für Sauerstoff, -S(0)„-, -C(R3)(R4) -, -NR5- oder eine einfache Bindung steht, A is oxygen, -S (O) "-, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond,
wobei n gleich 0, 1 oder 2 ist,  where n is 0, 1 or 2,
Q1 für ein gebenenfalls substituiertes Aryl, Heteroaryl, (C3-Cio)-Cycloalkyl oder (C3-C10)- Cycloalkenyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist, Q 1 is an optionally substituted aryl, heteroaryl, (C 3 -C 10) -cycloalkyl or (C 3 -C 10) -cycloalkenyl, each ring or ring system being optionally substituted with up to 5 substituents from the group R 6 ,
oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring, oder für ein gegebenenfalls substituiertes 8-10-gliedriges bicyclisches, heterocyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1 -5 or an optionally substituted 5-7 membered heterocyclic ring, or an optionally substituted 8-10 membered bicyclic heterocyclic ring system in which each ring or ring system is selected from carbon atoms and 1-5
Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N- Atome enthalten können, besteht und wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können und die  Heteroatoms consists of independently up to 2 O, up to 2 S and up to 5 N atoms may contain, and wherein up to three carbon atoms independently from the groups C (= 0) and C (= S) can be chosen and the
Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR8) und S(=NR8)(=0) gewählt werden können, Sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 8 ) and S (= NR 8 ) (= 0) can be selected,
jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist, each ring or ring system is optionally substituted with up to 5 substituents from the group R 6 ,
oder für ein 8-10-gliedriges bicyclisches, carbocyclisches Ringsystem steht, das ungesättigt, teilweise gesättigt oder vollständig gesättigt ist, und das mit bis zu 5 Substituenten aus der Gruppe R6 substituiert sein kann, or is an 8-10 membered bicyclic, carbocyclic ring system which is unsaturated, partially saturated or fully saturated, and which may be substituted with up to 5 substituents from the group R 6 ,
und wobei für den Fall, dass A eine einfache Bindung ist, der Rest Q1 ungleich Imidazol oder 1 ,2,4-Triazol ist, für die Gruppen Q-l bis Q-10 steht and wherein, in the case where A is a single bond, the radical Q 1 is other than imidazole or 1, 2,4-triazole, groups Ql to Q-10
Q-l Q-2 Q-3 Q-4 Q-5 Q-1 Q-2 Q-3 Q-4 Q-5
Q-7 Q-8 Q-9 Q-10 für Wasserstoff, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-Hydroxyalkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)- alkyl, (Ci-C6)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)- Cycloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Cycloalkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)- Cycloalkylsulfonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-C6)-alkyl, (C3-C8)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Haloalkenyl, Tris-[(Ci-C6)- alkyl]silyl-(C2-C6)-alkinyl, Carboxyl, Carboxyl-(Ci-C6)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)- Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C3-Cg)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-C10)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-Cg)-Alkoxycarbonyl-(Ci-C6)- alkyl, (C2-Cg)- Haloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-Cg)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C2-Cg)-Alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Dialkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-Cg)-Alkylcarbonyloxy-(Ci-C4)-alkyl, (Ci-Cg)-Alkoxycarbonyloxy-(Ci-C4)-alkyl, (C3-C6)-Cycloalkoxycarbonyloxy-(Ci-C4)-alkyl, (Ci-C6)-Alkylsulfonyl, (Ci-C6)-Haloalkylsulfonyl, Arylsulfonyl, Phthalimidomethyl steht, R2 für Wasserstoff, Halogen, Cyano, (Ci-C6)-Alkyl, (Ci-C6)-Haloalkyl, (Ci-C6)-Cyanoalkyl, (Ci- C6)-Hydroxyalkyl, (Ci-C6)-Alkoxy, (Ci-C6)-Haloalkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkoxy-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)- alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)- Halocycloalkyl-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Haloalkenyl, (C2-C6)- Haloalkinyl, Tris-[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, Carboxyl, Carboxyl-(Ci-C6)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)-Haloalkylcarbonyl, (C3-Cg)-Cycloalkylcarbonyl, (Ci-Cg)- Alkoxycarbonyl, (Ci-C6)-Alkenyloxycarbonyl, (C2-Cg)- Haloalkoxycarbonyl, (C3-Cg)- Cycloalkoxycarbonyl, (C2-Cg)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-Cg)-Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-Cg)- Haloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-Cg)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C2-Cg)- Alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Dialkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C10)- Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, Amino, (Ci-C6)-Alkylamino, (C2-Cio)-Dialkylamino, (Ci-C6)-Haloalkylamino, (C3-Cg)-Cycloalkylamino, (C2-Cg)-Alkenylamino, (C4-C10)- Dialkenylamino, (Ci-C6)-Alkylcarbonylamino, (C2-Cio)-(Dialkylcarbonyl)amino, (Ci-Ce)- Haloalkylcarbonylamino, (C3-Cg)-Cycloalkylcarbonylamino, (N-(Ci-C6)-Alkylcarbonyl)-(Ci- C6)-alkylamino, (Ci-C6)-Alkyl-S(0)x steht, Q-7 Q-8 Q-9 Q-10 for hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -cyanoalkyl, (C 1 -C 8 ) -hydroxyalkyl , (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 4 ) -alkyl) 6) - alkyl, (Ci-C6) -Alkylsulfmyl- (Ci-C 6) alkyl, (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl, (Ci-C 6) - cycloalkylthio ( C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -cycloalkylsulfmyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -cycloalkylsulfonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) - alkyl, heteroaryl (Ci-C6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 8) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl , (C 3 -C 6) halocycloalkyl, (C 3 -C 6) -Halocycloalkyl- (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, tris - [(Ci-C 6 ) alkyl] silyl (C 2 -C 6 ) alkynyl, carboxyl, carboxyl (Ci-C 6 ) alkyl, (Ci-C 8 ) alkylcarbonyl, (Ci-C 8 ) - haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - Haloalkoxycarbonyl, (C3-Cg) -cycloalkoxycarbonyl, (C 2 -C 8) -alkylaminocarbonyl, (C3-C 1 0) - alkylaminocarbonyl, (C3-Cio) cycloalkylaminocarbonyl, (Ci-Cg) alkoxycarbonyl (Ci-C6) - alkyl, (C 2 -Cg) - haloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 9) -cycloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -CG) -alkylaminocarbonyl- (C 1 -C 6) alkyl, (C 3 -C 10) -dialkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 10) -cycloalkylaminocarbonyl- (C 1 -C 6) -alkyl, (Ci-Cg) -alkylcarbonyloxy- (C 1 -C 4) -alkyl , (C 1 -C 6) -alkoxycarbonyloxy- (C 1 -C 4) -alkyl, (C 3 -C 6) -cycloalkoxycarbonyloxy- (C 1 -C 4) -alkyl, (C 1 -C 6) -alkylsulfonyl, (C 1 -C 6) -haloalkylsulfonyl, arylsulfonyl , Phthalimidomethyl, R 2 is hydrogen, halogen, cyano, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -cyanoalkyl, (C 1 -C 6 ) -hydroxyalkyl, ( C 1 -C 6 -alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) alkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) - alkyl, (C 3 -C 6) -cycloalkyl, (C3-C 6 ) -cycloalkyl- (Ci-C 6 ) -a lkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) - Halocycloalkyl- (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl , (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, tris [(C 1 -C 6 ) alkyl] silyl (C 2 -C 6 ) alkynyl, carboxyl, carboxyl (Ci -C 6 ) alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C3-Cg) -cycloalkylcarbonyl, (Ci-Cg) - alkoxycarbonyl, (Ci-C6) -alkenyloxycarbonyl, (C 2 -cg) - haloalkoxycarbonyl, (C3-Cg) - cycloalkoxycarbonyl, (C2 -cg) -alkylaminocarbonyl, (C3-Cio) dialkylaminocarbonyl, (C3-C 1 0) - cycloalkylaminocarbonyl, (Ci-Cg) alkoxycarbonyl ( C 1 -C 6) -alkyl, (C 2 -Cg) -haloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 9) -cycloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -CG) -alkylaminocarbonyl- C 1 -C 6) -alkyl, (C 3 -C 10) -dialkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 10) -cycloalkylaminocarbonyl- (C 1 -C 6) -alkyl, amino, (C 1 -C 6) -alkylamino , (C 2 -C 10) -dialkylamino, (C 1 -C 6) -haloalkylamino, (C 3 -C 9) -cycloalkylamino, (C 2 -C 6) -alkenylamino, (C 4 -C 10) -dialkenylamino, (C 1 -C 6) -alkylcarbonylamino, ( C2-Cio) - (Dia alkylcarbonyl) amino, (C 1 -C 6 ) -haloalkylcarbonylamino, (C 3 -C 9) -cycloalkylcarbonylamino, (N- (C 1 -C 6 ) -alkylcarbonyl) - (C 1 -C 6 ) -alkylamino, (C 1 -C 6 ) -alkyl- S (0) x stands,
wobei x gleich 0, 1 oder 2 ist, oder  where x is 0, 1 or 2, or
R1 und R2 zusammen einen Alkyl-(CH2)m-Ring bilden, wobei m gleich 3, 4 oder 5 ist, R 1 and R 2 together form an alkyl (CH 2 ) m ring where m is 3, 4 or 5,
R3 und R4 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-Cg)-Alkyl, (Ci-Cg)- Haloalkyl, (C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkoxy-(Ci-C6)-alkyl, (Ci-Cg)-Alkylthio-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylsulfmyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylsulfonyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)-Haloalkylcarbonyl, (C3-Cg)-Cycloalkylcarbonyl, (Ci-Cg)-Alkoxycarbonyl, (C2-Cg)- Haloalkoxycarbonyl, (C4-Cg)- Cycloalkoxycarbonyl, (C2-Cg)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-Cg)-Alkoxy, (Ci-Cg)-Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-Cg)- Cycloalkylthio, stehen, oder R 3 and R 4 are each independently hydrogen, hydroxy, halogen, (Ci-Cg) alkyl, (Ci-Cg) - haloalkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (Ci -C 6) alkoxy- (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy (Ci-C 6) alkyl, (Ci-Cg) alkylthio (Ci-Cg) alkyl, (Ci-Cg) -alkylsulfmyl (Ci-Cg) -alkyl, (Ci-Cg) -alkylsulfonyl- (Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C3 -Cg) -cycloalkylcarbonyl, (Ci-Cg) -alkoxycarbonyl, (C 2 -Cg) - haloalkoxycarbonyl, (C4-Cg) - cycloalkoxycarbonyl, (C 2 -Cg) -alkylaminocarbonyl, (C 3 -C 10) -dialkylaminocarbonyl, (C3 -C 1 0) - Cycloalkylaminocarbonyl, (Ci-Cg) -alkoxy, (Ci-Cg) -alkylthio, (Ci-Cg) -haloalkylthio, (C 3 -Cg) -cycloalkylthio, or
R3 und R4 zusammen einen 3- bis 6-gliedrigen carbocyclischen Ring oder einen 3- bis 6-gliedrigen gesättigten heterocyclischen Ring mit bis zu 2 Sauerstoffatomen bilden, R 3 and R 4 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms,
oder or
R3 und R4 zusammen einen (Ci-C3)-Alkylidenrest oder (Ci-C3)-Haloalkylidenrest bilden, R 3 and R 4 together form a (C 1 -C 3 ) -alkylidene radical or (C 1 -C 3) -haloalkylidene radical,
R5 für Wasserstoff, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)- Halocycloalkyl-(Ci-C6)-alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfinyl- (Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)- Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Formyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-C10)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl steht, R 5 represents hydrogen, (Ci-C 8) -alkyl, (Ci-C8) haloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) - Halocycloalkyl- (Ci-C 6) - alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) haloalkoxy ( C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfinyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) alkylsulfonyl (Ci-C 8) alkyl, (Ci-C 8) alkylcarbonyl, (Ci-C 8) - haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, formyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C4-C8) -cycloalkoxycarbonyl, (C 2 -C 8) -alkylaminocarbonyl, (C3-C 1 0) - alkylaminocarbonyl, (C3-Cio) cycloalkylaminocarbonyl group,
R6 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (C2-C8)- Alkenyl, (C2-C8)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C5)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)- Alkylsulfmyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy, (Ci-Cg)- Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)- Alkylsulfmyl, (Ci-C8)-Haloalkylsulfinyl, (C3-C8)-Cycloalkylsulfmyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-C8)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, R 6 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) - alkenyl, (C 2 -C 8) alkynyl , (C 2 -C 4) haloalkenyl, (C 2 -C 5) haloalkynyl, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, (Ci-C 4) haloalkoxy (C -C 4) alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, (Ci-C 8) - Alkylsulfmyl- (Ci-C 8) alkyl, (Ci-C 8) - Alkylsulfonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -haloalkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, carboxyl, (C 1 -C 8 ) -alkoxycarbonyl, ( C 2 -C 8 ) - haloalkoxycarbonyl, (C 4 -C 8 ) -cycloalkoxycarbonyl, (C 2 -C 8 ) -alkylaminocarbonyl, (C 3 -C 10) -dialkylaminocarbonyl, (C 3 -C 10) -cycloalkylaminocarbonyl, (C 1 -C 8 ) -Alkoxy, (Ci-Cg) - haloalkoxy, (Ci-C 8 ) -alkylthio, (Ci-C 8 ) -haloalkylthio, (C 3 -C 8 ) -cycloalkylthio, (Ci-C 8 ) -alkylsulfmyl, ( Ci-C8) haloalkylsulfinyl, (C 3 -C 8) -Cycloalkylsulfmyl, (Ci-C8) alkylsulfonyl, (Ci-C 8) haloalkylsulfonyl, (C3-C8) cycloalkylsulfonyl, (Ci-C 8 ) -Alkylaminosulfonyl, (C 2 -C 8 ) -dialkylaminosulf is onyl or (C 3 -C 8 ) -trialkylsilyl,
R8 für Wasserstoff, Amino, Hydroxy, Cyano, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-Cg)- Cyanoalkyl, (Ci-C8)-Hydroxyalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, R 8 is hydrogen, amino, hydroxy, cyano, formyl, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (Ci-Cg) - cyanoalkyl, (Ci-C8) hydroxyalkyl, (C -C 8) alkoxy- (Ci-C 8) alkyl, aryl (Ci-C8) alkyl,
Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Cycloalkyl- (Ci-C8)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)-Halocycloalkyl-(Ci-C8)-alkyl, (Ci-C8)- Alkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, Tris-[(Ci-C8)- alkyl]silyl-(C2-C8)-alkinyl, Tris-[(Ci-C8)-alkyl]silyl steht. R9, R10, R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, Formyl,Heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -cycloalkyl- (C 1 -C 8 ) -alkyl, ( C 3 -C 8) halocycloalkyl, (C 3 -C 8) -Halocycloalkyl- (Ci-C 8) alkyl, (Ci-C 8) - alkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 2 - C 8) alkenyl, (C 2 -C 8) -alkynyl, tris - [(Ci-C 8) - alkyl] silyl (C 2 -C 8) -alkynyl, tris - [(Ci-C 8) - alkyl] silyl. R 9 , R 10 , R 11 and R 12 independently of one another represent hydrogen, halogen, cyano, nitro, formyl,
(Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (C2-C8)-Alkenyl, (C2-C4)-Haloalkenyl, (C2-C5)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)- alkyl, (Ci-C8)-Alkylsulfmyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-Cs)- Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)- Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)- Alkylsulfmyl, (Ci-C8)-Haloalkylsulfmyl, (C3-C8)-Cycloalkylsulfmyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-C8)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, (Ci-C 8) -alkyl, (Ci-C8) -haloalkyl, (C 2 -C 8) -alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 5) haloalkynyl, (C -C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (Ci-C8) alkylthio (Ci-C8) - alkyl, (C 1 -C 8 ) -alkylsulfmyl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, C 8 ) -haloalkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, carboxyl, (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) -haloalkoxycarbonyl, (C 4 -C 8 ) -cycloalkoxycarbonyl, (C 2 -C 8) - alkylaminocarbonyl, (C3-Cio) dialkylaminocarbonyl, (C3-Cio) cycloalkylaminocarbonyl, (Ci-C 8) alkoxy, (Ci-C8) alkylthio, (Ci-C8) haloalkylthio, (C 3 -C 8) -cycloalkylthio, (Ci-C 8) - Alkylsulfmyl, (Ci-C 8) -Haloalkylsulfmyl, (C 3 -C 8) -Cycloalkylsulfmyl, (Ci-C8) alkylsulfonyl, (Ci-C 8 ) haloalkylsulfonyl, (C3-C8) cycloalkylsulfonyl, (Ci-C 8) alkylaminosulfonyl, (C 2 -C 8) - dialkylaminosulphonyl or (C3-C 8) is trialkylsilyl,
Besonders bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin A für Sauerstoff, Schwefel, -C(R3)(R4) -, -NR5- oder eine einfache Bindung steht, A particularly preferred subject of the invention are compounds of the general formula (I) in which A is oxygen, sulfur, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond,
Q1 für ein gegebenenfalls substituiertes Aryl oder Heteroaryl steht, wobei jeder Ring optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist, Q 1 is an optionally substituted aryl or heteroaryl, each ring optionally substituted with up to 5 substituents from the group R 6 ,
und wobei für den Fall, dass A eine einfache Bindung ist, der Rest Q1 ungleich Imidazol oder 1 ,2,4-Triazol ist; and in the case where A is a single bond, the radical Q 1 is other than imidazole or 1, 2,4-triazole;
Q2 für die in der oben stehenden Tabelle spezifisch genannten Gruppierungen Q-l bis Q-4 steht, Q 2 stands for the groupings Ql to Q-4 specifically mentioned in the table above,
R1 für Wasserstoff, (Ci-C3)-Alkyl, (Ci-C3)-Haloalkyl, (Ci-C3)-Cyanoalkyl, (Ci-C4)-Alkoxy-(Ci- C3)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C3)-alkyl, (Ci-C4)-Alkylthio-(Ci-C3)-alkyl, (Ci-C4)- Alkylsulfmyl-(Ci-C3)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C3)-alkyl, (Ci-C6)-Cycloalkylthio-(Ci- C3)-alkyl, (Ci-C6)-Cycloalkylsulfmyl-(Ci-C3)-alkyl, (Ci-C6)-Cycloalkylsulfonyl-(Ci-C3)-alkyl, Aryl-(Ci-C3)-alkyl, Heteroaryl-(Ci-C3)-alkyl, Heterocyclyl-(Ci-C3)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C3)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Haloalkenyl, (Ci-C4)- Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, (Ci-Ce)- Alkoxycarbonyl, (C2-C6)-Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (C2-Ce)- Alkylaminocarbonyl, (C3-C6)-Dialkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, (Ci-C6)-Alkoxycarbonyl-(Ci-C3)-alkyl, (C2-C6)-Alkylammocarbonyl-(Ci-C3)-alkyl, (C3-C8)- Dialkylaminocarbonyl-(Ci-C3)-alkyl, (Ci-C6)-Alkylcarbonyloxy-(Ci-C3)-alkyl, (Ci-Ce)- Alkoxycarbonyloxy-(Ci-C3)-alkyl, (C3-C6)-Cycloalkoxycarbonyloxy-(Ci-C3)-alkyl, (Ci-C4)- Alkylsulfonyl, (Ci-C4)-Haloalkylsulfonyl, Arylsulfonyl, Phthalimidomethyl steht, R 1 is hydrogen, (C 1 -C 3 ) -alkyl, (C 1 -C 3 ) -haloalkyl, (C 1 -C 3 ) -cyanoalkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 3 ) -alkyl, (Ci-C 4) haloalkoxy (Ci-C 3) alkyl, (Ci-C 4) alkylthio (Ci-C 3) alkyl, (Ci-C4) - Alkylsulfmyl- (Ci-C 3 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl- (C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -cycloalkylthio (C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -cycloalkylsulfmyl ( C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -cycloalkylsulfonyl- (C 1 -C 3 ) -alkyl, aryl- (C 1 -C 3 ) -alkyl, heteroaryl- (C 1 -C 3 ) -alkyl, heterocyclyl- (C 1 -C 3 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 3 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6) haloalkenyl, (Ci-C4) - alkylcarbonyl, (Ci-C4) haloalkylcarbonyl, (C 3 -C 6) cycloalkylcarbonyl, (Ci-Ce) - alkoxycarbonyl, (C 2 -C 6) - Haloalkoxycarbonyl, (C 3 -C 6) -cycloalkoxycarbonyl, (C 2 -C 6) -alkylaminocarbonyl, (C 3 -C 6 ) -dialkylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -cycloalkylaminocarbonyl, C 3 ) -alkyl, (C 2 -C 6 ) -alkylammocarbonyl- (C 1 -C 3 ) -alkyl, (C 3 -C 8 ) -dialkylaminocarbonyl- (C 1 -C 3 ) - alkyl, (C 1 -C 6) -alkylcarbonyloxy- (C 1 -C 3 ) -alkyl, (C 1 -C 6) - Alkoxycarbonyloxy- (C 1 -C 3) -alkyl, (C 3 -C 6) -cycloalkoxycarbonyloxy- (C 1 -C 3) -alkyl, (C 1 -C 4 ) -alkylsulfonyl, (C 1 -C 4 ) -haloalkylsulfonyl, arylsulfonyl, phthalimidomethyl,
R2 für Wasserstoff, Halogen, Cyano, (Ci-Cs)-Alkyl, (Ci-C5)-Haloalkyl, (Ci-C5)-Cyanoalkyl, (Ci- C5)-Hydroxyalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkoxy-(Ci-C5)-alkyl, (C1-C4)- Haloalkoxy-(Ci-C5)-alkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl, Heterocyclyl-(Ci-C4)- alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C5)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)- Halocycloalkyl-(Ci-C5)-alkyl, (C2-C5)-Alkenyl, (C2-C5)-Alkinyl, (C2-C5)-Haloalkenyl, (C2-C5)- Haloalkinyl, Tris-[(Ci-C6)-alkyl]silyl-(C2-C5)-alkinyl, Carboxyl, Carboxyl-(Ci-C5)-alkyl, (Ci-C6)-Alkylcarbonyl, (Ci-C6)-Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, (Ci-Ce)- Alkoxycarbonyl, (Ci-C6)-Alkenyloxycarbonyl, (C2-C6)-Haloalkoxycarbonyl, (C3-C6)- Cycloalkoxycarbonyl, (Ci-C6)-Alkoxycarbonyl-(Ci-C5)-alkyl, (C2-C6)-Haloalkoxycarbonyl-(Ci- C5)-alkyl, (C3-C6)-Cycloalkoxycarbonyl-(Ci-C5)-alkyl, Amino, (Ci-C5)-Alkylamino, (d-Ce)- Dialkylamino, (Ci-C5)-Haloalkylamino, (C2-C8)-Cycloalkylamino, (C2-C5)-Alkenylamino, (C4- C8)-Dialkenylamino, (Ci-C5)-Alkylcarbonylamino, (C2-C8)-(Dialkylcarbonyl)amino, (C1-C5)- Haloalkylcarbonylamino, (C2-C8)-Cycloalkylcarbonylamino, (N-(Ci-C5)-Alkylcarbonyl)-(Ci- C5)-alkylamino, (Ci-C5)-Alkyl-S(0)x steht, und wobei x gleich 0, 1 oder 2 ist, oder R 2 is hydrogen, halogen, cyano, (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -haloalkyl, (C 1 -C 5 ) -cyanoalkyl, (C 1 -C 5 ) -hydroxyalkyl, (C 1 -C 4 ) Alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkoxy- (C 1 -C 5 ) -alkyl, (C 1 -C 4 ) -haloalkoxy- (C 1 -C 5 ) -alkyl, aryl- Ci-C 4) alkyl, heteroaryl (Ci-C 4) alkyl, heterocyclyl (Ci-C4) - alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) -cycloalkyl- ( Ci-C 5) alkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) - Halocycloalkyl- (Ci-C 5) alkyl, (C 2 -C 5) -alkenyl, (C 2 -C 5) -alkynyl, (C 2 -C 5) haloalkenyl, (C2-C5) - haloalkynyl, tris - [(Ci-C6) alkyl] (C silyl- 2 -C 5) -alkynyl, carboxyl , (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylcarbonyl, (C 1 -C 6) -haloalkylcarbonyl, (C 3 -C 6) -cycloalkylcarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) - Alkenyloxycarbonyl, (C 2 -C 6) -haloalkoxycarbonyl, (C 3 -C 6) -cycloalkoxycarbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 5 ) -alkyl, (C 2 -C 6) -haloalkoxycarbonyl- (C 1 -C 5 ) -alkyl, (C3-C6) -cycloalkoxycarbonyl- (Ci-C 5 ) -alkyl, amino, (Ci-C 5 ) -alkylamino, (d-Ce) - dialkylamino, (Ci-C5 ) -Haloalkylamino, (C 2 -C 8) -cycloalkylamino, (C 2 -C 5) -alkenylamino, (C 4 -C 8) -dialkenylamino, (C 1 -C 5) -alkylcarbonylamino, (C 2 -C 8) - (dialkylcarbonyl) -amino, (Cl -C5) - haloalkylcarbonylamino, (C2-C8) -cycloalkylcarbonylamino, (N- (Ci-C5) -alkylcarbonyl) - (Ci- C5) -alkylamino, (Ci-C5) -alkyl-S (0) x , and where x is 0, 1 or 2, or
R1 und R2 gemeinsam einen Alkyl-(CH2)m-Ring bilden, wobei m gleich 3, 4 oder 5 ist, R 1 and R 2 together form an alkyl (CH 2 ) m ring, where m is 3, 4 or 5,
R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl stehen, R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl,
R5 für Wasserstoff, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, Aryl-(Ci-C3)-alkyl, Heteroaryl-(Ci-C3)-alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Formyl, (Ci-C4)-Alkoxycarbonyl, (C2-C4)-Haloalkoxycarbonyl, (C2-C4)-Alkylaminocarbonyl, (C3-C6)- Dialkylaminocarbonyl steht, R 5 represents hydrogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, aryl (Ci-C 3) alkyl, heteroaryl (Ci-C 3) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (Ci-C 4) alkylcarbonyl, (Ci-C4) haloalkylcarbonyl, formyl, (Ci-C4) alkoxycarbonyl, (C 2 -C 4) - Haloalkoxycarbonyl, (C 2 -C 4) -alkylaminocarbonyl, (C 3 -C 6) -dialkylaminocarbonyl,
R6 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C8)-Alkyl, (Ci-C4)-Haloalkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (C1-C4)- Alkylsulfmyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Haloalkylthio, (C3-C6)-Cycloalkylthio, (Ci-C4)-Alkylsulfmyl, (Ci-C4)-Haloalkylsulfmyl, (C3-C6)-Cycloalkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (C1-C4)- Haloalkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (Ci-C4)-Alkylaminosulfonyl, (C2-C4)- Dialkylaminosulfonyl oder (C3-C6)-Trialkylsilyl steht, und R 6 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 8) -alkyl, (Ci-C 4) -haloalkyl, (C2-C4) - alkenyl, (C 2 -C 4) -alkynyl, ( C 2 -C 4) haloalkenyl, (C 2 -C 4) haloalkynyl, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (Ci-C 4) alkylthio (Ci-C 4) alkyl, (C1-C4) - Alkylsulfmyl- (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl ( C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -haloalkylcarbonyl, (C 3 -C 6) -cycloalkylcarbonyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) - haloalkoxy, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (C 3 -C 6) -cycloalkylthio, (Ci-C 4) -Alkylsulfmyl, (Ci-C 4) -Haloalkylsulfmyl, (C3 -C 6 ) -cycloalkylsulfinyl, (C 1 -C 4 ) -alkylsulfonyl, (C 1 -C 4) - Haloalkylsulfonyl, (C 3 -C 6) -cycloalkylsulfonyl, (C 1 -C 4) -alkylaminosulfonyl, (C 2 -C 4) -dialkylaminosulfonyl or (C 3 -C 6) -trialkylsilyl, and
R9, R10, R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, Cyano, (Ci-C4)-Alkyl, R 9 , R 10 , R 11 and R 12 independently of one another represent hydrogen, halogen, cyano, (C 1 -C 4) -alkyl,
(Ci- C4)-Haloalkyl, (Ci-C3)-Alkoxy, (Ci-C3)-Haloalkoxy steht. (C 1 -C 4 ) -haloalkyl, (C 1 -C 3 ) -alkoxy, (C 1 -C 3 ) -haloalkoxy.
Ebenfalls weiter bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Also further preferred subject of the invention are compounds of the general formula (I) wherein
A für Sauerstoff, Schwefel, -C(R3)(R4) -, -NR5- oder eine einfache Bindung steht, A is oxygen, sulfur, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond,
Q1 für ein gegebnenfalls substituiertes Aryl oder Heteroaryl steht, wobei jeder Ring optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist, Q 1 is an optionally substituted aryl or heteroaryl, each ring optionally substituted with up to 5 substituents from the group R 6 ,
und wobei für den Fall, dass A eine einfache Bindung ist, der Rest Q1 ungleich Imidazol oder 1 ,2,4-Triazol ist, für die Gruppen Q-11 bis Q-14 steht; and wherein in the case where A is a single bond, the group Q 1 is other than imidazole or 1, 2,4-triazole, groups Q-11 to Q-14;
Q-11 Q-12 Q-13 Q-14 Q-11 Q-12 Q-13 Q-14
R1 für Wasserstoff, Methyl, Ethyl, Isopropyl, (Ci-C2)-Haloalkyl, Cyanomethyl, (Ci-C4)-Alkoxy- (Ci-C2)-alkyl, (Ci-C4)-Alkylthio-(Ci-C2)-alkyl, (Ci-C4)-Alkylsulfmyl-(Ci-C2)-alkyl, (C1-C4)- Alkylsulfonyl-(Ci-C2)-alkyl, Arylmethyl, (C2-C6)-Alkenyl, (Ci-C6)-Alkoxycarbonyl, (C3-C6)- Cycloalkoxycarbonyl, (Ci-C6)-Alkoxycarbonyloxy-(Ci-C2)-alkyl, (Ci-C6)-Alkylcarbonyloxy- (Ci-C2)-alkyl steht, R 1 is hydrogen, methyl, ethyl, isopropyl, (C 1 -C 2 ) -haloalkyl, cyanomethyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 2 ) -alkyl, (C 1 -C 4 ) -alkylthio ( Ci-C 2) alkyl, (Ci-C 4) -Alkylsulfmyl- (Ci-C 2) alkyl, (C 1 -C 4) - alkylsulfonyl (Ci-C 2) alkyl, arylmethyl, (C 2 - C 6) alkenyl, (Ci-C 6) -alkoxycarbonyl, (C 3 -C 6) - cycloalkoxycarbonyl, (Ci-C6) alkoxycarbonyloxy (Ci-C 2) alkyl, (Ci-C6) alkylcarbonyloxy (C 1 -C 2 ) -alkyl,
R für Wasserstoff, Halogen, Cyano, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Cyanoalkyl, (Ci- C4)-Hydroxyalkyl, (Ci-C3)-Alkoxy-(Ci-C4)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci- C4)-alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, (Ci-C6)- Alkoxycarbonyl, (Ci-C6)-Alkenyloxycarbonyl, (C2-C6)-Haloalkoxycarbonyl, (CI-CÖ)- Alkoxycarbonyl-(Ci-C4)-alkyl, (C2-C6)-Haloalkoxycarbonyl-(Ci-C4)-alkyl, Amino, (C1-C4)- Alkylamino, (C2-C6)-Dialkylamino, (C2-C4)-Alkenylamino, (Ci-C4)-Alkylcarbonylamino steht, oder R is hydrogen, halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -cyanoalkyl, (C 1 -C 4 ) -hydroxyalkyl, (C 1 -C 3 ) alkoxy (Ci-C 4) alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci C 4) alkyl, (C 2 -C 4) alkenyl , (C 2 -C 4) -alkynyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) haloalkynyl, (Ci-C6) - alkoxycarbonyl, (Ci-C 6) alkenyloxycarbonyl, ( C 2 -C 6) -haloalkoxycarbonyl, (CI-C Ö ) - Alkoxycarbonyl- (C 1 -C 4) -alkyl, (C 2 -C 6) -haloalkoxycarbonyl- (C 1 -C 4) -alkyl, amino, (C 1 -C 4) -alkylamino, (C 2 -C 6) -dialkylamino, (C 2 -C 4) ) Alkenylamino, (C 1 -C 4) -alkylcarbonylamino, or
R1 und R2 gemeinsam einen Alkyl-(CH2)m-ring bilden, wobei m gleich 3 oder 4 ist, R 1 and R 2 together form an alkyl (CH 2 ) m ring, where m is 3 or 4,
R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, Methyl oder Ethyl steht, R5 für Wasserstoff, Methyl, Ethyl, Formyl oder Acetyl steht, R 3 and R 4 independently of one another are hydrogen, halogen, methyl or ethyl, R 5 is hydrogen, methyl, ethyl, formyl or acetyl,
R6 für Wasserstoff, Halogen, Cyano, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C3)-Alkoxy, (C1-C3)- Haloalkoxy, Methyl-S(0)n steht, wobei n gleich 0, 1 oder 2 ist, R10 für Wasserstoff, Halogen, Cyano, Methyl, Trifluormethyl, Methoxy steht. R 6 is hydrogen, halogen, cyano, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C 3) alkoxy, (C1-C3) - haloalkoxy, methyl-S (0) n , where n is 0, 1 or 2, R 10 is hydrogen, halogen, cyano, methyl, trifluoromethyl, methoxy.
Äußerst bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin A für Sauerstoff, Schwefel, -CH2-, -NR5- oder eine einfache Bindung steht, An extremely preferred subject of the invention are compounds of the general formula (I) in which A represents oxygen, sulfur, -CH 2 -, -NR 5 - or a simple bond,
Q1 für ein gegebnenfalls substituiertes Aryl oder Heteroaryl steht, wobei jeder Ring optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist; und wobei für den Fall, dass A eine einfache Bindung ist, der Rest Q1 ungleich Imidazol oder 1 ,2,4-Triazol ist; Q 1 is an optionally substituted aryl or heteroaryl, each ring optionally substituted with up to 5 substituents from the group R 6 ; and in the case where A is a single bond, the radical Q 1 is other than imidazole or 1, 2,4-triazole;
Q2 für die Gruppen Q- 11 bis Q- 13 steht Q 2 stands for groups Q-11 to Q-13
Q-l l Q-12 Q-13 Q-1 Q-12 Q-13
R1 für Wasserstoff, Methyl, Ethyl, Isopropyl, Difluormethyl, 2-Methoxyethyl, 2-Methylsulfanylethyl, Benzyl, Vinyl, Allyl, tert-Butoxycarbonyl steht, R für Wasserstoff, Cyano, Methyl, Ethyl, Propyl, Trifluormethyl, Cyanomethyl, Cyclopropyl, Methoxycarbonyl, Ethoxycarbonyl, Methoxycarbonylmethyl, Amino, Acetylaminosteht, oder R1 und R2 gemeinsam einen Alkyl-(CH2)3-ring bilden, R5 für Wasserstoff oder Methyl steht, R 1 is hydrogen, methyl, ethyl, isopropyl, difluoromethyl, 2-methoxyethyl, 2-methylsulfanylethyl, benzyl, vinyl, allyl, tert-butoxycarbonyl, R is hydrogen, cyano, methyl, ethyl, propyl, trifluoromethyl, cyanomethyl, cyclopropyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, amino, acetylamino, or R 1 and R 2 together form an alkyl (CH 2 ) 3 ring, R 5 is Is hydrogen or methyl,
R6 für Wasserstoff, Fluor, Chlor, Cyano, Methyl, Trifluormethyl, Methoxy, Trifluormethoxy steht, R 6 represents hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy,
R10 für Wasserstoff, Fluor, Chlor, Cyano, Methyl, Trifluormethyl, Methoxy steht. R 10 is hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der allgemeinenFormel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Zwischenprodukte. Diese Restedefinitionen können The general or preferred radical definitions given above apply both to the end products of the general formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These remainder definitions can
untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden. among each other, so also between the specified preferred ranges are arbitrarily combined.
Vor allem aus den Gründen der höheren herbiziden Wirkung, besseren Selektivität und/oder besseren Herstellbarkeit sind erfindungsgemäße Verbindungen der genannten allgemeinen Formel (I) oder deren Salze bzw. deren erfindungsgemäße Verwendung von besonderem Interesse, worin einzelne Reste eine der bereits genannten oder im folgenden genannten bevorzugten Bedeutungen haben, oder insbesondere solche, worin eine oder mehrere der bereits genannten oder im Folgenden genannten bevorzugten Bedeutungen kombiniert auftreten. Im Hinblick auf die erfindungsgemäßen Verbindungen werden die vorstehend und weiter unten verwendeten Bezeichnungen erläutert. Diese sind dem Fachmann geläufig und haben insbesondere die im Folgenden erläuterten Bedeutungen: Above all, for reasons of higher herbicidal activity, better selectivity and / or better manufacturability, compounds of the general formula (I) according to the invention or their salts or their use according to the invention are of particular interest, in which individual radicals are one of those already mentioned or mentioned below have preferred meanings, or in particular those in which one or more of the already mentioned or mentioned below preferred meanings occur in combination. With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and in particular have the meanings explained below:
Sofern nicht anders definiert, gilt generell für die Bezeichnung von chemischen Gruppen, dass die Anbindung an das Gerüst bzw. den Rest des Moleküls über das zuletzt genannte Strukturelement der betreffenden chemischen Gruppe erfolgt, d.h. beispielsweise im Falle von (C2-Cg)-Alkenyloxy über das Sauerstoffatom, und im Falle von Heterocyclyl-(Ci-Cg)-alkyl oder R120(0)C-(Ci-Cg)-Alkyl jeweils über das C-Atom der Alkylgruppe. Erfindungsgemäß steht "Alkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Unless otherwise defined, generally applies to the designation of chemical groups that the attachment to the skeleton or the rest of the molecule via the last-mentioned structural element of the chemical group in question, ie, for example, in the case of (C2-Cg) alkenyloxy over the oxygen atom, and in the case of heterocyclyl (Ci-Cg) alkyl or R 12 0 (0) C (Ci-Cg) alkyl in each case via the C atom of the alkyl group. According to the invention "alkylsulfonyl" - alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, z.B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfonyl wie Methylsulfonyl, Ethyl- sulfonyl, Propylsulfonyl, 1 -Methylethylsulfonyl, Butylsulfonyl, 1 -Methylpropylsulfonyl, 2-Methyl- propylsulfonyl, 1 , 1 -Dimethylethylsulfonyl, Pentylsulfonyl, 1 -Methylbutylsulfonyl, 2-Methylbutyl- sulfonyl, 3 -Methylbutylsulfonyl, 1 ,1 -Dimethylpropylsulfonyl, 1 ,2-Dimethylpropylsulfonyl, 2,2-Di- methylpropylsulfonyl, 1 -Ethylpropylsulfonyl, Hexylsulfonyl, 1 -Methylpentylsulfonyl, 2-Methyl- pentylsulfonyl, 3 -Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1 ,1 -Dimethylbutylsulfonyl, 1 ,2-Di- methylbutylsulfonyl, 1 ,3 -Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3 ,3 -Dimethylbutylsulfonyl, 1 -Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1 , 1 ,2-Trimethylpropylsulfonyl, 1 ,2,2-Trimethylpropylsulfonyl, 1 -Ethyl- 1 -methylpropylsulfonyl und 1 -Ethyl-2-methylpropylsulfonyl. Erfindungsgemäß steht "Heteroarylsulfonyl" für gegebenenfalls substituiertes Pyridylsulfonyl, Carbon atoms, eg (but not limited to) (C 1 -C 6) alkylsulfonyl such as methylsulfonyl, ethyl sulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1, 1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1 - Ethyl 1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl. According to the invention "heteroarylsulfonyl" is optionally substituted pyridylsulfonyl,
Pyrimidinylsulfonyl, Pyrazinylsulfonyl oder gegebenenfalls substituiertes polycyclisches Pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally substituted polycyclic
Heteroarylsulfonyl, hier insbesondere gegebenenfalls substituiertes Chinolinylsulfonyl, beispielsweise substituiert durch Fluor, Chlor, Brom, Iod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, Alkylamino-, Alkylcarbonylamino-, Dialkylamino- oder Alkoxygruppen. 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.
Erfindungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention "alkylthio" - alone or as part of a chemical group - is straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie (Ci-Cio)-, (CI-CÖ)- oder (Ci-C4)-Alkylthio, z.B. (aber nicht beschränkt auf) (Ci- Ce)-Alkylthio wie Methylthio, Ethylthio, Propylthio, 1 -Methylethylthio, Butylthio, 1 -Methylpropylthio, 2-Methylpropylthio, 1 , 1 -Dimethylethylthio, Pentylthio, 1 -Methylbutylthio, 2-Methylbutylthio, 3 - Methylbutylthio, 1 ,1 -Dimethylpropylthio, 1 ,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1 - Ethylpropylthio, Hexylthio, 1 -Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl- pentylthio, 1 ,1 -Dimethylbutylthio, 1 ,2-Dimethylbutylthio, 1 ,3-Dimethylbutylthio, 2,2-Dimethylbutyl- thio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1 -Ethylbutylthio, 2-Ethylbutylthio, 1 , 1 ,2-Tri- methylpropylthio, 1 ,2,2-Trimethylpropylthio, 1 -Ethyl- 1 -methylpropylthio und 1 -Ethyl-2-methyl- propylthio. Carbon atoms, such as (Ci-Cio) -, (CI-CÖ) - or (Ci-C4) -alkylthio, e.g. (but not limited to) (ce-Ce) -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1 Dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 1, 2-tri methylpropylthio, 1, 2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.
„Alkenylthio" bedeutet erfindungsgemäßt ein über ein Schwefelatom gebundenen Alkenylrest, "Alkenylthio" in the invention means an alkenyl radical bonded via a sulfur atom,
Alkinylthio bedeutet ein über ein Schwefelatom gebundenen Alkinylrest, Cycloalkylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkylrest und Cycloalkenylthio bedeutet ein über ein Alkynylthio represents an alkynyl group bonded through a sulfur atom, cycloalkylthio represents a cycloalkyl group bonded through a sulfur atom, and cycloalkenylthio represents an above
Schwefelatom gebundenen Cycloalkenylrest. Sulfur atom bonded cycloalkenyl radical.
„Alkylsulfinyl (Alkyl-S(=0)-)", soweit nicht an anderer Stelle anders definiert steht erfindungsgemäß für Alkylreste, die über -S(=0)- an das Gerüst gebunden sind, wie (Ci-Cio)-, (CI-CÖ)- oder (C1-C4)- Alkylsulfinyl, z. B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfinyl wie Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1 -Methylethylsulfinyl, Butylsulfinyl, 1 -Methylpropylsulfinyl, 2-Methylpropylsulfinyl, 1 , 1 -Dimethylethylsulfinyl, Pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3- Methylbutylsulfinyl, 1 ,1 -Dimethylpropylsulfmyl, 1 ,2-Dimethylpropylsulfinyl, 2,2-Di- methylpropylsulfinyl, 1 -Ethylpropylsulfinyl, Hexylsulfinyl, 1 -Methylpentylsulfinyl, 2-Methylpentyl- sulfinyl, 3 -Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1 ,1 -Dimethylbutylsulfinyl, 1 ,2-Dimethyl- butylsulfmyl, 1 ,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3- Dimethylbutylsulfmyl, 1 -Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1 ,1 ,2-Trimethylpropylsulfinyl, 1 ,2,2- Trimethylpropylsulfinyl, l -Ethyl-l -methylpropylsulfinyl und l -Ethyl-2-methylpropylsulfinyl. "Alkylsulfinyl (alkyl-S (= 0) -)", unless otherwise defined elsewhere, according to the invention for alkyl radicals which are bonded to the skeleton via -S (= O) -, such as (C 1 -C 10) -, ( CI-CÖ) - or (C 1 -C 4) -alkylsulfinyl, for example (but not limited to) (C 1 -C 6) -alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2- Methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3 Methylbutylsulfinyl, 1, 1-dimethylpropylsulfmyl, 1, 2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1, 1 Dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfmyl, 1, 3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfmyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1, 1, 2-trimethylpropylsulfinyl, 1, 2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.
Analog sind„Alkenylsulfinyl" und„Alkinylsulfinyl", erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)- Alkenylsulfinyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinylsulfmyl. Analogously, "alkenylsulfinyl" and "alkynylsulfinyl" are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via -S (= O) -, such as (C 2 -C 10) -, (C 2 -C 6) - or ( C 2 -C 4 ) - alkenylsulfinyl or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C 4 ) -alkynylsulfinyl.
Analog sind„Alkenylsulfonyl" und„Alkinylsulfonyl" erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=0)2- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)- Alkenylsulfonyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinylsulfonyl. Analogously, "alkenylsulfonyl" and "alkynylsulfonyl" are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via -S (= O) 2-, such as (C 2 -C 10) -, (C 2 -C 6) - or ( C2-C4) - alkenylsulfonyl or (C3-C10) -, (C3-C6) - or (C3-C4) -alkynylsulfonyl.
„Alkoxy" bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B. (aber nicht beschränkt auf) (Ci-Ce)-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1 -Methylethoxy, Butoxy, 1 -Methylpropoxy, 2- Methylpropoxy, 1 ,1 -Dimethylethoxy, Pentoxy, 1 -Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1 , 1 - Dimethylpropoxy, 1 ,2-Dimethylpropoxy, 2,2-Dimethylpropoxy, 1 -Ethylpropoxy, Hexoxy, 1 - Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1 ,1 -Dimethylbutoxy, 1 ,2-Di- methylbutoxy, 1 ,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethylbutoxy, 1 - Ethylbutoxy, 2-Ethylbutoxy, 1 ,1 ,2-Trimethylpropoxy, 1 ,2,2-Trimethylpropoxy, 1 -Ethyl-l -methylpropoxy und 1 -Ethyl-2-methylpropoxy. Alkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkenylrest, Alkinyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkinylrest wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenoxy bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkmoxy. "Alkoxy" means an alkyl radical bonded through an oxygen atom, for example (but not limited to) (C 1 -C 6) alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy , 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy , 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy means an alkenyl radical bonded through an oxygen atom, alkynyloxy means an above an oxygen atom bonded alkynyl group such as (C 2 -C 1 0) -, (C 2 -C 6) - or (C 2 -C 4) alkenoxy, and (C3-C10) -, (C 3 -C 6) - or (C 3 -C 4 ) -alkoxy.
„Cycloalkyloxy" bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylrest und Cycloalkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkenylrest. „Alkylcarbonyl" (Alkyl-C(=0)-), soweit nicht an anderer Stelle anders definiert, steht erfindungsgemäß für Alkylreste, die über -C(=0)- an das Gerüst gebunden sind, wie (C1-C10)-, (Ci-Ce)- oder (C1-C4)- Alkylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der "Cycloalkyloxy" denotes a cycloalkyl radical bonded via an oxygen atom and cycloalkenyloxy denotes a cycloalkenyl radical bonded via an oxygen atom. "Alkylcarbonyl" (alkylC (= O) -), unless otherwise defined elsewhere, is, according to the invention, alkyl radicals which C (= O) - are attached to the skeleton, such as (C 1 -C 10) -, (C 1 -C 6) - or (C 1 -C 4) -alkylcarbonyl. The number of C atoms refers to the alkyl radical in the
Alkylcarbonylgruppe. Analog stehen„Alkenylcarbonyl" und„Alkinylcarbonyl", soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -C(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyl bzw. (C2-C10)-, (C2-C6)- oder (C2-C4)- Alkinylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonylgruppe. Alkylcarbonyl. Analogously, "alkenylcarbonyl" and "alkynylcarbonyl" are, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -C (= O) -, such as (C 2 -C 10) -, ( C2-C6) - or (C2-C4) -alkenylcarbonyl or (C2-C10) -, (C2-C6) - or (C2-C4) - Alkynylcarbonyl. The number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
„Alkoxycarbonyl (Alkyl-0-C(=0)-)", soweit nicht an anderer Stelle anders definiert: Alkylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (Ci-Cio)-, (CI-CÖ)- oder (Ci-C i)-Alkoxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkoxycarbonylgruppe. Analog stehen „Alkenyloxycarbonyl" und„Alkinyloxycarbonyl", soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenyloxycarbonyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)- Alkinyloxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alken- bzw. Alkinyloxycarbonylgruppe. "Alkoxycarbonyl (alkyl-0-C (= 0) -)", unless otherwise defined elsewhere: alkyl radicals attached to the skeleton via -0-C (= 0) - such as (Ci-Cio) - , (CI-CÖ) - or (Ci-C i) -alkoxycarbonyl.The number of carbon atoms refers to the alkyl radical in the alkoxycarbonyl group. Analogously, "alkenyloxycarbonyl" and "alkynyloxycarbonyl", unless otherwise defined elsewhere , according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -O-C (= O) -, such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -C 4 ) alkenyloxycarbonyl or (C3-C10) -, (C 3 -C 6) - or (C3-C4) -. alkynyloxycarbonyl the number of carbon atoms refers to the alkenyl and alkynyl in the alkene or alkynyloxycarbonyl.
Der Begriff„Alkylcarbonyloxy" (Alkyl-C(=0)-0-) steht erfindungsgemäß, soweit nicht an anderer Stelle anders definiert, für Alkylreste, die über eine Carbonyloxygruppe (-C(=0)-0-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C1-C10)-, (CI-CÖ)- oder (Ci-C i)-Alkylcarbonyloxy. Die Anzahl der C- Atome bezieht sich dabei auf den Alkylrest in der Alkylcarbonyloxygruppe.  The term "alkylcarbonyloxy" (alkyl-C (= 0) -O-) is according to the invention, unless otherwise defined elsewhere, for alkyl radicals which have a carbonyloxy group (-C (= O) -O-) with the oxygen the skeleton are bonded, such as (C1-C10) -, (CI-CÖ) - or (Ci-C i) -Alkylcarbonyloxy.The number of carbon atoms refers to the alkyl radical in the alkylcarbonyloxy group.
Analog sind„Alkenylcarbonyloxy" und„Alkinylcarbonyloxy" erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über (-C(=0)-0-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyloxy bzw. (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkinylcarbonyloxy. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonyloxygruppe. Analogously, "alkenylcarbonyloxy" and "alkynylcarbonyloxy" are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via (-C (= O) -O-), such as (C 2 -C 10) -, (C 2 -C 4) -C 6) - or (C 2 -C 4) -alkenylcarbonyloxy or (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4) -alkynylcarbonyloxy. The number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
In Kurzformen wie z.B. C(0)R12, C(0)OR12, OC(O)NR10Ru, oder C(O)NR10Ru steht die in Klammern aufgeführte Kurzform O für ein über eine Doppelbindung an das benachbarte Kohlenstoffatom gebundenes Sauerstoffatom. In short forms such as, for example, C (O) R 12 , C (O) OR 12 , OC (O) NR 10 R u , or C (O) NR 10 R u , the short form O shown in parentheses represents a double bond to the adjacent carbon atom bound oxygen atom.
In Kurzformen wie z.B. OC(S)OR12, OC(S)SR13, OC(S)NR10RU, steht die in Klammern aufgeführte Kurzform S für ein über eine Doppelbindung an das benachbarte Kohlenstoffatom gebundenes In short forms such as, for example, OC (S) OR 12 , OC (S) SR 13 , OC (S) NR 10 R U , the abbreviation S shown in parentheses S stands for a double bond bound to the adjacent carbon atom
Schwefelatom. Sulfur atom.
Der Begriff„Aryl" bedeutet ein gegebenenfalls substituiertes mono-, bi- oder polycyclisches aromatisches System mit vorzugsweise 6 bis 14, insbesondere 6 bis 10 Ring-C- Atomen, beispielsweise Phenyl, Naphthyl, Anthryl, Phenanthrenyl, und ähnliches, vorzugsweise Phenyl. Vom Begriff„gegebenenfalls substituiertes Aryl" sind auch mehrcyclische Systeme, wie The term "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 The term "optionally substituted aryl" are also mehrcyclische systems, such as
Tetrahydronaphtyl, Indenyl, Indanyl, Fluorenyl, Biphenylyl, umfasst, wobei die Bindungsstelle am aromatischen System ist. Von der Systematik her ist„Aryl" in der Regel auch von dem Begriff „gegebenenfalls substituiertes Phenyl" umfasst. Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis-alkylaminoalkoxy, Tris- [alkyljsilyl, Bis- [alkyl] arylsilyl, Bis- [alkyl] alkylsilyl, Tris- [alkyl] silylalkinyl, Arylalkinyl, Tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, wherein the binding site is on the aromatic system. From the systemic point of view, "aryl" is usually also of the term Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio , Haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkylsilyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl ] silylalkynyl, arylalkynyl,
Heteroarylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bis-alkylamino, alkylcarbonylamino, cycloalkylcarbonylamino,
Arylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino,
Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl,
Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy,  Alkylaminocarbonyl, cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
Arylalkoxy arylalkoxy
Ein heterocyclischer Rest (Heterocyclyl) enthält mindestens einen heterocyclischen Ring A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring
(=carbocyclischer Ring, in dem mindestens ein C-Atom durch ein Heteroatom ersetzt ist, vorzugsweise durch ein Heteroatom aus der Gruppe N, O, S, P) der gesättigt, ungesättigt, teilgesättigt oder heteroaromatisch ist und dabei unsubstituiert oder substituiert sein kann, wobei die Bindungsstelle an einem Ringatom lokalisiert ist. Ist der Heterocyclylrest oder der heterocyclische Ring gegebenenfalls substituiert, kann er mit anderen carbocyclischen oder heterocyclischen Ringen annelliert sein. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch mehrcyclische Systeme umfasst, wie beispielsweise 8-Aza-bicyclo[3.2.1]octanyl, 8-Aza-bicyclo[2.2.2]octanyl oder 1-Aza- bicyclo[2.2.1]heptyl. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch (= carbocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom. When the heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclyl also become
spirocyclische Systeme umfasst, wie beispielsweise l-Oxa-5-aza-spiro[2.3]hexyl. Wenn nicht anders definiert, enthält der heterocyclische Ring vorzugsweise 3 bis 9 Ringatome, insbesondere 3 bis 6 Ringatome, und ein oder mehrere, vorzugsweise 1 bis 4, insbesondere 1 , 2 oder 3 Heteroatome im heterocyclischen Ring, vorzugsweise aus der Gruppe N, O, und S, wobei jedoch nicht zwei spiro-cyclic systems such as 1-oxa-5-aza-spiro [2.3] hexyl. Unless defined otherwise, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 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
Sauerstoffatome direkt benachbart sein sollen, wie beispielsweise mit einem Heteroatom aus der Gruppe N, O und S 1- oder 2- oder 3-Pyrrolidinyl, 3,4-Dihydro-2H-pyrrol-2- oder 3-yl, 2,3-Dihydro-lH-pyrrol-Oxygen atoms are to be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2 or 3-yl, 2,3- dihydro-lH-pyrrole
1- oder 2- oder 3- oder 4- oder 5-yl; 2,5-Dihydro-lH-pyrrol-l - oder 2- oder 3-yl, 1- oder 2- oder 3- oder 4-Piperidinyl; 2,3,4,5-Tetrahydropyridin-2- oder 3- oder 4- oder 5-yl oder 6-yl; 1,2,3,6-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1 - or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6
Tetrahydropyridin-1- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,2,3,4-Tetrahydropyridin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,4-Dihydropyridin-l - oder 2- oder 3- oder 4-yl; 2,3-Dihydropyridin-Tetrahydropyridine-1 or 2 or 3 or 4 or 5 or 6-yl; 1,2,3,4-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridine-I - or 2- or 3- or 4-yl; 2,3-dihydropyridine
2- oder 3- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyridin-2- oder 3- oder 4- oder 5- oder 6-yl, 1- oder 2- oder 3- oder 4-Azepanyl; 2,3,4,5-Tetrahydro-lH-azepin-l- oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-lH-azepin-l- oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepine-1 or 2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,4,7-tetrahydro-1H-azepine-1 or 2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,6,7
Tetrahydro-lH-azepin-1- oder 2- oder 3- oder 4-yl; 3,4,5,6-Tetrahydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-lH-azepin-l- oder 2- oder 3- oder 4-yl; 2,5-Dihydro-lH-azepin- 1- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-lH-azepin-l- oder -2- oder 3- oder 4- yl; 2,3-Dihydro-lH-azepin-l - oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,4-Dihydro-2H-azepin-Tetrahydro-1H-azepine-1 or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1H-azepine-1 or 2 or 3 or 4-yl; 2,5-dihydro-lH-azepin- 1- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1H-azepine-1 or -2 or 3 or 4 yl; 2,3-dihydro-1H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 3,4-dihydro-2H-azepine
2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 5,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-3H-azepin- 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 1H-Azepin-1- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl, 2- oder 3-Oxolanyl (= 2- oder 3- Tetrahydrofuranyl); 2,3-Dihydrofüran-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrofüran-2- oder 3-yl, 2- oder 3- oder 4-Oxanyl (= 2- oder 3- oder 4-Tetrahydropyranyl); 3,4-Dihydro-2H-pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-pyran-2- oder 3-oder 4- oder 5- oder 6-yl; 2H-Pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Pyran-2- oder 3- oder 4-yl, 2- oder 3- oder 4-Oxepanyl; 2,3,4,5- Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydrooxepin-2- oder 3- oder2- or 3- or 4- or 5- or 6- or 7-yl; 3,6-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 5,6-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-3H-azepine 2- or 3- or 4- or 5- or 6- or 7-yl; 1H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 3H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-pyran-2 or 3 or 4 or 5 or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,4,7-tetrahydrooxepin-2 or 3 or
4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydrooxepin-2- oder 3- oder 4-yl; 2,3-Dihydrooxepin-2- oder4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydrooxepin-2 or 3 or 4-yl; 2,3-dihydrooxepin-2-or
3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydrooxepin-2- oder 3- oder 4-yl; 2,5-Dihydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; Oxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2- oder 3-3- or 4- or 5- or 6- or 7-yl; 4,5-dihydrooxepin-2 or 3 or 4-yl; 2,5-dihydrooxepin-2 or 3 or 4 or 5 or 6 or 7-yl; Oxepin-2 or 3 or 4 or 5 or 6 or 7-yl; 2- or 3-
Tetrahydrothiophenyl; 2,3-Dihydrothiophen-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrothiophen-2- oder 3-yl; Tetrahydro-2H-thiopyran-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-thiopyran-2- oder 3- oder 4- odertetrahydrothiophenyl; 2,3-dihydrothiophene-2 or 3 or 4 or 5-yl; 2,5-dihydrothiophene-2 or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2 or 3 or 4 or
5- oder 6-yl; 3,6-Dihydro-2H-thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 2H-Thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Thiopyran-2- oder 3- oder 4-yl. Bevorzugte 3-Ring und 4-Ring- Heterocyclen sind beispielsweise 1- oder 2-Aziridinyl, Oxiranyl, Thiiranyl, 1- oder 2- oder 3-Azetidinyl,5- or 6-yl; 3,6-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 4H-thiopyran-2- or 3- or 4-yl. Preferred 3-membered ring and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
2- oder 3-Oxetanyl, 2- oder 3-Thietanyl, l,3-Dioxetan-2-yl. Weitere Beispiele für "Heterocyclyl" sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit zwei Heteroatomen aus der Gruppe N, O und S, wie beispielsweise 1- oder 2- oder 3- oder 4-Pyrazolidinyl; 4,5-Dihydro-3H-pyrazol- 3- oder 4- oder 5-yl; 4,5-Dihydro-lH-pyrazol-l - oder 3- oder 4- oder 5-yl; 2,3-Dihydro-lH-pyrazol-l - oder 2- oder 3- oder 4- oder 5-yl; 1- oder 2- oder 3- oder 4- Imidazolidinyl; 2,3-Dihydro-lH-imidazol-l- oder 2- oder2- 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-I or 2- or
3- oder 4-yl; 2,5-Dihydro-lH-imidazol-l- oder 2- oder 4- oder 5-yl; 4,5-Dihydro-lH-imidazol-l- oder 2- oder 4- oder 5-yl; Hexahydropyridazin-1- oder 2- oder 3- oder 4-yl; 1,2,3,4-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,2,3, 6-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder3- 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 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazine-l- or 2- or 3- or 4- or 5- or
6- yl; 1,4,5, 6-Tetrahydropyridazin-l- oder 3- oder 4- oder 5- oder 6-yl; 3,4,5, 6-Tetrahydropyridazin-3- oder 4- oder 5-yl; 4,5-Dihydropyridazin-3- oder 4-yl; 3,4-Dihydropyridazin-3- oder 4- oder 5- oder 6-yl;6-yl; 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl;
3,6-Dihydropyridazin-3- oder 4-yl; 1,6-Dihydropyriazin-l- oder 3- oder 4- oder 5- oder 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1,6-dihydropyriazine-1- or 3- or 4- or 5- or 6-yl;
Hexahydropyrimidin-1- oder 2- oder 3- oder 4-yl; 1,4,5,6-Tetrahydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1,2,5,6-Tetrahydropyrimidin-l - oder 2- oder 4- oder 5- oder 6-yl; 1,2,3,4- Tetrahydropyrimidin-1- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,6-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1,2-Dihydropyrimidin-l - oder 2- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyrimidin- 2- oder 4- oder 5-yl; 4,5-Dihydropyrimidin- 4- oder 5- oder 6-yl; 1,4-Dihydropyrimidin-l- oder 2- oderHexahydropyrimidine-1 or 2 or 3 or 4-yl; 1,4,5,6-tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidine-1 or 2 or 3 or 4 or 5 or 6-yl; 1,6-dihydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidine-2- or 4- or 5-yl; 4,5-dihydropyrimidine-4- or 5- or 6-yl; 1,4-dihydropyrimidine-I or 2- or
4- oder 5- oder 6-yl; 1- oder 2- oder 3-Piperazinyl; 1,2,3,6-Tetrahydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; 1,2,3,4-Tetrahydropyrazin-l - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,2-Dihydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; 1,4-Dihydropyrazin-l - oder 2- oder 3-yl; 2,3-Dihydropyrazin-2- oder4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazine-1 or 2 or 3 or 5 or 6-yl; 1,2,3,4-tetrahydropyrazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazine 1- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazine-1 - or 2- or 3-yl; 2,3-dihydropyrazine-2-or
3- oder 5- oder 6-yl; 2,5-Dihydropyrazin-2- oder 3-yl; l,3-Dioxolan-2- oder 4- oder 5-yl; l,3-Dioxol-2- oder 4-yl; l,3-Dioxan-2- oder 4- oder 5-yl; 4H-l,3-Dioxin-2- oder 4- oder 5- oder 6-yl; l,4-Dioxan-2- oder 3- oder 5- oder 6-yl; 2,3-Dihydro-l,4-dioxin-2- oder 3- oder 5- oder 6-yl; l,4-Dioxin-2- oder 3-yl; l,2-Dithiolan-3- oder 4-yl; 3H-l,2-Dithiol-3- oder 4- oder 5-yl; l,3-Dithiolan-2- oder 4-yl; 1,3-Dithiol- 2- oder 4-yl; l,2-Dithian-3- oder 4-yl; 3,4-Dihydro-l,2-dithiin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-3- or 5- or 6-yl; 2,5-dihydropyrazine-2 or 3-yl; l, 3-dioxolane-2- or 4- or 5-yl; l, 3-dioxol-2 or 4-yl; 1, 3-dioxan-2 or 4 or 5-yl; 4H-l, 3-dioxin-2 or 4 or 5 or 6-yl; 1, 4-dioxane-2 or 3 or 5 or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; l, 4-dioxin-2 or 3-yl; l, 2-dithiolan-3 or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; l, 3-dithiolan-2 or 4-yl; 1,3-dithiol-2- or 4-yl; 1, 2-dithian-3 or 4-yl; 3,4-dihydro-1,2-dithiin-3 or 4 or 5 or 6-yl; 3,6-dihydro-
1.2- dithiin-3- oder 4-yl; l,2-Dithiin-3- oder 4-yl; l,3-Dithian-2- oder 4- oder 5-yl; 4H-l,3-Dithiin-2- oder 4- oder 5- oder 6-yl; Isoxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisoxazol-3- oder 4- oder 5-yl;1,2-dithiin-3 or 4-yl; l, 2-dithiin-3 or 4-yl; l, 3-dithian-2 or 4 or 5-yl; 4H-l, 3-dithiin-2 or 4 or 5 or 6-yl; Isoxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydroisoxazole-2 or 3 or 4 or 5-yl; 2,5-dihydroisoxazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisoxazole-3 or 4 or 5-yl;
1.3- Oxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-l,3-oxazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydro-l,3-oxazol-2- oder 4- oder 5-yl; 4,5-Dihydro-l,3-oxazol-2- oder 4- oder 5-yl; l,2-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,2-oxazin-3- oder 4- oder 5- oder 6-yl; 2H-l,2-Oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 6H-l,2-Oxazin-3- oder 4- oder 5- oder 6-yl; 4H-l,2-Oxazin-3- oder 4- oder 5- oder 6-yl; l,3-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,3-oxazin-2- oder 3- oder1.3 oxazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazol-2 or 3 or 4 or 5-yl; 2,5-dihydro-1,3-oxazol-2 or 4 or 5-yl; 4,5-dihydro-1,3-oxazol-2 or 4 or 5-yl; 1, 2-oxazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-1,2-oxazine-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-1,2-oxazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1,2-oxazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-4H-1,2-oxazine-3 or 4 or 5 or 6-yl; 2H-l, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-l, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-oxazine-3 or 4 or 5 or 6-yl; l, 3-oxazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-l, 3-oxazine-2 or 3 or
4- oder 5- oder 6-yl; 3,6-Dihydro-2H-l,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H- l,3-oxazin-2- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,3-oxazin-2- oder 4- oder 5- oder 6-yl; 2H- l,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 6H-l,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 4H-l,3-Oxazin-2- oder 4- oder 5- oder 6-yl; Morpholin-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-l,4-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-l,4-oxazin-2- oder 3- oder 5- oder 6-yl; 2H-l,4-oxazin-2- oder 3- oder 5- oder 6-yl; 4H-l,4-oxazin-2- oder 3-yl; 1 ,2-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,3,4,5-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-l,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 4,5,6,7-Tetrahydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,2- oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; l,2-Oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; l,3-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-l,3- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,5,6,7-Tetrahydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-l,3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-l,3-oxazepin- 2- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,7- Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; l,3-Oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 1 ,4-Oxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7- Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,4-oxazepin- 2- oder 3- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7- yl; 4,5,6,7-Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,4- oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 6,7-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 1 ,4-Oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; Isothiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisothiazol-2- oder 3- oder 4- oder 5- yl; 2,5-Dihydroisothiazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisothiazol-3- oder 4- oder 5-yl; 1,3- Thiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-l ,3-thiazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydro-l,3-thiazol-2- oder 4- oder 5-yl; 4,5-Dihydro-l,3-thiazol-2- oder 4- oder 5-yl; l,3-Thiazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-l,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-l,3-thiazin-2- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,3-thiazin-2- oder 4- oder 5- oder 6-yl; 2H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 6H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 4H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl. Weitere Beispiele für "Heterocyclyl" sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit 3 Heteroatomen aus der Gruppe N, O und S, wie beispielsweise l,4,2-Dioxazolidin-2- oder 3- oder 5-yl; l,4,2-Dioxazol-3- oder 5-yl; 1 ,4,2-Dioxazinan-2- oder -3- oder 5- oder 6-yl; 5,6-Dihydro-l,4,2- dioxazin-3- oder 5- oder 6-yl; l,4,2-Dioxazin-3- oder 5- oder 6-yl; l,4,2-Dioxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-5H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-7H-l,4,2- Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-5H-l,4,2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 5H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 7H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl. Strukturbeispiele für gegebenenfalls weiter substituierte Heterocyclen sind auch im Folgenden aufgeführt: 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-oxazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl; 2H-, 3-oxazine-2- or 4- or 5- or 6-yl; 6H-1, 3-oxazine-2 or 4 or 5 or 6-yl; 4H-1, 3-oxazine-2 or 4 or 5 or 6-yl; Morpholine-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 4H-1,4-oxazine-2 or 3-yl; 1, 2-oxazepan-2 or 3 or 4 or 5 or 6 or 7 yl; 2,3,4,5-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1, 2-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,2-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1, 2-oxazepine-3 or 4 or 5 or 6 or 7-yl; 4,7-dihydro-1,2-oxazepine-3 or 4 or 5 or 6 or 7-yl; 6,7-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 1, 2-oxazepine-3 or 4 or 5 or 6 or 7-yl; l, 3-oxazepan-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,4,5-tetrahydro-1, 3-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,4,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1, 3-oxazepine-2 or 4 or 5 or 6 or 7-yl; 2,3-dihydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l, 3-oxazepin 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; l, 3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l, 4-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,6,7-tetrahydro-l, 4-oxazepine 2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-l, 4-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 4-oxazepine-2 or 3 or 4 or 5 or 6 or 7 yl; 6,7-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; Isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2 or 3 or 4 or 5 yl; 2,5-dihydroisothiazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisothiazole-3 or 4 or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazole-2 or 3 or 4 or 5-yl; 2,5-dihydro-1,3-thiazol-2 or 4 or 5-yl; 4,5-dihydro-1,3-thiazol-2 or 4 or 5-yl; l, 3-thiazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-1, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-l, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 5,6-dihydro-4H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 2H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 6H-l, 3-thiazine-2 or 4 or 5 or 6-yl; 4H-l, 3-thiazine-2 or 4 or 5 or 6-yl. Further examples of "heterocyclyl" are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, l, 4,2-dioxazolidin-2 or 3 or 5-yl; l, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazine-3 or 5 or 6-yl; l, 4,2-dioxazine-3- or 5- or 6-yl; l, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1, 4,2-dioxazepine-2 or 3 or 5 or 6 or 7-yl; 5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 7H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:
X) 22 X) 22
Die oben aufgeführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, Alkoxyalkoxy, Cycloalkyl, The 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, Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl,  Halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl,
Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Haloalkylthio, Alkylthio, Hydrothio, Hydroxyalkyl, Oxo, Heteroarylalkoxy, Arylalkoxy, Heterocyclylalkoxy, Heterocyclylalkylthio, Heterocyclyloxy, Heterocyclylthio, Heteroaryloxy, Bis- alkylamino, Alkylamino, Cycloalkylamino, Hydroxycarbonylalkylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Alkoxycarbonylalkyl(alkyl)amino, Aminocarbonyl, Cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, Haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl (alkyl) amino, aminocarbonyl,
Alkylaminocarbonyl, Bis-alkylaminocarbonyl, Cycloalkylaminocarbonyl, Alkylaminocarbonyl, bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
Hydroxycarbonylalkylaminocarbonyl, Alkoxycarbonylalkylaminocarbonyl, Hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl,
Arylalkoxycarbonylalkylaminocarbonyl substituiert. Arylalkoxycarbonylalkylaminocarbonyl substituted.
Wenn ein Grundkörper "durch einen oder mehrere Reste" aus einer Aufzählung von Resten (= Gruppe) oder einer generisch definierten Gruppe von Resten substituiert ist, so schließt dies jeweils die gleichzeitige Substitution durch mehrere gleiche und/oder strukturell unterschiedliche Reste ein. If a main body is "substituted by one or more radicals" from an enumeration of radicals (= group) or a generically defined group of radicals, this includes the simultaneous substitution by a plurality of identical and / or structurally different radicals.
Handelt es sich es sich um einen teilweise oder vollständig gesättigten Stickstoff-Heterocyclus, so kann dieser sowohl über Kohlenstoff als auch über den Stickstoff mit dem Rest des Moleküls verknüpft sein. If it is a partially or fully saturated nitrogen heterocycle, it may be linked to the rest of the molecule via both carbon and nitrogen.
Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo und Thioxo. Die Oxogruppe als Substituent an einem Ring- C-Atom bedeutet dann beispielsweise eine Carbonylgruppe im heterocyclischen Ring. Dadurch sind vorzugsweise auch Lactone und Lactame umfasst. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten und bilden dann beispielsweise die divalenten Gruppen N(O) , S(O) (auch kurz SO) und S(0)2 (auch kurz SO2) im heterocyclischen Ring. Im Fall von -N(O)- und -S(0)-Gruppen sind jeweils beide Enantiomere umfasst. Erfindungsgemäß steht der Ausdruck„Heteroaryl" für heteroaromatische Verbindungen, d. h. Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo. The oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring. As a result, 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. For example, at N and S, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring. In the case of -N (O) and -S (0) groups, both enantiomers are included. According to the invention, the term "heteroaryl" stands for heteroaromatic compounds, ie.
vollständig ungesättigte aromatische heterocyclische Verbindungen, vorzugsweise für 5- bis 7-gliedrige Ringe mit 1 bis 4, vorzugsweise 1 oder 2 gleichen oder verschiedenen Heteroatomen, vorzugsweise O, S oder N. Erfindungsgemäße Heteroaryle sind beispielsweise lH-Pyrrol-l-yl; lH-Pyrrol-2-yl; lH-Pyrrol- 3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, lH-Imidazol-l-yl; lH-Imidazol-2-yl; lH-Imidazol- 4-yl; lH-Imidazol-5-yl; lH-Pyrazol-l-yl; lH-Pyrazol-3-yl; lH-Pyrazol-4-yl; lH-Pyrazol-5-yl, 1H-1,2,3- Triazol-l-yl, lH-l,2,3-Triazol-4-yl, lH-l,2,3-Triazol-5-yl, 2H-l,2,3-Triazol-2-yl, 2H-l,2,3-Triazol-4-yl, lH-l,2,4-Triazol-l-yl, lH-l,2,4-Triazol-3-yl, 4H-l,2,4-Triazol-4-yl, l,2,4-Oxadiazol-3-yl, 1,2,4- Oxadiazol-5-yl, l,3,4-Oxadiazol-2-yl, l,2,3-Oxadiazol-4-yl, l,2,3-Oxadiazol-5-yl, l,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl, completely 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 according to the invention are, for example, 1H-pyrrol-1-yl; lH-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazol-1-yl; lH-imidazol-2-yl; 1H-imidazol-4-yl; lH-imidazol-5-yl; lH-pyrazol-l-yl; lH-pyrazol-3-yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-l, 2,3-triazol-4-yl, 1H-l, 2,3-triazol-5-yl, 2H-l, 2,3-triazol-2-yl, 2H-l, 2,3-triazol-4-yl, 1H-l, 2,4-triazol-1-yl, 1H-l, 2,4- Triazol-3-yl, 4H-l, 2,4-triazol-4-yl, l, 2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, l, 3,4- Oxadiazol-2-yl, l, 2,3-oxadiazol-4-yl, l, 2,3-oxadiazol-5-yl, l, 2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, Pyridin-3-yl, pyridin-4-yl, pyrazine-2-yl, pyrazine-3-yl, pyrimidin-2-yl,
Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, l,3,5-Triazin-2-yl, l,2,4-Triazin-3-yl, l,2,4-Triazin-5-yl, 1 ,2,4-Triazin-6-yl, l,2,3-Triazin-4-yl, l,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- und 1,2,6-Oxazinyl, Isoxazol-3-yl, Isoxazol-4-yl, Isoxazol-5-yl, l,3-Oxazol-2-yl, l,3-Oxazol-4-yl, 1,3- Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, l,3-Thiazol-2-yl, l,3-Thiazol-4-yl, 1,3- Thiazol-5-yl, Oxepinyl, Thiepinyl, 1 ,2,4-Triazolonyl und 1 ,2,4-Diazepinyl, 2H-l,2,3,4-Tetrazol-5-yl, lH-l,2,3,4-Tetrazol-5-yl, l,2,3,4-Oxatriazol-5-yl, l,2,3,4-Thiatriazol-5-yl, l,2,3,5-Oxatriazol-4-yl, l,2,3,5-Thiatriazol-4-yl. Die erfindungsgemäßen Heteroarylgruppen können ferner mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. Sind zwei benachbarte Pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, l, 3,5-triazin-2-yl, l, 2,4-triazin-3-yl, 2,4-triazin-5-yl, 1, 2,4-triazin-6-yl, l, 2,3-triazin-4-yl, l, 2,3-triazin-5-yl, 1,2, 4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazole-2 -yl, 1,3-oxazol-4-yl, 1,3- Oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, l, 3-thiazol-2-yl, l, 3-thiazol-4-yl, 1,3-thiazole 5-yl, oxepinyl, thiepinyl, 1, 2,4-triazolonyl and 1, 2,4-diazepinyl, 2H-l, 2,3,4-tetrazol-5-yl, 1H-l, 2,3,4- Tetrazol-5-yl, l, 2,3,4-oxatriazol-5-yl, l, 2,3,4-thiatriazol-5-yl, l, 2,3,5-oxatriazol-4-yl, 2,3,5-thiatriazole-4-yl. The heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. Are two neighbors
Kohlenstoffatome Bestandteil eines weiteren aromatischen Rings, so handelt es sich um annellierte heteroaromatische Systeme, wie benzokondensierte oder mehrfach annellierte Heteroaromaten.  Carbon atoms part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatic.
Bevorzugt sind beispielsweise Chinoline (z. B. Chinolin-2-yl, Chinolin-3-yl, Chinolin-4-yl, Chinolin-5- yl, Chinolin-6-yl, Chinolin-7-yl, Chinolin-8-yl); Isochinoline (z. B. Isochinolin-l -yl, Isochinolin-3-yl, Isochinolin-4-yl, Isochinolin-5-yl, Isochinolin-6-yl, Isochinolin-7-yl, Isochinolin-8-yl); Chinoxalin; Chinazolin; Cinnolin; 1,5-Naphthyridin; 1 ,6-Naphthyridin; 1 ,7-Naphthyridin; 1,8-Naphthyridin; 2,6- Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe lH-Indol-l-yl, lH-Indol-2-yl, lH-Indol-3-yl, lH-Indol-4-yl, lH-Indol-5-yl, 1H- Indol-6-yl, lH-Indol-7-yl, l-Benzofuran-2-yl, l-Benzofuran-3-yl, l-Benzofuran-4-yl, l-Benzofuran-5- yl, l-Benzofuran-6-yl, l-Benzofuran-7-yl, l-Benzothiophen-2-yl, l-Benzothiophen-3-yl, 1- Benzothiophen-4-yl, l-Benzothiophen-5-yl, l-Benzothiophen-6-yl, l-Benzothiophen-7-yl, lH-Indazol-Preferred are, for example, quinolines (e.g., 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; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine; pyridopyrimidines; Pyridopyridazine; pteridines; Pyrimidopyrimidine. Examples of 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-indol-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-benzothiophene-2-yl, 1-benzothiophen-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5 yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazole
1- yl, lH-Indazol-3-yl, lH-Indazol-4-yl, lH-Indazol-5-yl, lH-Indazol-6-yl, lH-Indazol-7-yl, 2H-Indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazole
2- yl, 2H-Indazol-3-yl, 2H-Indazol-4-yl, 2H-Indazol-5-yl, 2H-Indazol-6-yl, 2H-Indazol-7-yl, 2H- Isoindol-2-yl, 2H-Isoindol-l-yl, 2H-Isoindol-3-yl, 2H-Isoindol-4-yl, 2H-Isoindol-5-yl, 2H-Isoindol-6-yl; 2H-Isoindol-7-yl, lH-Benzimidazol-l-yl, lH-Benzimidazol-2-yl, lH-Benzimidazol-4-yl, 1H- Benzimidazol-5-yl, lH-Benzimidazol-6-yl, lH-Benzimidazol-7-yl, l,3-Benzoxazol-2-yl, 1,3- Benzoxazol-4-yl, l,3-Benzoxazol-5-yl, l,3-Benzoxazol-6-yl, l,3-Benzoxazol-7-yl, l,3-Benzthiazol-2-yl, l,3-Benzthiazol-4-yl, l,3-Benzthiazol-5-yl, l,3-Benzthiazol-6-yl, l,3-Benzthiazol-7-yl, 1,2- Benzisoxazol-3-yl, l,2-Benzisoxazol-4-yl, l,2-Benzisoxazol-5-yl, l,2-Benzisoxazol-6-yl, 1,2-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindole-2 yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H- Benzimidazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, l, 3 Benzoxazol-7-yl, 1,3-benzthiazol-2-yl, 1,3-benzthiazol-4-yl, 1,3-benzthiazol-5-yl, 1,3-benzthiazol-6-yl, l, 3 Benzothiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2-
Benzisoxazol-7-yl, l,2-Benzisothiazol-3-yl, l,2-Benzisothiazol-4-yl, l,2-Benzisothiazol-5-yl, 1,2- Benzisothiazol-6-yl, 1 ,2-Benzisothiazol-7-yl. Benzisoxazol-7-yl, 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1, 2 benzisothiazol-7-yl.
Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder Iod. Wird die The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. Will the
Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder Iodatom. When used to denote a radical, then "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom.
Erfindungsgemäß bedeutet„Alkyl" einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlenwasserstoffrest, der gegebenenfalls ein- oder mehrfach substituiert ist und im letzteren Falle als „substituiertes Alkyl" bezeichnet wird. Bevorzugte Substituenten sind Halogenatome, Alkoxy-,According to the invention, "alkyl" means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted and is referred to in the latter case as "substituted alkyl". Preferred substituents are halogen atoms, alkoxy,
Haloalkoxy-, Cyano-, Alkylthio, Haloalkylthio-, Amino- oder Nitrogruppen, besonders bevorzugt sind Methoxy, Methyl, Fluoralkyl, Cyano, Nitro, Fluor, Chlor, Brom oder Iod. Die Vorsilbe„Bis" schließt auch die Kombination unterschiedlicher Alkylreste ein, z. B. Methyl(Ethyl) oder Ethyl(Methyl). Haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine. The prefix "to" closes also the combination of different alkyl radicals, z. For example, methyl (ethyl) or ethyl (methyl).
„Haloalkyl", ,,-alkenyl" und ,,-alkinyl" bedeuten durch gleiche oder verschiedene Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl "Haloalkyl", "-alkenyl" and "-alkynyl" mean by the same or different halogen atoms, partially or fully substituted alkyl, alkenyl and alkynyl, for example monohaloalkyl
(= Monohalogenalkyl) wie z. B. CH2CH2C1, CH2CH2Br, CHC1CH3, CH2C1, CH2F; Perhaloalkyl wie z. B. CCI3, CC1F2, CFC12,CF2CC1F2, CF2CC1FCF3; Polyhaloalkyl wie z. B. CH2CHFC1, CF2CC1FH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. (= Monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. B. CCl 3, CC1F 2, CFC1 2 CF 2 CC1F 2, CF 2 CC1FCF 3; Polyhaloalkyl such. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3; The term perhaloalkyl also encompasses the term perfluoroalkyl.
„Teilfluoriertes Alkyl" bedeutet einen geradkettigen oder verzweigten, gesättigten Kohlenwasserstoff, der einfach oder mehrfach durch Fluor substituiert ist, wobei sich die entsprechenden Fluoratome als Substituenten an einem oder mehreren verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten Kohlenwasserstoffkette befinden können, wie z. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3 „Teilfluoriertes Haloalkyl" bedeutet einen geradkettigen oder verzweigten, gesättigten "Partially fluorinated alkyl" means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, it being possible for the corresponding fluorine atoms to be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, for example CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3 "Partially fluorinated haloalkyl" means a straight-chain or branched, saturated
Kohlenwasserstoff, der durch verschiedenene Halogenatomen mit mindestens einem Fluoratom substituiert ist, wobei alle anderen gegebenenfalls vorhandenen Halogenatome ausgewählt sind aus der Gruppe Fluor, Chlor oder Brom, Iod. Die entsprechenden Halogenatome können sich dabei als Substituenten an einem oder mehreren verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten Kohlenwasserstoffkette befinden. Teilfluoriertes Haloalkyl schließt auch die vollständige Substitution der geradkettigen oder verzweigten Kette durch Halogen unter Beteiligung von mindestens einem Fluoratom ein.  Hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, wherein all other optional 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 complete substitution of halogen with the participation of at least one fluorine atom of the straight-chain or branched chain.
„Haloalkoxy" ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und 0CH2CH2C1; Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. "Haloalkoxy" is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl, and the same applies to haloalkenyl and other radicals substituted by halogen.
Der hier beispielhaft genannte Ausdruck "(Ci-C4)-Alkyl" bedeutet eine Kurzschreibweise für geradkettiges oder verzweigtes Alkyl mit einem bis 4 Kohlenstoffatomen entsprechend der The term "(C 1 -C 4) -alkyl" given here by way of example denotes a short notation for straight-chain or branched alkyl having one to four carbon atoms corresponding to the formula
Bereichsangabe für C-Atome, d. h. umfasst die Reste Methyl, Ethyl, 1 -Propyl, 2-Propyl, 1 -Butyl, 2-Butyl, 2-Methylpropyl oder tert-Butyl. Allgemeine Alkylreste mit einem größeren angegebenen Bereich von C-Atomen, z. B. "(Ci-C6)-Alkyl", umfassen entsprechend auch geradkettige oder verzweigte Alkylreste mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen. Wenn nicht speziell angegeben, sind bei den Kohlenwasserstoffresten wie Alkyl-, Alkenyl- undRange indication 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. Unless specifically stated, in the hydrocarbon radicals such as alkyl, alkenyl and
Alkinylresten, auch in zusammengesetzten Resten, die niederen Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Resten wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1 -Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Alkinyl radicals, even in composite radicals, the lower carbon skeletons, for example with 1 to 6 carbon atoms or in unsaturated groups having 2 to 6 carbon atoms, preferably. Alkyl radicals, also in the Compound 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. Preference is given to radicals having a double bond or
Dreifachbindung. Triple bond.
Der Begriff„Alkenyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige The term "alkenyl" in particular also includes straight-chain or branched open-chain
Kohlenwasserstoffreste mit mehr als einer Doppelbindung ein, wie 1,3-Butadienyl und 1 ,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (1,2-Propadienyl), 1 ,2-Butadienyl und 1,2,3-Pentatrienyl. Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert sein kann, z B. (aber nicht beschränkt auf) (C2-C6)- Alkenyl wie Ethenyl, 1-Propenyl, 2-Propenyl, 1 -Methylethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl- 1-propenyl, 2-Methyl-l-propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, 1- Pentenyl, 2-Pentenyl, 3 -Pentenyl, 4-Pentenyl, 1 -Methyl- 1 -butenyl, 2-Methyl- 1 -butenyl, 3 -Methyl- 1 - butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3 -butenyl, 2-Methyl-3- butenyl, 3 -Methyl-3 -butenyl, 1 , 1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl- 1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl- 1-propenyl, 1 -Ethyl-2-propenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl, 1 -Methyl- 1 -pentenyl, 2-Methyl- 1 -pentenyl, 3-Methyl-l -pentenyl, 4-Methyl-l -pentenyl, 1- Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, l-Methyl-3- pentenyl, 2-Methyl-3 -pentenyl, 3 -Methyl-3 -pentenyl, 4-Methyl-3 -pentenyl, 1 -Methyl-4-pentenyl, 2- Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 , 1 -Dimethyl-2-butenyl, 1 , 1 -Dimethyl- 3 -butenyl, 1 ,2-Dimethyl- 1 -butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2-Dimethyl-3 -butenyl, 1,3-Dimethyl-l- butenyl, l,3-Dimethyl-2-butenyl, l,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3 -butenyl, 2,3-Dimethyl-l- butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-l -butenyl, 3,3-Dimethyl-2- butenyl, l-Ethyl-l-butenyl, 1-Ethy 1-2 -butenyl, 1 -Ethyl- 3 -butenyl, 2-Ethyl-l -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3 -butenyl, 1 , 1 ,2-Trimethyl-2-propenyl, 1 -Ethyl- 1 -methyl-2-propenyl, 1 -Ethyl-2-methyl- 1 - propenyl und 1 -Ethyl-2-methyl-2-propenyl. Der Begriff„Alkinyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige 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 cumulated double bonds, such as 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, for example (but not limited to) (C 2 -C 6) alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl , 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3 Pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl -2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1 , 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1 pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl , 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3 - pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl 3 -butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl 2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl 3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-1,2-butenyl, 1-ethyl-3-butenyl, 2 Ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl 2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl. The term "alkynyl" in particular also includes straight-chain or branched open-chain
Kohlenwasserstoffreste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren  Hydrocarbon radicals with more than one triple bond or with one or more
Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise 1,3-Butatrienyl bzw. 3-Penten-l -in-l -yl. (C2-C6)-Alkinyl bedeutet z.B. Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-2- butinyl, 1 -Methyl-3 -butinyl, 2-Methyl-3 -butinyl, 3 -Methyl- 1 -butinyl, 1 , 1 -Dimethyl-2-propinyl, 1 -Ethyl- 2-propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, l-Methyl-3- pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3 -Methyl- 1-pentinyl, 3- Methyl-4-pentinyl, 4-Methyl-l -pentinyl, 4-Methyl-2-pentinyl, 1 , 1 -Di-methyl-2-butinyl, 1 , 1 -Dimethyl-3 - butinyl, l ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-l -butinyl, 1 -Ethyl-2-butinyl, 1 - Ethyl-3-butinyl, 2-Ethyl-3 -butinyl und l -Ethyl-l -methyl-2-propinyl. Der Begriff„Cycloalkyl" bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-8 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, das gegebenenfalls weiter substituiert ist, bevorzugt durch Wasserstoff, Alkyl, Alkoxy, Cyano, Nitro, Alkylthio, Haloalkylthio, Halogen, Alkenyl, Alkinyl, Haloalkyl, AMino, Alkylamino, Bisalkylamino, Alkocycarbonyl, Triple bonds and one or more double bonds, such as 1,3-butatrienyl and 3-penten-1-yn-1-yl, respectively. (C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 Pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1 - Ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3 Methyl 4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-di-methyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl 3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1 - Ethyl 1-methyl-2-propynyl. The term "cycloalkyl" means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl,
Hydroxycarbonyl, Arylalkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Cycloalkylaminocarbonyl. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer Doppelbindung am Cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on
Cycloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden auch mehrcyclische aliphatische Systeme umfasst, wie beispielsweise Bicyclo[l .1.0]butan-l -yl, Bicyclo[l .1.0]butan-2-yl, Bicyclo[2.1.0]pentan-l -yl, Bicyclo[l .1.1 ]pentan-l - yl, Bicyclo[2.1.0]pentan-2-yl, Bicyclo[2.1.0]pentan-5-yl, Bicyclo[2.1.1 ]hexyl, Bicyclo[2.2.1 ]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1 ]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-l -yl und Adamantan-2-yl, aber auch Systeme wie z. B. l ,l '-Bi(cyclopropyl)-l -yl, l , l '-Bi(cyclopropyl)-2-yl. Der Ausdruck "(C3-C7)-Cycloalkyl" bedeutet eine Kurzschreibweise für Cycloalkyl mit drei bis 7 Cycloalkyl, z. As an alkylidene group such as methylidene, are included. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, such as, for example, bicyclo [1,1.0] butan-1-yl, bicyclo [1,1-0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl , Bicyclo [1,11] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1 ] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantane-1-yl and adamantane -2-yl, but also systems such. B. l, l '-Bi (cyclopropyl) -1-yl, l, l' -Bi (cyclopropyl) -2-yl. The term "(C 3 -C 7) -cycloalkyl" means a short notation for cycloalkyl of three to seven
Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome. Carbon atoms corresponding to the range for C atoms.
Im Falle von substituiertem Cycloalkyl werden auch spirocyclische aliphatische Systeme umfasst, wie beispielsweise Spiro[2.2]pent-l -yl, Spiro[2.3]hex-l -yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept-l -yl, Spiro[3.3]hept-2-yl. „Cycloalkenyl" bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-8 C-Atomen, z.B. 1 -Cyclobutenyl, 2-Cyclobutenyl, 1 -Cyclopentenyl, 2-Cyclopentenyl, 3 -Cyclopentenyl, oder 1 -Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, 1 ,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend. In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl. "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 substituents having a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene, are also included in the case of optionally substituted cycloalkenyl the explanations for substituted Corresponding to cycloalkyl.
Der Begriff„Alkyliden", z. B. auch in der Form (Ci-Cio)-Alkyliden, bedeutet den Rest eines geradkettigen oder verzweigten offenkettigen Kohlenwasserstoffrests, der über eine Zweifachbindung gebunden ist. Als Bindungsstelle für Alkyliden kommen naturgemäß nur Positionen am Grundkörper in Frage, an denen zwei H- Atome durch die Doppelbindung ersetzt werden können; Reste sind z. B. =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5 oder =C(C2H5)-C2H5. Cycloalkyliden bedeutet ein The term "alkylidene", for example also in the form of (C 1 -C 10) -alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.As a binding site for alkylidene, only positions on the main body naturally occur Question in which two hydrogen atoms can be replaced by the double bond: radicals are eg = CH 2 , = CH-CH 3 , = C (CH 3 ) -CH 3 , = C (CH 3 ) -C 2 H 5 or = C (C 2 H 5 ) -C 2 H 5. Cycloalkylidene means
carbocyclischer Rest, der über eine Zweifachbindung gebunden ist. „Cycloalkylalkyloxy" bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylalkylrest und „Arylalkyloxy" bedeutet ein über ein Sauerstoffatom gebundenen Arylalkylrest. „Alkoxyalkyl" steht für einen über eine Alkylgruppe gebundenen Alkoxyrest und„Alkoxyalkoxy" bedeutet einen über ein Sauerstoffatom gebundenen Alkoxyalkylrest, z.B. (aber nicht beschränkt auf) Methoxymethoxy, Methoxyethoxy, Ethoxyethoxy, Methoxy-n-propyloxy. carbocyclic radical bonded via a double bond. "Cycloalkylalkyloxy" means a cycloalkylalkyl radical bonded via an oxygen atom, and "arylalkyloxy" means an arylalkyl radical bonded via an oxygen atom. "Alkoxyalkyl" means an alkoxy group attached via an alkyl group and "alkoxyalkoxy" means an alkoxyalkyl group bonded through an oxygen atom, for example (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
„Alkylthioalkyl" steht für einen über eine Alkylgruppe gebundenen Alkylthiorest und "Alkylthioalkyl" means an alkylthio radical bonded via an alkyl group and
„Alkylthioalkylthio" bedeutet einen über ein Sauerstoffatom gebundenen Alkylthioalkylrest. "Alkylthioalkylthio" means an alkylthioalkyl radical bonded via an oxygen atom.
„Arylalkoxyalkyl" steht für einen über eine Alkylgruppe gebundenen Aryloxyrest und "Arylalkoxyalkyl" stands for an aryloxy radical bound via an alkyl group and
„Heteroaryloxyalkyl" bedeutet einen über eine Alkylgruppe gebundenen Heteroaryloxyrest. „Haloalkoxyalkyl" steht für einen gebundenen Haloalkoxyrest und„Haloalkylthioalkyl" bedeutet einen über eine Alkylgruppe gebundenen Haloalkylthiorest. "Heteroaryloxyalkyl" means a heteroaryloxy group attached via an alkyl group. "Haloalkoxyalkyl" means a haloalkoxy group attached and "haloalkylthioalkyl" means a haloalkylthio group attached via an alkyl group.
„Arylalkyl" steht für einen über eine Alkylgruppe gebundenen Arylrest,„Heteroarylalkyl" bedeutet einen über eine Alkylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkyl" bedeutet einen über eine Alkylgruppe gebundenen Heterocyclylrest. "Arylalkyl" means an aryl group attached via an alkyl group, "heteroarylalkyl" means a heteroaryl group bonded via an alkyl group, and "heterocyclylalkyl" means a heterocyclyl group bonded through an alkyl group.
„Cycloalkylalkyl" steht für einen über eine Alkylgruppe gebundenen Cycloalkylrest, z. B. (aber nicht beschränkt auf) Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, 1 - Cyclopropyleth-l -yl, 2-Cyclopropyleth-l -yl, 1 -Cyclopropylprop-l -yl, 3-Cyclopropylprop-l -yl. "Cycloalkylalkyl" means a cycloalkyl radical attached via an alkyl group, for example (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylpropyl l -yl, 3-cyclopropylprop-1-yl.
„Arylalkenyl" steht für einen über eine Alkenylgruppe gebundenen Arylrest,„Heteroarylalkenyl" bedeutet einen über eine Alkenylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkenyl" bedeutet einen über eine Alkenylgruppe gebundenen Heterocyclylrest. „Arylalkinyl" steht für einen über eine Alkinylgruppe gebundenen Arylrest,„Heteroarylalkinyl" bedeutet einen über eine Alkinylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkinyl" bedeutet einen über eine Alkinylgruppe gebundenen Heterocyclylrest. "Arylalkenyl" is an aryl radical bonded via an alkenyl group, "heteroarylalkenyl" denotes a heteroaryl radical bonded via an alkenyl group, and "heterocyclylalkenyl" denotes a heterocyclyl radical bonded via an alkenyl group. "Arylalkynyl" denotes an aryl radical bonded via an alkynyl group, "heteroarylalkynyl" represents a heteroaryl group bonded via an alkynyl group, and "heterocyclylalkynyl" means a heterocyclyl group bonded via an alkynyl group.
Erfindungsgemäß steht "Haloalkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Halogenalkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention "haloalkylthio" - alone or as part of a chemical group - is straight-chain or branched S-haloalkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie (Ci-Cs)-, (CI-CÖ)- oder (Ci-C4)-Haloalkylthio, z.B. (aber nicht beschränkt auf) Trifluormethylthio, Pentafluorethylthio, Difluormethyl, 2,2-Difluoreth-l -ylthio, 2,2,2-Difluoreth-l - ylthio, 3,3,3-prop-l -ylthio. Carbon atoms, such as (Ci-Cs) -, (CI-CÖ) - or (Ci-C4) haloalkylthio, for example (but not limited to) Trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
„Halocycloalkyl" und„Halocycloalkenyl" bedeuten durch gleiche oder verschiedene Halogenatome, wie z. B. F, Cl und Br, oder durch Haloalkyl, wie z. B. Trifluormethyl oder Difluormethyl teilweise oder vollständig substituiertes Cycloalkyl oder Cycloalkenyl , z.B. 1 -Fluorcycloprop-l -yl, 2-Fluorcycloprop- 1 -yl, 2,2-Difluorcycloprop-l -yl, 1 -Fluorcyclobut-l -yl, 1 -Trifluormethylcycloprop-l -yl, 2- Trifluormethylcycloprop- 1 -yl, 1 -Chlor-cycloprop- 1 -yl, 2-Chlorcycloprop- 1 -yl, 2,2-Dichlorcycloprop- 1 - yl, 3,3-Difluorcyclobutyl, "Halocycloalkyl" and "Halocycloalkenyl" mean by the same or different halogen atoms, such as. B. F, Cl and Br, or by haloalkyl, such as. Trifluoromethyl or difluoromethyl, partially or fully substituted cycloalkyl or cycloalkenyl, e.g. 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobutyl-1, 1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl,
Erfindungsgemäß steht "Trialkylsilyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Si-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention "trialkylsilyl" - alone or as part of a chemical group - is straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie Tri-[(Ci-Cg)-, (Ci-Ce)- oder (Ci-C4)-alkyl]silyl, z.B. (aber nicht beschränkt auf) Trimethylsilyl, Triethylsilyl, Tri-(n-propyl)silyl, Tri-(iso-propyl)silyl, Tri-(n-butyl)silyl, Tri-(1 - methylprop- 1 -yl)silyl, Tri-(2-methylprop- 1 -yl)silyl, Tri( 1 , 1 -Dimethyleth- 1 -yl)silyl, Tri(2,2- Dimethyleth- 1 -yl)silyl. Carbon atoms such as tri - [(Ci-Cg) -, (Ci-Ce) - or (Ci-C4) -alkyl] silyl, e.g. (but not limited to) trimethylsilyl, triethylsilyl, tri (n-propyl) silyl, tri (iso-propyl) silyl, tri (n-butyl) silyl, tri (1-methylprop-1-yl) silyl, Tri- (2-methylprop-1-yl) silyl, tri (1,1-dimethyl-1-yl) silyl, tri (2,2-dimethyl-1-yl) silyl.
„Trialkylsilylalkinyl" steht für einen über eine Alkinylgruppe gebundenen Trialkylsilylrest. Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die allgemeine Formel (I) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) umfasst, sofern nicht ein bestimmtes Tautomer Gegenstand der Betrachtung ist. So können beispielsweise viele If the compounds can form tautomers by hydrogen shift which would not be structurally formally recognized by the general formula (I), these tautomers are nevertheless of the definition of the compounds of the general formula (II) embedded image I), unless a particular tautomer is the subject of consideration
Carbonylverbindungen sowohl in der Ketoform wie auch in der Enolform vorliegen, wobei beide Formen durch die Definition der Verbindung der allgemeinen Formel (I) umfasst werden. Carbonyl compounds in both the keto form as well as in the enol form, both forms by the definition of the compound of general formula (I) are included.
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Die durch ihre spezifische Raumform definierten möglichen Stereoisomere, wie Enantiomere, Diastereomere, Z- und E-Isomere sind alle von der allgmeinen Formel (I) umfasst. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E- Isomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Stereoisomere lassen sich aus den bei der Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can 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 general 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 distinguished from those in the
Herstellung anfallenden Gemischen nach üblichen Trennmethoden erhalten. Die chromatographische Trennung kann sowohl im analytischen Maßstab zur Feststellung des Enantiomerenüberschusses bzw. des Diastereomerenüberschusses, wie auch im präparativen Maßstab zur Herstellung von Prüfmustern für die biologische Ausprüfung erfolgen. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft somit auch alle Stereoisomeren, die von der allgemeinen Formel (I) umfasst, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind, sowie deren Gemische. Preparation of resulting mixtures obtained by conventional separation methods. The chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale for the preparation of test samples for the biological assay. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants become. 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.
Sofern die Verbindungen als Feststoffe erhalten werden, kann die Reinigung auch durch If the compounds are obtained as solids, the purification can also by
Umkristallisieren oder Digerieren erfolgen. Sofern einzelne Verbindungen (I) nicht auf den nachstehend beschriebenen Wegen zufriedenstellend zugänglich sind, können sie durch Derivatisierung anderer Verbindungen (I) hergestellt werden. Recrystallize or digest. Unless individual compounds (I) are satisfactorily accessible by the routes described below, they can be prepared by derivatization of other compounds (I).
Als Isolierungs-, Reinigungs- und Stereoisomerenauftrennungsverfahren von Verbindungen der allgemeinen Formel (I) kommen Methoden in Frage, die dem Fachmann aus analogen Fällen allgemein bekannt sind, z.B. durch physikalische Verfahren wie Kristallisation, Chromatographieverfahren, vor allem Säulenchromatographie und HPLC (Hochdruckflüssigchromatographie), Destillation, gegebenenfalls unter reduziertem Druck, Extraktion und andere Verfahren, können gegebenfalls verbleibende Gemische in der Regel durch chromatographische Trennung, z.B. an chiralen Festphasen, getrennt werden. Für präparative Mengen oder im industriellen Maßstab kommen Verfahren in Frage wie Kristallisation, z.B. diastereomerer Salze, die aus den Diastereomerengemischen mit optisch aktiven Säuren und gegebenenfalls bei vorhandenen sauren Gruppen mit optisch aktiven Basen erhalten werden können. Die vorliegende Erfindung beansprucht auch Verfahren zur Herstellung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I). Suitable isolation, purification and stereoisomer separation methods of compounds of general formula (I) are those which are well known to those skilled in the art from analogous cases, e.g. by physical methods such as crystallization, chromatographic methods, especially column chromatography and HPLC (high performance liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods, residual mixtures may optionally be removed by chromatographic separation, e.g. at chiral solid phases, to be separated. For preparative amounts or on an industrial scale, such processes as crystallization, e.g. diastereomeric salts which can be obtained from the diastereomeric mixtures with optically active acids and optionally in the presence of acidic groups with optically active bases. The present invention also claims processes for the preparation of the compounds of the general formula (I) according to the invention.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können unter anderem ausgehend von bekannten Verfahren hergestellt werden. Die eingesetzten und untersuchten Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren Bausteinen aus. Die Gruppierungen Q1, Q2, A, R1, R2, n der all gemeinen Formel (I) haben in den nachfolgenden Schemata die zuvor definierten Bedeutungen, sofern nicht beispielhafte, aber nicht einschränkende, Definitionen erfolgen. The compounds of the general formula (I) according to the invention can be prepared inter alia starting from known processes. The synthetic routes used and investigated are based on commercially available or easily manufacturable building blocks. The groups Q 1, Q 2, A, R 1, R 2, n of all the common formula (I) in the Schemes below the previously defined meanings, unless exemplary, but not limiting, carried definitions.
Erfindungsgemäße Verbindungen mit R1 für Methyl und A für O, S(0)n und CR3R4 können beispielsweise nach der in Schema 1 angegebenen Methode hergestellt werden. Compounds according to the invention with R 1 for methyl and A for O, S (O) n and CR 3 R 4 can be prepared, for example, by the method given in Scheme 1.
Schema 1 Die Pyrazole der allgemeinen Formel (I) können über eine Alkyierung der Pyrazolone (E-III) in Scheme 1 The pyrazoles of the general formula (I) can be prepared via an alkylation of the pyrazolones (E-III) in
Gegenwart von Basen, Alkyierungsmitteln wie zum Beispiel Q2-X, wobei X eine Abgangsgruppe ist, und Kupfer(I)-Salze, hergestellt werden. Die Base kann ein Carbonat-Salz von einem Alkali-Metall (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Kupfersalze können Kupferhalogenide, wie zum Beispiel Kupfer(I)-Iodid, sein. Die Reaktionen werden im Allgemeinen in einem organischen Presence of bases, alkylating agents such as Q 2 -X, wherein X is a leaving group, and copper (I) salts are prepared. The base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium). The copper salts may be copper halides, such as cuprous iodide. The reactions are generally in an organic
Lösungsmittel, wie zum Beispiel Acetonitril oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Die Pyrazole der allgemeinen Formel (E-III) können über eine Dealkyierung der Pyrazole (E-II) in Gegenwart von Säuren wie zum Beispiel Bromwasserstoffsäure, hergestellt werden. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Essigsäure, bei Solvent, such as acetonitrile or dimethylformamide, at temperatures between 0 ° C and the boiling point of the solvent carried out. The pyrazoles of the general formula (E-III) can be prepared via a dealkyation of the pyrazoles (E-II) in the presence of acids such as, for example, hydrobromic acid. The reactions are generally incorporated in an organic solvent such as acetic acid
Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Die Pyrazole der allgemeinen Formel (E-II) können über eine Bisalkyierung der Pyrazolone (E-I) inTemperatures between 0 ° C and the boiling point of the solvent, carried out. The pyrazoles of the general formula (E-II) can be prepared via a Bisalkyierung of pyrazolones (E-I) in
Gegenwart von Basen und Alkyierungsmitteln wie zum Beispiel R'-X, wobei X eine Abgangsgruppe ist, hergestellt werden. Die Base kann ein Carbonat-Salz von einem Alkali-Metall (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Acetonitril oder Tetrahydrofuran, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Presence of bases and Alkyierungsmitteln such as R'-X, where X is a leaving group can be produced. The base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium). The reactions are generally carried out in an organic solvent, such as acetonitrile or tetrahydrofuran, at temperatures between 0 ° C and the boiling point of the solvent.
Pyrazolone der allgemeinen Formel (E-I) sind literaturbekannt und können beispielsweise gemäß den in Eur. J. Med. Chem. 2009, 44, 3852-7, J. Heterocyclic Chem. 2011, 48, 323-330, Org. Lett. 2016, 18, 6388-91, WO 2016/066664 AI, WO 2011/039338 A2 und ähnlich beschriebenen Methoden hergestellt werden. Pyrazolones of the general formula (E-I) are known from the literature and can be prepared, for example, according to the methods described in Eur. J. Med. Chem. 2009, 44, 3852-7, J. Heterocyclic Chem. 2011, 48, 323-330, Org. 2016, 18, 6388-91, WO 2016/066664 A1, WO 2011/039338 A2 and methods described in a similar manner.
Erfindungsgemäße Verbindungen mit A für O, S(0)n und CR3R4 können auch beispielsweise nach der in Schema 2 angegebenen Methode hergestellt werden. NH2NH-PG Compounds according to the invention with A for O, S (O) n and CR 3 R 4 can also be prepared, for example, by the method given in Scheme 2. NH 2 NH-PG
(E-Vl) (la)  (E-Vl) (la)
Schema 2.  Scheme 2.
Die Pyrazole der allgemeinen Formel (I) können über eine Alkyierung der Pyrazolone (Ia) in Gegenwart von Basen und Alkyierungsmitteln wie zum Beispiel R'-X, wobei X eine Abgangsgruppe ist, hergestellt werden. Die Base kann ein Carbonat-Salz von einem Alkali-Metall (wie zum Beispiel Natrium, Kalium oder Cäsium), oder ein Amin (wie zum Beispiel Triethylamin) sein. Die Reaktionen werden im The pyrazoles of the general formula (I) can be prepared via an alkylation of the pyrazolones (Ia) in the presence of bases and alkylating agents such as R'-X, where X is a leaving group. The base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium) or an amine (such as triethylamine). The reactions are in the
Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Acetonitril, Tetrahydrof ran oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Generally in an organic solvent, such as acetonitrile, tetrahydrofuran or dimethylformamide, at temperatures between 0 ° C and the boiling point of the solvent carried out.
Die Pyrazole der allgemeinen Formel (Ia) können über eine Entschützung der Pyrazole (E-VI) in Gegenwart von Säuren wie zum Beispiel Trifluoressigsäure, hergestellt werden. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Dichlormethan, oder in The pyrazoles of general formula (Ia) can be prepared via deprotection of the pyrazoles (E-VI) in the presence of acids such as trifluoroacetic acid. The reactions are generally carried out in an organic solvent, such as dichloromethane, or in
Substanz bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Wie dem Fachmann bekannt ist, können die NH-Pyrazole Ia auch in ihrer entsprechenden anderen tautomeren Form vorliegen. Substance at temperatures between 0 ° C and the boiling point of the solvent, carried out. As is known to the person skilled in the art, the NH-pyrazoles Ia can also be present in their corresponding other tautomeric form.
Die Pyrazole der allgemeinen Formel (E-VI) können über eine Alkyierung der Pyrazolone (E-V) in Gegenwart von Basen und Alkyierungsmitteln wie zum Beispiel Q2-X, wobei X eine Abgangsgruppe ist, hergestellt werden. Die Base kann ein Carbonat-Salz von einem Alkali-Metall (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Butyronitril, Acetonitril oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Die Verbindungen der allgemeinen Formel (E-V) können durch Reaktion der Bausteine (E-IV) mitThe pyrazoles of the general formula (E-VI) can be prepared via an alkylation of the pyrazolones (EV) in the presence of bases and alkylating agents such as Q 2 -X, where X is a leaving group. The base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium). The reactions are generally carried out in an organic solvent, such as butyronitrile, acetonitrile or dimethylformamide, at temperatures between 0 ° C and the boiling point of the solvent. The compounds of the general formula (EV) can be obtained by reaction of the building blocks (E-IV) with
Hydrazinen wie zum Beispiel NF NH-PG, wobei PG eine Schützgruppe ist, erhalten werden. Die dabei verwendeten Hydrazine können in freier Form oder als Salze vorliegen, beispielsweise als Hydrochloride. Im Fall der Verwendung von Salzen kann es vorteilhaft sein, dem Reaktionsgemisch eine organische oder anorganische Base zuzusetzen, wie zum Beispiel Triethylamin. Die Schützgruppe PG kann zum Beispiel Benzyl oder 4-Methoxybenzyl sein. Die Reaktion wird im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Ethanol, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels durchgeführt. Hydrazines such as NF NH-PG, where PG is a protecting group. The hydrazines used in this case can be present in free form or as salts, for example as Hydrochloride. In the case of using salts, it may be advantageous to add to the reaction mixture an organic or inorganic base, such as triethylamine. The protecting group PG may be, for example, benzyl or 4-methoxybenzyl. The reaction is generally carried out in an organic solvent, such as ethanol, at temperatures between 0 ° C and the boiling point of the solvent.
Ketoester der allgemeinen Formel (E-IV) sind literaturbekannt und können beispielsweise gemäß den in Tetrahedron, 1982, 38, 85-91, J. Am. Chem. Soc. 2013, 135, 14556-14559 und ähnlich beschriebenen Methoden hergestellt werden. Wie dem Fachmann bekannt ist, können die Ketoester E-IV auch in ihrer entsprechenden anderen tautomeren Form vorliegen. Keto esters of the general formula (E-IV) are known from the literature and can be prepared, for example, according to the methods described in Tetrahedron, 1982, 38, 85-91, J. Am. Chem. Soc. 2013, 135, 14556-14559 and similarly described methods. As known to those skilled in the art, the ketoesters E-IV may also be present in their corresponding other tautomeric form.
Erfindungsgemäße Verbindungen können auch beispielsweise nach der in Schema 3 angegebenen Methode hergestellt werden. Compounds of the invention may also be prepared, for example, by the method given in Scheme 3.
(E-Vll) (E-VIII) (E-IX) (Ib) (E-VII) (E-VIII) (E-IX) (Ib)
Schema 3. Scheme 3.
Die Pyrazole der allgemeinen Formel (Ib) können über eine Substitutionsreaktion der Pyrazole (E-IX) mit Schwefelnucleophilen wie zum Beispiel Q2-SH in Gegenwart von Basen und Kupfer(I)-Salze hergestellt werden. Die Base kann ein Hydrid-Salz von einem Alkali-Metall (wie zum Beispiel Natrium) sein. Die Kupfersalze können Kupferhalogenide, wie zum Beispiel Kupfer(I)-Iodid, sein. Die The pyrazoles of the general formula (Ib) can be prepared via a substitution reaction of the pyrazoles (E-IX) with sulfur nucleophiles such as Q 2 -SH in the presence of bases and copper (I) salts. The base may be a hydride salt of an alkali metal (such as sodium). The copper salts may be copper halides, such as cuprous iodide. The
Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Reactions are generally in an organic solvent, such as
Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Die Pyrazole der allgemeinen Formel (E-IX) können über eine Iodierung der Pyrazole (E-VIII) mit einem geeigneten Iodierungsmittel, wie zum Beispiel Jod, im Gegenwart von Cerammoniumnitrat hergestellt werden. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Acetonitril, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Dimethylformamide, carried out at temperatures between 0 ° C and the boiling point of the solvent. The pyrazoles of general formula (E-IX) may be prepared by iodination of the pyrazoles (E-VIII) with a suitable iodinating agent, such as iodine, in the presence of ceric ammonium nitrate. The reactions are generally carried out in an organic solvent, such as acetonitrile, at temperatures between 0 ° C and the boiling point of the solvent.
Die Pyrazole der allgemeinen Formel (E-VIII) können über eine Alkyierung der Pyrazolone (E-VII) in Gegenwart von Basen, Alkyierungsmitteln wie zum Beispiel Q2-X, wobei X eine Abgangsgruppe ist, und Kupfer(I)-Salze, hergestellt werden. Die Base kann ein Carbonat-Salz von einem Alkali-Metall (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Kupfersalze können Kupferhalogenide, wie zum Beispiel Kupfer(I)-Iodid, sein. Die Reaktionen werden im Allgemeinen in einem organischen The pyrazoles of the general formula (E-VIII) can be prepared via an alkylation of the pyrazolones (E-VII) in the presence of bases, alkylating agents such as Q 2 -X, where X is a leaving group, and copper (I) salts become. The base may be a carbonate salt of an alkali metal (such as for example, sodium, potassium or cesium). The copper salts may be copper halides, such as cuprous iodide. The reactions are generally in an organic
Lösungsmittel, wie zum Beispiel Acetonitril oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Solvent, such as acetonitrile or dimethylformamide, at temperatures between 0 ° C and the boiling point of the solvent carried out.
Pyrazole der allgemeinen Formel (E-VII) sind literaturbekannt und können beispielsweise gemäß den in J. Org. Chem. 2015, 80, 6001-6011, WO2013/110643 AI, US5663365 A, WO2015/50989 A2, WO2015/095788 und ähnlich beschriebenen Methoden hergestellt werden. Wie dem Fachmann bekannt ist, können die Pyrazole (E-VII) auch in ihrer entsprechenden anderen tautomeren Form vorliegen. Pyrazoles of the general formula (E-VII) are known from the literature and can be prepared, for example, according to the methods described in J. Org. Chem. 2015, 80, 6001-6011, WO2013 / 110643 A1, US Pat. No. 5,663,365, WO2015 / 50989 A2, WO2015 / 095788 and the like Methods are produced. As known to those skilled in the art, the pyrazoles (E-VII) may also be present in their corresponding other tautomeric form.
Erfindungsgemäße Verbindungen können auch beispielsweise nach der in Schema 4 angegebenen Methode hergestellt werden. Compounds of the invention may also be prepared, for example, by the method given in Scheme 4.
(E-IX) (Ic)  (E-IX) (Ic)
Schema 4. Scheme 4.
Die Pyrazole der allgemeinen Formel (Ic) können über eine Suzuki-Reaktion der Pyrazole (E-IX) mit Boronsäuren wie zum Beispiel Q2-B(OH)2 in Gegenwart von Basen und Palladium-Katalysatoren (wie zum Beispiel PdC ^dppfXCFhCL)) hergestellt werden. Die Base kann ein Carbonat-Salz von einem Alkali-Metall (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Dioxane, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. The pyrazoles of the general formula (Ic) can be prepared via a Suzuki reaction of the pyrazoles (E-IX) with boronic acids such as, for example, Q 2 -B (OH) 2 in the presence of bases and palladium catalysts (such as PdC ^ dppfXCFhCL) ) getting produced. The base may be a carbonate salt of an alkali metal (such as sodium, potassium or cesium). The reactions are generally carried out in an organic solvent, such as dioxanes, at temperatures between 0 ° C and the boiling point of the solvent.
Erfindungsgemäße Verbindungen können auch beispielsweise nach der in Schema 5 angegebenen Methode hergestellt werden. Compounds of the invention may also be prepared, for example, by the method given in Scheme 5.
(E-VIII) (E-X) (E-Xl) (Id) (le) (E-VIII) (E-X) (E-XI) (Id) (le)
Schema 5 Die Pyrazole der allgemeinen Formel (Ie) können über eine Alkyierung der Pyrazolone (Id) in Scheme 5 The pyrazoles of the general formula (Ie) can be obtained via an alkylation of the pyrazolones (Id) in
Gegenwart von Basen und Alkyierungsmitteln wie zum Beispiel R5-X, wobei X eine Abgangsgruppe ist, hergestellt werden. Die Base kann ein Hydrid-Salz von einem Alkali-Metall (wie zum Beispiel Natrium) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Acetonitril, Tetrahydrofuran oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Presence of bases and Alkyierungsmitteln such as R 5 -X, where X is a leaving group are prepared. The base may be a hydride salt of an alkali metal (such as sodium). The reactions are generally carried out in an organic solvent, such as acetonitrile, tetrahydrofuran or dimethylformamide, at temperatures between 0 ° C and
Siedepunkt des Lösemittels, durchgeführt. Boiling point of the solvent, carried out.
Die Pyrazole der allgemeinen Formel (Id) können über eine Buckwald-Hartwig-Kupplung der Pyrazole (E-XI) mit Arylhalogenids oder Aryltriflats wie zum Beispiel Ql-X in Gegenwart von Basen, Palladium- Katalysatoren (wie zum Beispiel Tris(dibenzylidenaceton)dipalladium(0)) und Liganden (wie zumThe pyrazoles of general formula (Id) can be obtained via a Buckwald-Hartwig coupling of the pyrazoles (E-XI) with aryl halides or aryl triflates such as, for example, Q l -X in the presence of bases, palladium catalysts (for example tris (dibenzylideneacetone) dipalladium (0)) and ligands (such as
Beispiel Xantphos) hergestellt werden. Die Base kann ein Phosphat-Salz von einem Alkali-Metall (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Toluol, bei Temperaturen zwischen 0°C und dem Example Xantphos) are produced. The base may be a phosphate salt of an alkali metal (such as sodium, potassium or cesium). The reactions are generally carried out in an organic solvent, such as toluene, at temperatures between 0 ° C and
Siedepunkt des Lösemittels, durchgeführt. Boiling point of the solvent, carried out.
Die Pyrazole der allgemeinen Formel (E-XI) können über eine Reduktion der Pyrazole (E-X) hergestellt werden. Solche Reaktionen sind dem Fachmann bekannt und beispielsweise in WO2008/8375 A2 und WO201 1/3065 A2 beschrieben. Die Pyrazole der allgemeinen Formel (E-X) können über eine Nitrierung der Pyrazole (E-VIII) hergestellt werden. Solche Reaktionen sind dem Fachmann bekannt und beispielsweise in The pyrazoles of the general formula (E-XI) can be prepared via a reduction of the pyrazoles (E-X). Such reactions are known to the person skilled in the art and are described, for example, in WO2008 / 8375 A2 and WO201 1/3065 A2. The pyrazoles of the general formula (E-X) can be prepared via a nitration of the pyrazoles (E-VIII). Such reactions are known to the skilled person and, for example, in
WO2005/99688 A2 und US2014/194452 AI beschrieben. WO2005 / 99688 A2 and US2014 / 194452 AI described.
Erfindungsgemäße Verbindungen mit n für 1 und 2 können beispielsweise nach der in Schema 6 an egebenen Methode hergestellt werden. Compounds according to the invention with n for 1 and 2 can be prepared, for example, according to the method given in Scheme 6.
Schema 6 Scheme 6
Die Sulfone und Sulfoxide der allgemeinen Formel (If) können über eine Oxidation der Pyrazole (Ib) hergestellt werden. Solche Reaktionen sind dem Fachmann bekannt und beispielsweise in Eur. J. Med. Chem. 2014, 71 , 168-184 und Org. Lett. 2013, 15, 3994-3997 beschrieben. Ausgewählte detaillierte Synthesebeispiele für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) sind im Folgenden aufgeführt. Die 'H-NMR-, 13C-NMR- und 19F-NMR-spektroskopischen Daten, die für die in den nachfolgenden Abschnitten beschriebenen chemischen Beispiele angegeben sind, (400 MHz bei 'H-NMR und 150 MHz bei 13C-NMR und 375 MHz bei "F-NMR, Lösungsmittel CDCb, CD3OD oder d6-DMSO, interner Standard: Tetramethylsilan δ = 0.00 ppm), wurden mit einem Gerät der Firma Bruker erhalten, und die bezeichneten Signale haben die nachfolgend aufgeführten Bedeutungen: br = breit(es); s = Singulett, d = Dublett, t = Triplett, dd = Doppeldublett, ddd = Dublett eines Doppeldubletts, m = Multiplett, q = Quartett, quint = Quintett, sext = Sextett, sept = Septett, dq = Doppelquartett, dt = Doppeltriplett. Bei Diastereomerengemischen werden entweder die jeweils signifikanten Signale beider Diastereomere oder das charakteristische Signal des Hauptdiastereomers angegeben. Die verwendeten Abkürzungen für chemische Gruppen haben beispielsweise die nachfolgenden Bedeutungen: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n- Bu = unverzweigtes Butyl, n-Pr = unverzweigtes Propyl, i-Pr = verzweigtes Propyl, c-Pr = Cyclopropyl, c-Hex = Cyclohexyl. The sulfones and sulfoxides of the general formula (If) can be prepared via an oxidation of the pyrazoles (Ib). Such reactions are known to the person skilled in the art and are described, for example, in Eur. J. Med. Chem. 2014, 71, 168-184 and Org. Lett. 2013, 15, 3994-3997. Selected detailed synthesis examples of the compounds of the general formula (I) according to the invention are listed below. The 'H-NMR, 13 C-NMR and 19 F-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for' H-NMR and 150 MHz for 13 C-NMR and 375 MHz in "F-NMR, solvent CDCb, CD3OD or d6-DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) were obtained with a Bruker instrument and the designated signals have the meanings given below: br = broad (es); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, ., Me = CH 3 Et = CH2CH3, t-Hex = C (CH: dt = double triplet at diastereomers either the respective significant signals of both diastereomers, or the characteristic signal of the major diastereomer are specified, the abbreviations used for chemical groups example, have the following meanings. 3 ) 2CH (CH 3 ) 2, t-Bu = C (CH 3 ) 3 , n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-hex = cyclohexyl.
Synthesebeispiele: Synthesis Examples:
Synthesebeispiel No. 1-076: Synthesestufe 1 : 3-Methoxy-l,5-dimethyl-4-phenylsulfanyl-pyrazol (Intermediate No. A-28) Synthesis Example No. 1-076: Synthesis Step 1: 3-Methoxy-l, 5-dimethyl-4-phenylsulfanyl-pyrazole (Intermediate No. A-28)
5-Methyl-4-phenylsulfanyl-l,2-dihydropyrazol-3-on (7.46 g, 36.2 mmol, 1.0 equiv) wurde in Acetonitril (485 ml) gelöst und mit Kaliumcarbonat (15.0 g, 109 mmol, 3.0 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei 0 °C mit Dimethylsulfat (3.4 ml, 36.2 mmol, 1.0 equiv) versetzt, für 15 Minuten bei 0 °C und anschließend bei 70 °C für 45 Minuten gerührt. Das resultierende  5-Methyl-4-phenylsulfanyl-1,2-dihydropyrazol-3-one (7.46 g, 36.2 mmol, 1.0 equiv) was dissolved in acetonitrile (485 ml) and treated with potassium carbonate (15.0 g, 109 mmol, 3.0 equiv). Dimethyl sulfate (3.4 ml, 36.2 mmol, 1.0 equiv.) Was added to the resulting reaction mixture at 0 ° C., stirred for 15 minutes at 0 ° C. and then at 70 ° C. for 45 minutes. The resulting
Reaktionsgemisch wurde nochmals mit Dimethylsulfat (6.8 ml, 72.4 mmol, 2.0 equiv) versetzt und bei 70 °C für weitere 3 Stunden gerührt und anschließend wurde auf Raumtemperatur abgekühlt, Wasser und Dichlormethan zugegeben und nachfolgend die Phasen getrennt. Die wäßrige Phase wurde mehrfach mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach mit Wasser und ges. Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 3-Methoxy-l,5-dimethyl-4-phenylsulfanyl-pyrazol in Form eines farblosen Feststoffs isoliert werden (6.80 g, 80% der Theorie).  The reaction mixture was treated again with dimethyl sulfate (6.8 ml, 72.4 mmol, 2.0 equiv) and stirred at 70 ° C for a further 3 hours and then cooled to room temperature, added water and dichloromethane and then the phases were separated. The aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then washed with water and sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product allowed 3-methoxy-1,5-dimethyl-4-phenylsulfanyl-pyrazole to be isolated as a colorless solid (6.80 g, 80% of theory).
'H-NMR (400 MHz, CDC13 δ, ppm) 7.22-7.18 (m, 2H), 7.10-7.05 (m, 3H), 3.93 (s, 3H), 3.72 (s, 3H), 2.23 (s, 3H). 'H-NMR (400 MHz, CDC1 3 δ, ppm) 7.22-7.18 (m, 2H), 7.10-7.05 (m, 3H), 3.93 (s, 3H), 3.72 (s, 3H), 2.23 (s, 3H).
Synthesestufe 2: l,5-Dimethyl-4-phenylsulfanyl-pyrazol-3-ol (Intermediat No. A-24) Synthesis Step 2: 1, 5-Dimethyl-4-phenylsulfanyl-pyrazol-3-ol (Intermediate No. A-24)
3-Methoxy-l,5-dimethyl-4-phenylsulfanyl-pyrazol (6.80 g, 29.0 mmol, 1.0 equiv) wurde in Essigsäure (95 ml) gelöst und mit einer Lösung von 45% Bromwasserstoffsäure in Essigsäure (35.0 ml, 290 mmol, 10 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei 90 °C für 18 Stunden gerührt und anschließend auf Raumtemperatur abgekühlt und eingeengt. Der resultierende Feststoff wurde in Essigester gelöst, die Lösung mit Wasser und ges. Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende Urnkristallisierung (1 :1 Essigester:Methanol) des resultierenden Rohproduktes konnte l,5-Dimethyl-4-phenylsulfanyl-pyrazol- 3-ol in Form eines farblosen Feststoffs isoliert werden (3.12 g, 49% der Theorie). 3-Methoxy-l, 5-dimethyl-4-phenylsulfanyl-pyrazole (6.80 g, 29.0 mmol, 1.0 equiv) was dissolved in acetic acid (95 ml) and washed with a solution of 45% hydrobromic acid in acetic acid (35.0 ml, 290 mmol, 10 equiv). The resulting reaction mixture was stirred at 90 ° C for 18 hours and then cooled to room temperature and concentrated. The resulting solid was dissolved in ethyl acetate, the solution washed with water and sat. Washed sodium chloride solution, over Dried magnesium sulfate, filtered and concentrated. By final Urnkristallisierung (1: 1 ethyl acetate: methanol) of the resulting crude product was l, 5-dimethyl-4-phenylsulfanyl-pyrazol-3-ol in the form of a colorless solid isolated (3.12 g, 49% of theory).
'H-NMR (400 MHz, de-DMSO δ, ppm) 10.04 (s, 1H), 7.26-7.22 (m, 2H), 7.10-7.06 (m, 1H), 7.00-6.98 (m, 2H), 3.60 (s, 3H), 2.15 (s, 3H). 'H-NMR (400 MHz, de-DMSO δ, ppm) 10.04 (s, 1H), 7.26-7.22 (m, 2H), 7.10-7.06 (m, 1H), 7.00-6.98 (m, 2H), 3.60 (s, 3H), 2.15 (s, 3H).
Synthesestufe 3: 2-(l,5-Dimethyl-4-phenylsulfanyl-pyrazol-3-yl)oxypyrimidin (Synthesebeispiel No. I- 076): Synthesis step 3: 2- (l, 5-dimethyl-4-phenylsulfanyl-pyrazol-3-yl) oxypyrimidine (Synthesis Example No. I-076):
Unter Argon wurden l,5-Dimethyl-4-phenylsulfanyl-pyrazol-3-ol (300 mg, 1.36 mmol, 1.0 equiv) und 2-Chlorpyrimidin (156 mg, 1.36 mmol, 1.0 equiv) in wasserfreiem Dimethylformamid (5 ml) gelöst und mit Cäsiumcarbonat (890 mg, 2.72 mmol, 2.0 equiv) und Kupfer(I)-Iodid (25.9 mg, 0.136 mmol, 0.1 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei 100 °C für 6 Stunden gerührt und anschließend auf Raumtemperatur abgekühlt, Essigester und Wasser zugegeben und nachfolgend die Phasen getrennt. Die wäßrige Phase wurde mehrfach mit Essigester extrahiert, und die vereinigten organischen Phasen wurden danach mit Wasser (x3) und ges. Natriumchloridlösung (xl) gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende  Under argon were dissolved l, 5-dimethyl-4-phenylsulfanyl-pyrazol-3-ol (300 mg, 1.36 mmol, 1.0 equiv) and 2-chloropyrimidine (156 mg, 1.36 mmol, 1.0 equiv) in anhydrous dimethylformamide (5 ml) and cesium carbonate (890 mg, 2.72 mmol, 2.0 equiv) and copper (I) iodide (25.9 mg, 0.136 mmol, 0.1 equiv) were added. The resulting reaction mixture was stirred at 100 ° C for 6 hours and then cooled to room temperature, ethyl acetate and water were added and then the phases were separated. The aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were then washed with water (x3) and sat. Sodium chloride solution (xl), dried over magnesium sulfate, filtered and concentrated. By final
säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 2-(l,5-Dimethyl-4-phenylsulfanyl-pyrazol-3-yl)oxypyrimidin in Form eines gelben Öls isoliert werden (170 mg, 43% der Theorie). purified by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product, 2- (l, 5-dimethyl-4-phenylsulfanyl-pyrazol-3-yl) oxypyrimidine was isolated as a yellow oil (170 mg, 43% of theory).
'H-NMR (400 MHz, CDC13 δ, ppm) 8.44 (d, 2H), 7.17-7.13 (m, 2H), 7.09-7.04 (m, 3H), 6.96 (t, 1H), 3.83 (s, 3H), 2.30 (s, 3H). 'H-NMR (400 MHz, CDC1 3 δ, ppm) 8.44 (d, 2H), 7.17-7.13 (m, 2H), 7.09-7.04 (m, 3H), 6.96 (t, 1H), 3.83 (s, 3H), 2.30 (s, 3H).
Synthesebeispiel No. 1-028: Synthesis Example No. 1-028:
Synthesestufe 1 : 4-(2,4-Difluorphenoxy)-3-methoxy-l ,5-dimethylpyrazol (Intermediat No. A-33) Synthesis Stage 1: 4- (2,4-Difluorophenoxy) -3-methoxy-1,1-dimethylpyrazole (Intermediate No. A-33)
Analog zur Synthese von 3-Methoxy-l,5-dimethyl-4-phenylsulfanyl-pyrazol wurden aus 5.37 g 4-(2,4- Difluorphenoxy)-5-methyl-l,2-dihydropyrazol-3-on 2.35 g (39%) 4-(2,4-Difluorphenoxy)-3-methoxy- 1,5-dimethylpyrazol erhalten. Analogous to the synthesis of 3-methoxy-l, 5-dimethyl-4-phenylsulfanyl-pyrazole were from 5.37 g of 4- (2,4-difluorophenoxy) -5-methyl-l, 2-dihydropyrazol-3-one 2.35 g (39 %) 4- (2,4-difluorophenoxy) -3-methoxy-1,5-dimethylpyrazole.
'H-NMR (400 MHz, CDC13 δ, ppm) 7.11-7.05 (m, 1H), 6.88-6.83 (m, 1H), 6.76-6.70 (m, 1H), 3.34 (s, 3H), 3.17 (s, 3H), 2.14 (s, 3H). 'H NMR (400 MHz, CDCl3 3 δ, ppm) 7.11-7.05 (m, 1H), 6.88-6.83 (m, 1H), 6.76-6.70 (m, 1H), 3.34 (s, 3H), 3.17 ( s, 3H), 2.14 (s, 3H).
Synthesestufe 2: 4-(2,4-Difluorphenoxy)-l,5-dimethyl-pyrazol-3-ol (Intermediat No. A-23) Synthesis step 2: 4- (2,4-Difluorophenoxy) -1,1-dimethylpyrazol-3-ol (Intermediate No. A-23)
Analog zur Synthese von l,5-Dimethyl-4-phenylsulfanyl-pyrazol-3-ol wurden aus 2.35 g 4-(2,4- Difluorphenoxy)-3-methoxy-l,5-dimethylpyrazol 2.93 g 4-(2,4-Difluorphenoxy)-l,5-dimethyl-pyrazol- 3-ol mit etwas Essigsäure erhalten. Analogously to the synthesis of l, 5-dimethyl-4-phenylsulfanyl-pyrazol-3-ol, 2.35 g of 4- (2,4-difluorophenoxy) -3-methoxy-1,5-dimethylpyrazole gave 2.93 g of 4- (2,4 -Difluorophenoxy) -l, 5-dimethyl-pyrazol-3-ol with a little acetic acid.
'H-NMR (400 MHz, CDCI3 δ, ppm) 6.98-6.84 (m, 2H), 6.77-6.70 (m, 1H), 3.56 (s, 3H), 2.12 (s, 3H).  'H NMR (400 MHz, CDCl3 δ, ppm) 6.98-6.84 (m, 2H), 6.77-6.70 (m, 1H), 3.56 (s, 3H), 2.12 (s, 3H).
Synthesestufe 3: 2-[4-(2,4-Difluorphenoxy)-l,5-dimethyl-pyrazol-3-yl]oxy-5-fluorpyrimidin Synthesis step 3: 2- [4- (2,4-Difluorophenoxy) -1, 5-dimethyl-pyrazol-3-yl] oxy-5-fluoropyrimidine
(Synthesebeispiel No. 1-028): (Synthesis Example No. 1-028):
Analog zur Synthese von 2-(l,5-Dimethyl-4-phenylsulfanyl-pyrazol-3-yl)oxypyrimidin wurden aus 150 mg 4-(2,4-Difluorphenoxy)-l,5-dimethyl-pyrazol-3-ol 97 mg (46%>) 2-[4-(2,4-Difluorphenoxy)-l,5- dimethyl-pyrazol-3-yl]oxy-5-fluorpyrimidin erhalten. Analogously to the synthesis of 2- (l, 5-dimethyl-4-phenylsulfanyl-pyrazol-3-yl) oxypyrimidine were from 150 mg of 4- (2,4-difluorophenoxy) -l, 5-dimethyl-pyrazol-3-ol 97 mg (46%) of 2- [4- (2,4-difluorophenoxy) -1,5-dimethylpyrazol-3-yl] oxy-5-fluoropyrimidine.
'H-NMR (400 MHz, CDCI3 δ, ppm) 8.34 (s, 2H), 6.97-6.93 (m, 1H), 6.80-6.77 (m, 1H), 6.69-6.66 (m, 1H), 3.76 (s, 3H), 2.21 (s, 3H). Synthesebeispiel No. 1-016: 'H NMR (400 MHz, CDCl3 δ, ppm) 8.34 (s, 2H), 6.97-6.93 (m, 1H), 6.80-6.77 (m, 1H), 6.69-6.66 (m, 1H), 3.76 (s , 3H), 2.21 (s, 3H). Synthesis Example No. 1-016:
Synthesestufe 1 : 4-[(4-Fluorphenyl)methyl]-3-methoxy-l,5-dimethylpyrazol (Intermediat No. A-22) Synthesis step 1: 4 - [(4-fluorophenyl) methyl] -3-methoxy-l, 5-dimethylpyrazole (Intermediate No. A-22)
4-[(4-Fluorphenyl)methyl]-5-methyl-l,2-dihydropyrazol-3-on (7.60 g, 37.0 mmol, 1.0 equiv) wurde in Acetonitril (220 ml) gelöst und mit Kaliumcarbonat (12.8 g, 92.9 mmol, 2.4 equiv) versetzt. Das resultierende Reaktionsgemisch wurde auf eine Temperatur von 0 °C abgekühlt, mit Dimethylsulfat (5.49 ml, 58.1 mmol, 1.5 equiv) versetzt und anschließend für 30 Minuten bei 0 °C und danach bei Raumtemperatur für 18 Stunden gerührt. Wasser wurde zugegeben, die wäßrige Phase mehrfach mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über 4 - [(4-Fluorophenyl) methyl] -5-methyl-1,2-dihydropyrazol-3-one (7.60 g, 37.0 mmol, 1.0 equiv) was dissolved in acetonitrile (220 ml) and washed with potassium carbonate (12.8 g, 92.9 mmol, 2.4 equiv). The resulting reaction mixture was cooled to a temperature of 0 ° C, added with dimethyl sulfate (5.49 ml, 58.1 mmol, 1.5 equiv) and then stirred for 30 minutes at 0 ° C and then at room temperature for 18 hours. Water was added, the aqueous phase extracted several times with dichloromethane, and the combined organic phases were then transferred
Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 4-[(4- Fluorphenyl)methyl]-3-methoxy-l,5-dimethylpyrazol isoliert werden (720 mg, 8% der Theorie). 'H-NMR (400 MHz, CDC13 δ, ppm) 7.13-7.10 (m, 2H), 6.94-6.90 (m, 2H), 3.88 (s, 3H), 3.62 (s, 3H), 3.60 (s, 2H), 2.06 (s, 3H). Dried magnesium sulfate, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product afforded 4 - [(4-fluorophenyl) methyl] -3-methoxy-1,5-dimethylpyrazole (720 mg, 8% of theory). 'H NMR (400 MHz, CDC1 3 δ, ppm) 7.13-7.10 (m, 2H), 6.94-6.90 (m, 2H), 3.88 (s, 3H), 3.62 (s, 3H), 3.60 (s, 2H), 2.06 (s, 3H).
Synthesestufe 2: 4-[(4-Fluorphenyl)methyl]-l,5-dimethylpyrazol-3-ol (Intermediat No. A-21) Synthesis step 2: 4 - [(4-fluorophenyl) methyl] -1,5-dimethylpyrazol-3-ol (Intermediate No. A-21)
4-[(4-Fluorphenyl)methyl]-3-methoxy-l,5-dimethylpyrazol (710 mg, 3.03 mmol, 1.0 equiv) wurde in Essigsäure (9 ml) gelöst und mit einer Lösung von 45% Bromwasserstoffsäure in Essigsäure (3.7 ml, 30.3 mmol, 10 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei 140 °C für 8 Stunden gerührt und anschließend auf Raumtemperatur abgekühlt und eingeengt. Der resultierende Feststoff wurde in Essigester gelöst, die Lösung mit Wasser und ges. Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Auf diese Weise erhält man 4-[(4- Fluorphenyl)methyl]-l,5-dimethylpyrazol-3-ol (450 mg, 67% der Theorie). 'H-NMR (400 MHz, CDC13 δ, ppm) 7.18-7.15 (m, 2H), 6.96-6.91 (m, 2H), 3.65 (s, 2H), 3.62 (s, 3H), 2.07 (s, 3H). 4 - [(4-Fluorophenyl) methyl] -3-methoxy-l, 5-dimethylpyrazole (710mg, 3.03mmol, 1.0 equiv.) Was dissolved in acetic acid (9mL) and treated with a solution of 45% hydrobromic acid in acetic acid (3.7 ml, 30.3 mmol, 10 equiv). The resulting reaction mixture was stirred at 140 ° C for 8 hours and then cooled to room temperature and concentrated. The resulting solid was dissolved in ethyl acetate, the solution washed with water and sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. This gives 4 - [(4-fluorophenyl) methyl] -1,5-dimethylpyrazol-3-ol (450 mg, 67% of theory). 'H NMR (400 MHz, CDC1 3 δ, ppm) 7.18-7.15 (m, 2H), 6.96-6.91 (m, 2H), 3.65 (s, 2H), 3.62 (s, 3H), 2.07 (s, 3H).
Synthesestufe 3: 5-Fluor-2-[4-[(4-fluorphenyl)methyl]-l,5-dimethylpyrazol-3-yl]oxypyrimidin Synthesis step 3: 5-Fluoro-2- [4 - [(4-fluorophenyl) methyl] -1,5-dimethylpyrazol-3-yl] oxypyrimidine
(Synthesebeispiel No. 1-016): (Synthesis Example No. 1-016):
Analog zur Synthese von 2-(l,5-Dimethyl-4-phenylsulfanyl-pyrazol-3-yl)oxypyrimidin wurden aus 145 mg 4-[(4-Fluorphenyl)methyl]-l,5-dimethylpyrazol-3-ol 93 mg (45%) 5-Fluor-2-[4-[(4- fluorphenyl)methyl]-l,5-dimethylpyrazol-3-yl]oxypyrimidin erhalten.  Analogously to the synthesis of 2- (l, 5-dimethyl-4-phenylsulfanyl-pyrazol-3-yl) oxypyrimidine, 145 mg of 4 - [(4-fluorophenyl) methyl] -1,5-dimethylpyrazol-3-ol gave 93 mg (45%) 5-Fluoro-2- [4 - [(4-fluorophenyl) methyl] -1,5-dimethylpyrazol-3-yl] oxypyrimidine.
'H-NMR (400 MHz, CDCI3 δ, ppm) 8.32 (s, 2H), 7.06-7.03 (m, 2H), 6.87-6.82 (m, 2H), 3.74 (s, 3H), 3.59 (s, 2H), 2.16 (s, 3H).  'H NMR (400 MHz, CDCl3 δ, ppm) 8.32 (s, 2H), 7.06-7.03 (m, 2H), 6.87-6.82 (m, 2H), 3.74 (s, 3H), 3.59 (s, 2H ), 2.16 (s, 3H).
Synthesebeispiel No. 1-198: Synthesis Example No. 1-198:
Synthesestufe 1 : 2-[(4-Methoxyphenyl)methyl]-5-methyl-4-phenylsulfanyl-pyrazol-3-ol (Intermediat No. A-20 Synthesis step 1: 2 - [(4-Methoxyphenyl) methyl] -5-methyl-4-phenylsulfanyl-pyrazol-3-ol (Intermediate No. A-20
Ethyl (£)-3-hydroxy-2-phenylsulfanyl-but-2-enoat (9.16 g, 38.4 mmol, 1.0 equiv) wurde in Ethanol (65 ml) gelöst und mit (4-Methoxyphenyl)hydrazin (7.96 g, 57.6 mmol, 1.5 equiv) versetzt. Das resultierende Reaktionsgemisch wurde für 2 Stunden bei 90 °C gerührt und anschließend auf Ethyl ()) -3-hydroxy-2-phenylsulfanyl-but-2-enoate (9.16 g, 38.4 mmol, 1.0 equiv) was dissolved in ethanol (65 ml) and washed with (4-methoxyphenyl) hydrazine (7.96 g, 57.6 mmol , 1.5 equiv). The resulting reaction mixture was stirred for 2 hours at 90 ° C and then auf
Raumtemperatur abgekühlt, eingeengt und Wasser und Essigester zugegeben. Der resultierende Feststoff wurde ab filtriert und mit Wasser und Essigester gewaschen. Auf diese Weise erhält man 2-[(4- Methoxyphenyl)methyl]-5-methyl-4-phenylsulfanyl-pyrazol-3-ol (9.30 g, 74% der Theorie) in Form eines farblosen Feststoffs. Cooled room temperature, concentrated and added water and ethyl acetate. The resulting solid was filtered off and washed with water and ethyl acetate. In this way 2 - [(4-methoxyphenyl) methyl] -5-methyl-4-phenylsulfanyl-pyrazol-3-ol (9.30 g, 74% of theory) is obtained in the form of a colorless solid.
'H-NMR (400 MHz, de-DMSO δ, ppm) 7.27-7.23 (m, 2H), 7.16-7.07 (m, 3H), 6.99-6.89 (m, 4H), 4.99 (s, 2H), 3.73 (s, 3H), 1.98 (s, 3H). Synthesestufe 2 : 2- [2- [(4-Methoxyphenyl)methyl] -5-methyl-4-phenylsulfanyl-pyrazol-3 - yl]oxypyrimidin (Intermediat No. A-18) 'H-NMR (400 MHz, de-DMSO δ, ppm) 7.27-7.23 (m, 2H), 7.16-7.07 (m, 3H), 6.99-6.89 (m, 4H), 4.99 (s, 2H), 3.73 (s, 3H), 1.98 (s, 3H). Synthesis step 2: 2- [2- [(4-methoxyphenyl) methyl] -5-methyl-4-phenylsulfanyl-pyrazol-3-yl] oxypyrimidine (Intermediate No. A-18)
2-[(4-Methoxyphenyl)methyl]-5-methyl-4-phenylsulfanyl-pyrazol-3-ol (4.45 g, 13.6 mmol, 1.0 equiv) wurde in Butyronitril (45 ml) gelöst und mit 2-Chlorpyrimidin (3.12 g, 27.3 mmol, 2.0 equiv) und Caesiumcarbonat (7.55 g, 23.2 mmol, 1.7 equiv) versetzt. Das resultierende Reaktionsgemisch wurde für 8 Stunden bei 160 °C gerührt und anschließend auf Raumtemperatur abgekühlt, eingeengt und Wasser zugegeben. Die wäßrige Phase wurde mehrfach mit Essigester extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 2-[2-[(4-Methoxyphenyl)methyl]-5-methyl-4-phenylsulfanyl-pyrazol-3- yl]oxypyrimidin isoliert werden (5.23 g, 95% der Theorie). 2 - [(4-Methoxyphenyl) methyl] -5-methyl-4-phenylsulfanyl-pyrazol-3-ol (4.45 g, 13.6 mmol, 1.0 equiv.) Was dissolved in butyronitrile (45 ml) and extracted with 2-chloropyrimidine (3.12 g , 27.3 mmol, 2.0 equiv) and cesium carbonate (7.55 g, 23.2 mmol, 1.7 equiv). The resulting reaction mixture was stirred for 8 hours at 160 ° C and then cooled to room temperature, concentrated and water was added. The aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product afforded 2- [2 - [(4-methoxyphenyl) methyl] -5-methyl-4-phenylsulfanyl-pyrazol-3-yl] oxypyrimidine (5.23 g, 95 % of theory).
'H-NMR (400 MHz, CDC13 δ, ppm) 8.37 (d, 2H), 7.20-7.12 (m, 4H), 7.06-6.98 (m, 4H), 6.77-6.75 (m, 2H), 5.15 (s, 2H), 3.75 (s, 3H), 2.22 (s, 3H). 'H NMR (400 MHz, CDC1 3 δ, ppm) 8.37 (d, 2H), 7.20-7.12 (m, 4H), 7.06-6.98 (m, 4H), 6.77-6.75 (m, 2H), 5.15 ( s, 2H), 3.75 (s, 3H), 2.22 (s, 3H).
Synthesestufe 3: 2-[(5-Methyl-4-phenylsulfanyl-lH-pyrazol-3-yl)oxy]pyrimidin Synthesis step 3: 2 - [(5-methyl-4-phenylsulfanyl-1H-pyrazol-3-yl) oxy] pyrimidine
2- [2- [(4-Methoxyphenyl)methyl] -5-methyl-4-phenylsulfanyl-pyrazol-3 -yl] oxypyrimidin (5.59 g, 13.8 mmol, 1.0 equiv) wurde in Trifluoressigsaeure (37 ml) gelöst, für 2 Stunden bei 50 °C gerührt und anschließend auf Raumtemperatur abgekühlt und eingeengt. Durch abschließende  2- [2- [(4-Methoxyphenyl) methyl] -5-methyl-4-phenylsulfanyl-pyrazol-3-yl] oxypyrimidine (5.59 g, 13.8 mmol, 1.0 equiv) was dissolved in trifluoroacetic acid (37 ml) for 2 Stirred at 50 ° C for hours and then cooled to room temperature and concentrated. By final
säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 2-[(5-Methyl-4-phenylsulfanyl-lH-pyrazol-3-yl)oxy]pyrimidin isoliert werden (3.61 g, 90% der Theorie). purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product, 2 - [(5-methyl-4-phenylsulfanyl-1H-pyrazol-3-yl) oxy] pyrimidine was isolated (3.61 g, 90% of theory).
'H-NMR (400 MHz, CDCI3 δ, ppm) 8.45 (d, 2H), 7.17-7.13 (m, 2H), 7.07-7.03 (m, 3H), 6.98 (t, 1H), 2.29 (s, 3H). Synthesestufe 4: 2-(l -Ethyl-5-methyl-4-phenylsulfanyl-pyrazol-3-yl)oxypyrimidin (Synthesebeispiel No. 1-198): 'H NMR (400 MHz, CDCl3 δ, ppm) 8.45 (d, 2H), 7.17-7.13 (m, 2H), 7.07-7.03 (m, 3H), 6.98 (t, 1H), 2.29 (s, 3H ). Synthesis step 4: 2- (1-ethyl-5-methyl-4-phenylsulfanyl-pyrazol-3-yl) -oxypyrimidine (Synthesis Example No. 1-198):
2-[(5-Methyl-4-phenylsulfanyl-lH-pyrazol-3-yl)oxy]pyrimidin (150 mg, 0.53 mmol, 1.0 equiv) wurde in Acetonitril (3 ml) gelöst und mit Caesiumcarbonat (206 mg, 0.63 mmol, 1.2 equiv) und Iodethan (166 mg, 1.06 mmol, 2.0 equiv) versetzt. Das resultierende Reaktionsgemisch wurde für 1 Stunde bei Raumtemperatur gerührt und anschließend 2M Ammoniakwasser gegeben. Die wäßrige Phase wurde mehrfach mit Essigester extrahiert, und die vereinigten organischen Phasen wurden danach mit ges. Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 2-(l-Ethyl-5-methyl-4-phenylsulfanyl-pyrazol-3-yl)oxypyrimidin isoliert werden (106 mg, 64% der Theorie). 2 - [(5-Methyl-4-phenylsulfanyl-1H-pyrazol-3-yl) oxy] pyrimidine (150 mg, 0.53 mmol, 1.0 equiv) was dissolved in acetonitrile (3 ml) and washed with cesium carbonate (206 mg, 0.63 mmol 1.2 equiv) and iodoethane (166 mg, 1.06 mmol, 2.0 equiv). The resulting reaction mixture was stirred for 1 hour at room temperature and then added to 2M ammonia water. The aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were then washed with sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product afforded 2- (1-ethyl-5-methyl-4-phenylsulfanyl-pyrazol-3-yl) -oxypyrimidine (106 mg, 64% of theory).
'H-NMR (400 MHz, CDC13 δ, ppm) 8.43 (d, 2H), 7.17-7.13 (m, 2H), 7.08-7.03 (m, 3H), 6.95 (t, 1H), 4.13 (q, 2H), 2.31 (s, 3H), 1.48 (t, 3H). 'H-NMR (400 MHz, CDCl3 3 δ, ppm) 8.43 (d, 2H), 7.17-7.13 (m, 2H), 7.08-7.03 (m, 3H), 6.95 (t, 1H), 4.13 (q, 2H), 2.31 (s, 3H), 1.48 (t, 3H).
Synthesebeispiel No. 1-053: Tert-butyl-5-methyl-4-phenylsulfanyl-3-pyrimidin-2-yloxy-pyrazole-l-carboxylat Synthesis Example No. 1-053: Tert-butyl-5-methyl-4-phenylsulfanyl-3-pyrimidin-2-yloxy-pyrazole-1-carboxylate
2-[(5-Methyl-4-phenylsulfanyl-lH-pyrazol-3-yl)oxy]pyrimidin (150 mg, 0.53 mmol, 1.0 equiv) wurde in Tetrahydrofuran (3 ml) gelöst und mit Di-tert-butyldicarbonat (138 mg, 0.63 mmol, 1.2 equiv) und Triethylamin (0.11 ml, 0.79 mmol, 1.5 equiv) versetzt. Das resultierende Reaktionsgemisch wurde für 18 Stunden bei Raumtemperatur gerührt und anschließend mit Essigester verdünnt, mit ges.  2 - [(5-Methyl-4-phenylsulfanyl-1H-pyrazol-3-yl) oxy] pyrimidine (150 mg, 0.53 mmol, 1.0 equiv) was dissolved in tetrahydrofuran (3 ml) and treated with di-tert-butyl dicarbonate (138 mg, 0.63 mmol, 1.2 equiv) and triethylamine (0.11 ml, 0.79 mmol, 1.5 equiv). The resulting reaction mixture was stirred for 18 hours at room temperature and then diluted with ethyl acetate, washed with sat.
Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte Tert-butyl-5-methyl-4-phenylsulfanyl-3-pyrimidin-2-yloxy-pyrazole-l-carboxylat isoliert werden (171 mg, 84% der Theorie). Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. By final column chromatographic purification (gradient ethyl acetate / heptane) of the resulting Crude product was tert-butyl-5-methyl-4-phenylsulfanyl-3-pyrimidin-2-yloxy-pyrazole-l-carboxylate isolated (171 mg, 84% of theory).
'H-NMR (400 MHz, CDC13 δ, ppm) 8.42 (d, 2H), 7.19-7.15 (m, 2H), 7.11-7.06 (m, 3H), 6.98 (t, 1H), 2.63 (s, 3H), 1.65 (s, 9H). 'H-NMR (400 MHz, CDC1 3 δ, ppm) 8.42 (d, 2H), 7.19-7.15 (m, 2H), 7.11-7.06 (m, 3H), 6.98 (t, 1H), 2.63 (s, 3H), 1.65 (s, 9H).
Synthesebeispiel No. 1-129: Synthesis Example No. 1-129:
2- [ 1 -(Difluormethyl)-5-methyl-4-phenylsulfanyl-pyrazol-3 -yl] oxypyrimidin 2- [1- (Difluoromethyl) -5-methyl-4-phenylsulfanyl-pyrazol-3-yl] oxypyrimidine
Unter Argon wurde 2-[(5-Methyl-4-phenylsulfanyl-lH-pyrazol-3-yl)oxy]pyrimidin (150 mg, 0.53 mmol, 1.0 equiv) in wasserfreiem Dimethylformamid (2 ml) gelöst und mit Ethyl 2-chloro-2,2- difluoracetat (100 mg, 0.63 mmol, 1.2 equiv) und Kaliumcarbonat (146 mg, 1.06 mmol, 2.0 equiv) versetzt. Das resultierende Reaktionsgemisch wurde für 12 Stunden bei 60 °C und danach für 6 Stunden bei 140 °C gerührt und anschließend auf Raumtemperatur abgekühlt und Wasser zugegeben. Die wäßrige Phase wurde mehrfach mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 2-[l-(Difluormethyl)-5-methyl-4-phenylsulfanyl-pyrazol-3-yl]oxypyrimidin isoliert werden (17 mg, 10% der Theorie).  Under argon, 2 - [(5-methyl-4-phenylsulfanyl-1H-pyrazol-3-yl) oxy] pyrimidine (150 mg, 0.53 mmol, 1.0 equiv) was dissolved in anhydrous dimethylformamide (2 ml) and extracted with ethyl 2-chloro -2,2-difluoroacetate (100 mg, 0.63 mmol, 1.2 equiv) and potassium carbonate (146 mg, 1.06 mmol, 2.0 equiv) were added. The resulting reaction mixture was stirred for 12 hours at 60 ° C and then for 6 hours at 140 ° C and then cooled to room temperature and water was added. The aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product afforded 2- [1- (difluoromethyl) -5-methyl-4-phenylsulfanyl-pyrazol-3-yl] oxypyrimidine (17 mg, 10% of theory).
'H-NMR (400 MHz, CDCI3 δ, ppm) 8.43 (d, 2H), 7.21-7.07 (m, 6H), 7.00 (t, 1H), 2.52 (s, 3H).  'H NMR (400 MHz, CDCl3 δ, ppm) 8.43 (d, 2H), 7.21-7.07 (m, 6H), 7.00 (t, 1H), 2.52 (s, 3H).
Synthesebeispiel No. 1-044: Synthesis Example No. 1-044:
S nthesestufe 1 : 2-(l,5-Dimethylpyrazol-3-yl)oxypyrimidin (Intermediat No. A-01) Synthesis step 1: 2- (l, 5-dimethylpyrazol-3-yl) oxypyrimidine (Intermediate No. A-01)
l,5-Dimethyl-lH-pyrazol-3-olhydrochlorid (3.68 g, 24.8 mmol, 1.0 equiv) wurde in Acetonitril (100 ml) gelöst und mit 2-Chlorpyrimidin (2.84 g, 24.8 mmol, 1.0 equiv), Caesiumcarbonat (28.2 g, 86.7 mmol, 3.5 equiv) und Kupfer(I)-iodid (0.36 g, 4.95 mmol, 0.2 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei 80 °C für 3 Stunden gerührt und anschließend auf Raumtemperatur abgekühlt, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 2-(l,5-Dimethylpyrazol-3-yl)oxypyrimidin in Form eines braunen Öls isoliert werden (2.68 g, 55% der Theorie). 1, 5-Dimethyl-1H-pyrazol-3-ol hydrochloride (3.68 g, 24.8 mmol, 1.0 equiv) was dissolved in acetonitrile (100 ml) and treated with 2-chloropyrimidine (2.84 g, 24.8 mmol, 1.0 equiv), cesium carbonate (28.2 g, 86.7 mmol, 3.5 equiv) and copper (I) iodide (0.36 g, 4.95 mmol, 0.2 equiv). The resulting reaction mixture was stirred at 80 ° C for 3 hours and then cooled to room temperature, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product afforded 2- (l, 5-dimethylpyrazol-3-yl) oxypyrimidine as a brown oil (2.68 g, 55% of theory).
'H-NMR (400 MHz, CDC13 δ, ppm) 8.59 (d, 2H), 7.04 (t, 1H), 5.83 (s, 1H), 3.74 (s, 3H), 2.29 (s, 3H). 'H-NMR (400 MHz, CDC1 3 δ, ppm) 8.59 (d, 2H), 7.04 (t, 1H), 5.83 (s, 1H), 3.74 (s, 3H), 2.29 (s, 3H).
S nthesestufe 2: 2-(4-Iod-l,5-dimethyl-pyrazol-3-yl)oxypyrimidin (Intermediat No. A-08) Synthesis step 2: 2- (4-iodo-1, 5-dimethyl-pyrazol-3-yl) oxypyrimidine (Intermediate No. A-08)
2-(l,5-Dimethylpyrazol-3-yl)oxypyrimidin (4.00 g, 21.0 mmol, 1.0 equiv) wurde in Acetonitril (120 ml) gelöst und mit lod (3.20 g, 12.6 mmol, 0.6 equiv) und Ammoniumcer(IV)-nitrat (6.92 g, 12.6 mmol, 0.6 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei Raumtemperatur für 3 Stunden gerührt und anschließend eingeengt. Der resultierende Öl wurde in Dichlormethan gelöst, die Lösung mit 10% wassrigem Natriumthiosulfat gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Auf diese Weise erhält man 2-(4-Iod-l,5-dimethyl-pyrazol-3-yl)oxypyrimidin  2- (l, 5-dimethylpyrazol-3-yl) oxypyrimidine (4.00 g, 21.0 mmol, 1.0 equiv) was dissolved in acetonitrile (120 mL) and washed with iodine (3.20 g, 12.6 mmol, 0.6 equiv) and ammonium ccer (IV). nitrate (6.92 g, 12.6 mmol, 0.6 equiv). The resulting reaction mixture was stirred at room temperature for 3 hours and then concentrated. The resulting oil was dissolved in dichloromethane, the solution washed with 10% aqueous sodium thiosulfate, dried over magnesium sulfate, filtered and concentrated. In this way, 2- (4-iodo-l, 5-dimethyl-pyrazol-3-yl) oxypyrimidine is obtained
(5.92 g, 85%o der Theorie) in Form eines braunen Öls. (5.92 g, 85% of theory) in the form of a brown oil.
'H-NMR (400 MHz, CDCI3 δ, ppm) 8.60 (d, 2H), 7.07 (t, 1H), 3.83 (s, 3H), 2.33 (s, 3H).  'H NMR (400 MHz, CDCl3 δ, ppm) 8.60 (d, 2H), 7.07 (t, 1H), 3.83 (s, 3H), 2.33 (s, 3H).
Synthesestufe 3: 2-[4-(2,4-Difluorphenyl)sulfanyl-l,5-dimethyl-pyrazol-3-yl]oxypyrimidin Synthesis step 3: 2- [4- (2,4-Difluorophenyl) sulfanyl-l, 5-dimethyl-pyrazol-3-yl] oxypyrimidine
(S nthesebeispiel No. 1-044): (Reference Example No. 1-044):
Unter Argon wurde 2,4-Difluorthiophenol (104 mg, 0.71 mmol, 1.5 equiv) in wasserfreiem  Under argon, 2,4-difluorothiophenol (104 mg, 0.71 mmol, 1.5 equiv) in anhydrous
Dimethylformamid (4 ml) gelöst, auf eine Temperatur von 0 °C abgekühlt und mit Natriumhydrid (60%> in Öl, 28 mg, 0.71 mmol, 1.5 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei 0 °C für 10 Minuten gerührt und anschließend mit 2-(4-Iod-l,5-dimethyl-pyrazol-3-yl)oxypyrimidin (150 mg, 0.48 mmol, 1.0 equiv) und Kupfer(I)-iodid (90 mg, 0.48 mmol, 1.0 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei 80 °C für 6 Stunden gerührt und anschließend auf Raumtemperatur abgekühlt und mit Wasser versetzt. Die wäßrige Phase wurde mehrfach mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 2-[4-(2,4-Difluorphenyl)sulfanyl-l,5-dimethyl-pyrazol-3- yl]oxypyrimidin in Form eines gelben Öls isoliert werden (124 mg, 74% der Theorie). Dissolved dimethylformamide (4 ml), cooled to a temperature of 0 ° C and treated with sodium hydride (60%> in oil, 28 mg, 0.71 mmol, 1.5 equiv). The resulting reaction mixture was stirred at 0 ° C for 10 minutes and then with 2- (4-iodo-l, 5-dimethyl-pyrazol-3-yl) oxypyrimidine (150 mg, 0.48 mmol, 1.0 equiv) and copper (I). iodide (90 mg, 0.48 mmol, 1.0 equiv). The resulting reaction mixture was stirred at 80 ° C for 6 hours and then to room temperature cooled and mixed with water. The aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product afforded 2- [4- (2,4-difluorophenyl) sulfanyl-1,5-dimethyl-pyrazol-3-yl] oxypyrimidine as a yellow oil (124 mg, 74% of theory).
'H-NMR (400 MHz, CDC13 δ, ppm) 8.50 (d, 2H), 7.09-7.01 (m, 2H), 6.74-6.67 (m, 2H), 3.82 (s, 3H), 2.35 (s, 3H). 'H-NMR (400 MHz, CDC1 3 δ, ppm) 8.50 (d, 2H), 7.09-7.01 (m, 2H), 6.74-6.67 (m, 2H), 3.82 (s, 3H), 2.35 (s, 3H).
Synthesebeispiel No. 1-077: Synthesis Example No. 1-077:
Synthesestufe 1 : Methyl- l-methyl-3-(pyrimidin-2-yloxy)-lH-pyrazo 1-5 -carboxylat (Intermediat No. A- 02 Synthesis step 1: Methyl 1-methyl-3- (pyrimidin-2-yloxy) -1H-pyrazole 1-5-carboxylate (Intermediate No. A-02
Methyl-3-hydroxy-l-methyl-lH-pyrazo 1-5 -carboxylat (1.50 g, 9.61 mmol, 1.0 equiv) wurde in Dimethylformamid (48 ml) gelöst und mit 2-Chlorpyrimidin (1.10 g, 9.61 mmol, 1.0 equiv), Methyl 3-hydroxy-1-methyl-1H-pyrazole 1-5-carboxylate (1.50 g, 9.61 mmol, 1.0 equiv) was dissolved in dimethylformamide (48 ml) and extracted with 2-chloropyrimidine (1.10 g, 9.61 mmol, 1.0 equiv )
Caesiumcarbonat (6.26 g, 19.2 mmol, 2.0 equiv) und Kupfer(I)-iodid (140 mg, 1.92 mmol, 0.2 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei 80 °C für 3 Stunden gerührt und anschließend auf Raumtemperatur abgekühlt und Essigester zugegeben. Die organische Phase wurde mit Wasser gewachen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Der resultierende Feststoff wurde in Heptan suspendiert, gerührt und anschließend ab filtriert. Auf diese Weise erhält man Methyl- 1- methyl-3-(pyrimidin-2-yloxy)-lH-pyrazol-5-carboxylat (1.00 g, 44% der Theorie). Cesium carbonate (6.26 g, 19.2 mmol, 2.0 equiv) and copper (I) iodide (140 mg, 1.92 mmol, 0.2 equiv). The resulting reaction mixture was stirred at 80 ° C for 3 hours and then cooled to room temperature and added ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The resulting solid was suspended in heptane, stirred and then filtered off. This gives methyl 1-methyl-3- (pyrimidin-2-yloxy) -1H-pyrazole-5-carboxylate (1.00 g, 44% of theory).
'H-NMR (400 MHz, CDCI3 δ, ppm) 8.60 (d, 2H), 7.09 (t, 1H), 6.65 (s, 1H), 4.16 (s, 3H), 3.89 (s, 3H). 'H NMR (400 MHz, CDCl3 δ, ppm) 8.60 (d, 2H), 7.09 (t, 1H), 6.65 (s, 1H), 4.16 (s, 3H), 3.89 (s, 3H).
Synthesestufe 2 : Methyl-4-iod- 1 -methyl-3 -(pyrimidin-2-yloxy)- 1 H-pyrazol-5-carboxylat (Intermediat No. A-09 Synthesis step 2: Methyl 4-iodo-1-methyl-3 - (pyrimidin-2-yloxy) -1-H-pyrazole-5-carboxylate (Intermediate No. A-09
Analog zur Synthese von 2-(4-Iod-l,5-dimethyl-pyrazol-3-yl)oxypyrimidin wurden aus 1.00 g Methyl- l-methyl-3-(pyrimidin-2-yloxy)-lH-pyrazol-5-carboxylat 1.55 g (100%) Methyl-4-iod-l -methyl-3 - (pyrimidin-2-yloxy)- 1 H-pyrazol-5-carboxylat erhalten. H-NMR (400 MHz, CDC13 δ, ppm) 8.60 (d, 2H), 7.11 (t, 1H), 4.20 (s, 3H), 3.95 (s, 3H). Analogously to the synthesis of 2- (4-iodo-1,5-dimethyl-pyrazol-3-yl) oxypyrimidine, from 1.00 g of methyl 1-methyl-3- (pyrimidin-2-yloxy) -1H-pyrazole-5- carboxylate 1.55 g (100%) of methyl 4-iodo-1-methyl-3 - (pyrimidin-2-yloxy) -1 H -pyrazole-5-carboxylate. H-NMR (400 MHz, CDC1 3 δ, ppm) 8.60 (d, 2H), 7.11 (t, 1H), 4.20 (s, 3H), 3.95 (s, 3H).
Synthesestufe 3: Methyl-4-[(4-fluorphenyl)sulfanyl]-l-methyl-3-(pyrimidin-2-yloxy)-lH-pyrazol-5- carbox lat (Synthesebeispiel No. 1-077): Synthesis Step 3: Methyl 4 - [(4-fluorophenyl) sulfanyl] -1-methyl-3- (pyrimidin-2-yloxy) -1H-pyrazole-5-carboxylate (Synthesis Example No. 1-077):
Analog zur Synthese von 2-[4-(2,4-Difluorphenyl)sulfanyl-l,5-dimethyl-pyrazol-3-yl]oxypyrimidin wurden aus 150 mg Methyl-4-iod-l-methyl-3-(pyrimidin-2-yloxy)-lH-pyrazol-5-carboxylat 45 mg (28%) Methyl-4-[(4-fluorphenyl)sulfanyl] - 1 -methyl-3 -(pyrimidin-2-yloxy)- 1 H-pyrazol-5-carboxylat erhalten.  Analogously to the synthesis of 2- [4- (2,4-difluorophenyl) sulfanyl-l, 5-dimethyl-pyrazol-3-yl] oxypyrimidine, 150 mg of methyl 4-iodo-1-methyl-3- (pyrimidine) 2-yloxy) -1H-pyrazole-5-carboxylate 45 mg (28%) of methyl 4 - [(4-fluorophenyl) sulfanyl] -1-methyl-3 - (pyrimidin-2-yloxy) -1 H -pyrazole 5-carboxylate obtained.
'H-NMR (400 MHz, CDCI3 δ, ppm) 8.47 (d, 2H), 7.22-7.19 (m, 2H), 7.02 (t, 1H), 6.86-6.82 (m, 2H), 4.17 (s, 3H), 3.86 (s, 3H).  'H NMR (400 MHz, CDCl3 δ, ppm) 8.47 (d, 2H), 7.22-7.19 (m, 2H), 7.02 (t, 1H), 6.86-6.82 (m, 2H), 4.17 (s, 3H ), 3.86 (s, 3H).
Synthesebeispiel No. 1-005: Synthesis Example No. 1-005:
2- 4-(3,5-Difluorphenyl)-l,5-dimethyl-pyrazol-3-yl]oxypyrimidin 2-4- (3,5-Difluorophenyl) -l, 5-dimethyl-pyrazol-3-yl] oxypyrimidine
Unter Argon wurde 2-(4-Iod-l,5-dimethyl-pyrazol-3-yl)oxypyrimidin (150 mg, 0.48 mmol, 1.0 equiv) in Dioxan (4 ml) gelöst und nacheinander mit 3,5-Difluorphenylboronsäure (165 mg, 1.04 mmol, 2.2 equiv), PdCl2(dppf)(CH2Cl2) (58 mg, 0.071 mmol, 0.15 equiv), Caesiumcarbonat (464 mg, 1.42 mmol, 3.0 equiv) und Wasser (1 ml) versetzt. Das resultierende Reaktionsgemisch wurde bei 130 °C für 1 Stunde in der Mikrowelle gerührt und anschließend auf Raumtemperatur abgekühlt und mit ges.  Under argon, 2- (4-iodo-l, 5-dimethyl-pyrazol-3-yl) oxypyrimidine (150 mg, 0.48 mmol, 1.0 equiv) was dissolved in dioxane (4 ml) and washed successively with 3,5-difluorophenylboronic acid (165 mg, 1.04 mmol, 2.2 equiv), PdCl2 (dppf) (CH2Cl2) (58 mg, 0.071 mmol, 0.15 equiv), cesium carbonate (464 mg, 1.42 mmol, 3.0 equiv) and water (1 ml). The resulting reaction mixture was stirred at 130 ° C for 1 hour in the microwave and then cooled to room temperature and washed with sat.
Natriumhydrogencarbonatlösung versetzt. Die wäßrige Phase wurde mehrfach mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Sodium bicarbonate solution added. The aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final column chromatographic purification (gradient
Essigester/Heptan) des resultierenden Rohproduktes konnte 2-[4-(3,5-Difluorphenyl)-l,5-dimethyl- pyrazol-3-yl]oxypyrimidin in Form eines gelben Feststoffs isoliert werden (111 mg, 74% der Theorie). 'H-NMR (400 MHz, CDC13 δ, ppm) 8.53 (d, 2H), 7.00 (t, 1H), 6.88-6.86 (m, 2H), 6.64-6.60 (i Ethyl acetate / heptane) of the resulting crude product, 2- [4- (3,5-difluorophenyl) -l, 5-dimethyl-pyrazol-3-yl] oxypyrimidine was isolated as a yellow solid (111 mg, 74% of theory). , 'H NMR (400 MHz, CDC1 3 δ, ppm) 8.53 (d, 2H), 7.00 (t, 1H), 6.88-6.86 (m, 2H), 6.64-6.60 (i
3.82 (s, 3H), 2.38 (s, 3H). 3.82 (s, 3H), 2.38 (s, 3H).
Synthesebeispiel No. 1-229: Synthesis Example No. 1-229:
Synthesestufe 1 : 2-(l,5-Dimethyl-4-nitro-pyrazol-3-yl)oxypyrimidin (Intermediat No. A-15) Synthesis step 1: 2- (l, 5-dimethyl-4-nitro-pyrazol-3-yl) oxypyrimidine (Intermediate No. A-15)
2-(l,5-Dimethylpyrazol-3-yl)oxypyrimidin (1.20 g, 6.30 mmol, 1.0 equiv) wurde in Trifluoressigsäure (10 ml) gelöst, mit Trifluoressigsäureanhydrid (6.24 ml, 9.28 mmol, 7.0 equiv) versetzt. Das resultierende Reaktionsgemisch wurde auf eine Temperatur von 0 °C abgekühlt, mit Ammoniumnitrat (530 mg, 6.62 mmol, 1.05 equiv) portionweise versetzt und anschließend für 2.5 Stunden bei Raumtemperatur gerührt. Wasser wurde zugegeben, die wäßrige Phase mehrfach mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte 2-(l,5-Dimethyl-4-nitro-pyrazol-3- yl)oxypyrimidin isoliert werden (980 mg, 66% der Theorie).  2- (l, 5-dimethylpyrazol-3-yl) oxypyrimidine (1.20 g, 6.30 mmol, 1.0 equiv) was dissolved in trifluoroacetic acid (10 ml), added with trifluoroacetic anhydride (6.24 ml, 9.28 mmol, 7.0 equiv). The resulting reaction mixture was cooled to a temperature of 0 ° C, added in portions with ammonium nitrate (530 mg, 6.62 mmol, 1.05 equiv) and then stirred for 2.5 hours at room temperature. Water was added, the aqueous phase extracted several times with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product afforded 2- (l, 5-dimethyl-4-nitro-pyrazol-3-yl) oxypyrimidine (980 mg, 66% of theory).
'H-NMR (400 MHz, CDCI3 δ, ppm) 8.57 (d, 2H), 7.11 (t, 1H), 3.84 (s, 3H), 2.69 (s, 3H).  'H NMR (400 MHz, CDCl3 δ, ppm) 8.57 (d, 2H), 7.11 (t, 1H), 3.84 (s, 3H), 2.69 (s, 3H).
S nthesestufe 2: 1 ,5-Dimethyl-3-pyrimidin-2-yloxy-pyrazol-4-amin Synthesis step 2: 1, 5-dimethyl-3-pyrimidin-2-yloxy-pyrazol-4-amine
2-(l,5-Dimethyl-4-nitro-pyrazol-3-yl)oxypyrimidin (5.00 g, 21.3 mmol, 1.0 equiv) wurde in Ethanol (200 ml) und Wasser (50 ml) gelöst und mit Eisen (3.56 g, 63.8 mmol, 3.0 equiv) und  2- (l, 5-Dimethyl-4-nitro-pyrazol-3-yl) oxypyrimidine (5.00 g, 21.3 mmol, 1.0 equiv) was dissolved in ethanol (200 ml) and water (50 ml) and iron (3.56 g , 63.8 mmol, 3.0 equiv) and
Ammoniumchlorid (1.14 g, 21.3 mmol, 1.0 equiv) versetz. Das resultierende Reaktionsgemisch wurde für 6 Stunden bei 80 °C gerührt und anschließend auf Raumtemperatur abgekühlt, über Kieseiguhr filtriert und eingeengt. Auf diese Weise erhält man l,5-Dimethyl-3-pyrimidin-2-yloxy-pyrazol-4-amin (4.07 g, 93% der Theorie) in Form eines braunen Feststoffs. Ammonium chloride (1.14 g, 21.3 mmol, 1.0 equiv). The resulting reaction mixture was stirred for 6 hours at 80 ° C and then cooled to room temperature, filtered through Kieseiguhr and concentrated. This gives l, 5-dimethyl-3-pyrimidin-2-yloxy-pyrazol-4-amine (4.07 g, 93% of theory) as a brown solid.
'H-NMR (400 MHz, CDCI3 δ, ppm) 8.60 (d, 2H), 7.05 (t, 1H), 3.70 (s, 3H), 2.21 (s, 3H). S nthesestufe 3 : N-(2,4-Difluorphenyl)- 1 ,5-dimethyl-3 -(pyrimidin-2-yloxy)- 1 H-pyrazol-4-amin 'H NMR (400 MHz, CDCl3 δ, ppm) 8.60 (d, 2H), 7.05 (t, 1H), 3.70 (s, 3H), 2.21 (s, 3H). Synthesis step 3: N- (2,4-Difluorophenyl) -1,5-dimethyl-3 - (pyrimidin-2-yloxy) -1 H -pyrazol-4-amine
l,5-Dimethyl-3-pyrimidin-2-yloxy-pyrazol-4-amin (220 mg, 1.07 mmol, 1.0 equiv) und l-Brom-2,4- difluorbenzol (290 mg, 1.50 mmol, 1.4 equiv) wurden in Toluol (6 ml) gelöst und mit 1, 5-Dimethyl-3-pyrimidin-2-yloxy-pyrazol-4-amine (220 mg, 1.07 mmol, 1.0 equiv) and 1-bromo-2,4-difluorobenzene (290 mg, 1.50 mmol, 1.4 equiv) dissolved in toluene (6 ml) and washed with
Tris(dibenzylidenaceton)dipalladium(0) (49 mg, 0.054 mmol, 0.05 equiv), Xantphos (62 mg, 0.11 mmol, 0.1 equiv) und Kalliumphosphat (455 mg, 2.14 mmol, 2.0 equiv) versetzt. Das resultierende Reaktionsgemisch wurde mit Argon entgast und für 2 Stunden bei 120 °C gerührt und anschließend auf Raumtemperatur abgekühlt, mit Dichlormethan verdünnt, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte N-(2,4-Difluorphenyl)-l,5-dimethyl-3-(pyrimidin-2-yloxy)-lH-pyrazol-4-amin isoliert werden (120 mg, 34% der Theorie). Tris (dibenzylideneacetone) dipalladium (0) (49 mg, 0.054 mmol, 0.05 equiv), xanthophos (62 mg, 0.11 mmol, 0.1 equiv) and potassium phosphate (455 mg, 2.14 mmol, 2.0 equiv). The resulting reaction mixture was degassed with argon and stirred for 2 hours at 120 ° C and then cooled to room temperature, diluted with dichloromethane, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product gave N- (2,4-difluorophenyl) -1,5-dimethyl-3- (pyrimidin-2-yloxy) -1H-pyrazol-4-amine ( 120 mg, 34% of theory).
'H-NMR (400 MHz, CDC13 δ, ppm) 8.50 (d, 2H), 7.00 (t, 1H), 6.70-6.61 (m, 2H), 6.57-6.53 (m, 1H), 3.78 (s, 3H), 2.18 (s, 3H). 'H-NMR (400 MHz, CDC1 3 δ, ppm) 8.50 (d, 2H), 7.00 (t, 1H), 6.70-6.61 (m, 2H), 6.57-6.53 (m, 1H), 3.78 (s, 3H), 2.18 (s, 3H).
Synthesestufe 4: N-(2,4-Difluo^henyl)-N,l,5-trimethyl-3-(pyrimidin-2-yloxy)-lH-pyrazol-4-amin (Synthesebeispiel No. 1-229): Synthesis Step 4: N- (2,4-Difluoroethylenyl) -N, l, 5-trimethyl-3- (pyrimidin-2-yloxy) -1H-pyrazole-4-amine (Synthesis Example No. 1-229):
Unter Argon wurde N-(2,4-Difluo^henyl)-l,5-dimethyl-3-(pyrimidin-2-yloxy)-lH-pyrazol-4-amin (60 mg, 0.19 mmol, 1.0 equiv) in wasserfreiem Dimethylformamid (3 ml) gelöst, auf eine Temperatur von 0 °C abgekühlt und mit Natriumhydrid (60% in Öl, 9 mg, 0.23 mmol, 1.2 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei 0 °C für 10 Minuten gerührt und anschließend mit lodmethan (13 μΐ, 0.21 mmol, 1.1 equiv) versetzt. Das resultierende Reaktionsgemisch wurde bei Raumtemperatur für 6 Stunden gerührt und anschließend mit Wasser versetzt. Die wäßrige Phase wurde mehrfach mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über  Under argon, N- (2,4-difluoroethylenyl) -l, 5-dimethyl-3- (pyrimidin-2-yloxy) -1H-pyrazol-4-amine (60 mg, 0.19 mmol, 1.0 equiv) in anhydrous Dimethylformamide (3 ml) was dissolved, cooled to a temperature of 0 ° C and treated with sodium hydride (60% in oil, 9 mg, 0.23 mmol, 1.2 equiv). The resulting reaction mixture was stirred at 0 ° C for 10 minutes and then combined with iodomethane (13 μΐ, 0.21 mmol, 1.1 equiv). The resulting reaction mixture was stirred at room temperature for 6 hours and then treated with water. The aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then over
Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte N-(2,4-Difluorphenyl)- N,l,5-trimethyl-3-(pyrimidin-2-yloxy)-lH-pyrazol-4-amin isoliert werden (42 mg, 67%> der Theorie). 'H-NMR (400 MHz, CDC13 δ, ppm) 8.43 (d, 2H), 6.93 (t, 1H), 6.79-6.75 (m, 1H), 6.65-6.59 (m, 1H), 6.54-6.53 (m, 1H), 3.74 (s, 3H), 3.10 (s, 3H), 2.17 (s, 3H). Dried magnesium sulfate, filtered and concentrated. Final purification by column chromatography (gradient ethyl acetate / heptane) of the resulting crude product isolated N- (2,4-difluorophenyl) -N, 1, 5-trimethyl-3- (pyrimidin-2-yloxy) -1H-pyrazol-4-amine (42 mg, 67%> of theory). 'H NMR (400 MHz, CDC1 3 δ, ppm) 8.43 (d, 2H), 6.93 (t, 1H), 6.79-6.75 (m, 1H), 6.65-6.59 (m, 1H), 6.54-6.53 ( m, 1H), 3.74 (s, 3H), 3.10 (s, 3H), 2.17 (s, 3H).
In Analogie zu den oben angeführten und an entsprechender Stelle rezitierten Herstellungsbeispielen und unter Berücksichtigung der allgemeinen Angaben zur Herstellung von substituierten In analogy to the production examples recited above and recited in the appropriate place and taking into account the general information for the preparation of substituted
(Het-)Arylpyrazolamiden erhält man die nachfolgend genannten und in Tabelle I dargestellten (Het-) Arylpyrazolamiden gives the following and shown in Table I.
Verbindungen der allgemeinen Formel (I) Compounds of the general formula (I)
Tabelle I Table I
Beispiel1 R2 A-Q1 Q2 nummer Example 1 R 2 AQ 1 Q 2 number
1-001 Methyl Methyl Pyridin-4-yl 5-Fluorpyrimidin-2-yl 1-001 methyl methyl pyridin-4-yl 5-fluoropyrimidin-2-yl
1-002 Methyl Methyl Pyridin-4-yl Pyrimidin-2-yl1-002 methyl methyl pyridin-4-yl pyrimidin-2-yl
1-003 Methyl Methyl 3,4-Difluorphenyl 5-Fluorpyrimidin-2-yl1-003 methyl methyl 3,4-difluorophenyl 5-fluoropyrimidin-2-yl
1-004 Methyl Methyl 3- Pyrimidin-2-yl 1-004 methyl methyl 3-pyrimidin-2-yl
(Trifluormethyl)phenyl  (Trifluoromethyl) phenyl
1-005 Methyl Methyl 3,5-Difluorphenyl Pyrimidin-2-yl 1-005 methyl methyl 3,5-difluorophenyl pyrimidin-2-yl
1-006 Methyl Methyl Phenyl Pyrimidin-2-yl1-006 methyl methyl phenyl pyrimidin-2-yl
1-007 Methyl Methyl 3- 5-Fluorpyrimidin-2-yl 1-007 methyl methyl 3-5-fluoropyrimidin-2-yl
(Trifluormethyl)phenyl  (Trifluoromethyl) phenyl
1-008 Methyl Methyl Pyridin-3-yl Pyrimidin-2-yl 1-008 methyl methyl pyridin-3-yl pyrimidin-2-yl
1-009 Methyl Methyl Pyrimidin-5-yl 5-Fluorpyrimidin-2-yl1-009 methyl methyl pyrimidin-5-yl 5-fluoropyrimidin-2-yl
1-010 Methyl Methyl Phenyl 5-Fluorpyrimidin-2-yl1-010 methyl methyl phenyl 5-fluoropyrimidin-2-yl
1-011 Methyl Methyl 3,5-Difluorphenyl 5-Fluorpyrimidin-2-yl1-011 methyl methyl 3,5-difluorophenyl 5-fluoropyrimidin-2-yl
1-012 Methyl Methyl Pyridin-3-yl 5-Fluorpyrimidin-2-yl1-012 methyl methyl pyridin-3-yl 5-fluoropyrimidin-2-yl
1-013 Methyl Methyl 3,4-Difluorphenyl Pyrimidin-2-yl1-013 methyl methyl 3,4-difluorophenyl pyrimidin-2-yl
1-014 Methyl Methyl Pyrimidin-5-yl Pyrimidin-2-yl1-014 methyl methyl pyrimidin-5-yl pyrimidin-2-yl
1-015 Methyl Methoxycarbonyl 4-Fluorphenyl 5-Chlorpyrimidin-2-yl1-015 methyl methoxycarbonyl 4-fluorophenyl 5-chloropyrimidin-2-yl
1-016 Methyl Methyl (4-Fluorphenyl)methyl 5-Fluorpyrimidin-2-yl1-016 methyl methyl (4-fluorophenyl) methyl 5-fluoropyrimidin-2-yl
1-017 Methyl Methyl (4-Fluorphenyl)methyl 5-Methoxypyrimidin-2-yl1-017 methyl methyl (4-fluorophenyl) methyl 5-methoxypyrimidin-2-yl
1-018 Methyl Methyl Benzyl Pyrimidin-2-yl1-018 methyl methyl benzyl pyrimidin-2-yl
1-019 Methyl Methyl (4-Fluorphenyl)methyl Pyrimidin-2-yl1-019 methyl methyl (4-fluorophenyl) methyl pyrimidin-2-yl
1-020 Methyl Methyl Phenoxy Pyrimidin-2-yl1-020 methyl methyl phenoxy pyrimidin-2-yl
1-021 Methyl Ethoxycarbonyl 3,4-Difluorphenoxy Pyrimidin-2-yl1-021 methyl ethoxycarbonyl 3,4-difluorophenoxy pyrimidin-2-yl
1-022 Methyl cyano 4-Fluorphenoxy 5-Chlorpyrimidin-2-yl1-022 methyl cyano 4-fluorophenoxy 5-chloropyrimidin-2-yl
1-023 Methyl Methyl Phenoxy 5-Fluorpyrimidin-2-yl1-023 methyl methyl phenoxy 5-fluoropyrimidin-2-yl
1-024 Methyl Ethoxycarbonyl 3,4-Difluorphenoxy 5-Fluorpyrimidin-2-yl1-024 methyl ethoxycarbonyl 3,4-difluorophenoxy 5-fluoropyrimidin-2-yl
1-025 Methyl Aminocarbonyl 4-Fluorphenoxy 5-Chlorpyrimidin-2-yl Beispiel1 R2 A-Q1 Q2 nummer 1-025 methyl aminocarbonyl 4-fluorophenoxy 5-chloropyrimidin-2-yl Example 1 R 2 AQ 1 Q 2 number
1-026 Methyl Methyl 2,4-Difluorophenoxy Pyrimidin-2-yl 1-026 methyl methyl 2,4-difluorophenoxy pyrimidin-2-yl
1-027 Methyl Methyl 2,4-Difluorophenoxy 2-Chlorpyrimidin-5-yl1-027 methyl methyl 2,4-difluorophenoxy 2-chloropyrimidin-5-yl
1-028 Methyl Methyl 2,4-Difluorophenoxy 5-Fluorpyrimidin-2-yl1-028 methyl methyl 2,4-difluorophenoxy 5-fluoropyrimidin-2-yl
1-029 Methyl Ethoxycarbonyl 3,4-Difluorphenoxy 5-Chlorpyrimidin-2-yl1-029 Methyl ethoxycarbonyl 3,4-Difluorophenoxy 5-chloropyrimidin-2-yl
1-030 Methyl Methyl 2,4-Difluorophenoxy 5-Brompyrimidin-2-yl1-030 methyl methyl 2,4-difluorophenoxy 5-bromopyrimidin-2-yl
1-031 Methyl Methyl 2,4-Difluorophenoxy Pyrazin-2-yl1-031 methyl methyl 2,4-difluorophenoxy pyrazine-2-yl
1-032 Methyl H (4-Fluorphenyl)thio Pyrimidin-2-yl1-032 methyl H (4-fluorophenyl) thio pyrimidin-2-yl
1-033 Methyl H (4-Chlorphenyl)sulfonyl 5-Fluorpyrimidin-2-yl1-033 methyl H (4-chlorophenyl) sulfonyl 5-fluoropyrimidin-2-yl
1-034 Methyl Ethyl (3-Chlorphenyl)thio 5-Fluorpyrimidin-2-yl1-034 methyl ethyl (3-chlorophenyl) thio 5-fluoropyrimidin-2-yl
1-035 Methyl Ethyl (3-Chlorphenyl)thio Pyrimidin-2-yl1-035 methyl ethyl (3-chlorophenyl) thio pyrimidin-2-yl
1-036 Methyl Methyl (3,4-Difluorphenyl)thio Pyrimidin-2-yl1-036 methyl methyl (3,4-difluorophenyl) thio pyrimidin-2-yl
1-037 Methyl Ethyl (3,4-Difluorphenyl)thio 5-Fluorpyrimidin-2-yl1-037 methyl ethyl (3,4-difluorophenyl) thio 5-fluoropyrimidin-2-yl
1-038 Ethyl H (4-Fluorphenyl)thio Pyrimidin-2-yl1-038 ethyl H (4-fluorophenyl) thio pyrimidin-2-yl
1-039 Isopropyl H (4-Fluorphenyl)thio Pyrimidin-2-yl1-039 isopropyl H (4-fluorophenyl) thio pyrimidin-2-yl
1-040 Isopropyl H (4-Chlorophenyl)thio 5-Chlorpyrimidin-2-yl1-040 isopropyl H (4-chlorophenyl) thio 5-chloropyrimidin-2-yl
1-041 Ethyl H (4-Chlorophenyl)thio Pyrimidin-2-yl1-041 ethyl H (4-chlorophenyl) thio pyrimidin-2-yl
1-042 Ethyl H Phenylsulfanyl Pyrimidin-2-yl1-042 ethyl H phenylsulfanyl pyrimidin-2-yl
1-043 Isopropyl H (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl1-043 isopropyl H (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-044 Methyl Methyl (2,4-Difluorphenyl)thio Pyrimidin-2-yl1-044 methyl methyl (2,4-difluorophenyl) thio pyrimidin-2-yl
1-045 Methyl Methyl (3,5- Pyrimidin-2-yl difluorophenyl)thio 1-045 methyl methyl (3,5-pyrimidin-2-yl difluorophenyl) thio
1-046 Methyl Methyl Pyrimidin-2-ylthio Pyrimidin-2-yl 1-046 methyl methyl pyrimidin-2-ylthio pyrimidin-2-yl
1-047 Methyl Methyl (2,4-Difluorphenyl)thio 4,6-Dichlor-l,3,5-triazin- 2-yl 1-047 methyl methyl (2,4-difluorophenyl) thio-4,6-dichloro-l, 3,5-triazin-2-yl
1-048 Methyl Methyl (4-Fluorphenyl)thio 4- 1-048 methyl methyl (4-fluorophenyl) thio 4-
(Methoxycarbonyl)pyridin (Methoxycarbonyl) pyridine
-2-yl  -2-yl
1-049 Methyl Methoxycarbonyl Phenylsulfanyl Pyrimidin-2-yl 1-049 methyl methoxycarbonyl phenylsulfanyl pyrimidin-2-yl
1-050 Methyl Methoxycarbonyl (3,4-Difluorphenyl)thio Pyrimidin-2-yl1-050 methyl methoxycarbonyl (3,4-difluorophenyl) thio pyrimidin-2-yl
1-051 Methyl Methyl Phenylsulfanyl l,3-Thiazol-2-yl1-051 methyl methyl phenylsulfanyl 1, 3-thiazol-2-yl
1-052 Methyl Methyl (5-fluoropyridin-2- Pyrimidin-2-yl yl)thio 1-052 methyl methyl (5-fluoropyridine-2-pyrimidin-2-ylyl) thio
1-053 tert- Methyl Phenylsulfanyl Pyrimidin-2-yl  1-053 tert-methyl phenylsulfanyl pyrimidin-2-yl
Butoxycarbonyl  butoxycarbonyl
1-054 Methyl Methyl [2,4- Pyrimidin-2-yl bis(trifluoromethyl)phe  1-054 methyl methyl [2,4-pyrimidin-2-yl bis (trifluoromethyl) phe
nyl]thio  nyl] thio
1-055 Benzyl Methyl Phenylsulfanyl Pyrimidin-2-yl 1-055 benzyl methyl phenylsulfanyl pyrimidin-2-yl
1-056 2- Methyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl 1-056 2- methyl phenylsulfanyl 5-fluoropyrimidin-2-yl
Methylsulfanyle  Methylsulfanyle
thyl  thyl
1-057 Methyl Methyl (2,4-Difluorphenyl)thio 5-(Trifluormethyl)pyridin- 2-yl  1-057 methyl methyl (2,4-difluorophenyl) thio 5- (trifluoromethyl) pyridin-2-yl
1-058 Methyl Ethyl (4-Chlorophenyl)thio Pyrimidin-2-yl 1-058 methyl ethyl (4-chlorophenyl) thio pyrimidin-2-yl
1-059 Methyl H (4-chlorophenyl)sulfinyl 5-Fluorpyrimidin-2-yl1-059 Methyl H (4-chlorophenyl) sulfinyl 5-fluoropyrimidin-2-yl
1-060 Methyl Methyl (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl Beispiel1 R2 A-Q1 Q2 nummer 1-060 methyl methyl (4-fluorophenyl) thio 5-chloropyrimidin-2-yl Example 1 R 2 AQ 1 Q 2 number
1-061 Methyl Ethyl (3-Chlorphenyl)thio 5-Methoxypyrimidin-2-yl 1-061 methyl ethyl (3-chlorophenyl) thio 5-methoxypyrimidin-2-yl
1-062 Methyl Ethyl (3,4-Difluorphenyl)thio Pyrimidin-2-yl1-062 methyl ethyl (3,4-difluorophenyl) thio pyrimidin-2-yl
1-063 Methyl Ethyl Phenylsulfanyl Pyrimidin-2-yl1-063 methyl ethyl phenylsulfanyl pyrimidin-2-yl
1-064 Methyl Ethyl (4-Fluorphenyl)thio Pyrimidin-2-yl1-064 methyl ethyl (4-fluorophenyl) thio pyrimidin-2-yl
1-065 Methyl Methyl (2-Chlor-4- 5-Fluorpyrimidin-2-yl fluorphenyl)thio 1-065 methyl methyl (2-chloro-4-5-fluoropyrimidin-2-yl fluorophenyl) thio
1-066 Methyl Methyl (4-Chlorophenyl)thio 5-Methoxypyrimidin-2-yl 1-066 methyl methyl (4-chlorophenyl) thio 5-methoxypyrimidin-2-yl
1-067 Methyl H Phenylsulfanyl Pyrimidin-2-yl1-067 methyl H phenylsulfanyl pyrimidin-2-yl
1-068 Methyl Methyl [3- Pyrazin-2-yl 1-068 methyl methyl [3-pyrazine-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
thio  thio
1-069 Methyl Methyl (3-Chlorphenyl)thio Pyrimidin-2-yl 1-069 methyl methyl (3-chlorophenyl) thio pyrimidin-2-yl
1-070 -CH2CH2CH2- (4-Fluorphenyl)thio Pyridin-2-yl1-070 -CH 2 CH 2 CH 2 - (4-fluorophenyl) thio-pyridin-2-yl
1-071 Methyl Methyl (2-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl1-071 methyl methyl (2-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-072 Methyl Methyl [3- 5-Fluorpyrimidin-2-yl 1-072 methyl methyl [3-5-fluoropyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
thio  thio
1-073 Methyl Methyl Pyridin-2-ylthio 5-Fluorpyrimidin-2-yl 1-073 methyl methyl pyridin-2-ylthio 5-fluoropyrimidin-2-yl
1-074 Methyl Methyl (4-Fluorphenyl)thio 4,6-Dichlor-l,3,5-triazin- 2-yl 1-074 methyl methyl (4-fluorophenyl) thio-4,6-dichloro-l, 3,5-triazin-2-yl
1-075 Methyl Phenylmethoxyca Phenylsulfanyl Pyrimidin-2-yl rbonyl  1-075 methyl phenylmethoxy phenylsulfanyl pyrimidin-2-yl rbonyl
1-076 Methyl Methyl Phenylsulfonyl 5-Fluorpyrimidin-2-yl 1-076 methyl methyl phenylsulfonyl 5-fluoropyrimidin-2-yl
1-077 Methyl Methoxycarbonyl (4-Fluorphenyl)thio Pyrimidin-2-yl1-077 methyl methoxycarbonyl (4-fluorophenyl) thio pyrimidin-2-yl
1-078 Methyl Methyl (2,6- 5-Fluorpyrimidin-2-yl difluorophenyl)thio 1-078 methyl methyl (2,6- 5-fluoropyrimidin-2-yl difluorophenyl) thio
1-079 Methyl Methyl Phenylsulfanyl 5- 1-079 methyl methyl phenylsulfanyl 5-
Phenylmethoxycarbonylp yrimidin-2-ylPhenylmethoxycarbonylpyrimidin-2-yl
1-080 Methyl Methyl Phenylsulfanyl 5-1-080 methyl methyl phenylsulfanyl 5-
(Methoxycarbonyl)pyrimi din-2-yl(Methoxycarbonyl) pyrimidine-2-yl
1-081 3-Methoxy-3- Methyl Phenylsulfanyl Pyrimidin-2-yl oxopropyl 1-081 3-Methoxy-3-methylphenylsulfanyl pyrimidin-2-yl oxopropyl
1-082 2-Methoxyethyl Methyl Phenylsulfanyl Pyrimidin-2-yl 1-082 2-methoxyethyl methyl phenylsulfanyl pyrimidin-2-yl
1-083 2-Benzyloxy-2- Methyl Phenylsulfanyl Pyrimidin-2-yl oxoethyl 1-083 2-Benzyloxy-2-methylphenylsulfanyl Pyrimidin-2-yl oxoethyl
1-084 vinyl Methyl Phenylsulfanyl Pyrimidin-2-yl 1-084 vinyl methyl phenylsulfanyl pyrimidin-2-yl
1-085 Methyl cyano (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl1-085 methyl cyano (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-086 Methyl Methyl (4-Fluorphenyl)thio 5-(Trifluormethyl)pyridin- 2-yl 1-086 methyl methyl (4-fluorophenyl) thio 5- (trifluoromethyl) pyridin-2-yl
1-087 Methyl Methyl (4-Fluorphenyl)thio Pyrimidin-2-yl 1-087 methyl methyl (4-fluorophenyl) thio pyrimidin-2-yl
1-088 Methyl Ethyl Phenylsulfanyl 5-Methoxypyrimidin-2-yl1-088 methyl ethyl phenylsulfanyl 5-methoxypyrimidin-2-yl
1-089 Methyl Methyl (4-Fluorphenyl)thio 5-Methoxypyrimidin-2-yl1-089 methyl methyl (4-fluorophenyl) thio 5-methoxypyrimidin-2-yl
1-090 Methyl Methyl (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl1-090 methyl methyl (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-091 Methyl Methyl (3-Chlorphenyl)thio 5-Fluorpyrimidin-2-yl1-091 methyl methyl (3-chlorophenyl) thio 5-fluoropyrimidin-2-yl
1-092 Methyl Methyl (3-fluorophenyl)thio Pyrimidin-2-yl Beispiel1 R2 A-Q1 Q2 nummer 1-092 methyl methyl (3-fluorophenyl) thio pyrimidin-2-yl Example 1 R 2 AQ 1 Q 2 number
1-093 Methyl Methyl (3,4-Difluorphenyl)thio 5-Fluorpyrimidin-2-yl 1-093 methyl methyl (3,4-difluorophenyl) thio 5-fluoropyrimidin-2-yl
1-094 Methyl Ethyl (2,4-Difluorphenyl)thio 5-Fluorpyrimidin-2-yl1-094 methyl ethyl (2,4-difluorophenyl) thio 5-fluoropyrimidin-2-yl
1-095 Methyl H (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl1-095 methyl H (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-096 Methyl Methyl (3-Chlorphenyl)thio 4-Methylpyrimidin-2-yl1-096 methyl methyl (3-chlorophenyl) thio 4-methylpyrimidin-2-yl
1-097 -CH2CH2CH2- (4-Fluorphenyl)thio Pyrimidin-2-yl1-097 -CH 2 CH 2 CH 2 - (4-fluorophenyl) thio-pyrimidin-2-yl
1-098 Methyl Trifluormethyl Phenylsulfanyl Pyrimidin-2-yl1-098 methyl trifluoromethyl phenylsulfanyl pyrimidin-2-yl
1-099 Methyl Methyl (3,5- 5-Fluorpyrimidin-2-yl dichlorophenyl)thio 1-099 methyl methyl (3,5- 5-fluoropyrimidin-2-yl dichlorophenyl) thio
1-100 Methyl Methyl (3,5- 5-Fluorpyrimidin-2-yl difluorophenyl)thio  1-100 methyl methyl (3,5- 5-fluoropyrimidin-2-yl difluorophenyl) thio
1-101 Methyl Methyl (4-Fluorphenyl)thio Pyrazin-2-yl 1-101 methyl methyl (4-fluorophenyl) thio pyrazine-2-yl
1-102 Methyl Methyl (2,4-Difluorphenyl)thio Pyrazin-2-yl1-102 methyl methyl (2,4-difluorophenyl) thio pyrazine-2-yl
1-103 Methyl Methyl (4-Fluorphenyl)thio 5-1-103 methyl methyl (4-fluorophenyl) thio 5-
(Methoxycarbonyl)pyridin (Methoxycarbonyl) pyridine
-2-yl  -2-yl
1-104 Methyl Cyclopropyl (3,4-Difluorphenyl)thio 5-Fluorpyrimidin-2-yl 1-104 methyl cyclopropyl (3,4-difluorophenyl) thio 5-fluoropyrimidin-2-yl
1-105 Methyl Methoxycarbonyl (2,4-Difluorphenyl)thio Pyrimidin-2-yl1-105 methyl methoxycarbonyl (2,4-difluorophenyl) thio pyrimidin-2-yl
1-106 Methyl Methyl pyridin-4-ylthio Pyrimidin-2-yl1-106 methyl methyl pyridin-4-ylthio pyrimidin-2-yl
1-107 Methyl Methyl (2,4,6- 5-Fluorpyrimidin-2-yl trifluorophenyl)thio 1-107 methyl methyl (2,4,6-5-fluoropyrimidin-2-yl trifluorophenyl) thio
1-108 Methyl Methyl pyridin-4-ylthio 5-Fluorpyrimidin-2-yl 1-108 methyl methyl pyridin-4-ylthio 5-fluoropyrimidin-2-yl
1-109 Methyl Cyanomethyl 4-Fluorphenoxy 5-Fluorpyrimidin-2-yl1-109 Methyl cyanomethyl 4-fluorophenoxy 5-fluoropyrimidin-2-yl
1-110 2-Methylpropyl Methyl Phenylsulfanyl Pyrimidin-2-yl1-110 2-methylpropyl methyl phenylsulfanyl pyrimidin-2-yl
1-111 2-Methoxy-2- Methyl Phenylsulfanyl Pyrimidin-2-yl oxoethyl 1-111 2-Methoxy-2-methylphenylsulfanyl pyrimidin-2-yl oxoethyl
1-112 Ethyl Methyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl 1-112 ethyl methyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-113 tert- Methyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl 1-113 tert-methyl phenylsulfanyl 5-fluoropyrimidin-2-yl
Butoxycarbonyl  butoxycarbonyl
1-114 Methyl Methyl (2,4-Difluorphenyl)thio 5- 1-114 methyl methyl (2,4-difluorophenyl) thio 5-
(Trifluormethyl)pyrimidin- 2-yl (Trifluoromethyl) pyrimidin-2-yl
1-115 Methyl Methyl (2,4-Difluorphenyl)thio 5-Fluorpyrimidin-2-yl 1-115 methyl methyl (2,4-difluorophenyl) thio 5-fluoropyrimidin-2-yl
1-116 Methyl Methyl (4-Chlorophenyl)thio Pyrimidin-2-yl1-116 methyl methyl (4-chlorophenyl) thio pyrimidin-2-yl
1-117 Methyl Ethyl (2-chloro-4- Pyrimidin-2-yl fluorophenyl)thio 1-117 methyl ethyl (2-chloro-4-pyrimidin-2-yl fluorophenyl) thio
1-118 Methyl Ethyl (2-chloro-4- 5-Methoxypyrimidin-2-yl fluorophenyl)thio  1-118 methyl ethyl (2-chloro-4-5-methoxypyrimidin-2-yl fluorophenyl) thio
1-119 Isopropyl H (4-Chlorophenyl)thio Pyrimidin-2-yl 1-119 isopropyl H (4-chlorophenyl) thio pyrimidin-2-yl
1-120 Methyl H Phenylsulfanyl 5-Chlorpyrimidin-2-yl1-120 methyl H phenylsulfanyl 5-chloropyrimidin-2-yl
1-121 Ethyl H (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl1-121 ethyl H (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-122 -CH2CH2CH2- (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl1-122 -CH 2 CH 2 CH 2 - (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-123 Methyl Methyl [4- Pyrimidin-2-yl 1-123 methyl methyl [4-pyrimidin-2-yl
(trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
thio  thio
1-124 Methyl Methyl [4- 5-Fluorpyrimidin-2-yl  1-124 methyl methyl [4-5-fluoropyrimidin-2-yl
(trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
thio Beispiel1 R2 A-Q1 Q2 nummer thio Example 1 R 2 AQ 1 Q 2 number
1-125 Methyl phenyl Phenylsulfanyl 5-Brompyrimidin-2-yl 1-125 methyl phenyl phenylsulfanyl 5-bromopyrimidin-2-yl
1-126 Methyl Methyl Phenylsulfanyl Pyrimidin-2-yl1-126 methyl methyl phenylsulfanyl pyrimidin-2-yl
1-127 Methyl Methyl Phenylsulfinyl Pyrimidin-2-yl1-127 methyl methyl phenylsulfinyl pyrimidin-2-yl
1-128 Methyl Methyl Phenylsulfanyl 5-Carboxypyrimidin-2-yl1-128 methyl methyl phenylsulfanyl 5-carboxypyrimidin-2-yl
1-129 Difluormethyl Methyl Phenylsulfanyl Pyrimidin-2-yl1-129 difluoromethyl methyl phenylsulfanyl pyrimidin-2-yl
1-130 Methyl Aminocarbonyl (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl1-130 methyl aminocarbonyl (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-131 Isopropyl Methyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-131 isopropyl methyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-132 Methyl H (4-Chlorophenyl)thio Pyrimidin-2-yl1-132 methyl H (4-chlorophenyl) thio pyrimidin-2-yl
1-133 Methyl Methyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-133 methyl methyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-134 Methyl Methyl (3-Chlorphenyl)thio 5-Methoxypyrimidin-2-yl1-134 methyl methyl (3-chlorophenyl) thio 5-methoxypyrimidin-2-yl
1-135 Methyl Methyl (2-chloro-4- Pyrimidin-2-yl fluorophenyl)thio 1-135 methyl methyl (2-chloro-4-pyrimidin-2-yl fluorophenyl) thio
1-136 Methyl Ethyl (2,4-Difluorphenyl)thio Pyrimidin-2-yl 1-136 methyl ethyl (2,4-difluorophenyl) thio pyrimidin-2-yl
1-137 Isopropyl H (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl1-137 isopropyl H (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-138 Ethyl H Phenylsulfanyl 5-Chlorpyrimidin-2-yl1-138 ethyl H phenylsulfanyl 5-chloropyrimidin-2-yl
1-139 Isopropyl H (4-Chlorophenyl)thio 5-Fluorpyrimidin-2-yl1-139 isopropyl H (4-chlorophenyl) thio 5-fluoropyrimidin-2-yl
1-126 Methyl Methyl Phenylsulfanyl Pyrimidin-2-yl1-126 methyl methyl phenylsulfanyl pyrimidin-2-yl
1-140 Methyl Methyl Phenylsulfanyl 5-Methoxypyrimidin-2-yl1-140 methyl methyl phenylsulfanyl 5-methoxypyrimidin-2-yl
1-141 Methyl Methyl (3,4-Difluorphenyl)thio Pyrazin-2-yl1-141 methyl methyl (3,4-difluorophenyl) thio pyrazine-2-yl
1-093 Methyl Methyl (3,4-Difluorphenyl)thio 5-Fluorpyrimidin-2-yl1-093 methyl methyl (3,4-difluorophenyl) thio 5-fluoropyrimidin-2-yl
1-142 Methyl Methyl [3- Pyrimidin-2-yl 1-142 methyl methyl [3-pyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
thio  thio
1-142 Methyl Methyl [3- Pyrimidin-2-yl  1-142 methyl methyl [3-pyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
thio  thio
1-143 Methyl Methyl (4-methoxyphenyl)thio Pyrimidin-2-yl 1-143 methyl methyl (4-methoxyphenyl) thio pyrimidin-2-yl
1-144 Methyl Methyl Pyrimidin-2-ylthio 5-Fluorpyrimidin-2-yl1-144 methyl methyl pyrimidin-2-ylthio 5-fluoropyrimidin-2-yl
1-145 Methyl Cyclopropyl (3,4-Difluorphenyl)thio Pyrimidin-2-yl1-145 methyl cyclopropyl (3,4-difluorophenyl) thio pyrimidin-2-yl
1-146 Methyl Cyclopropyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-146 methyl cyclopropyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-147 Methyl Propyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-147 methyl propyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-148 Methyl Methyl (4-Cyanphenyl)thio Pyrimidin-2-yl1-148 methyl methyl (4-cyanophenyl) thio pyrimidin-2-yl
1-149 Methyl Methyl Phenylsulfanyl 4,6-Dimethylpyrimidin-2- yi 1-149 methyl methyl phenylsulfanyl 4,6-dimethylpyrimidin-2-yl
1-150 Methyl Methyl (2,6- Pyrimidin-2-yl difluorophenyl)thio  1-150 methyl methyl (2,6-pyrimidin-2-yl difluorophenyl) thio
1-151 2- Methyl Phenylsulfanyl Pyrimidin-2-yl  1-151 2- methyl phenylsulfanyl pyrimidin-2-yl
Methylsulfanyle  Methylsulfanyle
thyl  thyl
1-152 2- Methyl Phenylsulfanyl Pyrimidin-2-yl  1-152 2- methyl phenylsulfanyl pyrimidin-2-yl
(Methanesulfon  (Methanesulfon
amido)ethyl  amido) ethyl
1-153 Methyl Carboxy (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl 1-153 methyl carboxy (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-154 Methyl H (4-Chlorophenyl)thio 5-Fluorpyrimidin-2-yl1-154 methyl H (4-chlorophenyl) thio 5-fluoropyrimidin-2-yl
1-155 Methyl Ethyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl Beispiel1 R2 A-Q1 Q2 nummer 1-155 methyl ethyl phenylsulfanyl 5-fluoropyrimidin-2-yl Example 1 R 2 AQ 1 Q 2 number
1-156 Methyl Methyl (2-chloro-4- 5-Methoxypyrimidin-2-yl fluorophenyl)thio  1-156 methyl methyl (2-chloro-4-5-methoxypyrimidin-2-yl fluorophenyl) thio
1-157 Methyl Methyl (3,4-Difluorphenyl)thio 5-Methoxypyrimidin-2-yl 1-157 methyl methyl (3,4-difluorophenyl) thio 5-methoxypyrimidin-2-yl
1-158 Methyl Methyl (3-fluorophenyl)thio 5-Fluorpyrimidin-2-yl1-158 methyl methyl (3-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-159 Methyl Ethyl (3,4-Difluorphenyl)thio 5-Methoxypyrimidin-2-yl1-159 methyl ethyl (3,4-difluorophenyl) thio 5-methoxypyrimidin-2-yl
1-160 Ethyl H (4-Chlorophenyl)thio 5-Fluorpyrimidin-2-yl1-160 ethyl H (4-chlorophenyl) thio 5-fluoropyrimidin-2-yl
1-161 Methyl Methyl (2,4- Pyrimidin-2-yl difluorophenyl)sulfonyl 1-161 methyl methyl (2,4-pyrimidin-2-yl difluorophenyl) sulfonyl
1-162 Methyl Methyl (3-Chlorphenyl)thio 5- 1-162 methyl methyl (3-chlorophenyl) thio 5-
(Methoxycarbonyl)pyridin (Methoxycarbonyl) pyridine
-2-yl  -2-yl
1-163 -CH2CH2CH2- (2,4-Difluorphenyl)thio Pyrimidin-2-yl 1-163 -CH 2 CH 2 CH 2 - (2,4-difluorophenyl) thio pyrimidin-2-yl
1-164 Methyl Trifluoromethyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-164 methyl trifluoromethyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-165 Methyl Cyclopropyl Phenylsulfanyl Pyrimidin-2-yl1-165 methyl cyclopropyl phenylsulfanyl pyrimidin-2-yl
1-166 Methyl Cyclopropyl (3-Chlorphenyl)thio 5-Fluorpyrimidin-2-yl1-166 methyl cyclopropyl (3-chlorophenyl) thio 5-fluoropyrimidin-2-yl
1-167 Methyl Methyl (3,5- Pyrimidin-2-yl dichlorophenyl)thio 1-167 methyl methyl (3,5-pyrimidin-2-yl dichlorophenyl) thio
1-168 Methyl Methyl (2-Fluorphenyl)thio Pyrimidin-2-yl 1-168 methyl methyl (2-fluorophenyl) thio pyrimidin-2-yl
1-169 Methyl Methyl (4-methoxyphenyl)thio 5-Fluorpyrimidin-2-yl1-169 methyl methyl (4-methoxyphenyl) thio 5-fluoropyrimidin-2-yl
1-170 Methyl Methyl Pyridin-2-ylthio Pyrimidin-2-yl1-170 methyl methyl pyridin-2-ylthio pyrimidin-2-yl
1-171 Methyl Methyl (2,4-Difluorphenyl)thio 3-Fluoropyridin-2-yl1-171 methyl methyl (2,4-difluorophenyl) thio 3-fluoropyridin-2-yl
1-172 Methyl phenyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-172 methyl phenyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-173 Methyl carboxy Phenylsulfanyl Pyrimidin-2-yl1-173 methyl carboxy phenylsulfanyl pyrimidin-2-yl
1-174 Methyl Methyl carbamoyl Phenylsulfanyl Pyrimidin-2-yl1-174 methyl methyl carbamoyl phenylsulfanyl pyrimidin-2-yl
1-175 Methyl Dimethylaminocar Phenylsulfanyl Pyrimidin-2-yl bonyl 1-175 methyl dimethylaminocar phenylsulfanyl pyrimidin-2-yl bonyl
1-176 Methyl Methyl (4-Cyanphenyl)thio 5-Fluorpyrimidin-2-yl 1-176 methyl methyl (4-cyanophenyl) thio 5-fluoropyrimidin-2-yl
1-177 Methyl Methyl (5-Fluorpyridin-2- 5-Fluorpyrimidin-2-yl yl)thio 1-177 methyl methyl (5-fluoropyridine-2-5-fluoropyrimidin-2-ylyl) thio
1-178 phenyl Methyl Phenylsulfanyl Pyrimidin-2-yl 1-178 phenyl methyl phenylsulfanyl pyrimidin-2-yl
1-179 2-Methoxyethyl Methyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-179 2-Methoxyethyl methyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-180 Methyl Methyl (3,4-Difluorphenyl)thio 5-1-180 methyl methyl (3,4-difluorophenyl) thio 5-
(Trifluoromethyl)pyrimidi η-2-yl (Trifluoromethyl) pyrimidi η-2-yl
1-181 Methyl Ethyl (4-Chlorophenyl)thio 5-Fluorpyrimidin-2-yl 1-181 methyl ethyl (4-chlorophenyl) thio 5-fluoropyrimidin-2-yl
1-182 Methyl H (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl1-182 methyl H (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-183 Methyl Ethyl (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl1-183 methyl ethyl (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-184 Methyl Ethyl (3-fluorophenyl)thio Pyrimidin-2-yl1-184 methyl ethyl (3-fluorophenyl) thio pyrimidin-2-yl
1-185 Methyl Ethyl (3-fluorophenyl)thio 5-Methoxypyrimidin-2-yl1-185 methyl ethyl (3-fluorophenyl) thio 5-methoxypyrimidin-2-yl
1-186 Methyl Ethyl (4-Fluorphenyl)thio 5-Methoxypyrimidin-2-yl1-186 methyl ethyl (4-fluorophenyl) thio 5-methoxypyrimidin-2-yl
1-187 Methyl Ethyl (4-Chlorophenyl)thio 5-Methoxypyrimidin-2-yl1-187 methyl ethyl (4-chlorophenyl) thio 5-methoxypyrimidin-2-yl
1-188 Methyl H (4-Chlorophenyl)thio 5-Chlorpyrimidin-2-yl1-188 methyl H (4-chlorophenyl) thio 5-chloropyrimidin-2-yl
1-189 Ethyl H Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-189 ethyl H phenylsulfanyl 5-fluoropyrimidin-2-yl
1-190 Isopropyl H Phenylsulfanyl 5-Chlorpyrimidin-2-yl1-190 isopropyl H phenylsulfanyl 5-chloropyrimidin-2-yl
1-191 Isopropyl H Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-191 isopropyl H phenylsulfanyl 5-fluoropyrimidin-2-yl
1-192 -CH2CH2CH2- (2,4-Difluorphenyl)thio 5-Fluorpyrimidin-2-yl Beispiel1 R2 A-Q1 Q2 nummer 1-192 -CH 2 CH 2 CH 2 - (2,4-difluorophenyl) thio 5-fluoropyrimidin-2-yl Example 1 R 2 AQ 1 Q 2 number
1-193 Methyl Methyl (4-Methylphenyl)thio Pyrimidin-2-yl 1-193 methyl methyl (4-methylphenyl) thio pyrimidin-2-yl
1-194 Methyl Methyl (4-Fluorphenyl)thio 3-Fluorpyridin-2-yl1-194 methyl methyl (4-fluorophenyl) thio 3-fluoropyridin-2-yl
1-195 -CH2CH2CH2- (2,4-Difluorphenyl)thio Pyridin-2-yl1-195 -CH 2 CH 2 CH 2 - (2,4-difluorophenyl) thio-pyridin-2-yl
1-196 Methyl Methyl (2,4,6- Pyrimidin-2-yl 1-196 methyl methyl (2,4,6-pyrimidin-2-yl
Trifluorphenyl)thio  Trifluorophenyl) thio
1-197 Methyl Methyl Phenylsulfanyl 4,6-Dimethoxypyrimidin- 2-yl  1-197 methyl methyl phenylsulfanyl 4,6-dimethoxypyrimidin-2-yl
1-198 Ethyl Methyl Phenylsulfanyl Pyrimidin-2-yl 1-198 ethyl methyl phenylsulfanyl pyrimidin-2-yl
1-199 Isopropyl Methyl Phenylsulfanyl Pyrimidin-2-yl1-199 isopropyl methyl phenylsulfanyl pyrimidin-2-yl
1-200 Methyl Methyl [2- Pyrimidin-2-yl 1-200 methyl methyl [2- pyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
thio  thio
1-201 allyl Methyl Phenylsulfanyl Pyrimidin-2-yl 1-201 allyl methyl phenylsulfanyl pyrimidin-2-yl
1-202 Methyl Methyl Phenylsulfanyl 5-1-202 methyl methyl phenylsulfanyl 5-
(Trifluormethyl)pyrimidin- 2-yl (Trifluoromethyl) pyrimidin-2-yl
1-203 Methyl Ethyl (3-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl 1-203 methyl ethyl (3-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-204 Methyl Methyl (4-Chlorphenyl)thio 5-Fluorpyrimidin-2-yl1-204 methyl methyl (4-chlorophenyl) thio 5-fluoropyrimidin-2-yl
1-205 Methyl Methyl (2,4-Difluorphenyl)thio 5-Methoxypyrimidin-2-yl1-205 methyl methyl (2,4-difluorophenyl) thio 5-methoxypyrimidin-2-yl
1-206 Methyl Methyl (3-Fluorphenyl)thio 5-Methoxypyrimidin-2-yl1-206 methyl methyl (3-fluorophenyl) thio 5-methoxypyrimidin-2-yl
1-207 Methyl Ethyl (2,4-Difluorphenyl)thio 5-Methoxypyrimidin-2-yl1-207 methyl ethyl (2,4-difluorophenyl) thio 5-methoxypyrimidin-2-yl
1-208 Methyl Ethyl (2-Chloro-4- 5-Fluorpyrimidin-2-yl fluorphenyl)thio 1-208 methyl ethyl (2-chloro-4-5-fluoropyrimidin-2-yl fluorophenyl) thio
1-209 Ethyl H (4-Chlorphenyl)thio 5-Chlorpyrimidin-2-yl 1-209 Ethyl H (4-chlorophenyl) thio 5-Chloropyrimidin-2-yl
1-210 Methyl H Phenylsulfanyl 5-Fluorpyrimidin-2-yl1-210 methyl H phenylsulfanyl 5-fluoropyrimidin-2-yl
1-211 Ethyl H (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl1-211 ethyl H (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-212 Methyl Methyl (4-Methylphenyl)thio 5-Fluorpyrimidin-2-yl1-212 methyl methyl (4-methylphenyl) thio 5-fluoropyrimidin-2-yl
1-213 Methyl Methyl (2,4-Difluorphenyl)thio Pyridin-2-yl1-213 methyl methyl (2,4-difluorophenyl) thio-pyridin-2-yl
1-214 Methyl Methyl (4-Fluorphenyl)thio Pyridin-2-yl1-214 methyl methyl (4-fluorophenyl) thio-pyridin-2-yl
1-215 Methyl Methyl (2,4-Difluorphenyl)thio 5-1-215 methyl methyl (2,4-difluorophenyl) thio 5-
(Methoxycarbonyl)pyridin (Methoxycarbonyl) pyridine
-2-yl  -2-yl
1-216 Methyl Methyl (2,4-Difluorphenyl)thio 4- 1-216 methyl methyl (2,4-difluorophenyl) thio 4-
(Methoxycarbonyl)pyridin (Methoxycarbonyl) pyridine
-2-yl  -2-yl
1-217 Methyl Methyl [4- Pyrimidin-2-yl  1-217 methyl methyl [4-pyrimidin-2-yl
(Methoxycarbonyl)phe  (Methoxycarbonyl) phe
nyl]thio  nyl] thio
1-218 Methyl Methyl [4- 5-Fluorpyrimidin-2-yl  1-218 methyl methyl [4-5-fluoropyrimidin-2-yl
(Methoxycarbonyl)phe  (Methoxycarbonyl) phe
nyl]thio  nyl] thio
1-219 Methyl Cyclopropyl (3-Chlorphenyl)thio Pyrimidin-2-yl 1-219 methyl cyclopropyl (3-chlorophenyl) thio pyrimidin-2-yl
1-220 Methyl Phenyl Phenylsulfanyl Pyrimidin-2-yl1-220 methyl phenyl phenylsulfanyl pyrimidin-2-yl
1-221 Methyl Propyl Phenylsulfanyl Pyrimidin-2-yl1-221 methyl propyl phenylsulfanyl pyrimidin-2-yl
1-222 Methyl Methyl Phenylsulfonyl Pyrimidin-2-yl1-222 methyl methyl phenylsulfonyl pyrimidin-2-yl
1-223 Methyl Methyl Phenylsulfinyl 5-Fluorpyrimidin-2-yl1-223 methyl methyl phenylsulfinyl 5-fluoropyrimidin-2-yl
1-224 Methyl Methyl Phenylsulfanyl 5-Methylpyrimidin-2-yl Beispiel1 R2 A-Q1 Q2 nummer 1-224 methyl methyl phenylsulfanyl 5-methylpyrimidin-2-yl Example 1 R 2 AQ 1 Q 2 number
1-225 Carboxymethyl Methyl Phenylsulfanyl Pyrimidin-2-yl 1-225 carboxymethyl methyl phenylsulfanyl pyrimidin-2-yl
1-226 Methyl Methyl (4-Fluorphenyl)thio 5-1-226 methyl methyl (4-fluorophenyl) thio 5-
(Trifluormethyl)pyrimidin- 2-yl (Trifluoromethyl) pyrimidin-2-yl
1-227 H Methyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl 1-227H methyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-228 H Methyl Phenylsulfanyl Pyrimidin-2-yl1-228 H methyl phenylsulfanyl pyrimidin-2-yl
1-228 H Methyl Phenylsulfanyl Pyrimidin-2-yl1-228 H methyl phenylsulfanyl pyrimidin-2-yl
1-229 Methyl Methyl 2,4-Difluor-N- Pyrimidin-2-yl methylanilin 1-229 methyl methyl 2,4-difluoro-N-pyrimidin-2-yl-methylaniline
1-230 Methyl H (4-Chlorphenyl)thio 2-Chlorpyrimidin-5-yl 1-230 methyl H (4-chlorophenyl) thio 2-chloropyrimidin-5-yl
1-231 Methyl H (4-Fluorphenyl)thio 2-Chlorpyrimidin-5-yl1-231 methyl H (4-fluorophenyl) thio 2-chloropyrimidin-5-yl
1-232 Methyl Methyl Phenylsulfanyl Pyridin-3-yl1-232 methyl methyl phenylsulfanyl pyridin-3-yl
1-233 Methyl Methyl Phenylsulfanyl Pyrimidin-5-yl1-233 methyl methyl phenylsulfanyl pyrimidin-5-yl
1-234 Methyl Methyl anilino Pyrimidin-2-yl1-234 methyl methyl anilino pyrimidin-2-yl
1-235 Methyl Methyl 2,4-difluoranilino Pyrimidin-2-yl1-235 methyl methyl 2,4-difluoroanilino pyrimidin-2-yl
1-236 Methyl Methyl 4-Fluoranilino Pyrimidin-2-yl1-236 methyl methyl 4-fluoroanilino pyrimidin-2-yl
1-236 Methyl Methyl 4-Fluoranilino Pyrimidin-2-yl1-236 methyl methyl 4-fluoroanilino pyrimidin-2-yl
1-237 Methyl Methyl 3,4-difluoranilino Pyrimidin-2-yl1-237 methyl methyl 3,4-difluoroanilino pyrimidin-2-yl
1-238 Methyl Methyl 3-Fluoranilino Pyrimidin-2-yl1-238 methyl methyl 3-fluoroanilino pyrimidin-2-yl
1-239 Methyl Methyl 3,5-difluoranilino Pyrimidin-2-yl1-239 methyl methyl 3,5-difluoroanilino pyrimidin-2-yl
1-240 Methyl Methyl 3-Chloranilino Pyrimidin-2-yl1-240 methyl methyl 3-chloroanilino pyrimidin-2-yl
1-241 Methyl Methyl 3- Pyrimidin-2-yl 1-241 methyl methyl 3-pyrimidin-2-yl
(Trifluormethyl)anilino  (Trifluoromethyl) anilino
1-242 Methyl Methyl (3,4-Difluorphenyl)thio 5-(Trifluormethyl)pyridin- 2-yl  1-242 methyl methyl (3,4-difluorophenyl) thio 5- (trifluoromethyl) pyridin-2-yl
1-243 Methyl Methyl Phenylsulfanyl 5-(Trifluormethyl)pyridin- 2-yl  1-243 methyl methyl phenylsulfanyl 5- (trifluoromethyl) pyridin-2-yl
1-244 Methyl Methyl N-methyl-3- Pyrimidin-2-yl  1-244 methyl methyl N -methyl-3-pyrimidin-2-yl
(trifluormethyl)anilino  (Trifluoromethyl) anilino
1-245 Methyl Methyl N-methylanilino Pyrimidin-2-yl 1-245 methyl methyl N-methylanilino pyrimidin-2-yl
1-246 Methyl Methyl 4-Fluor-N- Pyrimidin-2-yl methylanilino 1-246 methyl methyl 4-fluoro-N-pyrimidin-2-yl methylanilino
1-247 Methyl Methyl 3-Chlor-N- Pyrimidin-2-yl methylanilino  1-247 methyl methyl 3-chloro-N-pyrimidin-2-yl methylanilino
1-248 Methyl Methyl pyrimidin-2-ylamino Pyrimidin-2-yl 1-248 methyl methyl pyrimidin-2-ylamino pyrimidin-2-yl
1-249 Methyl Methyl 4-Chloranilino Pyrimidin-2-yl1-249 methyl methyl 4-chloroanilino pyrimidin-2-yl
1-250 Methyl Methyl 3-Fluor-N- Pyrimidin-2-yl methylanilino 1-250 methyl methyl 3-fluoro-N-pyrimidin-2-yl methylanilino
1-251 Methyl Methyl 3,5-difluor-N- Pyrimidin-2-yl methylanilino  1-251 methyl methyl 3,5-difluoro-N-pyrimidin-2-yl methylanilino
1-252 Methyl Methyl methyl(pyrimidin-2- Pyrimidin-2-yl yl)amino  1-252 methyl methyl methyl (pyrimidine-2-pyrimidin-2-yl yl) amino
1-253 Methyl Methyl 4-Chlor-N- Pyrimidin-2-yl methylanilino  1-253 methyl methyl 4-chloro-N-pyrimidin-2-yl-methylanilino
1-254 Methyl Methyl 3,4-difluor-N- Pyrimidin-2-yl methylanilino Beispiel1 R2 A-Q1 Q2 nummer 1-254 methyl methyl 3,4-difluoro-N-pyrimidin-2-yl methylanilino Example 1 R 2 AQ 1 Q 2 number
1-255 Methyl Methyl [5- Pyrimidin-2-yl  1-255 methyl methyl [5-pyrimidin-2-yl
(trifluormethyl)pyridin- 2-yl]amino  (trifluoromethyl) pyridin-2-yl] amino
1-256 Methyl Brom (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl 1-256 methyl bromine (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-257 Methyl Methyl 4-methylanilino Pyrimidin-2-yl1-257 methyl methyl 4-methylanilino pyrimidin-2-yl
1-258 Methyl Chlor (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl1-258 methyl chloro (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-259 Methyl Methyl Phenylsulfanyl 2-Chlorpyrimidin-5-yl1-259 methyl methyl phenylsulfanyl 2-chloropyrimidin-5-yl
1-260 Methyl Methyl methyl-[5- Pyrimidin-2-yl 1-260 methyl methyl methyl- [5-pyrimidin-2-yl
(Trifluormethyl)pyridin- 2-yl]amino  (Trifluoromethyl) pyridin-2-yl] amino
1-261 Methyl Methyl 2,4-difluoranilino 5-Fluorpyrimidin-2-yl 1-261 methyl methyl 2,4-difluoroanilino 5-fluoropyrimidin-2-yl
1-262 Methyl Methyl anilino 5-Fluorpyrimidin-2-yl1-262 methyl methylanilino 5-fluoropyrimidin-2-yl
1-263 Methyl Methyl Phenylsulfanyl Pyridin-4-yl1-263 methyl methyl phenylsulfanyl pyridin-4-yl
1-264 Methyl Diacetylamino (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl1-264 methyl diacetylamino (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-265 Methyl Amino (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl1-265 methyl amino (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-266 Methyl Acetylamino (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl1-266 methyl acetylamino (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-267 Methyl Methyl 3- 5-Fluorpyrimidin-2-yl 1-267 methyl methyl 3-5-fluoropyrimidin-2-yl
(Trifluormethyl)anilino  (Trifluoromethyl) anilino
1-268 Methyl Methyl 3-Fluoranilino 5-Fluorpyrimidin-2-yl 1-268 methyl methyl 3-fluoroanilino 5-fluoropyrimidin-2-yl
1-269 Methyl Methyl 3-Chloranilino 5-Fluorpyrimidin-2-yl1-269 methyl methyl 3-chloroanilino 5-fluoropyrimidin-2-yl
1-270 Methyl Methyl (4-Fluorphenyl)thio 2-Chlorpyrimidin-5-yl1-270 methyl methyl (4-fluorophenyl) thio 2-chloropyrimidin-5-yl
1-271 Methyl Methyl N-methylanilino 5-Fluorpyrimidin-2-yl1-271 methyl methyl N-methylanilino 5-fluoropyrimidin-2-yl
1-272 Methyl Methyl (3,4-Difluorphenyl)thio 2-Chlorpyrimidin-5-yl1-272 methyl methyl (3,4-difluorophenyl) thio 2-chloropyrimidin-5-yl
1-273 Methyl Methyl 3-Fluor-N- 5-Fluorpyrimidin-2-yl methylanilino 1-273 methyl methyl 3-fluoro-N-5-fluoropyrimidin-2-yl methylanilino
1-274 Methyl Methyl pyrazin-2-ylthio 5-Fluorpyrimidin-2-yl 1-274 methyl methyl pyrazine-2-ylthio 5-fluoropyrimidin-2-yl
1-275 Methyl Methyl [2- 5-Fluorpyrimidin-2-yl 1-275 methyl methyl [2-5-fluoropyrimidin-2-yl
(methoxycarbonyl)phe  (Methoxycarbonyl) phe
nyl]thio  nyl] thio
1-276 Methyl Methyl 3,5-difluoranilino 5-Fluorpyrimidin-2-yl 1-276 methyl methyl 3,5-difluoroanilino 5-fluoropyrimidin-2-yl
1-277 Methyl Methyl (4-nitrophenyl)thio 5-Fluorpyrimidin-2-yl1-277 methyl methyl (4-nitrophenyl) thio 5-fluoropyrimidin-2-yl
1-278 Methyl Methyl (3-methoxyphenyl)thio 5-Fluorpyrimidin-2-yl1-278 methyl methyl (3-methoxyphenyl) thio 5-fluoropyrimidin-2-yl
1-279 Methyl Methyl (2-methylphenyl)thio 5-Fluorpyrimidin-2-yl1-279 methyl methyl (2-methylphenyl) thio 5-fluoropyrimidin-2-yl
1-280 Methyl Methyl (4- Pyrimidin-2-yl methylphenyl)methyl 1-280 methyl methyl (4-pyrimidin-2-ylmethylphenyl) methyl
1-281 Methyl Methyl (2,4- Pyrimidin-2-yl difluorphenyl)methyl  1-281 methyl methyl (2,4-pyrimidin-2-yl difluorophenyl) methyl
1-282 Methyl Methyl (2,5- Pyrimidin-2-yl difluorphenyl)methyl  1-282 methyl methyl (2,5-pyrimidin-2-yl difluorophenyl) methyl
1-283 Methyl Methyl (3,4- Pyrimidin-2-yl  1-283 methyl methyl (3,4-pyrimidin-2-yl
Difluorphenyl)methyl  Difluorophenyl) methyl
1-284 Methyl Methyl (2-Chlorpyridin-4- Pyrimidin-2-yl yl)methyl  1-284 methyl methyl (2-chloropyridine-4-pyrimidin-2-yl yl) methyl
1-285 Methyl Methyl [3- Pyrimidin-2-yl  1-285 methyl methyl [3-pyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
methyl Beispiel1 R2 A-Q1 Q2 nummer methyl Example 1 R 2 AQ 1 Q 2 number
1-286 Methyl Methyl (3,5- Pyrimidin-2-yl difluorphenyl)methyl  1-286 methyl methyl (3,5-pyrimidin-2-yl difluorophenyl) methyl
1-287 Methyl Methyl (3,4- 5-Fluorpyrimidin-2-yl  1-287 methyl methyl (3,4-5-fluoropyrimidin-2-yl
Difluorphenyl)methyl  Difluorophenyl) methyl
1-288 Methyl Methyl (3,5- 5-Fluorpyrimidin-2-yl difluorphenyl)methyl  1-288 methyl methyl (3,5- 5-fluoropyrimidin-2-yl difluorophenyl) methyl
1-289 Methyl Methyl (2,5- 5-Fluorpyrimidin-2-yl difluorphenyl)methyl  1-289 methyl methyl (2,5- 5-fluoropyrimidin-2-yl difluorophenyl) methyl
1-290 Methyl Methyl (2,4- 5-Fluorpyrimidin-2-yl difluorphenyl)methyl  1-290 methyl methyl (2,4,5-fluoropyrimidin-2-yl difluorophenyl) methyl
1-291 Methyl Methyl [3- 5-Fluorpyrimidin-2-yl  1-291 methyl methyl [3-5-fluoropyrimidin-2-yl
(trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
methyl  methyl
1-291 Methyl Methyl [3- 5-Fluorpyrimidin-2-yl  1-291 methyl methyl [3-5-fluoropyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
methyl  methyl
1-292 Methyl Methyl (3-methoxyphenyl)thio Pyrimidin-2-yl 1-292 methyl methyl (3-methoxyphenyl) thio pyrimidin-2-yl
1-293 Methyl Methyl (4-Chlorphenyl)methyl 5-Fluorpyrimidin-2-yl1-293 methyl methyl (4-chlorophenyl) methyl 5-fluoropyrimidin-2-yl
1-293 Methyl Methyl (4-Chlorphenyl)methyl 5-Fluorpyrimidin-2-yl1-293 methyl methyl (4-chlorophenyl) methyl 5-fluoropyrimidin-2-yl
1-294 Methyl Methyl (2-methylphenyl)thio Pyrimidin-2-yl1-294 methyl methyl (2-methylphenyl) thio pyrimidin-2-yl
1-295 Methyl Methyl (2-carboxyphenyl)thio 5-Fluorpyrimidin-2-yl1-295 methyl methyl (2-carboxyphenyl) thio 5-fluoropyrimidin-2-yl
1-296 Methyl Methyl 4-Fluoranilino 5-Fluorpyrimidin-2-yl1-296 methyl methyl 4-fluoroanilino 5-fluoropyrimidin-2-yl
1-297 Methyl Methyl 3,5-difluor-N- 5-Fluorpyrimidin-2-yl methylanilino 1-297 methyl methyl 3,5-difluoro-N-5-fluoropyrimidin-2-yl methylanilino
1-298 Methyl Methyl [3- Pyrimidin-2-yl  1-298 methyl methyl [3-pyrimidin-2-yl
(methoxycarbonyl)phe  (Methoxycarbonyl) phe
nyl]thio  nyl] thio
1-299 Methyl Methyl [3- 5-Fluorpyrimidin-2-yl  1-299 methyl methyl [3-5-fluoropyrimidin-2-yl
(methoxycarbonyl)phe  (Methoxycarbonyl) phe
nyl]thio  nyl] thio
1-300 Methyl Methyl [2- Pyrimidin-2-yl  1-300 methyl methyl [2- pyrimidin-2-yl
(methoxycarbonyl)phe  (Methoxycarbonyl) phe
nyl]thio  nyl] thio
1-301 Methyl Methyl (3-carboxyphenyl)thio 5-Fluorpyrimidin-2-yl 1-301 methyl methyl (3-carboxyphenyl) thio 5-fluoropyrimidin-2-yl
1-302 Methyl Methyl (3-carboxyphenyl)thio Pyrimidin-2-yl1-302 methyl methyl (3-carboxyphenyl) thio pyrimidin-2-yl
1-303 Methyl Methyl (2-carboxyphenyl)thio Pyrimidin-2-yl1-303 methyl methyl (2-carboxyphenyl) thio pyrimidin-2-yl
1-304 Methyl Methyl Pyrimidin-2-yloxy Pyrimidin-2-yl1-304 methyl methyl pyrimidin-2-yloxy pyrimidin-2-yl
1-305 Methyl Methyl 4-Chloranilino 5-Fluorpyrimidin-2-yl1-305 methyl methyl 4-chloroanilino 5-fluoropyrimidin-2-yl
1-306 Methyl Methyl 3,4-difluoranilino 5-Fluorpyrimidin-2-yl1-306 methyl methyl 3,4-difluoroanilino 5-fluoropyrimidin-2-yl
1-307 Methyl Methyl 4-methylanilino 5-Fluorpyrimidin-2-yl1-307 methyl methyl 4-methylanilino 5-fluoropyrimidin-2-yl
1-308 Methyl Methyl N-methyl-3- 5-Fluorpyrimidin-2-yl 1-308 methyl methyl N -methyl-3-5-fluoropyrimidin-2-yl
(trifluormethyl)anilino  (Trifluoromethyl) anilino
1-309 Methyl Methyl [5- 5-Fluorpyrimidin-2-yl  1-309 methyl methyl [5-5-fluoropyrimidin-2-yl
(Trifluormethyl)pyridin- 2-yl]amino  (Trifluoromethyl) pyridin-2-yl] amino
1-310 Methyl Methyl pyrimidin-2-ylamino 5-Fluorpyrimidin-2-yl 1-310 methyl methyl pyrimidin-2-ylamino 5-fluoropyrimidin-2-yl
1-311 Methyl Methyl (5-cyanopyrimidin-2- 5-Fluorpyrimidin-2-yl yl)oxy Beispiel1 R2 A-Q1 Q2 nummer 1-311 methyl methyl (5-cyanopyrimidine-2-5-fluoropyrimidin-2-yl yl) oxy Example 1 R 2 AQ 1 Q 2 number
1-312 Methyl Methyl (5-Chlorpyrimidin-2- 5-Fluorpyrimidin-2-yl yl)oxy  1-312 methyl methyl (5-chloropyrimidine-2-5-fluoropyrimidin-2-ylyl) oxy
1-313 Methyl Methyl (5-Fluorpyrimidin-2- 5-Fluorpyrimidin-2-yl yl)oxy  1-313 methyl methyl (5-fluoropyrimidine-2-5-fluoropyrimidin-2-ylyl) oxy
1-314 Methyl Methyl Pyrimidin-2-yloxy 5-Fluorpyrimidin-2-yl 1-314 methyl methyl pyrimidin-2-yloxy 5-fluoropyrimidin-2-yl
1-315 Methyl Methyl [5- Pyrimidin-2-yl 1-315 methyl methyl [5-pyrimidin-2-yl
(Trifluormethyl)pyridin- 2-yl]oxy  (Trifluoromethyl) pyridin-2-yl] oxy
1-316 Methyl Methyl (5-Fluorpyrimidin-2- Pyrimidin-2-yl yl)oxy  1-316 methyl methyl (5-fluoropyrimidine-2-pyrimidin-2-yl-yl) oxy
1-317 Methyl Methyl 3,4-difluor-N- 5-Fluorpyrimidin-2-yl methylanilino  1-317 methyl methyl 3,4-difluoro-N-5-fluoropyrimidin-2-yl methylanilino
1-318 Methyl Methyl 4-Chlor-N- 5-Fluorpyrimidin-2-yl methylanilino  1-318 methyl methyl 4-chloro-N-5-fluoropyrimidin-2-yl methylanilino
1-319 Methyl Methyl (5-cyanopyrimidin-2- Pyrimidin-2-yl yl)oxy  1-319 methyl methyl (5-cyanopyrimidine-2-pyrimidin-2-ylyl) oxy
1-320 Methyl Methyl (5-methylpyrimidin-2- 5-Fluorpyrimidin-2-yl yl)oxy  1-320 methyl methyl (5-methylpyrimidine-2-5-fluoropyrimidin-2-ylyl) oxy
1-321 Methyl Methyl pyrazin-2-yloxy 5-Fluorpyrimidin-2-yl 1-321 methyl methyl pyrazine-2-yloxy 5-fluoropyrimidin-2-yl
1-322 Methyl Methyl [5- 5-Fluorpyrimidin-2-yl 1-322 methyl methyl [5-5-fluoropyrimidin-2-yl
(Trifluormethyl)pyridin- 2-yl]oxy  (Trifluoromethyl) pyridin-2-yl] oxy
1-323 Methyl Methyl cyclopentylthio Pyrimidin-2-yl 1-323 methyl methyl cyclopentylthio pyrimidin-2-yl
1-323 Methyl Methyl cyclopentylthio Pyrimidin-2-yl1-323 methyl methyl cyclopentylthio pyrimidin-2-yl
1-324 Methyl Methyl cyclopentylthio 5-Fluorpyrimidin-2-yl1-324 methyl methyl cyclopentylthio 5-fluoropyrimidin-2-yl
1-325 Methyl Methyl (2,4,6- Pyrimidin-2-yl 1-325 methyl methyl (2,4,6-pyrimidin-2-yl
Trimethylphenyl)thio  Trimethylphenyl) thio
1-326 Methyl Methyl (2,6- Pyrimidin-2-yl dimethylphenyl)thio  1-326 methyl methyl (2,6-pyrimidin-2-yl dimethylphenyl) thio
1-327 Methyl Methyl (2-methoxyphenyl)thio Pyrimidin-2-yl 1-327 methyl methyl (2-methoxyphenyl) thio pyrimidin-2-yl
1-328 Methyl Methyl cyclohexylthio 5-Fluorpyrimidin-2-yl1-328 methyl methylcyclohexylthio 5-fluoropyrimidin-2-yl
1-329 Methyl Methyl cyclohexylthio Pyrimidin-2-yl1-329 methyl methylcyclohexylthio pyrimidin-2-yl
1-330 Methyl Methyl (4-nitrophenyl)thio Pyrimidin-2-yl1-330 methyl methyl (4-nitrophenyl) thio pyrimidin-2-yl
1-331 Methyl Methyl (2-methoxyphenyl)thio 5-Fluorpyrimidin-2-yl1-331 methyl methyl (2-methoxyphenyl) thio 5-fluoropyrimidin-2-yl
1-332 Methyl Methyl (2,4,6- 5-Fluorpyrimidin-2-yl 1-332 methyl methyl (2,4,6-5-fluoropyrimidin-2-yl
Trimethylphenyl)thio  Trimethylphenyl) thio
1-333 Methyl Methoxycarbonyl (3,4- Pyrimidin-2-yl  1-333 methyl methoxycarbonyl (3,4-pyrimidin-2-yl
Difluorphenyl)methyl  Difluorophenyl) methyl
1-333 Methyl Methoxycarbonyl (3,4- Pyrimidin-2-yl  1-333 methyl methoxycarbonyl (3,4-pyrimidin-2-yl
Difluorphenyl)methyl  Difluorophenyl) methyl
1-334 Methyl Methoxycarbonyl (3,5-difluorphenyl)thio Pyrimidin-2-yl 1-334 methyl methoxycarbonyl (3,5-difluorophenyl) thio pyrimidin-2-yl
1-335 H Methyl 3-(Trifluormethyl) Pyrimidin-2-yl phenoxy 1-335 H methyl 3- (trifluoromethyl) pyrimidin-2-yl phenoxy
1-336 Methyl Methoxycarbonyl (5-Fluorpyridin-2- 5-Fluorpyrimidin-2-yl yl)thio  1-336 methyl methoxycarbonyl (5-fluoropyridine-2-5-fluoropyrimidin-2-ylyl) thio
1-337 H Ethoxycarbonyl (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl Beispiel1 R2 A-Q1 Q2 nummer 1-337 H Ethoxycarbonyl (4-fluorophenyl) thio 5-Chloropyrimidin-2-yl Example 1 R 2 AQ 1 Q 2 number
1-338 Methyl Methoxycarbonyl (3,4- 5-Fluorpyrimidin-2-yl  1-338 methyl methoxycarbonyl (3,4-5-fluoropyrimidin-2-yl
Difluorphenyl)methyl  Difluorophenyl) methyl
1-339 Methyl Methoxycarbonyl benzyl Pyrimidin-2-yl 1-339 methyl methoxycarbonyl benzyl pyrimidin-2-yl
1-340 Methyl Methoxycarbonyl benzyl 5-Fluorpyrimidin-2-yl1-340 methyl methoxycarbonylbenzyl 5-fluoropyrimidin-2-yl
1-341 Methyl Methoxycarbonyl (3,5-difluorphenyl)thio 5-Fluorpyrimidin-2-yl1-341 methyl methoxycarbonyl (3,5-difluorophenyl) thio 5-fluoropyrimidin-2-yl
1-342 Methyl Methoxycarbonyl (4-cyanophenyl)thio 5-Fluorpyrimidin-2-yl1-342 methyl methoxycarbonyl (4-cyanophenyl) thio 5-fluoropyrimidin-2-yl
1-343 Methyl Methoxycarbonyl (4-cyanophenyl)thio Pyrimidin-2-yl1-343 Methyl Methoxycarbonyl (4-cyanophenyl) thio Pyrimidin-2-yl
1-343 Methyl Methoxycarbonyl (4-cyanophenyl)thio Pyrimidin-2-yl1-343 Methyl Methoxycarbonyl (4-cyanophenyl) thio Pyrimidin-2-yl
1-344 Methyl Methoxycarbonyl [3- 5-Fluorpyrimidin-2-yl 1-344 methyl methoxycarbonyl [3-5-fluoropyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
thio  thio
1-345 Methyl Methoxycarbonyl [3- Pyrimidin-2-yl  1-345 methyl methoxycarbonyl [3-pyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
thio  thio
1-346 Methyl Methoxycarbonyl pyridin-2-ylthio 5-Fluorpyrimidin-2-yl 1-346 methyl methoxycarbonyl-pyridin-2-ylthio-5-fluoropyrimidin-2-yl
1-347 Methyl Methoxycarbonyl pyridin-2-ylthio Pyrimidin-2-yl1-347 methyl methoxycarbonyl-pyridin-2-ylthio pyrimidin-2-yl
1-348 Methyl Methoxycarbonyl [3- 5-Fluorpyrimidin-2-yl 1-348 methyl methoxycarbonyl [3-5-fluoropyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
methyl  methyl
1-349 Methyl Methoxycarbonyl [3- Pyrimidin-2-yl  1-349 methyl methoxycarbonyl [3-pyrimidin-2-yl
(Trifluormethyl)phenyl]  (Trifluoromethyl) phenyl]
methyl  methyl
1-350 Methyl Methoxycarbonyl (2,4- 5-Fluorpyrimidin-2-yl difluorphenyl)methyl  1-350 methyl methoxycarbonyl (2,4-5-fluoropyrimidin-2-yl difluorophenyl) methyl
1-351 Methyl Methoxycarbonyl (2,4- Pyrimidin-2-yl difluorphenyl)methyl  1-351 methyl methoxycarbonyl (2,4-pyrimidin-2-yl difluorophenyl) methyl
1-352 Methyl Methoxycarbonyl Phenylsulfanyl 5-Fluorpyrimidin-2-yl 1-352 methyl methoxycarbonyl phenylsulfanyl 5-fluoropyrimidin-2-yl
1-353 Methyl Methoxycarbonyl (4-Fluorphenyl)methyl 5-Fluorpyrimidin-2-yl1-353 Methyl Methoxycarbonyl (4-fluorophenyl) methyl 5-fluoropyrimidin-2-yl
1-354 Methyl Methoxycarbonyl (4-Fluorphenyl)methyl Pyrimidin-2-yl1-354 methyl methoxycarbonyl (4-fluorophenyl) methyl pyrimidin-2-yl
1-354 Methyl Methoxycarbonyl (4-Fluorphenyl)methyl Pyrimidin-2-yl1-354 methyl methoxycarbonyl (4-fluorophenyl) methyl pyrimidin-2-yl
1-355 Methyl Methoxycarbonyl (2-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl1-355 methyl methoxycarbonyl (2-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-356 Methyl Methoxycarbonyl (2-Fluorphenyl)thio Pyrimidin-2-yl1-356 methyl methoxycarbonyl (2-fluorophenyl) thio pyrimidin-2-yl
1-357 Methyl Methoxycarbonyl (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl1-357 methyl methoxycarbonyl (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-358 Methyl Methoxycarbonyl (3,4-Difluorphenyl)thio 5-Fluorpyrimidin-2-yl1-358 methyl methoxycarbonyl (3,4-difluorophenyl) thio 5-fluoropyrimidin-2-yl
1-359 Methyl Methoxycarbonyl (3-Chlorphenyl)thio Pyrimidin-2-yl1-359 methyl methoxycarbonyl (3-chlorophenyl) thio pyrimidin-2-yl
1-360 Methyl Methoxycarbonyl (3-Chlorphenyl)thio 5-Fluorpyrimidin-2-yl1-360 methyl methoxycarbonyl (3-chlorophenyl) thio 5-fluoropyrimidin-2-yl
1-361 Methyl Methoxycarbonyl (4-methylphenyl)thio Pyrimidin-2-yl1-361 methyl methoxycarbonyl (4-methylphenyl) thio pyrimidin-2-yl
1-362 Methyl Methoxycarbonyl (4-methylphenyl)thio 5-Fluorpyrimidin-2-yl1-362 methyl methoxycarbonyl (4-methylphenyl) thio 5-fluoropyrimidin-2-yl
1-363 Methyl Methoxycarbonyl (2,4,6- Pyrimidin-2-yl 1-363 methyl methoxycarbonyl (2,4,6-pyrimidin-2-yl
Trifluorphenyl)thio  Trifluorophenyl) thio
1-364 Methyl Methoxycarbonyl (2,4,6- 5-Fluorpyrimidin-2-yl  1-364 methyl methoxycarbonyl (2,4,6-5-fluoropyrimidin-2-yl
Trifluorphenyl)thio  Trifluorophenyl) thio
1-365 Methyl Methyl 3-Chlor-N- 5-Fluorpyrimidin-2-yl methylanilino  1-365 methyl methyl 3-chloro-N-5-fluoropyrimidin-2-yl methylanilino
1-366 Methyl Methyl (2,6- 5-Fluorpyrimidin-2-yl dimethylphenyl)thio Beispiel1 R2 A-Q1 Q2 nummer 1-366 methyl methyl (2,6- 5-fluoropyrimidin-2-yl dimethylphenyl) thio Example 1 R 2 AQ 1 Q 2 number
1-367 Methyl Methoxycarbonyl (5-Fluorpyridin-2- Pyrimidin-2-yl yl)thio  1-367 Methyl Methoxycarbonyl (5-fluoropyridine-2-pyrimidin-2-ylyl) thio
1-368 Methyl Methyl 2,4-Difluorphenoxy 5-Chlorpyrimidin-2-yl 1-368 methyl methyl 2,4-difluorophenoxy 5-chloropyrimidin-2-yl
1-369 Methyl Methyl 2,4-Difluorphenoxy 5-(Trifluormethyl)pyridin- 2-yl 1-369 methyl methyl 2,4-difluorophenoxy 5- (trifluoromethyl) pyridin-2-yl
1-370 H Ethoxycarbonyl Phenylsulfanyl Pyrimidin-2-yl 1-370H ethoxycarbonyl phenylsulfanyl pyrimidin-2-yl
1-371 H Ethoxycarbonyl (3,4-Difluorphenyl)thio Pyrimidin-2-yl1-371 H ethoxycarbonyl (3,4-difluorophenyl) thio pyrimidin-2-yl
1-372 Methyl Methyl 3- Pyrimidin-2-yl 1-372 methyl methyl 3-pyrimidin-2-yl
(Trifluormethyl)phenox  (Trifluoromethyl) phenox
y  y
1-373 Methyl Methyl 4-Fluorphenoxy 5-Fluorpyrimidin-2-yl 1-373 methyl methyl 4-fluorophenoxy 5-fluoropyrimidin-2-yl
1-374 Methyl Methyl 4-Fluorphenoxy 5-(Trifluormethyl)pyridin- 2-yl 1-374 methyl methyl 4-fluorophenoxy 5- (trifluoromethyl) pyridin-2-yl
1-375 Methyl Methyl 4-Fluorphenoxy Pyrimidin-2-yl 1-375 methyl methyl 4-fluorophenoxy pyrimidin-2-yl
1-376 Methyl Methyl 4-Fluorphenoxy 5-Chlorpyrimidin-2-yl1-376 methyl methyl 4-fluorophenoxy 5-chloropyrimidin-2-yl
1-377 Methyl Methyl 3,4-difluorphenoxy 5-Fluorpyrimidin-2-yl1-377 methyl methyl 3,4-difluorophenoxy 5-fluoropyrimidin-2-yl
1-378 Methyl Methyl 3,4-difluorphenoxy Pyrimidin-2-yl1-378 methyl methyl 3,4-difluorophenoxy pyrimidin-2-yl
1-379 Methyl Methyl 3-methoxyphenoxy Pyrimidin-2-yl1-379 methyl methyl 3-methoxyphenoxy pyrimidin-2-yl
1-380 Methyl Methyl 3-methoxyphenoxy 5-Fluorpyrimidin-2-yl1-380 methyl methyl 3-methoxyphenoxy 5-fluoropyrimidin-2-yl
1-381 H Ethoxycarbonyl (4-cyanophenyl)thio Pyrimidin-2-yl1-381 H ethoxycarbonyl (4-cyanophenyl) thio pyrimidin-2-yl
1-382 Methyl Methyl 3,4-difluorphenoxy 5-Chlorpyrimidin-2-yl1-382 methyl methyl 3,4-difluorophenoxy 5-chloropyrimidin-2-yl
1-383 Methyl Methyl 3-methoxyphenoxy 5-(Trifluormethyl)pyridin- 2-yl 1-383 methyl methyl 3-methoxyphenoxy 5- (trifluoromethyl) pyridin-2-yl
1-384 Methyl Methyl 4-methylphenoxy Pyrimidin-2-yl 1-384 methyl methyl 4-methylphenoxy pyrimidin-2-yl
1-385 Methyl Methyl 4-methylphenoxy 5-Fluorpyrimidin-2-yl1-385 methyl methyl 4-methylphenoxy 5-fluoropyrimidin-2-yl
1-386 Methyl Methyl 3,4-difluorphenoxy 5-(Trifluormethyl)pyridin- 2-yl 1-386 methyl methyl 3,4-difluorophenoxy 5- (trifluoromethyl) pyridin-2-yl
1-387 Methyl Methyl 3-(Trifluormethyl) 5-Chlorpyrimidin-2-yl phenoxy  1-387 methyl methyl 3- (trifluoromethyl) 5-chloropyrimidin-2-yl phenoxy
1-388 Methyl Methyl 3-(Trifluormethyl) 5-Fluorpyrimidin-2-yl phenoxy  1-388 methyl methyl 3- (trifluoromethyl) 5-fluoropyrimidin-2-yl phenoxy
1-389 Methyl Methyl 4-cyanophenoxy Pyrimidin-2-yl 1-389 methyl methyl 4-cyanophenoxy pyrimidin-2-yl
1-390 Methyl Methyl 3-(Trifluormethyl) 5-(Trifluormethyl)pyridin- phenoxy 2-yl 1-390 methyl methyl 3- (trifluoromethyl) 5- (trifluoromethyl) pyridinophenoxy-2-yl
1-391 Allyl Methyl 4-Cyanophenoxy Pyrimidin-2-yl 1-391 allyl methyl 4-cyanophenoxy pyrimidin-2-yl
1-392 Methyl Methyl [3-(Trifluormethoxy) Pyrimidin-2-yl phenyl]thio 1-392 methyl methyl [3- (trifluoromethoxy) pyrimidin-2-yl phenyl] thio
1-393 Methyl Methyl (3- Pyrimidin-2-yl methylsulfanylphenyl)  1-393 methyl methyl (3-pyrimidin-2-yl methylsulfanylphenyl)
thio  thio
1-394 Methyl Methyl (3-ethoxyphenyl)thio Pyrimidin-2-yl 1-394 methyl methyl (3-ethoxyphenyl) thio pyrimidin-2-yl
1-395 Methyl Methyl (3-methylphenyl)thio Pyrimidin-2-yl1-395 methyl methyl (3-methylphenyl) thio pyrimidin-2-yl
1-396 Methyl Methyl (3-methylphenyl)thio 5-Fluorpyrimidin-2-yl1-396 methyl methyl (3-methylphenyl) thio 5-fluoropyrimidin-2-yl
1-397 Methyl Methyl [3-(Trifluormethoxy) 5-Fluorpyrimidin-2-yl phenyl]thio Beispiel1 R2 A-Q1 Q2 nummer 1-397 methyl methyl [3- (trifluoromethoxy) 5-fluoropyrimidin-2-yl phenyl] thio Example 1 R 2 AQ 1 Q 2 number
1-398 Methyl Methoxycarbonyl (3- Pyrimidin-2-yl methylsulfanylphenyl)  1-398 methyl methoxycarbonyl (3-pyrimidin-2-yl methylsulfanylphenyl)
thio  thio
1-399 Methyl Methoxycarbonyl (3-ethoxyphenyl)thio Pyrimidin-2-yl 1-399 methyl methoxycarbonyl (3-ethoxyphenyl) thio pyrimidin-2-yl
1-400 Methyl Methoxycarbonyl [3-(Trifluormethoxy) Pyrimidin-2-yl phenyl]thio 1-400 methyl methoxycarbonyl [3- (trifluoromethoxy) pyrimidin-2-yl phenyl] thio
1-401 Methyl Methyl (3,5- Pyrimidin-2-yl dimethylphenyl)thio  1-401 methyl methyl (3,5-pyrimidin-2-yl dimethylphenyl) thio
1-402 Methyl Methoxycarbonyl (3-methylphenyl)thio Pyrimidin-2-yl 1-402 methyl methoxycarbonyl (3-methylphenyl) thio pyrimidin-2-yl
1-403 Methyl Methoxycarbonyl [3-(Trifluormethoxy) 5-Fluorpyrimidin-2-yl phenyl]thio 1-403 methyl methoxycarbonyl [3- (trifluoromethoxy) 5-fluoropyrimidin-2-yl phenyl] thio
1-404 Methyl Methoxycarbonyl (3,5- Pyrimidin-2-yl dimethylphenyl)thio  1-404 methyl methoxycarbonyl (3,5-pyrimidin-2-yl dimethylphenyl) thio
1-405 Methyl Methyl (3- 5-Fluorpyrimidin-2-yl methylsulfanylphenyl)  1-405 methyl methyl (3-5-fluoropyrimidin-2-yl methylsulfanylphenyl)
thio  thio
1-406 Methyl Methyl (3- 5-Fluorpyrimidin-2-yl methoxyphenyl)methyl  1-406 methyl methyl (3-5-fluoropyrimidin-2-ylmethoxyphenyl) methyl
1-407 Methyl Methyl (3,5- 5-Fluorpyrimidin-2-yl dimethylphenyl)thio  1-407 methyl methyl (3,5- 5-fluoropyrimidin-2-yl dimethylphenyl) thio
1-408 Methyl Methyl (3,5- 5-Fluorpyrimidin-2-yl dimethoxyphenyl)thio  1-408 methyl methyl (3,5- 5-fluoropyrimidin-2-yl dimethoxyphenyl) thio
1-409 Methyl Methyl (3,5- Pyrimidin-2-yl dimethoxyphenyl)thio  1-409 methyl methyl (3,5-pyrimidin-2-yl dimethoxyphenyl) thio
1-410 Methyl Methoxycarbonyl (3,5- 5-Fluorpyrimidin-2-yl dimethylphenyl)thio  1-410 methyl methoxycarbonyl (3,5- 5-fluoropyrimidin-2-yl dimethylphenyl) thio
1-411 Methyl Methoxycarbonyl (3-methylphenyl)thio 5-Fluorpyrimidin-2-yl 1-411 methyl methoxycarbonyl (3-methylphenyl) thio 5-fluoropyrimidin-2-yl
1-412 Methyl Methoxycarbonyl (3- 5-Fluorpyrimidin-2-yl methylsulfanylphenyl) 1-412 methyl methoxycarbonyl (3-5-fluoropyrimidin-2-ylmethylsulfanylphenyl)
thio  thio
1-413 Methyl Methoxycarbonyl (3-ethoxyphenyl)thio 5-Fluorpyrimidin-2-yl 1-413 methyl methoxycarbonyl (3-ethoxyphenyl) thio 5-fluoropyrimidin-2-yl
1-414 Methyl Methyl (3,5-dimethoxyphenyl) Pyrimidin-2-yl methyl 1-414 methyl methyl (3,5-dimethoxyphenyl) pyrimidin-2-yl methyl
1-415 Methyl Methoxycarbonyl (3-methoxyphenyl)thio 5-Fluorpyrimidin-2-yl 1-415 methyl methoxycarbonyl (3-methoxyphenyl) thio 5-fluoropyrimidin-2-yl
1-416 Methyl Methyl (3- Pyrimidin-2-yl methoxyphenyl)methyl 1-416 methyl methyl (3-pyrimidin-2-yl methoxyphenyl) methyl
1-417 Methyl Methoxycarbonyl (3,5-dimethoxyphenyl) Pyrimidin-2-yl methyl  1-417 methyl methoxycarbonyl (3,5-dimethoxyphenyl) pyrimidin-2-yl methyl
1-418 Methyl Methyl (3,5-dimethoxyphenyl) 5-Fluorpyrimidin-2-yl methyl  1-418 methyl methyl (3,5-dimethoxyphenyl) 5-fluoropyrimidin-2-yl methyl
1-419 Methyl Methoxycarbonyl (3- Pyrimidin-2-yl methoxyphenyl)methyl  1-419 methyl methoxycarbonyl (3-pyrimidin-2-ylmethoxyphenyl) methyl
1-420 Methyl Methoxycarbonyl (3- 5-Fluorpyrimidin-2-yl methoxyphenyl)methyl  1-420 methyl methoxycarbonyl (3-5-fluoropyrimidin-2-ylmethoxyphenyl) methyl
1-421 Methyl Methoxycarbonyl (3,5-dimethoxyphenyl) 5-Fluorpyrimidin-2-yl methyl  1-421 Methyl methoxycarbonyl (3,5-dimethoxyphenyl) 5-fluoropyrimidin-2-yl methyl
1-422 Methyl Methoxycarbonyl (3-methoxyphenyl)thio Pyrimidin-2-yl 1-422 methyl methoxycarbonyl (3-methoxyphenyl) thio pyrimidin-2-yl
1-423 Methyl Methyl (3-ethoxyphenyl)thio 5-Fluorpyrimidin-2-yl Beispiel1 R2 A-Q1 Q2 nummer 1-423 methyl methyl (3-ethoxyphenyl) thio 5-fluoropyrimidin-2-yl Example 1 R 2 AQ 1 Q 2 number
1-424 Methyl Methoxycarbonyl (3,5- Pyrimidin-2-yl dimethoxyphenyl)thio  1-424 methyl methoxycarbonyl (3,5-pyrimidin-2-yl-dimethoxyphenyl) thio
1-425 Methyl Methoxycarbonyl (3,5- 5-Fluorpyrimidin-2-yl dimethoxyphenyl)thio  1-425 methyl methoxycarbonyl (3,5- 5-fluoropyrimidin-2-yl dimethoxyphenyl) thio
1-426 Methyl Methyl (4-Fluor-3- Pyrimidin-2-yl methoxyphenyl)thio  1-426 methyl methyl (4-fluoro-3-pyrimidin-2-yl methoxyphenyl) thio
1-427 Methyl Methoxycarbonyl (5-Chlorpyrimidin-2- 5-Fluorpyrimidin-2-yl yl)oxy  1-427 methyl methoxycarbonyl (5-chloropyrimidine-2-5-fluoropyrimidin-2-yl yl) oxy
1-428 Methyl Ethoxycarbonyl (4-Fluorphenyl)thio 5-Chlorpyrimidin-2-yl 1-428 methyl ethoxycarbonyl (4-fluorophenyl) thio 5-chloropyrimidin-2-yl
1-429 Methyl Methyl (2,3,4- Pyrimidin-2-yl 1-429 methyl methyl (2,3,4-pyrimidin-2-yl
Trifluorphenyl)thio  Trifluorophenyl) thio
1-430 Methyl Methyl (4-Fluor-3- 5-Fluorpyrimidin-2-yl methoxyphenyl)thio  1-430 methyl methyl (4-fluoro-3-5-fluoropyrimidin-2-yl methoxyphenyl) thio
1-431 Methyl Methoxycarbonyl (2,3,4- Pyrimidin-2-yl  1-431 methyl methoxycarbonyl (2,3,4-pyrimidin-2-yl
Trifluorphenyl)thio  Trifluorophenyl) thio
1-431 Methyl Methoxycarbonyl (2,3,4- Pyrimidin-2-yl  1-431 methyl methoxycarbonyl (2,3,4-pyrimidin-2-yl
Trifluorphenyl)thio  Trifluorophenyl) thio
1-432 Methyl Methoxycarbonyl (5-Fluorpyrimidin-2- 5-Fluorpyrimidin-2-yl yl)oxy  1-432 methyl methoxycarbonyl (5-fluoropyrimidine-2-5-fluoropyrimidin-2-yl yl) oxy
1-433 Methyl Methoxycarbonyl (4-Fluor-3- 5-Fluorpyrimidin-2-yl methoxyphenyl)thio  1-433 methyl methoxycarbonyl (4-fluoro-3-5-fluoropyrimidin-2-yl methoxyphenyl) thio
1-434 Methyl carboxy (4-Fluorphenyl)methyl 5-Fluorpyrimidin-2-yl 1-434 Methyl carboxy (4-fluorophenyl) methyl 5-fluoropyrimidin-2-yl
1-435 Methyl Methoxycarbonyl [5- 5-Fluorpyrimidin-2-yl 1-435 methyl methoxycarbonyl [5-5-fluoropyrimidin-2-yl
(Trifluormethyl)pyridin- 2-yl]oxy  (Trifluoromethyl) pyridin-2-yl] oxy
1-436 Methyl Methoxycarbonyl (5-Chlorpyrimidin-2- Pyrimidin-2-yl yl)oxy  1-436 methyl methoxycarbonyl (5-chloropyrimidine-2-pyrimidin-2-yl yl) oxy
1-437 Methyl Methoxycarbonyl (5-Fluorpyrimidin-2- Pyrimidin-2-yl yl)oxy  1-437 Methyl Methoxycarbonyl (5-fluoropyrimidine-2-pyrimidin-2-yl-yl) oxy
1-438 Methyl Methoxycarbonyl [5- Pyrimidin-2-yl  1-438 methyl methoxycarbonyl [5-pyrimidin-2-yl
(Trifluormethyl)pyridin- 2-yl]oxy  (Trifluoromethyl) pyridin-2-yl] oxy
1-439 Methyl Carboxy (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl 1-439 methyl carboxy (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl
1-440 H Methyl 2-phenylpropan-2-yl Pyrimidin-2-yl1-440H methyl 2-phenylpropan-2-yl pyrimidin-2-yl
1-441 H Methyl 2-phenylpropan-2-yl 5-Fluorpyrimidin-2-yl1-441H Methyl 2-phenylpropan-2-yl 5-fluoropyrimidin-2-yl
1-442 Methyl Methyl 2-phenylpropan-2-yl 5-Fluorpyrimidin-2-yl1-442 methyl methyl 2-phenylpropan-2-yl 5-fluoropyrimidin-2-yl
1-443 Methyl Methyl 2-phenylpropan-2-yl Pyrimidin-2-yl1-443 methyl methyl 2-phenylpropan-2-yl pyrimidin-2-yl
1-444 H Methyl 1-Phenylethyl Pyrimidin-2-yl 1-444 H methyl 1-phenylethyl pyrimidin-2-yl
1-445 H Methyl l-(3,4- Pyrimidin-2-yl 1-445H methyl 1- (3,4-pyrimidin-2-yl
Difluorphenyl)ethyl  Difluorophenyl) ethyl
1-446 H Methyl l-Pyridin-2-ylethyl Pyrimidin-2-yl 1-446 H methyl 1-pyridin-2-yl-ethyl pyrimidin-2-yl
1-447 Methyl Methyl l-Pyridin-2-ylethyl Pyrimidin-2-yl1-447 methyl methyl 1-pyridin-2-ylethyl pyrimidin-2-yl
1-448 Methyl Methyl l-(3,4- Pyrimidin-2-yl 1-448 methyl methyl 1- (3,4-pyrimidin-2-yl
Difluorphenyl)ethyl  Difluorophenyl) ethyl
1-449 Methyl Methyl 1-Phenylethyl Pyrimidin-2-yl 1-449 methyl methyl 1-phenylethyl pyrimidin-2-yl
1-450 Methyl Methyl 1-Phenylethyl 5-Fluorpyrimidin-2-yl Beispiel1 R2 A-Q1 Q2 nummer 1-450 methyl methyl 1-phenylethyl 5-fluoropyrimidin-2-yl Example 1 R 2 AQ 1 Q 2 number
1-451 Methyl Methyl l-(3,4- 5-Fluorpyrimidin-2-yl  1-451 methyl methyl 1- (3,4-5-fluoropyrimidin-2-yl
Difluorphenyl)ethyl  Difluorophenyl) ethyl
1-452 Methyl Methyl l-Pyridin-2-ylethyl 5-Fluorpyrimidin-2-yl 1-452 methyl methyl 1-pyridin-2-ylethyl 5-fluoropyrimidin-2-yl
1-453 H Methyl l-Pyridin-2-ylethyl 5-Fluorpyrimidin-2-yl1-453H Methyl 1-pyridin-2-ylethyl 5-fluoropyrimidin-2-yl
1-454 H Methyl l-(3,4- 5-Fluorpyrimidin-2-yl 1-454H methyl 1- (3,4-5-fluoropyrimidin-2-yl
Difluorphenyl)ethyl  Difluorophenyl) ethyl
1-455 H Methyl 1-Phenylethyl 5-Fluorpyrimidin-2-yl 1-455H Methyl 1-phenylethyl 5-fluoropyrimidin-2-yl
1-456 Methyl Methyl (2,3,4- 5-Fluorpyrimidin-2-yl 1-456 methyl methyl (2,3,4-5-fluoropyrimidin-2-yl
Trifluorphenyl)thio  Trifluorophenyl) thio
1-457 Methyl Methoxycarbonyl (4-Fluor-3- Pyrimidin-2-yl methoxyphenyl)thio  1-457 methyl methoxycarbonyl (4-fluoro-3-pyrimidin-2-ylmethoxyphenyl) thio
1-458 Methyl Methoxycarbonyl (2,3,4- 5-Fluorpyrimidin-2-yl  1-458 methyl methoxycarbonyl (2,3,4-5-fluoropyrimidin-2-yl
Trifluorphenyl)thio  Trifluorophenyl) thio
1-459 Methyl Cyclohexyloxycarb (4-Fluorphenyl)methyl 5-Fluorpyrimidin-2-yl onyl  1-459 methyl cyclohexyloxycarb (4-fluorophenyl) methyl 5-fluoropyrimidin-2-ylonyl
1-460 Methyl Cyclohexyloxycarb (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl onyl  1-460 methyl cyclohexyloxycarb (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl onyl
1-461 H Methyl (2,4- 5-Fluorpyrimidin-2-yl  1-461H methyl (2,4-5-fluoropyrimidin-2-yl
Difluorphenyl)methyl  Difluorophenyl) methyl
1-462 Methyl Methyl 2,4-Difluorphenoxy 6- 1-462 methyl methyl 2,4-difluorophenoxy 6-
(Trifluormethyl)pyridazin- 3-yl (Trifluoromethyl) pyridazin-3-yl
1-463 Methyl Methyl (3-Fluorphenyl)methyl 5-Fluorpyrimidin-2-yl 1-463 methyl methyl (3-fluorophenyl) methyl 5-fluoropyrimidin-2-yl
1-464 Methyl Methyl 2,4-Difluorphenoxy 6-Cyanopyridazin-3-yl1-464 methyl methyl 2,4-difluorophenoxy 6-cyanopyridazin-3-yl
1-465 Methyl Methyl 2,4-Difluorphenoxy 6-Chlorpyridazin-3-yl1-465 methyl methyl 2,4-difluorophenoxy 6-chloropyridazin-3-yl
1-466 Methyl Ethoxycarbonyl 4-Fluorphenoxy 5-Chlorpyrimidin-2-yl1-466 methyl ethoxycarbonyl 4-fluorophenoxy 5-chloropyrimidin-2-yl
1-467 H Methyl 2,4-Difluorphenoxy 5-Fluorpyrimidin-2-yl1-467 H Methyl 2,4-Difluorophenoxy 5-fluoropyrimidin-2-yl
1-468 Methyl Methyl 2,4-Difluoranilin Pyrimidin-2-yl1-468 methyl methyl 2,4-difluoroaniline pyrimidin-2-yl
1-469 Methyl Methoxycarbonyl (4-Fluorphenyl)thio Pyrimidin-2-yl methyl 1-469 methyl methoxycarbonyl (4-fluorophenyl) thio pyrimidin-2-yl methyl
1-470 Methyl Methoxycarbonyl 4-Fluorphenoxy Pyrimidin-2-yl methyl  1-470 methyl methoxycarbonyl 4-fluorophenoxy pyrimidin-2-yl methyl
1-471 Methyl Methoxycarbonyl (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl methyl  1-471 methyl methoxycarbonyl (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl methyl
1-472 Methyl Methoxycarbonyl 4-Fluorphenoxy 5-Fluorpyrimidin-2-yl methyl  1-472 methyl methoxycarbonyl 4-fluorophenoxy 5-fluoropyrimidin-2-yl methyl
1-473 Methyl Cyanomethyl (4-Fluorphenyl)thio Pyrimidin-2-yl 1-473 methyl cyanomethyl (4-fluorophenyl) thio pyrimidin-2-yl
1-474 Methyl Cyanomethyl 4-Fluorphenoxy Pyrimidin-2-yl1-474 methyl cyanomethyl 4-fluorophenoxy pyrimidin-2-yl
1-475 Methyl Cyanomethyl (4-Fluorphenyl)thio 5-Fluorpyrimidin-2-yl 1-475 methyl cyanomethyl (4-fluorophenyl) thio 5-fluoropyrimidin-2-yl
In Analogie zu den oben angeführten und an entsprechender Stelle rezitierten Herstellungsbeispielen und unter Berücksichtigung der allgemeinen Angaben zur Herstellung von substituierten In analogy to the production examples recited above and recited in the appropriate place and taking into account the general information for the preparation of substituted
(Het-)Arylpyrazolamiden erhält man die nachfolgend genannten und in Tabelle II dargestellten (Het-) Arylpyrazolamiden gives the following and shown in Table II
Intermediate der allgemeinen Formel (II) Intermediates of the general formula (II)
Tabelle IITable II
BeispielXI X2 X3 X4 nummer ExampleXI X2 X3 X4 number
A-39 Hydroxy (3 -Chlorphenyl)thio Methyl Methyl  A-39 hydroxy (3-chlorophenyl) thio methyl methyl
A-40 Hydroxy (3,4- Methyl Methyl A-40 hydroxy (3,4-methyl methyl
Difluorphenyl)thio  Difluorophenyl) thio
A-41 Hydroxy Phenylsulfanyl Cyclopropyl Methyl  A-41 Hydroxy Phenylsulfanyl Cyclopropyl Methyl
A-42 Hydroxy (3 -Chlorphenyl)thio Cyclopropyl Methyl A-42 hydroxy (3-chlorophenyl) thio cyclopropyl methyl
A-43 Hydroxy (3,4- Cyclopropyl Methyl A-43 hydroxy (3,4-cyclopropyl methyl
Difluorphenyl)thio  Difluorophenyl) thio
A-44 Methoxy (3- Methyl Methyl  A-44 methoxy (3-methyl methyl
Trifluorphenyl)thio  Trifluorophenyl) thio
A-45 Methoxy (3,4- Methyl Methyl  A-45 methoxy (3,4-methyl methyl
Difluorphenyl)thio  Difluorophenyl) thio
A-46 Methoxy (3 -Chlorphenyl)thio Methyl Methyl  A-46 Methoxy (3-chlorophenyl) thio methyl methyl
A-47 Methoxy (2,4- Methyl Methyl A-47 methoxy (2,4-methyl methyl
Difluorphenyl)thio  Difluorophenyl) thio
A-48 Methoxy Phenylsulfanyl Cyclopropyl Methyl  A-48 Methoxy Phenylsulfanyl Cyclopropyl Methyl
A-49 (5-Chlorpyrimidin-2- lod Methoxycarbonyl Methyl yl)oxy A-49 (5-chloropyrimidine-2-iodo methoxycarbonylmethyl) oxy
NMR-Daten ausgewählter Beispiele (Endprodukte und Intermediate) NMR-Peak-Listenverfahren NMR data of selected examples (final products and intermediates) NMR peak list method
Die 1H-NMR-Daten ausgewählter Beispiele werden in Form von 1H-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der δ-Wert in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die δ-Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. The 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The δ-value signal intensity number pairs of different signal peaks are listed separated by semicolons.
Die Peakliste eines Beispieles hat daher die Form: δι (Intensität^; 82 (Intensität2); ; δ; (Intensität^; ; δη (Intensitätn) The peak list of an example therefore has the form: δι (intensity ^; 82 (intensity 2);; δ; (intensity ^;; δ η (intensity n )
Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In broad Signals can show multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum.
Zur Kalibrierung der chemischen Verschiebung von 1H-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondern im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. To calibrate the chemical shift of 1H NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
Die Listen der IH-NMR-Peaks sind ähnlich den klassischen IH-NMR- Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. The lists of the IH-NMR peaks are similar to the classical IH-NMR prints and thus usually contain all the peaks that are listed in a classical NMR interpretation.
Darüber hinaus können sie wie klassische IH-NMR- Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. In addition, like classical IH-NMR prints, they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.
Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von IH-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. When indicating compound signals in the delta range of solvents and / or water, our lists of IH NMR peaks show the usual solvent peaks, for example, peaks of DMSO in DMSO-D6 and the peak of water, which are usually average have a high intensity.
Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90 %). Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%). Such stereoisomers and / or impurities may be typical of each
Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres  Be manufacturing process. Their peaks can thus help the reproduction of our
Herstellungsverfahrens anhand von "Nebenprodukt-Fingerabdrucken" zu erkennen. Detect manufacturing process by "by-product fingerprints".
Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR- Interpretation. An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can isolate the peaks of the target compounds as needed, using additional intensity filters, if necessary. This isolation would be similar to peak picking in classical 1H NMR interpretation.
Weitere Details zu 1H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. NMR-Daten der Endprodukte (Peakliste) Further details on 1H NMR peaks can be found in Research Disclosure Database Number 564025. NMR data of the final products (peak list)
1-004: 'H-NMR^OO.O MHz, CDC13):  1-004: 'H NMR ^ OO.O MHz, CDC13):
δ= 8.5000 (6.2); 8.4880 (6.3); 7.5525 (2.2); 7.5507 (2.3); 7.5484 (2.1); 7.5342 (0.7); 7.5304 (1.1); 7.4231 (1.1); 7.4192 (1.7); 7.4138 (1.9); 7.3961 (1.1); 7.3946 (1.0); 7.2608 (24.6); 6.9801 (1.9); 6.9681 (3.6); 6.9561 (1.8); 3.8339 (16.0); 2.3769 (15.6); -δ = 8.5000 (6.2); 8.4880 (6.3); 7.5525 (2.2); 7.5507 (2.3); 7.5484 (2.1); 7.5342 (0.7); 7.5304 (1.1); 7.4231 (1.1); 7.4192 (1.7); 7.4138 (1.9); 7.3961 (1.1); 7.3946 (1.0); 7.2608 (24.6); 6.9801 (1.9); 6.9681 (3.6); 6.9561 (1.8); 3.8339 (16.0); 2.3769 (15.6); -
0.0002 (9.3) 0.0002 (9.3)
1-005: Ή-ΝΜϋ^ΟΟ.Ο MHz, CDC13):  1-005: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, CDC13):
δ= 8.5276 (6.0); 8.5156 (6.1); 7.2615 (21.5); 7.0129 (1.8); 7.0010 (3.5); 6.9890 (1.7); 6.8824 (1.6); 6.8766 (1.9); 6.8735 (1.0); 6.8640 (1.0); 6.8609 (1.9); 6.8551 (1.7); 6.6446 (0.8); 6.6279 (0.8); 6.6220 (1.5); 6.6162 (0.8); 6.5994 (0.8); 3.8183 (16.0);δ = 8.5276 (6.0); 8.5156 (6.1); 7.2615 (21.5); 7.0129 (1.8); 7.0010 (3.5); 6.9890 (1.7); 6.8824 (1.6); 6.8766 (1.9); 6.8735 (1.0); 6.8640 (1.0); 6.8609 (1.9); 6.8551 (1.7); 6.6446 (0.8); 6.6279 (0.8); 6.6220 (1.5); 6.6162 (0.8); 6.5994 (0.8); 3.8183 (16.0);
2.3836 (15.8); 1.5709 (0.8); -0.0002 (7.9) 2.3836 (15.8); 1.5709 (0.8); -0.0002 (7.9)
1-006: 1H-NMR(400.0 MHz, CDC13): 1-006: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4972 (4.3); 8.4852 (4.4); 7.3528 (1.3); 7.3492 (1.7); 7.3441 (0.6); 7.3365 (0.8); 7.3340 (1.4); 7.3318 (3.0); 7.3285 (2.4); 7.3010 (1.9); 7.2960 (0.6); 7.2839 (1.9); 7.2825 (2.9); 7.2787 (1.0); 7.2670 (0.8); 7.2599 (24.9); 7.1929 (0.6); 7.1893 (1.1); 7.1856 (0.6); 7.1711 (1.2); 7.1530 (0.6); 6.9605 (1.6); 6.9485 (3.1); 6.9365 (1.6); 3.8241 (16.0); 2.3705 (15.3); -0.0002 (9.6) 1-007: 1H-NMR(400.0 MHz, CDC13): δ = 8.4972 (4.3); 8.4852 (4.4); 7.3528 (1.3); 7.3492 (1.7); 7.3441 (0.6); 7.3365 (0.8); 7.3340 (1.4); 7.3318 (3.0); 7.3285 (2.4); 7.3010 (1.9); 7.2960 (0.6); 7.2839 (1.9); 7.2825 (2.9); 7.2787 (1.0); 7.2670 (0.8); 7.2599 (24.9); 7.1929 (0.6); 7.1893 (1.1); 7.1856 (0.6); 7.1711 (1.2); 7.1530 (0.6); 6.9605 (1.6); 6.9485 (3.1); 6.9365 (1.6); 3.8241 (16.0); 2.3705 (15.3); -0.0002 (9.6) 1-007: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4304 (1.5); 8.3345 (11.0); 8.0764 (1.1); 7.5535 (1.2); 7.5518 (1.5); 7.5500 (1.3); 7.5476 (1.0); 7.5420 (0.5); 7.5406 (0.5); 7.5379 (0.7); 7.5365 (0.6); 7.5229 (0.6); 7.5198 (1.0); 7.4431 (0.9); 7.4400 (1.3); 7.4312 (1.3); 7.4132 (1.0); 7.2613 (15.9); 7.1569 (0.5); 5.2981 (1.1); 3.8366 (0.6); 3.8297 (16.0); 3.7910 (1.3); 3.7317 (2.5); 2.3778 (15.3); 2.3394 (1.2); 2.2894 (1.5);δ = 8.4304 (1.5); 8.3345 (11.0); 8.0764 (1.1); 7.5535 (1.2); 7.5518 (1.5); 7.5500 (1.3); 7.5476 (1.0); 7.5420 (0.5); 7.5406 (0.5); 7.5379 (0.7); 7.5365 (0.6); 7.5229 (0.6); 7.5198 (1.0); 7.4431 (0.9); 7.4400 (1.3); 7.4312 (1.3); 7.4132 (1.0); 7.2613 (15.9); 7.1569 (0.5); 5.2981 (1.1); 3.8366 (0.6); 3.8297 (16.0); 3.7910 (1.3); 3.7317 (2.5); 2.3778 (15.3); 2.3394 (1.2); 2.2894 (1.5);
2.2880 (1.4); 1.5639 (1.8); -0.0002 (9.5) 2.2880 (1.4); 1.5639 (1.8); -0.0002 (9.5)
1-009: 1H-NMR(400.0 MHz, CDC13): 1-009: 1 H-NMR (400.0 MHz, CDC13):
δ= 9.3469 (0.5); 9.0618 (3.3); 8.9992 (1.6); 8.7305 (8.8); 8.3723 (12.0); 7.2638 (20.7); 5.2995 (2.8); 3.8455 (16.0); 2.4051 (15.0);δ = 9.3469 (0.5); 9.0618 (3.3); 8.9992 (1.6); 8.7305 (8.8); 8.3723 (12.0); 7.2638 (20.7); 5.2995 (2.8); 3.8455 (16.0); 2.4051 (15.0);
-0.0002 (8.9) -0.0002 (8.9)
1-011 : 1H-NMR(400.0 MHz, CDC13): 1-011: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4353 (0.6); 8.3629 (11.0); 7.2619 (12.0); 6.8750 (1.5); 6.8717 (1.0); 6.8692 (1.7); 6.8661 (0.9); 6.8578 (0.8); 6.8567 (0.8); 6.8536 (1.7); 6.8479 (1.5); 6.6636 (0.7); 6.6469 (0.8); 6.6411 (1.4); 6.6352 (0.6); 6.6185 (0.7); 5.2983 (2.3); 3.8152 (16.0);δ = 8.4353 (0.6); 8.3629 (11.0); 7.2619 (12.0); 6.8750 (1.5); 6.8717 (1.0); 6.8692 (1.7); 6.8661 (0.9); 6.8578 (0.8); 6.8567 (0.8); 6.8536 (1.7); 6.8479 (1.5); 6.6636 (0.7); 6.6469 (0.8); 6.6411 (1.4); 6.6352 (0.6); 6.6185 (0.7); 5.2983 (2.3); 3.8152 (16.0);
3.7542 (1.1); 2.3844 (15.4); 2.2973 (0.7); 2.2961 (0.6); -0.0002 (5.1) 3.7542 (1.1); 2.3844 (15.4); 2.2973 (0.7); 2.2961 (0.6); -0.0002 (5.1)
1-013: 1H-NMR(400.0 MHz, CDC13): 1-013: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.5247 (4.6); 8.5127 (4.6); 7.2609 (24.8); 7.1611 (0.5); 7.1560 (0.5); 7.1375 (0.5); 7.1105 (0.6); 7.1079 (0.6); 7.0873 (0.8); 7.0702 (1.1); 7.0685 (2.1); 7.0637 (1.8); 7.0562 (0.8); 7.0513 (1.9); 7.0481 (1.5); 7.0156 (1.7); 7.0036 (3.3); 6.9916 (1.7); 3.8187δ = 8.5247 (4.6); 8.5127 (4.6); 7.2609 (24.8); 7.1611 (0.5); 7.1560 (0.5); 7.1375 (0.5); 7.1105 (0.6); 7.1079 (0.6); 7.0873 (0.8); 7.0702 (1.1); 7.0685 (2.1); 7.0637 (1.8); 7.0562 (0.8); 7.0513 (1.9); 7.0481 (1.5); 7.0156 (1.7); 7.0036 (3.3); 6.9916 (1.7); 3.8187
(16.0); 2.3518 (15.0); -0.0002 (9.3) (16.0); 2.3518 (15.0); -0.0002 (9.3)
1-015: 1H-NMR(400.0 MHz, de-DMSO): 1-015: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.7223 (15.3); 7.3057 (1.8); 7.3002 (0.7); 7.2919 (2.0); 7.2834 (2.5); 7.2754 (0.9); 7.2696 (2.2); 7.1508 (2.3); 7.1452 (0.7); 7.1340 (0.8); 7.1284 (4.0); 7.1227 (0.8); 7.1114 (0.6); 7.1059 (1.8); 5.7535 (1.6); 4.0666 (15.8); 3.7053 (16.0); 3.3134 (4.2); 2.5234 (1.2); 2.5187 (1.6); 2.5100 (14.9); 2.5055 (30.3); 2.5009 (41.0); 2.4964 (28.4); 2.4919 (12.9); 0.0080 (0.9); -0.0002 (24.6);δ = 8.7223 (15.3); 7.3057 (1.8); 7.3002 (0.7); 7.2919 (2.0); 7.2834 (2.5); 7.2754 (0.9); 7.2696 (2.2); 7.1508 (2.3); 7.1452 (0.7); 7.1340 (0.8); 7.1284 (4.0); 7.1227 (0.8); 7.1114 (0.6); 7.1059 (1.8); 5.7535 (1.6); 4.0666 (15.8); 3.7053 (16.0); 3.3134 (4.2); 2.5234 (1.2); 2.5187 (1.6); 2,5100 (14.9); 2.5055 (30.3); 2,5009 (41.0); 2.4964 (28.4); 2.4919 (12.9); 0.0080 (0.9); -0.0002 (24.6);
-0.0085 (0.8) -0.0085 (0.8)
1-016: 1H-NMR(400.0 MHz, CDC13): 1-016: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3241 (11.0); 7.2596 (81.0); 7.0649 (1.1); 7.0513 (1.2); 7.0430 (1.5); 7.0351 (0.6); 7.0295 (1.4); 6.8684 (1.8); 6.8631 (0.5); 6.8520 (0.6); 6.8466 (3.3); 6.8412 (0.6); 6.8248 (1.4); 3.7397 (16.0); 3.5939 (4.4); 2.1584 (14.0); 1.5420 (2.5); 0.0079 (0.9); -δ = 8.3241 (11.0); 7.2596 (81.0); 7.0649 (1.1); 7.0513 (1.2); 7.0430 (1.5); 7.0351 (0.6); 7.0295 (1.4); 6.8684 (1.8); 6.8631 (0.5); 6.8520 (0.6); 6.8466 (3.3); 6.8412 (0.6); 6.8248 (1.4); 3.7397 (16.0); 3.5939 (4.4); 2.1584 (14.0); 1.5420 (2.5); 0.0079 (0.9); -
0.0002 (28.1); -0.0085 (0.8) 0.0002 (28.1); -0.0085 (0.8)
1-017: 1H-NMR(400.0 MHz, CDC13): 1-017: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.1334 (5.0); 7.2619 (14.8); 7.0711 (1.0); 7.0575 (1.1); 7.0493 (1.3); 7.0358 (1.2); 6.8608 (1.6); 6.8555 (0.5); 6.8443 (0.5); 6.8389 (2.9); 6.8335 (0.5); 6.8171 (1.3); 3.8812 (0.9); 3.8371 (16.0); 3.7287 (12.6); 3.5879 (3.7); 2.1439 (12.0); -0.0002 (5.2) 1-018: 1H-NMR(400.0 MHz, CDC13): δ = 8.1334 (5.0); 7.2619 (14.8); 7.0711 (1.0); 7.0575 (1.1); 7.0493 (1.3); 7.0358 (1.2); 6.8608 (1.6); 6.8555 (0.5); 6.8443 (0.5); 6.8389 (2.9); 6.8335 (0.5); 6.8171 (1.3); 3.8812 (0.9); 3.8371 (16.0); 3.7287 (12.6); 3.5879 (3.7); 2.1439 (12.0); -0.0002 (5.2) 1-018: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4938 (1.3); 7.2600 (42.1); 7.1788 (0.7); 7.1759 (1.1); 7.1719 (0.5); 7.1604 (1.9); 7.1578 (2.8); 7.1550 (2.1); 7.1455 (1.0); 7.1402 (3.5); 7.1160 (4.2); 7.1099 (0.9); 7.0993 (2.4); 7.0898 (0.7); 7.0837 (1.5); 6.9786 (0.7); 6.9671 (1.1); 6.9554 (0.6); 4.1302 (1.5); 4.1124 (1.5); 4.0945 (0.5); 3.7359 (16.0); 3.6277 (7.5); 2.1519 (15.9); 2.0432 (6.8); 1.2762 (1.9); 1.2583 (4.4); 1.2404δ = 8.4938 (1.3); 7.2600 (42.1); 7.1788 (0.7); 7.1759 (1.1); 7.1719 (0.5); 7.1604 (1.9); 7.1578 (2.8); 7.1550 (2.1); 7.1455 (1.0); 7.1402 (3.5); 7.1160 (4.2); 7.1099 (0.9); 7.0993 (2.4); 7.0898 (0.7); 7.0837 (1.5); 6.9786 (0.7); 6.9671 (1.1); 6.9554 (0.6); 4.1302 (1.5); 4.1124 (1.5); 4.0945 (0.5); 3.7359 (16.0); 3.6277 (7.5); 2.1519 (15.9); 2.0432 (6.8); 1.2762 (1.9); 1.2583 (4.4); 1.2404
(1.8); 0.0080 (0.5); -0.0002 (16.0); -0.0085 (0.5) (1.8); 0.0080 (0.5); -0.0002 (16.0); -0.0085 (0.5)
1-019: 1H-NMR(400.0 MHz, CDC13): 1-019: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4949 (5.8); 8.4830 (5.9); 7.5184 (0.8); 7.2694 (0.8); 7.2595 (152.1); 7.0774 (1.1); 7.0637 (1.2); 7.0555 (1.5); 7.0419 (1.4); 6.9955 (0.8); 6.9899 (1.7); 6.9780 (3.2); 6.9660 (1.6); 6.8540 (1.8); 6.8486 (0.6); 6.8375 (0.6); 6.8320 (3.2); 6.8264 (0.6); 6.8102δ = 8.4949 (5.8); 8.4830 (5.9); 7.5184 (0.8); 7.2694 (0.8); 7.2595 (152.1); 7.0774 (1.1); 7.0637 (1.2); 7.0555 (1.5); 7.0419 (1.4); 6.9955 (0.8); 6.9899 (1.7); 6.9780 (3.2); 6.9660 (1.6); 6.8540 (1.8); 6.8486 (0.6); 6.8375 (0.6); 6.8320 (3.2); 6.8264 (0.6); 6.8102
(1.4); 3.7419 (16.0); 3.5964 (4.3); 2.1523 (13.8); 1.5451 (3.6); 0.0080 (1.6); -0.0002 (52.8); -0.0085 (1.6) (1.4); 3.7419 (16.0); 3.5964 (4.3); 2.1523 (13.8); 1.5451 (3.6); 0.0080 (1.6); -0.0002 (52.8); -0.0085 (1.6)
1-020: 1H-NMR(400.0 MHz, CDC13): 1-020: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4799 (4.7); 8.4680 (4.8); 7.2612 (12.5); 7.2065 (1.5); 7.2012 (0.6); 7.1878 (2.2); 7.1847 (2.3); 7.1713 (0.7); 7.1663 (2.0); 6.9766 (1.5); 6.9646 (2.9); 6.9528 (2.3); 6.9346 (1.6); 6.9323 (1.5); 6.9270 (2.4); 6.9242 (2.6); 6.9188 (0.9); 6.9163 (0.8); 6.9135δ = 8.4799 (4.7); 8.4680 (4.8); 7.2612 (12.5); 7.2065 (1.5); 7.2012 (0.6); 7.1878 (2.2); 7.1847 (2.3); 7.1713 (0.7); 7.1663 (2.0); 6.9766 (1.5); 6.9646 (2.9); 6.9528 (2.3); 6.9346 (1.6); 6.9323 (1.5); 6.9270 (2.4); 6.9242 (2.6); 6.9188 (0.9); 6.9163 (0.8); 6.9135
(0.6); 6.9050 (2.3); 6.9031 (1.8); 5.2970 (1.8); 3.7696 (16.0); 2.1549 (15.6); 1.5793 (1.5); -0.0002 (4.6) (0.6); 6.9050 (2.3); 6.9031 (1.8); 5.2970 (1.8); 3.7696 (16.0); 2.1549 (15.6); 1.5793 (1.5); -0.0002 (4.6)
1-023: 1H-NMR(400.0 MHz, CDC13): 1-023: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3048 (10.6); 7.2596 (46.5); 7.2170 (1.5); 7.2116 (0.6); 7.1984 (2.2); 7.1952 (2.2); 7.1817 (0.7); 7.1768 (2.0); 6.9683 (0.9); 6.9658 (0.6); 6.9499 (1.6); 6.9315 (0.7); 6.9128 (2.1); 6.9101 (2.6); 6.9048 (0.7); 6.8934 (1.2); 6.8907 (2.2); 6.8884 (1.8); 4.1305 (0.6); 4.1126 (0.7); 3.7669 (16.0); 2.1569 (15.6); 2.0434 (3.0); 1.5403 (8.5); 1.2763 (1.0); 1.2585 (2.0); 1.2406 (0.8); 0.8819δ = 8.3048 (10.6); 7.2596 (46.5); 7.2170 (1.5); 7.2116 (0.6); 7.1984 (2.2); 7.1952 (2.2); 7.1817 (0.7); 7.1768 (2.0); 6.9683 (0.9); 6.9658 (0.6); 6.9499 (1.6); 6.9315 (0.7); 6.9128 (2.1); 6.9101 (2.6); 6.9048 (0.7); 6.8934 (1.2); 6.8907 (2.2); 6.8884 (1.8); 4.1305 (0.6); 4.1126 (0.7); 3.7669 (16.0); 2.1569 (15.6); 2.0434 (3.0); 1.5403 (8.5); 1.2763 (1.0); 1.2585 (2.0); 1.2406 (0.8); 0.8819
(1.0); 0.0079 (0.5); -0.0002 (16.3); -0.0084 (0.5) (1.0); 0.0079 (0.5); -0.0002 (16.3); -0.0084 (0.5)
1-028: 'H-NMR(599.8 MHz, CDC13):  1-028: 'H-NMR (599.8 MHz, CDC13):
δ= 8.3588 (0.5); 8.3395 (10.4); 7.2604 (25.4); 6.9696 (0.5); 6.9608 (0.6); 6.9542 (1.1); 6.9454 (1.1); 6.9388 (0.6); 6.9300 (0.6); 6.8020 (0.6); 6.7971 (0.6); 6.7882 (0.6); 6.7837 (1.0); 6.7792 (0.6); 6.7703 (0.6); 6.7654 (0.6); 6.6924 (0.4); 6.6893 (0.4); 6.6876 (0.4); 6.6845 (0.4); 6.6794 (0.5); 6.6769 (0.7); 6.6744 (0.7); 6.6720 (0.6); 6.6694 (0.4); 6.6642 (0.4); 6.6612 (0.4); 6.6594 (0.4); 3.7592 (15.5); 3.6681 (0.7); 2.2079 (14.9); 2.1351 (0.6); 1.5449 (12.9); 0.1574 (0.4); 0.0053 (1.9); -0.0001 (50.0); -0.0056 (1.7) 1-026: 'H-NMR^OO.O MHz, CDC13): δ = 8.3588 (0.5); 8.3395 (10.4); 7.2604 (25.4); 6.9696 (0.5); 6.9608 (0.6); 6.9542 (1.1); 6.9454 (1.1); 6.9388 (0.6); 6.9300 (0.6); 6.8020 (0.6); 6.7971 (0.6); 6.7882 (0.6); 6.7837 (1.0); 6.7792 (0.6); 6.7703 (0.6); 6.7654 (0.6); 6.6924 (0.4); 6.6893 (0.4); 6.6876 (0.4); 6.6845 (0.4); 6.6794 (0.5); 6.6769 (0.7); 6.6744 (0.7); 6.6720 (0.6); 6.6694 (0.4); 6.6642 (0.4); 6.6612 (0.4); 6.6594 (0.4); 3.7592 (15.5); 3.6681 (0.7); 2.2079 (14.9); 2.1351 (0.6); 1.5449 (12.9); 0.1574 (0.4); 0.0053 (1.9); -0.0001 (50.0); -0.0056 (1.7) 1-026: 'H NMR ^ OO.O MHz, CDC13):
δ= 8.4981 (3.7); 8.4862 (3.8); 7.2607 (40.9); 7.0138 (1.6); 7.0052 (0.7); 7.0018 (3.1); 6.9917 (0.8); 6.9898 (1.7); 6.9823 (1.2); 6.9689 (1.1); 6.9592 (0.6); 6.9458 (0.6); 6.7864 (0.5); 6.7789 (0.6); 6.7654 (0.6); 6.7587 (0.9); 6.7521 (0.6); 6.7386 (0.5); 6.7313 (0.6); 6.6610 (0.5); 6.6575 (0.6); 6.6565 (0.6); 6.6533 (0.8); 6.6491 (0.5); 3.7619 (16.0); 2.9550 (1.2); 2.8839 (1.1); 2.8825 (1.1);δ = 8.4981 (3.7); 8.4862 (3.8); 7.2607 (40.9); 7.0138 (1.6); 7.0052 (0.7); 7.0018 (3.1); 6.9917 (0.8); 6.9898 (1.7); 6.9823 (1.2); 6.9689 (1.1); 6.9592 (0.6); 6.9458 (0.6); 6.7864 (0.5); 6.7789 (0.6); 6.7654 (0.6); 6.7587 (0.9); 6.7521 (0.6); 6.7386 (0.5); 6.7313 (0.6); 6.6610 (0.5); 6.6575 (0.6); 6.6565 (0.6); 6.6533 (0.8); 6.6491 (0.5); 3.7619 (16.0); 2.9550 (1.2); 2.8839 (1.1); 2.8825 (1.1);
2.2102 (14.5); 1.5552 (0.7); 1.2585 (0.5); -0.0002 (14.5); -0.0085 (0.6) 2.2102 (14.5); 1.5552 (0.7); 1.2585 (0.5); -0.0002 (14.5); -0.0085 (0.6)
1-030: Ή-ΝΜϋ^ΟΟ.Ο MHz, CDC13):  1-030: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, CDC13):
δ= 8.4963 (12.2); 7.2603 (38.0); 6.9750 (0.5); 6.9617 (0.6); 6.9520 (1.1); 6.9386 (1.1); 6.9289 (0.7); 6.9156 (0.6); 6.8169 (0.6); 6.8095 (0.6); 6.7961 (0.6); 6.7893 (0.9); 6.7826 (0.7); 6.7692 (0.6); 6.7618 (0.6); 6.6777 (0.6); 6.6743 (0.7); 6.6703 (0.6); 3.7573δ = 8.4963 (12.2); 7.2603 (38.0); 6.9750 (0.5); 6.9617 (0.6); 6.9520 (1.1); 6.9386 (1.1); 6.9289 (0.7); 6.9156 (0.6); 6.8169 (0.6); 6.8095 (0.6); 6.7961 (0.6); 6.7893 (0.9); 6.7826 (0.7); 6.7692 (0.6); 6.7618 (0.6); 6.6777 (0.6); 6.6743 (0.7); 6.6703 (0.6); 3.7573
(16.0); 2.2050 (14.8); 1.5439 (5.6); -0.0002 (13.0); -0.0085 (0.5) (16.0); 2.2050 (14.8); 1.5439 (5.6); -0.0002 (13.0); -0.0085 (0.5)
1-031 : 1H-NMR(400.0 MHz, CDC13): 1-031: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3314 (2.8); 8.3292 (3.0); 8.2347 (2.4); 8.2282 (2.7); 8.0288 (1.6); 8.0255 (2.0); 8.0225 (2.0); 8.0190 (1.8); 7.2614 (15.9); 6.9550 (0.6); 6.9417 (0.6); 6.9319 (1.2); 6.9187 (1.3); 6.9089 (0.8); 6.8957 (0.7); 6.7986 (0.6); 6.7913 (0.7); 6.7777 (0.7); 6.7709 (1.3); 6.7645 (0.9); 6.7509 (0.6); 6.7437 (0.7); 6.6867 (0.6); 6.6813 (0.5); 6.6692 (0.9); 6.6661 (1.0); 6.6625 (0.9); 6.6449 (0.5);δ = 8.3314 (2.8); 8.3292 (3.0); 8.2347 (2.4); 8.2282 (2.7); 8.0288 (1.6); 8.0255 (2.0); 8.0225 (2.0); 8.0190 (1.8); 7.2614 (15.9); 6.9550 (0.6); 6.9417 (0.6); 6.9319 (1.2); 6.9187 (1.3); 6.9089 (0.8); 6.8957 (0.7); 6.7986 (0.6); 6.7913 (0.7); 6.7777 (0.7); 6.7709 (1.3); 6.7645 (0.9); 6.7509 (0.6); 6.7437 (0.7); 6.6867 (0.6); 6.6813 (0.5); 6.6692 (0.9); 6.6661 (1.0); 6.6625 (0.9); 6.6449 (0.5);
3.7566 (16.0); 3.6595 (1.1); 2.2104 (15.5); 2.1383 (1.1); 1.5666 (2.6); 1.2559 (0.7); -0.0002 (5.6) 3.7566 (16.0); 3.6595 (1.1); 2.2104 (15.5); 2.1383 (1.1); 1.5666 (2.6); 1.2559 (0.7); -0.0002 (5.6)
1-033: 1H-NMR(400.0 MHz, CDC13): 1-033: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3763 (13.5); 7.8789 (0.6); 7.8726 (4.5); 7.8676 (1.8); 7.8631 (4.8); 7.8558 (1.6); 7.8508 (4.9); 7.8447 (0.6); 7.4500 (0.7); 7.4439 (4.9); 7.4388 (1.6); 7.4270 (1.4); 7.4220 (4.4); 7.4159 (0.5); 7.2605 (35.5); 5.2982 (1.0); 3.8895 (16.0); 1.5512 (11.2); -δ = 8.3763 (13.5); 7.8789 (0.6); 7.8726 (4.5); 7.8676 (1.8); 7.8631 (4.8); 7.8558 (1.6); 7.8508 (4.9); 7.8447 (0.6); 7.4500 (0.7); 7.4439 (4.9); 7.4388 (1.6); 7.4270 (1.4); 7.4220 (4.4); 7.4159 (0.5); 7.2605 (35.5); 5.2982 (1.0); 3.8895 (16.0); 1.5512 (11.2); -
0.0002 (13.5) 0.0002 (13.5)
1-034: 1H-NMR(400.0 MHz, de-DMSO): 1-034: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.7790 (0.3); 8.6436 (10.8); 8.6231 (0.4); 7.2775 (1.0); 7.2578 (2.4); 7.2384 (1.6); 7.1797 (1.6); 7.1578 (1.0); 7.0302 (1.4); 7.0264 (2.9); 7.0221 (3.7); 7.0029 (1.2); 7.0004 (1.3); 3.9030 (2.7); 3.8392 (0.7); 3.8282 (16.0); 3.3296 (143.7); 2.7403 (0.9); 2.7214 (2.9); 2.7024 (3.0); 2.6833 (1.0); 2.6761 (0.5); 2.6713 (0.6); 2.6669 (0.4); 2.5245 (1.4); 2.5108 (36.5); 2.5067 (73.5); 2.5023 (96.2); 2.4978 (68.4); 2.3336 (0.4); 2.3290 (0.5); 2.3246 (0.4); 1.0785 (3.3); 1.0596 (7.5); 1.0406 (3.2); -0.0002 (1.5) 1-035: 1H-NMR(400.0 MHz, de-DMSO): δ = 8.7790 (0.3); 8.6436 (10.8); 8.6231 (0.4); 7.2775 (1.0); 7.2578 (2.4); 7.2384 (1.6); 7.1797 (1.6); 7.1578 (1.0); 7.0302 (1.4); 7.0264 (2.9); 7.0221 (3.7); 7.0029 (1.2); 7,0004 (1.3); 3.9030 (2.7); 3.8392 (0.7); 3.8282 (16.0); 3.3296 (143.7); 2.7403 (0.9); 2.7214 (2.9); 2.7024 (3.0); 2.6833 (1.0); 2.6761 (0.5); 2.6713 (0.6); 2.6669 (0.4); 2.5245 (1.4); 2.5108 (36.5); 2.5067 (73.5); 2.5023 (96.2); 2.4978 (68.4); 2.3336 (0.4); 2.3290 (0.5); 2.3246 (0.4); 1.0785 (3.3); 1.0596 (7.5); 1.0406 (3.2); -0.0002 (1.5) 1-035: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5613 (6.3); 8.5493 (6.4); 7.2683 (1.1); 7.2543 (1.8); 7.2485 (2.9); 7.2425 (3.3); 7.2297 (3.0); 7.1649 (1.5); 7.1625 (1.5); 7.1425 (1.0); 7.0590 (1.6); 7.0544 (3.1); 7.0497 (1.9); 7.0342 (1.6); 7.0144 (1.3); 3.9032 (2.3); 3.8317 (16.0); 3.3290 (131.3); 2.7323 (0.9); 2.7135 (2.9); 2.6944 (3.0); 2.6756 (1.3); 2.5241 (1.3); 2.5065 (67.6); 2.5022 (87.2); 2.4978 (62.1); 2.3290 (0.5);δ = 8.5613 (6.3); 8.5493 (6.4); 7.2683 (1.1); 7.2543 (1.8); 7.2485 (2.9); 7.2425 (3.3); 7.2297 (3.0); 7.1649 (1.5); 7.1625 (1.5); 7.1425 (1.0); 7.0590 (1.6); 7.0544 (3.1); 7.0497 (1.9); 7.0342 (1.6); 7.0144 (1.3); 3.9032 (2.3); 3.8317 (16.0); 3.3290 (131.3); 2.7323 (0.9); 2.7135 (2.9); 2.6944 (3.0); 2.6756 (1.3); 2.5241 (1.3); 2.5065 (67.6); 2.5022 (87.2); 2.4978 (62.1); 2.3290 (0.5);
2.3247 (0.4); 1.0715 (3.3); 1.0526 (7.2); 1.0336 (3.1); -0.0001 (1.6) 2.3247 (0.4); 1.0715 (3.3); 1.0526 (7.2); 1.0336 (3.1); -0.0001 (1.6)
1-036: 1H-NMR(400.0 MHz, de-DMSO): 1-036: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5495 (2.2); 8.5425 (7.0); 8.5306 (6.5); 7.3437 (0.7); 7.3225 (1.5); 7.3172 (0.8); 7.3011 (1.2); 7.2959 (1.4); 7.2743 (0.7); 7.2593 (0.6); 7.2523 (2.0); 7.2474 (1.2); 7.2404 (3.4); 7.2284 (1.6); 7.0947 (0.9); 7.0888 (0.8); 7.0759 (1.1); 7.0698 (1.2); 7.0607 (0.9); 7.0479 (0.9); 7.0422 (0.7); 6.8734 (1.1); 6.8675 (1.2); 6.8629 (1.0); 6.8570 (1.0); 6.8516 (1.0); 6.8454 (1.0); 3.9102 (0.4); 3.9033 (1.1); 3.7909 (5.7); 3.7840 (16.0); 3.3317 (26.2); 3.3249 (72.6); 3.1753 (0.4); 3.1623 (0.4); 2.6756 (0.5); 2.6712 (0.5);δ = 8.5495 (2.2); 8.5425 (7.0); 8.5306 (6.5); 7.3437 (0.7); 7.3225 (1.5); 7.3172 (0.8); 7.3011 (1.2); 7.2959 (1.4); 7.2743 (0.7); 7.2593 (0.6); 7.2523 (2.0); 7.2474 (1.2); 7.2404 (3.4); 7.2284 (1.6); 7.0947 (0.9); 7.0888 (0.8); 7.0759 (1.1); 7.0698 (1.2); 7.0607 (0.9); 7.0479 (0.9); 7.0422 (0.7); 6.8734 (1.1); 6.8675 (1.2); 6.8629 (1.0); 6.8570 (1.0); 6.8516 (1.0); 6.8454 (1.0); 3.9102 (0.4); 3.9033 (1.1); 3.7909 (5.7); 3.7840 (16.0); 3.3317 (26.2); 3.3249 (72.6); 3.1753 (0.4); 3.1623 (0.4); 2.6756 (0.5); 2.6712 (0.5);
2.5066 (89.6); 2.5023 (95.2); 2.4980 (62.5); 2.3294 (0.6); 2.2839 (5.7); 2.2770 (15.7); 0.0070 (0.6); -0.0002 (1.9) 2.5066 (89.6); 2.5023 (95.2); 2.4980 (62.5); 2.3294 (0.6); 2.2839 (5.7); 2.2770 (15.7); 0.0070 (0.6); -0.0002 (1.9)
1-037: 1H-NMR(400.0 MHz, de-DMSO): 1-037: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6609 (10.8); 7.3618 (0.6); 7.3404 (1.2); 7.3355 (0.7); 7.3188 (0.7); 7.3139 (1.2); 7.2924 (0.6); 7.1158 (0.6); 7.1100 (0.7); 7.0973 (0.6); 7.0914 (0.8); 7.0882 (0.8); 7.0823 (0.7); 7.0696 (0.6); 7.0637 (0.6); 6.8874 (0.4); 6.8835 (0.6); 6.8777 (0.8); 6.8735 (0.6); 6.8673 (0.6); 6.8615 (0.6); 6.8560 (0.7); 6.8516 (0.6); 3.9033 (1.0); 3.8159 (16.0); 3.3245 (68.2); 2.7376 (0.8); 2.7186 (2.8); 2.6995 (2.9); 2.6805 (1.0); 2.6712 (0.5); 2.6667 (0.4); 2.5244 (1.1); 2.5110 (29.9); 2.5066 (61.8); 2.5021 (81.7); 2.4976δ = 8.6609 (10.8); 7.3618 (0.6); 7.3404 (1.2); 7.3355 (0.7); 7.3188 (0.7); 7.3139 (1.2); 7.2924 (0.6); 7.1158 (0.6); 7.1100 (0.7); 7.0973 (0.6); 7.0914 (0.8); 7.0882 (0.8); 7.0823 (0.7); 7.0696 (0.6); 7.0637 (0.6); 6.8874 (0.4); 6.8835 (0.6); 6.8777 (0.8); 6.8735 (0.6); 6.8673 (0.6); 6.8615 (0.6); 6.8560 (0.7); 6.8516 (0.6); 3.9033 (1.0); 3.8159 (16.0); 3.3245 (68.2); 2.7376 (0.8); 2.7186 (2.8); 2.6995 (2.9); 2.6805 (1.0); 2.6712 (0.5); 2.6667 (0.4); 2.5244 (1.1); 2.5110 (29.9); 2.5066 (61.8); 2.5021 (81.7); 2.4976
(57.9); 2.4933 (27.4); 2.3331 (0.3); 2.3287 (0.4); 2.3244 (0.3); 1.0794 (3.2); 1.0605 (7.3); 1.0415 (3.0); -0.0002 (1.2) (57.9); 2.4933 (27.4); 2.3331 (0.3); 2.3287 (0.4); 2.3244 (0.3); 1.0794 (3.2); 1.0605 (7.3); 1.0415 (3.0); -0.0002 (1.2)
1-038: 1H-NMR(400.0 MHz, de-DMSO): 1-038: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5467 (11.9); 8.5347 (12.1); 8.1653 (10.4); 7.2528 (3.1); 7.2408 (6.0); 7.2289 (3.0); 7.1287 (0.4); 7.1141 (1.2); 7.1055 (11.3); 7.1037 (11.1); 7.0912 (6.8); 7.0870 (3.2); 7.0828 (7.0); 7.0754 (0.8); 7.0671 (0.5); 7.0598 (0.8); 4.1446 (1.9); 4.1264 (6.1); 4.1083 (6.2); 4.0901 (2.0); 3.9031 (1.6); 3.3268 (159.2); 2.6753 (0.5); 2.6711 (0.7); 2.6665 (0.5); 2.5243 (1.7); 2.5108 (45.1); 2.5064 (93.1); 2.5019 (122.7); 2.4974 (86.3); 2.4929 (40.2); 2.3331 (0.5); 2.3286 (0.7); 2.3240 (0.5); 1.4210 (7.3); 1.4028 (16.0);δ = 8.5467 (11.9); 8.5347 (12.1); 8.1653 (10.4); 7.2528 (3.1); 7.2408 (6.0); 7.2289 (3.0); 7.1287 (0.4); 7.1141 (1.2); 7.1055 (11.3); 7.1037 (11.1); 7.0912 (6.8); 7.0870 (3.2); 7.0828 (7.0); 7.0754 (0.8); 7.0671 (0.5); 7.0598 (0.8); 4.1446 (1.9); 4.1264 (6.1); 4.1083 (6.2); 4.0901 (2.0); 3.9031 (1.6); 3.3268 (159.2); 2.6753 (0.5); 2.6711 (0.7); 2.6665 (0.5); 2.5243 (1.7); 2.5108 (45.1); 2.5064 (93.1); 2.5019 (122.7); 2.4974 (86.3); 2.4929 (40.2); 2.3331 (0.5); 2.3286 (0.7); 2.3240 (0.5); 1.4210 (7.3); 1.4028 (16.0);
1.3847 (7.1); -0.0002 (1.0) 1.3847 (7.1); -0.0002 (1.0)
1-039: 1H-NMR(400.0 MHz, de-DMSO): 1-039: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5467 (6.6); 8.5347 (6.8); 8.1978 (6.2); 7.2502 (1.7); 7.2382 (3.3); 7.2263 (1.7); 7.1023 (12.6); 7.0848 (7.5); 4.4916 (0.4); 4.4750 (1.0); 4.4584 (1.4); 4.4419 (1.0); 4.4253 (0.4); 3.9030 (0.8); 3.3252 (70.8); 2.6708 (0.4); 2.5241 (1.0); 2.5107 (27.6);δ = 8.5467 (6.6); 8.5347 (6.8); 8.1978 (6.2); 7.2502 (1.7); 7.2382 (3.3); 7.2263 (1.7); 7.1023 (12.6); 7.0848 (7.5); 4.4916 (0.4); 4.4750 (1.0); 4.4584 (1.4); 4.4419 (1.0); 4.4253 (0.4); 3.9030 (0.8); 3.3252 (70.8); 2.6708 (0.4); 2.5241 (1.0); 2.5107 (27.6);
2.5063 (57.3); 2.5018 (75.8); 2.4973 (53.6); 2.4928 (25.3); 2.3286 (0.4); 1.4474 (16.0); 1.4308 (15.8); -0.0002 (1.3) 2.5063 (57.3); 2.5018 (75.8); 2.4973 (53.6); 2.4928 (25.3); 2.3286 (0.4); 1.4474 (16.0); 1.4308 (15.8); -0.0002 (1.3)
1-040: 1H-NMR(400.0 MHz, de-DMSO): 1-040: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6398 (13.0); 8.2403 (5.8); 7.3084 (4.0); 7.2869 (4.9); 7.0675 (0.6); 7.0607 (4.9); 7.0559 (1.6); 7.0392 (4.2); 7.0322 (0.5); 4.5056 (0.4); 4.4890 (1.0); 4.4724 (1.4); 4.4557 (1.1); 4.4393 (0.4); 3.9031 (0.9); 3.3230 (45.1); 2.6749 (0.4); 2.6707 (0.5); 2.5061 (73.6); 2.5018 (94.5); 2.4974 (68.4); 2.3329 (0.4); 2.3286 (0.5); 2.3238 (0.4); 1.4516 (16.0); 1.4350 (15.8); -0.0002 (1.5) 1-041 : 1H-NMR(400.0 MHz, de-DMSO): δ = 8.6398 (13.0); 8.2403 (5.8); 7.3084 (4.0); 7.2869 (4.9); 7.0675 (0.6); 7.0607 (4.9); 7.0559 (1.6); 7.0392 (4.2); 7.0322 (0.5); 4.5056 (0.4); 4.4890 (1.0); 4.4724 (1.4); 4.4557 (1.1); 4.4393 (0.4); 3.9031 (0.9); 3.3230 (45.1); 2.6749 (0.4); 2.6707 (0.5); 2.5061 (73.6); 2.5018 (94.5); 2.4974 (68.4); 2.3329 (0.4); 2.3286 (0.5); 2.3238 (0.4); 1.4516 (16.0); 1.4350 (15.8); -0.0002 (1.5) 1-041: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5516 (11.1); 8.5397 (11.4); 8.1831 (10.3); 7.3052 (7.5); 7.3007 (2.6); 7.2884 (2.8); 7.2838 (9.2); 7.2769 (1.2); 7.2571 (2.9); 7.2452 (5.5); 7.2332 (2.8); 7.0869 (1.1); 7.0800 (9.3); 7.0753 (2.9); 7.0631 (2.5); 7.0585 (7.7); 7.0513 (0.8); 4.1563 (2.1); 4.1382δ = 8.5516 (11.1); 8.5397 (11.4); 8.1831 (10.3); 7.3052 (7.5); 7.3007 (2.6); 7.2884 (2.8); 7.2838 (9.2); 7.2769 (1.2); 7.2571 (2.9); 7.2452 (5.5); 7.2332 (2.8); 7.0869 (1.1); 7.0800 (9.3); 7.0753 (2.9); 7.0631 (2.5); 7.0585 (7.7); 7.0513 (0.8); 4.1563 (2.1); 4.1382
(6.5) ; 4.1200 (6.7); 4.1019 (2.2); 3.9032 (1.5); 3.3233 (69.8); 2.6748 (0.6); 2.6708 (0.9); 2.5061 (122.1); 2.5018 (159.6); 2.4975(6.5); 4.1200 (6.7); 4.1019 (2.2); 3.9032 (1.5); 3.3233 (69.8); 2.6748 (0.6); 2.6708 (0.9); 2.5061 (122.1); 2.5018 (159.6); 2.4975
(116.0); 2.3325 (0.7); 2.3285 (0.9); 2.3241 (0.7); 1.4273 (7.6); 1.4091 (16.0); 1.3910 (7.4); 1.2349 (0.3); -0.0001 (2.5) (116.0); 2.3325 (0.7); 2.3285 (0.9); 2.3241 (0.7); 1.4273 (7.6); 1.4091 (16.0); 1.3910 (7.4); 1.2349 (0.3); -0.0001 (2.5)
1-042: 1H-NMR(400.0 MHz, de-DMSO): 1-042: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5492 (11.0); 8.5372 (11.4); 8.1576 (10.0); 7.2480 (4.8); 7.2356 (6.8); 7.2306 (6.6); 7.2240 (3.7); 7.2111 (4.6); 7.1268 (2.2); 7.1083 (3.3); 7.0900 (1.3); 7.0680 (5.2); 7.0650 (6.4); 7.0469 (5.1); 4.1550 (2.0); 4.1369 (6.5); 4.1188 (6.6); 4.1006 (2.2); 3.9030δ = 8.5492 (11.0); 8.5372 (11.4); 8.1576 (10.0); 7.2480 (4.8); 7.2356 (6.8); 7.2306 (6.6); 7.2240 (3.7); 7.2111 (4.6); 7.1268 (2.2); 7.1083 (3.3); 7.0900 (1.3); 7.0680 (5.2); 7.0650 (6.4); 7.0469 (5.1); 4.1550 (2.0); 4.1369 (6.5); 4.1188 (6.6); 4.1006 (2.2); 3.9030
(1.6) ; 3.3278 (167.9); 2.6709 (0.8); 2.6665 (0.6); 2.5237 (1.9); 2.5061 (108.9); 2.5017 (144.3); 2.4973 (104.4); 2.3328 (0.6); 2.3283 (0.8); 2.3243 (0.6); 1.4283 (7.5); 1.4101 (16.0); 1.3920 (7.3); 1.2341 (0.4); -0.0002 (1.9) 1-043: 'H-NMR^O.O MHz, de-DMSO): (1.6); 3.3278 (167.9); 2.6709 (0.8); 2.6665 (0.6); 2.5237 (1.9); 2.5061 (108.9); 2.5017 (144.3); 2.4973 (104.4); 2.3328 (0.6); 2.3283 (0.8); 2.3243 (0.6); 1.4283 (7.5); 1.4101 (16.0); 1.3920 (7.3); 1.2341 (0.4); -0.0002 (1.9) 1-043: 'H NMR ^ OO MHz, de-DMSO):
δ= 8.6259 (10.5); 8.2111 (5.6); 7.1021 (10.7); 7.0845 (11.8); 4.4901 (0.4); 4.4737 (1.0); 4.4570 (1.4); 4.4405 (1.0); 4.4239 (0.4); 3.9031 (0.8); 3.3270 (67.1); 2.6710 (0.4); 2.5241 (1.1); 2.5107 (28.6); 2.5064 (58.5); 2.5020 (77.3); 2.4975 (55.1); 2.4932 (26.3);δ = 8.6259 (10.5); 8.2111 (5.6); 7.1021 (10.7); 7.0845 (11.8); 4.4901 (0.4); 4.4737 (1.0); 4.4570 (1.4); 4.4405 (1.0); 4.4239 (0.4); 3.9031 (0.8); 3.3270 (67.1); 2.6710 (0.4); 2.5241 (1.1); 2.5107 (28.6); 2.5064 (58.5); 2.5020 (77.3); 2.4975 (55.1); 2.4932 (26.3);
2.3286 (0.4); 1.4436 (16.0); 1.4270 (15.8); -0.0002 (1.2) 2.3286 (0.4); 1.4436 (16.0); 1.4270 (15.8); -0.0002 (1.2)
1-044: Ή-ΝΜϋ^ΟΟ.Ο MHz, CDC13):  1-044: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, CDC13):
δ= 8.4791 (4.4); 8.4672 (4.4); 7.2620 (29.1); 7.0803 (0.6); 7.0647 (0.7); 7.0589 (1.1); 7.0433 (1.1); 7.0385 (0.6); 7.0367 (0.5); 7.0210 (0.6); 7.0171 (1.8); 7.0051 (3.3); 6.9931 (1.7); 6.7384 (0.6); 6.7320 (0.8); 6.7166 (0.7); 6.7144 (0.5); 6.7097 (1.7); 6.7078 (1.6); 6.6872 (2.0); 6.6802 (0.7); 6.6779 (0.5); 6.6669 (0.6); 6.6642 (0.5); 3.8131 (16.0); 3.7879 (1.3); 2.9554 (3.2); 2.8837 (2.8);δ = 8.4791 (4.4); 8.4672 (4.4); 7.2620 (29.1); 7.0803 (0.6); 7.0647 (0.7); 7.0589 (1.1); 7.0433 (1.1); 7.0385 (0.6); 7.0367 (0.5); 7.0210 (0.6); 7.0171 (1.8); 7.0051 (3.3); 6.9931 (1.7); 6.7384 (0.6); 6.7320 (0.8); 6.7166 (0.7); 6.7144 (0.5); 6.7097 (1.7); 6.7078 (1.6); 6.6872 (2.0); 6.6802 (0.7); 6.6779 (0.5); 6.6669 (0.6); 6.6642 (0.5); 3.8131 (16.0); 3.7879 (1.3); 2.9554 (3.2); 2.8837 (2.8);
2.8824 (2.7); 2.3430 (13.4); 2.2935 (1.1); 1.5777 (1.1); -0.0002 (9.9) 2.8824 (2.7); 2.3430 (13.4); 2.2935 (1.1); 1.5777 (1.1); -0.0002 (9.9)
1-045: 1H-NMR(400.1 MHz, de-DMSO): 1-045: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.5522 (6.2); 8.5403 (6.3); 7.2614 (1.7); 7.2495 (3.2); 7.2375 (1.6); 6.9957 (0.4); 6.9904 (0.8); 6.9850 (0.5); 6.9727 (0.8); 6.9673 (1.5); 6.9619 (0.9); 6.9496 (0.5); 6.9441 (0.8); 6.9387 (0.4); 6.7559 (0.4); 6.7393 (2.5); 6.7239 (2.5); 6.7193 (2.0); 6.7070δ = 8.5522 (6.2); 8.5403 (6.3); 7.2614 (1.7); 7.2495 (3.2); 7.2375 (1.6); 6.9957 (0.4); 6.9904 (0.8); 6.9850 (0.5); 6.9727 (0.8); 6.9673 (1.5); 6.9619 (0.9); 6.9496 (0.5); 6.9441 (0.8); 6.9387 (0.4); 6.7559 (0.4); 6.7393 (2.5); 6.7239 (2.5); 6.7193 (2.0); 6.7070
(0.4); 3.9756 (0.3); 3.8019 (16.0); 2.5019 (13.6); 2.2743 (15.7); -0.0010 (2.4) (0.4); 3.9756 (0.3); 3.8019 (16.0); 2.5019 (13.6); 2.2743 (15.7); -0.0010 (2.4)
1-046: 1H-NMR(400.1 MHz, de-DMSO): 1-046: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.5854 (4.1); 8.5745 (6.6); 8.5639 (4.2); 7.2802 (1.1); 7.2682 (2.1); 7.2563 (1.1); 7.2374 (1.1); 7.2253 (2.1); 7.2132 (1.0);δ = 8.5854 (4.1); 8.5745 (6.6); 8.5639 (4.2); 7.2802 (1.1); 7.2682 (2.1); 7.2563 (1.1); 7.2374 (1.1); 7.2253 (2.1); 7.2132 (1.0);
3.7911 (10.6); 3.6170 (16.0); 2.5099 (20.0); 2.2592 (10.3); 1.2423 (1.2) 3.7911 (10.6); 3.6170 (16.0); 2.5099 (20.0); 2.2592 (10.3); 1.2423 (1.2)
1-047: 1H-NMR(400.1 MHz, de-DMSO): 1-047: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 11.2495 (3.0); 7.2917 (0.8); 7.2853 (0.9); 7.2674 (1.4); 7.2615 (1.4); 7.2437 (0.8); 7.2373 (0.8); 7.1535 (0.7); 7.1373 (0.8); 7.1315 (1.5); 7.1156 (1.5); 7.1098 (1.0); 7.0937 (0.8); 7.0006 (0.9); 6.9949 (0.8); 6.9792 (1.4); 6.9735 (1.4); 6.9579 (0.6); 6.9518δ = 11.2495 (3.0); 7.2917 (0.8); 7.2853 (0.9); 7.2674 (1.4); 7.2615 (1.4); 7.2437 (0.8); 7.2373 (0.8); 7.1535 (0.7); 7.1373 (0.8); 7.1315 (1.5); 7.1156 (1.5); 7.1098 (1.0); 7.0937 (0.8); 7,0006 (0.9); 6.9949 (0.8); 6.9792 (1.4); 6.9735 (1.4); 6.9579 (0.6); 6.9518
(0.6); 3.7716 (16.0); 2.5058 (15.9); 2.3047 (15.2); 1.2332 (1.4); -0.0012 (2.1) (0.6); 3.7716 (16.0); 2.5058 (15.9); 2.3047 (15.2); 1.2332 (1.4); -0.0012 (2.1)
1-048: 1H-NMR(400.1 MHz, de-DMSO): 1-048: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.2040 (2.6); 8.1912 (2.6); 7.5036 (2.1); 7.4909 (2.0); 7.2987 (3.9); 7.0775 (0.7); 7.0706 (0.5); 7.0547 (4.5); 7.0471 (4.6);δ = 8.2040 (2.6); 8.1912 (2.6); 7.5036 (2.1); 7.4909 (2.0); 7.2987 (3.9); 7.0775 (0.7); 7.0706 (0.5); 7.0547 (4.5); 7.0471 (4.6);
7.0332 (8.6); 3.8728 (16.0); 3.7731 (15.2); 2.5017 (19.0); 2.2902 (14.8); -0.0011 (2.9) 7.0332 (8.6); 3.8728 (16.0); 3.7731 (15.2); 2.5017 (19.0); 2.2902 (14.8); -0.0011 (2.9)
1-049: 1H-NMR(400.0 MHz, CDC13): 1-049: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.6013 (0.7); 8.5893 (0.7); 8.4459 (5.2); 8.4339 (5.3); 7.2605 (23.7); 7.1881 (0.9); 7.1836 (1.4); 7.1779 (0.6); 7.1690 (1.4); 7.1664 (3.1); 7.1628 (2.6); 7.1573 (1.8); 7.1546 (2.1); 7.1492 (0.6); 7.1424 (0.8); 7.1394 (1.8); 7.1373 (2.8); 7.1328 (1.0); 7.1223 (0.8); 7.1184 (1.2); 7.0984 (0.9); 7.0942 (1.4); 7.0895 (0.7); 7.0837 (0.6); 7.0785 (0.9); 7.0766 (1.0); 6.9990 (1.6); 6.9871 (3.0); 6.9751 (1.5); 4.2019 (1.7); 4.1821 (15.9); 4.1596 (1.2); 3.9473 (1.7); 3.8882 (1.0); 3.8105 (16.0); 1.5506 (1.7); -0.0002 (8.9) 1-050: 1H-NMR(400.0 MHz, CDC13): δ = 8.6013 (0.7); 8,5893 (0.7); 8.4459 (5.2); 8.4339 (5.3); 7.2605 (23.7); 7.1881 (0.9); 7.1836 (1.4); 7.1779 (0.6); 7.1690 (1.4); 7.1664 (3.1); 7.1628 (2.6); 7.1573 (1.8); 7.1546 (2.1); 7.1492 (0.6); 7.1424 (0.8); 7.1394 (1.8); 7.1373 (2.8); 7.1328 (1.0); 7.1223 (0.8); 7.1184 (1.2); 7.0984 (0.9); 7.0942 (1.4); 7.0895 (0.7); 7.0837 (0.6); 7.0785 (0.9); 7.0766 (1.0); 6.9990 (1.6); 6.9871 (3.0); 6.9751 (1.5); 4.2019 (1.7); 4.1821 (15.9); 4.1596 (1.2); 3.9473 (1.7); 3.8882 (1.0); 3.8105 (16.0); 1.5506 (1.7); -0.0002 (8.9) 1-050: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4834 (5.2); 8.4714 (5.3); 7.2608 (22.8); 7.0491 (1.6); 7.0461 (0.7); 7.0371 (2.9); 7.0336 (0.6); 7.0252 (1.8); 6.9629 (0.9); 6.9487 (1.6); 6.9449 (1.4); 6.9379 (0.9); 6.9325 (1.2); 6.9282 (1.3); 4.1879 (16.0); 4.1350 (0.5); 3.9048 (0.5); 3.8617 (16.0);δ = 8.4834 (5.2); 8.4714 (5.3); 7.2608 (22.8); 7.0491 (1.6); 7.0461 (0.7); 7.0371 (2.9); 7.0336 (0.6); 7.0252 (1.8); 6.9629 (0.9); 6.9487 (1.6); 6.9449 (1.4); 6.9379 (0.9); 6.9325 (1.2); 6.9282 (1.3); 4.1879 (16.0); 4.1350 (0.5); 3.9048 (0.5); 3.8617 (16.0);
1.5457 (3.4); -0.0002 (8.6) 1.5457 (3.4); -0.0002 (8.6)
1-051 : 1H-NMR(400.0 MHz, CDC13): 1-051: 1 H-NMR (400.0 MHz, CDC13):
δ= 7.2593 (50.1); 7.2069 (1.0); 7.2048 (1.4); 7.2006 (0.6); 7.1942 (0.6); 7.1858 (2.4); 7.1838 (3.0); 7.1810 (1.6); 7.1781 (2.0); 7.1731 (1.7); 7.1676 (4.0); 7.1043 (4.6); 7.1026 (4.7); 7.0982 (1.3); 7.0875 (2.6); 7.0846 (3.6); 7.0828 (3.0); 7.0687 (0.6); 7.0655 (0.8); 6.8002 (2.1); 6.7908 (2.0); 3.8079 (16.0); 2.2935 (13.9); 2.0433 (0.6); 1.5420 (9.1); 1.2585 (0.6); 0.8819 (0.7); 0.0079δ = 7.2593 (50.1); 7.2069 (1.0); 7.2048 (1.4); 7.2006 (0.6); 7.1942 (0.6); 7.1858 (2.4); 7.1838 (3.0); 7.1810 (1.6); 7.1781 (2.0); 7.1731 (1.7); 7.1676 (4.0); 7.1043 (4.6); 7.1026 (4.7); 7.0982 (1.3); 7.0875 (2.6); 7.0846 (3.6); 7.0828 (3.0); 7.0687 (0.6); 7.0655 (0.8); 6.8002 (2.1); 6.7908 (2.0); 3.8079 (16.0); 2.2935 (13.9); 2.0433 (0.6); 1.5420 (9.1); 1.2585 (0.6); 0.8819 (0.7); 0.0079
(0.7); -0.0002 (18.0); -0.0085 (0.8) (0.7); -0.0002 (18.0); -0.0085 (0.8)
1-052: 1H-NMR(400.0 MHz, CDC13): 1-052: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.6145 (0.6); 8.6026 (0.7); 8.5019 (5.2); 8.4899 (5.4); 8.2274 (1.9); 8.2207 (2.0); 7.2634 (14.5); 7.2348 (0.7); 7.2274 (0.7); 7.2130 (1.3); 7.2057 (1.3); 7.1925 (0.9); 7.1852 (0.8); 7.0346 (1.6); 7.0226 (3.0); 7.0107 (1.6); 6.9977 (1.4); 6.9874 (1.4); 6.9755δ = 8.6145 (0.6); 8.6026 (0.7); 8.5019 (5.2); 8.4899 (5.4); 8.2274 (1.9); 8.2207 (2.0); 7.2634 (14.5); 7.2348 (0.7); 7.2274 (0.7); 7.2130 (1.3); 7.2057 (1.3); 7.1925 (0.9); 7.1852 (0.8); 7.0346 (1.6); 7.0226 (3.0); 7.0107 (1.6); 6.9977 (1.4); 6.9874 (1.4); 6.9755
(1.1); 6.9653 (1.1); 5.2988 (2.5); 3.8651 (16.0); 3.8394 (2.2); 2.3293 (2.6); 2.3215 (15.9); 1.5884 (1.0); -0.0002 (5.2) (1.1); 6.9653 (1.1); 5.2988 (2.5); 3.8651 (16.0); 3.8394 (2.2); 2.3293 (2.6); 2.3215 (15.9); 1.5884 (1.0); -0.0002 (5.2)
1-053: 1H-NMR(400.0 MHz, CDC13): 1-053: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4263 (2.3); 8.4143 (2.4); 7.2615 (5.5); 7.1701 (0.8); 7.1667 (0.5); 7.1513 (0.9); 7.1492 (0.6); 7.0913 (0.6); 7.0873 (1.2); 7.0836 (1.2); 7.0663 (0.8); 7.0632 (0.5); 6.9930 (0.6); 6.9811 (1.3); 6.9691 (0.6); 5.2976 (1.4); 2.6258 (6.3); 1.6537 (16.0);δ = 8.4263 (2.3); 8.4143 (2.4); 7.2615 (5.5); 7.1701 (0.8); 7.1667 (0.5); 7.1513 (0.9); 7.1492 (0.6); 7.0913 (0.6); 7.0873 (1.2); 7.0836 (1.2); 7.0663 (0.8); 7.0632 (0.5); 6.9930 (0.6); 6.9811 (1.3); 6.9691 (0.6); 5.2976 (1.4); 2.6258 (6.3); 1.6537 (16.0);
1.5730 (0.7); -0.0002 (2.5) 1.5730 (0.7); -0.0002 (2.5)
1-054: 'H-NMR(601.6 MHz, CD3CN):  1-054: 'H-NMR (601.6 MHz, CD3CN):
δ= 8.4096 (0.5); 8.4016 (0.5); 8.3814 (5.4); 8.3734 (5.4); 7.8590 (1.7); 7.7525 (1.0); 7.7379 (0.9); 7.3919 (1.3); 7.3778 (1.1); 7.0824 (0.4); 7.0793 (1.6); 7.0714 (3.1); 7.0634 (1.5); 3.8437 (16.0); 3.8369 (1.7); 2.5350 (0.7); 2.3033 (15.7); 2.3000 (2.2); 2.2428 (0.4); 2.2304 (0.4); 2.1907 (14.6); 2.1459 (0.4); 1.9925 (2.6); 1.9844 (1.3); 1.9802 (1.5); 1.9764 (5.9); 1.9723 (9.5);δ = 8.4096 (0.5); 8.4016 (0.5); 8.3814 (5.4); 8.3734 (5.4); 7.8590 (1.7); 7.7525 (1.0); 7.7379 (0.9); 7.3919 (1.3); 7.3778 (1.1); 7.0824 (0.4); 7.0793 (1.6); 7.0714 (3.1); 7.0634 (1.5); 3.8437 (16.0); 3.8369 (1.7); 2.5350 (0.7); 2.3033 (15.7); 2.3000 (2.2); 2.2428 (0.4); 2.2304 (0.4); 2.1907 (14.6); 2.1459 (0.4); 1.9925 (2.6); 1.9844 (1.3); 1.9802 (1.5); 1.9764 (5.9); 1.9723 (9.5);
1.9682 (13.6); 1.9641 (9.3); 1.9600 (4.7) 1.9682 (13.6); 1.9641 (9.3); 1.9600 (4.7)
1-058: 1H-NMR(400.0 MHz, CDC13): 1-058: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4615 (5.6); 8.4495 (5.8); 7.2648 (9.5); 7.1222 (2.5); 7.1169 (1.0); 7.1057 (1.2); 7.1002 (4.4); 7.0940 (0.6); 7.0522 (0.7); 7.0461 (4.6); 7.0405 (1.2); 7.0293 (0.9); 7.0240 (2.5); 6.9940 (1.6); 6.9820 (3.1); 6.9700 (1.6); 3.8549 (16.0); 2.7521 (0.8);δ = 8.4615 (5.6); 8.4495 (5.8); 7.2648 (9.5); 7.1222 (2.5); 7.1169 (1.0); 7.1057 (1.2); 7.1002 (4.4); 7.0940 (0.6); 7.0522 (0.7); 7.0461 (4.6); 7.0405 (1.2); 7.0293 (0.9); 7.0240 (2.5); 6.9940 (1.6); 6.9820 (3.1); 6.9700 (1.6); 3.8549 (16.0); 2.7521 (0.8);
2.7330 (2.8); 2.7139 (2.8); 2.6949 (0.9); 2.1684 (2.6); 1.1401 (3.0); 1.1211 (6.7); 1.1020 (2.9); -0.0002 (3.6) 2.7330 (2.8); 2.7139 (2.8); 2.6949 (0.9); 2.1684 (2.6); 1.1401 (3.0); 1.1211 (6.7); 1.1020 (2.9); -0.0002 (3.6)
1-059: 1H-NMR(400.0 MHz, CDC13): 1-059: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3768 (1.5); 8.3672 (13.2); 7.5844 (0.6); 7.5783 (4.0); 7.5735 (1.4); 7.5617 (1.6); 7.5563 (8.3); 7.3959 (0.7); 7.3899 (5.0); 7.3849 (1.6); 7.3732 (1.3); 7.3683 (4.0); 7.3622 (0.6); 7.2604 (68.4); 3.8899 (1.6); 3.8598 (16.0); 1.5546 (6.6); 1.3331 (1.4);δ = 8.3768 (1.5); 8.3672 (13.2); 7.5844 (0.6); 7,5783 (4.0); 7.5735 (1.4); 7.5617 (1.6); 7.5563 (8.3); 7.3959 (0.7); 7.3899 (5.0); 7.3849 (1.6); 7.3732 (1.3); 7.3683 (4.0); 7.3622 (0.6); 7.2604 (68.4); 3.8899 (1.6); 3.8598 (16.0); 1.5546 (6.6); 1.3331 (1.4);
1.2843 (1.9); 1.2555 (3.3); 0.8801 (0.6); 0.0080 (0.8); -0.0002 (25.4); -0.0084 (1.0) 1.2843 (1.9); 1.2555 (3.3); 0.8801 (0.6); 0.0080 (0.8); -0.0002 (25.4); -0.0084 (1.0)
1-060: 1H-NMR(400.0 MHz, CDC13): 1-060: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3685 (14.0); 7.2678 (0.6); 7.2670 (0.6); 7.2662 (0.7); 7.2654 (0.9); 7.2645 (1.2); 7.2605 (65.2); 7.2564 (0.7); 7.0798 (1.9); 7.0743 (0.7); 7.0671 (2.0); 7.0630 (0.8); 7.0616 (0.8); 7.0573 (2.4); 7.0501 (0.8); 7.0446 (2.4); 6.8984 (2.4); 6.8927 (0.7); 6.8815 (0.7); 6.8770 (3.3); 6.8761 (3.0); 6.8714 (0.7); 6.8601 (0.6); 6.8546 (1.9); 3.8188 (16.0); 2.3152 (15.5); 1.5434 (8.9); 1.1902δ = 8.3685 (14.0); 7.2678 (0.6); 7.2670 (0.6); 7.2662 (0.7); 7.2654 (0.9); 7.2645 (1.2); 7.2605 (65.2); 7.2564 (0.7); 7.0798 (1.9); 7.0743 (0.7); 7.0671 (2.0); 7.0630 (0.8); 7.0616 (0.8); 7.0573 (2.4); 7.0501 (0.8); 7.0446 (2.4); 6.8984 (2.4); 6.8927 (0.7); 6.8815 (0.7); 6.8770 (3.3); 6.8761 (3.0); 6.8714 (0.7); 6.8601 (0.6); 6.8546 (1.9); 3.8188 (16.0); 2.3152 (15.5); 1.5434 (8.9); 1.1902
(0.5); 0.0080 (0.8); -0.0002 (30.2); -0.0085 (0.8) (0.5); 0.0080 (0.8); -0.0002 (30.2); -0.0085 (0.8)
1-061 : 1H-NMR(400.0 MHz, de-DMSO): 1-061: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2727 (6.1); 7.2699 (0.5); 7.2503 (1.1); 7.2307 (0.8); 7.1683 (0.8); 7.1490 (0.5); 7.1464 (0.5); 7.0237 (1.5); 7.0197 (1.8); 7.0007 (0.6); 6.9985 (0.6); 3.9031 (0.4); 3.8155 (16.0); 3.3244 (32.3); 2.7285 (0.4); 2.7093 (1.4); 2.6904 (1.4); 2.6711 (0.6); 2.5061 (32.6); 2.5018 (42.0); 2.4974 (30.4); 1.0717 (1.6); 1.0529 (3.4); 1.0338 (1.5); -0.0002 (0.4) 1-062: 'H-NMR^O.O MHz, de-DMSO): δ = 8.2727 (6.1); 7.2699 (0.5); 7.2503 (1.1); 7.2307 (0.8); 7.1683 (0.8); 7.1490 (0.5); 7.1464 (0.5); 7.0237 (1.5); 7.0197 (1.8); 7,0007 (0.6); 6.9985 (0.6); 3.9031 (0.4); 3.8155 (16.0); 3.3244 (32.3); 2.7285 (0.4); 2.7093 (1.4); 2.6904 (1.4); 2.6711 (0.6); 2.5061 (32.6); 2.5018 (42.0); 2.4974 (30.4); 1.0717 (1.6); 1.0529 (3.4); 1.0338 (1.5); -0.0002 (0.4) 1-062: 'H NMR ^ OO MHz, de-DMSO):
δ= 8.5628 (6.2); 8.5508 (6.4); 7.3539 (0.6); 7.3325 (1.2); 7.3275 (0.7); 7.3110 (0.8); 7.3059 (1.2); 7.2844 (0.6); 7.2592 (1.6); 7.2473 (3.1); 7.2353 (1.6); 7.1248 (0.7); 7.1190 (0.7); 7.1062 (0.7); 7.1003 (0.8); 7.0969 (0.8); 7.0910 (0.7); 7.0781 (0.7); 7.0725 (0.7); 6.8985 (0.6); 6.8935 (0.8); 6.8891 (0.7); 6.8824 (0.6); 6.8774 (0.6); 6.8715 (0.7); 6.8665 (0.6); 3.9031 (1.8); 3.8195 (16.0); 3.3267 (96.9); 2.7331 (0.9); 2.7139 (2.9); 2.6949 (3.0); 2.6759 (1.3); 2.5243 (1.2); 2.5064 (63.3); 2.5021 (83.5); 2.4977 (60.2);δ = 8.5628 (6.2); 8.5508 (6.4); 7.3539 (0.6); 7.3325 (1.2); 7.3275 (0.7); 7.3110 (0.8); 7.3059 (1.2); 7.2844 (0.6); 7.2592 (1.6); 7.2473 (3.1); 7.2353 (1.6); 7.1248 (0.7); 7.1190 (0.7); 7.1062 (0.7); 7.1003 (0.8); 7.0969 (0.8); 7.0910 (0.7); 7.0.781 (0.7); 7.0725 (0.7); 6.8985 (0.6); 6.8935 (0.8); 6.8891 (0.7); 6.8824 (0.6); 6.8774 (0.6); 6.8715 (0.7); 6.8665 (0.6); 3.9031 (1.8); 3.8195 (16.0); 3.3267 (96.9); 2.7331 (0.9); 2.7139 (2.9); 2.6949 (3.0); 2.6759 (1.3); 2.5243 (1.2); 2.5064 (63.3); 2.5021 (83.5); 2.4977 (60.2);
2.3330 (0.3); 2.3290 (0.5); 1.0763 (3.2); 1.0574 (7.3); 1.0383 (3.1); -0.0002 (1.8) 2.3330 (0.3); 2.3290 (0.5); 1.0763 (3.2); 1.0574 (7.3); 1.0383 (3.1); -0.0002 (1.8)
1-063: Ή-ΝΜϋ^ΟΟ.Ο MHz, de-DMSO):  1-063: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, de-DMSO):
δ= 8.5581 (6.1); 8.5462 (6.2); 7.2413 (3.0); 7.2292 (3.4); 7.2225 (3.4); 7.2177 (2.4); 7.2031 (2.4); 7.1140 (1.1); 7.0956 (1.8); 7.0774 (0.6); 7.0472 (2.7); 7.0443 (3.3); 7.0260 (2.7); 3.9030 (1.3); 3.8127 (16.0); 3.3245 (55.9); 2.7237 (0.8); 2.7047 (2.9); 2.6856 (3.0); 2.6666 (1.2); 2.5240 (1.0); 2.5102 (26.6); 2.5061 (54.5); 2.5017 (72.1); 2.4972 (51.5); 2.4930 (24.7); 2.3284 (0.4);δ = 8.5581 (6.1); 8.5462 (6.2); 7.2413 (3.0); 7.2292 (3.4); 7.2225 (3.4); 7.2177 (2.4); 7.2031 (2.4); 7.1140 (1.1); 7.0956 (1.8); 7.0774 (0.6); 7.0472 (2.7); 7.0443 (3.3); 7.0260 (2.7); 3.9030 (1.3); 3.8127 (16.0); 3.3245 (55.9); 2.7237 (0.8); 2.7047 (2.9); 2.6856 (3.0); 2.6666 (1.2); 2.5240 (1.0); 2.5102 (26.6); 2.5061 (54.5); 2.5017 (72.1); 2.4972 (51.5); 2.4930 (24.7); 2.3284 (0.4);
1.0584 (3.2); 1.0395 (7.3); 1.0205 (3.1); -0.0002 (1.9) 1.0584 (3.2); 1.0395 (7.3); 1.0205 (3.1); -0.0002 (1.9)
1-064: 1H-NMR(400.0 MHz, de-DMSO): 1-064: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5594 (6.2); 8.5475 (6.3); 7.2486 (1.6); 7.2367 (3.1); 7.2248 (1.6); 7.0931 (12.1); 7.0756 (9.5); 3.9031 (1.8); 3.8028 (16.0); 3.3269 (84.2); 2.7317 (0.9); 2.7127 (2.9); 2.6937 (3.0); 2.6749 (1.3); 2.5063 (61.2); 2.5020 (78.5); 2.4976 (55.8); 2.3288 (0.4);δ = 8.5594 (6.2); 8.5475 (6.3); 7.2486 (1.6); 7.2367 (3.1); 7.2248 (1.6); 7.0931 (12.1); 7.0756 (9.5); 3.9031 (1.8); 3.8028 (16.0); 3.3269 (84.2); 2.7317 (0.9); 2.7127 (2.9); 2.6937 (3.0); 2.6749 (1.3); 2.5063 (61.2); 2.5020 (78.5); 2.4976 (55.8); 2.3288 (0.4);
1.0590 (3.3); 1.0401 (7.4); 1.0211 (3.2); -0.0002 (1.4) 1.0590 (3.3); 1.0401 (7.4); 1.0211 (3.2); -0.0002 (1.4)
1-065: 1H-NMR(400.0 MHz, de-DMSO): 1-065: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6280 (11.5); 7.4363 (1.4); 7.4295 (1.5); 7.4148 (1.5); 7.4080 (1.5); 7.1713 (0.7); 7.1645 (0.7); 7.1494 (1.4); 7.1428 (1.3); 7.1281 (0.9); 7.1213 (0.8); 6.8922 (1.6); 6.8776 (1.6); 6.8698 (1.4); 6.8553 (1.4); 3.9033 (1.0); 3.7932 (16.0); 3.3241 (62.4);δ = 8.6280 (11.5); 7.4363 (1.4); 7.4295 (1.5); 7.4148 (1.5); 7.4080 (1.5); 7.1713 (0.7); 7.1645 (0.7); 7.1494 (1.4); 7.1428 (1.3); 7.1281 (0.9); 7.1213 (0.8); 6.8922 (1.6); 6.8776 (1.6); 6.8698 (1.4); 6.8553 (1.4); 3.9033 (1.0); 3.7932 (16.0); 3.3241 (62.4);
2.6710 (0.5); 2.5240 (1.5); 2.5063 (71.0); 2.5020 (93.7); 2.4977 (68.8); 2.3286 (0.5); 2.2642 (15.8); -0.0002 (1.3) 2.6710 (0.5); 2.5240 (1.5); 2.5063 (71.0); 2.5020 (93.7); 2.4977 (68.8); 2.3286 (0.5); 2.2642 (15.8); -0.0002 (1.3)
1-066: 1H-NMR(400.0 MHz, de-DMSO): 1-066: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2478 (10.8); 7.2973 (0.4); 7.2907 (3.6); 7.2862 (1.2); 7.2692 (4.3); 7.2623 (0.5); 7.0256 (0.5); 7.0185 (4.3); 7.0138 (1.3); 7.0016 (1.2); 6.9971 (3.7); 6.9900 (0.4); 3.9035 (0.8); 3.8120 (16.0); 3.7656 (13.1); 3.3251 (40.8); 2.6707 (0.4); 2.5063 (56.4);δ = 8.2478 (10.8); 7.2973 (0.4); 7.2907 (3.6); 7.2862 (1.2); 7.2692 (4.3); 7.2623 (0.5); 7.0256 (0.5); 7.0185 (4.3); 7.0138 (1.3); 7.0016 (1.2); 6.9971 (3.7); 6.9900 (0.4); 3.9035 (0.8); 3.8120 (16.0); 3.7656 (13.1); 3.3251 (40.8); 2.6707 (0.4); 2.5063 (56.4);
2.5021 (73.2); 2.4979 (53.3); 2.3329 (0.3); 2.3285 (0.4); 2.2585 (13.0); 0.0001 (1.0) 2.5021 (73.2); 2.4979 (53.3); 2.3329 (0.3); 2.3285 (0.4); 2.2585 (13.0); 0.0001 (1.0)
1-067: 1H-NMR(400.0 MHz, de-DMSO): 1-067: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5487 (6.5); 8.5368 (6.7); 8.1029 (5.4); 7.2496 (2.6); 7.2380 (3.5); 7.2280 (4.0); 7.2266 (4.0); 7.2094 (2.7); 7.1276 (1.3); 7.1093 (1.9); 7.0908 (0.7); 7.0722 (3.1); 7.0692 (3.7); 7.0511 (3.0); 3.9029 (0.9); 3.8481 (16.0); 3.3281 (83.8); 2.6708 (0.4);δ = 8.5487 (6.5); 8.5368 (6.7); 8.1029 (5.4); 7.2496 (2.6); 7.2380 (3.5); 7.2280 (4.0); 7.2266 (4.0); 7.2094 (2.7); 7.1276 (1.3); 7.1093 (1.9); 7.0908 (0.7); 7.0722 (3.1); 7.0692 (3.7); 7.0511 (3.0); 3.9029 (0.9); 3.8481 (16.0); 3.3281 (83.8); 2.6708 (0.4);
2.5061 (53.5); 2.5018 (69.3); 2.4974 (49.8); 2.3287 (0.4); -0.0002 (0.9) 2.5061 (53.5); 2.5018 (69.3); 2.4974 (49.8); 2.3287 (0.4); -0.0002 (0.9)
1-069: 1H-NMR(400.0 MHz, CDC13): 1-069: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4705 (3.8); 8.4586 (3.9); 7.2620 (15.4); 7.0943 (0.7); 7.0747 (2.1); 7.0552 (1.8); 7.0473 (1.0); 7.0428 (2.4); 7.0388 (1.7); 7.0303 (1.3); 7.0270 (1.8); 7.0221 (1.0); 7.0107 (0.7); 7.0075 (0.7); 7.0058 (0.6); 6.9897 (1.6); 6.9777 (3.1); 6.9717 (1.3); 6.9659δ = 8.4705 (3.8); 8.4586 (3.9); 7.2620 (15.4); 7.0943 (0.7); 7.0747 (2.1); 7.0552 (1.8); 7.0473 (1.0); 7.0428 (2.4); 7.0388 (1.7); 7.0303 (1.3); 7.0270 (1.8); 7.0221 (1.0); 7.0107 (0.7); 7.0075 (0.7); 7.0058 (0.6); 6.9897 (1.6); 6.9777 (3.1); 6.9717 (1.3); 6.9659
(2.0) ; 6.9526 (0.8); 6.9493 (0.9); 6.9483 (0.9); 6.9450 (0.7); 3.8472 (16.0); 2.3036 (15.6); 1.5771 (2.4); -0.0002 (5.4) (2.0); 6.9526 (0.8); 6.9493 (0.9); 6.9483 (0.9); 6.9450 (0.7); 3.8472 (16.0); 2.3036 (15.6); 1.5771 (2.4); -0.0002 (5.4)
1-070: 1H-NMR(400.2 MHz, de-DMSO): 1-070: 1 H-NMR (400.2 MHz, de-DMSO):
δ= 8.4737 (4.7); 8.4713 (4.8); 8.4693 (4.4); 8.4633 (4.4); 8.4614 (4.9); 8.4590 (4.6); 8.0291 (5.4); 8.0083 (9.2); 7.9628 (4.1); 7.9581 (4.2); 7.9446 (4.7); 7.9401 (5.0); 7.9376 (3.1); 7.9238 (2.6); 7.9191 (2.6); 7.3011 (4.0); 7.2984 (4.1); 7.2887 (4.1); 7.2861 (4.6); 7.2830 (4.4); 7.2805 (4.0); 7.2707 (4.4); 7.2679 (4.6); 7.2642 (7.1); 7.2589 (3.3); 7.2511 (7.6); 7.2474 (4.8); 7.2456 (4.7); 7.2419 (10.3); 7.2343 (4.2); 7.2288 (9.5); 7.2210 (1.2); 7.1611 (1.4); 7.1533 (9.9); 7.1478 (3.1); 7.1362 (3.6); 7.1311 (16.0); 7.1257 (3.4); 7.1142 (2.8); 7.1089 (6.7); 7.1010 (0.7); 5.7570 (1.6); 4.0846 (7.0); 4.0674 (14.5); 4.0502 (7.2); 3.3218 (68.7); 2.9148 (5.7); 2.8970 (10.0); 2.8777 (6.6); 2.7047 (0.5); 2.6694 (0.4); 2.6645 (0.3); 2.5090 (25.5); 2.5047 (50.2); 2.5003 (66.2); 2.4958 (47.6); 2.4915 (22.5); 2.3965 (1.8); 2.3790 (5.5); 2.3608 (7.4); 2.3426 (4.9); 2.3250 (1.6); 2.0738 (3.1); 1.2331 (1.4);δ = 8.4737 (4.7); 8.4713 (4.8); 8.4693 (4.4); 8.4633 (4.4); 8.4614 (4.9); 8.4590 (4.6); 8.0291 (5.4); 8.0083 (9.2); 7.9628 (4.1); 7.9581 (4.2); 7.9446 (4.7); 7.9401 (5.0); 7.9376 (3.1); 7.9238 (2.6); 7.9191 (2.6); 7.3011 (4.0); 7.2984 (4.1); 7.2887 (4.1); 7.2861 (4.6); 7.2830 (4.4); 7.2805 (4.0); 7.2707 (4.4); 7.2679 (4.6); 7.2642 (7.1); 7.2589 (3.3); 7.2511 (7.6); 7.2474 (4.8); 7.2456 (4.7); 7.2419 (10.3); 7.2343 (4.2); 7.2288 (9.5); 7.2210 (1.2); 7.1611 (1.4); 7.1533 (9.9); 7.1478 (3.1); 7.1362 (3.6); 7.1311 (16.0); 7.1257 (3.4); 7.1142 (2.8); 7.1089 (6.7); 7.1010 (0.7); 5.7570 (1.6); 4.0846 (7.0); 4.0674 (14.5); 4.0502 (7.2); 3.3218 (68.7); 2.9148 (5.7); 2.8970 (10.0); 2.8777 (6.6); 2.7047 (0.5); 2.6694 (0.4); 2.6645 (0.3); 2.5090 (25.5); 2.5047 (50.2); 2.5003 (66.2); 2.4958 (47.6); 2.4915 (22.5); 2.3965 (1.8); 2.3790 (5.5); 2.3608 (7.4); 2.3426 (4.9); 2.3250 (1.6); 2.0738 (3.1); 1.2331 (1.4);
0.0066 (2.0); -0.0014 (40.2); -0.0096 (1.6) 0.0066 (2.0); -0.0014 (40.2); -0.0096 (1.6)
1-071 : 1H-NMR(400.0 MHz, de-DMSO): 1-071: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5998 (11.3); 7.2003 (0.7); 7.1976 (0.7); 7.1801 (1.2); 7.1761 (0.8); 7.1663 (0.7); 7.1621 (0.8); 7.1571 (1.1); 7.1537 (1.3); 7.1363 (0.7); 7.1319 (1.3); 7.1285 (1.3); 7.1110 (0.6); 7.1082 (0.6); 7.0977 (1.0); 7.0942 (0.9); 7.0781 (1.7); 7.0604 (0.9); 7.0567 (0.8); 6.9099 (0.9); 6.9061 (0.9); 6.8901 (1.6); 6.8863 (1.6); 6.8704 (0.8); 6.8667 (0.7); 3.9032 (1.5); 3.7819 (16.0); 3.3287 (120.4); 3.1746 (0.4); 3.1616 (0.4); 2.6757 (0.4); 2.6712 (0.5); 2.6668 (0.4); 2.5065 (65.0); 2.5021 (84.6); 2.4978 (61.2); 2.3291δ = 8.5998 (11.3); 7.2003 (0.7); 7.1976 (0.7); 7.1801 (1.2); 7.1761 (0.8); 7.1663 (0.7); 7.1621 (0.8); 7.1571 (1.1); 7.1537 (1.3); 7.1363 (0.7); 7.1319 (1.3); 7.1285 (1.3); 7.1110 (0.6); 7.1082 (0.6); 7.0977 (1.0); 7.0942 (0.9); 7.0.781 (1.7); 7.0604 (0.9); 7.0567 (0.8); 6.9099 (0.9); 6.9061 (0.9); 6.8901 (1.6); 6.8863 (1.6); 6.8704 (0.8); 6.8667 (0.7); 3.9032 (1.5); 3.7819 (16.0); 3.3287 (120.4); 3.1746 (0.4); 3.1616 (0.4); 2.6757 (0.4); 2.6712 (0.5); 2.6668 (0.4); 2.5065 (65.0); 2.5021 (84.6); 2.4978 (61.2); 2.3291
(0.5); 2.2923 (15.6); -0.0002 (1.0) (0.5); 2.2923 (15.6); -0.0002 (1.0)
1-072: 1H-NMR(400.1 MHz, de-DMSO): 1-072: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.7797 (0.5); 8.5882 (11.7); 7.4866 (3.0); 7.4738 (4.5); 7.3187 (3.8); 7.3078 (1.7); 7.2961 (1.0); 3.8069 (16.0); 3.7363 (0.8);δ = 8.7797 (0.5); 8.5882 (11.7); 7.4866 (3.0); 7.4738 (4.5); 7.3187 (3.8); 7.3078 (1.7); 7.2961 (1.0); 3.8069 (16.0); 3.7363 (0.8);
3.3416 (12.4); 2.5092 (3.7); 2.2988 (15.8); 2.2662 (0.8) 3.3416 (12.4); 2.5092 (3.7); 2.2988 (15.8); 2.2662 (0.8)
1-073: 1H-NMR(400.1 MHz, de-DMSO): 1-073: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.6328 (11.5); 8.3124 (1.5); 8.3026 (1.5); 8.3006 (1.5); 7.6464 (0.8); 7.6419 (0.9); 7.6267 (1.6); 7.6224 (1.6); 7.6076 (1.0); 7.6030 (0.9); 7.1156 (1.3); 7.1034 (1.3); 7.0974 (1.3); 7.0851 (1.2); 6.9120 (2.2); 6.8918 (2.1); 3.7976 (16.0); 3.3369 (66.8); 3.3119 (0.5); 2.8900 (0.8); 2.7306 (0.7); 2.5064 (10.0); 2.5023 (13.2); 2.4982 (9.8); 2.2686 (15.7); 1.2982 (0.4); 1.2575 (0.6);δ = 8.6328 (11.5); 8.3124 (1.5); 8.3026 (1.5); 8.3006 (1.5); 7.6464 (0.8); 7.6419 (0.9); 7.6267 (1.6); 7.6224 (1.6); 7.6076 (1.0); 7.6030 (0.9); 7.1156 (1.3); 7.1034 (1.3); 7.0974 (1.3); 7.0851 (1.2); 6.9120 (2.2); 6.8918 (2.1); 3.7976 (16.0); 3.3369 (66.8); 3.3119 (0.5); 2,800 (0.8); 2.7306 (0.7); 2.5064 (10.0); 2.5023 (13.2); 2.4982 (9.8); 2.2686 (15.7); 1.2982 (0.4); 1.2575 (0.6);
1.2336 (1.7); -0.0010 (0.7) 1.2336 (1.7); -0.0010 (0.7)
1-074: 1H-NMR(400.1 MHz, de-DMSO): 1-074: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 11.2511 (3.0); 8.5750 (1.8); 7.1747 (1.6); 7.1612 (2.0); 7.1527 (3.4); 7.1396 (3.1); 7.1085 (3.2); 7.0865 (4.7); 7.0645 (1.8);δ = 11.2511 (3.0); 8.5750 (1.8); 7.1747 (1.6); 7.1612 (2.0); 7.1527 (3.4); 7.1396 (3.1); 7.1085 (3.2); 7.0865 (4.7); 7.0645 (1.8);
3.7767 (16.0); 2.5018 (45.6); 2.2687 (15.4); 1.2335 (2.0); -0.0013 (7.9) 3.7767 (16.0); 2.5018 (45.6); 2.2687 (15.4); 1.2335 (2.0); -0.0013 (7.9)
1-075: 1H-NMR(400.0 MHz, CDC13): 1-075: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4359 (5.5); 8.4240 (5.6); 7.2981 (1.8); 7.2918 (1.6); 7.2888 (2.1); 7.2801 (3.4); 7.2787 (3.7); 7.2749 (2.3); 7.2708 (3.4); 7.2646 (2.0); 7.2588 (27.0); 7.2487 (0.6); 7.0941 (0.5); 7.0887 (1.3); 7.0852 (1.4); 7.0839 (1.3); 7.0754 (9.7); 7.0667 (1.9); 7.0633 (1.2); 7.0591 (0.6); 7.0562 (0.6); 7.0464 (0.6); 6.9890 (1.5); 6.9770 (3.0); 6.9651 (1.5); 5.2965 (1.2); 5.2605 (7.8); 4.1856δ = 8.4359 (5.5); 8.4240 (5.6); 7.2981 (1.8); 7.2918 (1.6); 7.2888 (2.1); 7.2801 (3.4); 7.2787 (3.7); 7.2749 (2.3); 7.2708 (3.4); 7.2646 (2.0); 7.2588 (27.0); 7.2487 (0.6); 7.0941 (0.5); 7.0887 (1.3); 7.0852 (1.4); 7.0839 (1.3); 7.0754 (9.7); 7.0667 (1.9); 7.0633 (1.2); 7.0591 (0.6); 7.0562 (0.6); 7.0464 (0.6); 6.9890 (1.5); 6.9770 (3.0); 6.9651 (1.5); 5.2965 (1.2); 5.2605 (7.8); 4.1856
(1.1) ; 4.1778 (16.0); 1.5440 (3.6); -0.0002 (5.6) (1.1); 4.1778 (16.0); 1.5440 (3.6); -0.0002 (5.6)
1-076: 1H-NMR(400.0 MHz, CDC13): 1-076: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3902 (12.8); 7.9423 (1.9); 7.9406 (2.0); 7.9394 (2.3); 7.9356 (1.2); 7.9268 (0.7); 7.9217 (3.3); 7.9181 (2.2); 7.5637 (0.5); 7.5454 (1.5); 7.5398 (0.5); 7.5302 (0.8); 7.5268 (1.5); 7.5235 (0.8); 7.4885 (2.1); 7.4849 (1.0); 7.4728 (1.6); 7.4691 (3.1); 7.4655 (0.7); 7.4513 (1.2); 7.4484 (0.8); 7.2602 (38.1); 5.2982 (0.6); 3.7846 (0.6); 3.7571 (16.0); 3.7027 (1.9); 2.5616 (15.8); 2.2933 (0.6); -0.0002 (15.1) 1-077: 'H-NMR(400.0 MHz, CDC13): δ = 8.3902 (12.8); 7.9423 (1.9); 7.9406 (2.0); 7.9394 (2.3); 7.9356 (1.2); 7.9268 (0.7); 7.9217 (3.3); 7.9181 (2.2); 7.5637 (0.5); 7.5454 (1.5); 7.5398 (0.5); 7.5302 (0.8); 7.5268 (1.5); 7.5235 (0.8); 7.4885 (2.1); 7.4849 (1.0); 7.4728 (1.6); 7.4691 (3.1); 7.4655 (0.7); 7.4513 (1.2); 7.4484 (0.8); 7.2602 (38.1); 5.2982 (0.6); 3.7846 (0.6); 3.7571 (16.0); 3.7027 (1.9); 2.5616 (15.8); 2.2933 (0.6); -0.0002 (15.1) 1-077: 'H-NMR (400.0 MHz, CDC13):
δ= 8.4682 (3.6); 8.4563 (3.7); 7.2615 (14.5); 7.2209 (1.8); 7.2157 (0.8); 7.2080 (1.9); 7.2040 (1.1); 7.2026 (1.0); 7.1987 (2.1); 7.1912 (0.9); 7.1858 (1.9); 7.0321 (1.4); 7.0202 (2.7); 7.0082 (1.4); 6.8597 (2.0); 6.8542 (0.8); 6.8427 (0.7); 6.8381 (3.5); 6.8329δ = 8.4682 (3.6); 8.4563 (3.7); 7.2615 (14.5); 7.2209 (1.8); 7.2157 (0.8); 7.2080 (1.9); 7.2040 (1.1); 7.2026 (1.0); 7.1987 (2.1); 7.1912 (0.9); 7.1858 (1.9); 7.0321 (1.4); 7.0202 (2.7); 7.0082 (1.4); 6.8597 (2.0); 6.8542 (0.8); 6.8427 (0.7); 6.8381 (3.5); 6.8329
(1.0) ; 6.8215 (0.6); 6.8160 (1.7); 5.2983 (0.8); 4.1668 (16.0); 3.8611 (16.0); -0.0002 (5.3) (1.0); 6.8215 (0.6); 6.8160 (1.7); 5.2983 (0.8); 4.1668 (16.0); 3.8611 (16.0); -0.0002 (5.3)
1-079: Ή-ΝΜϋ^ΟΟ.Ο MHz, CDC13):  1-079: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, CDC13):
δ= 8.9655 (14.8); 7.4126 (2.1); 7.4090 (3.4); 7.4069 (3.0); 7.4018 (3.3); 7.3985 (2.2); 7.3964 (3.5); 7.3944 (3.3); 7.3881 (0.6); 7.3821 (0.8); 7.3801 (1.2); 7.3754 (1.2); 7.3734 (1.0); 7.3700 (0.7); 7.3583 (0.6); 7.2586 (38.7); 7.1467 (0.7); 7.1446 (1.2); 7.1284 (1.9); 7.1252 (1.9); 7.1234 (1.8); 7.1209 (0.7); 7.1124 (0.8); 7.1072 (2.2); 7.1022 (0.6); 7.0460 (3.4); 7.0419 (1.8); 7.0404 (1.6); 7.0373 (0.5); 7.0318 (0.7); 7.0293 (1.0); 7.0274 (2.3); 7.0265 (2.1); 7.0244 (2.2); 7.0219 (1.5); 7.0040 (0.6); 5.3576 (8.8);δ = 8.9655 (14.8); 7.4126 (2.1); 7.4090 (3.4); 7.4069 (3.0); 7.4018 (3.3); 7.3985 (2.2); 7.3964 (3.5); 7.3944 (3.3); 7.3881 (0.6); 7.3821 (0.8); 7.3801 (1.2); 7.3754 (1.2); 7.3734 (1.0); 7.3700 (0.7); 7.3583 (0.6); 7.2586 (38.7); 7.1467 (0.7); 7.1446 (1.2); 7.1284 (1.9); 7.1252 (1.9); 7.1234 (1.8); 7.1209 (0.7); 7.1124 (0.8); 7.1072 (2.2); 7.1022 (0.6); 7.0460 (3.4); 7.0419 (1.8); 7.0404 (1.6); 7.0373 (0.5); 7.0318 (0.7); 7.0293 (1.0); 7.0274 (2.3); 7.0265 (2.1); 7.0244 (2.2); 7.0219 (1.5); 7.0040 (0.6); 5.3576 (8.8);
5.2967 (1.9); 3.8365 (16.0); 2.3161 (15.3); 1.5424 (1.2); -0.0002 (14.7) 5.2967 (1.9); 3.8365 (16.0); 2.3161 (15.3); 1.5424 (1.2); -0.0002 (14.7)
1-080: 1H-NMR(400.0 MHz, CDC13): 1-080: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.9595 (11.4); 7.2596 (44.5); 7.1740 (0.6); 7.1718 (0.8); 7.1582 (0.7); 7.1558 (1.2); 7.1524 (1.9); 7.1488 (0.9); 7.1400 (0.6); 7.1347 (1.6); 7.1328 (1.5); 7.0823 (0.8); 7.0797 (1.0); 7.0701 (0.8); 7.0660 (3.1); 7.0614 (1.9); 7.0497 (0.8); 7.0457 (2.3); 7.0436δ = 8.9595 (11.4); 7.2596 (44.5); 7.1740 (0.6); 7.1718 (0.8); 7.1582 (0.7); 7.1558 (1.2); 7.1524 (1.9); 7.1488 (0.9); 7.1400 (0.6); 7.1347 (1.6); 7.1328 (1.5); 7.0823 (0.8); 7.0797 (1.0); 7.0701 (0.8); 7.0660 (3.1); 7.0614 (1.9); 7.0497 (0.8); 7.0457 (2.3); 7.0436
(1.3) ; 5.2979 (0.7); 3.9261 (16.0); 3.8426 (13.5); 2.3191 (12.9); 0.0079 (0.5); -0.0002 (17.1); -0.0085 (0.5) (1.3); 5.2979 (0.7); 3.9261 (16.0); 3.8426 (13.5); 2.3191 (12.9); 0.0079 (0.5); -0.0002 (17.1); -0.0085 (0.5)
1-081 : 1H-NMR(400.0 MHz, CDC13): 1-081: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4246 (6.0); 8.4126 (6.2); 7.2616 (13.1); 7.1696 (0.7); 7.1677 (0.9); 7.1537 (0.7); 7.1514 (1.3); 7.1484 (1.8); 7.1475 (1.7); 7.1450 (1.1); 7.1358 (0.6); 7.1303 (1.6); 7.1286 (1.7); 7.0687 (0.8); 7.0661 (1.0); 7.0567 (0.8); 7.0538 (2.6); 7.0523 (3.0); 7.0478δ = 8.4246 (6.0); 8.4126 (6.2); 7.2616 (13.1); 7.1696 (0.7); 7.1677 (0.9); 7.1537 (0.7); 7.1514 (1.3); 7.1484 (1.8); 7.1475 (1.7); 7.1450 (1.1); 7.1358 (0.6); 7.1303 (1.6); 7.1286 (1.7); 7.0687 (0.8); 7.0661 (1.0); 7.0567 (0.8); 7.0538 (2.6); 7.0523 (3.0); 7.0478
(2.1) ; 7.0375 (0.8); 7.0363 (0.8); 7.0321 (2.8); 7.0306 (1.4); 6.9612 (1.7); 6.9492 (3.3); 6.9373 (1.7); 5.2968 (2.0); 4.3645 (1.9); 4.3475 (4.2); 4.3305 (2.0); 3.6936 (15.2); 3.0004 (1.8); 2.9834 (3.8); 2.9664 (1.7); 2.3574 (16.0); 2.0425 (1.0); 1.5885 (0.7);(2.1); 7.0375 (0.8); 7.0363 (0.8); 7.0321 (2.8); 7.0306 (1.4); 6.9612 (1.7); 6.9492 (3.3); 6.9373 (1.7); 5.2968 (2.0); 4.3645 (1.9); 4.3475 (4.2); 4.3305 (2.0); 3.6936 (15.2); 3,0004 (1.8); 2.9834 (3.8); 2.9664 (1.7); 2.3574 (16.0); 2.0425 (1.0); 1.5885 (0.7);
1.2577 (0.6); -0.0002 (5.2) 1.2577 (0.6); -0.0002 (5.2)
1-082: 1H-NMR(400.0 MHz, CDC13): 1-082: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4268 (3.9); 8.4149 (3.9); 7.2600 (33.1); 7.1689 (0.6); 7.1670 (0.9); 7.1527 (0.5); 7.1505 (0.9); 7.1487 (1.3); 7.1458 (2.1); 7.1357 (0.5); 7.1295 (1.8); 7.1282 (1.5); 7.0647 (3.3); 7.0592 (0.8); 7.0511 (0.6); 7.0467 (2.6); 7.0436 (1.4); 6.9568 (1.3); 6.9448δ = 8.4268 (3.9); 8.4149 (3.9); 7.2600 (33.1); 7.1689 (0.6); 7.1670 (0.9); 7.1527 (0.5); 7.1505 (0.9); 7.1487 (1.3); 7.1458 (2.1); 7.1357 (0.5); 7.1295 (1.8); 7.1282 (1.5); 7.0647 (3.3); 7: 0592 (0.8); 7.0511 (0.6); 7.0467 (2.6); 7.0436 (1.4); 6.9568 (1.3); 6.9448
(2.4) ; 6.9329 (1.2); 4.2472 (1.6); 4.2338 (3.1); 4.2201 (1.8); 3.7964 (1.7); 3.7828 (3.0); 3.7694 (1.5); 3.3373 (16.0); 2.3317(2.4); 6.9329 (1.2); 4.2472 (1.6); 4.2338 (3.1); 4.2201 (1.8); 3.7964 (1.7); 3.7828 (3.0); 3.7694 (1.5); 3.3373 (16.0); 2.3317
(13.8); -0.0002 (12.4) (13.8); -0.0002 (12.4)
1-083: !H-NMR^OCO MHZ, CDC13): 1-083 :! H NMR ^ OCO MHZ, CDC13):
δ= 8.4279 (5.8); 8.4160 (6.0); 7.3599 (1.4); 7.3563 (1.7); 7.3514 (6.0); 7.3459 (5.6); 7.3350 (0.8); 7.3238 (0.5); 7.2593 (45.7); 7.1554 (0.6); 7.1531 (1.0); 7.1405 (0.5); 7.1367 (1.0); 7.1340 (1.9); 7.1316 (1.6); 7.1161 (2.3); 7.0658 (2.8); 7.0628 (3.3); 7.0555 (0.9); 7.0529 (0.7); 7.0473 (2.3); 7.0430 (1.9); 7.0400 (1.4); 7.0302 (0.6); 6.9678 (1.6); 6.9559 (3.1); 6.9439 (1.6); 5.2337 (7.2);δ = 8.4279 (5.8); 8.4160 (6.0); 7.3599 (1.4); 7.3563 (1.7); 7.3514 (6.0); 7.3459 (5.6); 7.3350 (0.8); 7.3238 (0.5); 7.2593 (45.7); 7.1554 (0.6); 7.1531 (1.0); 7.1405 (0.5); 7.1367 (1.0); 7.1340 (1.9); 7.1316 (1.6); 7.1161 (2.3); 7.0658 (2.8); 7.0628 (3.3); 7.0555 (0.9); 7.0529 (0.7); 7.0473 (2.3); 7.0430 (1.9); 7.0400 (1.4); 7.0302 (0.6); 6.9678 (1.6); 6.9559 (3.1); 6.9439 (1.6); 5.2337 (7.2);
4.9171 (8.1); 2.2524 (16.0); 1.5530 (1.6); 0.0080 (0.7); -0.0002 (22.8); -0.0084 (0.8) 4.9171 (8.1); 2.2524 (16.0); 1.5530 (1.6); 0.0080 (0.7); -0.0002 (22.8); -0.0084 (0.8)
1-086: 1H-NMR(400.0 MHz, CDC13): 1-086: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.2407 (1.2); 8.2387 (1.2); 7.8571 (0.8); 7.8519 (0.8); 7.8509 (0.8); 7.8365 (0.9); 7.8354 (0.9); 7.8303 (0.8); 7.2597 (21.4); 7.0628 (1.5); 7.0460 (2.0); 7.0409 (2.0); 7.0333 (2.0); 7.0293 (1.0); 7.0280 (1.0); 7.0237 (2.4); 7.0164 (0.9); 7.0110 (2.3); 6.8825 (2.4); 6.8769 (0.7); 6.8656 (0.8); 6.8610 (3.4); 6.8557 (0.8); 6.8444 (0.6); 6.8389 (1.8); 3.8259 (1.2); 3.8199 (16.0); 2.3341 (0.9);δ = 8.2407 (1.2); 8.2387 (1.2); 7.8571 (0.8); 7.8519 (0.8); 7.8509 (0.8); 7.8365 (0.9); 7.8354 (0.9); 7.8303 (0.8); 7.2597 (21.4); 7.0628 (1.5); 7.0460 (2.0); 7.0409 (2.0); 7.0333 (2.0); 7.0293 (1.0); 7.0280 (1.0); 7.0237 (2.4); 7.0164 (0.9); 7.0110 (2.3); 6.8825 (2.4); 6.8769 (0.7); 6.8656 (0.8); 6.8610 (3.4); 6.8557 (0.8); 6.8444 (0.6); 6.8389 (1.8); 3.8259 (1.2); 3.8199 (16.0); 2.3341 (0.9);
2.3225 (15.4); -0.0002 (9.4) 2.3225 (15.4); -0.0002 (9.4)
1-087: 1H-NMR(400.6 MHz, CDC13): 1-087: 1 H-NMR (400.6 MHz, CDC13):
δ= 8.4702 (5.8); 8.4582 (6.0); 7.2629 (7.0); 7.1007 (1.9); 7.0953 (0.8); 7.0879 (2.0); 7.0838 (1.0); 7.0826 (0.9); 7.0784 (2.4); 7.0710 (0.8); 7.0656 (2.2); 7.0000 (1.9); 6.9881 (3.6); 6.9762 (1.8); 6.8815 (2.3); 6.8759 (0.7); 6.8646 (0.8); 6.8598 (3.6); 6.8546δ = 8.4702 (5.8); 8.4582 (6.0); 7.2629 (7.0); 7.1007 (1.9); 7.0953 (0.8); 7.0879 (2.0); 7.0838 (1.0); 7.0826 (0.9); 7.0.784 (2.4); 7.0710 (0.8); 7.0656 (2.2); 7,000 (1.9); 6.9881 (3.6); 6.9762 (1.8); 6.8815 (2.3); 6.8759 (0.7); 6.8646 (0.8); 6.8598 (3.6); 6.8546
(0.7); 6.8432 (0.6); 6.8378 (1.8); 3.8198 (16.0); 2.3090 (15.9); -0.0002 (5.9) (0.7); 6.8432 (0.6); 6.8378 (1.8); 3.8198 (16.0); 2.3090 (15.9); -0.0002 (5.9)
1-088: 1H-NMR(400.0 MHz, de-DMSO): 1-088: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2704 (11.2); 7.2412 (1.2); 7.2371 (0.5); 7.2225 (2.6); 7.2030 (2.0); 7.1160 (1.0); 7.0976 (1.4); 7.0792 (0.6); 7.0314 (2.2); 7.0283 (2.7); 7.0102 (2.2); 3.9029 (1.1); 3.8116 (16.0); 3.7967 (13.4); 3.3249 (54.5); 2.7182 (0.7); 2.6992 (2.3); 2.6802 (2.5); 2.6707 (0.5); 2.6614 (0.8); 2.5240 (0.9); 2.5105 (22.6); 2.5061 (47.0); 2.5016 (62.2); 2.4971 (43.9); 2.4927 (20.6); 2.3284 (0.4);δ = 8.2704 (11.2); 7.2412 (1.2); 7.2371 (0.5); 7.2225 (2.6); 7.2030 (2.0); 7.1160 (1.0); 7.0976 (1.4); 7.0792 (0.6); 7.0314 (2.2); 7.0283 (2.7); 7.0102 (2.2); 3.9029 (1.1); 3.8116 (16.0); 3.7967 (13.4); 3.3249 (54.5); 2.7182 (0.7); 2.6992 (2.3); 2.6802 (2.5); 2.6707 (0.5); 2.6614 (0.8); 2.5240 (0.9); 2.5105 (22.6); 2.5061 (47.0); 2.5016 (62.2); 2.4971 (43.9); 2.4927 (20.6); 2.3284 (0.4);
1.0583 (2.6); 1.0394 (5.9); 1.0204 (2.5); -0.0002 (0.7) 1.0583 (2.6); 1.0394 (5.9); 1.0204 (2.5); -0.0002 (0.7)
1-089: 1H-NMR(400.0 MHz, de-DMSO): 1-089: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2488 (11.0); 7.0998 (0.8); 7.0937 (0.4); 7.0773 (3.2); 7.0622 (1.0); 7.0560 (5.6); 7.0427 (3.2); 7.0343 (1.1); 7.0270 (0.4); 7.0200 (0.6); 3.9031 (1.1); 3.8133 (16.0); 3.7546 (13.4); 3.3245 (61.4); 3.1747 (0.4); 3.1617 (0.4); 2.6705 (0.4); 2.5237 (1.0);δ = 8.2488 (11.0); 7.0998 (0.8); 7.0937 (0.4); 7.0773 (3.2); 7.0622 (1.0); 7.0560 (5.6); 7.0427 (3.2); 7.0343 (1.1); 7.0270 (0.4); 7.0200 (0.6); 3.9031 (1.1); 3.8133 (16.0); 3.7546 (13.4); 3.3245 (61.4); 3.1747 (0.4); 3.1617 (0.4); 2.6705 (0.4); 2.5237 (1.0);
2.5060 (53.9); 2.5017 (70.8); 2.4973 (51.1); 2.3285 (0.4); 2.2712 (13.2); -0.0002 (1.8) 2.5060 (53.9); 2.5017 (70.8); 2.4973 (51.1); 2.3285 (0.4); 2.2712 (13.2); -0.0002 (1.8)
1-090: 1H-NMR(400.0 MHz, de-DMSO): 1-090: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6184 (11.4); 7.1054 (0.9); 7.0993 (0.4); 7.0828 (3.9); 7.0646 (4.3); 7.0616 (4.7); 7.0513 (4.1); 7.0432 (1.3); 7.0356 (0.4); 7.0287 (0.6); 3.9031 (1.2); 3.7669 (16.0); 3.3257 (76.8); 3.1748 (0.3); 2.6711 (0.4); 2.5062 (63.9); 2.5019 (82.6); 2.4977 (59.9);δ = 8.6184 (11.4); 7.1054 (0.9); 7.0993 (0.4); 7.0828 (3.9); 7.0646 (4.3); 7.0616 (4.7); 7.0513 (4.1); 7.0432 (1.3); 7.0356 (0.4); 7.0287 (0.6); 3.9031 (1.2); 3.7669 (16.0); 3.3257 (76.8); 3.1748 (0.3); 2.6711 (0.4); 2.5062 (63.9); 2.5019 (82.6); 2.4977 (59.9);
2.3286 (0.5); 2.2833 (15.8); -0.0002 (1.9) 2.3286 (0.5); 2.2833 (15.8); -0.0002 (1.9)
1-091 : 1H-NMR(400.0 MHz, de-DMSO): 1-091: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6241 (11.7); 7.2753 (1.1); 7.2556 (2.6); 7.2361 (1.9); 7.1841 (1.6); 7.1820 (1.6); 7.1797 (1.4); 7.1667 (0.8); 7.1619 (1.0); 7.0102 (1.4); 7.0059 (3.1); 7.0012 (2.3); 6.9956 (1.9); 6.9761 (1.3); 3.9030 (1.6); 3.7914 (16.0); 3.3264 (100.9); 2.6756 (0.3); 2.6707 (0.5); 2.6663 (0.4); 2.5241 (1.2); 2.5105 (32.6); 2.5064 (66.1); 2.5020 (87.1); 2.4975 (62.7); 2.3331 (0.4); 2.3287 (0.5);δ = 8.6241 (11.7); 7.2753 (1.1); 7.2556 (2.6); 7.2361 (1.9); 7.1841 (1.6); 7.1820 (1.6); 7.1797 (1.4); 7.1667 (0.8); 7.1619 (1.0); 7.0102 (1.4); 7.0059 (3.1); 7.0012 (2.3); 6.9956 (1.9); 6.9761 (1.3); 3.9030 (1.6); 3.7914 (16.0); 3.3264 (100.9); 2.6756 (0.3); 2.6707 (0.5); 2.6663 (0.4); 2.5241 (1.2); 2.5105 (32.6); 2.5064 (66.1); 2.5020 (87.1); 2.4975 (62.7); 2.3331 (0.4); 2.3287 (0.5);
2.3239 (0.4); 2.2850 (15.7); -0.0002 (1.6) 2.3239 (0.4); 2.2850 (15.7); -0.0002 (1.6)
1-092: 1H-NMR(400.0 MHz, de-DMSO): 1-092: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5420 (6.7); 8.5301 (6.9); 7.2947 (0.6); 7.2791 (0.7); 7.2745 (1.3); 7.2590 (1.4); 7.2543 (0.9); 7.2474 (1.8); 7.2354 (3.5); 7.2235 (1.7); 6.9528 (0.6); 6.9466 (0.6); 6.9319 (1.0); 6.9259 (1.1); 6.9100 (0.5); 6.9052 (0.5); 6.8697 (1.3); 6.8676 (1.4); 6.8479 (1.4); 6.8229 (0.9); 6.8176 (1.1); 6.8126 (0.7); 6.7985 (0.9); 6.7935 (1.2); 6.7880 (0.7); 3.9031 (1.4); 3.7934 (16.0); 3.3273 (94.1); 2.6711 (0.4); 2.5243 (1.0); 2.5107 (27.4); 2.5064 (56.5); 2.5020 (74.8); 2.4975 (53.5); 2.4932 (25.7); 2.3287 (0.4); 2.2712 (15.7); -0.0002 (1.7) 1-094: 'H-NMR^O.O MHz, de-DMSO): δ = 8.5420 (6.7); 8.5301 (6.9); 7.2947 (0.6); 7.2791 (0.7); 7.2745 (1.3); 7.2590 (1.4); 7.2543 (0.9); 7.2474 (1.8); 7.2354 (3.5); 7.2235 (1.7); 6.9528 (0.6); 6.9466 (0.6); 6.9319 (1.0); 6.9259 (1.1); 6.9100 (0.5); 6.9052 (0.5); 6.8697 (1.3); 6.8676 (1.4); 6.8479 (1.4); 6.8229 (0.9); 6.8176 (1.1); 6.8126 (0.7); 6.7985 (0.9); 6.7935 (1.2); 6.7880 (0.7); 3.9031 (1.4); 3.7934 (16.0); 3.3273 (94.1); 2.6711 (0.4); 2.5243 (1.0); 2.5107 (27.4); 2.5064 (56.5); 2.5020 (74.8); 2.4975 (53.5); 2.4932 (25.7); 2.3287 (0.4); 2.2712 (15.7); -0.0002 (1.7) 1-094: 'H NMR ^ OO MHz, de-DMSO):
δ= 8.6378 (10.8); 7.2513 (0.6); 7.2285 (1.1); 7.2047 (0.6); 7.2007 (0.6); 7.0196 (1.7); 7.0154 (1.7); 7.0010 (1.8); 6.9951 (1.4); 6.9891 (1.6); 3.9033 (0.9); 3.8121 (0.4); 3.8010 (16.0); 3.3247 (71.6); 2.7650 (0.8); 2.7460 (2.8); 2.7269 (2.8); 2.7080 (0.9); 2.6756 (0.4); 2.6712 (0.5); 2.6666 (0.4); 2.5243 (1.3); 2.5109 (31.1); 2.5066 (63.4); 2.5021 (83.1); 2.4976 (59.0); 2.4933 (28.0);δ = 8.6378 (10.8); 7.2513 (0.6); 7.2285 (1.1); 7.2047 (0.6); 7.2007 (0.6); 7.0196 (1.7); 7.0154 (1.7); 7.0010 (1.8); 6.9951 (1.4); 6.9891 (1.6); 3.9033 (0.9); 3.8121 (0.4); 3.8010 (16.0); 3.3247 (71.6); 2.7650 (0.8); 2.7460 (2.8); 2.7269 (2.8); 2.7080 (0.9); 2.6756 (0.4); 2.6712 (0.5); 2.6666 (0.4); 2.5243 (1.3); 2.5109 (31.1); 2.5066 (63.4); 2.5021 (83.1); 2.4976 (59.0); 2.4933 (28.0);
2.3333 (0.3); 2.3288 (0.5); 2.3245 (0.4); 1.0844 (3.1); 1.0655 (7.1); 1.0465 (3.0); -0.0002 (1.0) 2.3333 (0.3); 2.3288 (0.5); 2.3245 (0.4); 1.0844 (3.1); 1.0655 (7.1); 1.0465 (3.0); -0.0002 (1.0)
1-095: Ή-ΝΜϋ^ΟΟ.Ο MHz, de-DMSO):  1-095: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, de-DMSO):
δ= 8.6309 (13.8); 8.1363 (5.5); 7.0990 (9.5); 7.0846 (4.7); 7.0779 (4.6); 7.0554 (0.4); 3.9031 (0.9); 3.8396 (16.0); 3.3268 (92.3); 2.6709 (0.4); 2.5241 (1.4); 2.5064 (63.3); 2.5020 (82.1); 2.4976 (58.7); 2.3333 (0.4); 2.3286 (0.5); 2.3244 (0.3); -0.0002 (1.1) 1-097: !Η-ΝΜΚ(400.2 MHz, de-DMSO): δ = 8.6309 (13.8); 8.1363 (5.5); 7.0990 (9.5); 7.0846 (4.7); 7.0779 (4.6); 7.0554 (0.4); 3.9031 (0.9); 3.8396 (16.0); 3.3268 (92.3); 2.6709 (0.4); 2.5241 (1.4); 2.5064 (63.3); 2.5020 (82.1); 2.4976 (58.7); 2.3333 (0.4); 2.3286 (0.5); 2.3244 (0.3); -0.0002 (1.1) 1-097 :! Η-ΝΜΚ (400.2 MHz, de-DMSO):
δ= 8.5490 (15.6); 8.5371 (16.0); 7.2524 (4.2); 7.2405 (8.0); 7.2285 (4.1); 7.1214 (1.1); 7.1068 (2.9); 7.0985 (12.4); 7.0932 (13.0); 7.0845 (10.2); 7.0721 (10.0); 7.0559 (1.1); 7.0494 (1.8); 4.1789 (4.2); 4.1609 (6.9); 4.1428 (4.4); 3.3237 (372.2); 2.8974 (3.8); 2.8793 (6.5); 2.8606 (4.6); 2.5527 (1.4); 2.5340 (4.1); 2.5068 (38.1); 2.5025 (50.3); 2.4983 (39.2); 2.4801 (1.6); 1.2362 (2.4);δ = 8.5490 (15.6); 8.5371 (16.0); 7.2524 (4.2); 7.2405 (8.0); 7.2285 (4.1); 7.1214 (1.1); 7.1068 (2.9); 7.0985 (12.4); 7.0932 (13.0); 7.0845 (10.2); 7.0721 (10.0); 7.0559 (1.1); 7.0494 (1.8); 4.1789 (4.2); 4.1609 (6.9); 4.1428 (4.4); 3.3237 (372.2); 2.8974 (3.8); 2.8793 (6.5); 2.8606 (4.6); 2.5527 (1.4); 2.5340 (4.1); 2.5068 (38.1); 2.5025 (50.3); 2.4983 (39.2); 2.4801 (1.6); 1.2362 (2.4);
0.8545 (0.4); 0.0008 (2.2) 0.8545 (0.4); 0.0008 (2.2)
1-098: 1H-NMR(400.0 MHz, CDC13): 1-098: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4430 (11.7); 8.4311 (11.8); 7.2602 (41.9); 7.1633 (15.0); 7.1524 (21.4); 7.1423 (1.0); 7.1330 (0.6); 7.1302 (1.3); 7.1201 (2.2); 7.1108 (2.7); 7.1086 (1.5); 7.0992 (2.4); 7.0960 (0.7); 7.0900 (1.0); 7.0868 (0.8); 7.0101 (3.7); 6.9982 (7.2); 6.9862 (3.6);δ = 8.4430 (11.7); 8.4311 (11.8); 7.2602 (41.9); 7.1633 (15.0); 7.1524 (21.4); 7.1423 (1.0); 7.1330 (0.6); 7.1302 (1.3); 7.1201 (2.2); 7.1108 (2.7); 7.1086 (1.5); 7.0992 (2.4); 7.0960 (0.7); 7.0900 (1.0); 7.0868 (0.8); 7.0101 (3.7); 6.9982 (7.2); 6.9862 (3.6);
5.2973 (1.4); 4.0401 (16.0); 4.0371 (16.0); 4.0343 (6.4); 1.5553 (4.2); -0.0002 (15.7) 5.2973 (1.4); 4.0401 (16.0); 4.0371 (16.0); 4.0343 (6.4); 1.5553 (4.2); -0.0002 (15.7)
1-099: 1H-NMR(400.1 MHz, de-DMSO): 1-099: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.6448 (11.9); 7.3509 (1.8); 7.3466 (3.4); 7.3424 (2.0); 7.0350 (7.0); 7.0307 (7.0); 3.8007 (16.0); 3.3169 (19.5); 2.5052 (15.0);δ = 8.6448 (11.9); 7.3509 (1.8); 7.3466 (3.4); 7.3424 (2.0); 7.0350 (7.0); 7.0307 (7.0); 3.8007 (16.0); 3.3169 (19.5); 2.5052 (15.0);
2.5011 (19.9); 2.4970 (15.0); 2.2908 (15.8); -0.0010 (4.6) 2.5011 (19.9); 2.4970 (15.0); 2.2908 (15.8); -0.0010 (4.6)
1-100: 1H-NMR(400.1 MHz, de-DMSO): 1-100: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.6521 (11.5); 7.0160 (0.5); 7.0111 (0.8); 7.0059 (0.6); 6.9933 (1.0); 6.9880 (1.6); 6.9828 (1.0); 6.9703 (0.5); 6.9648 (0.8); 6.7421 (0.6); 6.7254 (2.8); 6.7101 (2.8); 6.6930 (0.4); 3.7968 (16.0); 3.3442 (3.8); 2.5049 (26.4); 2.5010 (33.7); 2.4970 (25.5);δ = 8.6521 (11.5); 7.0160 (0.5); 7.0111 (0.8); 7.0059 (0.6); 6.9933 (1.0); 6,980 (1.6); 6.9828 (1.0); 6.9703 (0.5); 6.9648 (0.8); 6.7421 (0.6); 6.7254 (2.8); 6.7101 (2.8); 6.6930 (0.4); 3.7968 (16.0); 3.3442 (3.8); 2.5049 (26.4); 2.5010 (33.7); 2.4970 (25.5);
2.2773 (15.7); -0.0012 (7.4) 2.2773 (15.7); -0.0012 (7.4)
1-101 : 1H-NMR(400.1 MHz, de-DMSO): 1-101: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.5126 (3.6); 8.3434 (2.9); 8.3368 (3.1); 8.0548 (2.4); 7.0953 (0.9); 7.0893 (0.5); 7.0730 (4.1); 7.0588 (4.2); 7.0518 (5.2); 7.0449 (4.9); 7.0367 (1.5); 7.0218 (0.6); 3.7683 (16.0); 3.3169 (45.8); 2.5003 (26.2); 2.2843 (15.8); 1.2327 (0.8); -0.0013 (3.7) 1-102: 1H-NMR(400.1 MHz, de-DMSO): δ = 8.5126 (3.6); 8.3434 (2.9); 8.3368 (3.1); 8.0548 (2.4); 7.0953 (0.9); 7.0893 (0.5); 7.0730 (4.1); 7.0588 (4.2); 7.0518 (5.2); 7.0449 (4.9); 7.0367 (1.5); 7.0218 (0.6); 3.7683 (16.0); 3.3169 (45.8); 2.5003 (26.2); 2.2843 (15.8); 1.2327 (0.8); -0.0013 (3.7) 1-102: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.5305 (3.6); 8.3468 (3.0); 8.3402 (3.2); 8.0156 (2.3); 7.2358 (0.7); 7.2301 (0.8); 7.2118 (1.1); 7.2075 (1.6); 7.1848 (0.8); 7.0050 (1.2); 6.9892 (3.4); 6.9702 (2.4); 3.7670 (16.0); 3.3271 (56.6); 2.5017 (18.4); 2.3098 (15.6); 2.0746 (1.2); 1.2331 (0.7); -δ = 8.5305 (3.6); 8.3468 (3.0); 8.3402 (3.2); 8.0156 (2.3); 7.2358 (0.7); 7.2301 (0.8); 7.2118 (1.1); 7.2075 (1.6); 7.1848 (0.8); 7.0050 (1.2); 6.9892 (3.4); 6.9702 (2.4); 3.7670 (16.0); 3.3271 (56.6); 2.5017 (18.4); 2.3098 (15.6); 2.0746 (1.2); 1.2331 (0.7); -
0.0012 (1.6) 0.0012 (1.6)
1-103: 1H-NMR(400.0 MHz, de-DMSO): 1-103: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.4903 (2.5); 8.4845 (2.6); 8.2537 (1.6); 8.2478 (1.6); 8.2322 (1.7); 8.2262 (1.6); 7.1391 (2.6); 7.1175 (2.5); 7.0855 (0.7); 7.0789 (0.4); 7.0627 (3.8); 7.0578 (1.1); 7.0493 (3.8); 7.0416 (4.7); 7.0352 (4.4); 7.0268 (1.0); 7.0199 (0.4); 7.0124 (0.4); 3.9032 (1.2); 3.8384 (15.9); 3.7859 (0.8); 3.7756 (16.0); 3.3282 (149.2); 3.1751 (0.9); 3.1619 (0.8); 3.0988 (0.5); 3.0475 (0.7); 2.8382 (0.5); 2.6757 (0.4); 2.6711 (0.5); 2.6669 (0.4); 2.5243 (1.2); 2.5106 (33.7); 2.5065 (68.8); 2.5021 (91.0); 2.4976 (65.2); 2.4935δ = 8.4903 (2.5); 8.4845 (2.6); 8.2537 (1.6); 8.2478 (1.6); 8.2322 (1.7); 8.2262 (1.6); 7.1391 (2.6); 7.1175 (2.5); 7.0855 (0.7); 7.0.789 (0.4); 7.0627 (3.8); 7.0578 (1.1); 7.0493 (3.8); 7.0416 (4.7); 7.0352 (4.4); 7.0268 (1.0); 7.0199 (0.4); 7.0124 (0.4); 3.9032 (1.2); 3.8384 (15.9); 3,7859 (0.8); 3.7756 (16.0); 3.3282 (149.2); 3.1751 (0.9); 3.1619 (0.8); 3.0988 (0.5); 3.0475 (0.7); 2.8382 (0.5); 2.6757 (0.4); 2.6711 (0.5); 2.6669 (0.4); 2.5243 (1.2); 2.5106 (33.7); 2.5065 (68.8); 2.5021 (91.0); 2.4976 (65.2); 2.4935
(31.5); 2.3332 (0.4); 2.3288 (0.5); 2.3247 (0.4); 2.2872 (14.9); 2.2691 (0.3); -0.0002 (1.0) (31.5); 2.3332 (0.4); 2.3288 (0.5); 2.3247 (0.4); 2.2872 (14.9); 2.2691 (0.3); -0.0002 (1.0)
1-104: 1H-NMR(400.0 MHz, CDC13): 1-104: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3198 (9.0); 7.2611 (16.8); 7.0052 (0.6); 6.9840 (1.0); 6.9802 (0.6); 6.9634 (0.8); 6.9590 (1.0); 6.9384 (0.7); 6.9224 (0.6); 6.9166 (0.7); 6.9041 (0.6); 6.8983 (0.7); 6.8955 (0.7); 6.8897 (0.7); 6.8772 (0.6); 6.8715 (0.7); 6.8169 (0.5); 6.8109 (0.8); 6.8069 (0.6); 6.7893 (0.6); 5.2984 (0.9); 3.9311 (16.0); 1.6860 (0.6); 1.6690 (0.9); 1.6514 (0.6); 1.5522 (1.6); 0.9889 (4.7); 0.9834 (1.2);δ = 8.3198 (9.0); 7.2611 (16.8); 7.0052 (0.6); 6.9840 (1.0); 6.9802 (0.6); 6.9634 (0.8); 6.9590 (1.0); 6.9384 (0.7); 6.9224 (0.6); 6.9166 (0.7); 6.9041 (0.6); 6.8983 (0.7); 6.8955 (0.7); 6.8897 (0.7); 6.8772 (0.6); 6.8715 (0.7); 6.8169 (0.5); 6.8109 (0.8); 6.8069 (0.6); 6.7893 (0.6); 5.2984 (0.9); 3.9311 (16.0); 1.6860 (0.6); 1.6690 (0.9); 1.6514 (0.6); 1.5522 (1.6); 0.9889 (4.7); 0.9834 (1.2);
0.9716 (10.9); -0.0002 (6.3) 0.9716 (10.9); -0.0002 (6.3)
1-105: 1H-NMR(400.0 MHz, CDC13): 1-105: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4840 (5.0); 8.4721 (5.1); 7.2620 (12.4); 7.2321 (0.6); 7.2165 (0.6); 7.2107 (1.0); 7.1950 (1.0); 7.1905 (0.6); 7.0527 (1.5); 7.0407 (2.9); 7.0287 (1.4); 6.7230 (0.5); 6.7165 (0.7); 6.7011 (0.7); 6.6944 (1.8); 6.6930 (1.6); 6.6723 (1.9); 6.6652 (0.8); 6.6519δ = 8.4840 (5.0); 8.4721 (5.1); 7.2620 (12.4); 7.2321 (0.6); 7.2165 (0.6); 7.2107 (1.0); 7.1950 (1.0); 7.1905 (0.6); 7.0527 (1.5); 7.0407 (2.9); 7.0287 (1.4); 6.7230 (0.5); 6.7165 (0.7); 6.7011 (0.7); 6.6944 (1.8); 6.6930 (1.6); 6.6723 (1.9); 6.6652 (0.8); 6.6519
(0.5); 5.2986 (1.3); 4.1615 (16.0); 3.8956 (15.9); -0.0002 (4.5) (0.5); 5.2986 (1.3); 4.1615 (16.0); 3.8956 (15.9); -0.0002 (4.5)
1-106: 1H-NMR(400.0 MHz, CDC13): 1-106: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.5163 (0.5); 8.5043 (0.6); 8.4520 (5.4); 8.4400 (6.1); 8.4281 (0.9); 8.3118 (1.9); 7.2645 (14.4); 6.9965 (1.7); 6.9845 (3.2); 6.9723 (2.1); 6.9628 (3.3); 6.9484 (3.0); 5.2988 (3.0); 3.8713 (16.0); 3.8498 (1.7); 3.6740 (0.8); 2.3298 (0.8); 2.2916 (15.8);δ = 8.5163 (0.5); 8.5043 (0.6); 8.4520 (5.4); 8.4400 (6.1); 8.4281 (0.9); 8.3118 (1.9); 7.2645 (14.4); 6.9965 (1.7); 6.9845 (3.2); 6.9723 (2.1); 6.9628 (3.3); 6.9484 (3.0); 5.2988 (3.0); 3.8713 (16.0); 3.8498 (1.7); 3.6740 (0.8); 2.3298 (0.8); 2.2916 (15.8);
2.2412 (1.4); 1.2560 (1.3); -0.0002 (5.2) 2.2412 (1.4); 1.2560 (1.3); -0.0002 (5.2)
1-107: 1H-NMR(400.0 MHz, CDC13): 1-107: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4490 (0.8); 8.3474 (2.3); 7.5183 (0.7); 7.3098 (0.5); 7.2594 (125.4); 6.9954 (0.7); 6.5861 (2.0); 6.5700 (2.2); 6.5643 (2.3); 6.5482 (2.0); 4.1306 (0.6); 4.1127 (0.6); 3.8270 (5.1); 3.7504 (16.0); 2.4451 (8.5); 2.3329 (3.6); 2.0434 (2.6); 1.5333 (12.8);δ = 8.4490 (0.8); 8.3474 (2.3); 7.5183 (0.7); 7.3098 (0.5); 7.2594 (125.4); 6.9954 (0.7); 6.5861 (2.0); 6.5700 (2.2); 6.5643 (2.3); 6.5482 (2.0); 4.1306 (0.6); 4.1127 (0.6); 3.8270 (5.1); 3.7504 (16.0); 2.4451 (8.5); 2.3329 (3.6); 2.0434 (2.6); 1.5333 (12.8);
1.2765 (0.8); 1.2586 (1.6); 1.2408 (0.7); 0.0079 (1.5); -0.0002 (46.6); -0.0085 (1.3) 1.2765 (0.8); 1.2586 (1.6); 1.2408 (0.7); 0.0079 (1.5); -0.0002 (46.6); -0.0085 (1.3)
1-108: 1H-NMR(400.0 MHz, CDC13): 1-108: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3673 (0.8); 8.3390 (0.7); 8.2982 (0.6); 8.2919 (12.7); 8.2687 (0.7); 7.2632 (21.6); 6.9473 (1.3); 6.9330 (1.3); 5.2986 (3.0);δ = 8.3673 (0.8); 8.3390 (0.7); 8.2982 (0.6); 8.2919 (12.7); 8.2687 (0.7); 7.2632 (21.6); 6.9473 (1.3); 6.9330 (1.3); 5.2986 (3.0);
3.8658 (16.0); 3.8513 (0.8); 2.2905 (15.6); 2.2504 (0.8); -0.0002 (8.2) 3.8658 (16.0); 3.8513 (0.8); 2.2905 (15.6); 2.2504 (0.8); -0.0002 (8.2)
1-110: 1H-NMR(400.0 MHz, CDC13): 1-110: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4293 (5.5); 8.4173 (5.6); 7.2606 (13.3); 7.1722 (0.6); 7.1704 (1.0); 7.1567 (0.6); 7.1540 (0.9); 7.1515 (1.7); 7.1490 (2.0); 7.1327 (2.0); 7.0631 (3.8); 7.0564 (0.8); 7.0499 (0.5); 7.0462 (2.6); 7.0437 (2.2); 7.0406 (1.6); 7.0273 (0.5); 6.9529 (1.6); 6.9410 (3.0); 6.9290 (1.5); 3.8757 (3.8); 3.8571 (3.9); 2.3118 (0.5); 2.2943 (16.0); 2.2779 (0.5); 1.5766 (1.1); 0.9692 (12.2); 0.9524δ = 8.4293 (5.5); 8.4173 (5.6); 7.2606 (13.3); 7.1722 (0.6); 7.1704 (1.0); 7.1567 (0.6); 7.1540 (0.9); 7.1515 (1.7); 7.1490 (2.0); 7.1327 (2.0); 7.0631 (3.8); 7.0564 (0.8); 7.0499 (0.5); 7.0462 (2.6); 7.0437 (2.2); 7.0406 (1.6); 7.0273 (0.5); 6.9529 (1.6); 6.9410 (3.0); 6.9290 (1.5); 3.8757 (3.8); 3.8571 (3.9); 2.3118 (0.5); 2.2943 (16.0); 2.2779 (0.5); 1.5766 (1.1); 0.9692 (12.2); 0.9524
(11.9); -0.0002 (4.9) (11.9); -0.0002 (4.9)
1-111 : !H-NMR^OCO MHZ, CDC13): 1-111 :! H NMR ^ OCO MHZ, CDC13):
δ= 8.4379 (5.7); 8.4259 (5.8); 7.2608 (14.1); 7.1854 (0.7); 7.1835 (1.0); 7.1693 (0.7); 7.1670 (1.0); 7.1650 (1.5); 7.1622 (2.3); 7.1597 (0.5); 7.1522 (0.6); 7.1459 (2.0); 7.1447 (1.7); 7.0815 (0.7); 7.0775 (3.7); 7.0711 (0.9); 7.0631 (0.7); 7.0604 (2.1); 7.0584δ = 8.4379 (5.7); 8.4259 (5.8); 7.2608 (14.1); 7.1854 (0.7); 7.1835 (1.0); 7.1693 (0.7); 7.1670 (1.0); 7.1650 (1.5); 7.1622 (2.3); 7.1597 (0.5); 7.1522 (0.6); 7.1459 (2.0); 7.1447 (1.7); 7.0815 (0.7); 7.0775 (3.7); 7.0711 (0.9); 7.0631 (0.7); 7.0604 (2.1); 7.0584
(2.7) ; 7.0553 (1.7); 7.0406 (0.6); 6.9785 (1.6); 6.9665 (3.1); 6.9545 (1.6); 4.8905 (7.2); 3.8119 (14.5); 2.2909 (16.0); -0.0002(2.7); 7.0553 (1.7); 7.0406 (0.6); 6.9785 (1.6); 6.9665 (3.1); 6.9545 (1.6); 4.8905 (7.2); 3.8119 (14.5); 2.2909 (16.0); -0.0002
(8.8) 1-113: 'H-NMR^OO.O MHz, CDC13): (8.8) 1-113: 'H NMR ^ OO.O MHz, CDC13):
δ= 8.2306 (4.3); 7.2595 (16.2); 7.1787 (1.0); 7.1750 (0.6); 7.1598 (0.9); 7.1083 (0.5); 7.0700 (0.8); 7.0663 (1.2); 7.0487 (0.7);δ = 8.2306 (4.3); 7.2595 (16.2); 7.1787 (1.0); 7.1750 (0.6); 7.1598 (0.9); 7.1083 (0.5); 7.0700 (0.8); 7.0663 (1.2); 7.0487 (0.7);
7.0460 (0.6); 2.6341 (6.1); 1.6561 (16.0); 1.5402 (0.6); -0.0002 (7.7) 7.0460 (0.6); 2.6341 (6.1); 1.6561 (16.0); 1.5402 (0.6); -0.0002 (7.7)
1-114: 'H-NMR^OO.O MHz, CDC13):  1-114: 'H NMR ^ OO.O MHz, CDC13):
δ= 8.7123 (1.9); 7.2610 (29.5); 7.0538 (1.2); 7.0383 (1.3); 7.0322 (2.3); 7.0167 (2.3); 7.0109 (1.3); 6.9955 (1.2); 6.7497 (1.2); 6.7432 (1.4); 6.7279 (1.5); 6.7202 (1.9); 6.7054 (1.8); 6.6984 (2.0); 6.6855 (1.4); 6.6837 (1.7); 6.6815 (1.2); 6.6771 (1.2); 6.6642δ = 8.7123 (1.9); 7.2610 (29.5); 7.0538 (1.2); 7.0383 (1.3); 7.0322 (2.3); 7.0167 (2.3); 7.0109 (1.3); 6.9955 (1.2); 6.7497 (1.2); 6.7432 (1.4); 6.7279 (1.5); 6.7202 (1.9); 6.7054 (1.8); 6.6984 (2.0); 6.6855 (1.4); 6.6837 (1.7); 6.6815 (1.2); 6.6771 (1.2); 6.6642
(0.9); 6.6614 (0.9); 6.6576 (0.6); 6.6549 (0.6); 5.2983 (1.4); 3.8222 (16.0); 2.3926 (15.0); -0.0002 (12.0) (0.9); 6.6614 (0.9); 6.6576 (0.6); 6.6549 (0.6); 5.2983 (1.4); 3.8222 (16.0); 2.3926 (15.0); -0.0002 (12.0)
1-115: 1H-NMR(400.0 MHz, de-DMSO): 1-115: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6123 (11.6); 7.2479 (0.6); 7.2232 (1.2); 7.2203 (1.1); 7.2002 (0.6); 7.1973 (0.6); 7.0023 (1.8); 6.9973 (1.6); 6.9836 (1.7); 6.9770 (1.6); 6.9721 (1.8); 3.9033 (0.9); 3.7643 (16.0); 3.3253 (78.1); 2.6756 (0.4); 2.6711 (0.5); 2.5242 (1.3); 2.5064 (65.4);δ = 8.6123 (11.6); 7.2479 (0.6); 7.2232 (1.2); 7.2203 (1.1); 7.2002 (0.6); 7.1973 (0.6); 7.0023 (1.8); 6.9973 (1.6); 6.9836 (1.7); 6.9770 (1.6); 6.9721 (1.8); 3.9033 (0.9); 3.7643 (16.0); 3.3253 (78.1); 2.6756 (0.4); 2.6711 (0.5); 2.5242 (1.3); 2.5064 (65.4);
2.5020 (84.7); 2.4976 (60.6); 2.3286 (0.5); 2.3242 (0.5); 2.3075 (15.3); -0.0002 (0.8) 2.5020 (84.7); 2.4976 (60.6); 2.3286 (0.5); 2.3242 (0.5); 2.3075 (15.3); -0.0002 (0.8)
1-116: 1H-NMR(400.0 MHz, de-DMSO): 1-116: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.9022 (6.0); 8.8902 (6.1); 7.4960 (1.6); 7.4839 (3.0); 7.4718 (1.5); 7.3646 (0.4); 7.3582 (4.1); 7.3537 (1.4); 7.3413 (1.5); 7.3366 (4.9); 7.1146 (0.6); 7.1079 (4.8); 7.0909 (1.4); 7.0864 (4.1); 3.9133 (16.0); 3.9036 (1.7); 3.3266 (72.3); 3.1753 (0.6); 3.1622 (0.5); 2.6717 (0.5); 2.6401 (15.4); 2.5243 (1.2); 2.5067 (60.6); 2.5025 (78.0); 2.4983 (56.8); 2.3291 (0.4); 0.0000 (1.6) 1-117: 1H-NMR(400.0 MHz, de-DMSO): δ = 8.9022 (6.0); 8.8902 (6.1); 7.4960 (1.6); 7.4839 (3.0); 7.4718 (1.5); 7.3646 (0.4); 7.3582 (4.1); 7.3537 (1.4); 7.3413 (1.5); 7.3366 (4.9); 7.1146 (0.6); 7.1079 (4.8); 7.0909 (1.4); 7.0864 (4.1); 3.9133 (16.0); 3.9036 (1.7); 3.3266 (72.3); 3.1753 (0.6); 3.1622 (0.5); 2.6717 (0.5); 2.6401 (15.4); 2.5243 (1.2); 2.5067 (60.6); 2.5025 (78.0); 2.4983 (56.8); 2.3291 (0.4); 0.0000 (1.6) 1-117: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5539 (6.5); 8.5420 (6.6); 7.4198 (1.4); 7.4130 (1.4); 7.3983 (1.4); 7.3916 (1.4); 7.2538 (1.7); 7.2419 (3.2); 7.2299 (1.6); 7.1925 (0.7); 7.1856 (0.7); 7.1708 (1.3); 7.1640 (1.2); 7.1493 (0.8); 7.1425 (0.8); 6.9392 (1.6); 6.9246 (1.7); 6.9168 (1.4); 6.9022 (1.3); 3.9033 (0.8); 3.8339 (16.0); 3.3254 (74.2); 2.7140 (0.8); 2.6949 (2.8); 2.6758 (3.2); 2.6570 (0.9); 2.5244 (1.2); 2.5109 (29.5); 2.5065 (60.8); 2.5020 (80.3); 2.4975 (56.8); 2.4931 (26.7); 2.3330 (0.3); 2.3288 (0.4); 2.3242 (0.3); 1.0727 (3.2); 1.0538δ = 8.5539 (6.5); 8.5420 (6.6); 7.4198 (1.4); 7.4130 (1.4); 7.3983 (1.4); 7.3916 (1.4); 7.2538 (1.7); 7.2419 (3.2); 7.2299 (1.6); 7.1925 (0.7); 7.1856 (0.7); 7.1708 (1.3); 7.1640 (1.2); 7.1493 (0.8); 7.1425 (0.8); 6.9392 (1.6); 6.9246 (1.7); 6.9168 (1.4); 6.9022 (1.3); 3.9033 (0.8); 3.8339 (16.0); 3.3254 (74.2); 2,7140 (0.8); 2.6949 (2.8); 2.6758 (3.2); 2.6570 (0.9); 2.5244 (1.2); 2.5109 (29.5); 2.5065 (60.8); 2.5020 (80.3); 2.4975 (56.8); 2.4931 (26.7); 2.3330 (0.3); 2.3288 (0.4); 2.3242 (0.3); 1.0727 (3.2); 1.0538
(7.3); 1.0348 (3.0); -0.0003 (1.2) (7.3); 1.0348 (3.0); -0.0003 (1.2)
1-118: 1H-NMR(400.0 MHz, de-DMSO): 1-118: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2775 (7.9); 7.4258 (0.9); 7.4191 (1.0); 7.4044 (1.0); 7.3976 (0.9); 7.1919 (0.4); 7.1852 (0.4); 7.1702 (0.8); 7.1634 (0.8); 7.1488 (0.6); 7.1420 (0.5); 6.9076 (0.9); 6.8929 (0.9); 6.8853 (0.8); 6.8707 (0.7); 3.9031 (0.7); 3.8152 (16.0); 3.3265 (61.2); 2.7075 (0.5); 2.6884 (1.7); 2.6695 (2.0); 2.6506 (0.5); 2.5063 (43.4); 2.5020 (55.4); 2.4976 (39.7); 1.0683 (1.9); 1.0494 (4.2);δ = 8.2775 (7.9); 7.4258 (0.9); 7.4191 (1.0); 7.4044 (1.0); 7.3976 (0.9); 7.1919 (0.4); 7.1852 (0.4); 7.1702 (0.8); 7.1634 (0.8); 7.1488 (0.6); 7.1420 (0.5); 6.9076 (0.9); 6.8929 (0.9); 6.8853 (0.8); 6.8707 (0.7); 3.9031 (0.7); 3.8152 (16.0); 3.3265 (61.2); 2.7075 (0.5); 2.6884 (1.7); 2.6695 (2.0); 2.6506 (0.5); 2.5063 (43.4); 2.5020 (55.4); 2.4976 (39.7); 1.0683 (1.9); 1.0494 (4.2);
1.0304 (1.8); -0.0004 (0.7) 1.0304 (1.8); -0.0004 (0.7)
1-119: 1H-NMR(400.0 MHz, de-DMSO): 1-119: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5515 (5.8); 8.5396 (6.0); 8.2137 (6.0); 7.3079 (4.1); 7.2864 (4.9); 7.2546 (1.5); 7.2427 (2.8); 7.2308 (1.4); 7.0798 (0.6); 7.0730 (4.8); 7.0515 (4.0); 4.5029 (0.4); 4.4865 (1.0); 4.4700 (1.4); 4.4532 (1.0); 4.4367 (0.4); 3.9032 (1.1); 3.6232 (0.4); 3.6096 (0.4); 3.6010 (0.6); 3.3245 (51.0); 2.6708 (0.6); 2.5061 (83.7); 2.5018 (108.6); 2.4975 (78.7); 2.3286 (0.6); 1.4536 (16.0); 1.4370δ = 8.5515 (5.8); 8.5396 (6.0); 8.2137 (6.0); 7.3079 (4.1); 7.2864 (4.9); 7.2546 (1.5); 7.2427 (2.8); 7.2308 (1.4); 7.0798 (0.6); 7.0730 (4.8); 7.0515 (4.0); 4.5029 (0.4); 4.4865 (1.0); 4.4700 (1.4); 4.4532 (1.0); 4.4367 (0.4); 3.9032 (1.1); 3.6232 (0.4); 3.6096 (0.4); 3.6010 (0.6); 3.3245 (51.0); 2.6708 (0.6); 2.5061 (83.7); 2.5018 (108.6); 2.4975 (78.7); 2.3286 (0.6); 1.4536 (16.0); 1.4370
(15.9); 1.3001 (0.3); -0.0002 (1.7) (15.9); 1,3001 (0.3); -0.0002 (1.7)
1-120: 1H-NMR(400.0 MHz, de-DMSO): 1-120: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6215 (14.1); 8.1319 (5.5); 7.2462 (1.4); 7.2278 (3.5); 7.2084 (2.7); 7.1414 (1.3); 7.1232 (1.9); 7.1046 (0.7); 7.0591 (2.9); 7.0560 (3.7); 7.0379 (2.9); 3.9029 (1.1); 3.8508 (16.0); 3.7059 (0.5); 3.3262 (82.9); 2.6709 (0.4); 2.5241 (1.2); 2.5107 (29.2);δ = 8.6215 (14.1); 8.1319 (5.5); 7.2462 (1.4); 7.2278 (3.5); 7.2084 (2.7); 7.1414 (1.3); 7.1232 (1.9); 7.1046 (0.7); 7.0591 (2.9); 7.0560 (3.7); 7.0379 (2.9); 3.9029 (1.1); 3.8508 (16.0); 3.7059 (0.5); 3.3262 (82.9); 2.6709 (0.4); 2.5241 (1.2); 2.5107 (29.2);
2.5064 (60.0); 2.5019 (79.0); 2.4975 (56.2); 2.4934 (27.0); 2.3332 (0.3); 2.3288 (0.4); -0.0002 (1.3) 2.5064 (60.0); 2.5019 (79.0); 2.4975 (56.2); 2.4934 (27.0); 2.3332 (0.3); 2.3288 (0.4); -0.0002 (1.3)
1-121 : 1H-NMR(400.0 MHz, de-DMSO): 1-121: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.7748 (0.4); 8.6326 (16.0); 8.1916 (6.8); 7.0990 (14.2); 7.0813 (8.6); 4.1468 (1.3); 4.1286 (4.2); 4.1105 (4.2); 4.0922 (1.4); 3.9030 (1.1); 3.3274 (110.0); 2.6755 (0.4); 2.6710 (0.5); 2.6667 (0.4); 2.5241 (1.3); 2.5064 (71.0); 2.5020 (93.0); 2.4976 (66.6);δ = 8.7748 (0.4); 8.6326 (16.0); 8.1916 (6.8); 7.0990 (14.2); 7.0813 (8.6); 4.1468 (1.3); 4.1286 (4.2); 4.1105 (4.2); 4.0922 (1.4); 3.9030 (1.1); 3.3274 (110.0); 2.6755 (0.4); 2.6710 (0.5); 2.6667 (0.4); 2.5241 (1.3); 2.5064 (71.0); 2.5020 (93.0); 2.4976 (66.6);
2.3331 (0.4); 2.3286 (0.5); 2.3243 (0.4); 1.4194 (4.8); 1.4012 (10.4); 1.3830 (4.7); 1.3515 (0.4); -0.0003 (0.6) 2.3331 (0.4); 2.3286 (0.5); 2.3243 (0.4); 1.4194 (4.8); 1.4012 (10.4); 1.3830 (4.7); 1.3515 (0.4); -0.0003 (0.6)
1-122: 1H-NMR(400.2 MHz, de-DMSO): 1-122: 1 H-NMR (400.2 MHz, de-DMSO):
δ= 8.6282 (16.0); 7.0940 (16.0); 7.0788 (6.9); 7.0740 (7.1); 7.0588 (0.4); 7.0513 (0.5); 4.1753 (2.2); 4.1572 (3.5); 4.1391 (2.3); 3.3225 (11.2); 2.9086 (2.0); 2.8907 (3.3); 2.8719 (2.4); 2.5490 (0.7); 2.5305 (2.1); 2.5095 (8.0); 2.5049 (13.9); 2.5005 (18.5);δ = 8.6282 (16.0); 7.0940 (16.0); 7.0788 (6.9); 7.0740 (7.1); 7.0588 (0.4); 7.0513 (0.5); 4.1753 (2.2); 4.1572 (3.5); 4.1391 (2.3); 3.3225 (11.2); 2.9086 (2.0); 2.8907 (3.3); 2.8719 (2.4); 2.5490 (0.7); 2.5305 (2.1); 2.5095 (8.0); 2.5049 (13.9); 2.5005 (18.5);
2.4960 (14.4); 2.4761 (0.6); 0.0066 (0.4); -0.0016 (10.7); -0.0097 (0.4) 2.4960 (14.4); 2.4761 (0.6); 0.0066 (0.4); -0.0016 (10.7); -0.0097 (0.4)
1-123: 1H-NMR(400.0 MHz, de-DMSO): 1-123: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5337 (6.6); 8.5217 (6.7); 7.5823 (3.0); 7.5614 (3.3); 7.2384 (1.7); 7.2265 (3.4); 7.2144 (4.8); 7.1935 (2.9); 3.9033 (1.0); 3.8028 (16.0); 3.7306 (0.6); 3.3295 (137.4); 2.6758 (0.4); 2.6716 (0.5); 2.6672 (0.4); 2.5247 (1.3); 2.5110 (32.9); 2.5069 (67.3);δ = 8.5337 (6.6); 8.5217 (6.7); 7.5823 (3.0); 7.5614 (3.3); 7.2384 (1.7); 7.2265 (3.4); 7.2144 (4.8); 7.1935 (2.9); 3.9033 (1.0); 3.8028 (16.0); 3.7306 (0.6); 3.3295 (137.4); 2.6758 (0.4); 2.6716 (0.5); 2.6672 (0.4); 2.5247 (1.3); 2.5110 (32.9); 2.5069 (67.3);
2.5025 (89.2); 2.4981 (64.0); 2.3337 (0.4); 2.3291 (0.5); 2.3249 (0.4); 2.2658 (16.0); -0.0001 (0.4) 2.5025 (89.2); 2.4981 (64.0); 2.3337 (0.4); 2.3291 (0.5); 2.3249 (0.4); 2.2658 (16.0); -0.0001 (0.4)
1-124: 1H-NMR(400.0 MHz, de-DMSO): 1-124: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.7733 (0.8); 8.6134 (11.9); 7.5833 (3.0); 7.5623 (3.4); 7.2030 (3.3); 7.1823 (3.0); 3.9031 (1.8); 3.7997 (16.0); 3.7597 (0.4); 3.7281 (1.2); 3.6361 (0.3); 3.6214 (0.4); 3.3283 (140.2); 3.1618 (0.6); 2.6758 (0.4); 2.6711 (0.6); 2.6667 (0.4); 2.5065 (77.9); 2.5022 (101.2); 2.4977 (72.6); 2.3334 (0.4); 2.3286 (0.6); 2.3247 (0.4); 2.2751 (15.8); 2.2601 (1.3); 1.7249 (0.5); 1.3909 (0.5); -δ = 8.7733 (0.8); 8.6134 (11.9); 7.5833 (3.0); 7.5623 (3.4); 7.2030 (3.3); 7.1823 (3.0); 3.9031 (1.8); 3.7997 (16.0); 3.7597 (0.4); 3.7281 (1.2); 3.6361 (0.3); 3.6214 (0.4); 3.3283 (140.2); 3.1618 (0.6); 2.6758 (0.4); 2.6711 (0.6); 2.6667 (0.4); 2.5065 (77.9); 2.5022 (101.2); 2.4977 (72.6); 2.3334 (0.4); 2.3286 (0.6); 2.3247 (0.4); 2.2751 (15.8); 2.2601 (1.3); 1.7249 (0.5); 1.3909 (0.5); -
0.0003 (1.2) 0.0003 (1.2)
1-125: 1H-NMR(400.0 MHz, CDC13): 1-125: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.6167 (0.8); 8.4264 (10.3); 7.4647 (1.2); 7.4590 (0.5); 7.4513 (2.0); 7.4462 (1.5); 7.4414 (3.5); 7.4347 (5.0); 7.4260 (0.7); 7.3993 (2.2); 7.3900 (2.0); 7.3811 (1.3); 7.3747 (1.1); 7.2592 (33.5); 7.1396 (0.5); 7.1364 (0.9); 7.1235 (0.5); 7.1192 (2.6); 7.1152 (1.5); 7.1037 (0.9); 7.1002 (2.5); 7.0688 (1.1); 7.0653 (0.9); 7.0508 (1.4); 7.0439 (0.5); 7.0390 (2.6); 7.0352 (3.3); 7.0295δ = 8.6167 (0.8); 8.4264 (10.3); 7.4647 (1.2); 7.4590 (0.5); 7.4513 (2.0); 7.4462 (1.5); 7.4414 (3.5); 7.4347 (5.0); 7.4260 (0.7); 7.3993 (2.2); 7.3900 (2.0); 7.3811 (1.3); 7.3747 (1.1); 7.2592 (33.5); 7.1396 (0.5); 7.1364 (0.9); 7.1235 (0.5); 7.1192 (2.6); 7.1152 (1.5); 7.1037 (0.9); 7.1002 (2.5); 7.0688 (1.1); 7.0653 (0.9); 7.0508 (1.4); 7.0439 (0.5); 7.0390 (2.6); 7.0352 (3.3); 7.0295
(0.8); 7.0216 (1.0); 7.0177 (1.9); 5.2973 (3.2); 3.8547 (16.0); 1.5411 (1.5); 1.2561 (1.2); -0.0002 (12.6) (0.8); 7.0216 (1.0); 7.0177 (1.9); 5.2973 (3.2); 3.8547 (16.0); 1.5411 (1.5); 1.2561 (1.2); -0.0002 (12.6)
1-127: 1H-NMR(400.0 MHz, CDC13): 1-127: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.5297 (5.5); 8.5178 (5.8); 7.6347 (2.2); 7.6311 (2.9); 7.6140 (3.4); 7.6131 (3.4); 7.4075 (1.2); 7.3909 (3.5); 7.3716 (2.8); 7.3597 (2.0); 7.3489 (0.7); 7.3422 (1.6); 7.2641 (11.4); 7.0580 (1.6); 7.0461 (3.0); 7.0342 (1.6); 5.2983 (0.6); 3.7323 (16.0);δ = 8.5297 (5.5); 8.5178 (5.8); 7.6347 (2.2); 7.6311 (2.9); 7.6140 (3.4); 7.6131 (3.4); 7.4075 (1.2); 7.3909 (3.5); 7.3716 (2.8); 7.3597 (2.0); 7.3489 (0.7); 7.3422 (1.6); 7.2641 (11.4); 7.0580 (1.6); 7.0461 (3.0); 7.0342 (1.6); 5.2983 (0.6); 3.7323 (16.0);
2.2644 (15.8); 1.2567 (0.6); -0.0002 (4.2) 2.2644 (15.8); 1.2567 (0.6); -0.0002 (4.2)
1-128: 1H-NMR(400.0 MHz, CDC13): 1-128: 1 H-NMR (400.0 MHz, CDC13):
δ= 7.5181 (0.9); 7.3164 (0.5); 7.2589 (161.2); 7.2160 (4.1); 7.1975 (3.3); 7.1130 (5.2); 7.0927 (4.5); 7.0692 (1.0); 6.9944 (1.0); 3.6744 (16.0); 2.2217 (15.2); 2.0437 (0.6); 1.5399 (0.7); 1.2584 (1.0); -0.0002 (58.6) 1-129: 'H-NMR(400.0 MHz, CDC13): δ = 7.5181 (0.9); 7.3164 (0.5); 7.2589 (161.2); 7.2160 (4.1); 7.1975 (3.3); 7.1130 (5.2); 7.0927 (4.5); 7.0692 (1.0); 6.9944 (1.0); 3.6744 (16.0); 2.2217 (15.2); 2.0437 (0.6); 1.5399 (0.7); 1.2584 (1.0); -0.0002 (58.6) 1-129: 'H-NMR (400.0 MHz, CDC13):
δ= 8.4365 (11.0); 8.4245 (11.2); 8.4152 (0.5); 7.5182 (0.9); 7.2859 (2.6); 7.2594 (170.4); 7.2088 (0.9); 7.2014 (1.2); 7.1987 (1.9); 7.1946 (0.9); 7.1852 (1.2); 7.1811 (4.9); 7.1776 (2.7); 7.1656 (2.0); 7.1620 (4.6); 7.1602 (3.2); 7.1562 (1.1); 7.1473 (0.5); 7.1388 (5.1); 7.1217 (1.0); 7.1184 (2.1); 7.1151 (1.9); 7.1055 (0.7); 7.1000 (3.0); 7.0928 (5.3); 7.0890 (5.9); 7.0835 (1.4); 7.0755 (1.7); 7.0716 (3.7); 7.0688 (2.9); 7.0096 (3.2); 6.9977 (6.3); 6.9919 (2.8); 6.9857 (3.2); 2.7310 (0.7); 2.5223 (8.8); 2.5198 (16.0); 2.5172 (8.9); 2.3525 (0.7); 2.3060 (0.6); 2.2011 (1.0); 1.5372 (6.5); 1.2843 (0.7); 1.2558 (6.0); 0.8803 (1.0); 0.0080 (2.0); -0.0002δ = 8.4365 (11.0); 8.4245 (11.2); 8.4152 (0.5); 7.5182 (0.9); 7.2859 (2.6); 7.2594 (170.4); 7.2088 (0.9); 7.2014 (1.2); 7.1987 (1.9); 7.1946 (0.9); 7.1852 (1.2); 7.1811 (4.9); 7.1776 (2.7); 7.1656 (2.0); 7.1620 (4.6); 7.1602 (3.2); 7.1562 (1.1); 7.1473 (0.5); 7.1388 (5.1); 7.1217 (1.0); 7.1184 (2.1); 7.1151 (1.9); 7.1055 (0.7); 7.1000 (3.0); 7.0928 (5.3); 7.0890 (5.9); 7.0835 (1.4); 7.0755 (1.7); 7.0716 (3.7); 7.0688 (2.9); 7.0096 (3.2); 6.9977 (6.3); 6.9919 (2.8); 6.9857 (3.2); 2.7310 (0.7); 2.5223 (8.8); 2.5198 (16.0); 2.5172 (8.9); 2.3525 (0.7); 2.3060 (0.6); 2.2011 (1.0); 1.5372 (6.5); 1.2843 (0.7); 1.2558 (6.0); 0.8803 (1.0); 0.0080 (2.0); -0.0002
(69.5); -0.0085 (2.4) (69.5); -0.0085 (2.4)
1-130: !H-NMR^OCO MHZ, de-DMSO): 1-130 :! H-NMR ^ OCO MHZ, de-DMSO):
δ= 8.6080 (16.0); 8.1033 (0.6); 8.0135 (0.7); 7.0987 (0.8); 7.0910 (3.2); 7.0870 (1.5); 7.0830 (3.6); 7.0770 (2.9); 7.0717 (0.7); 7.0672 (0.8); 7.0617 (3.1); 7.0551 (0.6); 7.0386 (0.6); 3.9371 (14.0); 3.3100 (63.5); 2.5231 (1.5); 2.5184 (2.3); 2.5097 (27.1);δ = 8.6080 (16.0); 8.1033 (0.6); 8.0135 (0.7); 7.0987 (0.8); 7.0910 (3.2); 7.0870 (1.5); 7.0830 (3.6); 7.0770 (2.9); 7.0717 (0.7); 7.0672 (0.8); 7.0617 (3.1); 7.0551 (0.6); 7.0386 (0.6); 3.9371 (14.0); 3.3100 (63.5); 2.5231 (1.5); 2.5184 (2.3); 2.5097 (27.1);
2.5051 (56.9); 2.5005 (78.8); 2.4959 (54.4); 2.4914 (24.6); 2.0724 (1.1); 1.1517 (0.6); -0.0002 (3.1) 2.5051 (56.9); 2,5005 (78.8); 2.4959 (54.4); 2.4914 (24.6); 2.0724 (1.1); 1.1517 (0.6); -0.0002 (3.1)
1-132: 1H-NMR(400.0 MHz, CDC13): 1-132: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4584 (7.6); 8.4465 (7.7); 7.5484 (4.5); 7.5478 (4.5); 7.2604 (40.0); 7.1313 (2.4); 7.1300 (1.6); 7.1255 (1.1); 7.1149 (1.6); 7.1092 (6.4); 7.1038 (1.2); 7.0898 (1.3); 7.0844 (6.4); 7.0787 (1.6); 7.0681 (1.1); 7.0637 (1.6); 7.0623 (2.4); 7.0089 (2.3); 6.9969 (4.5); 6.9850 (2.2); 5.2977 (1.9); 4.1301 (0.7); 4.1123 (0.7); 3.9148 (16.0); 2.0427 (3.3); 1.5546 (2.4); 1.2759 (1.0); 1.2580 (2.3);δ = 8.4584 (7.6); 8.4465 (7.7); 7.5484 (4.5); 7.5478 (4.5); 7.2604 (40.0); 7.1313 (2.4); 7.1300 (1.6); 7.1255 (1.1); 7.1149 (1.6); 7.1092 (6.4); 7.1038 (1.2); 7.0898 (1.3); 7.0844 (6.4); 7.0.787 (1.6); 7.0681 (1.1); 7.0637 (1.6); 7.0623 (2.4); 7.0089 (2.3); 6.9969 (4.5); 6.9850 (2.2); 5.2977 (1.9); 4.1301 (0.7); 4.1123 (0.7); 3.9148 (16.0); 2.0427 (3.3); 1.5546 (2.4); 1.2759 (1.0); 1.2580 (2.3);
1.2401 (1.0); -0.0002 (15.2) 1.2401 (1.0); -0.0002 (15.2)
1-134: 1H-NMR(400.0 MHz, de-DMSO): 1-134: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2508 (11.0); 7.2684 (0.9); 7.2488 (2.1); 7.2294 (1.5); 7.1714 (1.3); 7.1510 (0.8); 7.0031 (1.2); 6.9991 (2.5); 6.9942 (2.8); 6.9720 (1.1); 3.9031 (1.3); 3.8137 (16.0); 3.7796 (13.2); 3.3263 (84.3); 2.6711 (0.4); 2.5240 (1.0); 2.5063 (56.5); 2.5019 (73.8);δ = 8.2508 (11.0); 7.2684 (0.9); 7.2488 (2.1); 7.2294 (1.5); 7.1714 (1.3); 7.1510 (0.8); 7.0031 (1.2); 6.9991 (2.5); 6.9942 (2.8); 6.9720 (1.1); 3.9031 (1.3); 3.8137 (16.0); 3.7796 (13.2); 3.3263 (84.3); 2.6711 (0.4); 2.5240 (1.0); 2.5063 (56.5); 2.5019 (73.8);
2.4975 (52.6); 2.3288 (0.4); 2.2733 (12.9); -0.0002 (1.4) 2.4975 (52.6); 2.3288 (0.4); 2.2733 (12.9); -0.0002 (1.4)
1-135: 1H-NMR(400.0 MHz, de-DMSO): 1-135: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5317 (6.6); 8.5198 (6.8); 7.4191 (1.5); 7.4124 (1.6); 7.3976 (1.6); 7.3909 (1.6); 7.2480 (1.7); 7.2360 (3.3); 7.2240 (1.7); 7.1745 (0.8); 7.1676 (0.7); 7.1528 (1.4); 7.1460 (1.3); 7.1312 (0.9); 7.1245 (0.8); 6.9134 (1.6); 6.8988 (1.7); 6.8911 (1.4); 6.8765 (1.4); 3.9033 (1.0); 3.7972 (16.0); 3.3253 (64.4); 2.6753 (0.4); 2.6710 (0.5); 2.6666 (0.4); 2.5241 (1.3); 2.5105 (31.9); 2.5064δ = 8.5317 (6.6); 8.5198 (6.8); 7.4191 (1.5); 7.4124 (1.6); 7.3976 (1.6); 7.3909 (1.6); 7.2480 (1.7); 7.2360 (3.3); 7.2240 (1.7); 7.1745 (0.8); 7.1676 (0.7); 7.1528 (1.4); 7.1460 (1.3); 7.1312 (0.9); 7.1245 (0.8); 6.9134 (1.6); 6.8988 (1.7); 6.8911 (1.4); 6.8765 (1.4); 3.9033 (1.0); 3.7972 (16.0); 3.3253 (64.4); 2.6753 (0.4); 2.6710 (0.5); 2.6666 (0.4); 2.5241 (1.3); 2.5105 (31.9); 2.5064
(64.0); 2.5020 (83.9); 2.4976 (60.0); 2.3328 (0.3); 2.3289 (0.5); 2.3246 (0.4); 2.2580 (15.9); -0.0002 (0.8) (64.0); 2.5020 (83.9); 2.4976 (60.0); 2.3328 (0.3); 2.3289 (0.5); 2.3246 (0.4); 2.2580 (15.9); -0.0002 (0.8)
1-136: 1H-NMR(400.0 MHz, de-DMSO): 1-136: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5470 (6.2); 8.5350 (6.4); 7.2514 (1.7); 7.2394 (3.8); 7.2275 (1.7); 7.2155 (1.0); 7.2109 (1.3); 7.1881 (0.8); 7.0290 (1.1); 7.0247 (1.0); 7.0178 (1.9); 7.0138 (2.3); 7.0043 (0.9); 6.9989 (2.3); 3.9035 (0.8); 3.8061 (16.0); 3.3255 (68.3); 2.7569 (0.9); 2.7380 (2.9); 2.7190 (3.0); 2.7000 (1.0); 2.6755 (0.4); 2.6716 (0.5); 2.5243 (1.3); 2.5066 (62.1); 2.5023 (80.6); 2.4979 (57.7);δ = 8.5470 (6.2); 8.5350 (6.4); 7.2514 (1.7); 7.2394 (3.8); 7.2275 (1.7); 7.2155 (1.0); 7.2109 (1.3); 7.1881 (0.8); 7.0290 (1.1); 7.0247 (1.0); 7.0178 (1.9); 7.0138 (2.3); 7.0043 (0.9); 6.9989 (2.3); 3.9035 (0.8); 3.8061 (16.0); 3.3255 (68.3); 2.7569 (0.9); 2.7380 (2.9); 2.7190 (3.0); 2.7000 (1.0); 2.6755 (0.4); 2.6716 (0.5); 2.5243 (1.3); 2.5066 (62.1); 2.5023 (80.6); 2.4979 (57.7);
2.3331 (0.3); 2.3290 (0.4); 2.3247 (0.3); 1.0803 (3.2); 1.0614 (7.2); 1.0424 (3.1); -0.0001 (1.1) 2.3331 (0.3); 2.3290 (0.4); 2.3247 (0.3); 1.0803 (3.2); 1.0614 (7.2); 1.0424 (3.1); -0.0001 (1.1)
1-137: 1H-NMR(400.0 MHz, de-DMSO): 1-137: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.7769 (0.3); 8.6337 (12.8); 8.2249 (5.8); 7.0978 (10.7); 7.0801 (11.7); 4.4950 (0.4); 4.4784 (1.0); 4.4617 (1.4); 4.4452 (1.1); 4.4286 (0.4); 3.9031 (0.8); 3.3246 (67.8); 2.6753 (0.3); 2.6709 (0.4); 2.6667 (0.3); 2.5242 (1.2); 2.5105 (31.2); 2.5064 (63.2); 2.5020 (82.7); 2.4976 (58.8); 2.3330 (0.4); 2.3285 (0.5); 2.3241 (0.4); 1.4460 (16.0); 1.4294 (15.8); 1.3982 (0.6); 1.3816 (0.5); -δ = 8.7769 (0.3); 8.6337 (12.8); 8.2249 (5.8); 7.0978 (10.7); 7.0801 (11.7); 4.4950 (0.4); 4.4784 (1.0); 4.4617 (1.4); 4.4452 (1.1); 4.4286 (0.4); 3.9031 (0.8); 3.3246 (67.8); 2.6753 (0.3); 2.6709 (0.4); 2.6667 (0.3); 2.5242 (1.2); 2.5105 (31.2); 2.5064 (63.2); 2.5020 (82.7); 2.4976 (58.8); 2.3330 (0.4); 2.3285 (0.5); 2.3241 (0.4); 1.4460 (16.0); 1.4294 (15.8); 1.3982 (0.6); 1.3816 (0.5); -
0.0002 (1.2) 0.0002 (1.2)
1-138: 1H-NMR(400.0 MHz, de-DMSO): 1-138: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6227 (16.0); 8.1868 (6.7); 7.2491 (1.6); 7.2305 (3.9); 7.2112 (2.9); 7.1411 (1.4); 7.1227 (2.1); 7.1044 (0.8); 7.0554 (3.1); 7.0522 (4.1); 7.0342 (3.2); 4.1581 (1.3); 4.1399 (4.2); 4.1218 (4.2); 4.1036 (1.4); 3.9030 (1.1); 3.3287 (147.3); 2.6755 (0.4); 2.6709 (0.5); 2.6663 (0.4); 2.5242 (1.3); 2.5107 (35.5); 2.5064 (73.5); 2.5019 (97.5); 2.4974 (69.4); 2.4931 (33.1); 2.3331 (0.4);δ = 8.6227 (16.0); 8.1868 (6.7); 7.2491 (1.6); 7.2305 (3.9); 7.2112 (2.9); 7.1411 (1.4); 7.1227 (2.1); 7.1044 (0.8); 7.0554 (3.1); 7.0522 (4.1); 7.0342 (3.2); 4.1581 (1.3); 4.1399 (4.2); 4.1218 (4.2); 4.1036 (1.4); 3.9030 (1.1); 3.3287 (147.3); 2.6755 (0.4); 2.6709 (0.5); 2.6663 (0.4); 2.5242 (1.3); 2.5107 (35.5); 2.5064 (73.5); 2.5019 (97.5); 2.4974 (69.4); 2.4931 (33.1); 2.3331 (0.4);
2.3286 (0.6); 2.3243 (0.4); 1.4272 (5.0); 1.4091 (10.8); 1.3909 (4.8); -0.0002 (0.8) 2.3286 (0.6); 2.3243 (0.4); 1.4272 (5.0); 1.4091 (10.8); 1.3909 (4.8); -0.0002 (0.8)
1-139: 1H-NMR(400.0 MHz, de-DMSO): 1-139: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6323 (11.0); 8.2260 (5.8); 7.3115 (4.1); 7.3070 (1.5); 7.2900 (5.0); 7.0726 (0.6); 7.0656 (4.9); 7.0441 (4.2); 4.5009 (0.4); 4.4844 (1.1); 4.4678 (1.5); 4.4513 (1.1); 4.4347 (0.4); 3.9031 (0.8); 3.3235 (64.8); 2.6708 (0.5); 2.6665 (0.4); 2.5059 (69.5);δ = 8.6323 (11.0); 8.2260 (5.8); 7.3115 (4.1); 7.3070 (1.5); 7.2900 (5.0); 7.0726 (0.6); 7.0656 (4.9); 7.0441 (4.2); 4.5009 (0.4); 4.4844 (1.1); 4.4678 (1.5); 4.4513 (1.1); 4.4347 (0.4); 3.9031 (0.8); 3.3235 (64.8); 2.6708 (0.5); 2.6665 (0.4); 2.5059 (69.5);
2.5017 (91.0); 2.4974 (67.6); 2.3281 (0.5); 2.3239 (0.4); 1.4494 (16.0); 1.4328 (15.9); -0.0001 (1.3) 2.5017 (91.0); 2.4974 (67.6); 2.3281 (0.5); 2.3239 (0.4); 1.4494 (16.0); 1.4328 (15.9); -0.0001 (1.3)
1-126: 1H-NMR(400.0 MHz, CDC13): 1-126: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4500 (3.2); 8.4380 (3.3); 8.0172 (1.7); 7.2640 (20.2); 7.1723 (0.8); 7.1557 (1.3); 7.1530 (1.6); 7.1511 (1.3); 7.1398 (0.6); 7.1350 (1.7); 7.0886 (1.4); 7.0849 (2.5); 7.0793 (0.6); 7.0748 (0.9); 7.0704 (1.0); 7.0670 (1.5); 7.0639 (1.1); 7.0590 (0.6); 7.0541δ = 8.4500 (3.2); 8.4380 (3.3); 8.0172 (1.7); 7.2640 (20.2); 7.1723 (0.8); 7.1557 (1.3); 7.1530 (1.6); 7.1511 (1.3); 7.1398 (0.6); 7.1350 (1.7); 7.0886 (1.4); 7.0849 (2.5); 7.0793 (0.6); 7.0748 (0.9); 7.0704 (1.0); 7.0670 (1.5); 7.0639 (1.1); 7.0590 (0.6); 7.0541
(1.0) ; 6.9718 (1.2); 6.9598 (2.3); 6.9479 (1.2); 3.8308 (11.3); 2.9548 (16.0); 2.8831 (14.0); 2.8818 (13.4); 2.3025 (11.0); 2.0431(1.0); 6.9718 (1.2); 6.9598 (2.3); 6.9479 (1.2); 3.8308 (11.3); 2.9548 (16.0); 2.8831 (14.0); 2.8818 (13.4); 2.3025 (11.0); 2.0431
(2.1) ; 1.6233 (1.6); 1.2761 (0.6); 1.2582 (1.3); 1.2404 (0.6); -0.0002 (7.0) (2.1); 1.6233 (1.6); 1.2761 (0.6); 1.2582 (1.3); 1.2404 (0.6); -0.0002 (7.0)
1-140: 1H-NMR(400.0 MHz, CDC13): 1-140: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3815 (0.8); 8.1903 (0.8); 8.0781 (8.9); 7.2603 (27.4); 7.1746 (0.6); 7.1727 (0.9); 7.1582 (0.7); 7.1545 (1.4); 7.1516 (2.0); 7.1414 (0.6); 7.1352 (1.9); 7.0736 (3.6); 7.0683 (0.8); 7.0557 (2.8); 7.0527 (1.4); 7.0374 (0.5); 3.8913 (1.3); 3.8761 (0.8); 3.8716 (0.6); 3.8334 (1.1); 3.8198 (12.6); 3.8054 (16.0); 3.7757 (0.6); 2.3111 (1.0); 2.2959 (12.4); 2.2819 (0.7); 1.5610 (0.6); -0.0002δ = 8.3815 (0.8); 8.1903 (0.8); 8.0781 (8.9); 7.2603 (27.4); 7.1746 (0.6); 7.1727 (0.9); 7.1582 (0.7); 7.1545 (1.4); 7.1516 (2.0); 7.1414 (0.6); 7.1352 (1.9); 7.0736 (3.6); 7.0683 (0.8); 7.0557 (2.8); 7.0527 (1.4); 7.0374 (0.5); 3.8913 (1.3); 3.8761 (0.8); 3.8716 (0.6); 3.8334 (1.1); 3.8198 (12.6); 3.8054 (16.0); 3.7757 (0.6); 2.3111 (1.0); 2.2959 (12.4); 2.2819 (0.7); 1.5610 (0.6); -0.0002
(10-5) (10-5)
1-141 : 1H-NMR(400.0 MHz, CDC13): 1-141: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4505 (2.6); 8.4471 (2.7); 8.2437 (2.5); 8.2370 (2.6); 7.9822 (1.6); 7.9787 (1.6); 7.9755 (1.6); 7.9720 (1.5); 7.2603 (31.2); 7.0045 (0.6); 6.9834 (1.0); 6.9795 (0.7); 6.9628 (0.8); 6.9585 (1.0); 6.9377 (0.7); 6.8994 (0.6); 6.8936 (0.7); 6.8812 (0.6); 6.8754 (0.8); 6.8727 (0.7); 6.8668 (0.7); 6.8544 (0.6); 6.8486 (0.7); 6.8016 (0.5); 6.7959 (0.8); 6.7918 (0.6); 6.7743 (0.6); 3.8325 (16.0);δ = 8.4505 (2.6); 8.4471 (2.7); 8.2437 (2.5); 8.2370 (2.6); 7.9822 (1.6); 7.9787 (1.6); 7.9755 (1.6); 7.9720 (1.5); 7.2603 (31.2); 7.0045 (0.6); 6.9834 (1.0); 6.9795 (0.7); 6.9628 (0.8); 6.9585 (1.0); 6.9377 (0.7); 6.8994 (0.6); 6.8936 (0.7); 6.8812 (0.6); 6.8754 (0.8); 6.8727 (0.7); 6.8668 (0.7); 6.8544 (0.6); 6.8486 (0.7); 6.8016 (0.5); 6.7959 (0.8); 6.7918 (0.6); 6.7743 (0.6); 3.8325 (16.0);
2.3102 (15.7); 1.5488 (2.2); -0.0002 (10.8) 2.3102 (15.7); 1.5488 (2.2); -0.0002 (10.8)
1-093: 1H-NMR(400.0 MHz, CDC13): 1-093: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3249 (7.1); 7.2599 (57.3); 7.0078 (0.6); 6.9866 (1.0); 6.9828 (0.7); 6.9661 (0.8); 6.9617 (1.0); 6.9411 (0.8); 6.9205 (0.6); 6.9147 (0.7); 6.9023 (0.7); 6.8964 (0.8); 6.8938 (0.7); 6.8879 (0.8); 6.8755 (0.6); 6.8698 (0.7); 6.8256 (0.6); 6.8195 (0.9); 6.8156δ = 8.3249 (7.1); 7.2599 (57.3); 7.0078 (0.6); 6.9866 (1.0); 6.9828 (0.7); 6.9661 (0.8); 6.9617 (1.0); 6.9411 (0.8); 6.9205 (0.6); 6.9147 (0.7); 6.9023 (0.7); 6.8964 (0.8); 6.8938 (0.7); 6.8879 (0.8); 6.8755 (0.6); 6.8698 (0.7); 6.8256 (0.6); 6.8195 (0.9); 6.8156
(0.6); 6.7979 (0.7); 3.8347 (16.0); 2.3045 (14.4); 1.5362 (9.7); 0.0079 (0.7); -0.0002 (20.6); -0.0084 (0.6) (0.6); 6.7979 (0.7); 3.8347 (16.0); 2.3045 (14.4); 1.5362 (9.7); 0.0079 (0.7); -0.0002 (20.6); -0.0084 (0.6)
1-142: 1H-NMR(400.0 MHz, CDC13): 1-142: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.6029 (0.5); 8.5910 (0.5); 8.4387 (6.0); 8.4267 (6.1); 7.3159 (2.0); 7.3139 (1.8); 7.3120 (1.8); 7.2983 (0.8); 7.2941 (1.5); 7.2905 (1.3); 7.2707 (1.7); 7.2622 (16.9); 7.2535 (1.8); 7.2485 (1.6); 7.2439 (0.7); 6.9757 (1.8); 6.9638 (3.4); 6.9518 (1.7); 3.8548 (16.0); 3.7874 (1.6); 2.3041 (15.7); 2.2930 (1.6); 1.5800 (0.9); -0.0002 (5.6) 1-143: 'H-NMR^O.l MHz, de-DMSO): δ = 8.6029 (0.5); 8.5910 (0.5); 8.4387 (6.0); 8.4267 (6.1); 7.3159 (2.0); 7.3139 (1.8); 7.3120 (1.8); 7.2983 (0.8); 7.2941 (1.5); 7.2905 (1.3); 7.2707 (1.7); 7.2622 (16.9); 7.2535 (1.8); 7.2485 (1.6); 7.2439 (0.7); 6.9757 (1.8); 6.9638 (3.4); 6.9518 (1.7); 3.8548 (16.0); 3.7874 (1.6); 2.3041 (15.7); 2.2930 (1.6); 1.5800 (0.9); -0.0002 (5.6) 1-143: 'H-NMR ^ Ol MHz, de-DMSO):
δ= 8.6258 (5.8); 8.6138 (6.0); 7.2633 (1.6); 7.2513 (3.1); 7.2394 (1.6); 7.1094 (2.7); 7.1042 (1.2); 7.0928 (1.5); 7.0875 (5.6); 7.0814 (1.0); 7.0535 (1.0); 7.0474 (5.6); 7.0421 (1.6); 7.0306 (1.1); 7.0255 (2.7); 3.7914 (16.0); 3.6787 (14.6); 3.3279 (31.5);δ = 8.6258 (5.8); 8.6138 (6.0); 7.2633 (1.6); 7.2513 (3.1); 7.2394 (1.6); 7.1094 (2.7); 7.1042 (1.2); 7.0928 (1.5); 7.0875 (5.6); 7.0814 (1.0); 7.0535 (1.0); 7.0474 (5.6); 7.0421 (1.6); 7.0306 (1.1); 7.0255 (2.7); 3.7914 (16.0); 3.6787 (14.6); 3.3279 (31.5);
2.5054 (18.1); 2.5011 (24.0); 2.4969 (17.9); 2.2312 (14.6); 2.0748 (0.4); 1.2347 (0.5); -0.0009 (3.6) 2.5054 (18.1); 2.5011 (24.0); 2.4969 (17.9); 2.2312 (14.6); 2.0748 (0.4); 1.2347 (0.5); -0.0009 (3.6)
1-144: Ή-ΝΜϋ^ΟΟ.Ι MHz, de-DMSO):  1-144: Ή-ΝΜϋ ^ ΟΟ.Ι MHz, de-DMSO):
δ= 8.6688 (11.4); 8.5695 (6.1); 8.5574 (6.2); 7.2356 (1.7); 7.2235 (3.2); 7.2114 (1.6); 3.7799 (16.0); 3.4461 (28.4); 2.5401 (1.0);δ = 8.6688 (11.4); 8.5695 (6.1); 8.5574 (6.2); 7.2356 (1.7); 7.2235 (3.2); 7.2114 (1.6); 3.7799 (16.0); 3.4461 (28.4); 2.5401 (1.0);
2.5007 (34.2); 2.2499 (15.7); 2.0069 (0.3); 1.9876 (0.4); 1.2334 (2.6); 0.8523 (0.4); -0.0012 (2.0) 2.5007 (34.2); 2.2499 (15.7); 2.0069 (0.3); 1.9876 (0.4); 1.2334 (2.6); 0.8523 (0.4); -0.0012 (2.0)
1-145: 1H-NMR(400.0 MHz, CDC13): 1-145: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4804 (5.6); 8.4684 (5.7); 7.2600 (55.5); 7.0066 (1.7); 6.9946 (3.3); 6.9865 (0.6); 6.9826 (1.6); 6.9651 (0.9); 6.9614 (0.6); 6.9447 (0.8); 6.9399 (1.5); 6.9341 (0.7); 6.9198 (0.9); 6.9159 (0.7); 6.9129 (0.7); 6.9071 (0.6); 6.8945 (0.5); 6.8888 (0.6); 6.8216 (0.7); 6.8177 (0.5); 6.8000 (0.5); 3.9360 (16.0); 1.6872 (0.5); 1.6705 (1.0); 1.6529 (0.6); 1.5403 (3.2); 0.9875 (11.6); 0.9767δ = 8.4804 (5.6); 8.4684 (5.7); 7.2600 (55.5); 7.0066 (1.7); 6.9946 (3.3); 6.9865 (0.6); 6.9826 (1.6); 6.9651 (0.9); 6.9614 (0.6); 6.9447 (0.8); 6.9399 (1.5); 6.9341 (0.7); 6.9198 (0.9); 6.9159 (0.7); 6.9129 (0.7); 6.9071 (0.6); 6.8945 (0.5); 6.8888 (0.6); 6.8216 (0.7); 6.8177 (0.5); 6.8000 (0.5); 3.9360 (16.0); 1.6872 (0.5); 1.6705 (1.0); 1.6529 (0.6); 1.5403 (3.2); 0.9875 (11.6); 0.9767
(1.0); 0.9710 (3.3); 0.9692 (3.5); 0.9634 (1.0); 0.0080 (0.6); -0.0002 (20.2); -0.0085 (0.6) (1.0); 0.9710 (3.3); 0.9692 (3.5); 0.9634 (1.0); 0.0080 (0.6); -0.0002 (20.2); -0.0085 (0.6)
1-146: 1H-NMR(400.0 MHz, CDC13): 1-146: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.2496 (10.4); 7.2605 (11.8); 7.1711 (0.9); 7.1558 (1.2); 7.1512 (2.8); 7.1380 (0.7); 7.1337 (2.0); 7.0736 (1.0); 7.0708 (1.0); 7.0558 (4.7); 7.0517 (3.0); 7.0389 (1.1); 7.0346 (2.9); 5.2968 (1.3); 3.9277 (16.0); 1.6975 (0.6); 1.6902 (0.6); 1.6799 (0.6); 1.6767 (1.0); 1.6628 (0.6); 1.6555 (0.6); 1.5636 (0.7); 1.0302 (0.5); 1.0159 (1.3); 1.0117 (1.6); 1.0024 (2.6); 0.9976 (1.4); 0.9889δ = 8.2496 (10.4); 7.2605 (11.8); 7.1711 (0.9); 7.1558 (1.2); 7.1512 (2.8); 7.1380 (0.7); 7.1337 (2.0); 7.0736 (1.0); 7.0708 (1.0); 7.0558 (4.7); 7.0517 (3.0); 7.0389 (1.1); 7.0346 (2.9); 5.2968 (1.3); 3.9277 (16.0); 1.6975 (0.6); 1.6902 (0.6); 1.6799 (0.6); 1.6767 (1.0); 1.6628 (0.6); 1.6555 (0.6); 1.5636 (0.7); 1.0302 (0.5); 1.0159 (1.3); 1.0117 (1.6); 1.0024 (2.6); 0.9976 (1.4); 0.9889
(1.0); 0.9839 (0.6); 0.9740 (1.6); 0.9646 (1.5); 0.9616 (1.1); 0.9530 (1.1); 0.9453 (1.6); 0.9393 (1.1); -0.0002 (4.3) (1.0); 0.9839 (0.6); 0.9740 (1.6); 0.9646 (1.5); 0.9616 (1.1); 0.9530 (1.1); 0.9453 (1.6); 0.9393 (1.1); -0.0002 (4.3)
1-147: 1H-NMR(400.0 MHz, CDC13): 1-147: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.2497 (10.4); 7.2596 (41.6); 7.1656 (1.2); 7.1448 (3.1); 7.1272 (3.1); 7.0774 (5.4); 7.0572 (4.1); 7.0379 (0.8); 5.2981 (1.4); 3.8438 (16.0); 3.7979 (0.8); 2.7006 (2.2); 2.6813 (3.0); 2.6614 (2.5); 1.5872 (1.2); 1.5678 (2.1); 1.5416 (9.7); 1.5115 (0.5);δ = 8.2497 (10.4); 7.2596 (41.6); 7.1656 (1.2); 7.1448 (3.1); 7.1272 (3.1); 7.0774 (5.4); 7.0572 (4.1); 7.0379 (0.8); 5.2981 (1.4); 3.8438 (16.0); 3.7979 (0.8); 2.7006 (2.2); 2.6813 (3.0); 2.6614 (2.5); 1.5872 (1.2); 1.5678 (2.1); 1.5416 (9.7); 1.5115 (0.5);
1.2552 (0.9); 0.9439 (3.9); 0.9256 (7.6); 0.9072 (3.6); -0.0002 (13.9) 1.2552 (0.9); 0.9439 (3.9); 0.9256 (7.6); 0.9072 (3.6); -0.0002 (13.9)
1-148: 1H-NMR(400.0 MHz, CDC13): 1-148: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4635 (6.2); 8.4515 (6.2); 7.4399 (0.8); 7.4351 (3.9); 7.4302 (1.5); 7.4183 (1.6); 7.4133 (4.5); 7.4086 (0.8); 7.2604 (45.6); 7.1364 (0.9); 7.1317 (4.4); 7.1268 (1.6); 7.1148 (1.5); 7.1099 (3.9); 7.1051 (0.7); 7.0144 (2.0); 7.0025 (3.7); 6.9905 (1.9); 5.2985δ = 8.4635 (6.2); 8.4515 (6.2); 7.4399 (0.8); 7.4351 (3.9); 7.4302 (1.5); 7.4183 (1.6); 7.4133 (4.5); 7.4086 (0.8); 7.2604 (45.6); 7.1364 (0.9); 7.1317 (4.4); 7.1268 (1.6); 7.1148 (1.5); 7.1099 (3.9); 7.1051 (0.7); 7.0144 (2.0); 7.0025 (3.7); 6.9905 (1.9); 5.2985
(1.2); 3.8668 (16.0); 2.9551 (1.0); 2.8838 (0.9); 2.8825 (0.9); 2.2904 (15.7); 1.5441 (5.0); -0.0002 (10.3) (1.2); 3.8668 (16.0); 2.9551 (1.0); 2.8838 (0.9); 2.8825 (0.9); 2.2904 (15.7); 1.5441 (5.0); -0.0002 (10.3)
1-149: 1H-NMR(400.0 MHz, CDC13): 1-149: 1 H-NMR (400.0 MHz, CDC13):
δ= 7.2615 (5.5); 7.1629 (0.6); 7.1433 (1.6); 7.1250 (1.6); 7.0934 (2.3); 7.0760 (1.2); 7.0489 (0.6); 7.0314 (0.9); 6.6503 (2.2);δ = 7.2615 (5.5); 7.1629 (0.6); 7.1433 (1.6); 7.1250 (1.6); 7.0934 (2.3); 7.0760 (1.2); 7.0489 (0.6); 7.0314 (0.9); 6.6503 (2.2);
3.8191 (8.3); 2.2837 (16.0); 2.2551 (8.4); 1.6068 (0.5); -0.0002 (2.1) 3.8191 (8.3); 2.2837 (16.0); 2.2551 (8.4); 1.6068 (0.5); -0.0002 (2.1)
1-150: 1H-NMR(400.0 MHz, CDC13): 1-150: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4929 (3.7); 8.4809 (3.8); 7.2617 (25.3); 7.1664 (0.9); 7.1610 (0.7); 7.1454 (1.7); 7.1402 (0.6); 7.1297 (0.7); 7.1245 (1.0); 7.1089 (0.5); 7.0144 (1.3); 7.0025 (2.6); 6.9905 (1.3); 6.7778 (2.8); 6.7609 (2.9); 6.7569 (2.5); 6.7527 (0.6); 6.7399 (2.3); 5.2982δ = 8.4929 (3.7); 8.4809 (3.8); 7.2617 (25.3); 7.1664 (0.9); 7.1610 (0.7); 7.1454 (1.7); 7.1402 (0.6); 7.1297 (0.7); 7.1245 (1.0); 7.1089 (0.5); 7.0144 (1.3); 7.0025 (2.6); 6.9905 (1.3); 6.7778 (2.8); 6.7609 (2.9); 6.7569 (2.5); 6.7527 (0.6); 6.7399 (2.3); 5.2982
(1.5); 3.8529 (1.2); 3.7785 (16.0); 2.4456 (11.0); 2.3317 (1.4); -0.0002 (9.6) (1.5); 3.8529 (1.2); 3.7785 (16.0); 2.4456 (11.0); 2.3317 (1.4); -0.0002 (9.6)
1-151 : 1H-NMR(400.0 MHz, CDC13): 1-151: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4261 (4.9); 8.4142 (5.0); 7.2601 (20.9); 7.1714 (0.8); 7.1552 (1.4); 7.1521 (1.4); 7.1501 (1.3); 7.1393 (0.6); 7.1341 (1.7); 7.1326 (1.3); 7.0842 (1.0); 7.0801 (2.5); 7.0746 (1.4); 7.0660 (0.6); 7.0636 (0.8); 7.0618 (1.5); 7.0591 (1.5); 7.0545 (1.0); 6.9642δ = 8.4261 (4.9); 8.4142 (5.0); 7.2601 (20.9); 7.1714 (0.8); 7.1552 (1.4); 7.1521 (1.4); 7.1501 (1.3); 7.1393 (0.6); 7.1341 (1.7); 7.1326 (1.3); 7.0842 (1.0); 7.0801 (2.5); 7.0746 (1.4); 7.0660 (0.6); 7.0636 (0.8); 7.0618 (1.5); 7.0591 (1.5); 7.0545 (1.0); 6.9642
(1.4) ; 6.9522 (2.7); 6.9403 (1.4); 4.2824 (1.6); 4.2654 (2.1); 4.2478 (1.7); 3.0127 (1.7); 2.9952 (2.2); 2.9782 (1.6); 2.3673 (13.8);(1.4); 6.9522 (2.7); 6.9403 (1.4); 4.2824 (1.6); 4.2654 (2.1); 4.2478 (1.7); 3.0127 (1.7); 2.9952 (2.2); 2.9782 (1.6); 2.3673 (13.8);
2.0831 (16.0); 1.5561 (2.6); -0.0002 (7.6) 2.0831 (16.0); 1.5561 (2.6); -0.0002 (7.6)
1-152: 1H-NMR(400.0 MHz, CDC13): 1-152: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4519 (3.7); 8.4400 (3.9); 7.5182 (1.4); 7.2594 (247.3); 7.1814 (1.0); 7.1624 (1.9); 7.1601 (1.5); 7.1442 (2.1); 7.0872 (2.5); 7.0841 (3.0); 7.0688 (2.2); 7.0643 (1.9); 7.0516 (0.6); 7.0013 (1.2); 6.9953 (1.4); 6.9893 (2.2); 6.9773 (1.1); 5.2985 (1.2); 4.2609δ = 8.4519 (3.7); 8.4400 (3.9); 7.5182 (1.4); 7.2594 (247.3); 7.1814 (1.0); 7.1624 (1.9); 7.1601 (1.5); 7.1442 (2.1); 7.0872 (2.5); 7.0841 (3.0); 7.0688 (2.2); 7.0643 (1.9); 7.0516 (0.6); 7.0013 (1.2); 6.9953 (1.4); 6.9893 (2.2); 6.9773 (1.1); 5.2985 (1.2); 4.2609
(1.5) ; 4.2477 (1.8); 4.2437 (1.2); 4.2339 (1.7); 3.6819 (0.7); 3.6668 (1.2); 3.6555 (1.1); 3.6395 (0.6); 2.9472 (16.0); 2.3577(1.5); 4.2477 (1.8); 4.2437 (1.2); 4.2339 (1.7); 3.6819 (0.7); 3.6668 (1.2); 3.6555 (1.1); 3.6395 (0.6); 2.9472 (16.0); 2.3577
(14.3); 1.6779 (1.5); 0.0080 (2.4); -0.0002 (88.1); -0.0085 (2.6) (14.3); 1.6779 (1.5); 0.0080 (2.4); -0.0002 (88.1); -0.0085 (2.6)
1-069: 1H-NMR(400.0 MHz, CDC13): 1-069: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4708 (2.7); 8.4589 (2.7); 7.2622 (12.6); 7.0946 (0.8); 7.0747 (2.2); 7.0551 (1.9); 7.0472 (1.1); 7.0428 (2.4); 7.0388 (1.9); 7.0302 (1.4); 7.0269 (1.9); 7.0220 (1.1); 7.0106 (0.8); 7.0074 (0.8); 7.0056 (0.7); 7.0025 (0.6); 6.9902 (1.1); 6.9783 (2.0); 6.9716 (1.4); 6.9672 (2.2); 6.9642 (1.3); 6.9525 (0.9); 6.9493 (1.0); 6.9481 (1.0); 6.9449 (0.8); 5.2977 (1.7); 3.8473 (15.0); 2.3036δ = 8.4708 (2.7); 8.4589 (2.7); 7.2622 (12.6); 7.0946 (0.8); 7.0747 (2.2); 7.0551 (1.9); 7.0472 (1.1); 7.0428 (2.4); 7.0388 (1.9); 7.0302 (1.4); 7.0269 (1.9); 7.0220 (1.1); 7.0106 (0.8); 7.0074 (0.8); 7.0056 (0.7); 7.0025 (0.6); 6.9902 (1.1); 6.9783 (2.0); 6.9716 (1.4); 6.9672 (2.2); 6.9642 (1.3); 6.9525 (0.9); 6.9493 (1.0); 6.9481 (1.0); 6.9449 (0.8); 5.2977 (1.7); 3.8473 (15.0); 2.3036
(16.0); -0.0002 (7.2) (16.0); -0.0002 (7.2)
1-154: 'H-NMR(400.0 MHz, CDC13):  1-154: 'H-NMR (400.0 MHz, CDC13):
δ= 8.2916 (13.9); 7.5476 (4.4); 7.5470 (4.3); 7.2603 (42.8); 7.1489 (3.3); 7.1435 (1.3); 7.1324 (1.7); 7.1269 (5.9); 7.1206 (0.8); 7.0777 (0.9); 7.0715 (6.0); 7.0660 (1.6); 7.0549 (1.3); 7.0495 (3.4); 4.1303 (1.3); 4.1124 (1.3); 3.9118 (16.0); 2.0431 (5.9);δ = 8.2916 (13.9); 7.5476 (4.4); 7.5470 (4.3); 7.2603 (42.8); 7.1489 (3.3); 7.1435 (1.3); 7.1324 (1.7); 7.1269 (5.9); 7.1206 (0.8); 7.0777 (0.9); 7.0715 (6.0); 7.0660 (1.6); 7.0549 (1.3); 7.0495 (3.4); 4.1303 (1.3); 4.1124 (1.3); 3.9118 (16.0); 2.0431 (5.9);
1.5470 (14.5); 1.2761 (1.7); 1.2583 (3.5); 1.2404 (1.7); 0.0079 (0.6); -0.0002 (17.3) 1.5470 (14.5); 1.2761 (1.7); 1.2583 (3.5); 1.2404 (1.7); 0.0079 (0.6); -0.0002 (17.3)
1-155: 1H-NMR(400.0 MHz, de-DMSO): 1-155: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6287 (10.9); 7.2440 (1.5); 7.2250 (3.5); 7.2056 (2.5); 7.1243 (1.2); 7.1057 (1.8); 7.0876 (0.7); 7.0304 (3.5); 7.0120 (2.9); 3.9030 (1.0); 3.8108 (16.0); 3.3245 (54.0); 2.7319 (0.9); 2.7130 (3.0); 2.6940 (3.1); 2.6750 (1.3); 2.5059 (59.4); 2.5016 (77.6);δ = 8.6287 (10.9); 7.2440 (1.5); 7.2250 (3.5); 7.2056 (2.5); 7.1243 (1.2); 7.1057 (1.8); 7.0876 (0.7); 7.0304 (3.5); 7.0120 (2.9); 3.9030 (1.0); 3.8108 (16.0); 3.3245 (54.0); 2.7319 (0.9); 2.7130 (3.0); 2.6940 (3.1); 2.6750 (1.3); 2.5059 (59.4); 2.5016 (77.6);
2.4973 (56.8); 2.3286 (0.4); 2.3245 (0.3); 1.0666 (3.3); 1.0477 (7.4); 1.0287 (3.2); -0.0001 (0.8) 2.4973 (56.8); 2.3286 (0.4); 2.3245 (0.3); 1.0666 (3.3); 1.0477 (7.4); 1.0287 (3.2); -0.0001 (0.8)
1-156: 1H-NMR(400.0 MHz, de-DMSO): 1-156: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2509 (11.1); 7.4247 (1.3); 7.4179 (1.3); 7.4032 (1.3); 7.3965 (1.3); 7.1731 (0.6); 7.1663 (0.6); 7.1514 (1.2); 7.1447 (1.1); 7.1298 (0.7); 7.1231 (0.7); 6.8870 (1.3); 6.8724 (1.4); 6.8647 (1.2); 6.8501 (1.1); 3.9032 (0.8); 3.8115 (16.0); 3.7811 (13.0); 3.3263 (62.6); 2.6712 (0.4); 2.5065 (57.9); 2.5022 (75.5); 2.4978 (54.7); 2.3288 (0.4); 2.3243 (0.3); 2.2531 (12.9); -0.0002 (0.7) 1-044: 1H-NMR(400.0 MHz, de-DMSO): δ = 8.2509 (11.1); 7.4247 (1.3); 7.4179 (1.3); 7.4032 (1.3); 7.3965 (1.3); 7.1731 (0.6); 7.1663 (0.6); 7.1514 (1.2); 7.1447 (1.1); 7.1298 (0.7); 7.1231 (0.7); 6.8870 (1.3); 6.8724 (1.4); 6.8647 (1.2); 6.8501 (1.1); 3.9032 (0.8); 3.8115 (16.0); 3.7811 (13.0); 3.3263 (62.6); 2.6712 (0.4); 2.5065 (57.9); 2.5022 (75.5); 2.4978 (54.7); 2.3288 (0.4); 2.3243 (0.3); 2.2531 (12.9); -0.0002 (0.7) 1-044: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5219 (6.2); 8.5100 (6.3); 7.2446 (1.6); 7.2327 (3.8); 7.2207 (1.7); 7.2072 (1.3); 7.1835 (0.8); 7.0042 (1.8); 6.9983 (1.6); 6.9922 (2.0); 6.9775 (2.0); 3.9032 (1.2); 3.7697 (16.0); 3.3259 (71.9); 2.6709 (0.5); 2.5063 (66.4); 2.5022 (84.7); 2.4984 (62.4);δ = 8.5219 (6.2); 8.5100 (6.3); 7.2446 (1.6); 7.2327 (3.8); 7.2207 (1.7); 7.2072 (1.3); 7.1835 (0.8); 7.0042 (1.8); 6.9983 (1.6); 6.9922 (2.0); 6.9775 (2.0); 3.9032 (1.2); 3.7697 (16.0); 3.3259 (71.9); 2.6709 (0.5); 2.5063 (66.4); 2.5022 (84.7); 2.4984 (62.4);
2.3292 (0.5); 2.2995 (15.6); -0.0002 (1.8) 2.3292 (0.5); 2.2995 (15.6); -0.0002 (1.8)
1-069: 1H-NMR(400.0 MHz, de-DMSO): 1-069: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5440 (6.5); 8.5320 (6.6); 7.2678 (1.1); 7.2487 (3.7); 7.2379 (3.3); 7.2277 (2.6); 7.1690 (1.6); 7.1665 (1.6); 7.1490 (1.0); 7.1466 (1.1); 7.0313 (1.7); 7.0269 (3.2); 7.0223 (2.0); 7.0058 (1.7); 6.9863 (1.4); 3.9031 (1.4); 3.7954 (16.0); 3.3264 (75.4); 2.6709 (0.4); 2.5062 (61.7); 2.5019 (79.1); 2.4975 (56.5); 2.3324 (0.3); 2.3289 (0.4); 2.2754 (15.9); -0.0003 (1.7) 1-157: 'H-NMR(400.0 MHz, de-DMSO): δ = 8.5440 (6.5); 8.5320 (6.6); 7.2678 (1.1); 7.2487 (3.7); 7.2379 (3.3); 7.2277 (2.6); 7.1690 (1.6); 7.1665 (1.6); 7.1490 (1.0); 7.1466 (1.1); 7.0313 (1.7); 7.0269 (3.2); 7.0223 (2.0); 7.0058 (1.7); 6.9863 (1.4); 3.9031 (1.4); 3.7954 (16.0); 3.3264 (75.4); 2.6709 (0.4); 2.5062 (61.7); 2.5019 (79.1); 2.4975 (56.5); 2.3324 (0.3); 2.3289 (0.4); 2.2754 (15.9); -0.0003 (1.7) 1-157: 'H-NMR (400.0 MHz, de-DMSO):
δ= 8.2617 (10.8); 7.3452 (0.5); 7.3237 (1.0); 7.3187 (0.6); 7.3020 (0.7); 7.2971 (1.0); 7.2758 (0.5); 7.0739 (0.6); 7.0682 (0.6); 7.0554 (0.6); 7.0494 (0.7); 7.0464 (0.7); 7.0404 (0.6); 7.0276 (0.6); 7.0219 (0.6); 6.8623 (0.4); 6.8563 (0.5); 6.8527 (0.7); 6.8485 (0.6); 6.8409 (0.5); 6.8355 (0.5); 6.8309 (0.6); 6.8261 (0.5); 3.9033 (1.2); 3.8699 (0.4); 3.8166 (16.0); 3.7902 (0.3); 3.7676 (12.9); 3.3244 (47.4); 2.6711 (0.4); 2.5241 (1.1); 2.5104 (27.6); 2.5064 (54.9); 2.5020 (71.3); 2.4975 (51.0); 2.3288 (0.4); 2.2885δ = 8.2617 (10.8); 7.3452 (0.5); 7.3237 (1.0); 7.3187 (0.6); 7.3020 (0.7); 7.2971 (1.0); 7.2758 (0.5); 7.0739 (0.6); 7.0682 (0.6); 7.0554 (0.6); 7.0494 (0.7); 7.0464 (0.7); 7.0404 (0.6); 7.0276 (0.6); 7.0219 (0.6); 6.8623 (0.4); 6.8563 (0.5); 6.8527 (0.7); 6.8485 (0.6); 6.8409 (0.5); 6.8355 (0.5); 6.8309 (0.6); 6.8261 (0.5); 3.9033 (1.2); 3.8699 (0.4); 3.8166 (16.0); 3.7902 (0.3); 3.7676 (12.9); 3.3244 (47.4); 2.6711 (0.4); 2.5241 (1.1); 2.5104 (27.6); 2.5064 (54.9); 2.5020 (71.3); 2.4975 (51.0); 2.3288 (0.4); 2.2885
(0.4); 2.2732 (12.7); -0.0002 (1.9) (0.4); 2.2732 (12.7); -0.0002 (1.9)
1-159: 'H-NMR(400.0 MHz, de-DMSO):  1-159: 'H-NMR (400.0 MHz, de-DMSO):
δ= 8.2854 (11.0); 7.3570 (0.5); 7.3354 (1.2); 7.3308 (0.7); 7.3091 (1.1); 7.2875 (0.6); 7.1025 (0.6); 7.0971 (0.6); 7.0839 (0.6); 7.0754 (0.8); 7.0691 (0.7); 7.0562 (0.6); 7.0507 (0.6); 6.8764 (0.8); 6.8662 (0.6); 6.8550 (0.7); 3.9034 (0.8); 3.8203 (16.0); 3.8025 (14.0); 3.3257 (73.4); 2.7281 (0.8); 2.7091 (2.6); 2.6901 (2.7); 2.6712 (1.3); 2.5062 (64.9); 2.5022 (83.2); 2.3289 (0.5);δ = 8.2854 (11.0); 7.3570 (0.5); 7.3354 (1.2); 7.3308 (0.7); 7.3091 (1.1); 7.2875 (0.6); 7.1025 (0.6); 7.0971 (0.6); 7.0839 (0.6); 7.0754 (0.8); 7.0691 (0.7); 7.0562 (0.6); 7.0507 (0.6); 6.8764 (0.8); 6.8662 (0.6); 6.8550 (0.7); 3.9034 (0.8); 3.8203 (16.0); 3.8025 (14.0); 3.3257 (73.4); 2.7281 (0.8); 2.7091 (2.6); 2.6901 (2.7); 2.6712 (1.3); 2.5062 (64.9); 2.5022 (83.2); 2.3289 (0.5);
1.0744 (2.9); 1.0555 (6.4); 1.0365 (2.8); -0.0001 (0.8) 1.0744 (2.9); 1.0555 (6.4); 1.0365 (2.8); -0.0001 (0.8)
1-160: 1H-NMR(400.0 MHz, de-DMSO): 1-160: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6320 (16.0); 8.1946 (8.2); 7.3157 (0.7); 7.3090 (5.8); 7.2876 (7.1); 7.2807 (0.9); 7.0790 (0.9); 7.0722 (7.0); 7.0507 (5.9); 4.1537 (1.6); 4.1355 (5.1); 4.1173 (5.2); 4.0991 (1.8); 3.9030 (1.4); 3.3265 (143.9); 2.6711 (0.7); 2.6669 (0.6); 2.5063 (101.4);δ = 8.6320 (16.0); 8.1946 (8.2); 7.3157 (0.7); 7.3090 (5.8); 7.2876 (7.1); 7.2807 (0.9); 7.0790 (0.9); 7.0722 (7.0); 7.0507 (5.9); 4.1537 (1.6); 4.1355 (5.1); 4.1173 (5.2); 4.0991 (1.8); 3.9030 (1.4); 3.3265 (143.9); 2.6711 (0.7); 2.6669 (0.6); 2.5063 (101.4);
2.5020 (131.7); 2.4976 (96.0); 2.3329 (0.6); 2.3287 (0.7); 1.4229 (5.9); 1.4047 (12.5); 1.3866 (5.8); -0.0002 (1.6) 2.5020 (131.7); 2.4976 (96.0); 2.3329 (0.6); 2.3287 (0.7); 1.4229 (5.9); 1.4047 (12.5); 1.3866 (5.8); -0.0002 (1.6)
1-161 : 1H-NMR(400.0 MHz, CDC13): 1-161: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4846 (7.3); 8.4726 (7.4); 7.9059 (0.5); 7.8904 (0.6); 7.8849 (1.1); 7.8693 (1.0); 7.8631 (0.7); 7.8476 (0.6); 7.2618 (25.9); 7.0520 (2.2); 7.0401 (4.2); 7.0281 (2.1); 6.8932 (0.6); 6.8907 (0.6); 6.8798 (0.5); 6.8772 (0.8); 6.8737 (0.7); 6.8711 (1.2); 6.8693 (1.0); 6.8672 (0.9); 6.8660 (0.9); 6.8578 (0.5); 6.8516 (0.6); 6.8496 (0.8); 6.8448 (0.9); 6.8420 (0.9); 6.8361 (0.6); 6.8208 (0.8);δ = 8.4846 (7.3); 8.4726 (7.4); 7.9059 (0.5); 7.8904 (0.6); 7.8849 (1.1); 7.8693 (1.0); 7.8631 (0.7); 7.8476 (0.6); 7.2618 (25.9); 7.0520 (2.2); 7.0401 (4.2); 7.0281 (2.1); 6.8932 (0.6); 6.8907 (0.6); 6.8798 (0.5); 6.8772 (0.8); 6.8737 (0.7); 6.8711 (1.2); 6.8693 (1.0); 6.8672 (0.9); 6.8660 (0.9); 6.8578 (0.5); 6.8516 (0.6); 6.8496 (0.8); 6.8448 (0.9); 6.8420 (0.9); 6.8361 (0.6); 6.8208 (0.8);
6.8148 (0.6); 3.8071 (16.0); 3.7880 (0.9); 2.6383 (8.8); 2.6361 (8.7); 2.2936 (0.9); 1.5661 (1.3); -0.0002 (10.0) 6.8148 (0.6); 3.8071 (16.0); 3.7880 (0.9); 2.6383 (8.8); 2.6361 (8.7); 2.2936 (0.9); 1.5661 (1.3); -0.0002 (10.0)
1-162: 1H-NMR(400.0 MHz, CDC13): 1-162: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.6567 (1.4); 8.6519 (1.4); 8.2384 (1.5); 8.2325 (1.4); 8.2169 (1.5); 8.2110 (1.5); 7.2600 (36.1); 7.0999 (0.6); 7.0986 (0.6); 7.0807 (1.6); 7.0794 (1.6); 7.0614 (1.5); 7.0601 (1.5); 7.0399 (1.0); 7.0367 (1.3); 7.0350 (1.4); 7.0319 (1.4); 7.0155 (1.4); 7.0123δ = 8.6567 (1.4); 8.6519 (1.4); 8.2384 (1.5); 8.2325 (1.4); 8.2169 (1.5); 8.2110 (1.5); 7.2600 (36.1); 7.0999 (0.6); 7.0986 (0.6); 7.0807 (1.6); 7.0794 (1.6); 7.0614 (1.5); 7.0601 (1.5); 7.0399 (1.0); 7.0367 (1.3); 7.0350 (1.4); 7.0319 (1.4); 7.0155 (1.4); 7.0123
(2.3) ; 7.0090 (2.2); 7.0078 (2.1); 7.0039 (2.4); 6.9821 (1.6); 6.9808 (1.5); 6.9466 (1.1); 6.9434 (1.2); 6.9423 (1.2); 6.9391 (0.9); 6.9276 (0.9); 6.9240 (1.0); 6.9199 (0.7); 5.2981 (2.7); 3.8959 (16.0); 3.8422 (13.2); 2.3077 (12.4); 1.5474 (5.9); 0.0079 (0.7); -(2.3); 7.0090 (2.2); 7.0078 (2.1); 7.0039 (2.4); 6.9821 (1.6); 6.9808 (1.5); 6.9466 (1.1); 6.9434 (1.2); 6.9423 (1.2); 6.9391 (0.9); 6.9276 (0.9); 6.9240 (1.0); 6.9199 (0.7); 5.2981 (2.7); 3.8959 (16.0); 3.8422 (13.2); 2.3077 (12.4); 1.5474 (5.9); 0.0079 (0.7); -
0.0002 (13.1); -0.0085 (0.5) 0.0002 (13.1); -0.0085 (0.5)
1-163: !H-NMR^OCl MHz, de-DMSO): 1-163 :! H-NMR ^ OCl MHz, de-DMSO):
δ= 8.5366 (15.6); 8.5207 (16.0); 7.2604 (4.2); 7.2445 (9.3); 7.2362 (1.9); 7.2285 (4.1); 7.2141 (1.9); 7.2111 (1.9); 7.2054 (2.1); 7.2029 (1.9); 7.1804 (1.5); 7.1720 (1.5); 7.1188 (1.1); 7.0976 (1.2); 7.0896 (2.7); 7.0684 (2.8); 7.0609 (2.1); 7.0396 (2.0); 7.0206 (1.6); 7.0183 (1.6); 7.0119 (1.4); 7.0098 (1.4); 6.9904 (2.2); 6.9822 (2.0); 6.9635 (0.8); 6.9609 (0.8); 6.9548 (0.8); 6.9524 (0.8); 4.1848 (2.9); 4.1606 (4.6); 4.1365 (3.0); 3.3234 (10.7); 2.9341 (2.4); 2.9104 (4.3); 2.8850 (3.2); 2.5686 (0.9); 2.5439 (2.6);δ = 8.5366 (15.6); 8.5207 (16.0); 7.2604 (4.2); 7.2445 (9.3); 7.2362 (1.9); 7.2285 (4.1); 7.2141 (1.9); 7.2111 (1.9); 7.2054 (2.1); 7.2029 (1.9); 7.1804 (1.5); 7.1720 (1.5); 7.1188 (1.1); 7.0976 (1.2); 7.0896 (2.7); 7.0684 (2.8); 7.0609 (2.1); 7.0396 (2.0); 7.0206 (1.6); 7.0183 (1.6); 7.0119 (1.4); 7.0098 (1.4); 6.9904 (2.2); 6.9822 (2.0); 6.9635 (0.8); 6.9609 (0.8); 6.9548 (0.8); 6.9524 (0.8); 4.1848 (2.9); 4.1606 (4.6); 4.1365 (3.0); 3.3234 (10.7); 2.9341 (2.4); 2.9104 (4.3); 2.8850 (3.2); 2.5686 (0.9); 2.5439 (2.6);
2.5147 (7.9); 2.5086 (13.6); 2.5025 (18.0); 2.4965 (13.6); 2.4713 (0.8); 0.0108 (0.4); -0.0001 (12.7); -0.0112 (0.4) 2.5147 (7.9); 2.5086 (13.6); 2.5025 (18.0); 2.4965 (13.6); 2.4713 (0.8); 0.0108 (0.4); -0.0001 (12.7); -0.0112 (0.4)
1-164: 1H-NMR(400.0 MHz, CDC13): 1-164: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.2459 (16.0); 7.2596 (19.8); 7.1861 (0.7); 7.1724 (1.0); 7.1691 (1.6); 7.1635 (1.8); 7.1597 (1.1); 7.1514 (4.7); 7.1502 (4.6); 7.1421 (6.5); 7.1361 (2.5); 7.1342 (1.9); 7.1290 (1.7); 7.1247 (2.0); 7.1194 (1.1); 7.1164 (2.0); 7.1003 (0.5); 4.0382 (9.6); 4.0352δ = 8.2459 (16.0); 7.2596 (19.8); 7.1861 (0.7); 7.1724 (1.0); 7.1691 (1.6); 7.1635 (1.8); 7.1597 (1.1); 7.1514 (4.7); 7.1502 (4.6); 7.1421 (6.5); 7.1361 (2.5); 7.1342 (1.9); 7.1290 (1.7); 7.1247 (2.0); 7.1194 (1.1); 7.1164 (2.0); 7.1003 (0.5); 4.0382 (9.6); 4.0352
(9.9); 4.0323 (4.1); 1.5449 (3.3); -0.0002 (7.8) (9.9); 4.0323 (4.1); 1.5449 (3.3); -0.0002 (7.8)
1-165: 1H-NMR(400.0 MHz, CDC13): 1-165: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4442 (4.4); 8.4323 (4.5); 7.2605 (24.4); 7.1662 (0.7); 7.1642 (1.0); 7.1600 (0.5); 7.1475 (1.7); 7.1449 (2.1); 7.1430 (1.8); 7.1315 (0.9); 7.1268 (2.2); 7.1255 (1.8); 7.1219 (0.6); 7.0790 (2.0); 7.0751 (3.0); 7.0698 (0.9); 7.0606 (1.6); 7.0574 (2.5); 7.0543 (2.0); 7.0446 (0.7); 7.0398 (1.5); 7.0348 (0.5); 7.0219 (0.7); 6.9580 (1.6); 6.9460 (3.1); 6.9341 (1.6); 5.2974 (0.7); 3.9312 (16.0); 3.8529 (0.5); 1.6833 (0.5); 1.6698 (0.9); 1.6561 (0.6); 1.6486 (0.6); 1.5624 (1.1); 1.0092 (1.1); 1.0047 (1.4); 0.9961 (2.0); 0.9926δ = 8.4442 (4.4); 8.4323 (4.5); 7.2605 (24.4); 7.1662 (0.7); 7.1642 (1.0); 7.1600 (0.5); 7.1475 (1.7); 7.1449 (2.1); 7.1430 (1.8); 7.1315 (0.9); 7.1268 (2.2); 7.1255 (1.8); 7.1219 (0.6); 7.0790 (2.0); 7.0751 (3.0); 7.0698 (0.9); 7.0606 (1.6); 7.0574 (2.5); 7.0543 (2.0); 7.0446 (0.7); 7.0398 (1.5); 7.0348 (0.5); 7.0219 (0.7); 6.9580 (1.6); 6.9460 (3.1); 6.9341 (1.6); 5.2974 (0.7); 3.9312 (16.0); 3.8529 (0.5); 1.6833 (0.5); 1.6698 (0.9); 1.6561 (0.6); 1.6486 (0.6); 1.5624 (1.1); 1.0092 (1.1); 1.0047 (1.4); 0.9961 (2.0); 0.9926
(1.6) ; 0.9826 (1.0); 0.9735 (0.6); 0.9656 (0.7); 0.9620 (1.1); 0.9549 (1.1); 0.9529 (1.3); 0.9519 (1.3); 0.9495 (1.3); 0.9475 (1.0);(1.6); 0.9826 (1.0); 0.9735 (0.6); 0.9656 (0.7); 0.9620 (1.1); 0.9549 (1.1); 0.9529 (1.3); 0.9519 (1.3); 0.9495 (1.3); 0.9475 (1.0);
0.9410 (1.2); 0.9374 (0.6); 0.9334 (1.4); 0.9304 (1.2); 0.9275 (1.2); 0.9194 (0.6); 0.9132 (0.6); -0.0002 (8.7) 0.9410 (1.2); 0.9374 (0.6); 0.9334 (1.4); 0.9304 (1.2); 0.9275 (1.2); 0.9194 (0.6); 0.9132 (0.6); -0.0002 (8.7)
1-166: 1H-NMR(400.0 MHz, CDC13): 1-166: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.2891 (10.9); 7.2595 (66.3); 7.0999 (0.5); 7.0810 (1.0); 7.0788 (1.4); 7.0620 (1.0); 7.0598 (1.3); 7.0365 (0.8); 7.0319 (1.4); 7.0288 (1.5); 7.0166 (1.2); 7.0138 (3.0); 7.0100 (2.6); 7.0076 (0.9); 6.9958 (0.8); 6.9706 (0.6); 6.9496 (1.0); 6.9454 (1.2); 6.9421 (0.9); 6.9305 (0.8); 6.9266 (1.3); 6.9229 (0.7); 5.9352 (0.8); 3.9498 (0.8); 3.9430 (16.0); 3.7263 (2.8); 1.6976 (0.5); 1.6825 (1.1); 1.2263 (1.5); 1.2090 (1.5); 1.1474 (0.6); 1.1301 (0.6); 0.9873 (6.3); 0.9792 (1.4); 0.9745 (2.4); 0.9719 (1.8); 0.9682 (1.9); 0.9654δ = 8.2891 (10.9); 7.2595 (66.3); 7.0999 (0.5); 7.0810 (1.0); 7.0788 (1.4); 7.0620 (1.0); 7.0598 (1.3); 7.0365 (0.8); 7.0319 (1.4); 7.0288 (1.5); 7.0166 (1.2); 7.0138 (3.0); 7.0100 (2.6); 7.0076 (0.9); 6.9958 (0.8); 6.9706 (0.6); 6.9496 (1.0); 6.9454 (1.2); 6.9421 (0.9); 6.9305 (0.8); 6.9266 (1.3); 6.9229 (0.7); 5.9352 (0.8); 3.9498 (0.8); 3.9430 (16.0); 3.7263 (2.8); 1.6976 (0.5); 1.6825 (1.1); 1.2263 (1.5); 1.2090 (1.5); 1.1474 (0.6); 1.1301 (0.6); 0.9873 (6.3); 0.9792 (1.4); 0.9745 (2.4); 0.9719 (1.8); 0.9682 (1.9); 0.9654
(2.4) ; 0.9608 (1.2); 0.0079 (0.7); -0.0002 (25.2); -0.0085 (0.8) (2.4); 0.9608 (1.2); 0.0079 (0.7); -0.0002 (25.2); -0.0085 (0.8)
1-167: 1H-NMR(400.0 MHz, de-DMSO): 1-167: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5546 (6.8); 8.5426 (7.0); 7.3339 (1.9); 7.3294 (3.6); 7.3249 (2.0); 7.2658 (1.8); 7.2538 (3.4); 7.2419 (1.7); 7.0569 (7.7); 7.0524 (7.5); 3.9032 (0.9); 3.8059 (16.0); 3.3274 (94.6); 2.6750 (0.4); 2.6712 (0.5); 2.6664 (0.4); 2.5244 (1.3); 2.5107 (34.5); 2.5066 (70.1); 2.5021 (92.4); 2.4977 (66.0); 2.4934 (31.6); 2.3332 (0.4); 2.3289 (0.5); 2.3243 (0.4); 2.2834 (15.9); -0.0002 (0.8) 1-168: 1H-NMR(400.1 MHz, de-DMSO): δ = 8.5546 (6.8); 8.5426 (7.0); 7.3339 (1.9); 7.3294 (3.6); 7.3249 (2.0); 7.2658 (1.8); 7.2538 (3.4); 7.2419 (1.7); 7.0569 (7.7); 7.0524 (7.5); 3.9032 (0.9); 3.8059 (16.0); 3.3274 (94.6); 2.6750 (0.4); 2.6712 (0.5); 2.6664 (0.4); 2.5244 (1.3); 2.5107 (34.5); 2.5066 (70.1); 2.5021 (92.4); 2.4977 (66.0); 2.4934 (31.6); 2.3332 (0.4); 2.3289 (0.5); 2.3243 (0.4); 2.2834 (15.9); -0.0002 (0.8) 1-168: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.5248 (6.2); 8.5128 (6.3); 7.2386 (1.7); 7.2267 (3.2); 7.2148 (1.7); 7.1824 (0.8); 7.1653 (1.3); 7.1464 (1.8); 7.1234 (1.3); 7.1201 (1.4); 7.1005 (1.6); 7.0809 (1.7); 7.0635 (0.9); 7.0599 (0.8); 6.9223 (0.9); 6.9190 (1.0); 6.9025 (1.6); 6.8993 (1.6); 6.8831 (0.8); 6.8796 (0.7); 3.7872 (16.0); 3.5111 (2.3); 2.5061 (7.7); 2.5021 (10.2); 2.4982 (7.8); 2.2825 (15.6); 1.2329 (0.4); -0.0012δ = 8.5248 (6.2); 8.5128 (6.3); 7.2386 (1.7); 7.2267 (3.2); 7.2148 (1.7); 7.1824 (0.8); 7.1653 (1.3); 7.1464 (1.8); 7.1234 (1.3); 7.1201 (1.4); 7.1005 (1.6); 7.0809 (1.7); 7.0635 (0.9); 7.0599 (0.8); 6.9223 (0.9); 6.9190 (1.0); 6.9025 (1.6); 6.8993 (1.6); 6.8831 (0.8); 6.8796 (0.7); 3.7872 (16.0); 3.5111 (2.3); 2.5061 (7.7); 2.5021 (10.2); 2.4982 (7.8); 2.2825 (15.6); 1.2329 (0.4); -0.0012
(1 -3) (1 -3)
1-169: 1H-NMR(400.1 MHz, de-DMSO): 1-169: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.7129 (10.2); 7.1178 (2.9); 7.1128 (1.2); 7.1011 (1.6); 7.0960 (5.5); 7.0896 (0.9); 7.0555 (0.9); 7.0492 (5.4); 7.0439 (1.5); 7.0323 (1.2); 7.0273 (2.9); 3.7895 (16.0); 3.6782 (14.6); 3.3496 (3.1); 2.5060 (7.0); 2.5018 (9.2); 2.4975 (6.8); 2.2272 (14.5);δ = 8.7129 (10.2); 7.1178 (2.9); 7.1128 (1.2); 7.1011 (1.6); 7.0960 (5.5); 7.0896 (0.9); 7.0555 (0.9); 7.0492 (5.4); 7.0439 (1.5); 7.0323 (1.2); 7.0273 (2.9); 3.7895 (16.0); 3.6782 (14.6); 3.3496 (3.1); 2.5060 (7.0); 2.5018 (9.2); 2.4975 (6.8); 2.2272 (14.5);
2.0754 (0.4); -0.0009 (0.9) 2.0754 (0.4); -0.0009 (0.9)
1-170: 1H-NMR(400.1 MHz, de-DMSO): 1-170: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.5421 (6.2); 8.5301 (6.4); 8.3055 (1.6); 8.2956 (1.6); 8.2937 (1.6); 7.6455 (0.8); 7.6411 (0.8); 7.6257 (1.6); 7.6217 (1.5); 7.6067 (0.9); 7.6022 (0.9); 7.2459 (1.7); 7.2340 (3.2); 7.2221 (1.6); 7.1056 (1.3); 7.0934 (1.4); 7.0872 (1.3); 7.0750 (1.2); 6.9259 (2.3); 6.9056 (2.1); 3.8015 (16.0); 3.6439 (0.4); 3.3439 (25.5); 2.5030 (11.0); 2.4992 (8.4); 2.2672 (15.7); 2.1749 (0.4); 1.2348δ = 8.5421 (6.2); 8.5301 (6.4); 8.3055 (1.6); 8.2956 (1.6); 8.2937 (1.6); 7.6455 (0.8); 7.6411 (0.8); 7.6257 (1.6); 7.6217 (1.5); 7.6067 (0.9); 7.6022 (0.9); 7.2459 (1.7); 7.2340 (3.2); 7.2221 (1.6); 7.1056 (1.3); 7.0934 (1.4); 7.0872 (1.3); 7.0750 (1.2); 6.9259 (2.3); 6.9056 (2.1); 3.8015 (16.0); 3.6439 (0.4); 3.3439 (25.5); 2.5030 (11.0); 2.4992 (8.4); 2.2672 (15.7); 2.1749 (0.4); 1.2348
(1.7) ; 0.9397 (0.3); -0.0002 (0.8) 1-171 : 'H-NMR(400.1 MHz, de-DMSO): (1.7); 0.9397 (0.3); -0.0002 (0.8) 1-171: 'H-NMR (400.1 MHz, de-DMSO):
δ= 7.8328 (0.9); 7.8298 (0.9); 7.8126 (1.0); 7.8086 (1.3); 7.8035 (1.1); 7.7864 (0.9); 7.7833 (1.0); 7.7420 (1.8); 7.7395 (1.8); 7.7301 (2.0); 7.2316 (0.8); 7.2272 (0.8); 7.2038 (1.5); 7.1811 (0.9); 7.1715 (1.0); 7.1629 (1.1); 7.1597 (1.1); 7.1513 (1.7); 7.1429 (1.0); 7.1397 (1.0); 7.1312 (0.8); 7.0083 (1.8); 7.0011 (1.9); 6.9956 (2.4); 6.9874 (1.3); 6.9809 (2.5); 3.7564 (16.0); 3.5956 (0.7); 3.3631 (11.1); 2.5069 (10.3); 2.5029 (13.2); 2.4989 (10.1); 2.2952 (15.6); 2.1212 (0.8); 2.0761 (0.4); 1.2336 (0.4); -0.0009 (1.2) 1-172: Ή-ΝΜϋ^ΟΟ.Ο MHz, CDC13): δ = 7.8328 (0.9); 7.8298 (0.9); 7.8126 (1.0); 7.8086 (1.3); 7.8035 (1.1); 7.7864 (0.9); 7.7833 (1.0); 7.7420 (1.8); 7.7395 (1.8); 7.7301 (2.0); 7.2316 (0.8); 7.2272 (0.8); 7.2038 (1.5); 7.1811 (0.9); 7.1715 (1.0); 7.1629 (1.1); 7.1597 (1.1); 7.1513 (1.7); 7.1429 (1.0); 7.1397 (1.0); 7.1312 (0.8); 7.0083 (1.8); 7.0011 (1.9); 6.9956 (2.4); 6.9874 (1.3); 6.9809 (2.5); 3.7564 (16.0); 3.5956 (0.7); 3.3631 (11.1); 2.5069 (10.3); 2.5029 (13.2); 2.4989 (10.1); 2.2952 (15.6); 2.1212 (0.8); 2.0761 (0.4); 1.2336 (0.4); -0.0009 (1.2) 1-172: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, CDC13):
δ= 8.4580 (0.7); 8.2809 (10.7); 7.4644 (0.8); 7.4465 (2.1); 7.4413 (1.5); 7.4367 (3.4); 7.4299 (4.7); 7.4211 (0.7); 7.3938 (2.2); 7.3911 (1.2); 7.3845 (1.9); 7.3758 (1.2); 7.3693 (1.1); 7.2593 (18.2); 7.1378 (0.8); 7.1213 (1.4); 7.1184 (1.7); 7.1157 (1.3); 7.1004 (2.1); 7.0582 (0.9); 7.0562 (1.2); 7.0471 (2.6); 7.0445 (3.6); 7.0394 (2.3); 7.0305 (0.9); 7.0261 (2.0); 7.0236 (1.7); 5.2961δ = 8.4580 (0.7); 8.2809 (10.7); 7.4644 (0.8); 7.4465 (2.1); 7.4413 (1.5); 7.4367 (3.4); 7.4299 (4.7); 7.4211 (0.7); 7.3938 (2.2); 7.3911 (1.2); 7.3845 (1.9); 7.3758 (1.2); 7.3693 (1.1); 7.2593 (18.2); 7.1378 (0.8); 7.1213 (1.4); 7.1184 (1.7); 7.1157 (1.3); 7.1004 (2.1); 7.0582 (0.9); 7.0562 (1.2); 7.0471 (2.6); 7.0445 (3.6); 7.0394 (2.3); 7.0305 (0.9); 7.0261 (2.0); 7.0236 (1.7); 5.2961
(4.0); 3.8543 (16.0); 3.8147 (0.5); 1.5537 (0.8); 1.2576 (0.5); -0.0002 (6.6) (4.0); 3.8543 (16.0); 3.8147 (0.5); 1.5537 (0.8); 1.2576 (0.5); -0.0002 (6.6)
1-173: 1H-NMR(400.0 MHz, de-DMSO): 1-173: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5542 (7.3); 8.5422 (7.6); 7.2652 (1.9); 7.2532 (3.6); 7.2412 (1.9); 7.2184 (0.9); 7.2166 (1.3); 7.2123 (0.6); 7.1982 (3.1); 7.1955 (1.8); 7.1828 (1.0); 7.1790 (2.4); 7.1183 (0.6); 7.1153 (1.3); 7.1122 (0.9); 7.1015 (0.6); 7.0969 (1.7); 7.0920 (0.6); 7.0785 (0.7); 7.0531 (2.8); 7.0499 (3.4); 7.0447 (0.9); 7.0343 (1.4); 7.0320 (2.6); 7.0292 (2.1); 4.0836 (16.0); 4.0625 (0.9); 4.0208 (0.5); 3.3208 (0.5); 2.5192 (0.6); 2.5105 (6.1); 2.5060 (12.5); 2.5015 (16.9); 2.4970 (11.9); 2.4924 (5.6); 1.9882 (2.2); 1.3568 (0.8);δ = 8.5542 (7.3); 8.5422 (7.6); 7.2652 (1.9); 7.2532 (3.6); 7.2412 (1.9); 7.2184 (0.9); 7.2166 (1.3); 7.2123 (0.6); 7.1982 (3.1); 7.1955 (1.8); 7.1828 (1.0); 7.1790 (2.4); 7.1183 (0.6); 7.1153 (1.3); 7.1122 (0.9); 7.1015 (0.6); 7.0969 (1.7); 7.0920 (0.6); 7.0785 (0.7); 7.0531 (2.8); 7.0499 (3.4); 7.0447 (0.9); 7.0343 (1.4); 7.0320 (2.6); 7.0292 (2.1); 4.0836 (16.0); 4.0625 (0.9); 4.0208 (0.5); 3.3208 (0.5); 2.5192 (0.6); 2.5105 (6.1); 2.5060 (12.5); 2.5015 (16.9); 2.4970 (11.9); 2.4924 (5.6); 1.9882 (2.2); 1.3568 (0.8);
1.1922 (0.6); 1.1744 (1.2); 1.1566 (0.6); -0.0002 (0.8) 1.1922 (0.6); 1.1744 (1.2); 1.1566 (0.6); -0.0002 (0.8)
1-174: 1H-NMR(400.0 MHz, CDC13): 1-174: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4363 (5.6); 8.4243 (5.7); 7.2624 (13.7); 7.2189 (0.6); 7.2153 (0.8); 7.2027 (0.9); 7.1980 (1.9); 7.1946 (1.4); 7.1898 (0.6); 7.1833 (1.2); 7.1796 (2.4); 7.1775 (1.7); 7.1735 (0.7); 7.1556 (0.6); 7.1515 (1.1); 7.1484 (1.2); 7.1341 (2.2); 7.1317 (3.5); 7.1274δ = 8.4363 (5.6); 8.4243 (5.7); 7.2624 (13.7); 7.2189 (0.6); 7.2153 (0.8); 7.2027 (0.9); 7.1980 (1.9); 7.1946 (1.4); 7.1898 (0.6); 7.1833 (1.2); 7.1796 (2.4); 7.1775 (1.7); 7.1735 (0.7); 7.1556 (0.6); 7.1515 (1.1); 7.1484 (1.2); 7.1341 (2.2); 7.1317 (3.5); 7.1274
(3.6) ; 7.1216 (0.7); 7.1190 (0.7); 7.1149 (1.4); 7.1108 (2.1); 7.1074 (1.4); 6.9991 (1.7); 6.9871 (3.1); 6.9752 (1.6); 5.2976 (4.3);(3.6); 7.1216 (0.7); 7.1190 (0.7); 7.1149 (1.4); 7.1108 (2.1); 7.1074 (1.4); 6.9991 (1.7); 6.9871 (3.1); 6.9752 (1.6); 5.2976 (4.3);
4.2748 (16.0); 2.9119 (7.4); 2.8996 (7.3); 1.5781 (0.8); -0.0002 (5.2) 4.2748 (16.0); 2.9119 (7.4); 2.8996 (7.3); 1.5781 (0.8); -0.0002 (5.2)
1-175: 1H-NMR(400.0 MHz, CDC13): 1-175: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4142 (5.5); 8.4022 (5.6); 7.2624 (16.6); 7.1794 (0.7); 7.1745 (1.0); 7.1686 (0.5); 7.1634 (0.6); 7.1577 (3.7); 7.1533 (5.2); 7.1492 (1.0); 7.1380 (2.0); 7.1361 (2.7); 7.1312 (0.8); 7.1210 (0.5); 7.1164 (0.8); 7.0870 (0.7); 7.0823 (1.0); 7.0769 (0.6); 7.0679 (0.7); 7.0655 (0.9); 6.9753 (1.6); 6.9634 (3.0); 6.9515 (1.5); 5.2977 (3.9); 3.8953 (1.2); 3.8868 (16.0); 3.1056 (0.5); 3.0504δ = 8.4142 (5.5); 8.4022 (5.6); 7.2624 (16.6); 7.1794 (0.7); 7.1745 (1.0); 7.1686 (0.5); 7.1634 (0.6); 7.1577 (3.7); 7.1533 (5.2); 7.1492 (1.0); 7.1380 (2.0); 7.1361 (2.7); 7.1312 (0.8); 7.1210 (0.5); 7.1164 (0.8); 7.0870 (0.7); 7.0823 (1.0); 7.0769 (0.6); 7.0679 (0.7); 7.0655 (0.9); 6.9753 (1.6); 6.9634 (3.0); 6.9515 (1.5); 5.2977 (3.9); 3.8953 (1.2); 3.8868 (16.0); 3.1056 (0.5); 3.0504
(12.3); 2.9799 (12.4); 1.5829 (0.6); -0.0002 (6.1) (12.3); 2.9799 (12.4); 1.5829 (0.6); -0.0002 (6.1)
1-177: 1H-NMR(400.0 MHz, CDC13): 1-177: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4353 (0.7); 8.3220 (0.5); 8.3171 (11.8); 8.2232 (1.8); 8.2159 (1.8); 7.2627 (17.0); 7.2329 (0.8); 7.2256 (0.7); 7.2126 (1.0); 7.2109 (1.0); 7.2052 (0.9); 7.2035 (1.0); 7.1906 (0.9); 7.1832 (0.9); 6.9524 (1.1); 6.9512 (1.0); 6.9422 (1.1); 6.9409 (1.0); 6.9303 (0.9); 6.9290 (0.9); 6.9201 (0.9); 6.9189 (0.8); 5.2987 (1.2); 3.8494 (16.0); 3.8278 (0.6); 3.7355 (1.2); 2.3282 (0.9); 2.3209δ = 8.4353 (0.7); 8.3220 (0.5); 8.3171 (11.8); 8.2232 (1.8); 8.2159 (1.8); 7.2627 (17.0); 7.2329 (0.8); 7.2256 (0.7); 7.2126 (1.0); 7.2109 (1.0); 7.2052 (0.9); 7.2035 (1.0); 7.1906 (0.9); 7.1832 (0.9); 6.9524 (1.1); 6.9512 (1.0); 6.9422 (1.1); 6.9409 (1.0); 6.9303 (0.9); 6.9290 (0.9); 6.9201 (0.9); 6.9189 (0.8); 5.2987 (1.2); 3.8494 (16.0); 3.8278 (0.6); 3.7355 (1.2); 2.3282 (0.9); 2.3209
(15.7); 2.2902 (0.7); 2.2889 (0.7); 1.5771 (1.6); -0.0002 (6.2) (15.7); 2.2902 (0.7); 2.2889 (0.7); 1.5771 (1.6); -0.0002 (6.2)
1-082: 1H-NMR(400.0 MHz, CDC13): 1-082: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4566 (1.7); 8.4447 (1.7); 8.4259 (5.0); 8.4140 (5.0); 7.2604 (24.5); 7.1686 (0.9); 7.1665 (0.9); 7.1558 (0.6); 7.1518 (1.0); 7.1482 (1.6); 7.1454 (2.1); 7.1351 (0.6); 7.1291 (2.0); 7.0642 (3.5); 7.0590 (1.0); 7.0556 (0.9); 7.0511 (1.2); 7.0462 (2.9); 7.0435δ = 8.4566 (1.7); 8.4447 (1.7); 8.4259 (5.0); 8.4140 (5.0); 7.2604 (24.5); 7.1686 (0.9); 7.1665 (0.9); 7.1558 (0.6); 7.1518 (1.0); 7.1482 (1.6); 7.1454 (2.1); 7.1351 (0.6); 7.1291 (2.0); 7.0642 (3.5); 7.0590 (1.0); 7.0556 (0.9); 7.0511 (1.2); 7.0462 (2.9); 7.0435
(1.7) ; 7.0393 (1.3); 7.0351 (0.6); 7.0318 (0.7); 7.0275 (0.9); 6.9558 (1.4); 6.9438 (2.7); 6.9319 (1.4); 4.2470 (1.6); 4.2335 (3.1); 4.2200 (2.0); 4.2071 (1.1); 4.1925 (0.6); 3.7961 (1.8); 3.7825 (3.3); 3.7690 (1.6); 3.7522 (0.6); 3.7376 (1.3); 3.7228 (0.5); 3.3367(1.7); 7.0393 (1.3); 7.0351 (0.6); 7.0318 (0.7); 7.0275 (0.9); 6.9558 (1.4); 6.9438 (2.7); 6.9319 (1.4); 4.2470 (1.6); 4.2335 (3.1); 4.2200 (2.0); 4.2071 (1.1); 4.1925 (0.6); 3.7961 (1.8); 3.7825 (3.3); 3.7690 (1.6); 3.7522 (0.6); 3.7376 (1.3); 3.7228 (0.5); 3.3367
(16.0); 3.2396 (5.1); 2.3373 (2.4); 2.3312 (13.9); 2.2270 (4.2); -0.0002 (9.1) (16.0); 3.2396 (5.1); 2.3373 (2.4); 2.3312 (13.9); 2.2270 (4.2); -0.0002 (9.1)
1-178: 1H-NMR(400.0 MHz, CDC13): 1-178: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4667 (5.2); 8.4547 (5.3); 7.5637 (1.4); 7.5602 (2.0); 7.5550 (0.7); 7.5419 (3.0); 7.5398 (3.1); 7.5335 (0.6); 7.5024 (1.8); 7.4972 (0.7); 7.4840 (2.9); 7.4801 (1.5); 7.4680 (0.9); 7.4639 (1.6); 7.4135 (0.8); 7.4103 (1.2); 7.4069 (0.7); 7.3970 (0.6); 7.3919 (1.4); 7.3867 (0.5); 7.3738 (0.6); 7.2598 (19.9); 7.2130 (0.9); 7.2088 (0.5); 7.1969 (1.4); 7.1934 (2.5); 7.1818 (1.0); 7.1764 (3.1); 7.1667 (3.4); 7.1620 (4.2); 7.1559 (0.9); 7.1453 (1.6); 7.1411 (1.0); 7.1106 (0.8); 7.1067 (1.0); 7.1021 (0.6); 7.0946 (0.7); 7.0921 (0.8); 7.0893 (1.6); 7.0833 (0.5); 7.0721 (0.6); 6.9954 (1.7); 6.9834 (3.0); 6.9714 (1.6); 5.2971 (1.2); 2.4132 (16.0); 2.0877 (0.6);δ = 8.4667 (5.2); 8.4547 (5.3); 7.5637 (1.4); 7.5602 (2.0); 7.5550 (0.7); 7.5419 (3.0); 7.5398 (3.1); 7.5335 (0.6); 7.5024 (1.8); 7.4972 (0.7); 7.4840 (2.9); 7.4801 (1.5); 7.4680 (0.9); 7.4639 (1.6); 7.4135 (0.8); 7.4103 (1.2); 7.4069 (0.7); 7.3970 (0.6); 7.3919 (1.4); 7.3867 (0.5); 7.3738 (0.6); 7.2598 (19.9); 7.2130 (0.9); 7.2088 (0.5); 7.1969 (1.4); 7.1934 (2.5); 7.1818 (1.0); 7.1764 (3.1); 7.1667 (3.4); 7.1620 (4.2); 7.1559 (0.9); 7.1453 (1.6); 7.1411 (1.0); 7.1106 (0.8); 7.1067 (1.0); 7.1021 (0.6); 7.0946 (0.7); 7.0921 (0.8); 7.0893 (1.6); 7.0833 (0.5); 7.0721 (0.6); 6.9954 (1.7); 6.9834 (3.0); 6.9714 (1.6); 5.2971 (1.2); 2.4132 (16.0); 2.0877 (0.6);
2.0434 (0.6); 1.5602 (0.8); 1.2581 (0.7); -0.0002 (8.5) 2.0434 (0.6); 1.5602 (0.8); 1.2581 (0.7); -0.0002 (8.5)
1-179: 1H-NMR(400.0 MHz, CDC13): 1-179: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.2575 (0.6); 8.2308 (8.9); 7.5182 (0.8); 7.2593 (150.7); 7.1766 (0.8); 7.1744 (1.2); 7.1702 (0.6); 7.1603 (0.8); 7.1562 (2.9); 7.1533 (1.7); 7.1410 (1.1); 7.1372 (2.5); 7.1356 (1.8); 7.0845 (0.6); 7.0812 (1.3); 7.0781 (1.0); 7.0679 (0.5); 7.0629 (1.6); 7.0576 (0.6); 7.0461 (3.2); 7.0427 (3.6); 7.0373 (0.8); 7.0250 (2.4); 7.0220 (1.9); 6.9953 (0.9); 4.2436 (2.0); 4.2302 (3.9); 4.2167 (2.2); 3.7904 (2.0); 3.7769 (3.4); 3.7636 (1.7); 3.3366 (16.0); 3.3158 (0.8); 3.2386 (0.8); 2.3385 (14.3); 2.3055 (0.8); 2.2327 (0.6);δ = 8.2575 (0.6); 8.2308 (8.9); 7.5182 (0.8); 7.2593 (150.7); 7.1766 (0.8); 7.1744 (1.2); 7.1702 (0.6); 7.1603 (0.8); 7.1562 (2.9); 7.1533 (1.7); 7.1410 (1.1); 7.1372 (2.5); 7.1356 (1.8); 7.0845 (0.6); 7.0812 (1.3); 7.0.781 (1.0); 7.0679 (0.5); 7.0629 (1.6); 7.0576 (0.6); 7.0461 (3.2); 7.0427 (3.6); 7.0373 (0.8); 7.0250 (2.4); 7.0220 (1.9); 6.9953 (0.9); 4.2436 (2.0); 4.2302 (3.9); 4.2167 (2.2); 3.7904 (2.0); 3.7769 (3.4); 3.7636 (1.7); 3.3366 (16.0); 3.3158 (0.8); 3.2386 (0.8); 2.3385 (14.3); 2.3055 (0.8); 2.2327 (0.6);
1.5665 (1.7); 0.0079 (2.2); -0.0002 (61.8); -0.0085 (1.7) 1.5665 (1.7); 0.0079 (2.2); -0.0002 (61.8); -0.0085 (1.7)
1-180: 1H-NMR(400.0 MHz, CDC13): 1-180: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.6970 (3.8); 7.2661 (0.5); 7.2653 (0.6); 7.2644 (0.8); 7.2636 (1.0); 7.2603 (30.9); 7.0057 (0.7); 6.9842 (1.0); 6.9807 (0.7); 6.9640 (0.9); 6.9593 (1.0); 6.9390 (0.8); 6.9112 (0.7); 6.9055 (0.8); 6.8931 (0.7); 6.8873 (0.8); 6.8846 (0.7); 6.8788 (0.8); 6.8664 (0.6); 6.8607 (0.8); 6.8223 (0.6); 6.8186 (0.6); 6.8165 (0.6); 6.8124 (0.9); 6.8086 (0.6); 6.8064 (0.5); 6.8028 (0.6); 6.8007 (0.5);δ = 8.6970 (3.8); 7.2661 (0.5); 7.2653 (0.6); 7.2644 (0.8); 7.2636 (1.0); 7.2603 (30.9); 7.0057 (0.7); 6.9842 (1.0); 6.9807 (0.7); 6.9640 (0.9); 6.9593 (1.0); 6.9390 (0.8); 6.9112 (0.7); 6.9055 (0.8); 6.8931 (0.7); 6.8873 (0.8); 6.8846 (0.7); 6.8788 (0.8); 6.8664 (0.6); 6.8607 (0.8); 6.8223 (0.6); 6.8186 (0.6); 6.8165 (0.6); 6.8124 (0.9); 6.8086 (0.6); 6.8064 (0.5); 6.8028 (0.6); 6.8007 (0.5);
6.7909 (0.7); 5.2985 (0.6); 3.8519 (16.0); 2.3313 (15.0); -0.0002 (13.2) 6.7909 (0.7); 5.2985 (0.6); 3.8519 (16.0); 2.3313 (15.0); -0.0002 (13.2)
1-181 : 1H-NMR(400.0 MHz, CDC13): 1-181: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.2956 (10.4); 7.2614 (15.5); 7.1386 (2.8); 7.1334 (1.0); 7.1220 (1.2); 7.1167 (4.1); 7.1102 (0.5); 7.0357 (0.6); 7.0292 (4.3); 7.0238 (1.2); 7.0125 (1.0); 7.0072 (2.8); 3.8513 (16.0); 2.7512 (0.8); 2.7320 (2.7); 2.7129 (2.8); 2.6939 (0.8); 1.1453 (3.0);δ = 8.2956 (10.4); 7.2614 (15.5); 7.1386 (2.8); 7.1334 (1.0); 7.1220 (1.2); 7.1167 (4.1); 7.1102 (0.5); 7.0357 (0.6); 7.0292 (4.3); 7.0238 (1.2); 7.0125 (1.0); 7.0072 (2.8); 3.8513 (16.0); 2.7512 (0.8); 2.7320 (2.7); 2.7129 (2.8); 2.6939 (0.8); 1.1453 (3.0);
1.1263 (6.7); 1.1072 (2.8); -0.0002 (5.7) 1.1263 (6.7); 1.1072 (2.8); -0.0002 (5.7)
1-182: 1H-NMR(400.0 MHz, CDC13): 1-182: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.2965 (11.6); 7.5380 (4.3); 7.2606 (22.8); 7.1544 (2.0); 7.1491 (0.8); 7.1417 (2.0); 7.1374 (1.0); 7.1321 (2.3); 7.1248 (0.9); 7.1194 (2.3); 6.9001 (2.4); 6.8945 (0.7); 6.8832 (0.8); 6.8785 (3.7); 6.8732 (0.8); 6.8619 (0.6); 6.8564 (1.9); 4.1302 (1.2); 4.1124 (1.2); 3.8980 (16.0); 2.0427 (5.5); 1.5607 (1.2); 1.2758 (1.6); 1.2580 (3.2); 1.2401 (1.5); -0.0002 (9.0) 1-087: 'H-NMR(400.0 MHz, CDC13): δ = 8.2965 (11.6); 7.5380 (4.3); 7.2606 (22.8); 7.1544 (2.0); 7.1491 (0.8); 7.1417 (2.0); 7.1374 (1.0); 7.1321 (2.3); 7.1248 (0.9); 7.1194 (2.3); 6.9001 (2.4); 6.8945 (0.7); 6.8832 (0.8); 6.8785 (3.7); 6.8732 (0.8); 6.8619 (0.6); 6.8564 (1.9); 4.1302 (1.2); 4.1124 (1.2); 3.8980 (16.0); 2.0427 (5.5); 1.5607 (1.2); 1.2758 (1.6); 1.2580 (3.2); 1.2401 (1.5); -0.0002 (9.0) 1-087: 'H-NMR (400.0 MHz, CDC13):
δ= 8.4682 (5.6); 8.4562 (5.7); 7.2614 (22.1); 7.1014 (1.8); 7.0960 (0.8); 7.0886 (1.9); 7.0845 (0.9); 7.0832 (0.9); 7.0790 (2.4); 7.0716 (0.9); 7.0662 (2.3); 6.9973 (1.8); 6.9853 (3.3); 6.9733 (1.7); 6.8804 (2.3); 6.8748 (0.7); 6.8635 (0.7); 6.8586 (3.4); 6.8534 (0.8); 6.8421 (0.6); 6.8366 (1.8); 3.8181 (15.8); 3.7871 (0.6); 3.7435 (0.7); 2.3079 (16.0); 2.2929 (0.6); 1.3334 (0.5); 1.2843δ = 8.4682 (5.6); 8.4562 (5.7); 7.2614 (22.1); 7.1014 (1.8); 7.0960 (0.8); 7.0886 (1.9); 7.0845 (0.9); 7.0832 (0.9); 7.0790 (2.4); 7.0716 (0.9); 7.0662 (2.3); 6.9973 (1.8); 6.9853 (3.3); 6.9733 (1.7); 6.8804 (2.3); 6.8748 (0.7); 6.8635 (0.7); 6.8586 (3.4); 6.8534 (0.8); 6.8421 (0.6); 6.8366 (1.8); 3.8181 (15.8); 3.7871 (0.6); 3.7435 (0.7); 2.3079 (16.0); 2.2929 (0.6); 1.3334 (0.5); 1.2843
(0.7); 1.2558 (0.6); -0.0002 (8.4) (0.7); 1.2558 (0.6); -0.0002 (8.4)
1-183: 1H-NMR(400.0 MHz, de-DMSO): 1-183: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6420 (11.0); 7.0915 (5.4); 7.0883 (5.4); 7.0724 (11.4); 3.9031 (1.9); 3.8003 (16.0); 3.3251 (72.5); 2.7391 (0.9); 2.7202 (3.0); 2.7011 (3.1); 2.6822 (1.0); 2.6755 (0.5); 2.6712 (0.6); 2.5061 (70.0); 2.5019 (89.8); 2.4975 (64.5); 2.3327 (0.4); 2.3285 (0.5);δ = 8.6420 (11.0); 7.0915 (5.4); 7.0883 (5.4); 7.0724 (11.4); 3.9031 (1.9); 3.8003 (16.0); 3.3251 (72.5); 2.7391 (0.9); 2.7202 (3.0); 2.7011 (3.1); 2.6822 (1.0); 2.6755 (0.5); 2.6712 (0.6); 2.5061 (70.0); 2.5019 (89.8); 2.4975 (64.5); 2.3327 (0.4); 2.3285 (0.5);
2.3244 (0.4); 1.0655 (3.4); 1.0466 (7.5); 1.0276 (3.2); -0.0002 (2.4) 2.3244 (0.4); 1.0655 (3.4); 1.0466 (7.5); 1.0276 (3.2); -0.0002 (2.4)
1-184: 1H-NMR(400.0 MHz, de-DMSO): 1-184: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5609 (6.1); 8.5489 (6.2); 7.2972 (0.6); 7.2817 (0.7); 7.2769 (1.3); 7.2615 (1.4); 7.2530 (1.8); 7.2411 (3.8); 7.2291 (1.6); 6.9503 (0.6); 6.9443 (0.6); 6.9287 (1.0); 6.9231 (1.1); 6.9079 (0.6); 6.8935 (1.5); 6.8738 (1.4); 6.8514 (0.9); 6.8462 (1.2); 6.8412 (0.7); 6.8268 (0.9); 6.8219 (1.2); 6.8164 (0.7); 3.9033 (1.5); 3.8286 (16.0); 3.3251 (62.9); 2.7286 (0.9); 2.7096 (3.0); 2.6906 (3.1); 2.6714 (1.4); 2.5240 (1.3); 2.5063 (61.2); 2.5020 (79.6); 2.4976 (57.6); 2.3329 (0.3); 2.3288 (0.5); 2.3243 (0.3); 1.0741δ = 8.5609 (6.1); 8.5489 (6.2); 7.2972 (0.6); 7.2817 (0.7); 7.2769 (1.3); 7.2615 (1.4); 7.2530 (1.8); 7.2411 (3.8); 7.2291 (1.6); 6.9503 (0.6); 6.9443 (0.6); 6.9287 (1.0); 6.9231 (1.1); 6.9079 (0.6); 6.8935 (1.5); 6.8738 (1.4); 6.8514 (0.9); 6.8462 (1.2); 6.8412 (0.7); 6.8268 (0.9); 6.8219 (1.2); 6.8164 (0.7); 3.9033 (1.5); 3.8286 (16.0); 3.3251 (62.9); 2.7286 (0.9); 2.7096 (3.0); 2.6906 (3.1); 2.6714 (1.4); 2.5240 (1.3); 2.5063 (61.2); 2.5020 (79.6); 2.4976 (57.6); 2.3329 (0.3); 2.3288 (0.5); 2.3243 (0.3); 1.0741
(3.3); 1.0552 (7.4); 1.0362 (3.2); -0.0002 (2.0) (3.3); 1.0552 (7.4); 1.0362 (3.2); -0.0002 (2.0)
1-185: 1H-NMR(400.0 MHz, de-DMSO): 1-185: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2785 (10.3); 7.2991 (0.5); 7.2835 (0.6); 7.2791 (1.0); 7.2636 (1.0); 7.2590 (0.7); 7.2434 (0.6); 6.9549 (0.4); 6.9489 (0.5); 6.9340 (0.8); 6.9280 (0.8); 6.9123 (0.4); 6.9071 (0.4); 6.8776 (1.1); 6.8578 (1.1); 6.8269 (0.7); 6.8218 (0.9); 6.8165 (0.6); 6.8023 (0.7); 6.7975 (0.9); 6.7920 (0.5); 3.9032 (1.4); 3.8160 (16.0); 3.8116 (13.4); 3.3238 (47.9); 2.7226 (0.6); 2.7036 (2.2); 2.6846 (2.3); 2.6756 (0.5); 2.6659 (0.9); 2.5240 (1.1); 2.5104 (25.1); 2.5062 (51.1); 2.5018 (67.1); 2.4973 (48.0); 2.4932 (23.1); 2.3285δ = 8.2785 (10.3); 7.2991 (0.5); 7.2835 (0.6); 7.2791 (1.0); 7.2636 (1.0); 7.2590 (0.7); 7.2434 (0.6); 6.9549 (0.4); 6.9489 (0.5); 6.9340 (0.8); 6.9280 (0.8); 6.9123 (0.4); 6.9071 (0.4); 6.8776 (1.1); 6.8578 (1.1); 6.8269 (0.7); 6.8218 (0.9); 6.8165 (0.6); 6.8023 (0.7); 6.7975 (0.9); 6.7920 (0.5); 3.9032 (1.4); 3.8160 (16.0); 3.8116 (13.4); 3.3238 (47.9); 2.7226 (0.6); 2.7036 (2.2); 2.6846 (2.3); 2.6756 (0.5); 2.6659 (0.9); 2.5240 (1.1); 2.5104 (25.1); 2.5062 (51.1); 2.5018 (67.1); 2.4973 (48.0); 2.4932 (23.1); 2.3285
(0.4); 1.0723 (2.4); 1.0534 (5.6); 1.0344 (2.4); -0.0002 (1.8) (0.4); 1.0723 (2.4); 1.0534 (5.6); 1.0344 (2.4); -0.0002 (1.8)
1-186: 1H-NMR(400.0 MHz, de-DMSO): 1-186: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2749 (10.8); 7.0869 (4.2); 7.0827 (4.2); 7.0672 (9.3); 3.9031 (1.3); 3.8166 (16.0); 3.7868 (13.4); 3.3278 (87.7); 2.7272 (0.7); 2.7083 (2.4); 2.6893 (2.5); 2.6706 (1.1); 2.5062 (54.8); 2.5019 (71.4); 2.4975 (51.4); 2.3286 (0.4); 1.0588 (2.7); 1.0400 (6.2);δ = 8.2749 (10.8); 7.0869 (4.2); 7.0827 (4.2); 7.0672 (9.3); 3.9031 (1.3); 3.8166 (16.0); 3.7868 (13.4); 3.3278 (87.7); 2.7272 (0.7); 2.7083 (2.4); 2.6893 (2.5); 2.6706 (1.1); 2.5062 (54.8); 2.5019 (71.4); 2.4975 (51.4); 2.3286 (0.4); 1.0588 (2.7); 1,0400 (6.2);
1.0209 (2.6); -0.0002 (0.9) 1.0209 (2.6); -0.0002 (0.9)
1-187: 1H-NMR(400.0 MHz, de-DMSO): 1-187: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2717 (11.5); 7.3043 (0.4); 7.2973 (3.6); 7.2926 (1.2); 7.2806 (1.3); 7.2758 (4.3); 7.2688 (0.5); 7.0503 (0.5); 7.0435 (4.2); 7.0388 (1.2); 7.0267 (1.2); 7.0220 (3.6); 7.0151 (0.3); 3.9031 (0.9); 3.8144 (16.0); 3.7988 (13.5); 3.3258 (70.4); 2.7159 (0.7); 2.6970 (2.4); 2.6779 (2.6); 2.6664 (0.5); 2.6592 (0.8); 2.5238 (1.1); 2.5062 (56.7); 2.5018 (73.4); 2.4974 (52.2); 2.3286 (0.4);δ = 8.2717 (11.5); 7.3043 (0.4); 7.2973 (3.6); 7.2926 (1.2); 7.2806 (1.3); 7.2758 (4.3); 7.2688 (0.5); 7.0503 (0.5); 7.0435 (4.2); 7.0388 (1.2); 7.0267 (1.2); 7.0220 (3.6); 7.0151 (0.3); 3.9031 (0.9); 3.8144 (16.0); 3.7988 (13.5); 3.3258 (70.4); 2.7159 (0.7); 2.6970 (2.4); 2.6779 (2.6); 2.6664 (0.5); 2.6592 (0.8); 2.5238 (1.1); 2.5062 (56.7); 2.5018 (73.4); 2.4974 (52.2); 2.3286 (0.4);
1.0642 (2.7); 1.0453 (6.0); 1.0263 (2.6); -0.0002 (0.6) 1.0642 (2.7); 1.0453 (6.0); 1.0263 (2.6); -0.0002 (0.6)
1-188: 1H-NMR(400.0 MHz, de-DMSO): 1-188: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6365 (14.2); 8.1539 (5.5); 7.3088 (0.4); 7.3016 (4.3); 7.2969 (1.4); 7.2850 (1.5); 7.2801 (5.3); 7.2732 (0.6); 7.0764 (0.6); 7.0695 (5.4); 7.0646 (1.6); 7.0529 (1.4); 7.0480 (4.5); 7.0409 (0.5); 3.9030 (1.0); 3.8509 (16.0); 3.3263 (98.9); 2.6756 (0.4); 2.6709 (0.5); 2.6664 (0.4); 2.5241 (1.2); 2.5103 (31.8); 2.5062 (65.4); 2.5018 (86.8); 2.4974 (62.4); 2.3332 (0.4); 2.3285 (0.5);δ = 8.6365 (14.2); 8.1539 (5.5); 7.3088 (0.4); 7.3016 (4.3); 7.2969 (1.4); 7.2850 (1.5); 7.2801 (5.3); 7.2732 (0.6); 7.0764 (0.6); 7.0695 (5.4); 7.0646 (1.6); 7.0529 (1.4); 7.0480 (4.5); 7.0409 (0.5); 3.9030 (1.0); 3.8509 (16.0); 3.3263 (98.9); 2.6756 (0.4); 2.6709 (0.5); 2.6664 (0.4); 2.5241 (1.2); 2.5103 (31.8); 2.5062 (65.4); 2.5018 (86.8); 2.4974 (62.4); 2.3332 (0.4); 2.3285 (0.5);
2.3238 (0.4); -0.0002 (0.5) 2.3238 (0.4); -0.0002 (0.5)
1-189: 1H-NMR(400.0 MHz, de-DMSO): 1-189: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6141 (16.0); 8.1734 (8.3); 7.2510 (2.1); 7.2324 (4.9); 7.2129 (3.6); 7.1371 (1.8); 7.1187 (2.6); 7.1003 (1.0); 7.0587 (4.0); 7.0556 (5.1); 7.0375 (4.0); 4.1533 (1.6); 4.1352 (5.2); 4.1170 (5.3); 4.0989 (1.7); 3.9030 (1.2); 3.3249 (102.5); 2.6752 (0.4); 2.6708 (0.6); 2.6662 (0.4); 2.5237 (1.6); 2.5101 (41.8); 2.5061 (83.5); 2.5016 (109.0); 2.4972 (77.8); 2.4930 (37.4); 2.3326 (0.4);δ = 8.6141 (16.0); 8.1734 (8.3); 7.2510 (2.1); 7.2324 (4.9); 7.2129 (3.6); 7.1371 (1.8); 7.1187 (2.6); 7.1003 (1.0); 7.0587 (4.0); 7.0556 (5.1); 7.0375 (4.0); 4.1533 (1.6); 4.1352 (5.2); 4.1170 (5.3); 4.0989 (1.7); 3.9030 (1.2); 3.3249 (102.5); 2.6752 (0.4); 2.6708 (0.6); 2.6662 (0.4); 2.5237 (1.6); 2.5101 (41.8); 2.5061 (83.5); 2.5016 (109.0); 2.4972 (77.8); 2.4930 (37.4); 2.3326 (0.4);
2.3283 (0.6); 2.3237 (0.4); 1.4248 (6.0); 1.4066 (12.7); 1.3884 (5.8); -0.0002 (1.4) 2.3283 (0.6); 2.3237 (0.4); 1.4248 (6.0); 1.4066 (12.7); 1.3884 (5.8); -0.0002 (1.4)
1-190: 1H-NMR(400.0 MHz, de-DMSO): 1-190: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6233 (14.4); 8.2193 (6.1); 7.2515 (1.3); 7.2473 (0.6); 7.2330 (3.2); 7.2135 (2.4); 7.1400 (1.2); 7.1373 (0.8); 7.1216 (1.7); 7.1032 (0.6); 7.0486 (2.6); 7.0454 (3.3); 7.0274 (2.7); 4.5067 (0.4); 4.4900 (1.0); 4.4734 (1.4); 4.4568 (1.0); 4.4403 (0.4); 3.9029 (1.0); 3.3224 (47.3); 2.6751 (0.4); 2.6705 (0.5); 2.6660 (0.3); 2.5238 (1.2); 2.5103 (31.6); 2.5059 (65.0); 2.5015 (85.5); 2.4969δ = 8.6233 (14.4); 8.2193 (6.1); 7.2515 (1.3); 7.2473 (0.6); 7.2330 (3.2); 7.2135 (2.4); 7.1400 (1.2); 7.1373 (0.8); 7.1216 (1.7); 7.1032 (0.6); 7.0486 (2.6); 7.0454 (3.3); 7.0274 (2.7); 4.5067 (0.4); 4,400 (1.0); 4.4734 (1.4); 4.4568 (1.0); 4.4403 (0.4); 3.9029 (1.0); 3.3224 (47.3); 2.6751 (0.4); 2.6705 (0.5); 2.6660 (0.3); 2.5238 (1.2); 2.5103 (31.6); 2.5059 (65.0); 2.5015 (85.5); 2.4969
(60.2); 2.4925 (28.1); 2.3325 (0.3); 2.3282 (0.5); 2.3237 (0.4); 1.4538 (16.0); 1.4372 (15.8); 0.9360 (0.4); -0.0002 (1.7) (60.2); 2.4925 (28.1); 2.3325 (0.3); 2.3282 (0.5); 2.3237 (0.4); 1.4538 (16.0); 1.4372 (15.8); 0.9360 (0.4); -0.0002 (1.7)
1-191 : 1H-NMR(400.0 MHz, de-DMSO): 1-191: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6139 (10.8); 8.2056 (6.0); 7.2530 (1.4); 7.2345 (3.3); 7.2150 (2.4); 7.1360 (1.2); 7.1176 (1.8); 7.0992 (0.6); 7.0515 (2.8); 7.0485 (3.4); 7.0304 (2.8); 4.5023 (0.4); 4.4856 (1.0); 4.4690 (1.4); 4.4524 (1.1); 4.4359 (0.4); 3.9030 (1.1); 3.3245 (61.0); 2.6752 (0.3); 2.6707 (0.5); 2.6662 (0.3); 2.5239 (1.2); 2.5104 (32.3); 2.5061 (65.1); 2.5017 (84.6); 2.4972 (59.8); 2.4930 (28.3);δ = 8.6139 (10.8); 8.2056 (6.0); 7.2530 (1.4); 7.2345 (3.3); 7.2150 (2.4); 7.1360 (1.2); 7.1176 (1.8); 7.0992 (0.6); 7.0515 (2.8); 7.0485 (3.4); 7.0304 (2.8); 4.5023 (0.4); 4.4856 (1.0); 4.4690 (1.4); 4.4524 (1.1); 4.4359 (0.4); 3.9030 (1.1); 3.3245 (61.0); 2.6752 (0.3); 2.6707 (0.5); 2.6662 (0.3); 2.5239 (1.2); 2.5104 (32.3); 2.5061 (65.1); 2.5017 (84.6); 2.4972 (59.8); 2.4930 (28.3);
2.3330 (0.4); 2.3282 (0.5); 2.3236 (0.3); 2.2494 (0.3); 1.4519 (16.0); 1.4353 (15.8); 1.1750 (0.3); -0.0001 (1.5) 2.3330 (0.4); 2.3282 (0.5); 2.3236 (0.3); 2.2494 (0.3); 1.4519 (16.0); 1.4353 (15.8); 1.1750 (0.3); -0.0001 (1.5)
1-192: !H-NMR^OCl MHz, de-DMSO): 1-192 :! H-NMR ^ OCl MHz, de-DMSO):
δ= 8.6225 (16.0); 7.2592 (1.1); 7.2504 (1.2); 7.2285 (1.4); 7.2198 (1.5); 7.1949 (1.1); 7.1864 (1.1); 7.1149 (0.8); 7.0936 (0.9); 7.0858 (2.0); 7.0645 (2.0); 7.0572 (1.6); 7.0358 (1.4); 7.0203 (1.2); 7.0117 (1.1); 6.9905 (1.7); 6.9820 (1.4); 6.9610 (0.6); 6.9527 (0.6); 4.1792 (2.1); 4.1554 (3.3); 4.1311 (2.1); 3.3217 (41.2); 2.9427 (1.8); 2.9190 (3.1); 2.8935 (2.3); 2.5661 (0.7); 2.5407 (2.0); 2.5137 (13.5); 2.5077 (24.1); 2.5017 (31.5); 2.4957 (22.2); 2.4899 (10.8); 2.4688 (0.7); 2.0751 (1.8); 0.0108 (0.7); -0.0001 (20.7);δ = 8.6225 (16.0); 7.2592 (1.1); 7.2504 (1.2); 7.2285 (1.4); 7.2198 (1.5); 7.1949 (1.1); 7.1864 (1.1); 7.1149 (0.8); 7.0936 (0.9); 7.0858 (2.0); 7.0645 (2.0); 7.0572 (1.6); 7.0358 (1.4); 7.0203 (1.2); 7.0117 (1.1); 6.9905 (1.7); 6.9820 (1.4); 6.9610 (0.6); 6.9527 (0.6); 4.1792 (2.1); 4.1554 (3.3); 4.1311 (2.1); 3.3217 (41.2); 2.9427 (1.8); 2.9190 (3.1); 2.8935 (2.3); 2.5661 (0.7); 2.5407 (2.0); 2.5137 (13.5); 2.5077 (24.1); 2.5017 (31.5); 2.4957 (22.2); 2.4899 (10.8); 2.4688 (0.7); 2.0751 (1.8); 0.0108 (0.7); -0.0001 (20.7);
-0.0111 (0.7) -0.0111 (0.7)
1-193: 1H-NMR(400.1 MHz, de-DMSO): 1-193: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.5484 (6.3); 8.5365 (6.4); 7.2460 (1.7); 7.2340 (3.3); 7.2221 (1.7); 7.0420 (3.0); 7.0217 (4.2); 6.9238 (4.9); 6.9034 (3.6); 3.7647 (16.0); 3.3281 (35.1); 3.3043 (0.5); 2.8899 (0.3); 2.5059 (16.2); 2.5018 (21.4); 2.4978 (16.0); 2.2747 (0.4); 2.2529 (15.9);δ = 8.5484 (6.3); 8.5365 (6.4); 7.2460 (1.7); 7.2340 (3.3); 7.2221 (1.7); 7.0420 (3.0); 7.0217 (4.2); 6.9238 (4.9); 6.9034 (3.6); 3.7647 (16.0); 3.3281 (35.1); 3.3043 (0.5); 2,888 (0.3); 2.5059 (16.2); 2.5018 (21.4); 2.4978 (16.0); 2.2747 (0.4); 2.2529 (15.9);
2.2124 (12.5); 1.2578 (0.4); 1.2349 (3.2); 0.9394 (0.4); 0.9227 (0.4); 0.8534 (0.4); -0.0002 (3.9) 2.2124 (12.5); 1.2578 (0.4); 1.2349 (3.2); 0.9394 (0.4); 0.9227 (0.4); 0.8534 (0.4); -0.0002 (3.9)
1-194: 1H-NMR(400.1 MHz, de-DMSO): 1-194: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 7.8206 (1.3); 7.7913 (3.7); 7.7763 (3.9); 7.1727 (1.2); 7.1633 (1.7); 7.1528 (1.9); 7.1419 (1.6); 7.1334 (1.2); 7.1260 (0.9); 7.1021 (1.3); 7.0779 (7.7); 7.0594 (11.3); 3.7547 (16.0); 3.6980 (0.9); 3.3212 (12.8); 2.5023 (20.9); 2.2884 (1.8); 2.2684 (15.9); 2.0750 (0.7); 1.2985 (0.4); 1.2575 (0.5); 1.2339 (1.2); -0.0002 (2.6) 1-195: Ή-ΝΜϋ^ΟΟ.Ι MHz, de-DMSO): δ = 7.8206 (1.3); 7.7913 (3.7); 7.7763 (3.9); 7.1727 (1.2); 7.1633 (1.7); 7.1528 (1.9); 7.1419 (1.6); 7.1334 (1.2); 7.1260 (0.9); 7.1021 (1.3); 7.0779 (7.7); 7.0594 (11.3); 3.7547 (16.0); 3.6980 (0.9); 3.3212 (12.8); 2.5023 (20.9); 2.2884 (1.8); 2.2684 (15.9); 2.0750 (0.7); 1.2985 (0.4); 1.2575 (0.5); 1.2339 (1.2); -0.0002 (2.6) 1-195: Ή-ΝΜϋ ^ ΟΟ.Ι MHz, de-DMSO):
δ= 8.4815 (4.3); 8.4784 (5.4); 8.4756 (5.4); 8.4725 (4.8); 8.4652 (4.8); 8.4622 (5.7); 8.4590 (5.3); 8.4561 (4.6); 8.0260 (4.8); 8.0228 (3.4); 8.0020 (7.3); 7.9985 (11.1); 7.9951 (6.8); 7.9717 (5.9); 7.9657 (5.9); 7.9481 (6.3); 7.9421 (6.2); 7.9203 (2.9); 7.9140 (2.8); 7.8128 (0.4); 7.8054 (0.4); 7.7883 (0.6); 7.7607 (0.5); 7.7540 (0.3); 7.3407 (3.2); 7.3320 (3.4); 7.3083 (7.8); 7.3016 (4.7); 7.2966 (6.9); 7.2919 (5.7); 7.2891 (5.2); 7.2847 (4.5); 7.2760 (4.1); 7.2724 (5.1); 7.2681 (7.0); 7.2424 (2.7); 7.2212 (3.0); 7.2129 (6.1); 7.1919 (6.4); 7.1835 (3.9); 7.1624 (3.8); 7.0894 (0.8); 7.0743 (3.2); 7.0713 (3.0); 7.0655 (3.0); 7.0430 (4.2); 7.0364δ = 8.4815 (4.3); 8.4784 (5.4); 8.4756 (5.4); 8.4725 (4.8); 8.4652 (4.8); 8.4622 (5.7); 8.4590 (5.3); 8.4561 (4.6); 8.0260 (4.8); 8.0228 (3.4); 8.0020 (7.3); 7.9985 (11.1); 7.9951 (6.8); 7.9717 (5.9); 7.9657 (5.9); 7.9481 (6.3); 7.9421 (6.2); 7.9203 (2.9); 7.9140 (2.8); 7.8128 (0.4); 7.8054 (0.4); 7.7883 (0.6); 7.7607 (0.5); 7.7540 (0.3); 7.3407 (3.2); 7.3320 (3.4); 7.3083 (7.8); 7.3016 (4.7); 7.2966 (6.9); 7.2919 (5.7); 7.2891 (5.2); 7.2847 (4.5); 7.2760 (4.1); 7.2724 (5.1); 7.2681 (7.0); 7.2424 (2.7); 7.2212 (3.0); 7.2129 (6.1); 7.1919 (6.4); 7.1835 (3.9); 7.1624 (3.8); 7.0894 (0.8); 7.0743 (3.2); 7.0713 (3.0); 7.0655 (3.0); 7.0430 (4.2); 7.0364
(4.0) ; 7.0138 (2.8); 7.0084 (2.1); 6.9878 (1.1); 4.1675 (0.6); 4.1434 (1.1); 4.1169 (7.9); 4.0939 (16.0); 4.0709 (7.8); 3.3174 (132.1); 3.1773 (0.4); 3.1599 (0.4); 2.9325 (6.0); 2.9088 (11.0); 2.8831 (7.6); 2.8632 (0.9); 2.8529 (0.4); 2.7276 (0.7); 2.5132 (38.2); 2.5073 (74.5); 2.5013 (98.1); 2.4953 (66.2); 2.4894 (29.7); 2.4162 (1.9); 2.3929 (5.7); 2.3680 (7.8); 2.3439 (5.0); 2.3205 (1.4); 2.2715 (0.6); 2.0743 (0.7); 1.2344 (5.0); 1.1939 (0.3); 0.8718 (0.4); 0.8523 (0.6); 0.8296 (0.4); 0.1958 (0.4); 0.0108 (2.8);(4.0); 7.0138 (2.8); 7.0084 (2.1); 6.9878 (1.1); 4.1675 (0.6); 4.1434 (1.1); 4.1169 (7.9); 4.0939 (16.0); 4.0709 (7.8); 3.3174 (132.1); 3.1773 (0.4); 3.1599 (0.4); 2.9325 (6.0); 2.9088 (11.0); 2.8831 (7.6); 2.8632 (0.9); 2.8529 (0.4); 2.7276 (0.7); 2.5132 (38.2); 2.5073 (74.5); 2.5013 (98.1); 2.4953 (66.2); 2.4894 (29.7); 2.4162 (1.9); 2.3929 (5.7); 2.3680 (7.8); 2.3439 (5.0); 2.3205 (1.4); 2.2715 (0.6); 2.0743 (0.7); 1.2344 (5.0); 1.1939 (0.3); 0.8718 (0.4); 0.8523 (0.6); 0.8296 (0.4); 0.1958 (0.4); 0.0108 (2.8);
0.0000 (69.9); -0.0111 (2.0); -0.0626 (0.8) 0.0000 (69.9); -0.0111 (2.0); -0.0626 (0.8)
1-196: Ή-ΝΜϋ^ΟΟ.Ο MHz, CDC13):  1-196: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, CDC13):
δ= 8.6235 (0.7); 8.6115 (0.7); 8.5141 (5.2); 8.5021 (5.4); 7.2613 (22.6); 7.0413 (1.6); 7.0294 (3.0); 7.0174 (1.5); 6.5666 (0.7); 6.5635 (1.8); 6.5475 (2.1); 6.5448 (1.3); 6.5416 (2.0); 6.5256 (1.7); 5.2985 (2.6); 3.8477 (2.3); 3.7688 (16.0); 2.4435 (10.5);δ = 8.6235 (0.7); 8.6115 (0.7); 8.5141 (5.2); 8.5021 (5.4); 7.2613 (22.6); 7.0413 (1.6); 7.0294 (3.0); 7.0174 (1.5); 6.5666 (0.7); 6.5635 (1.8); 6.5475 (2.1); 6.5448 (1.3); 6.5416 (2.0); 6.5256 (1.7); 5.2985 (2.6); 3.8477 (2.3); 3.7688 (16.0); 2.4435 (10.5);
2.3316 (2.3); 1.5607 (1.4); -0.0002 (8.5) 2.3316 (2.3); 1.5607 (1.4); -0.0002 (8.5)
1-197: 1H-NMR(400.0 MHz, CDC13): 1-197: 1 H-NMR (400.0 MHz, CDC13):
δ= 7.2598 (10.0); 7.2587 (10.0); 7.2154 (0.8); 7.1947 (1.9); 7.1762 (1.6); 7.1532 (1.6); 7.1343 (1.6); 7.0926 (2.3); 7.0876 (1.3); 7.0680 (3.2); 7.0542 (1.4); 7.0464 (2.2); 5.7213 (2.5); 5.7203 (2.5); 5.2962 (0.6); 5.2952 (0.6); 3.9205 (8.3); 3.9196 (8.3); 3.8106δ = 7.2598 (10.0); 7.2587 (10.0); 7.2154 (0.8); 7.1947 (1.9); 7.1762 (1.6); 7.1532 (1.6); 7.1343 (1.6); 7.0926 (2.3); 7.0876 (1.3); 7.0680 (3.2); 7.0542 (1.4); 7.0464 (2.2); 5.7213 (2.5); 5.7203 (2.5); 5.2962 (0.6); 5.2952 (0.6); 3.9205 (8.3); 3.9196 (8.3); 3.8106
(16.0); 3.8099 (16.0); 3.8050 (10.0); 3.7144 (8.2); 2.2746 (7.4); 2.2209 (8.1); 1.5682 (0.6); -0.0002 (3.8); -0.0013 (3.8) (16.0); 3.8099 (16.0); 3.8050 (10.0); 3.7144 (8.2); 2.2746 (7.4); 2.2209 (8.1); 1.5682 (0.6); -0.0002 (3.8); -0.0013 (3.8)
1-126: 1H-NMR(400.0 MHz, CDC13): 1-126: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4534 (2.2); 8.4416 (2.2); 7.2602 (29.2); 7.1739 (0.7); 7.1717 (1.1); 7.1676 (0.5); 7.1552 (1.9); 7.1525 (2.2); 7.1505 (1.8); 7.1393 (0.9); 7.1345 (2.4); 7.1331 (1.8); 7.1296 (0.5); 7.0890 (2.0); 7.0851 (3.3); 7.0797 (0.9); 7.0742 (1.2); 7.0718 (1.5); 7.0701 (1.4); 7.0674 (2.3); 7.0659 (1.4); 7.0642 (1.6); 7.0584 (0.8); 7.0535 (1.4); 7.0356 (0.6); 6.9708 (1.4); 6.9588 (2.7); 6.9469 (1.4); 4.1301 (1.1); 4.1122 (1.1); 3.8299 (16.0); 2.3032 (14.6); 2.2938 (0.5); 2.2890 (0.7); 2.0428 (5.2); 1.5570 (3.2); 1.2760 (1.5);δ = 8.4534 (2.2); 8.4416 (2.2); 7.2602 (29.2); 7.1739 (0.7); 7.1717 (1.1); 7.1676 (0.5); 7.1552 (1.9); 7.1525 (2.2); 7.1505 (1.8); 7.1393 (0.9); 7.1345 (2.4); 7.1331 (1.8); 7.1296 (0.5); 7.0890 (2.0); 7.0851 (3.3); 7.0797 (0.9); 7.0742 (1.2); 7.0718 (1.5); 7.0701 (1.4); 7.0674 (2.3); 7.0659 (1.4); 7.0642 (1.6); 7.0584 (0.8); 7.0535 (1.4); 7.0356 (0.6); 6.9708 (1.4); 6.9588 (2.7); 6.9469 (1.4); 4.1301 (1.1); 4.1122 (1.1); 3.8299 (16.0); 2.3032 (14.6); 2.2938 (0.5); 2.2890 (0.7); 2.0428 (5.2); 1.5570 (3.2); 1.2760 (1.5);
1.2581 (3.1); 1.2403 (1.5); -0.0002 (10.4) 1.2581 (3.1); 1.2403 (1.5); -0.0002 (10.4)
1-198: 1H-NMR(400.0 MHz, CDC13): 1-198: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4349 (5.2); 8.4229 (5.2); 7.2607 (13.7); 7.1747 (0.6); 7.1725 (1.0); 7.1563 (1.6); 7.1531 (1.5); 7.1513 (1.5); 7.1490 (0.5); 7.1403 (0.6); 7.1351 (1.9); 7.1338 (1.4); 7.0794 (0.9); 7.0752 (2.8); 7.0706 (1.5); 7.0693 (1.4); 7.0611 (0.6); 7.0587 (0.8); 7.0568 (1.7); 7.0553 (1.8); 7.0537 (1.6); 7.0505 (1.2); 7.0327 (0.5); 6.9578 (1.6); 6.9458 (3.2); 6.9339 (1.6); 4.1529 (1.0); 4.1347 (3.3);δ = 8.4349 (5.2); 8.4229 (5.2); 7.2607 (13.7); 7.1747 (0.6); 7.1725 (1.0); 7.1563 (1.6); 7.1531 (1.5); 7.1513 (1.5); 7.1490 (0.5); 7.1403 (0.6); 7.1351 (1.9); 7.1338 (1.4); 7.0794 (0.9); 7.0752 (2.8); 7.0706 (1.5); 7.0693 (1.4); 7.0611 (0.6); 7.0587 (0.8); 7.0568 (1.7); 7.0553 (1.8); 7.0537 (1.6); 7.0505 (1.2); 7.0327 (0.5); 6.9578 (1.6); 6.9458 (3.2); 6.9339 (1.6); 4.1529 (1.0); 4.1347 (3.3);
4.1165 (3.4); 4.0984 (1.0); 2.3092 (16.0); 1.5793 (0.8); 1.4972 (3.6); 1.4791 (7.8); 1.4609 (3.5); -0.0002 (5.2) 4.1165 (3.4); 4.0984 (1.0); 2.3092 (16.0); 1.5793 (0.8); 1.4972 (3.6); 1.4791 (7.8); 1.4609 (3.5); -0.0002 (5.2)
1-199: 1H-NMR(400.0 MHz, CDC13): 1-199: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4175 (5.5); 8.4055 (5.6); 7.2603 (14.2); 7.1769 (0.6); 7.1752 (1.1); 7.1613 (0.7); 7.1579 (1.5); 7.1560 (1.9); 7.1537 (1.4); 7.1511 (0.7); 7.1373 (1.8); 7.0695 (0.5); 7.0679 (0.8); 7.0658 (1.1); 7.0583 (2.4); 7.0553 (2.8); 7.0508 (1.6); 7.0490 (1.6); 7.0417 (0.8); 7.0405 (0.8); 7.0376 (1.6); 7.0347 (2.2); 7.0314 (0.6); 6.9467 (1.6); 6.9348 (3.1); 6.9228 (1.6); 4.4957 (0.9); 4.4792 (1.2);δ = 8.4175 (5.5); 8.4055 (5.6); 7.2603 (14.2); 7.1769 (0.6); 7.1752 (1.1); 7.1613 (0.7); 7.1579 (1.5); 7.1560 (1.9); 7.1537 (1.4); 7.1511 (0.7); 7.1373 (1.8); 7.0695 (0.5); 7.0679 (0.8); 7.0658 (1.1); 7.0583 (2.4); 7.0553 (2.8); 7.0508 (1.6); 7.0490 (1.6); 7.0417 (0.8); 7.0405 (0.8); 7.0376 (1.6); 7.0347 (2.2); 7.0314 (0.6); 6.9467 (1.6); 6.9348 (3.1); 6.9228 (1.6); 4.4957 (0.9); 4.4792 (1.2);
4.4626 (0.9); 2.3130 (16.0); 1.5762 (1.1); 1.5357 (13.8); 1.5191 (13.7); -0.0002 (5.3) 4.4626 (0.9); 2.3130 (16.0); 1.5762 (1.1); 1.5357 (13.8); 1.5191 (13.7); -0.0002 (5.3)
1-200: 'H-NMR(601.6 MHz, CD3CN):  1-200: 'H-NMR (601.6 MHz, CD3CN):
δ= 8.4143 (4.4); 8.4063 (4.4); 7.6053 (1.0); 7.5924 (1.0); 7.4798 (0.5); 7.4787 (0.5); 7.4674 (1.0); 7.4664 (1.0); 7.4540 (0.6); 7.4530 (0.6); 7.2922 (0.7); 7.2909 (0.5); 7.2796 (1.1); 7.2669 (0.5); 7.2023 (1.2); 7.1888 (1.1); 7.1062 (1.5); 7.0982 (2.9); 7.0903 (1.4); 3.8453 (15.5); 2.5381 (2.2); 2.3109 (16.0); 2.3052 (0.3); 2.1923 (4.0); 1.9925 (2.2); 1.9844 (1.1); 1.9803 (1.3); 1.9764δ = 8.4143 (4.4); 8.4063 (4.4); 7.6053 (1.0); 7.5924 (1.0); 7.4798 (0.5); 7.4787 (0.5); 7.4674 (1.0); 7.4664 (1.0); 7.4540 (0.6); 7.4530 (0.6); 7.2922 (0.7); 7.2909 (0.5); 7.2796 (1.1); 7.2669 (0.5); 7.2023 (1.2); 7.1888 (1.1); 7.1062 (1.5); 7.0982 (2.9); 7.0903 (1.4); 3.8453 (15.5); 2.5381 (2.2); 2.3109 (16.0); 2.3052 (0.3); 2.1923 (4.0); 1.9925 (2.2); 1.9844 (1.1); 1.9803 (1.3); 1.9764
(5.1) ; 1.9723 (8.4); 1.9682 (12.2); 1.9641 (8.3); 1.9600 (4.1) (5.1); 1.9723 (8.4); 1.9682 (12.2); 1.9641 (8.3); 1.9600 (4.1)
1-203: 1H-NMR(400.0 MHz, de-DMSO): 1-203: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6483 (11.3); 7.3042 (0.7); 7.2883 (1.5); 7.2847 (1.5); 7.2688 (1.8); 7.2485 (0.7); 6.9659 (1.0); 6.9437 (1.7); 6.9229 (0.8); 6.9188 (0.7); 6.8816 (2.2); 6.8619 (2.0); 6.8330 (1.6); 6.8285 (1.6); 6.8085 (1.6); 6.8042 (1.6); 3.9063 (1.0); 3.9024 (1.5); 3.8253 (16.0); 3.3235 (62.5); 2.7337 (1.3); 2.7154 (3.5); 2.6964 (3.5); 2.6774 (1.6); 2.5056 (113.1); 2.5016 (113.6); 2.3326 (0.6); 2.3282δ = 8.6483 (11.3); 7.3042 (0.7); 7.2883 (1.5); 7.2847 (1.5); 7.2688 (1.8); 7.2485 (0.7); 6.9659 (1.0); 6.9437 (1.7); 6.9229 (0.8); 6.9188 (0.7); 6.8816 (2.2); 6.8619 (2.0); 6.8330 (1.6); 6.8285 (1.6); 6.8085 (1.6); 6.8042 (1.6); 3.9063 (1.0); 3.9024 (1.5); 3.8253 (16.0); 3.3235 (62.5); 2.7337 (1.3); 2.7154 (3.5); 2.6964 (3.5); 2.6774 (1.6); 2.5056 (113.1); 2.5016 (113.6); 2.3326 (0.6); 2.3282
(0.7); 1.0789 (4.0); 1.0599 (7.9); 1.0410 (3.4); 0.0030 (1.3); 0.0001 (1.9); -0.0010 (1.9) (0.7); 1.0789 (4.0); 1.0599 (7.9); 1.0410 (3.4); 0.0030 (1.3); 0.0001 (1.9); -0.0010 (1.9)
1-204: 1H-NMR(400.0 MHz, de-DMSO): 1-204: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.9909 (10.0); 7.3664 (0.4); 7.3592 (3.9); 7.3542 (1.2); 7.3426 (1.4); 7.3376 (4.7); 7.3306 (0.5); 7.1122 (0.5); 7.1052 (4.7); 7.1001 (1.4); 7.0885 (1.2); 7.0835 (3.9); 7.0764 (0.4); 3.9078 (16.0); 3.9034 (3.5); 3.3260 (66.1); 2.6757 (0.3); 2.6712 (0.4); 2.6667 (0.3); 2.6038 (15.1); 2.5246 (1.1); 2.5111 (28.8); 2.5067 (59.4); 2.5022 (78.3); 2.4977 (55.3); 2.4933 (26.0); 2.3334 (0.3);δ = 8.9909 (10.0); 7.3664 (0.4); 7.3592 (3.9); 7.3542 (1.2); 7.3426 (1.4); 7.3376 (4.7); 7.3306 (0.5); 7.1122 (0.5); 7.1052 (4.7); 7.1001 (1.4); 7.0885 (1.2); 7.0835 (3.9); 7.0764 (0.4); 3.9078 (16.0); 3.9034 (3.5); 3.3260 (66.1); 2.6757 (0.3); 2.6712 (0.4); 2.6667 (0.3); 2.6038 (15.1); 2.5246 (1.1); 2.5111 (28.8); 2.5067 (59.4); 2.5022 (78.3); 2.4977 (55.3); 2.4933 (26.0); 2.3334 (0.3);
2.3289 (0.4); -0.0002 (2.3) 2.3289 (0.4); -0.0002 (2.3)
1-205: 1H-NMR(400.0 MHz, de-DMSO): 1-205: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2362 (11.4); 7.2352 (0.5); 7.2136 (1.1); 7.2083 (0.7); 7.1908 (0.5); 7.1853 (0.5); 6.9920 (1.3); 6.9870 (1.6); 6.9710 (2.1); 6.9538 (0.8); 3.9032 (1.3); 3.8160 (16.0); 3.7546 (12.6); 3.3253 (63.6); 2.6711 (0.4); 2.5243 (0.9); 2.5108 (24.5); 2.5064 (50.8);δ = 8.2362 (11.4); 7.2352 (0.5); 7.2136 (1.1); 7.2083 (0.7); 7.1908 (0.5); 7.1853 (0.5); 6.9920 (1.3); 6.9870 (1.6); 6.9710 (2.1); 6.9538 (0.8); 3.9032 (1.3); 3.8160 (16.0); 3.7546 (12.6); 3.3253 (63.6); 2.6711 (0.4); 2.5243 (0.9); 2.5108 (24.5); 2.5064 (50.8);
2.5020 (67.3); 2.4974 (47.6); 2.4930 (22.5); 2.3287 (0.4); 2.2949 (11.9); -0.0002 (1.8) 2.5020 (67.3); 2.4974 (47.6); 2.4930 (22.5); 2.3287 (0.4); 2.2949 (11.9); -0.0002 (1.8)
1-206: 1H-NMR(400.0 MHz, de-DMSO): 1-206: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2553 (11.3); 7.2953 (0.5); 7.2797 (0.6); 7.2752 (1.1); 7.2597 (1.2); 7.2550 (0.8); 7.2394 (0.7); 6.9579 (0.5); 6.9522 (0.5); 6.9370 (0.9); 6.9309 (1.0); 6.9150 (0.4); 6.9101 (0.5); 6.8533 (1.2); 6.8334 (1.2); 6.8009 (0.8); 6.7955 (1.0); 6.7905 (0.6); 6.7764 (0.8); 6.7713 (1.0); 6.7660 (0.6); 3.9030 (1.3); 3.8128 (16.0); 3.7772 (13.2); 3.3242 (49.3); 2.6710 (0.4); 2.5237 (1.1); 2.5101δ = 8.2553 (11.3); 7.2953 (0.5); 7.2797 (0.6); 7.2752 (1.1); 7.2597 (1.2); 7.2550 (0.8); 7.2394 (0.7); 6.9579 (0.5); 6.9522 (0.5); 6.9370 (0.9); 6.9309 (1.0); 6.9150 (0.4); 6.9101 (0.5); 6.8533 (1.2); 6.8334 (1.2); 6.8009 (0.8); 6.7955 (1.0); 6.7905 (0.6); 6.7764 (0.8); 6.7713 (1.0); 6.7660 (0.6); 3.9030 (1.3); 3.8128 (16.0); 3.7772 (13.2); 3.3242 (49.3); 2.6710 (0.4); 2.5237 (1.1); 2.5101
(26.2); 2.5060 (52.0); 2.5016 (67.7); 2.4972 (48.3); 2.4931 (23.2); 2.3285 (0.4); 2.2668 (12.9); -0.0002 (1.8) (26.2); 2.5060 (52.0); 2.5016 (67.7); 2.4972 (48.3); 2.4931 (23.2); 2.3285 (0.4); 2.2668 (12.9); -0.0002 (1.8)
1-207: 1H-NMR(400.0 MHz, de-DMSO): 1-207: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.2657 (11.2); 7.2404 (0.5); 7.2183 (1.1); 7.2132 (0.7); 7.1957 (0.5); 7.1897 (0.5); 7.0128 (1.4); 7.0084 (1.6); 6.9921 (2.3); 6.9757 (0.8); 3.9032 (0.9); 3.8192 (16.0); 3.7901 (13.3); 3.3259 (73.7); 2.7516 (0.7); 2.7326 (2.3); 2.7136 (2.4); 2.6949 (0.7); 2.6712 (0.4); 2.5244 (1.1); 2.5108 (27.8); 2.5065 (57.1); 2.5021 (75.5); 2.4976 (54.0); 2.4933 (25.8); 2.3289 (0.4); 1.0785 (2.6); 1.0596 (5.9); 1.0406 (2.5); -0.0002 (1.1) 1-208: 'H-NMR^O.O MHz, de-DMSO): δ = 8.2657 (11.2); 7.2404 (0.5); 7.2183 (1.1); 7.2132 (0.7); 7.1957 (0.5); 7.1897 (0.5); 7.0128 (1.4); 7.0084 (1.6); 6.9921 (2.3); 6.9757 (0.8); 3.9032 (0.9); 3.8192 (16.0); 3.7901 (13.3); 3.3259 (73.7); 2.7516 (0.7); 2.7326 (2.3); 2.7136 (2.4); 2.6949 (0.7); 2.6712 (0.4); 2.5244 (1.1); 2.5108 (27.8); 2.5065 (57.1); 2.5021 (75.5); 2.4976 (54.0); 2.4933 (25.8); 2.3289 (0.4); 1.0785 (2.6); 1.0596 (5.9); 1.0406 (2.5); -0.0002 (1.1) 1-208: 'H NMR ^ OO MHz, de-DMSO):
δ= 8.6515 (11.4); 7.4375 (1.4); 7.4307 (1.5); 7.4161 (1.4); 7.4093 (1.4); 7.1898 (0.7); 7.1830 (0.7); 7.1682 (1.3); 7.1614 (1.2); 7.1466 (0.8); 7.1398 (0.8); 6.9076 (1.5); 6.8930 (1.6); 6.8853 (1.3); 6.8707 (1.3); 3.9032 (1.1); 3.8304 (16.0); 3.3255 (91.7); 2.7191 (0.8); 2.7000 (2.8); 2.6809 (3.0); 2.6715 (0.7); 2.6622 (1.0); 2.5244 (1.3); 2.5109 (32.6); 2.5066 (67.0); 2.5022 (88.5); 2.4977 (63.3); 2.4935 (30.4); 2.3336 (0.4); 2.3291 (0.5); 2.3244 (0.4); 1.0736 (3.1); 1.0547 (7.2); 1.0357 (3.0); -0.0002 (0.9) 1-209: Ή-ΝΜϋ^ΟΟ.Ο MHz, de-DMSO): δ = 8.6515 (11.4); 7.4375 (1.4); 7.4307 (1.5); 7.4161 (1.4); 7.4093 (1.4); 7.1898 (0.7); 7.1830 (0.7); 7.1682 (1.3); 7.1614 (1.2); 7.1466 (0.8); 7.1398 (0.8); 6.9076 (1.5); 6.8930 (1.6); 6.8853 (1.3); 6.8707 (1.3); 3.9032 (1.1); 3.8304 (16.0); 3.3255 (91.7); 2,7191 (0.8); 2.7000 (2.8); 2.6809 (3.0); 2.6715 (0.7); 2.6622 (1.0); 2.5244 (1.3); 2.5109 (32.6); 2.5066 (67.0); 2.5022 (88.5); 2.4977 (63.3); 2.4935 (30.4); 2.3336 (0.4); 2.3291 (0.5); 2.3244 (0.4); 1.0736 (3.1); 1.0547 (7.2); 1.0357 (3.0); -0.0002 (0.9) 1-209: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, de-DMSO):
δ= 8.6385 (16.0); 8.2086 (6.7); 7.3123 (0.5); 7.3052 (4.8); 7.3004 (1.6); 7.2885 (1.7); 7.2837 (5.7); 7.2768 (0.7); 7.0737 (0.6); 7.0667 (5.7); 7.0617 (1.7); 7.0500 (1.5); 7.0451 (4.8); 7.0382 (0.5); 4.1584 (1.3); 4.1401 (4.0); 4.1220 (4.1); 4.1038 (1.4); 3.9031 (1.4); 3.3261 (113.8); 2.6756 (0.4); 2.6710 (0.6); 2.6664 (0.4); 2.5240 (1.6); 2.5105 (41.1); 2.5064 (83.2); 2.5020 (109.3); 2.4975δ = 8.6385 (16.0); 8.2086 (6.7); 7.3123 (0.5); 7.3052 (4.8); 7.3004 (1.6); 7.2885 (1.7); 7.2837 (5.7); 7.2768 (0.7); 7.0737 (0.6); 7.0667 (5.7); 7.0617 (1.7); 7.0500 (1.5); 7.0451 (4.8); 7.0382 (0.5); 4.1584 (1.3); 4.1401 (4.0); 4.1220 (4.1); 4.1038 (1.4); 3.9031 (1.4); 3.3261 (113.8); 2.6756 (0.4); 2.6710 (0.6); 2.6664 (0.4); 2.5240 (1.6); 2.5105 (41.1); 2.5064 (83.2); 2.5020 (109.3); 2.4975
(78.1); 2.4934 (37.5); 2.3330 (0.4); 2.3290 (0.6); 2.3242 (0.5); 1.4255 (4.8); 1.4073 (10.4); 1.3891 (4.7); -0.0002 (1.5) (78.1); 2.4934 (37.5); 2.3330 (0.4); 2.3290 (0.6); 2.3242 (0.5); 1.4255 (4.8); 1.4073 (10.4); 1.3891 (4.7); -0.0002 (1.5)
1-210: 1H-NMR(400.0 MHz, de-DMSO): 1-210: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6139 (11.5); 8.1186 (5.5); 7.2490 (1.5); 7.2303 (3.7); 7.2110 (2.8); 7.1378 (1.3); 7.1197 (2.0); 7.1012 (0.7); 7.0625 (3.2); 7.0598 (3.8); 7.0415 (3.2); 3.9030 (0.8); 3.8460 (16.0); 3.3247 (61.1); 2.6707 (0.4); 2.5059 (63.0); 2.5018 (80.7); 2.4976 (58.3);δ = 8.6139 (11.5); 8.1186 (5.5); 7.2490 (1.5); 7.2303 (3.7); 7.2110 (2.8); 7.1378 (1.3); 7.1197 (2.0); 7.1012 (0.7); 7.0625 (3.2); 7/598 (3.8); 7.0415 (3.2); 3.9030 (0.8); 3.8460 (16.0); 3.3247 (61.1); 2.6707 (0.4); 2.5059 (63.0); 2.5018 (80.7); 2.4976 (58.3);
2.3283 (0.5); -0.0002 (1.2) 2.3283 (0.5); -0.0002 (1.2)
1-211 : 1H-NMR(400.0 MHz, de-DMSO): 1-211: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.7491 (0.4); 8.6263 (14.7); 8.1786 (7.6); 7.1044 (16.0); 7.0865 (10.5); 4.1420 (1.6); 4.1240 (4.9); 4.1058 (4.9); 4.0876 (1.6);δ = 8.7491 (0.4); 8.6263 (14.7); 8.1786 (7.6); 7.1044 (16.0); 7.0865 (10.5); 4.1420 (1.6); 4.1240 (4.9); 4.1058 (4.9); 4.0876 (1.6);
3.9032 (1.1); 3.3242 (79.4); 2.6710 (0.6); 2.5061 (88.8); 2.5019 (116.0); 2.4976 (84.8); 2.3284 (0.6); 1.4169 (5.6); 1.3988 (11.8);3.9032 (1.1); 3.3242 (79.4); 2.6710 (0.6); 2.5061 (88.8); 2.5019 (116.0); 2.4976 (84.8); 2.3284 (0.6); 1.4169 (5.6); 1.3988 (11.8);
1.3806 (5.5); 1.3682 (0.3); 1.3501 (0.5); 1.2372 (0.3); -0.0002 (1.7) 1.3806 (5.5); 1.3682 (0.3); 1.3501 (0.5); 1.2372 (0.3); -0.0002 (1.7)
1-212: 1H-NMR(400.1 MHz, de-DMSO): 1-212: 1 H-NMR (400.1 MHz, de-DMSO):
δ= 8.6073 (11.4); 7.0394 (3.1); 7.0191 (4.2); 6.9112 (4.9); 6.8908 (3.6); 3.7604 (16.0); 3.3152 (19.6); 2.5042 (23.0); 2.5001δ = 8.6073 (11.4); 7.0394 (3.1); 7.0191 (4.2); 6.9112 (4.9); 6.8908 (3.6); 3.7604 (16.0); 3.3152 (19.6); 2.5042 (23.0); 2.5001
(30.9); 2.4960 (23.5); 2.2654 (15.8); 2.2144 (12.8); -0.0009 (6.4) (30.9); 2.4960 (23.5); 2.2654 (15.8); 2.2144 (12.8); -0.0009 (6.4)
1-213: 1H-NMR(400.0 MHz, de-DMSO): 1-213: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 7.9516 (1.4); 7.9481 (1.5); 7.9393 (1.5); 7.9359 (1.5); 7.7974 (0.8); 7.7926 (0.8); 7.7752 (1.4); 7.7588 (0.9); 7.7538 (0.9); 7.2244 (0.7); 7.1984 (1.3); 7.1735 (0.7); 7.0746 (1.4); 7.0622 (1.4); 7.0572 (1.4); 7.0446 (1.2); 7.0064 (2.5); 6.9957 (2.0); 6.9846 (3.9); 6.9699 (1.8); 6.9659 (1.9); 4.2219 (0.4); 3.9032 (0.8); 3.7554 (16.0); 3.3268 (62.9); 2.6709 (0.5); 2.5056 (78.0); 2.5018 (99.5); 2.4980 (74.7); 2.3284 (0.6); 2.2818 (15.7); 2.2632 (0.4); 1.2971 (0.4); 1.2836 (0.6); 1.2585 (0.4); 1.2352 (0.6); 0.9303δ = 7.9516 (1.4); 7.9481 (1.5); 7.9393 (1.5); 7.9359 (1.5); 7.7974 (0.8); 7.7926 (0.8); 7.7752 (1.4); 7.7588 (0.9); 7.7538 (0.9); 7.2244 (0.7); 7.1984 (1.3); 7.1735 (0.7); 7.0746 (1.4); 7.0622 (1.4); 7.0572 (1.4); 7.0446 (1.2); 7.0064 (2.5); 6.9957 (2.0); 6.9846 (3.9); 6.9699 (1.8); 6.9659 (1.9); 4.2219 (0.4); 3.9032 (0.8); 3.7554 (16.0); 3.3268 (62.9); 2.6709 (0.5); 2.5056 (78.0); 2.5018 (99.5); 2.4980 (74.7); 2.3284 (0.6); 2.2818 (15.7); 2.2632 (0.4); 1.2971 (0.4); 1.2836 (0.6); 1.2585 (0.4); 1.2352 (0.6); 0.9303
(0.3); 0.9121 (0.6); 0.8936 (0.6); 0.8753 (0.8); 0.8615 (0.8); 0.8431 (0.4); -0.0002 (1.3) (0.3); 0.9121 (0.6); 0.8936 (0.6); 0.8753 (0.8); 0.8615 (0.8); 0.8431 (0.4); -0.0002 (1.3)
1-214: 1H-NMR(400.0 MHz, de-DMSO): 1-214: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.0008 (1.3); 7.9969 (1.4); 7.9887 (1.4); 7.9846 (1.4); 7.7926 (0.8); 7.7877 (0.8); 7.7714 (1.3); 7.7539 (0.9); 7.7490 (0.9); 7.0736 (6.1); 7.0707 (6.5); 7.0613 (2.0); 7.0547 (12.4); 6.9963 (2.2); 6.9755 (2.1); 3.9029 (0.8); 3.7531 (16.0); 3.3285 (97.6); 2.6708 (0.4); 2.6665 (0.3); 2.5062 (59.3); 2.5019 (77.6); 2.4975 (56.7); 2.3330 (0.3); 2.3285 (0.4); 2.3241 (0.4); 2.2609 (16.0); -δ = 8,0008 (1.3); 7.9969 (1.4); 7.9887 (1.4); 7.9846 (1.4); 7.7926 (0.8); 7,77877 (0.8); 7.7714 (1.3); 7.7539 (0.9); 7.7490 (0.9); 7.0736 (6.1); 7.0707 (6.5); 7.0613 (2.0); 7.0547 (12.4); 6.9963 (2.2); 6.9755 (2.1); 3.9029 (0.8); 3.7531 (16.0); 3.3285 (97.6); 2.6708 (0.4); 2.6665 (0.3); 2.5062 (59.3); 2.5019 (77.6); 2.4975 (56.7); 2.3330 (0.3); 2.3285 (0.4); 2.3241 (0.4); 2.2609 (16.0); -
0.0003 (1.0) 0.0003 (1.0)
1-215: 1H-NMR(400.0 MHz, de-DMSO): 1-215: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6154 (0.5); 8.6096 (0.5); 8.4346 (2.6); 8.4288 (2.6); 8.2600 (1.6); 8.2541 (1.5); 8.2385 (1.7); 8.2325 (1.6); 7.9037 (0.3); 7.8977 (0.3); 7.8810 (0.3); 7.8751 (0.4); 7.2055 (0.6); 7.1996 (0.6); 7.1819 (0.9); 7.1771 (1.4); 7.1521 (3.0); 7.1305 (2.4); 6.9964 (1.0); 6.9801 (2.7); 6.9642 (2.0); 6.9611 (1.9); 3.9034 (1.0); 3.8405 (15.6); 3.8223 (1.0); 3.7744 (16.0); 3.3248 (77.1); 3.0477 (2.6); 2.6710 (0.5); 2.6667 (0.4); 2.5241 (1.4); 2.5064 (71.6); 2.5021 (94.3); 2.4977 (67.9); 2.3284 (0.6); 2.3134 (14.1); -0.0002δ = 8.6154 (0.5); 8.6096 (0.5); 8.4346 (2.6); 8.4288 (2.6); 8.2600 (1.6); 8.2541 (1.5); 8.2385 (1.7); 8.2325 (1.6); 7.9037 (0.3); 7,889 (0.3); 7.8810 (0.3); 7.8751 (0.4); 7.2055 (0.6); 7.1996 (0.6); 7.1819 (0.9); 7.1771 (1.4); 7.1521 (3.0); 7.1305 (2.4); 6.9964 (1.0); 6.9801 (2.7); 6.9642 (2.0); 6.9611 (1.9); 3.9034 (1.0); 3.8405 (15.6); 3.8223 (1.0); 3.7744 (16.0); 3.3248 (77.1); 3.0477 (2.6); 2.6710 (0.5); 2.6667 (0.4); 2.5241 (1.4); 2.5064 (71.6); 2.5021 (94.3); 2.4977 (67.9); 2.3284 (0.6); 2.3134 (14.1); -0.0002
(1 -4) (1 -4)
1-216: 1H-NMR(400.0 MHz, de-DMSO): 1-216: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.1640 (2.2); 8.1513 (2.3); 7.5079 (1.8); 7.5048 (1.8); 7.4951 (1.8); 7.4920 (1.8); 7.3056 (3.3); 7.2105 (0.6); 7.2043 (0.6); 7.1870 (0.9); 7.1816 (1.2); 7.1611 (0.6); 7.1569 (0.6); 7.0021 (0.4); 6.9964 (1.0); 6.9792 (2.6); 6.9735 (1.4); 6.9591 (1.9); 6.9530 (1.3); 3.9034 (1.1); 3.8803 (16.0); 3.7713 (14.4); 3.3234 (50.6); 2.6756 (0.4); 2.6712 (0.5); 2.6666 (0.4); 2.5244 (1.4); 2.5107 (34.8); 2.5065 (69.7); 2.5021 (90.9); 2.4977 (64.6); 2.4934 (31.0); 2.3337 (0.4); 2.3286 (0.6); 2.3124 (13.8); -0.0002 (1.6) 1-217: 1H-NMR(400.0 MHz, de-DMSO): δ = 8.1640 (2.2); 8.1513 (2.3); 7.5079 (1.8); 7.5048 (1.8); 7.4951 (1.8); 7.4920 (1.8); 7.3056 (3.3); 7.2105 (0.6); 7.2043 (0.6); 7.1870 (0.9); 7.1816 (1.2); 7.1611 (0.6); 7.1569 (0.6); 7.0021 (0.4); 6.9964 (1.0); 6.9792 (2.6); 6.9735 (1.4); 6.9591 (1.9); 6.9530 (1.3); 3.9034 (1.1); 3.8803 (16.0); 3.7713 (14.4); 3.3234 (50.6); 2.6756 (0.4); 2.6712 (0.5); 2.6666 (0.4); 2.5244 (1.4); 2.5107 (34.8); 2.5065 (69.7); 2.5021 (90.9); 2.4977 (64.6); 2.4934 (31.0); 2.3337 (0.4); 2.3286 (0.6); 2.3124 (13.8); -0.0002 (1.6) 1-217: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.5328 (6.2); 8.5208 (6.3); 7.8053 (4.2); 7.7840 (4.3); 7.2326 (1.6); 7.2206 (3.0); 7.2086 (1.6); 7.1372 (4.2); 7.1159 (4.1);δ = 8.5328 (6.2); 8.5208 (6.3); 7.8053 (4.2); 7.7840 (4.3); 7.2326 (1.6); 7.2206 (3.0); 7.2086 (1.6); 7.1372 (4.2); 7.1159 (4.1);
3.9033 (1.9); 3.8123 (16.0); 3.8032 (14.8); 3.6235 (1.1); 3.3401 (29.1); 3.1684 (0.5); 2.6752 (0.4); 2.6711 (0.6); 2.6666 (0.4); 2.5241 (1.5); 2.5104 (37.6); 2.5064 (75.4); 2.5020 (98.4); 2.4975 (70.1); 2.4932 (33.3); 2.3330 (0.4); 2.3287 (0.6); 2.3239 (0.4);3.9033 (1.9); 3.8123 (16.0); 3.8032 (14.8); 3.6235 (1.1); 3.3401 (29.1); 3.1684 (0.5); 2.6752 (0.4); 2.6711 (0.6); 2.6666 (0.4); 2.5241 (1.5); 2.5104 (37.6); 2.5064 (75.4); 2.5020 (98.4); 2.4975 (70.1); 2.4932 (33.3); 2.3330 (0.4); 2.3287 (0.6); 2.3239 (0.4);
2.2546 (14.3); 2.1474 (1.0); -0.0002 (1.4) 2.2546 (14.3); 2.1474 (1.0); -0.0002 (1.4)
1-218: 1H-NMR(400.0 MHz, de-DMSO): 1-218: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 8.6283 (11.2); 7.8115 (4.2); 7.7902 (4.5); 7.1304 (4.5); 7.1092 (4.2); 3.9032 (2.4); 3.8149 (16.0); 3.8001 (15.3); 3.3310δ = 8.6283 (11.2); 7.8115 (4.2); 7.7902 (4.5); 7.1304 (4.5); 7.1092 (4.2); 3.9032 (2.4); 3.8149 (16.0); 3,8001 (15.3); 3.3310
(116.2); 2.6760 (0.4); 2.6715 (0.5); 2.6672 (0.4); 2.5417 (0.6); 2.5247 (1.2); 2.5111 (33.3); 2.5070 (68.4); 2.5026 (90.5); 2.4982(116.2); 2.6760 (0.4); 2.6715 (0.5); 2.6672 (0.4); 2.5417 (0.6); 2.5247 (1.2); 2.5111 (33.3); 2.5070 (68.4); 2.5026 (90.5); 2.4982
(65.0); 2.3338 (0.4); 2.3292 (0.5); 2.2597 (15.0); -0.0002 (0.7) (65.0); 2.3338 (0.4); 2.3292 (0.5); 2.2597 (15.0); -0.0002 (0.7)
1-219: 1H-NMR(400.0 MHz, CDC13): 1-219: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4654 (5.5); 8.4534 (5.6); 7.2605 (34.9); 7.0879 (0.7); 7.0684 (2.0); 7.0489 (1.7); 7.0401 (1.0); 7.0356 (2.1); 7.0316 (1.5); 7.0184 (1.2); 7.0153 (1.6); 7.0135 (1.0); 7.0103 (1.0); 6.9987 (0.7); 6.9958 (0.8); 6.9937 (0.7); 6.9908 (0.5); 6.9778 (1.6); 6.9658 (3.2); 6.9613 (1.2); 6.9580 (1.4); 6.9570 (1.4); 6.9538 (2.5); 6.9421 (0.8); 6.9390 (0.9); 6.9376 (0.9); 6.9346 (0.7); 5.2983 (3.1); 3.9473 (16.0); 1.6946 (0.5); 1.6802 (1.1); 1.6600 (0.5); 1.5509 (4.4); 1.2559 (0.5); 0.9895 (1.0); 0.9861 (2.2); 0.9831 (2.0);δ = 8.4654 (5.5); 8.4534 (5.6); 7.2605 (34.9); 7.0879 (0.7); 7.0684 (2.0); 7.0489 (1.7); 7.0401 (1.0); 7.0356 (2.1); 7.0316 (1.5); 7.0184 (1.2); 7.0153 (1.6); 7.0135 (1.0); 7.0103 (1.0); 6.9987 (0.7); 6.9958 (0.8); 6.9937 (0.7); 6.9908 (0.5); 6.9778 (1.6); 6.9658 (3.2); 6.9613 (1.2); 6.9580 (1.4); 6.9570 (1.4); 6.9538 (2.5); 6.9421 (0.8); 6.9390 (0.9); 6.9376 (0.9); 6.9346 (0.7); 5.2983 (3.1); 3.9473 (16.0); 1.6946 (0.5); 1.6802 (1.1); 1.6600 (0.5); 1.5509 (4.4); 1.2559 (0.5); 0.9895 (1.0); 0.9861 (2.2); 0.9831 (2.0);
0.9791 (2.4); 0.9762 (3.2); 0.9719 (3.0); 0.9681 (1.5); 0.9600 (1.4); 0.9561 (2.1); 0.9518 (1.1); -0.0002 (12.4) 0.9791 (2.4); 0.9762 (3.2); 0.9719 (3.0); 0.9681 (1.5); 0.9600 (1.4); 0.9561 (2.1); 0.9518 (1.1); -0.0002 (12.4)
1-220: 1H-NMR(400.0 MHz, CDC13): 1-220: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4787 (2.4); 8.4668 (2.4); 7.4370 (1.9); 7.4317 (1.4); 7.4270 (3.2); 7.4239 (1.7); 7.4203 (4.7); 7.4153 (0.9); 7.4119 (0.8); 7.4004 (0.5); 7.3899 (2.2); 7.3868 (1.3); 7.3830 (1.1); 7.3804 (1.9); 7.3778 (1.0); 7.3760 (0.8); 7.3719 (1.2); 7.3652 (1.1); 7.2603 (15.3); 7.1310 (0.8); 7.1149 (1.4); 7.1122 (2.0); 7.1099 (1.6); 7.0993 (0.8); 7.0945 (2.4); 7.0899 (0.8); 7.0708 (2.5); 7.0664 (3.4); 7.0608 (0.8); 7.0524 (0.8); 7.0492 (1.6); 7.0473 (1.2); 7.0454 (1.7); 7.0420 (1.0); 7.0377 (0.6); 7.0294 (0.6); 7.0241 (1.4); 7.0065 (0.6); 6.9910 (1.3); 6.9790 (2.5); 6.9671 (1.3); 5.2956 (2.8); 3.8575 (16.0); 2.9519 (0.9); 2.8815 (0.7); 2.0423 (1.9); 1.5756 (1.1); 1.2754 (0.6); 1.2575 (1.4); 1.2396 (0.6); -0.0002 (5.8) 1-221 : 'H-NMR^OO.O MHz, CDC13): δ = 8.4787 (2.4); 8.4668 (2.4); 7.4370 (1.9); 7.4317 (1.4); 7.4270 (3.2); 7.4239 (1.7); 7.4203 (4.7); 7.4153 (0.9); 7.4119 (0.8); 7.4004 (0.5); 7.3899 (2.2); 7.3868 (1.3); 7.3830 (1.1); 7.3804 (1.9); 7.3778 (1.0); 7.3760 (0.8); 7.3719 (1.2); 7.3652 (1.1); 7.2603 (15.3); 7.1310 (0.8); 7.1149 (1.4); 7.1122 (2.0); 7.1099 (1.6); 7.0993 (0.8); 7.0945 (2.4); 7.0899 (0.8); 7.0708 (2.5); 7.0664 (3.4); 7.0608 (0.8); 7.0524 (0.8); 7.0492 (1.6); 7.0473 (1.2); 7.0454 (1.7); 7.0420 (1.0); 7.0377 (0.6); 7.0294 (0.6); 7.0241 (1.4); 7.0065 (0.6); 6.9910 (1.3); 6.9790 (2.5); 6.9671 (1.3); 5.2956 (2.8); 3.8575 (16.0); 2.9519 (0.9); 2.8815 (0.7); 2.0423 (1.9); 1.5756 (1.1); 1.2754 (0.6); 1.2575 (1.4); 1.2396 (0.6); -0.0002 (5.8) 1-221: 'H NMR ^ OO.O MHz, CDC13):
δ= 8.4426 (5.1); 8.4307 (5.4); 7.2607 (16.0); 7.2488 (1.1); 7.1583 (1.0); 7.1386 (3.0); 7.1210 (3.5); 7.1014 (4.8); 7.0833 (2.0); 7.0570 (1.2); 7.0394 (1.7); 7.0220 (0.6); 6.9589 (1.4); 6.9469 (2.8); 6.9350 (1.6); 3.8464 (16.0); 3.8021 (0.6); 2.6963 (2.2); 2.6769 (2.8); 2.6572 (2.5); 1.5685 (4.8); 1.5557 (2.4); 1.5363 (2.2); 1.5174 (1.4); 1.2566 (0.8); 0.9364 (3.8); 0.9180 (7.6); 0.8996δ = 8.4426 (5.1); 8.4307 (5.4); 7.2607 (16.0); 7.2488 (1.1); 7.1583 (1.0); 7.1386 (3.0); 7.1210 (3.5); 7.1014 (4.8); 7.0833 (2.0); 7.0570 (1.2); 7.0394 (1.7); 7.0220 (0.6); 6.9589 (1.4); 6.9469 (2.8); 6.9350 (1.6); 3.8464 (16.0); 3.8021 (0.6); 2.6963 (2.2); 2.6769 (2.8); 2.6572 (2.5); 1.5685 (4.8); 1.5557 (2.4); 1.5363 (2.2); 1.5174 (1.4); 1.2566 (0.8); 0.9364 (3.8); 0.9180 (7.6); 0.8996
(3.6); -0.0002 (5.6) (3.6); -0.0002 (5.6)
1-222: Ή-ΝΜϋ^ΟΟ.Ο MHz, CDC13):  1-222: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, CDC13):
δ= 8.5551 (5.4); 8.5432 (5.6); 7.9485 (3.1); 7.9298 (3.5); 7.9262 (2.8); 7.5421 (0.6); 7.5238 (2.0); 7.5053 (1.6); 7.4705 (2.6); 7.4508 (3.7); 7.4330 (1.5); 7.2627 (11.6); 7.0815 (1.5); 7.0696 (3.0); 7.0576 (1.6); 5.2977 (1.4); 3.7862 (0.5); 3.7578 (16.0);δ = 8.5551 (5.4); 8.5432 (5.6); 7.9485 (3.1); 7.9298 (3.5); 7.9262 (2.8); 7.5421 (0.6); 7.5238 (2.0); 7.5053 (1.6); 7.4705 (2.6); 7.4508 (3.7); 7.4330 (1.5); 7.2627 (11.6); 7.0815 (1.5); 7.0696 (3.0); 7.0576 (1.6); 5.2977 (1.4); 3.7862 (0.5); 3.7578 (16.0);
3.6055 (0.7); 2.5639 (15.8); 2.2906 (0.9); 2.0429 (1.6); 1.5850 (0.7); 1.2578 (1.1); -0.0002 (4.4) 3.6055 (0.7); 2.5639 (15.8); 2.2906 (0.9); 2.0429 (1.6); 1.5850 (0.7); 1.2578 (1.1); -0.0002 (4.4)
1-223: 1H-NMR(400.0 MHz, CDC13): 1-223: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.3499 (11.0); 7.6054 (2.1); 7.6013 (2.5); 7.5847 (3.1); 7.5817 (2.9); 7.4202 (0.7); 7.4141 (1.0); 7.4101 (0.6); 7.3985 (3.1); 7.3797 (3.7); 7.3750 (2.7); 7.3712 (1.6); 7.3659 (0.8); 7.3593 (1.2); 7.2637 (11.0); 5.2984 (0.6); 3.7350 (16.0); 2.2982 (15.7);δ = 8.3499 (11.0); 7.6054 (2.1); 7.6013 (2.5); 7.5847 (3.1); 7.5817 (2.9); 7.4202 (0.7); 7.4141 (1.0); 7.4101 (0.6); 7.3985 (3.1); 7.3797 (3.7); 7.3750 (2.7); 7.3712 (1.6); 7.3659 (0.8); 7.3593 (1.2); 7.2637 (11.0); 5.2984 (0.6); 3.7350 (16.0); 2.2982 (15.7);
1.6162 (0.9); -0.0002 (4.2) 1.6162 (0.9); -0.0002 (4.2)
1-224: 1H-NMR(400.0 MHz, CDC13): 1-224: 1 H NMR (400.0 MHz, CDC13):
δ= 8.2413 (7.3); 7.2597 (42.4); 7.2119 (0.6); 7.1687 (1.2); 7.1493 (2.9); 7.1314 (3.0); 7.0802 (4.4); 7.0737 (2.6); 7.0615 (2.9); 7.0535 (2.3); 7.0354 (0.9); 4.1304 (1.6); 4.1126 (1.6); 4.0948 (0.6); 3.8202 (16.0); 2.2936 (15.7); 2.1895 (12.6); 2.0432 (6.8);δ = 8.2413 (7.3); 7.2597 (42.4); 7.2119 (0.6); 7.1687 (1.2); 7.1493 (2.9); 7.1314 (3.0); 7.0802 (4.4); 7.0737 (2.6); 7.0615 (2.9); 7.0535 (2.3); 7.0354 (0.9); 4.1304 (1.6); 4.1126 (1.6); 4.0948 (0.6); 3.8202 (16.0); 2.2936 (15.7); 2.1895 (12.6); 2.0432 (6.8);
1.5438 (5.3); 1.2762 (1.8); 1.2584 (3.7); 1.2405 (1.9); -0.0002 (16.3) 1.5438 (5.3); 1.2762 (1.8); 1.2584 (3.7); 1.2405 (1.9); -0.0002 (16.3)
1-225: 1H-NMR(400.0 MHz, CDC13): 1-225: 1 H NMR (400.0 MHz, CDC13):
δ= 8.4475 (3.3); 8.4355 (3.7); 7.5181 (9.8); 7.2988 (2.2); 7.2593 (1718.1); 7.2233 (1.4); 7.2091 (4.8); 7.1901 (1.5); 7.1693 (2.5); 7.1501 (2.4); 7.1395 (1.6); 7.0865 (3.5); 7.0663 (2.2); 6.9952 (9.7); 6.9888 (2.5); 4.9107 (7.8); 2.3279 (16.0); 1.5497 (7.2); 1.4320 (6.4); 1.2549 (7.4); 0.8801 (1.4); 0.1461 (3.0); 0.0689 (20.5); 0.0080 (25.6); -0.0002 (777.8); -0.0084 (25.8); -0.0502δ = 8.4475 (3.3); 8.4355 (3.7); 7.5181 (9.8); 7.2988 (2.2); 7.2593 (1718.1); 7.2233 (1.4); 7.2091 (4.8); 7.1901 (1.5); 7.1693 (2.5); 7.1501 (2.4); 7.1395 (1.6); 7.0865 (3.5); 7.0663 (2.2); 6.9952 (9.7); 6,9888 (2.5); 4.9107 (7.8); 2.3279 (16.0); 1.5497 (7.2); 1.4320 (6.4); 1.2549 (7.4); 0.8801 (1.4); 0.1461 (3.0); 0.0689 (20.5); 0.0080 (25.6); -0.0002 (777.8); -0.0084 (25.8); -0.0502
(2.2); -0.1496 (3.0) (2.2); -0.1496 (3.0)
1-044: 1H-NMR(400.0 MHz, CDC13): 1-044: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4980 (2.0); 8.4865 (2.1); 7.2618 (25.8); 7.0894 (0.8); 7.0738 (0.8); 7.0678 (1.4); 7.0523 (1.4); 7.0476 (0.8); 7.0458 (0.7); 7.0301 (1.7); 7.0179 (2.2); 7.0060 (1.1); 6.7414 (0.8); 6.7349 (1.0); 6.7195 (0.9); 6.7174 (0.7); 6.7127 (2.2); 6.7110 (2.1); 6.7029 (0.6); 6.6956 (0.6); 6.6906 (2.6); 6.6833 (0.8); 6.6702 (0.7); 6.6676 (0.6); 5.2982 (4.4); 3.8212 (16.0); 2.3475 (15.4); 2.3260δ = 8.4980 (2.0); 8.4865 (2.1); 7.2618 (25.8); 7.0894 (0.8); 7.0738 (0.8); 7.0678 (1.4); 7.0523 (1.4); 7.0476 (0.8); 7.0458 (0.7); 7.0301 (1.7); 7.0179 (2.2); 7.0060 (1.1); 6.7414 (0.8); 6.7349 (1.0); 6.7195 (0.9); 6.7174 (0.7); 6.7127 (2.2); 6.7110 (2.1); 6.7029 (0.6); 6.6956 (0.6); 6.6906 (2.6); 6.6833 (0.8); 6.6702 (0.7); 6.6676 (0.6); 5.2982 (4.4); 3.8212 (16.0); 2.3475 (15.4); 2.3260
(1.1) ; -0.0002 (10.8) (1.1); -0.0002 (10.8)
1-226: 1H-NMR(400.0 MHz, CDC13): 1-226: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.6581 (4.5); 8.6564 (4.6); 7.2600 (27.7); 7.0727 (1.8); 7.0673 (0.8); 7.0600 (1.9); 7.0559 (1.0); 7.0547 (0.9); 7.0503 (2.5); 7.0431 (0.8); 7.0376 (2.4); 6.8892 (2.4); 6.8836 (0.7); 6.8723 (0.8); 6.8678 (3.4); 6.8624 (0.8); 6.8511 (0.6); 6.8456 (1.9); 3.8342δ = 8.6581 (4.5); 8.6564 (4.6); 7.2600 (27.7); 7.0727 (1.8); 7.0673 (0.8); 7.0600 (1.9); 7.0559 (1.0); 7.0547 (0.9); 7.0503 (2.5); 7.0431 (0.8); 7.0376 (2.4); 6.8892 (2.4); 6.8836 (0.7); 6.8723 (0.8); 6.8678 (3.4); 6.8624 (0.8); 6.8511 (0.6); 6.8456 (1.9); 3.8342
(16.0); 2.3403 (15.3); -0.0002 (11.4) (16.0); 2.3403 (15.3); -0.0002 (11.4)
1-228: 1H-NMR(400.0 MHz, CDC13): 1-228: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4556 (4.8); 8.4438 (4.9); 7.2601 (15.6); 7.1689 (2.0); 7.1484 (4.6); 7.1308 (4.5); 7.0736 (8.5); 7.0543 (6.5); 7.0348 (1.0); 6.9907 (1.8); 6.9788 (3.3); 6.9669 (1.8); 4.1310 (0.8); 4.1131 (0.8); 2.2914 (16.0); 2.0447 (3.5); 1.2757 (0.9); 1.2579 (1.9);δ = 8.4556 (4.8); 8.4438 (4.9); 7.2601 (15.6); 7.1689 (2.0); 7.1484 (4.6); 7.1308 (4.5); 7.0736 (8.5); 7.0543 (6.5); 7.0348 (1.0); 6.9907 (1.8); 6.9788 (3.3); 6.9669 (1.8); 4.1310 (0.8); 4.1131 (0.8); 2.2914 (16.0); 2.0447 (3.5); 1.2757 (0.9); 1.2579 (1.9);
1.2400 (0.9); -0.0002 (5.8) 1.2400 (0.9); -0.0002 (5.8)
1-228: 1H-NMR(400.0 MHz, CDC13): 1-228: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.4768 (4.7); 8.4649 (4.9); 7.2595 (48.7); 7.1728 (1.7); 7.1688 (0.8); 7.1564 (2.9); 7.1536 (3.4); 7.1407 (1.2); 7.1354 (3.7); 7.0810 (5.9); 7.0767 (3.4); 7.0620 (4.3); 7.0572 (3.0); 7.0519 (0.9); 7.0423 (0.7); 7.0391 (1.0); 7.0360 (0.6); 7.0048 (1.6); 6.9928δ = 8.4768 (4.7); 8.4649 (4.9); 7.2595 (48.7); 7.1728 (1.7); 7.1688 (0.8); 7.1564 (2.9); 7.1536 (3.4); 7.1407 (1.2); 7.1354 (3.7); 7.0810 (5.9); 7.0767 (3.4); 7.0620 (4.3); 7.0572 (3.0); 7.0519 (0.9); 7.0423 (0.7); 7.0391 (1.0); 7.0360 (0.6); 7.0048 (1.6); 6.9928
(3.2) ; 6.9808 (1.6); 5.2972 (1.7); 4.1301 (0.9); 4.1123 (0.9); 2.3096 (16.0); 2.0436 (4.0); 1.2753 (1.2); 1.2575 (3.0); 1.2396 (1.1);(3.2); 6.9808 (1.6); 5.2972 (1.7); 4.1301 (0.9); 4.1123 (0.9); 2.3096 (16.0); 2.0436 (4.0); 1.2753 (1.2); 1.2575 (3.0); 1.2396 (1.1);
0.0079 (0.6); -0.0002 (18.4); -0.0085 (0.5) 0.0079 (0.6); -0.0002 (18.4); -0.0085 (0.5)
1-229: 1H-NMR(400.0 MHz, CDC13): 1-229: 1 H NMR (400.0 MHz, CDC13):
δ= 8.4299 (5.7); 8.4180 (5.8); 7.5187 (0.6); 7.2598 (94.3); 6.9958 (0.6); 6.9453 (1.7); 6.9334 (3.2); 6.9214 (1.6); 6.7923 (0.5); 6.7841 (0.7); 6.7694 (0.7); 6.7596 (0.6); 6.7452 (0.6); 6.6528 (0.6); 6.6455 (0.6); 6.6313 (0.6); 6.6238 (0.8); 6.6149 (0.6); 6.6006 (0.6); 6.5934 (0.6); 6.5358 (0.5); 6.5325 (0.7); 6.5290 (0.7); 6.5253 (0.6); 3.7436 (16.0); 3.0996 (7.6); 3.0956 (7.8); 2.9551 (1.3);δ = 8.4299 (5.7); 8.4180 (5.8); 7.5187 (0.6); 7.2598 (94.3); 6.9958 (0.6); 6.9453 (1.7); 6.9334 (3.2); 6.9214 (1.6); 6.7923 (0.5); 6.7841 (0.7); 6.7694 (0.7); 6.7596 (0.6); 6.7452 (0.6); 6.6528 (0.6); 6.6455 (0.6); 6.6313 (0.6); 6.6238 (0.8); 6.6149 (0.6); 6.6006 (0.6); 6,55934 (0.6); 6.5358 (0.5); 6.5325 (0.7); 6.5290 (0.7); 6.5253 (0.6); 3.7436 (16.0); 3.0996 (7.6); 3.0956 (7.8); 2.9551 (1.3);
2.8841 (1.1); 2.8828 (1.1); 2.1741 (13.4); 1.5407 (24.5); 0.0079 (1.3); -0.0002 (40.1); -0.0085 (1.2) 2.8841 (1.1); 2.8828 (1.1); 2.1741 (13.4); 1.5407 (24.5); 0.0079 (1.3); -0.0002 (40.1); -0.0085 (1.2)
1-230: 1H-NMR(400.0 MHz, CDC13):  1-230: 1H NMR (400.0 MHz, CDC13):
δ= 8.4947 (12.5); 7.5091 (4.5); 7.2612 (17.8); 7.2078 (3.8); 7.2027 (1.4); 7.1913 (1.6); 7.1861 (5.2); 7.1794 (0.6); 7.0571 (0.7);δ = 8.4947 (12.5); 7.5091 (4.5); 7.2612 (17.8); 7.2078 (3.8); 7.2027 (1.4); 7.1913 (1.6); 7.1861 (5.2); 7.1794 (0.6); 7.0571 (0.7);
7.0504 (5.1); 7.0452 (1.5); 7.0338 (1.3); 7.0287 (3.9); 3.8489 (16.0); 3.8377 (0.5); 1.5643 (7.7); -0.0002 (6.7) 7.0504 (5.1); 7.0452 (1.5); 7.0338 (1.3); 7.0287 (3.9); 3.8489 (16.0); 3.8377 (0.5); 1.5643 (7.7); -0.0002 (6.7)
1-231 : 1H-NMR(400.0 MHz, CDC13):  1-231: 1H NMR (400.0 MHz, CDC13):
δ= 8.4770 (11.8); 8.3984 (0.5); 7.4994 (4.3); 7.2603 (35.9); 7.1398 (2.0); 7.1344 (0.8); 7.1271 (2.1); 7.1229 (1.0); 7.1174 (2.5); 7.1103 (0.9); 7.1048 (2.4); 6.9596 (2.6); 6.9540 (0.8); 6.9427 (0.9); 6.9383 (3.6); 6.9329 (0.8); 6.9216 (0.7); 6.9161 (1.9); 3.8378δ = 8.4770 (11.8); 8.3984 (0.5); 7.4994 (4.3); 7.2603 (35.9); 7.1398 (2.0); 7.1344 (0.8); 7.1271 (2.1); 7.1229 (1.0); 7.1174 (2.5); 7.1103 (0.9); 7.1048 (2.4); 6.9596 (2.6); 6.9540 (0.8); 6.9427 (0.9); 6.9383 (3.6); 6.9329 (0.8); 6.9216 (0.7); 6.9161 (1.9); 3.8378
(16.0); 1.5493 (1.8); 1.2562 (0.7); -0.0002 (14.0) (16.0); 1.5493 (1.8); 1.2562 (0.7); -0.0002 (14.0)
1-232: 1H-NMR(400.0 MHz, CDC13):  1-232: 1H NMR (400.0 MHz, CDC13):
δ= 7.8858 (0.9); 7.8652 (0.9); 7.2844 (1.1); 7.2805 (1.5); 7.2606 (45.8); 7.2459 (2.6); 7.2276 (3.1); 7.2077 (1.4); 7.1471 (0.6); 7.1439 (1.1); 7.1402 (0.6); 7.1310 (0.5); 7.1261 (1.4); 7.1086 (0.6); 3.2472 (10.2); 2.4166 (16.0); 1.2555 (0.9); -0.0002 (16.6); -δ = 7.8858 (0.9); 7.8652 (0.9); 7.2844 (1.1); 7.2805 (1.5); 7.2606 (45.8); 7.2459 (2.6); 7.2276 (3.1); 7.2077 (1.4); 7.1471 (0.6); 7.1439 (1.1); 7.1402 (0.6); 7.1310 (0.5); 7.1261 (1.4); 7.1086 (0.6); 3.2472 (10.2); 2.4166 (16.0); 1.2555 (0.9); -0.0002 (16.6); -
0.0085 (0.5) 0.0085 (0.5)
1-233: 1H-NMR(400.0 MHz, CDC13):  1-233: 1H NMR (400.0 MHz, CDC13):
δ= 9.1463 (0.6); 8.8940 (0.7); 7.2869 (0.7); 7.2823 (1.1); 7.2767 (0.5); 7.2649 (4.3); 7.2612 (21.8); 7.2523 (1.0); 7.2404 (2.7); 7.2358 (1.1); 7.2249 (0.6); 7.2203 (1.0); 7.1713 (0.6); 7.1670 (0.9); 7.1621 (0.6); 7.1497 (1.0); 3.2564 (15.2); 2.4458 (16.0); -δ = 9.1463 (0.6); 8.8940 (0.7); 7.2869 (0.7); 7.2823 (1.1); 7.2767 (0.5); 7.2649 (4.3); 7.2612 (21.8); 7.2523 (1.0); 7.2404 (2.7); 7.2358 (1.1); 7.2249 (0.6); 7.2203 (1.0); 7.1713 (0.6); 7.1670 (0.9); 7.1621 (0.6); 7.1497 (1.0); 3.2564 (15.2); 2.4458 (16.0); -
0.0002 (10.5); -0.0085 (0.6) 0.0002 (10.5); -0.0085 (0.6)
1-234: 1H-NMR(400.0 MHz, CDC13):  1-234: 1H NMR (400.0 MHz, CDC13):
δ= 8.4789 (6.4); 8.4669 (6.7); 7.2598 (29.2); 7.0891 (1.7); 7.0840 (0.7); 7.0707 (2.3); 7.0676 (2.4); 7.0624 (0.5); 7.0542 (0.7); 7.0493 (2.1); 6.9765 (1.9); 6.9646 (3.7); 6.9526 (1.9); 6.6884 (0.9); 6.6857 (0.6); 6.6701 (1.6); 6.6677 (0.9); 6.6518 (0.8); 6.5345 (2.1); 6.5318 (2.7); 6.5298 (1.5); 6.5266 (0.8); 6.5178 (0.8); 6.5153 (1.3); 6.5128 (2.5); 6.5103 (2.1); 5.2971 (1.2); 3.7811 (16.0); 2.1640 (15.4); 2.0429 (0.6); -0.0002 (13.3); -0.0085 (0.6) 1-235: 1H-NMR(400.0 MHz, CDC13): δ = 8.4789 (6.4); 8.4669 (6.7); 7.2598 (29.2); 7.0891 (1.7); 7.0840 (0.7); 7.0707 (2.3); 7.0676 (2.4); 7.0624 (0.5); 7.0542 (0.7); 7.0493 (2.1); 6.9765 (1.9); 6.9646 (3.7); 6.9526 (1.9); 6.6884 (0.9); 6.6857 (0.6); 6.6701 (1.6); 6.6677 (0.9); 6.6518 (0.8); 6.5345 (2.1); 6.5318 (2.7); 6.5298 (1.5); 6.5266 (0.8); 6.5178 (0.8); 6.5153 (1.3); 6.5128 (2.5); 6.5103 (2.1); 5.2971 (1.2); 3.7811 (16.0); 2.1640 (15.4); 2.0429 (0.6); -0.0002 (13.3); -0.0085 (0.6) 1-235: 1H NMR (400.0 MHz, CDC13):
δ= 8.4970 (5.4); 8.4850 (5.4); 7.2609 (24.2); 7.0124 (1.6); 7.0005 (3.0); 6.9885 (1.5); 6.6997 (0.6); 6.6930 (0.8); 6.6784 (0.8); 6.6717 (1.2); 6.6646 (0.8); 6.6504 (1.0); 6.6436 (1.1); 6.6287 (1.0); 6.6053 (0.6); 6.5675 (0.8); 6.5535 (0.8); 6.5438 (1.0); 6.5299δ = 8.4970 (5.4); 8.4850 (5.4); 7.2609 (24.2); 7.0124 (1.6); 7,0005 (3.0); 6.9885 (1.5); 6.6997 (0.6); 6.6930 (0.8); 6.6784 (0.8); 6.6717 (1.2); 6.6646 (0.8); 6.6504 (1.0); 6.6436 (1.1); 6.6287 (1.0); 6.6053 (0.6); 6.5675 (0.8); 6.5535 (0.8); 6.5438 (1.0); 6.5299
(1.0); 5.2982 (1.4); 4.7539 (0.9); 3.8003 (0.6); 3.7846 (16.0); 3.5929 (0.8); 2.1785 (15.2); 1.9193 (0.7); -0.0002 (10.4) (1.0); 5.2982 (1.4); 4.7539 (0.9); 3.8003 (0.6); 3.7846 (16.0); 3.5929 (0.8); 2.1785 (15.2); 1.9193 (0.7); -0.0002 (10.4)
1-237: 1H-NMR(400.0 MHz, CDC13):  1-237: 1H NMR (400.0 MHz, CDC13):
δ= 8.5002 (5.8); 8.4882 (5.8); 7.2621 (13.6); 7.0153 (1.8); 7.0033 (3.4); 6.9913 (1.6); 6.8793 (0.6); 6.8572 (1.2); 6.8540 (0.7); 6.8351 (0.7); 6.8319 (1.2); 6.8098 (0.6); 6.3554 (0.6); 6.3483 (0.6); 6.3386 (0.6); 6.3316 (0.6); 6.3240 (0.6); 6.3170 (0.6); 6.3072 (0.6); 6.3002 (0.6); 6.2165 (0.6); 6.2137 (0.6); 6.1943 (0.5); 6.1915 (0.5); 5.2983 (1.1); 3.7844 (16.0); 2.1630 (15.5); -0.0002δ = 8,5002 (5.8); 8.4882 (5.8); 7.2621 (13.6); 7.0153 (1.8); 7.0033 (3.4); 6.9913 (1.6); 6.8793 (0.6); 6.8572 (1.2); 6.8540 (0.7); 6.8351 (0.7); 6.8319 (1.2); 6.8098 (0.6); 6.3554 (0.6); 6.3483 (0.6); 6.3386 (0.6); 6.3316 (0.6); 6.3240 (0.6); 6.3170 (0.6); 6.3072 (0.6); 6.3002 (0.6); 6.2165 (0.6); 6.2137 (0.6); 6.1943 (0.5); 6.1915 (0.5); 5.2983 (1.1); 3.7844 (16.0); 2.1630 (15.5); -0.0002
(5-6) (5-6)
1-238: 1H-NMR(400.0 MHz, CDC13):  1-238: 1H NMR (400.0 MHz, CDC13):
δ= 8.4947 (5.6); 8.4827 (5.7); 8.4784 (0.9); 8.4663 (0.7); 7.2612 (15.0); 7.0219 (0.6); 7.0053 (0.8); 7.0013 (1.5); 6.9993 (2.0); 6.9872 (3.4); 6.9813 (0.9); 6.9753 (1.7); 6.9646 (1.0); 6.3560 (0.8); 6.3501 (0.8); 6.3141 (0.9); 6.3121 (0.9); 6.3086 (1.0); 6.3066 (1.0); 6.2938 (0.8); 6.2917 (0.8); 6.2882 (1.0); 6.2862 (0.9); 6.2446 (0.8); 6.2388 (1.2); 6.2331 (0.6); 6.2160 (0.7); 6.2103 (1.2);δ = 8.4947 (5.6); 8.4827 (5.7); 8.4784 (0.9); 8.4663 (0.7); 7.2612 (15.0); 7.0219 (0.6); 7.0053 (0.8); 7.0013 (1.5); 6.9993 (2.0); 6.9872 (3.4); 6.9813 (0.9); 6.9753 (1.7); 6.9646 (1.0); 6.3560 (0.8); 6.3501 (0.8); 6.3141 (0.9); 6.3121 (0.9); 6.3086 (1.0); 6.3066 (1.0); 6.2938 (0.8); 6.2917 (0.8); 6.2882 (1.0); 6.2862 (0.9); 6.2446 (0.8); 6.2388 (1.2); 6.2331 (0.6); 6.2160 (0.7); 6.2103 (1.2);
6.2045 (0.6); 5.2973 (2.2); 3.7850 (16.0); 3.7806 (2.7); 2.1665 (15.4); 2.0428 (0.6); -0.0002 (6.4) 6.2045 (0.6); 5.2973 (2.2); 3.7850 (16.0); 3.7806 (2.7); 2.1665 (15.4); 2.0428 (0.6); -0.0002 (6.4)
1-239: 1H-NMR(400.0 MHz, CDC13):  1-239: 1H NMR (400.0 MHz, CDC13):
δ= 8.5107 (6.0); 8.4988 (6.1); 7.2621 (12.7); 7.0236 (1.8); 7.0117 (3.4); 6.9997 (1.7); 6.1274 (0.7); 6.1103 (0.6); 6.1047 (1.4); 6.0990 (0.8); 6.0819 (0.7); 6.0762 (0.5); 6.0563 (1.7); 6.0534 (0.9); 6.0508 (1.8); 6.0366 (0.6); 6.0318 (2.0); 6.0288 (0.7); 6.0263δ = 8.5107 (6.0); 8.4988 (6.1); 7.2621 (12.7); 7.0236 (1.8); 7.0117 (3.4); 6.9997 (1.7); 6.1274 (0.7); 6.1103 (0.6); 6.1047 (1.4); 6.0990 (0.8); 6.0819 (0.7); 6.0762 (0.5); 6.0563 (1.7); 6.0534 (0.9); 6.0508 (1.8); 6.0366 (0.6); 6.0318 (2.0); 6.0288 (0.7); 6.0263
(1.3) ; 5.2979 (0.8); 4.9139 (1.0); 3.7877 (16.0); 2.1682 (11.9); -0.0002 (5.5) (1.3); 5.2979 (0.8); 4.9139 (1.0); 3.7877 (16.0); 2.1682 (11.9); -0.0002 (5.5)
1-240: 1H-NMR(400.0 MHz, CDC13):  1-240: 1H NMR (400.0 MHz, CDC13):
δ= 8.4969 (6.1); 8.4849 (6.1); 8.4791 (0.6); 8.4671 (0.6); 7.2608 (22.9); 6.9992 (1.8); 6.9915 (1.3); 6.9872 (3.5); 6.9753 (1.9); 6.9715 (2.4); 6.9514 (1.4); 6.6435 (0.9); 6.6413 (1.0); 6.6386 (1.0); 6.6364 (1.0); 6.6239 (0.8); 6.6216 (0.9); 6.6189 (1.0); 6.6167 (0.9); 6.5222 (1.3); 6.5168 (2.4); 6.5116 (1.4); 6.4248 (1.0); 6.4226 (1.0); 6.4191 (0.9); 6.4169 (0.9); 6.4043 (0.9); 6.4022 (0.9); 6.3986 (0.8); 6.3964 (0.8); 5.2978 (3.7); 4.7570 (1.2); 3.7890 (16.0); 3.7810 (1.6); 2.1638 (12.8); 2.0431 (0.9); 1.5726 (0.6);δ = 8.4969 (6.1); 8.4849 (6.1); 8.4791 (0.6); 8.4671 (0.6); 7.2608 (22.9); 6.9992 (1.8); 6.9915 (1.3); 6.9872 (3.5); 6.9753 (1.9); 6.9715 (2.4); 6.9514 (1.4); 6.6435 (0.9); 6.6413 (1.0); 6.6386 (1.0); 6.6364 (1.0); 6.6239 (0.8); 6.6216 (0.9); 6.6189 (1.0); 6.6167 (0.9); 6.5222 (1.3); 6.5168 (2.4); 6.5116 (1.4); 6.4248 (1.0); 6.4226 (1.0); 6.4191 (0.9); 6.4169 (0.9); 6.4043 (0.9); 6.4022 (0.9); 6.3986 (0.8); 6.3964 (0.8); 5.2978 (3.7); 4.7570 (1.2); 3.7890 (16.0); 3.7810 (1.6); 2.1638 (12.8); 2.0431 (0.9); 1.5726 (0.6);
1.2582 (0.6); -0.0002 (9.8) 1.2582 (0.6); -0.0002 (9.8)
1-241 : 1H-NMR(400.0 MHz, CDC13):  1-241: 1H NMR (400.0 MHz, CDC13):
δ= 8.4789 (1.7); 8.4673 (1.6); 7.2604 (32.3); 7.1802 (0.6); 7.1607 (1.3); 7.1408 (0.8); 6.9882 (1.2); 6.9763 (2.3); 6.9643 (1.1); 6.9161 (1.1); 6.8970 (0.9); 6.7410 (1.6); 6.7076 (0.9); 6.6874 (0.8); 6.6816 (0.7); 5.2980 (1.2); 3.8006 (16.0); 3.7809 (1.0);δ = 8.4789 (1.7); 8.4673 (1.6); 7.2604 (32.3); 7.1802 (0.6); 7.1607 (1.3); 7.1408 (0.8); 6.9882 (1.2); 6.9763 (2.3); 6.9643 (1.1); 6.9161 (1.1); 6.8970 (0.9); 6.7410 (1.6); 6.7076 (0.9); 6.6874 (0.8); 6.6816 (0.7); 5.2980 (1.2); 3.8006 (16.0); 3.7809 (1.0);
2.1647 (15.7); 2.0432 (0.7); 1.2583 (0.5); -0.0002 (13.7) 2.1647 (15.7); 2.0432 (0.7); 1.2583 (0.5); -0.0002 (13.7)
1-242: 1H-NMR(400.0 MHz, CDC13):  1-242: 1H NMR (400.0 MHz, CDC13):
δ= 8.2797 (0.8); 8.2776 (1.1); 8.2754 (1.1); 8.2735 (1.1); 8.2714 (1.2); 8.2692 (0.8); 7.8770 (0.8); 7.8757 (0.8); 7.8707 (0.8); 7.8695 (0.8); 7.8554 (0.8); 7.8541 (0.8); 7.8491 (0.8); 7.8478 (0.8); 7.2600 (22.4); 7.0813 (1.1); 7.0797 (1.5); 7.0780 (1.1); 7.0596 (1.0); 7.0581 (1.4); 7.0565 (1.0); 6.9942 (0.6); 6.9727 (0.9); 6.9692 (0.7); 6.9525 (0.8); 6.9477 (0.9); 6.9275 (0.7); 6.9015 (0.6); 6.8957 (0.7); 6.8833 (0.6); 6.8775 (0.8); 6.8747 (0.7); 6.8689 (0.7); 6.8564 (0.6); 6.8507 (0.7); 6.8021 (0.5); 6.7984 (0.6);δ = 8.2797 (0.8); 8.2776 (1.1); 8.2754 (1.1); 8.2735 (1.1); 8.2714 (1.2); 8.2692 (0.8); 7.8770 (0.8); 7.8757 (0.8); 7.8707 (0.8); 7.8695 (0.8); 7.8554 (0.8); 7.8541 (0.8); 7.8491 (0.8); 7.8478 (0.8); 7.2600 (22.4); 7.0813 (1.1); 7.0797 (1.5); 7.0780 (1.1); 7.0596 (1.0); 7.0581 (1.4); 7.0565 (1.0); 6.9942 (0.6); 6.9727 (0.9); 6.9692 (0.7); 6.9525 (0.8); 6.9477 (0.9); 6.9275 (0.7); 6.9015 (0.6); 6.8957 (0.7); 6.8833 (0.6); 6.8775 (0.8); 6.8747 (0.7); 6.8689 (0.7); 6.8564 (0.6); 6.8507 (0.7); 6.8021 (0.5); 6.7984 (0.6);
6.7923 (0.8); 6.7884 (0.6); 6.7707 (0.6); 3.8361 (16.0); 2.3155 (15.6); -0.0002 (9.8) 6.7923 (0.8); 6.7884 (0.6); 6.7707 (0.6); 3.8361 (16.0); 2.3155 (15.6); -0.0002 (9.8)
1-243: 1H-NMR(400.0 MHz, CDC13):  1-243: 1H NMR (400.0 MHz, CDC13):
δ= 8.2209 (0.8); 8.2188 (1.1); 8.2167 (1.1); 8.2147 (1.1); 8.2126 (1.2); 8.2105 (0.8); 7.8306 (0.8); 7.8293 (0.8); 7.8243 (0.8); 7.8230 (0.8); 7.8090 (0.8); 7.8077 (0.8); 7.8027 (0.8); 7.8014 (0.8); 7.2590 (16.4); 7.1737 (0.6); 7.1711 (1.1); 7.1670 (0.5); 7.1573 (0.6); 7.1531 (2.7); 7.1499 (1.6); 7.1379 (0.9); 7.1342 (2.3); 7.1325 (1.6); 7.0890 (0.6); 7.0857 (1.2); 7.0825 (0.9); 7.0672δ = 8.2209 (0.8); 8.2188 (1.1); 8.2167 (1.1); 8.2147 (1.1); 8.2126 (1.2); 8.2105 (0.8); 7.8306 (0.8); 7.8293 (0.8); 7.8243 (0.8); 7.8230 (0.8); 7.8090 (0.8); 7.8077 (0.8); 7.8027 (0.8); 7.8014 (0.8); 7.2590 (16.4); 7.1737 (0.6); 7.1711 (1.1); 7.1670 (0.5); 7.1573 (0.6); 7.1531 (2.7); 7.1499 (1.6); 7.1379 (0.9); 7.1342 (2.3); 7.1325 (1.6); 7.0890 (0.6); 7.0857 (1.2); 7.0825 (0.9); 7.0672
(1.4) ; 7.0490 (0.8); 7.0427 (3.6); 7.0392 (3.3); 7.0338 (0.7); 7.0236 (1.8); 7.0217 (3.1); 7.0186 (2.0); 3.8309 (16.0); 2.3211(1.4); 7.0490 (0.8); 7.0427 (3.6); 7.0392 (3.3); 7.0338 (0.7); 7.0236 (1.8); 7.0217 (3.1); 7.0186 (2.0); 3.8309 (16.0); 2.3211
(15.6); 1.5498 (1.9); -0.0002 (7.2) (15.6); 1.5498 (1.9); -0.0002 (7.2)
1-244: 1H-NMR(400.0 MHz, CDC13):  1-244: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3918 (5.3); 8.3799 (5.3); 7.6323 (0.6); 7.6283 (1.0); 7.6269 (1.1); 7.6229 (0.7); 7.5612 (0.5); 7.5431 (0.6); 7.5417 (0.7); 7.4438 (1.0); 7.4244 (0.7); 7.4229 (0.6); 7.4100 (0.9); 7.2597 (16.3); 6.7220 (1.5); 6.7100 (2.8); 6.6981 (1.4); 3.8573 (16.0);δ = 8.3918 (5.3); 8.3799 (5.3); 7.6323 (0.6); 7.6283 (1.0); 7.6269 (1.1); 7.6229 (0.7); 7.5612 (0.5); 7.5431 (0.6); 7.5417 (0.7); 7.4438 (1.0); 7.4244 (0.7); 7.4229 (0.6); 7.4100 (0.9); 7.2597 (16.3); 6.7220 (1.5); 6.7100 (2.8); 6.6981 (1.4); 3.8573 (16.0);
3.6640 (13.2); 2.0496 (13.3); 1.5768 (1.8); -0.0002 (7.6) 3.6640 (13.2); 2.0496 (13.3); 1.5768 (1.8); -0.0002 (7.6)
1-245: 1H-NMR(400.0 MHz, CDC13):  1-245: 1H NMR (400.0 MHz, CDC13):
δ= 8.4325 (4.4); 8.4206 (4.4); 7.2597 (47.6); 7.1281 (1.7); 7.1228 (0.6); 7.1099 (2.2); 7.1061 (2.3); 7.0931 (0.7); 7.0879 (2.0); 6.9337 (1.5); 6.9217 (2.8); 6.9097 (1.4); 6.6767 (0.9); 6.6742 (0.6); 6.6585 (1.6); 6.6562 (1.0); 6.6403 (0.8); 6.6376 (0.6); 6.6304 (2.0); 6.6279 (2.4); 6.6109 (1.2); 6.6083 (2.3); 6.6060 (1.8); 3.7817 (12.2); 3.0751 (16.0); 3.0462 (0.6); 2.0797 (12.2); 0.0080δ = 8.4325 (4.4); 8.4206 (4.4); 7.2597 (47.6); 7.1281 (1.7); 7.1228 (0.6); 7.1099 (2.2); 7.1061 (2.3); 7.0931 (0.7); 7.0879 (2.0); 6.9337 (1.5); 6.9217 (2.8); 6.9097 (1.4); 6.6767 (0.9); 6.6742 (0.6); 6.6585 (1.6); 6.6562 (1.0); 6.6403 (0.8); 6.6376 (0.6); 6.6304 (2.0); 6.6279 (2.4); 6.6109 (1.2); 6.6083 (2.3); 6.6060 (1.8); 3.7817 (12.2); 3.0751 (16.0); 3.0462 (0.6); 2.0797 (12.2); 0.0080
(0.8); -0.0002 (21.5); -0.0085 (0.6) (0.8); -0.0002 (21.5); -0.0085 (0.6)
1-246: 1H-NMR(400.0 MHz, CDC13):  1-246: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4476 (4.3); 8.4356 (4.3); 7.2601 (37.8); 6.9629 (1.6); 6.9509 (2.9); 6.9389 (1.5); 6.8229 (1.8); 6.8170 (0.6); 6.8057 (0.8); 6.8000 (2.8); 6.7848 (0.6); 6.7789 (2.2); 6.5538 (2.1); 6.5479 (0.7); 6.5428 (2.2); 6.5368 (1.1); 6.5308 (1.8); 6.5257 (0.6); 6.5198δ = 8.4476 (4.3); 8.4356 (4.3); 7.2601 (37.8); 6.9629 (1.6); 6.9509 (2.9); 6.9389 (1.5); 6.8229 (1.8); 6.8170 (0.6); 6.8057 (0.8); 6.8000 (2.8); 6.7848 (0.6); 6.7789 (2.2); 6.5538 (2.1); 6.5479 (0.7); 6.5428 (2.2); 6.5368 (1.1); 6.5308 (1.8); 6.5257 (0.6); 6.5198
(1.7); 3.7791 (15.2); 3.0747 (0.5); 3.0460 (16.0); 2.0836 (15.0); 0.0080 (0.6); -0.0002 (16.6); -0.0084 (0.5) (1.7); 3.7791 (15.2); 3.0747 (0.5); 3.0460 (16.0); 2.0836 (15.0); 0.0080 (0.6); -0.0002 (16.6); -0.0084 (0.5)
1-247: 1H-NMR(400.0 MHz, CDC13):  1-247: 1H NMR (400.0 MHz, CDC13):
δ= 8.4512 (5.8); 8.4392 (5.9); 8.4262 (0.6); 8.4142 (0.5); 7.2616 (14.1); 7.0277 (0.9); 7.0105 (0.6); 7.0068 (1.7); 6.9879 (0.9); 6.9864 (1.0); 6.9531 (1.7); 6.9411 (3.2); 6.9291 (1.6); 6.6310 (0.9); 6.6289 (1.1); 6.6262 (1.3); 6.6242 (1.3); 6.6122 (1.2); 6.6091 (3.3); 6.6054 (3.1); 6.5137 (0.9); 6.5119 (1.0); 6.5077 (0.9); 6.5058 (0.9); 6.4930 (0.8); 6.4888 (1.0); 6.4846 (0.7); 3.7889 (16.0);δ = 8.4512 (5.8); 8.4392 (5.9); 8.4262 (0.6); 8.4142 (0.5); 7.2616 (14.1); 7.0277 (0.9); 7.0105 (0.6); 7.0068 (1.7); 6.9879 (0.9); 6.9864 (1.0); 6.9531 (1.7); 6.9411 (3.2); 6.9291 (1.6); 6.6310 (0.9); 6.6289 (1.1); 6.6262 (1.3); 6.6242 (1.3); 6.6122 (1.2); 6.6091 (3.3); 6.6054 (3.1); 6.5137 (0.9); 6.5119 (1.0); 6.5077 (0.9); 6.5058 (0.9); 6.4930 (0.8); 6.4888 (1.0); 6.4846 (0.7); 3.7889 (16.0);
3.7794 (1.6); 3.0748 (1.7); 3.0655 (15.9); 2.0850 (15.6); 2.0770 (1.7); 1.5822 (1.7); -0.0002 (5.8) 3.7794 (1.6); 3.0748 (1.7); 3.0655 (15.9); 2.0850 (15.6); 2.0770 (1.7); 1.5822 (1.7); -0.0002 (5.8)
1-248: 1H-NMR(400.0 MHz, CDC13):  1-248: 1H NMR (400.0 MHz, CDC13):
δ= 8.5991 (0.6); 8.5872 (0.6); 8.5271 (5.8); 8.5151 (5.8); 8.2624 (4.4); 8.2504 (4.5); 7.2657 (13.5); 7.0260 (1.7); 7.0140 (3.2); 7.0020 (1.7); 6.5994 (1.7); 6.5874 (3.2); 6.5754 (1.6); 6.1471 (1.0); 5.2988 (4.7); 3.7733 (16.0); 3.7664 (1.0); 3.6968 (1.8);δ = 8.5991 (0.6); 8.5872 (0.6); 8.5271 (5.8); 8.5151 (5.8); 8.2624 (4.4); 8.2504 (4.5); 7.2657 (13.5); 7.0260 (1.7); 7.0140 (3.2); 7.0020 (1.7); 6.5994 (1.7); 6.5874 (3.2); 6.5754 (1.6); 6.1471 (1.0); 5.2988 (4.7); 3.7733 (16.0); 3.7664 (1.0); 3.6968 (1.8);
2.2173 (12.8); 2.2129 (2.9); 2.0431 (1.2); 1.2580 (0.9); -0.0002 (5.8) 2.2173 (12.8); 2.2129 (2.9); 2.0431 (1.2); 1.2580 (0.9); -0.0002 (5.8)
1-249: 1H-NMR(400.0 MHz, CDC13):  1-249: 1H NMR (400.0 MHz, CDC13):
δ= 8.4856 (5.8); 8.4737 (5.9); 7.2606 (22.8); 7.0242 (4.0); 7.0187 (1.3); 7.0074 (1.3); 7.0019 (4.5); 6.9990 (2.2); 6.9939 (0.6); 6.9870 (3.3); 6.9750 (1.7); 6.4698 (4.5); 6.4643 (1.4); 6.4530 (1.2); 6.4475 (4.1); 3.7794 (16.0); 2.1508 (15.6); -0.0002 (10.2) 1-250: 1H-NMR(400.0 MHz, CDC13): δ = 8.4856 (5.8); 8.4737 (5.9); 7.2606 (22.8); 7.0242 (4.0); 7.0187 (1.3); 7.0074 (1.3); 7.0019 (4.5); 6.9990 (2.2); 6.9939 (0.6); 6.9870 (3.3); 6.9750 (1.7); 6.4698 (4.5); 6.4643 (1.4); 6.4530 (1.2); 6.4475 (4.1); 3.7794 (16.0); 2.1508 (15.6); -0.0002 (10.2) 1-250: 1H NMR (400.0 MHz, CDC13):
δ= 8.4798 (0.6); 8.4678 (0.6); 8.4484 (6.2); 8.4365 (6.3); 7.2607 (25.5); 7.0427 (0.6); 7.0393 (1.0); 7.0221 (1.1); 7.0191 (0.6); 7.0016 (0.6); 6.9535 (2.1); 6.9416 (3.7); 6.9296 (1.8); 6.3948 (0.6); 6.3928 (0.8); 6.3889 (0.8); 6.3869 (0.9); 6.3739 (0.6); 6.3716 (0.8); 6.3682 (1.0); 6.3658 (1.0); 6.3495 (0.5); 6.3478 (0.5); 6.3445 (0.8); 6.3424 (0.7); 6.3351 (0.7); 6.3295 (1.2); 6.3234 (0.8); 6.3042 (0.7); 6.2983 (1.0); 5.2978 (0.6); 3.7859 (16.0); 3.7818 (2.4); 3.0751 (0.9); 3.0643 (15.6); 2.1645 (1.6); 2.0876 (15.2);δ = 8.4798 (0.6); 8.4678 (0.6); 8.4484 (6.2); 8.4365 (6.3); 7.2607 (25.5); 7.0427 (0.6); 7.0393 (1.0); 7.0221 (1.1); 7.0191 (0.6); 7.0016 (0.6); 6.9535 (2.1); 6.9416 (3.7); 6.9296 (1.8); 6.3948 (0.6); 6.3928 (0.8); 6.3889 (0.8); 6.3869 (0.9); 6.3739 (0.6); 6.3716 (0.8); 6.3682 (1.0); 6.3658 (1.0); 6.3495 (0.5); 6.3478 (0.5); 6.3445 (0.8); 6.3424 (0.7); 6.3351 (0.7); 6.3295 (1.2); 6.3234 (0.8); 6.3042 (0.7); 6.2983 (1.0); 5.2978 (0.6); 3.7859 (16.0); 3.7818 (2.4); 3.0751 (0.9); 3.0643 (15.6); 2.1645 (1.6); 2.0876 (15.2);
2.0773 (0.8); -0.0002 (11.1) 2.0773 (0.8); -0.0002 (11.1)
1-251 : 1H-NMR(400.0 MHz, CDC13):  1-251: 1H NMR (400.0 MHz, CDC13):
δ= 8.4721 (5.9); 8.4602 (6.0); 7.2610 (25.8); 6.9830 (1.8); 6.9710 (3.4); 6.9590 (1.7); 6.1327 (0.7); 6.1287 (1.8); 6.1239 (1.4); 6.1200 (0.5); 6.1067 (1.6); 6.1012 (1.9); 6.0976 (1.0); 6.0800 (0.5); 3.7916 (15.3); 3.0550 (16.0); 2.0967 (14.8); -0.0002 (10.5) 1-252: 1H-NMR(400.0 MHz, CDC13): δ = 8.4721 (5.9); 8.4602 (6.0); 7.2610 (25.8); 6.9830 (1.8); 6.9710 (3.4); 6.9590 (1.7); 6.1327 (0.7); 6.1287 (1.8); 6.1239 (1.4); 6.1200 (0.5); 6.1067 (1.6); 6.1012 (1.9); 6.0976 (1.0); 6.0800 (0.5); 3.7916 (15.3); 3.0550 (16.0); 2.0967 (14.8); -0.0002 (10.5) 1-252: 1H NMR (400.0 MHz, CDC13):
δ= 8.4641 (5.5); 8.4522 (5.6); 8.2925 (3.9); 8.2806 (4.0); 7.2625 (27.5); 6.9669 (1.6); 6.9550 (3.0); 6.9430 (1.5); 6.5282 (1.4);δ = 8.4641 (5.5); 8.4522 (5.6); 8.2925 (3.9); 8.2806 (4.0); 7.2625 (27.5); 6.9669 (1.6); 6.9550 (3.0); 6.9430 (1.5); 6.5282 (1.4);
6.5163 (2.6); 6.5044 (1.3); 5.2988 (2.1); 3.7818 (14.0); 3.7187 (0.5); 3.2814 (16.0); 2.1560 (13.6); -0.0002 (10.9) 6.5163 (2.6); 6.5044 (1.3); 5.2988 (2.1); 3.7818 (14.0); 3.7187 (0.5); 3.2814 (16.0); 2.1560 (13.6); -0.0002 (10.9)
1-253: 1H-NMR(400.0 MHz, CDC13):  1-253: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4379 (5.9); 8.4260 (6.0); 7.3017 (0.5); 7.2622 (12.7); 7.0509 (3.8); 7.0452 (1.2); 7.0338 (1.2); 7.0281 (4.2); 6.9541 (1.7); 6.9422 (3.3); 6.9302 (1.7); 6.5516 (3.8); 6.5460 (1.1); 6.5345 (1.0); 6.5289 (3.5); 5.2975 (2.2); 3.7773 (16.0); 3.0532 (15.8);δ = 8.4379 (5.9); 8.4260 (6.0); 7.3017 (0.5); 7.2622 (12.7); 7.0509 (3.8); 7.0452 (1.2); 7.0338 (1.2); 7.0281 (4.2); 6.9541 (1.7); 6.9422 (3.3); 6.9302 (1.7); 6.5516 (3.8); 6.5460 (1.1); 6.5345 (1.0); 6.5289 (3.5); 5.2975 (2.2); 3.7773 (16.0); 3.0532 (15.8);
2.9538 (2.0); 2.8826 (1.6); 2.8814 (1.7); 2.0697 (15.6); -0.0002 (5.3) 2.9538 (2.0); 2.8826 (1.6); 2.8814 (1.7); 2.0697 (15.6); -0.0002 (5.3)
1-254: 1H-NMR(400.0 MHz, CDC13):  1-254: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4582 (6.2); 8.4462 (6.3); 7.2615 (22.4); 6.9725 (1.8); 6.9606 (3.6); 6.9486 (1.8); 6.9107 (0.6); 6.8881 (1.2); 6.8854 (0.7); 6.8654 (0.7); 6.8627 (1.2); 6.8400 (0.6); 6.4401 (0.5); 6.4326 (0.6); 6.4232 (0.5); 6.4157 (0.6); 6.4061 (0.5); 6.3986 (0.6); 6.3817 (0.5); 6.2808 (0.6); 6.2770 (0.6); 6.2580 (0.5); 6.2542 (0.5); 5.2985 (2.9); 3.7828 (16.0); 3.0370 (14.5); 2.0877 (15.3); -0.0002δ = 8.4582 (6.2); 8.4462 (6.3); 7.2615 (22.4); 6.9725 (1.8); 6.9606 (3.6); 6.9486 (1.8); 6.9107 (0.6); 6.8881 (1.2); 6.8854 (0.7); 6.8654 (0.7); 6.8627 (1.2); 6.8400 (0.6); 6.4401 (0.5); 6.4326 (0.6); 6.4232 (0.5); 6.4157 (0.6); 6.4061 (0.5); 6.3986 (0.6); 6.3817 (0.5); 6.2808 (0.6); 6.2770 (0.6); 6.2580 (0.5); 6.2542 (0.5); 5.2985 (2.9); 3.7828 (16.0); 3.0370 (14.5); 2.0877 (15.3); -0.0002
(8.9) (8.9)
1-255: 1H-NMR(400.0 MHz, CDC13):  1-255: 1H NMR (400.0 MHz, CDC13):
δ= 8.5074 (6.2); 8.4954 (6.3); 8.2592 (0.8); 8.2570 (1.2); 8.2534 (1.2); 8.2511 (1.2); 7.5882 (0.8); 7.5821 (0.8); 7.5662 (0.8); 7.5600 (0.8); 7.2628 (23.8); 7.0370 (1.8); 7.0250 (3.5); 7.0130 (1.7); 6.4531 (1.4); 6.4310 (1.3); 5.9675 (1.0); 5.2985 (5.0);δ = 8.5074 (6.2); 8.4954 (6.3); 8.2592 (0.8); 8.2570 (1.2); 8.2534 (1.2); 8.2511 (1.2); 7,5882 (0.8); 7.5821 (0.8); 7.5662 (0.8); 7.5600 (0.8); 7.2628 (23.8); 7.0370 (1.8); 7.0250 (3.5); 7.0130 (1.7); 6.4531 (1.4); 6.4310 (1.3); 5.9675 (1.0); 5.2985 (5.0);
3.7997 (16.0); 3.7926 (0.5); 2.1897 (11.2); 2.0433 (0.5); 1.2583 (0.6); -0.0002 (9.0) 3.7997 (16.0); 3.7926 (0.5); 2.1897 (11.2); 2.0433 (0.5); 1.2583 (0.6); -0.0002 (9.0)
1-256: lH-NMR(400.0 MHz, d6-DMSO):  1-256: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 8.6562 (16.0); 7.1115 (4.1); 7.1092 (4.3); 7.0929 (11.4); 3.8833 (13.8); 3.3584 (1.1); 3.3084 (215.5); 3.2595 (1.5); 2.6694 (2.0); 2.5500 (2.5); 2.5454 (2.1); 2.5228 (7.4); 2.5181 (10.3); 2.5094 (114.7); 2.5049 (238.6); 2.5002 (329.8); 2.4957 (222.6); 2.4911 (99.0); 2.4553 (1.7); 2.4505 (1.8); 2.3270 (1.9); 2.3225 (1.3); 0.0080 (5.8); -0.0002 (164.4); -0.0085 (4.0); -0.0499 (1.1) 1-257: 1H-NMR(400.0 MHz, CDC13): δ = 8.6562 (16.0); 7.1115 (4.1); 7.1092 (4.3); 7.0929 (11.4); 3.8833 (13.8); 3.3584 (1.1); 3.3084 (215.5); 3.2595 (1.5); 2.6694 (2.0); 2,55500 (2.5); 2.5454 (2.1); 2.5228 (7.4); 2.5181 (10.3); 2.5094 (114.7); 2.5049 (238.6); 2,5002 (329.8); 2.4957 (222.6); 2.4911 (99.0); 2.4553 (1.7); 2.4505 (1.8); 2.3270 (1.9); 2.3225 (1.3); 0.0080 (5.8); -0.0002 (164.4); -0.0085 (4.0); -0.0499 (1.1) 1-257: 1H NMR (400.0 MHz, CDC13):
δ= 8.4894 (6.6); 8.4774 (6.7); 7.2598 (20.0); 6.9875 (1.9); 6.9755 (3.6); 6.9635 (1.8); 6.8896 (1.7); 6.8879 (2.0); 6.8846 (0.8); 6.8827 (0.6); 6.8734 (0.6); 6.8715 (0.8); 6.8681 (2.2); 6.8665 (1.9); 6.4484 (3.0); 6.4434 (0.9); 6.4324 (0.8); 6.4273 (2.7); 5.2964δ = 8.4894 (6.6); 8.4774 (6.7); 7.2598 (20.0); 6.9875 (1.9); 6.9755 (3.6); 6.9635 (1.8); 6.8896 (1.7); 6.8879 (2.0); 6.8846 (0.8); 6.8827 (0.6); 6.8734 (0.6); 6.8715 (0.8); 6.8681 (2.2); 6.8665 (1.9); 6.4484 (3.0); 6.4434 (0.9); 6.4324 (0.8); 6.4273 (2.7); 5.2964
(1.2); 3.7848 (0.5); 3.7753 (16.0); 2.1886 (8.1); 2.1618 (0.7); 2.1541 (15.4); -0.0002 (7.1) (1.2); 3.7848 (0.5); 3.7753 (16.0); 2.1886 (8.1); 2.1618 (0.7); 2.1541 (15.4); -0.0002 (7.1)
1-258: lH-NMR(400.0 MHz, d6-DMSO):  1-258: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 8.6633 (16.0); 7.1234 (9.8); 7.1079 (3.4); 7.1039 (3.6); 5.7537 (2.2); 3.8627 (14.3); 3.3103 (35.3); 2.5234 (1.3); 2.5187 (1.8);δ = 8.6633 (16.0); 7.1234 (9.8); 7.1079 (3.4); 7.1039 (3.6); 5.7537 (2.2); 3.8627 (14.3); 3.3103 (35.3); 2.5234 (1.3); 2.5187 (1.8);
2.5100 (20.7); 2.5054 (43.3); 2.5008 (59.8); 2.4962 (40.8); 2.4916 (18.2); 0.0081 (0.6); -0.0002 (15.4) 2,5100 (20.7); 2.5054 (43.3); 2,5008 (59.8); 2.4962 (40.8); 2.4916 (18.2); 0.0081 (0.6); -0.0002 (15.4)
1-259: 1H-NMR(400.0 MHz, CDC13):  1-259: 1H-NMR (400.0 MHz, CDC13):
δ= 8.5671 (0.7); 8.5536 (1.1); 8.4799 (12.0); 7.2597 (39.4); 7.2314 (0.7); 7.2290 (1.1); 7.2247 (0.5); 7.2147 (0.6); 7.2109 (2.6); 7.2076 (1.5); 7.1955 (0.9); 7.1917 (2.1); 7.1902 (1.5); 7.1422 (0.6); 7.1390 (1.2); 7.1359 (0.8); 7.1204 (1.3); 7.1023 (0.6); 7.0449 (0.7); 7.0425 (2.3); 7.0392 (2.8); 7.0339 (0.7); 7.0255 (0.7); 7.0237 (0.9); 7.0214 (2.1); 7.0200 (1.3); 7.0184 (1.8); 5.2981 (0.7); 3.7698 (16.0); 3.6816 (1.8); 2.3232 (15.3); 2.3161 (1.1); 2.2691 (1.0); 2.2676 (1.0); 1.5429 (5.0); 0.0079 (0.5); -0.0002 (18.0) 1-260: 1H-NMR(400.0 MHz, CDC13): δ = 8.5671 (0.7); 8.5536 (1.1); 8.4799 (12.0); 7.2597 (39.4); 7.2314 (0.7); 7.2290 (1.1); 7.2247 (0.5); 7.2147 (0.6); 7.2109 (2.6); 7.2076 (1.5); 7.1955 (0.9); 7.1917 (2.1); 7.1902 (1.5); 7.1422 (0.6); 7.1390 (1.2); 7.1359 (0.8); 7.1204 (1.3); 7.1023 (0.6); 7.0449 (0.7); 7.0425 (2.3); 7.0392 (2.8); 7.0339 (0.7); 7.0255 (0.7); 7.0237 (0.9); 7.0214 (2.1); 7.0200 (1.3); 7.0184 (1.8); 5.2981 (0.7); 3.7698 (16.0); 3.6816 (1.8); 2.3232 (15.3); 2.3161 (1.1); 2.2691 (1.0); 2.2676 (1.0); 1.5429 (5.0); 0.0079 (0.5); -0.0002 (18.0) 1-260: 1H NMR (400.0 MHz, CDC13):
δ= 8.4550 (6.5); 8.4430 (6.6); 8.3423 (0.9); 8.3399 (1.1); 8.3362 (1.0); 8.3338 (1.1); 8.3315 (0.8); 7.4934 (0.7); 7.4923 (0.8); 7.4872 (0.7); 7.4861 (0.7); 7.4709 (0.8); 7.4698 (0.8); 7.4646 (0.8); 7.4636 (0.8); 7.2605 (48.9); 6.9929 (1.9); 6.9810 (3.6); 6.9690 (1.8); 6.5553 (1.3); 6.5538 (1.0); 6.5328 (1.3); 6.5313 (1.0); 5.2984 (1.0); 3.8328 (0.9); 3.8085 (16.0); 3.6854 (0.7);δ = 8.4550 (6.5); 8.4430 (6.6); 8.3423 (0.9); 8.3399 (1.1); 8.3362 (1.0); 8.3338 (1.1); 8.3315 (0.8); 7.4934 (0.7); 7.4923 (0.8); 7.4872 (0.7); 7.4861 (0.7); 7.4709 (0.8); 7.4698 (0.8); 7.4646 (0.8); 7.4636 (0.8); 7.2605 (48.9); 6.9929 (1.9); 6.9810 (3.6); 6.9690 (1.8); 6.5553 (1.3); 6.5538 (1.0); 6.5328 (1.3); 6.5313 (1.0); 5.2984 (1.0); 3.8328 (0.9); 3.8085 (16.0); 3.6854 (0.7);
3.2703 (13.7); 2.1255 (15.7); 2.0217 (0.7); 1.5538 (1.3); 1.2558 (0.6); 0.0079 (0.6); -0.0002 (19.1); -0.0085 (0.6) 3.2703 (13.7); 2.1255 (15.7); 2.0217 (0.7); 1.5538 (1.3); 1.2558 (0.6); 0.0079 (0.6); -0.0002 (19.1); -0.0085 (0.6)
1-261 : 1H-NMR(400.0 MHz, CDC13):  1-261: 1H NMR (400.0 MHz, CDC13):
δ= 8.4480 (0.8); 8.3277 (11.4); 7.2600 (42.6); 6.7242 (0.5); 6.7174 (0.6); 6.7031 (0.6); 6.6960 (1.0); 6.6886 (0.8); 6.6678 (0.6); 6.6362 (0.6); 6.6328 (0.6); 6.5563 (0.7); 6.5424 (0.7); 6.5321 (0.7); 6.5181 (0.8); 5.2980 (2.2); 4.7225 (0.7); 4.7168 (0.7); 3.7974δ = 8.4480 (0.8); 8.3277 (11.4); 7.2600 (42.6); 6.7242 (0.5); 6.7174 (0.6); 6.7031 (0.6); 6.6960 (1.0); 6.6886 (0.8); 6.6678 (0.6); 6.6362 (0.6); 6.6328 (0.6); 6.5563 (0.7); 6.5424 (0.7); 6.5321 (0.7); 6.5181 (0.8); 5.2980 (2.2); 4.7225 (0.7); 4.7168 (0.7); 3.7974
(0.7); 3.7811 (16.0); 3.5959 (1.0); 2.1763 (11.7); 1.9362 (0.7); 1.5458 (2.7); -0.0002 (16.4); -0.0085 (0.6) (0.7); 3.7811 (16.0); 3.5959 (1.0); 2.1763 (11.7); 1.9362 (0.7); 1.5458 (2.7); -0.0002 (16.4); -0.0085 (0.6)
1-262: 1H-NMR(400.0 MHz, CDC13):  1-262: 1H NMR (400.0 MHz, CDC13):
δ= 8.2924 (11.0); 7.2594 (12.3); 7.0953 (1.6); 7.0934 (0.6); 7.0902 (0.6); 7.0769 (2.2); 7.0739 (2.2); 7.0605 (0.6); 7.0555 (1.9); 6.7009 (0.9); 6.6982 (0.5); 6.6853 (0.7); 6.6826 (1.6); 6.6801 (0.8); 6.6643 (0.7); 6.5317 (2.1); 6.5289 (2.6); 6.5269 (1.3); 6.5238 (0.7); 6.5149 (0.6); 6.5125 (1.1); 6.5100 (2.4); 6.5074 (2.0); 5.2955 (0.8); 4.6388 (1.0); 3.7768 (16.0); 2.1630 (13.6); -0.0002δ = 8.2924 (11.0); 7.2594 (12.3); 7.0953 (1.6); 7.0934 (0.6); 7.0902 (0.6); 7.0769 (2.2); 7.0739 (2.2); 7.0605 (0.6); 7.0555 (1.9); 6.7009 (0.9); 6.6982 (0.5); 6.6853 (0.7); 6.6826 (1.6); 6.6801 (0.8); 6.6643 (0.7); 6.5317 (2.1); 6.5289 (2.6); 6.5269 (1.3); 6.5238 (0.7); 6.5149 (0.6); 6.5125 (1.1); 6.5100 (2.4); 6.5074 (2.0); 5.2955 (0.8); 4.6388 (1.0); 3.7768 (16.0); 2.1630 (13.6); -0.0002
(4.7) (4.7)
1-263: 1H-NMR(400.0 MHz, CDC13):  1-263: 1H NMR (400.0 MHz, CDC13):
δ= 7.5181 (1.0); 7.2592 (177.3); 7.2097 (0.7); 7.2002 (1.0); 7.1821 (2.3); 7.1633 (1.8); 7.1138 (0.9); 7.0963 (1.3); 7.0783 (0.6); 7.0470 (2.3); 7.0282 (1.9); 6.9952 (1.1); 3.8093 (14.1); 2.3336 (16.0); 1.2551 (0.7); 0.0080 (2.1); -0.0002 (66.3); -0.0085 (1.8) 1-265: lH-NMR(400.0 MHz, d6-DMSO): δ = 7.5181 (1.0); 7.2592 (177.3); 7.2097 (0.7); 7.2002 (1.0); 7.1821 (2.3); 7.1633 (1.8); 7.1138 (0.9); 7.0963 (1.3); 7.0.783 (0.6); 7.0470 (2.3); 7.0282 (1.9); 6.9952 (1.1); 3.8093 (14.1); 2.3336 (16.0); 1.2551 (0.7); 0.0080 (2.1); -0.0002 (66.3); -0.0085 (1.8) 1-265: 1H-NMR (400.0 MHz, d6-DMSO):
δ= 8.5950 (16.0); 7.0963 (0.9); 7.0796 (0.6); 7.0736 (2.8); 7.0683 (0.6); 7.0581 (0.5); 7.0517 (2.4); 7.0434 (2.4); 7.0368 (0.7); 7.0298 (2.5); 7.0206 (1.0); 7.0069 (0.8); 5.9434 (2.4); 3.5426 (12.8); 3.3090 (39.7); 2.8904 (1.5); 2.7315 (1.3); 2.7300 (1.4); 2.5230 (1.4); 2.5183 (2.0); 2.5096 (25.5); 2.5050 (54.1); 2.5004 (75.1); 2.4959 (51.5); 2.4913 (23.3); 2.0723 (1.8); 0.0080 (0.9); - 0.0002 (33.9); -0.0085 (1.0) 1-266: lH-NMR(400.0 MHz, d6-DMSO): δ = 8.5950 (16.0); 7.0963 (0.9); 7.0796 (0.6); 7.0736 (2.8); 7.0683 (0.6); 7.0581 (0.5); 7.0517 (2.4); 7.0434 (2.4); 7.0368 (0.7); 7.0298 (2.5); 7.0206 (1.0); 7.0069 (0.8); 5.9434 (2.4); 3.5426 (12.8); 3.3090 (39.7); 2.8904 (1.5); 2.7315 (1.3); 2.7300 (1.4); 2.5230 (1.4); 2.5183 (2.0); 2.5096 (25.5); 2.5050 (54.1); 2.5004 (75.1); 2.4959 (51.5); 2.4913 (23.3); 2.0723 (1.8); 0.0080 (0.9); - 0.0002 (33.9); -0.0085 (1.0) 1-266: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 8.7013 (9.9); 8.6078 (1.0); 7.2677 (0.8); 7.2494 (1.9); 7.2357 (0.6); 7.2311 (1.8); 7.1863 (1.3); 7.1815 (2.1); 7.1652 (1.6); 7.1637 (1.9); 7.1619 (1.8); 7.1579 (1.3); 7.1444 (1.6); 7.1351 (1.5); 7.1278 (0.8); 7.1220 (1.5); 7.0879 (1.4); 7.0657 (2.1); 7.0433 (0.8); 3.7021 (8.0); 3.6290 (0.7); 3.3094 (30.9); 2.5232 (1.7); 2.5186 (2.4); 2.5098 (25.5); 2.5053 (52.8); 2.5007 (72.5); 2.4961δ = 8.7013 (9.9); 8.6078 (1.0); 7.2677 (0.8); 7.2494 (1.9); 7.2357 (0.6); 7.2311 (1.8); 7.1863 (1.3); 7.1815 (2.1); 7.1652 (1.6); 7.1637 (1.9); 7.1619 (1.8); 7.1579 (1.3); 7.1444 (1.6); 7.1351 (1.5); 7.1278 (0.8); 7.1220 (1.5); 7.0879 (1.4); 7.0657 (2.1); 7.0433 (0.8); 3.7021 (8.0); 3.6290 (0.7); 3.3094 (30.9); 2.5232 (1.7); 2.5186 (2.4); 2.5098 (25.5); 2.5053 (52.8); 2,5007 (72.5); 2.4961
(49.4); 2.4916 (22.1); 2.2998 (7.6); 2.2166 (1.3); 2.2067 (16.0); 2.0587 (0.6); 0.0080 (1.6); -0.0002 (45.5); -0.0086 (1.2) (49.4); 2.4916 (22.1); 2.2998 (7.6); 2.2166 (1.3); 2.2067 (16.0); 2.0587 (0.6); 0.0080 (1.6); -0.0002 (45.5); -0.0086 (1.2)
1-267: 1H-NMR(400.0 MHz, CDC13):  1-267: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2970 (11.7); 8.2942 (1.3); 7.2605 (23.5); 7.1719 (1.0); 7.1520 (0.6); 6.9344 (0.7); 6.9325 (0.8); 6.9305 (0.7); 6.9153 (0.6); 6.9134 (0.7); 6.9115 (0.6); 6.7496 (0.7); 6.7481 (0.7); 6.7451 (1.1); 6.7438 (1.2); 6.7410 (0.9); 6.7395 (0.8); 6.7130 (0.7); 6.7117 (0.6); 6.7076 (0.5); 6.6927 (0.6); 6.6868 (0.5); 5.2978 (1.4); 4.8525 (0.8); 3.7978 (16.0); 3.7783 (1.0); 2.1634 (12.9); 2.0431δ = 8.2970 (11.7); 8.2942 (1.3); 7.2605 (23.5); 7.1719 (1.0); 7.1520 (0.6); 6.9344 (0.7); 6.9325 (0.8); 6.9305 (0.7); 6.9153 (0.6); 6.9134 (0.7); 6.9115 (0.6); 6.7496 (0.7); 6.7481 (0.7); 6.7451 (1.1); 6.7438 (1.2); 6.7410 (0.9); 6.7395 (0.8); 6.7130 (0.7); 6.7117 (0.6); 6.7076 (0.5); 6.6927 (0.6); 6.6868 (0.5); 5.2978 (1.4); 4.8525 (0.8); 3.7978 (16.0); 3.7783 (1.0); 2.1634 (12.9); 2.0431
(0.6); 1.5604 (1.8); -0.0002 (9.8); -0.0027 (0.6) (0.6); 1.5604 (1.8); -0.0002 (9.8); -0.0027 (0.6)
1-268: 1H-NMR(400.0 MHz, CDC13):  1-268: 1H NMR (400.0 MHz, CDC13):
δ= 8.3200 (11.0); 8.2942 (1.4); 7.2604 (21.6); 7.0335 (0.6); 7.0170 (0.6); 7.0131 (1.2); 6.9965 (1.3); 6.9927 (0.7); 6.9762 (0.6); 6.3734 (0.6); 6.3720 (0.6); 6.3674 (0.6); 6.3660 (0.7); 6.3186 (0.8); 6.3164 (0.8); 6.3130 (1.0); 6.3109 (0.9); 6.2982 (0.8); 6.2961 (0.8); 6.2926 (1.0); 6.2905 (0.9); 6.2456 (0.7); 6.2398 (1.1); 6.2341 (0.5); 6.2172 (0.7); 6.2113 (1.1); 6.2056 (0.6); 3.7831 (16.0);δ = 8.3200 (11.0); 8.2942 (1.4); 7.2604 (21.6); 7.0335 (0.6); 7.0170 (0.6); 7.0131 (1.2); 6.9965 (1.3); 6.9927 (0.7); 6.9762 (0.6); 6.3734 (0.6); 6.3720 (0.6); 6.3674 (0.6); 6.3660 (0.7); 6.3186 (0.8); 6.3164 (0.8); 6.3130 (1.0); 6.3109 (0.9); 6.2982 (0.8); 6.2961 (0.8); 6.2926 (1.0); 6.2905 (0.9); 6.2456 (0.7); 6.2398 (1.1); 6.2341 (0.5); 6.2172 (0.7); 6.2113 (1.1); 6.2056 (0.6); 3.7831 (16.0);
3.7791 (2.6); 2.1663 (15.8); -0.0002 (8.8) 3.7791 (2.6); 2.1663 (15.8); -0.0002 (8.8)
1-269: 1H-NMR(400.0 MHz, CDC13):  1-269: 1H NMR (400.0 MHz, CDC13):
δ= 8.3220 (11.8); 8.2940 (1.0); 7.2602 (27.7); 7.0021 (1.1); 6.9820 (2.2); 6.9620 (1.4); 6.6590 (0.9); 6.6567 (1.0); 6.6540 (1.0); 6.6518 (1.0); 6.6393 (0.8); 6.6370 (0.9); 6.6343 (1.0); 6.6321 (0.9); 6.5200 (1.3); 6.5147 (2.3); 6.5095 (1.4); 6.4302 (1.0); 6.4280δ = 8.3220 (11.8); 8.2940 (1.0); 7.2602 (27.7); 7.0021 (1.1); 6.9820 (2.2); 6.9620 (1.4); 6.6590 (0.9); 6.6567 (1.0); 6.6540 (1.0); 6.6518 (1.0); 6.6393 (0.8); 6.6370 (0.9); 6.6343 (1.0); 6.6321 (0.9); 6.5200 (1.3); 6.5147 (2.3); 6.5095 (1.4); 6.4302 (1.0); 6.4280
(1.0) ; 6.4244 (0.9); 6.4222 (0.9); 6.4097 (0.9); 6.4075 (0.9); 6.4039 (0.8); 6.4017 (0.8); 4.7234 (1.0); 3.7867 (16.0); 3.7784 (1.5);(1.0); 6.4244 (0.9); 6.4222 (0.9); 6.4097 (0.9); 6.4075 (0.9); 6.4039 (0.8); 6.4017 (0.8); 4.7234 (1.0); 3.7867 (16.0); 3.7784 (1.5);
2.1644 (11.5); 2.0431 (0.9); 1.5546 (6.5); 1.2583 (0.6); -0.0002 (12.3) 2.1644 (11.5); 2.0431 (0.9); 1.5546 (6.5); 1.2583 (0.6); -0.0002 (12.3)
1-270: 1H-NMR(400.0 MHz, CDC13):  1-270: 1H NMR (400.0 MHz, CDC13):
δ= 8.5538 (0.6); 8.4985 (11.9); 7.2602 (37.6); 7.0589 (1.6); 7.0534 (0.7); 7.0462 (1.7); 7.0421 (0.9); 7.0407 (0.8); 7.0364 (2.5); 7.0293 (0.9); 7.0238 (2.4); 6.9480 (2.6); 6.9423 (0.7); 6.9311 (0.7); 6.9268 (3.3); 6.9258 (2.6); 6.9212 (0.8); 6.9100 (0.6); 6.9044δ = 8.5538 (0.6); 8.4985 (11.9); 7.2602 (37.6); 7.0589 (1.6); 7.0534 (0.7); 7.0462 (1.7); 7.0421 (0.9); 7.0407 (0.8); 7.0364 (2.5); 7.0293 (0.9); 7.0238 (2.4); 6.9480 (2.6); 6.9423 (0.7); 6.9311 (0.7); 6.9268 (3.3); 6.9258 (2.6); 6.9212 (0.8); 6.9100 (0.6); 6.9044
(1.7); 3.7568 (16.0); 3.6819 (1.0); 2.3260 (15.4); 2.2694 (0.5); 2.2678 (0.6); 1.5436 (11.0); 0.0080 (0.5); -0.0002 (17.0) (1.7); 3.7568 (16.0); 3.6819 (1.0); 2.3260 (15.4); 2.2694 (0.5); 2.2678 (0.6); 1.5436 (11.0); 0.0080 (0.5); -0.0002 (17.0)
1-271 : 1H-NMR(400.0 MHz, CDC13):  1-271: 1H NMR (400.0 MHz, CDC13):
δ= 8.2948 (0.7); 8.2436 (10.2); 7.2594 (31.5); 7.1338 (1.7); 7.1315 (0.6); 7.1285 (0.6); 7.1156 (2.1); 7.1117 (2.1); 7.0987 (0.6); 7.0959 (0.7); 7.0936 (2.0); 6.6908 (0.8); 6.6882 (0.5); 6.6752 (0.6); 6.6727 (1.5); 6.6702 (0.8); 6.6544 (0.7); 6.6172 (1.8); 6.6145 (2.2); 6.6123 (1.1); 6.6092 (0.6); 6.6001 (0.6); 6.5977 (1.0); 6.5950 (2.1); 6.5925 (1.7); 3.7763 (16.0); 3.0717 (15.6); 2.1651δ = 8.2948 (0.7); 8.2436 (10.2); 7.2594 (31.5); 7.1338 (1.7); 7.1315 (0.6); 7.1285 (0.6); 7.1156 (2.1); 7.1117 (2.1); 7.0987 (0.6); 7.0959 (0.7); 7.0936 (2.0); 6.6908 (0.8); 6.6882 (0.5); 6.6752 (0.6); 6.6727 (1.5); 6.6702 (0.8); 6.6544 (0.7); 6.6172 (1.8); 6.6145 (2.2); 6.6123 (1.1); 6.6092 (0.6); 6.6001 (0.6); 6,577 (1.0); 6.5950 (2.1); 6.5925 (1.7); 3.7763 (16.0); 3.0717 (15.6); 2.1651
(1.1) ; 2.0839 (15.4); -0.0002 (13.2) (1.1); 2.0839 (15.4); -0.0002 (13.2)
1-272: 1H-NMR(400.0 MHz, CDC13):  1-272: 1H NMR (400.0 MHz, CDC13):
δ= 8.5538 (1.0); 8.5425 (11.8); 7.2607 (30.3); 7.0663 (0.6); 7.0450 (0.9); 7.0414 (0.7); 7.0247 (0.7); 7.0201 (0.9); 6.9999 (0.6); 6.8681 (0.6); 6.8624 (0.7); 6.8501 (0.6); 6.8444 (0.8); 6.8419 (0.6); 6.8361 (0.7); 6.8183 (0.7); 6.8155 (0.6); 6.8119 (0.6); 6.8056 (0.8); 6.8019 (0.6); 6.7842 (0.7); 5.2987 (0.7); 3.7681 (16.0); 3.6820 (1.6); 2.6817 (1.2); 2.3180 (15.2); 2.2695 (0.9); 2.2680δ = 8.5538 (1.0); 8.5425 (11.8); 7.2607 (30.3); 7.0663 (0.6); 7.0450 (0.9); 7.0414 (0.7); 7.0247 (0.7); 7.0201 (0.9); 6.9999 (0.6); 6.8681 (0.6); 6.8624 (0.7); 6.8501 (0.6); 6.8444 (0.8); 6.8419 (0.6); 6.8361 (0.7); 6.8183 (0.7); 6.8155 (0.6); 6.8119 (0.6); 6.8056 (0.8); 6.8019 (0.6); 6.7842 (0.7); 5.2987 (0.7); 3.7681 (16.0); 3.6820 (1.6); 2.6817 (1.2); 2.3180 (15.2); 2.2695 (0.9); 2.2680
(0.9); 1.5480 (4.5); -0.0002 (13.7) (0.9); 1.5480 (4.5); -0.0002 (13.7)
1-273: 1H-NMR(400.0 MHz, CDC13):  1-273: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2942 (0.6); 8.2765 (11.4); 8.2430 (1.4); 7.2603 (24.3); 7.0700 (0.6); 7.0528 (0.6); 7.0494 (1.1); 7.0322 (1.1); 7.0289 (0.7); 7.0116 (0.6); 6.3864 (0.7); 6.3848 (0.9); 6.3830 (0.8); 6.3807 (0.9); 6.3787 (1.0); 6.3642 (0.9); 6.3617 (1.2); 6.3582 (1.1); 6.3564 (0.7); 6.3271 (0.7); 6.3212 (1.0); 6.2961 (0.6); 6.2901 (1.0); 5.2977 (0.9); 3.7811 (16.0); 3.7758 (2.4); 3.0713 (2.3); 3.0658δ = 8.2942 (0.6); 8.2765 (11.4); 8.2430 (1.4); 7.2603 (24.3); 7.0700 (0.6); 7.0528 (0.6); 7.0494 (1.1); 7.0322 (1.1); 7.0289 (0.7); 7.0116 (0.6); 6.3864 (0.7); 6.3848 (0.9); 6.3830 (0.8); 6.3807 (0.9); 6.3787 (1.0); 6.3642 (0.9); 6.3617 (1.2); 6.3582 (1.1); 6.3564 (0.7); 6.3271 (0.7); 6.3212 (1.0); 6.2961 (0.6); 6.2901 (1.0); 5.2977 (0.9); 3.7811 (16.0); 3.7758 (2.4); 3.0713 (2.3); 3.0658
(15.7); 2.1647 (0.8); 2.0899 (15.2); 2.0837 (2.2); 1.5587 (3.6); -0.0002 (10.0) (15.7); 2.1647 (0.8); 2.0899 (15.2); 2.0837 (2.2); 1.5587 (3.6); -0.0002 (10.0)
1-274: 1H-NMR(400.0 MHz, CDC13):  1-274: 1H NMR (400.0 MHz, CDC13):
δ= 8.3030 (11.5); 8.2746 (1.0); 8.2709 (0.9); 8.2433 (0.8); 8.2220 (0.8); 7.2611 (42.4); 3.8623 (16.0); 2.3389 (15.8); 1.5598 (4.7);δ = 8.3030 (11.5); 8.2746 (1.0); 8.2709 (0.9); 8.2433 (0.8); 8.2220 (0.8); 7.2611 (42.4); 3.8623 (16.0); 2.3389 (15.8); 1.5598 (4.7);
-0.0002 (18.4); -0.0085 (0.5) -0.0002 (18.4); -0.0085 (0.5)
1-275: 1H-NMR(400.0 MHz, CDC13):  1-275: 1H NMR (400.0 MHz, CDC13):
δ= 8.4515 (0.6); 8.2806 (10.2); 7.9522 (1.2); 7.9484 (1.2); 7.9327 (1.2); 7.9288 (1.2); 7.3248 (0.6); 7.3209 (0.6); 7.3064 (0.8); 7.3037 (1.0); 7.3007 (0.8); 7.2862 (0.9); 7.2823 (0.8); 7.2626 (11.4); 7.1244 (0.8); 7.1217 (0.9); 7.1044 (1.2); 7.1029 (1.2); 7.0867 (0.6); 7.0839 (0.7); 7.0169 (1.4); 7.0143 (1.4); 6.9966 (1.2); 6.9939 (1.2); 5.2979 (1.1); 3.8947 (16.0); 3.8651 (14.0);δ = 8.4515 (0.6); 8.2806 (10.2); 7.9522 (1.2); 7.9484 (1.2); 7.9327 (1.2); 7.9288 (1.2); 7.3248 (0.6); 7.3209 (0.6); 7.3064 (0.8); 7.3037 (1.0); 7.3007 (0.8); 7.2862 (0.9); 7.2823 (0.8); 7.2626 (11.4); 7.1244 (0.8); 7.1217 (0.9); 7.1044 (1.2); 7.1029 (1.2); 7.0867 (0.6); 7.0839 (0.7); 7.0169 (1.4); 7.0143 (1.4); 6.9966 (1.2); 6.9939 (1.2); 5.2979 (1.1); 3.8947 (16.0); 3.8651 (14.0);
3.7484 (1.0); 2.2912 (0.7); 2.2679 (13.8); 1.5677 (2.4); -0.0002 (5.0) 3.7484 (1.0); 2.2912 (0.7); 2.2679 (13.8); 1.5677 (2.4); -0.0002 (5.0)
1-276: lH-NMR(400.0 MHz, CDC13):  1-276: 1 H NMR (400.0 MHz, CDC13):
δ= 8.3423 (11.9); 7.2611 (19.0); 6.1450 (0.7); 6.1279 (0.7); 6.1223 (1.4); 6.1167 (0.8); 6.0995 (0.7); 6.0619 (1.6); 6.0592 (0.8); 6.0564 (1.7); 6.0424 (0.6); 6.0401 (0.7); 6.0375 (2.0); 6.0345 (0.6); 6.0320 (1.3); 4.8770 (0.9); 3.7853 (16.0); 2.1679 (10.9);δ = 8.3423 (11.9); 7.2611 (19.0); 6.1450 (0.7); 6.1279 (0.7); 6.1223 (1.4); 6.1167 (0.8); 6.0995 (0.7); 6.0619 (1.6); 6: 0592 (0.8); 6.0564 (1.7); 6.0424 (0.6); 6.0401 (0.7); 6.0375 (2.0); 6.0345 (0.6); 6.0320 (1.3); 4.8770 (0.9); 3.7853 (16.0); 2.1679 (10.9);
2.0431 (0.5); 1.5634 (5.1); -0.0002 (8.0) 2.0431 (0.5); 1.5634 (5.1); -0.0002 (8.0)
1-277: 1H-NMR(400.0 MHz, CDC13):  1-277: 1H NMR (400.0 MHz, CDC13):
δ= 8.4435 (0.7); 8.3111 (10.4); 8.0515 (4.3); 8.0292 (4.1); 7.2618 (15.5); 7.1619 (4.6); 7.1397 (4.0); 5.2990 (1.4); 3.8729 (16.0);δ = 8.4435 (0.7); 8.3111 (10.4); 8.0515 (4.3); 8.0292 (4.1); 7.2618 (15.5); 7.1619 (4.6); 7.1397 (4.0); 5.2990 (1.4); 3.8729 (16.0);
3.8298 (1.2); 2.3292 (1.3); 2.2978 (15.7); 1.5545 (5.0); -0.0002 (6.9) 3.8298 (1.2); 2.3292 (1.3); 2.2978 (15.7); 1.5545 (5.0); -0.0002 (6.9)
1-278: 1H-NMR(400.0 MHz, CDC13):  1-278: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2824 (7.6); 7.2609 (9.9); 7.0986 (1.0); 7.0787 (1.8); 7.0570 (1.2); 6.6555 (1.8); 6.6348 (1.7); 6.6219 (2.0); 6.6142 (2.4);δ = 8.2824 (7.6); 7.2609 (9.9); 7.0986 (1.0); 7.0.787 (1.8); 7.0570 (1.2); 6.6555 (1.8); 6.6348 (1.7); 6.6219 (2.0); 6.6142 (2.4);
6.6090 (3.6); 6.6057 (3.5); 5.2973 (0.7); 3.8271 (14.6); 3.7321 (16.0); 2.3082 (14.8); 1.5634 (1.5); -0.0002 (4.4) 6.6090 (3.6); 6.6057 (3.5); 5.2973 (0.7); 3.8271 (14.6); 3.7321 (16.0); 2.3082 (14.8); 1.5634 (1.5); -0.0002 (4.4)
1-279: 1H-NMR(400.0 MHz, CDC13):  1-279: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2453 (11.3); 7.2600 (20.2); 7.0283 (0.5); 7.0181 (0.7); 7.0141 (1.2); 7.0123 (1.6); 7.0103 (1.8); 7.0089 (1.5); 7.0048 (0.6); 7.0036 (0.5); 6.9948 (2.0); 6.9936 (1.8); 6.9892 (2.3); 6.9858 (0.9); 6.9736 (0.8); 6.8945 (1.2); 6.8890 (1.2); 6.8771 (0.5); 6.8748 (0.6); 6.8736 (0.6); 6.8724 (0.6); 6.8717 (0.6); 3.8416 (16.0); 2.2910 (15.8); 2.2618 (9.6); 2.0434 (1.0); 1.5537 (1.9); 1.2584δ = 8.2453 (11.3); 7.2600 (20.2); 7.0283 (0.5); 7.0181 (0.7); 7.0141 (1.2); 7.0123 (1.6); 7.0103 (1.8); 7.0089 (1.5); 7.0048 (0.6); 7.0036 (0.5); 6.9948 (2.0); 6.9936 (1.8); 6.9892 (2.3); 6.9858 (0.9); 6.9736 (0.8); 6.8945 (1.2); 6.8890 (1.2); 6.8771 (0.5); 6.8748 (0.6); 6.8736 (0.6); 6.8724 (0.6); 6.8717 (0.6); 3.8416 (16.0); 2.2910 (15.8); 2.2618 (9.6); 2.0434 (1.0); 1.5537 (1.9); 1.2584
(0.8); 0.8817 (0.6); -0.0002 (11.8) (0.8); 0.8817 (0.6); -0.0002 (11.8)
1-280: 1H-NMR(400.0 MHz, CDC13):  1-280: 1H NMR (400.0 MHz, CDC13):
δ= 8.4985 (6.1); 8.4865 (6.3); 7.2671 (0.6); 7.2597 (67.2); 7.0107 (1.0); 6.9957 (1.1); 6.9901 (3.3); 6.9798 (2.0); 6.9679 (5.2); 6.9559 (2.1); 6.9501 (1.0); 3.7279 (16.0); 3.5797 (4.3); 3.5200 (1.0); 2.3425 (0.5); 2.2492 (7.7); 2.1399 (13.5); 1.5484 (1.3); 0.0079 (1.1); -0.0002 (34.6); -0.0085 (0.9) 1-281 : 1H-NMR(400.0 MHz, CDC13): δ = 8.4985 (6.1); 8.4865 (6.3); 7.2671 (0.6); 7.2597 (67.2); 7.0107 (1.0); 6.9957 (1.1); 6.9901 (3.3); 6.9798 (2.0); 6.9679 (5.2); 6.9559 (2.1); 6.9501 (1.0); 3.7279 (16.0); 3.5797 (4.3); 3.5200 (1.0); 2.3425 (0.5); 2.2492 (7.7); 2.1399 (13.5); 1.5484 (1.3); 0.0079 (1.1); -0.0002 (34.6); -0.0085 (0.9) 1-281: 1H NMR (400.0 MHz, CDC13):
δ= 8.4942 (5.0); 8.4822 (5.1); 7.2611 (25.0); 7.0527 (0.8); 7.0364 (0.8); 6.9967 (1.9); 6.9847 (3.5); 6.9727 (1.7); 6.6774 (0.6); 6.6613 (0.6); 6.6549 (0.7); 6.6527 (0.8); 6.6416 (0.5); 6.6392 (0.5); 6.6359 (0.6); 6.6303 (0.7); 6.6208 (0.8); 6.6187 (0.7); 6.6141δ = 8.4942 (5.0); 8.4822 (5.1); 7.2611 (25.0); 7.0527 (0.8); 7.0364 (0.8); 6.9967 (1.9); 6.9847 (3.5); 6.9727 (1.7); 6.6774 (0.6); 6.6613 (0.6); 6.6549 (0.7); 6.6527 (0.8); 6.6416 (0.5); 6.6392 (0.5); 6.6359 (0.6); 6.6303 (0.7); 6.6208 (0.8); 6.6187 (0.7); 6.6141
(0.5); 6.6121 (0.6); 3.7453 (16.0); 3.6002 (3.7); 2.2055 (12.6); -0.0002 (13.6) (0.5); 6.6121 (0.6); 3.7453 (16.0); 3.6002 (3.7); 2.2055 (12.6); -0.0002 (13.6)
1-282: 1H-NMR(400.0 MHz, CDC13):  1-282: 1H-NMR (400.0 MHz, CDC13):
δ= 8.5000 (6.0); 8.4881 (6.2); 7.2617 (16.0); 6.9953 (1.8); 6.9833 (3.5); 6.9713 (1.7); 6.8585 (0.9); 6.8472 (0.9); 6.8359 (0.5); 6.8247 (0.5); 6.7724 (0.7); 6.7643 (0.8); 6.7562 (0.6); 6.7547 (0.6); 6.7452 (0.5); 6.7352 (0.6); 3.7579 (16.0); 3.6243 (3.3);δ = 8.5000 (6.0); 8.4881 (6.2); 7.2617 (16.0); 6.9953 (1.8); 6.9833 (3.5); 6.9713 (1.7); 6.8585 (0.9); 6.8472 (0.9); 6.8359 (0.5); 6.8247 (0.5); 6.7724 (0.7); 6.7643 (0.8); 6.7562 (0.6); 6.7547 (0.6); 6.7452 (0.5); 6.7352 (0.6); 3.7579 (16.0); 3.6243 (3.3);
2.2044 (11.4); -0.0002 (8.5) 2.2044 (11.4); -0.0002 (8.5)
1-283: 1H-NMR(400.0 MHz, CDC13):  1-283: 1H NMR (400.0 MHz, CDC13):
δ= 8.5075 (6.2); 8.4955 (6.5); 7.2654 (0.6); 7.2605 (37.6); 7.0070 (1.8); 6.9950 (3.5); 6.9831 (1.8); 6.9435 (1.0); 6.9386 (0.5); 6.9229 (0.7); 6.9178 (1.0); 6.8974 (0.9); 3.7534 (16.0); 3.7482 (0.7); 3.5879 (3.7); 2.1591 (13.4); 1.5564 (0.9); 0.0079 (0.6); -δ = 8.5075 (6.2); 8.4955 (6.5); 7.2654 (0.6); 7.2605 (37.6); 7.0070 (1.8); 6.9950 (3.5); 6.9831 (1.8); 6.9435 (1.0); 6.9386 (0.5); 6.9229 (0.7); 6.9178 (1.0); 6.8974 (0.9); 3.7534 (16.0); 3.7482 (0.7); 3.5879 (3.7); 2.1591 (13.4); 1.5564 (0.9); 0.0079 (0.6); -
0.0002 (20.2); -0.0085 (0.6) 0.0002 (20.2); -0.0085 (0.6)
1-284: 1H-NMR(400.0 MHz, CDC13):  1-284: 1H NMR (400.0 MHz, CDC13):
δ= 8.5029 (6.2); 8.4909 (6.2); 8.1195 (1.2); 8.1130 (1.2); 7.5186 (1.2); 7.4493 (0.9); 7.4430 (1.0); 7.4288 (1.1); 7.4224 (1.0); 7.2598 (181.8); 7.2101 (0.6); 7.1352 (1.6); 7.1159 (1.3); 7.0233 (1.9); 7.0114 (3.6); 6.9994 (1.8); 6.9958 (1.0); 3.7521 (16.0); 3.6382 (0.7); 3.6163 (5.0); 3.5745 (2.3); 2.1746 (13.7); 2.0757 (1.7); 1.5410 (1.7); 0.0080 (3.1); -0.0002 (97.8); -0.0085 (2.7) 1-285: 1H-NMR(400.0 MHz, CDC13): δ = 8.5029 (6.2); 8.4909 (6.2); 8.1195 (1.2); 8.1130 (1.2); 7.5186 (1.2); 7.4493 (0.9); 7.4430 (1.0); 7.4288 (1.1); 7.4224 (1.0); 7.2598 (181.8); 7.2101 (0.6); 7.1352 (1.6); 7.1159 (1.3); 7.0233 (1.9); 7.0114 (3.6); 6.9994 (1.8); 6.9958 (1.0); 3.7521 (16.0); 3.6382 (0.7); 3.6163 (5.0); 3.5745 (2.3); 2.1746 (13.7); 2.0757 (1.7); 1.5410 (1.7); 0.0080 (3.1); -0.0002 (97.8); -0.0085 (2.7) 1-285: 1H NMR (400.0 MHz, CDC13):
δ= 8.4689 (5.9); 8.4569 (6.0); 7.3323 (1.8); 7.3309 (1.8); 7.3281 (1.8); 7.3120 (0.9); 7.3083 (1.1); 7.2951 (1.0); 7.2766 (0.8);δ = 8.4689 (5.9); 8.4569 (6.0); 7.3323 (1.8); 7.3309 (1.8); 7.3281 (1.8); 7.3120 (0.9); 7.3083 (1.1); 7.2951 (1.0); 7.2766 (0.8);
7.2621 (11.9); 6.9711 (1.8); 6.9592 (3.5); 6.9472 (1.7); 3.7591 (16.0); 3.6938 (4.8); 2.1699 (13.7); -0.0002 (6.2) 7.2621 (11.9); 6.9711 (1.8); 6.9592 (3.5); 6.9472 (1.7); 3.7591 (16.0); 3.6938 (4.8); 2.1699 (13.7); -0.0002 (6.2)
1-286: 1H-NMR(400.0 MHz, CDC13):  1-286: 1H NMR (400.0 MHz, CDC13):
δ= 8.5139 (6.0); 8.5019 (6.2); 7.2612 (21.8); 7.0083 (1.8); 6.9963 (3.6); 6.9843 (1.8); 6.6454 (0.9); 6.6430 (0.8); 6.6411 (1.0); 6.6396 (1.2); 6.6356 (0.6); 6.6287 (0.5); 6.6244 (1.1); 6.6229 (1.0); 6.6211 (0.8); 6.6186 (1.0); 6.5383 (0.5); 6.5325 (0.9); 3.7607δ = 8.5139 (6.0); 8.5019 (6.2); 7.2612 (21.8); 7.0083 (1.8); 6.9963 (3.6); 6.9843 (1.8); 6.6454 (0.9); 6.6430 (0.8); 6.6411 (1.0); 6.6396 (1.2); 6.6356 (0.6); 6.6287 (0.5); 6.6244 (1.1); 6.6229 (1.0); 6.6211 (0.8); 6.6186 (1.0); 6.5383 (0.5); 6.5325 (0.9); 3.7607
(16.0); 3.6121 (4.6); 2.1667 (13.6); -0.0002 (12.0) (16.0); 3.6121 (4.6); 2.1667 (13.6); -0.0002 (12.0)
1-287: 1H-NMR(400.0 MHz, CDC13):  1-287: 1H NMR (400.0 MHz, CDC13):
δ= 8.3454 (11.0); 7.2658 (0.6); 7.2608 (32.4); 6.9627 (1.0); 6.9579 (0.5); 6.9421 (0.7); 6.9371 (1.0); 6.9165 (0.7); 6.8216 (0.5); 5.7616 (0.5); 5.7598 (0.6); 3.7482 (16.0); 3.7188 (3.0); 3.7098 (0.7); 3.6341 (0.9); 3.5886 (4.1); 2.2817 (1.7); 2.2802 (1.7);δ = 8.3454 (11.0); 7.2658 (0.6); 7.2608 (32.4); 6.9627 (1.0); 6.9579 (0.5); 6.9421 (0.7); 6.9371 (1.0); 6.9165 (0.7); 6.8216 (0.5); 5.7616 (0.5); 5.7598 (0.6); 3.7482 (16.0); 3.7188 (3.0); 3.7098 (0.7); 3.6341 (0.9); 3.5886 (4.1); 2.2817 (1.7); 2.2802 (1.7);
2.2704 (0.8); 2.2196 (1.0); 2.1943 (0.6); 2.1932 (0.6); 2.1596 (13.6); 0.0080 (0.5); -0.0002 (17.2) 2.2704 (0.8); 2.2196 (1.0); 2.1943 (0.6); 2.1932 (0.6); 2.1596 (13.6); 0.0080 (0.5); -0.0002 (17.2)
1-288: 1H-NMR(400.0 MHz, CDC13):  1-288: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3420 (11.1); 8.3056 (0.7); 8.3028 (0.7); 7.2670 (0.6); 7.2662 (0.7); 7.2604 (50.5); 6.6345 (0.9); 6.6321 (0.8); 6.6302 (1.0); 6.6288 (1.2); 6.6179 (0.6); 6.6136 (1.1); 6.6121 (1.0); 6.6104 (0.9); 6.6078 (1.0); 6.5562 (0.6); 6.5504 (0.9); 5.7688 (0.7); 5.7670 (0.8); 4.0674 (0.7); 4.0623 (0.7); 3.7566 (16.0); 3.7211 (4.0); 3.7153 (1.1); 3.6385 (1.8); 3.6117 (4.6); 3.5885 (1.5); 2.2831 (2.2); 2.2817 (2.3); 2.2724 (0.9); 2.2226 (1.6); 2.1930 (1.0); 2.1917 (1.0); 2.1728 (13.7); 0.0079 (0.9); -0.0002 (27.5); -0.0085 (0.7) 1-289: 1H-NMR(400.0 MHz, CDC13): δ = 8.3420 (11.1); 8.3056 (0.7); 8.3028 (0.7); 7.2670 (0.6); 7.2662 (0.7); 7.2604 (50.5); 6.6345 (0.9); 6.6321 (0.8); 6.6302 (1.0); 6.6288 (1.2); 6.6179 (0.6); 6.6136 (1.1); 6.6121 (1.0); 6.6104 (0.9); 6.6078 (1.0); 6.5562 (0.6); 6.5504 (0.9); 5.7688 (0.7); 5.7670 (0.8); 4.0674 (0.7); 4.0623 (0.7); 3.7566 (16.0); 3.7211 (4.0); 3.7153 (1.1); 3.6385 (1.8); 3.6117 (4.6); 3.5885 (1.5); 2.2831 (2.2); 2.2817 (2.3); 2.2724 (0.9); 2.2226 (1.6); 2.1930 (1.0); 2.1917 (1.0); 2.1728 (13.7); 0.0079 (0.9); -0.0002 (27.5); -0.0085 (0.7) 1-289: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3214 (10.8); 7.2607 (21.6); 6.8654 (0.7); 6.8541 (0.6); 6.7767 (0.6); 6.7747 (0.6); 6.7731 (0.6); 6.7667 (0.8); 6.7585 (0.9);δ = 8.3214 (10.8); 7.2607 (21.6); 6.8654 (0.7); 6.8541 (0.6); 6.7767 (0.6); 6.7747 (0.6); 6.7731 (0.6); 6.7667 (0.8); 6.7585 (0.9);
6.7523 (0.8); 6.7509 (0.9); 6.7494 (0.8); 6.7305 (0.6); 3.7547 (16.0); 3.6208 (3.3); 2.2149 (11.4); -0.0002 (11.8) 6.7523 (0.8); 6.7509 (0.9); 6.7494 (0.8); 6.7305 (0.6); 3.7547 (16.0); 3.6208 (3.3); 2.2149 (11.4); -0.0002 (11.8)
1-290: 1H-NMR(400.0 MHz, CDC13):  1-290: 1 H NMR (400.0 MHz, CDC13):
δ= 8.3287 (10.8); 7.2603 (43.9); 7.0380 (0.7); 7.0218 (0.7); 6.6925 (0.6); 6.6685 (0.7); 6.6642 (0.6); 6.6437 (1.1); 3.7408 (16.0); 3.7000 (1.8); 3.6919 (0.7); 3.6303 (2.0); 3.5985 (3.4); 2.2602 (1.0); 2.2587 (1.0); 2.2505 (0.7); 2.2091 (11.3); 2.2011 (0.7);δ = 8.3287 (10.8); 7.2603 (43.9); 7.0380 (0.7); 7.0218 (0.7); 6.6925 (0.6); 6.6685 (0.7); 6.6642 (0.6); 6.6437 (1.1); 3.7408 (16.0); 3.7000 (1.8); 3.6919 (0.7); 3.6303 (2.0); 3.5985 (3.4); 2.2602 (1.0); 2.2587 (1.0); 2.2505 (0.7); 2.2091 (11.3); 2.2011 (0.7);
0.0080 (0.7); -0.0002 (24.5); -0.0085 (0.7) 0.0080 (0.7); -0.0002 (24.5); -0.0085 (0.7)
1-291 : 1H-NMR(400.0 MHz, CDC13):  1-291: 1H NMR (400.0 MHz, CDC13):
δ= 8.2862 (11.2); 7.3599 (0.6); 7.3555 (0.8); 7.3131 (2.0); 7.3019 (2.7); 7.2995 (3.0); 7.2861 (1.0); 7.2624 (33.9); 3.7619 (16.0);δ = 8.2862 (11.2); 7.3599 (0.6); 7.3555 (0.8); 7.3131 (2.0); 7.3019 (2.7); 7.2995 (3.0); 7.2861 (1.0); 7.2624 (33.9); 3.7619 (16.0);
3.6948 (5.2); 2.1888 (13.8); 1.5655 (3.1); -0.0002 (11.8) 3.6948 (5.2); 2.1888 (13.8); 1.5655 (3.1); -0.0002 (11.8)
1-292: 1H-NMR(400.0 MHz, CDC13):  1-292: 1H NMR (400.0 MHz, CDC13):
δ= 8.4906 (5.0); 8.4787 (5.0); 7.2607 (20.2); 7.0950 (0.8); 7.0942 (0.9); 7.0747 (1.8); 7.0552 (1.0); 7.0545 (1.0); 7.0021 (1.5); 6.9901 (2.9); 6.9781 (1.4); 6.6802 (0.7); 6.6780 (0.9); 6.6758 (1.0); 6.6737 (1.0); 6.6608 (0.6); 6.6586 (0.7); 6.6565 (1.0); 6.6542 (1.0); 6.6416 (1.0); 6.6363 (1.5); 6.6317 (1.0); 6.6197 (1.0); 6.6176 (1.0); 6.6135 (0.6); 6.6113 (0.5); 6.5994 (0.8); 6.5972 (0.8);δ = 8.4906 (5.0); 8.4787 (5.0); 7.2607 (20.2); 7.0950 (0.8); 7.0942 (0.9); 7.0747 (1.8); 7.0552 (1.0); 7.0545 (1.0); 7.0021 (1.5); 6.9901 (2.9); 6.9781 (1.4); 6.6802 (0.7); 6.6780 (0.9); 6.6758 (1.0); 6.6737 (1.0); 6.6608 (0.6); 6.6586 (0.7); 6.6565 (1.0); 6.6542 (1.0); 6.6416 (1.0); 6.6363 (1.5); 6.6317 (1.0); 6.6197 (1.0); 6.6176 (1.0); 6.6135 (0.6); 6.6113 (0.5); 6.5994 (0.8); 6,55972 (0.8);
6.5931 (0.6); 6.5910 (0.6); 3.8414 (12.9); 3.7278 (16.0); 2.3050 (12.8); 1.5607 (3.6); -0.0002 (10.6) 6.5931 (0.6); 6.5910 (0.6); 3.8414 (12.9); 3.7278 (16.0); 2.3050 (12.8); 1.5607 (3.6); -0.0002 (10.6)
1-293: 1H-NMR(400.0 MHz, CDC13):  1-293: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3194 (10.6); 7.2602 (17.9); 7.1349 (2.7); 7.1300 (1.0); 7.1188 (1.2); 7.1138 (4.2); 7.1078 (0.6); 7.0353 (3.3); 7.0140 (2.1);δ = 8.3194 (10.6); 7.2602 (17.9); 7.1349 (2.7); 7.1300 (1.0); 7.1188 (1.2); 7.1138 (4.2); 7.1078 (0.6); 7.0353 (3.3); 7.0140 (2.1);
3.7399 (16.0); 3.5934 (6.0); 2.1565 (14.4); -0.0002 (10.0) 3.7399 (16.0); 3.5934 (6.0); 2.1565 (14.4); -0.0002 (10.0)
1-294: 1H-NMR(400.0 MHz, CDC13):  1-294: 1H NMR (400.0 MHz, CDC13):
δ= 8.4547 (5.8); 8.4427 (5.8); 7.2611 (16.6); 7.0277 (0.7); 7.0264 (0.6); 7.0244 (0.6); 7.0226 (0.9); 7.0209 (0.7); 7.0072 (2.5); 7.0058 (2.3); 7.0043 (1.6); 6.9896 (1.3); 6.9836 (1.7); 6.9788 (1.8); 6.9709 (2.1); 6.9618 (1.3); 6.9590 (3.7); 6.9470 (2.0); 6.9197 (1.5); 6.9157 (0.8); 6.9134 (0.6); 6.9003 (0.9); 6.8965 (0.5); 5.2968 (0.9); 3.8532 (16.0); 2.2847 (15.8); 2.2660 (9.9); 1.5865δ = 8.4547 (5.8); 8.4427 (5.8); 7.2611 (16.6); 7.0277 (0.7); 7.0264 (0.6); 7.0244 (0.6); 7.0226 (0.9); 7.0209 (0.7); 7.0072 (2.5); 7.0058 (2.3); 7.0043 (1.6); 6.9896 (1.3); 6.9836 (1.7); 6.9788 (1.8); 6.9709 (2.1); 6.9618 (1.3); 6.9590 (3.7); 6.9470 (2.0); 6.9197 (1.5); 6.9157 (0.8); 6.9134 (0.6); 6.9003 (0.9); 6.8965 (0.5); 5.2968 (0.9); 3.8532 (16.0); 2.2847 (15.8); 2.2660 (9.9); 1.5865
(1.4); -0.0002 (6.2) (1.4); -0.0002 (6.2)
1-295: 1H-NMR(400.0 MHz, CDC13):  1-295: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2907 (11.9); 8.0446 (1.4); 8.0410 (1.4); 8.0250 (1.5); 8.0214 (1.4); 7.3676 (0.8); 7.3637 (0.8); 7.3494 (1.1); 7.3470 (1.2); 7.3457 (1.2); 7.3433 (1.0); 7.3290 (1.1); 7.3251 (1.1); 7.2608 (43.9); 7.1543 (1.0); 7.1515 (1.1); 7.1347 (1.4); 7.1333 (1.4); 7.1166 (0.9); 7.1138 (0.9); 7.0425 (1.7); 7.0403 (1.6); 7.0220 (1.6); 7.0198 (1.4); 4.1319 (0.5); 4.1141 (0.6); 3.8727 (15.4);δ = 8.2907 (11.9); 8.0446 (1.4); 8.0410 (1.4); 8.0250 (1.5); 8.02.14 (1.4); 7.3676 (0.8); 7.3637 (0.8); 7.3494 (1.1); 7.3470 (1.2); 7.3457 (1.2); 7.3433 (1.0); 7.3290 (1.1); 7.3251 (1.1); 7.2608 (43.9); 7.1543 (1.0); 7.1515 (1.1); 7.1347 (1.4); 7.1333 (1.4); 7.1166 (0.9); 7.1138 (0.9); 7.0425 (1.7); 7.0403 (1.6); 7.0220 (1.6); 7.0198 (1.4); 4.1319 (0.5); 4.1141 (0.6); 3.8727 (15.4);
2.2761 (16.0); 2.0458 (2.0); 1.2769 (0.8); 1.2590 (1.8); 1.2412 (1.0); 0.0080 (0.6); -0.0002 (16.8) 2.2761 (16.0); 2.0458 (2.0); 1.2769 (0.8); 1.2590 (1.8); 1.2412 (1.0); 0.0080 (0.6); -0.0002 (16.8)
1-296: 1H-NMR(400.0 MHz, CDC13):  1-296: 1H NMR (400.0 MHz, CDC13):
δ= 8.3124 (11.2); 8.2974 (0.6); 7.2650 (0.6); 7.2642 (0.7); 7.2634 (1.0); 7.2601 (40.2); 7.2561 (0.8); 7.2553 (0.6); 6.8051 (1.8); 6.7992 (0.6); 6.7882 (0.7); 6.7830 (2.5); 6.7824 (2.6); 6.7782 (0.7); 6.7672 (0.7); 6.7612 (2.1); 6.4742 (2.1); 6.4682 (0.7); 6.4630 (2.2); 6.4571 (1.2); 6.4513 (1.9); 6.4461 (0.6); 6.4402 (1.8); 5.2980 (0.9); 3.7840 (1.2); 3.7790 (16.0); 2.1676 (1.1); 2.1609 (15.5); -0.0002 (16.3) 1-315: 1H-NMR(400.0 MHz, CDC13): δ = 8.3124 (11.2); 8.2974 (0.6); 7.2650 (0.6); 7.2642 (0.7); 7.2634 (1.0); 7.2601 (40.2); 7.2561 (0.8); 7.2553 (0.6); 6.8051 (1.8); 6.7992 (0.6); 6.7882 (0.7); 6.7830 (2.5); 6.7824 (2.6); 6.7782 (0.7); 6.7672 (0.7); 6.7612 (2.1); 6.4742 (2.1); 6.4682 (0.7); 6.4630 (2.2); 6.4571 (1.2); 6.4513 (1.9); 6.4461 (0.6); 6.4402 (1.8); 5.2980 (0.9); 3.7840 (1.2); 3.7790 (16.0); 2.1676 (1.1); 2.1609 (15.5); -0.0002 (16.3) 1-315: 1H NMR (400.0 MHz, CDC13):
δ= 8.4863 (5.3); 8.4744 (5.4); 8.3443 (1.4); 7.8122 (0.9); 7.8068 (0.9); 7.7905 (0.9); 7.7843 (0.9); 7.2625 (17.4); 7.0041 (1.6);δ = 8.4863 (5.3); 8.4744 (5.4); 8.3443 (1.4); 7.8122 (0.9); 7.8068 (0.9); 7.7905 (0.9); 7.7843 (0.9); 7.2625 (17.4); 7.0041 (1.6);
6.9922 (3.1); 6.9802 (1.6); 6.9344 (1.6); 6.9127 (1.5); 3.7922 (16.0); 2.1976 (15.6); 1.5971 (1.5); -0.0002 (5.2) 6.9922 (3.1); 6.9802 (1.6); 6.9344 (1.6); 6.9127 (1.5); 3.7922 (16.0); 2.1976 (15.6); 1.5971 (1.5); -0.0002 (5.2)
1-316: 1H-NMR(400.0 MHz, CDC13):  1-316: 1H NMR (400.0 MHz, CDC13):
δ= 8.5032 (5.8); 8.4912 (6.2); 8.4782 (0.9); 8.3516 (1.5); 8.3250 (10.7); 7.2646 (17.9); 7.0150 (1.8); 7.0031 (3.4); 6.9911 (1.7); 5.2994 (1.4); 3.7945 (2.2); 3.7837 (16.0); 3.7362 (0.8); 3.6729 (0.5); 2.2324 (0.6); 2.2149 (15.6); 2.1977 (2.2); 1.2677 (1.6);δ = 8.5032 (5.8); 8.4912 (6.2); 8.4782 (0.9); 8.3516 (1.5); 8.3250 (10.7); 7.2646 (17.9); 7.0150 (1.8); 7.0031 (3.4); 6.9911 (1.7); 5.2994 (1.4); 3.7945 (2.2); 3.7837 (16.0); 3.7362 (0.8); 3.6729 (0.5); 2.2324 (0.6); 2.2149 (15.6); 2.1977 (2.2); 1.2677 (1.6);
1.2405 (9.1); -0.0002 (7.0) 1.2405 (9.1); -0.0002 (7.0)
1-317: 1H-NMR(400.0 MHz, CDC13):  1-317: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2968 (10.8); 8.2444 (1.1); 7.2617 (14.3); 6.9269 (0.6); 6.9041 (1.3); 6.8790 (1.2); 6.8563 (0.6); 6.4364 (0.6); 6.4289 (0.6); 6.4196 (0.6); 6.4121 (0.6); 6.4025 (0.6); 6.3950 (0.6); 6.3857 (0.5); 6.3782 (0.6); 6.2767 (0.7); 6.2730 (0.6); 6.2540 (0.6); 6.2502 (0.6); 5.2983 (2.5); 3.8636 (2.2); 3.7773 (16.0); 3.6565 (2.0); 3.0397 (15.3); 2.0868 (15.6); 2.0502 (2.0); 1.5733 (0.5); 1.2407δ = 8.2968 (10.8); 8.2444 (1.1); 7.2617 (14.3); 6.9269 (0.6); 6.9041 (1.3); 6.8790 (1.2); 6.8563 (0.6); 6.4364 (0.6); 6.4289 (0.6); 6.4196 (0.6); 6.4121 (0.6); 6.4025 (0.6); 6.3950 (0.6); 6.3857 (0.5); 6.3782 (0.6); 6.2767 (0.7); 6.2730 (0.6); 6.2540 (0.6); 6.2502 (0.6); 5.2983 (2.5); 3.8636 (2.2); 3.7773 (16.0); 3.6565 (2.0); 3.0397 (15.3); 2.0868 (15.6); 2.0502 (2.0); 1.5733 (0.5); 1.2407
(0.8); -0.0002 (5.5) (0.8); -0.0002 (5.5)
1-318: 1H-NMR(400.0 MHz, CDC13):  1-318: 1H NMR (400.0 MHz, CDC13):
δ= 8.2735 (11.1); 7.2606 (19.7); 7.0660 (3.8); 7.0604 (1.2); 7.0489 (1.2); 7.0432 (4.1); 6.5452 (3.8); 6.5396 (1.2); 6.5281 (1.1); 6.5225 (3.5); 5.2980 (2.4); 3.8585 (0.8); 3.7729 (16.0); 3.6480 (0.7); 3.0538 (15.8); 2.0715 (15.5); 2.0361 (0.7); 1.5588 (0.9); -δ = 8.2735 (11.1); 7.2606 (19.7); 7.0660 (3.8); 7.0604 (1.2); 7.0489 (1.2); 7.0432 (4.1); 6.5452 (3.8); 6.5396 (1.2); 6.5281 (1.1); 6.5225 (3.5); 5.2980 (2.4); 3.8585 (0.8); 3.7729 (16.0); 3.6480 (0.7); 3.0538 (15.8); 2.0715 (15.5); 2.0361 (0.7); 1.5588 (0.9); -
0.0002 (7.7) 0.0002 (7.7)
1-319: 1H-NMR(400.0 MHz, CDC13):  1-319: 1H-NMR (400.0 MHz, CDC13):
δ= 8.7441 (12.3); 8.5089 (5.8); 8.4970 (5.9); 7.2639 (18.7); 7.0441 (1.7); 7.0321 (3.2); 7.0201 (1.6); 5.2995 (4.3); 3.7976 (16.0);δ = 8.7441 (12.3); 8.5089 (5.8); 8.4970 (5.9); 7.2639 (18.7); 7.0441 (1.7); 7.0321 (3.2); 7.0201 (1.6); 5.2995 (4.3); 3.7976 (16.0);
2.9561 (1.7); 2.8832 (1.4); 2.2196 (15.8); 2.0435 (0.8); 1.2585 (0.6); -0.0002 (6.6) 2.9561 (1.7); 2.8832 (1.4); 2.2196 (15.8); 2.0435 (0.8); 1.2585 (0.6); -0.0002 (6.6)
1-320: 1H-NMR(400.0 MHz, CDC13):  1-320: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3333 (10.2); 8.3293 (1.1); 8.3206 (0.8); 8.3122 (0.8); 8.2919 (4.9); 8.2903 (4.9); 7.2614 (43.4); 5.2989 (1.4); 3.7730 (16.0); 3.5687 (1.4); 2.9557 (1.2); 2.8841 (1.0); 2.8829 (1.0); 2.2629 (0.6); 2.2275 (9.5); 2.2177 (1.0); 2.2037 (16.0); 1.5618 (0.9);δ = 8.3333 (10.2); 8.3293 (1.1); 8.3206 (0.8); 8.3122 (0.8); 8.2919 (4.9); 8.2903 (4.9); 7.2614 (43.4); 5.2989 (1.4); 3.7730 (16.0); 3.5687 (1.4); 2.9557 (1.2); 2.8841 (1.0); 2.8829 (1.0); 2.2629 (0.6); 2.2275 (9.5); 2.2177 (1.0); 2.2037 (16.0); 1.5618 (0.9);
1.2560 (0.8); 0.0080 (0.6); -0.0002 (19.3); -0.0085 (0.6) 1.2560 (0.8); 0.0080 (0.6); -0.0002 (19.3); -0.0085 (0.6)
1-321 : 1H-NMR(400.0 MHz, CDC13):  1-321: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3353 (0.8); 8.3307 (10.6); 8.3233 (2.2); 8.3199 (2.2); 8.2212 (2.2); 8.2145 (2.3); 8.0384 (1.6); 8.0349 (1.6); 8.0317 (1.5); 8.0281 (1.4); 7.2633 (15.0); 5.2990 (1.9); 3.7857 (16.0); 3.7799 (0.8); 3.7746 (0.9); 2.2147 (1.0); 2.2111 (0.6); 2.2013 (15.8);δ = 8.3353 (0.8); 8.3307 (10.6); 8.3233 (2.2); 8.3199 (2.2); 8.2212 (2.2); 8.2145 (2.3); 8.0384 (1.6); 8.0349 (1.6); 8.0317 (1.5); 8.0281 (1.4); 7.2633 (15.0); 5.2990 (1.9); 3.7857 (16.0); 3.7799 (0.8); 3.7746 (0.9); 2.2147 (1.0); 2.2111 (0.6); 2.2013 (15.8);
1.5858 (3.0); 1.2560 (0.5); -0.0002 (6.4) 1.5858 (3.0); 1.2560 (0.5); -0.0002 (6.4)
1-322: lH-NMR(400.0 MHz, CDC13):  1-322: 1 H NMR (400.0 MHz, CDC13):
δ= 8.3625 (1.1); 8.3604 (1.1); 8.3586 (1.1); 8.3564 (1.1); 8.3346 (11.0); 7.8359 (0.8); 7.8297 (0.8); 7.8142 (0.8); 7.8088 (0.8);δ = 8.3625 (1.1); 8.3604 (1.1); 8.3586 (1.1); 8.3564 (1.1); 8.3346 (11.0); 7.8359 (0.8); 7.8297 (0.8); 7.8142 (0.8); 7.8088 (0.8);
7.2626 (13.4); 6.9501 (1.4); 6.9285 (1.3); 5.2986 (3.1); 3.7874 (16.0); 2.1924 (15.8); 1.5760 (1.5); -0.0002 (5.5) 7.2626 (13.4); 6.9501 (1.4); 6.9285 (1.3); 5.2986 (3.1); 3.7874 (16.0); 2.1924 (15.8); 1.5760 (1.5); -0.0002 (5.5)
1-323: 1H-NMR(400.0 MHz, CDC13):  1-323: 1H-NMR (400.0 MHz, CDC13):
δ= 8.5935 (1.3); 8.5841 (1.3); 7.2636 (18.4); 7.0628 (1.1); 7.0509 (2.1); 7.0390 (1.1); 3.7898 (0.9); 3.7763 (16.0); 3.1740 (0.6); 3.1583 (0.9); 3.1404 (0.6); 2.3489 (14.0); 2.3124 (0.8); 1.8239 (0.6); 1.8199 (0.5); 1.8115 (0.9); 1.8084 (0.8); 1.8027 (0.7); 1.7935 (0.9); 1.7807 (0.7); 1.7669 (0.5); 1.7636 (0.5); 1.7110 (0.6); 1.7034 (0.7); 1.6945 (1.2); 1.6855 (1.5); 1.6813 (1.2); 1.6734δ = 8.5935 (1.3); 8.5841 (1.3); 7.2636 (18.4); 7.0628 (1.1); 7.0509 (2.1); 7.0390 (1.1); 3.7898 (0.9); 3.7763 (16.0); 3.1740 (0.6); 3.1583 (0.9); 3.1404 (0.6); 2.3489 (14.0); 2.3124 (0.8); 1.8239 (0.6); 1.8199 (0.5); 1.8115 (0.9); 1.8084 (0.8); 1.8027 (0.7); 1.7935 (0.9); 1.7807 (0.7); 1.7669 (0.5); 1.7636 (0.5); 1.7110 (0.6); 1.7034 (0.7); 1.6945 (1.2); 1.6855 (1.5); 1.6813 (1.2); 1.6734
(1.2) ; 1.6665 (0.8); 1.5191 (0.7); 1.5157 (0.8); 1.5079 (0.8); 1.5046 (0.9); 1.5006 (1.2); 1.4904 (1.9); 1.4839 (2.1); 1.4756 (1.9);(1.2); 1.6665 (0.8); 1.5191 (0.7); 1.5157 (0.8); 1.5079 (0.8); 1.5046 (0.9); 1.5006 (1.2); 1.4904 (1.9); 1.4839 (2.1); 1.4756 (1.9);
1.4706 (1.1); 1.4603 (1.0); 1.4561 (0.8); 1.4493 (0.5); 1.4447 (0.6); -0.0002 (7.2) 1.4706 (1.1); 1.4603 (1.0); 1.4561 (0.8); 1.4493 (0.5); 1.4447 (0.6); -0.0002 (7.2)
1-324: 1H-NMR(400.0 MHz, CDC13):  1-324: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4410 (2.0); 8.4081 (0.8); 7.2626 (23.4); 3.7858 (3.6); 3.7720 (16.0); 3.1606 (0.9); 3.1446 (1.2); 3.1282 (0.8); 2.3526 (13.5); 2.3136 (3.2); 2.2719 (0.5); 2.2531 (0.6); 1.8599 (0.5); 1.8257 (0.7); 1.8137 (1.0); 1.7941 (1.0); 1.7832 (1.0); 1.7638 (0.6); 1.7140 (0.6); 1.7057 (0.8); 1.6973 (1.1); 1.6916 (1.1); 1.6882 (1.2); 1.6752 (1.1); 1.6682 (0.6); 1.5998 (0.9); 1.5249 (0.8); 1.5143 (0.9); 1.5089 (1.2); 1.4990 (1.7); 1.4921 (1.8); 1.4841 (2.0); 1.4712 (1.3); 1.4647 (1.0); 1.4539 (1.0); 1.4380 (0.7); -0.0002 (9.0) 1-325: 1H-NMR(400.0 MHz, CDC13): δ = 8.4410 (2.0); 8.4081 (0.8); 7.2626 (23.4); 3.7858 (3.6); 3.7720 (16.0); 3.1606 (0.9); 3.1446 (1.2); 3.1282 (0.8); 2.3526 (13.5); 2.3136 (3.2); 2.2719 (0.5); 2.2531 (0.6); 1.8599 (0.5); 1.8257 (0.7); 1.8137 (1.0); 1.7941 (1.0); 1.7832 (1.0); 1.7638 (0.6); 1.7140 (0.6); 1.7057 (0.8); 1.6973 (1.1); 1.6916 (1.1); 1.6882 (1.2); 1.6752 (1.1); 1.6682 (0.6); 1.5998 (0.9); 1.5249 (0.8); 1.5143 (0.9); 1.5089 (1.2); 1.4990 (1.7); 1.4921 (1.8); 1.4841 (2.0); 1.4712 (1.3); 1.4647 (1.0); 1.4539 (1.0); 1.4380 (0.7); -0.0002 (9.0) 1-325: 1H NMR (400.0 MHz, CDC13):
δ= 7.2607 (12.2); 6.8908 (0.6); 6.6302 (3.6); 3.7285 (4.5); 2.3547 (16.0); 2.3157 (2.6); 2.1194 (7.5); 1.5869 (0.9); -0.0002 (4.7) 1-326: 1H-NMR(400.0 MHz, CDC13): δ = 7.2607 (12.2); 6.8908 (0.6); 6.6302 (3.6); 3.7285 (4.5); 2.3547 (16.0); 2.3157 (2.6); 2.1194 (7.5); 1.5869 (0.9); -0.0002 (4.7) 1-326: 1H NMR (400.0 MHz, CDC13):
δ= 7.2610 (12.2); 6.8984 (0.8); 6.8910 (0.6); 6.8836 (1.0); 6.8768 (1.0); 6.8619 (1.7); 6.8345 (2.7); 6.8182 (0.9); 6.8146 (0.8);δ = 7.2610 (12.2); 6.8984 (0.8); 6.8910 (0.6); 6.8836 (1.0); 6.8768 (1.0); 6.8619 (1.7); 6.8345 (2.7); 6.8182 (0.9); 6.8146 (0.8);
3.7342 (4.3); 2.3916 (16.0); 2.3036 (2.9); 1.5889 (0.6); -0.0002 (4.6) 3.7342 (4.3); 2.3916 (16.0); 2.3036 (2.9); 1.5889 (0.6); -0.0002 (4.6)
1-327: 1H-NMR(400.0 MHz, CDC13):  1-327: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4634 (2.2); 8.4515 (2.3); 7.2619 (14.0); 7.0638 (0.7); 7.0590 (0.8); 7.0459 (0.9); 7.0436 (1.0); 7.0412 (1.0); 7.0389 (1.0); 7.0257 (0.9); 7.0210 (1.0); 6.9704 (1.4); 6.9585 (2.7); 6.9465 (1.4); 6.8419 (0.7); 6.8373 (0.9); 6.8225 (2.0); 6.8179 (1.8); 6.8024δ = 8.4634 (2.2); 8.4515 (2.3); 7.2619 (14.0); 7.0638 (0.7); 7.0590 (0.8); 7.0459 (0.9); 7.0436 (1.0); 7.0412 (1.0); 7.0389 (1.0); 7.0257 (0.9); 7.0210 (1.0); 6.9704 (1.4); 6.9585 (2.7); 6.9465 (1.4); 6.8419 (0.7); 6.8373 (0.9); 6.8225 (2.0); 6.8179 (1.8); 6.8024
(1.3) ; 6.7995 (1.5); 6.7845 (1.2); 6.7816 (1.4); 6.7624 (1.9); 6.7427 (1.3); 6.7401 (1.1); 3.8419 (14.6); 3.8251 (16.0); 2.2870(1.3); 6.7995 (1.5); 6.7845 (1.2); 6.7816 (1.4); 6.7624 (1.9); 6.7427 (1.3); 6.7401 (1.1); 3.8419 (14.6); 3.8251 (16.0); 2.2870
(14.0); 1.6115 (0.5); -0.0002 (5.7) (14.0); 1.6115 (0.5); -0.0002 (5.7)
1-328: 1H-NMR(400.0 MHz, CDC13):  1-328: 1H NMR (400.0 MHz, CDC13):
δ= 8.4686 (1.4); 7.2623 (39.3); 3.7744 (16.0); 2.6305 (0.6); 2.6241 (0.6); 2.6139 (0.9); 2.6049 (0.8); 2.5876 (0.5); 2.3535 (13.1); 1.8485 (0.9); 1.8387 (1.4); 1.8172 (2.0); 1.7085 (1.7); 1.6993 (1.8); 1.6243 (1.2); 1.5602 (0.9); 1.5378 (0.8); 1.2342 (1.3); 1.2172 (2.0); 1.2072 (3.2); 1.1972 (2.4); 1.1895 (2.2); 1.1743 (2.6); 1.1548 (1.2); 1.1466 (1.2); 0.0080 (0.5); -0.0002 (15.2); -0.0085 (0.5) 1-329: 1H-NMR(400.0 MHz, CDC13): δ = 8.4686 (1.4); 7.2623 (39.3); 3.7744 (16.0); 2.6305 (0.6); 2.6241 (0.6); 2.6139 (0.9); 2.6049 (0.8); 2.5876 (0.5); 2.3535 (13.1); 1.8485 (0.9); 1.8387 (1.4); 1.8172 (2.0); 1.7085 (1.7); 1.6993 (1.8); 1.6243 (1.2); 1.5602 (0.9); 1.5378 (0.8); 1.2342 (1.3); 1.2172 (2.0); 1.2072 (3.2); 1.1972 (2.4); 1.1895 (2.2); 1.1743 (2.6); 1.1548 (1.2); 1.1466 (1.2); 0.0080 (0.5); -0.0002 (15.2); -0.0085 (0.5) 1-329: 1H-NMR (400.0 MHz, CDC13):
δ= 8.5802 (5.9); 8.5682 (6.1); 7.2616 (29.4); 7.0561 (1.9); 7.0441 (3.6); 7.0321 (1.8); 3.7822 (16.0); 2.3336 (15.3); 1.8431 (0.7); 1.8187 (1.0); 1.7020 (0.8); 1.6880 (0.8); 1.6785 (0.7); 1.6336 (1.8); 1.2366 (0.6); 1.2161 (1.1); 1.1953 (1.1); 1.1892 (1.2); 1.1669δ = 8.5802 (5.9); 8.5682 (6.1); 7.2616 (29.4); 7.0561 (1.9); 7.0441 (3.6); 7.0321 (1.8); 3.7822 (16.0); 2.3336 (15.3); 1.8431 (0.7); 1.8187 (1.0); 1.7020 (0.8); 1.6880 (0.8); 1.6785 (0.7); 1.6336 (1.8); 1.2366 (0.6); 1.2161 (1.1); 1.1953 (1.1); 1.1892 (1.2); 1.1669
(1.3); 1.1423 (0.6); -0.0002 (11.7) (1.3); 1.1423 (0.6); -0.0002 (11.7)
1-330: 1H-NMR(400.0 MHz, CDC13):  1-330: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4646 (6.1); 8.4527 (6.2); 8.0342 (4.2); 8.0290 (1.4); 8.0167 (1.3); 8.0115 (4.5); 8.0050 (0.6); 7.2624 (20.6); 7.1795 (0.5); 7.1729 (4.5); 7.1677 (1.4); 7.1555 (1.3); 7.1503 (4.4); 7.1438 (0.6); 7.0117 (1.8); 6.9997 (3.5); 6.9877 (1.8); 3.8769 (16.0);δ = 8.4646 (6.1); 8.4527 (6.2); 8.0342 (4.2); 8.0290 (1.4); 8.0167 (1.3); 8.0115 (4.5); 8.0050 (0.6); 7.2624 (20.6); 7.1795 (0.5); 7.1729 (4.5); 7.1677 (1.4); 7.1555 (1.3); 7.1503 (4.4); 7.1438 (0.6); 7.0117 (1.8); 6.9997 (3.5); 6,987 (1.8); 3.8769 (16.0);
3.4882 (0.7); 2.2986 (15.6); 1.5717 (0.8); -0.0002 (8.0) 3.4882 (0.7); 2.2986 (15.6); 1.5717 (0.8); -0.0002 (8.0)
1-331 : 1H-NMR(400.0 MHz, CDC13):  1-331: 1H NMR (400.0 MHz, CDC13):
δ= 7.2599 (54.6); 7.0706 (0.6); 7.0585 (0.7); 7.0563 (0.7); 7.0510 (0.6); 7.0437 (0.6); 7.0361 (0.7); 6.7962 (2.9); 6.7891 (1.6); 6.7832 (1.2); 6.7807 (1.2); 6.7714 (1.6); 6.7517 (1.3); 3.8317 (16.0); 2.3942 (1.2); 1.5421 (3.5); 0.0080 (0.7); -0.0002 (21.5); - 0.0085 (0.8) 1-332: 1H-NMR(400.0 MHz, CDC13): δ = 7.2599 (54.6); 7.0706 (0.6); 7.0585 (0.7); 7.0563 (0.7); 7.0510 (0.6); 7.0437 (0.6); 7.0361 (0.7); 6.7962 (2.9); 6.7891 (1.6); 6.7832 (1.2); 6.7807 (1.2); 6.7714 (1.6); 6.7517 (1.3); 3.8317 (16.0); 2.3942 (1.2); 1.5421 (3.5); 0.0080 (0.7); -0.0002 (21.5); - 0.0085 (0.8) 1-332: 1H NMR (400.0 MHz, CDC13):
δ= 8.1230 (0.5); 7.2597 (28.9); 6.6172 (2.8); 6.6162 (2.8); 3.7416 (6.0); 2.3406 (16.0); 2.1356 (5.9); 1.5540 (1.2); -0.0002 (11.3) 1-333: 1H-NMR(400.0 MHz, CDC13): δ = 8.1230 (0.5); 7.2597 (28.9); 6.6172 (2.8); 6.6162 (2.8); 3.7416 (6.0); 2.3406 (16.0); 2.1356 (5.9); 1.5540 (1.2); -0.0002 (11.3) 1-333: 1H NMR (400.0 MHz, CDC13):
δ= 8.5012 (1.9); 8.4893 (1.9); 7.2601 (65.0); 7.0472 (1.2); 7.0352 (2.2); 7.0232 (1.1); 6.9411 (0.8); 6.9364 (0.5); 6.9199 (1.0); 6.9148 (0.6); 6.8995 (0.7); 6.8943 (0.9); 6.8742 (0.7); 6.8449 (0.5); 6.6772 (0.5); 5.2565 (0.7); 4.1584 (2.2); 4.1474 (14.6);δ = 8.5012 (1.9); 8.4893 (1.9); 7.2601 (65.0); 7.0472 (1.2); 7.0352 (2.2); 7.0232 (1.1); 6.9411 (0.8); 6.9364 (0.5); 6.9199 (1.0); 6.9148 (0.6); 6.8995 (0.7); 6.8943 (0.9); 6.8742 (0.7); 6.8449 (0.5); 6.6772 (0.5); 5.2565 (0.7); 4.1584 (2.2); 4.1474 (14.6);
3.9099 (4.2); 3.8709 (16.0); 1.5776 (2.6); 0.0080 (0.8); -0.0002 (24.4); -0.0084 (0.9) 3.9099 (4.2); 3.8709 (16.0); 1.5776 (2.6); 0.0080 (0.8); -0.0002 (24.4); -0.0084 (0.9)
1-334: 1H-NMR(400.0 MHz, CDC13):  1-334: 1H NMR (400.0 MHz, CDC13):
δ= 8.4871 (4.4); 8.4751 (4.5); 8.0193 (0.7); 7.2605 (53.1); 7.0475 (1.5); 7.0356 (2.8); 7.0236 (1.4); 6.6787 (1.3); 6.6763 (0.8); 6.6731 (1.5); 6.6707 (0.8); 6.6614 (0.7); 6.6591 (1.4); 6.6535 (1.3); 6.5370 (0.6); 6.5206 (0.7); 6.5149 (1.2); 6.5092 (0.6); 6.4927 (0.6); 4.2188 (15.8); 4.2024 (1.0); 3.9480 (1.0); 3.8362 (16.0); 2.9558 (7.0); 2.8843 (5.8); 2.8833 (5.7); 2.0436 (0.6); 1.5505δ = 8.4871 (4.4); 8.4751 (4.5); 8.0193 (0.7); 7.2605 (53.1); 7.0475 (1.5); 7.0356 (2.8); 7.0236 (1.4); 6.6787 (1.3); 6.6763 (0.8); 6.6731 (1.5); 6.6707 (0.8); 6.6614 (0.7); 6.6591 (1.4); 6.6535 (1.3); 6.5370 (0.6); 6.5206 (0.7); 6.5149 (1.2); 6.5092 (0.6); 6.4927 (0.6); 4.2188 (15.8); 4.2024 (1.0); 3.9480 (1.0); 3.8362 (16.0); 2.9558 (7.0); 2.8843 (5.8); 2.8833 (5.7); 2.0436 (0.6); 1.5505
(4.0); 1.2586 (0.6); 0.0080 (0.7); -0.0002 (22.0); -0.0085 (0.7) (4.0); 1.2586 (0.6); 0.0080 (0.7); -0.0002 (22.0); -0.0085 (0.7)
1-336: 1H-NMR(400.0 MHz, CDC13):  1-336: 1H NMR (400.0 MHz, CDC13):
δ= 8.4394 (4.2); 8.3246 (10.2); 8.2152 (1.5); 8.2078 (1.6); 7.2604 (61.0); 7.2432 (1.2); 7.2411 (1.3); 7.2357 (1.1); 7.2337 (1.2); 7.2211 (1.0); 7.2138 (0.9); 7.0477 (0.9); 7.0464 (0.9); 7.0376 (0.9); 7.0363 (0.9); 7.0257 (0.7); 7.0244 (0.8); 7.0155 (0.8); 7.0142δ = 8.4394 (4.2); 8.3246 (10.2); 8.2152 (1.5); 8.2078 (1.6); 7.2604 (61.0); 7.2432 (1.2); 7.2411 (1.3); 7.2357 (1.1); 7.2337 (1.2); 7.2211 (1.0); 7.2138 (0.9); 7.0477 (0.9); 7.0464 (0.9); 7.0376 (0.9); 7.0363 (0.9); 7.0257 (0.7); 7.0244 (0.8); 7.0155 (0.8); 7.0142
(0.7); 4.2113 (15.7); 4.1963 (7.5); 3.9515 (7.3); 3.7949 (16.0); 1.9499 (0.6); 0.0079 (0.7); -0.0002 (23.7); -0.0085 (1.1) (0.7); 4.2113 (15.7); 4.1963 (7.5); 3.9515 (7.3); 3.7949 (16.0); 1.9499 (0.6); 0.0079 (0.7); -0.0002 (23.7); -0.0085 (1.1)
1-337: lH-NMR(400.6 MHz, d6-DMSO):  1-337: 1 H-NMR (400.6 MHz, d6-DMSO):
δ= 8.6660 (16.0); 7.2686 (1.7); 7.2649 (0.7); 7.2503 (4.2); 7.2366 (1.3); 7.2318 (4.2); 7.1884 (1.2); 7.1868 (2.8); 7.1850 (3.4); 7.1836 (4.2); 7.1821 (4.8); 7.1758 (1.0); 7.1701 (0.8); 7.1658 (3.5); 7.1642 (4.4); 7.1626 (4.0); 7.1611 (2.9); 7.1475 (2.9); 7.1451 (2.2); 7.1440 (2.2); 7.1427 (2.3); 7.1376 (0.7); 7.1341 (2.5); 7.1307 (1.4); 7.1283 (1.6); 7.1248 (4.9); 7.1175 (1.6); 7.1116 (4.0); 7.1041 (0.7); 7.0878 (1.0); 7.0805 (4.4); 7.0745 (1.2); 7.0659 (0.8); 7.0637 (1.0); 7.0584 (6.0); 7.0526 (1.3); 7.0417 (1.0); 7.0359δ = 8.6660 (16.0); 7.2686 (1.7); 7.2649 (0.7); 7.2503 (4.2); 7.2366 (1.3); 7.2318 (4.2); 7.1884 (1.2); 7.1868 (2.8); 7.1850 (3.4); 7.1836 (4.2); 7.1821 (4.8); 7.1758 (1.0); 7.1701 (0.8); 7.1658 (3.5); 7.1642 (4.4); 7.1626 (4.0); 7.1611 (2.9); 7.1475 (2.9); 7.1451 (2.2); 7.1440 (2.2); 7.1427 (2.3); 7.1376 (0.7); 7.1341 (2.5); 7.1307 (1.4); 7.1283 (1.6); 7.1248 (4.9); 7.1175 (1.6); 7.1116 (4.0); 7.1041 (0.7); 7.0878 (1.0); 7.0805 (4.4); 7.0745 (1.2); 7.0659 (0.8); 7.0637 (1.0); 7.0584 (6.0); 7.0526 (1.3); 7.0417 (1.0); 7.0359
(2.5) ; 4.3035 (1.4); 4.2858 (4.9); 4.2680 (4.9); 4.2503 (1.5); 3.7448 (1.6); 3.7385 (0.8); 3.7328 (0.7); 3.7287 (0.7); 3.7239 (1.0); 3.7167 (0.9); 3.7113 (0.8); 3.7014 (1.5); 3.6980 (1.1); 3.6921 (1.4); 3.6853 (1.1); 3.6809 (1.0); 3.6733 (1.2); 3.6642 (1.6); 3.6345(2.5); 4.3035 (1.4); 4.2858 (4.9); 4.2680 (4.9); 4.2503 (1.5); 3.7448 (1.6); 3.7385 (0.8); 3.7328 (0.7); 3.7287 (0.7); 3.7239 (1.0); 3.7167 (0.9); 3.7113 (0.8); 3.7014 (1.5); 3.6980 (1.1); 3.6921 (1.4); 3.6853 (1.1); 3.6809 (1.0); 3.6733 (1.2); 3.6642 (1.6); 3.6345
(1.6) ; 3.6198 (1.7); 3.5644 (1.2); 2.6748 (0.7); 2.6702 (1.1); 2.6656 (0.8); 2.5240 (2.7); 2.5193 (3.8); 2.5105 (57.8); 2.5060 (126.3); 2.5014 (176.4); 2.4968 (121.0); 2.4922 (54.1); 2.3331 (0.8); 2.3284 (1.1); 2.3238 (0.8); 2.2998 (18.7); 1.2014 (6.3);(1.6); 3.6198 (1.7); 3.5644 (1.2); 2.6748 (0.7); 2.6702 (1.1); 2.6656 (0.8); 2.5240 (2.7); 2.5193 (3.8); 2.5105 (57.8); 2.5060 (126.3); 2.5014 (176.4); 2.4968 (121.0); 2.4922 (54.1); 2.3331 (0.8); 2.3284 (1.1); 2.3238 (0.8); 2.2998 (18.7); 1.2014 (6.3);
1.1836 (14.2); 1.1659 (6.1); 0.0081 (1.8); -0.0002 (71.3); -0.0085 (2.1) 1.1836 (14.2); 1.1659 (6.1); 0.0081 (1.8); -0.0002 (71.3); -0.0085 (2.1)
1-338: 1H-NMR(400.0 MHz, CDC13):  1-338: 1H NMR (400.0 MHz, CDC13):
δ= 8.3394 (9.4); 8.3241 (0.9); 7.5186 (0.7); 7.2597 (125.9); 7.1194 (1.0); 6.9956 (0.8); 6.9422 (1.0); 6.9378 (0.8); 6.9335 (0.5); 6.9219 (0.9); 6.9167 (1.0); 6.8963 (0.6); 6.8387 (0.6); 6.8331 (0.5); 4.1522 (0.6); 4.1448 (2.1); 4.1404 (14.9); 3.9479 (0.6);δ = 8.3394 (9.4); 8.3241 (0.9); 7.5186 (0.7); 7.2597 (125.9); 7.1194 (1.0); 6.9956 (0.8); 6.9422 (1.0); 6.9378 (0.8); 6.9335 (0.5); 6.9219 (0.9); 6.9167 (1.0); 6.8963 (0.6); 6.8387 (0.6); 6.8331 (0.5); 4.1522 (0.6); 4.1448 (2.1); 4.1404 (14.9); 3.9479 (0.6);
3.9071 (3.9); 3.8715 (16.0); 3.8613 (1.6); 3.8505 (1.8); 1.5831 (5.4); 0.0080 (1.6); -0.0002 (46.4); -0.0084 (1.7) 3.9071 (3.9); 3.8715 (16.0); 3.8613 (1.6); 3.8505 (1.8); 1.5831 (5.4); 0.0080 (1.6); -0.0002 (46.4); -0.0084 (1.7)
1-339: 1H-NMR(400.0 MHz, CDC13):  1-339: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4719 (4.4); 8.4600 (4.5); 7.2603 (15.2); 7.1318 (2.7); 7.1298 (3.0); 7.1194 (9.6); 7.0861 (0.6); 7.0786 (0.5); 7.0751 (0.6);δ = 8.4719 (4.4); 8.4600 (4.5); 7.2603 (15.2); 7.1318 (2.7); 7.1298 (3.0); 7.1194 (9.6); 7.0861 (0.6); 7.0786 (0.5); 7.0751 (0.6);
7.0647 (0.6); 7.0054 (1.5); 6.9935 (2.8); 6.9815 (1.4); 4.1372 (14.8); 3.9480 (5.9); 3.8499 (16.0); -0.0002 (5.8) 7.0647 (0.6); 7.0054 (1.5); 6.9935 (2.8); 6.9815 (1.4); 4.1372 (14.8); 3.9480 (5.9); 3.8499 (16.0); -0.0002 (5.8)
1-340: 1H-NMR(400.0 MHz, CDC13):  1-340: 1H NMR (400.0 MHz, CDC13):
δ= 8.2687 (8.7); 7.2596 (33.2); 7.1276 (1.3); 7.1225 (1.3); 7.1176 (0.6); 7.1101 (2.8); 7.1086 (2.5); 7.0955 (3.7); 7.0829 (1.0);δ = 8.2687 (8.7); 7.2596 (33.2); 7.1276 (1.3); 7.1225 (1.3); 7.1176 (0.6); 7.1101 (2.8); 7.1086 (2.5); 7.0955 (3.7); 7.0829 (1.0);
7.0790 (1.3); 7.0734 (1.3); 4.1356 (14.9); 3.9525 (5.5); 3.8637 (16.0); -0.0002 (12.5); -0.0085 (0.5) 7.0790 (1.3); 7.0734 (1.3); 4.1356 (14.9); 3.9525 (5.5); 3.8637 (16.0); -0.0002 (12.5); -0.0085 (0.5)
1-341 : 1H-NMR(400.0 MHz, CDC13):  1-341: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3220 (5.6); 7.2596 (56.2); 6.6653 (0.8); 6.6599 (1.0); 6.6459 (0.9); 6.6404 (0.8); 6.5354 (0.7); 4.2123 (9.0); 3.8402 (9.1);δ = 8.3220 (5.6); 7.2596 (56.2); 6.6653 (0.8); 6.6599 (1.0); 6.6459 (0.9); 6.6404 (0.8); 6.5354 (0.7); 4.2123 (9.0); 3.8402 (9.1);
1.5372 (16.0); 0.0079 (0.8); -0.0002 (20.7); -0.0084 (0.8) 1.5372 (16.0); 0.0079 (0.8); -0.0002 (20.7); -0.0084 (0.8)
1-342: 1H-NMR(400.0 MHz, CDC13):  1-342: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3011 (9.0); 7.4565 (2.9); 7.4516 (1.2); 7.4397 (1.1); 7.4346 (3.7); 7.4300 (0.7); 7.2605 (39.4); 7.1838 (0.6); 7.1791 (3.5); 7.1741 (1.3); 7.1622 (1.1); 7.1572 (3.2); 7.1524 (0.6); 4.2181 (15.2); 3.8019 (16.0); 2.0052 (0.9); 1.7079 (0.6); -0.0002 (15.1); -δ = 8.3011 (9.0); 7.4565 (2.9); 7.4516 (1.2); 7.4397 (1.1); 7.4346 (3.7); 7.4300 (0.7); 7.2605 (39.4); 7.1838 (0.6); 7.1791 (3.5); 7.1741 (1.3); 7.1622 (1.1); 7.1572 (3.2); 7.1524 (0.6); 4.2181 (15.2); 3.8019 (16.0); 2.0052 (0.9); 1.7079 (0.6); -0.0002 (15.1); -
0.0085 (0.7) 0.0085 (0.7)
1-343: 1H-NMR(400.0 MHz, CDC13):  1-343: 1H NMR (400.0 MHz, CDC13):
δ= 8.4561 (2.6); 8.4441 (2.6); 7.4333 (3.0); 7.4284 (1.1); 7.4165 (1.2); 7.4115 (3.6); 7.4068 (0.6); 7.2601 (69.6); 7.1955 (0.6); 7.1908 (3.6); 7.1859 (1.2); 7.1739 (1.1); 7.1690 (3.0); 7.1642 (0.5); 7.0430 (1.2); 7.0310 (2.4); 7.0191 (1.2); 4.2243 (15.0);δ = 8.4561 (2.6); 8.4441 (2.6); 7.4333 (3.0); 7.4284 (1.1); 7.4165 (1.2); 7.4115 (3.6); 7.4068 (0.6); 7.2601 (69.6); 7.1955 (0.6); 7.1908 (3.6); 7.1859 (1.2); 7.1739 (1.1); 7.1690 (3.0); 7.1642 (0.5); 7.0430 (1.2); 7.0310 (2.4); 7.0191 (1.2); 4.2243 (15.0);
3.8015 (16.0); 1.6145 (1.7); 0.0080 (0.8); -0.0002 (26.9); -0.0085 (1.0) 3.8015 (16.0); 1.6145 (1.7); 0.0080 (0.8); -0.0002 (26.9); -0.0085 (1.0)
1-344: 1H-NMR(400.0 MHz, CDC13):  1-344: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2676 (9.1); 7.4010 (1.4); 7.3654 (0.8); 7.3627 (0.8); 7.3448 (1.8); 7.3110 (1.1); 7.2914 (0.7); 7.2612 (13.2); 4.1998 (15.5);δ = 8.2676 (9.1); 7.4010 (1.4); 7.3654 (0.8); 7.3627 (0.8); 7.3448 (1.8); 7.3110 (1.1); 7.2914 (0.7); 7.2612 (13.2); 4.1998 (15.5);
3.8221 (16.0); -0.0002 (5.0) 3.8221 (16.0); -0.0002 (5.0)
1-345: 1H-NMR(400.0 MHz, CDC13):  1-345: 1H NMR (400.0 MHz, CDC13):
δ= 8.4419 (2.8); 8.4299 (2.9); 7.4115 (1.4); 7.3730 (0.7); 7.3536 (1.1); 7.3500 (1.0); 7.3277 (1.1); 7.2981 (1.1); 7.2788 (1.2);δ = 8.4419 (2.8); 8.4299 (2.9); 7.4115 (1.4); 7.3730 (0.7); 7.3536 (1.1); 7.3500 (1.0); 7.3277 (1.1); 7.2981 (1.1); 7.2788 (1.2);
7.2606 (25.8); 7.0098 (1.2); 6.9978 (2.4); 6.9859 (1.2); 4.2051 (15.2); 3.8135 (16.0); 1.6276 (0.6); -0.0002 (9.9) 7.2606 (25.8); 7.0098 (1.2); 6.9978 (2.4); 6.9859 (1.2); 4.2051 (15.2); 3.8135 (16.0); 1.6276 (0.6); -0.0002 (9.9)
1-346: 1H-NMR(400.0 MHz, CDC13):  1-346: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3779 (0.6); 8.3673 (0.7); 8.3066 (8.2); 7.5419 (0.5); 7.5374 (0.6); 7.5215 (0.9); 7.5190 (0.9); 7.5030 (0.7); 7.4985 (0.6); 7.2611 (29.7); 7.0592 (1.1); 7.0527 (0.9); 7.0387 (1.6); 7.0218 (0.7); 4.2195 (15.6); 3.7772 (16.0); 2.9274 (0.5); -0.0002 (11.0); -δ = 8.3779 (0.6); 8.3673 (0.7); 8.3066 (8.2); 7.5419 (0.5); 7.5374 (0.6); 7.5215 (0.9); 7.5190 (0.9); 7.5030 (0.7); 7.4985 (0.6); 7.2611 (29.7); 7.0592 (1.1); 7.0527 (0.9); 7.0387 (1.6); 7.0218 (0.7); 4.2195 (15.6); 3.7772 (16.0); 2.9274 (0.5); -0.0002 (11.0); -
0.0085 (0.5) 0.0085 (0.5)
1-347: 1H-NMR(400.0 MHz, CDC13):  1-347: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4765 (2.4); 8.4645 (2.4); 8.3428 (0.6); 8.3327 (0.6); 7.5038 (0.6); 7.4993 (0.5); 7.4836 (0.9); 7.4806 (0.8); 7.4649 (0.6); 7.4604 (0.6); 7.2614 (29.3); 7.0455 (0.9); 7.0362 (1.3); 7.0243 (2.9); 7.0123 (1.3); 6.9972 (0.8); 6.9908 (0.6); 4.2257 (15.5);δ = 8.4765 (2.4); 8.4645 (2.4); 8.3428 (0.6); 8.3327 (0.6); 7.5038 (0.6); 7.4993 (0.5); 7.4836 (0.9); 7.4806 (0.8); 7.4649 (0.6); 7.4604 (0.6); 7.2614 (29.3); 7.0455 (0.9); 7.0362 (1.3); 7.0243 (2.9); 7.0123 (1.3); 6.9972 (0.8); 6.9908 (0.6); 4.2257 (15.5);
3.7664 (16.0); 2.4324 (0.5); -0.0002 (10.9) 3.7664 (16.0); 2.4324 (0.5); -0.0002 (10.9)
1-348: 1H-NMR(400.0 MHz, CDC13):  1-348: 1H NMR (400.0 MHz, CDC13):
δ= 8.2802 (8.1); 7.3624 (0.5); 7.3422 (2.7); 7.3259 (1.0); 7.3247 (1.0); 7.2942 (0.8); 7.2743 (0.8); 7.2601 (29.2); 4.1601 (0.6);δ = 8.2802 (8.1); 7.3624 (0.5); 7.3422 (2.7); 7.3259 (1.0); 7.3247 (1.0); 7.2942 (0.8); 7.2743 (0.8); 7.2601 (29.2); 4.1601 (0.6);
4.1482 (14.6); 4.0159 (4.6); 3.8609 (16.0); 1.6491 (0.7); -0.0002 (11.2) 4.1482 (14.6); 4.0159 (4.6); 3.8609 (16.0); 1.6491 (0.7); -0.0002 (11.2)
1-349: 1H-NMR(400.0 MHz, CDC13):  1-349: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4668 (2.6); 8.4549 (2.7); 7.3569 (2.0); 7.3370 (1.1); 7.3319 (1.2); 7.2834 (0.9); 7.2603 (38.9); 7.0121 (1.2); 7.0001 (2.4); 6.9881 (1.2); 6.6952 (0.6); 5.3652 (0.9); 4.1661 (2.5); 4.1532 (14.4); 4.0104 (4.7); 3.8493 (16.0); 1.5933 (0.8); -0.0002 (14.4) 1-350: 1H-NMR(400.0 MHz, CDC13): δ = 8.4668 (2.6); 8.4549 (2.7); 7.3569 (2.0); 7.3370 (1.1); 7.3319 (1.2); 7.2834 (0.9); 7.2603 (38.9); 7.0121 (1.2); 7,0001 (2.4); 6.9881 (1.2); 6.6952 (0.6); 5.3652 (0.9); 4.1661 (2.5); 4.1532 (14.4); 4.0104 (4.7); 3.8493 (16.0); 1.5933 (0.8); -0.0002 (14.4) 1-350: 1H NMR (400.0 MHz, CDC13):
δ= 8.3301 (8.0); 7.2606 (23.5); 7.0566 (0.6); 7.0401 (0.6); 6.6760 (0.8); 6.6550 (2.5); 6.6339 (1.2); 4.1402 (14.7); 3.9408 (3.7);δ = 8.3301 (8.0); 7.2606 (23.5); 7.0566 (0.6); 7.0401 (0.6); 6.6760 (0.8); 6.6550 (2.5); 6.6339 (1.2); 4.1402 (14.7); 3.9408 (3.7);
3.8559 (16.0); 1.5697 (1.2); -0.0002 (9.0) 3.8559 (16.0); 1.5697 (1.2); -0.0002 (9.0)
1-351 : 1H-NMR(400.0 MHz, CDC13):  1-351: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4966 (2.2); 8.4847 (2.3); 7.2619 (14.4); 7.0725 (0.7); 7.0557 (0.7); 7.0385 (1.3); 7.0266 (2.2); 7.0146 (1.1); 6.6603 (0.9);δ = 8.4966 (2.2); 8.4847 (2.3); 7.2619 (14.4); 7.0725 (0.7); 7.0557 (0.7); 7.0385 (1.3); 7.0266 (2.2); 7.0146 (1.1); 6.6603 (0.9);
6.6555 (0.6); 6.6357 (2.0); 6.6182 (0.5); 6.6147 (1.4); 4.1474 (14.4); 3.9437 (4.0); 3.8498 (16.0); -0.0002 (5.6) 6.6555 (0.6); 6.6357 (2.0); 6.6182 (0.5); 6.6147 (1.4); 4.1474 (14.4); 3.9437 (4.0); 3.8498 (16.0); -0.0002 (5.6)
1-352: 1H-NMR(400.0 MHz, CDC13):  1-352: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2554 (8.0); 7.2649 (0.6); 7.2599 (34.1); 7.2488 (0.5); 7.1573 (3.9); 7.1561 (4.0); 7.1471 (4.8); 7.1453 (5.1); 7.1261 (0.7); 7.1158 (0.9); 7.1079 (0.7); 7.1058 (1.0); 7.0947 (0.9); 4.1779 (15.6); 3.8245 (16.0); 1.6162 (1.6); -0.0002 (13.1); -0.0084 (0.6) 1-353: 1H-NMR(400.0 MHz, CDC13): δ = 8.2554 (8.0); 7.2649 (0.6); 7.2599 (34.1); 7.2488 (0.5); 7.1573 (3.9); 7.1561 (4.0); 7.1471 (4.8); 7.1453 (5.1); 7.1261 (0.7); 7.1158 (0.9); 7.1079 (0.7); 7.1058 (1.0); 7.0947 (0.9); 4.1779 (15.6); 3.8245 (16.0); 1.6162 (1.6); -0.0002 (13.1); -0.0084 (0.6) 1-353: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3101 (9.4); 7.2601 (26.7); 7.0858 (1.1); 7.0803 (0.5); 7.0722 (1.2); 7.0637 (1.4); 7.0558 (0.6); 7.0502 (1.3); 6.8466 (1.6); 6.8412 (0.5); 6.8300 (0.6); 6.8248 (2.9); 6.8194 (0.6); 6.8029 (1.3); 4.1483 (0.6); 4.1320 (14.9); 3.9186 (4.0); 3.8671 (16.0); -δ = 8.3101 (9.4); 7.2601 (26.7); 7.0858 (1.1); 7.0803 (0.5); 7.0722 (1.2); 7.0637 (1.4); 7.0558 (0.6); 7.0502 (1.3); 6.8466 (1.6); 6.8412 (0.5); 6.8300 (0.6); 6.8248 (2.9); 6.8194 (0.6); 6.8029 (1.3); 4.1483 (0.6); 4.1320 (14.9); 3.9186 (4.0); 3.8671 (16.0); -
0.0002 (10.2) 0.0002 (10.2)
1-354: lH-NMR(400.0 MHz, CDC13):  1-354: 1H NMR (400.0 MHz, CDC13):
δ= 8.4805 (4.9); 8.4686 (5.0); 7.2604 (18.8); 7.0991 (1.3); 7.0939 (0.6); 7.0855 (1.5); 7.0774 (1.6); 7.0638 (1.5); 7.0247 (1.5); 7.0128 (2.8); 7.0008 (1.4); 6.8287 (1.8); 6.8234 (0.6); 6.8068 (3.3); 6.8015 (0.7); 6.7900 (0.6); 6.7849 (1.5); 4.1373 (15.3);δ = 8.4805 (4.9); 8.4686 (5.0); 7.2604 (18.8); 7.0991 (1.3); 7.0939 (0.6); 7.0855 (1.5); 7.0774 (1.6); 7.0638 (1.5); 7.0247 (1.5); 7.0128 (2.8); 7,0008 (1.4); 6.8287 (1.8); 6.8234 (0.6); 6.8068 (3.3); 6.8015 (0.7); 6.7900 (0.6); 6.7849 (1.5); 4.1373 (15.3);
3.9203 (5.4); 3.8636 (16.0); -0.0002 (10.6) 3.9203 (5.4); 3.8636 (16.0); -0.0002 (10.6)
1-355: 1H-NMR(400.0 MHz, CDC13):  1-355: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2774 (9.0); 7.2600 (43.5); 7.1343 (0.6); 7.1299 (0.8); 7.1252 (0.6); 7.1205 (0.8); 7.1151 (1.1); 7.1107 (1.4); 7.1043 (0.6); 7.1027 (0.7); 7.0947 (0.5); 7.0924 (0.9); 7.0895 (0.8); 6.9621 (0.5); 6.9594 (1.0); 6.9535 (0.8); 6.9517 (0.7); 6.9408 (0.6); 6.9366 (1.7); 6.9340 (1.6); 6.9320 (1.1); 6.9157 (1.2); 6.9127 (0.6); 4.1752 (16.0); 3.8569 (16.0); 1.5484 (3.0); 0.0080 (0.5); -0.0002δ = 8.2774 (9.0); 7.2600 (43.5); 7.1343 (0.6); 7.1299 (0.8); 7.1252 (0.6); 7.1205 (0.8); 7.1151 (1.1); 7.1107 (1.4); 7.1043 (0.6); 7.1027 (0.7); 7.0947 (0.5); 7.0924 (0.9); 7.0895 (0.8); 6.9621 (0.5); 6.9594 (1.0); 6.9535 (0.8); 6.9517 (0.7); 6.9408 (0.6); 6.9366 (1.7); 6.9340 (1.6); 6.9320 (1.1); 6.9157 (1.2); 6.9127 (0.6); 4.1752 (16.0); 3.8569 (16.0); 1.5484 (3.0); 0.0080 (0.5); -0.0002
(17.0); -0.0085 (0.6) (17.0); -0.0085 (0.6)
1-356: lH-NMR(400.0 MHz, CDC13):  1-356: 1H NMR (400.0 MHz, CDC13):
δ= 8.4660 (2.4); 8.4540 (2.5); 7.2600 (50.1); 7.1466 (0.6); 7.1320 (0.8); 7.1275 (1.3); 7.1086 (1.0); 7.1037 (0.7); 7.1005 (0.6); 7.0893 (0.6); 7.0826 (0.6); 7.0253 (1.2); 7.0133 (2.3); 7.0013 (1.2); 6.9459 (1.0); 6.9421 (1.0); 6.9225 (2.5); 6.9030 (1.3); 4.1807δ = 8.4660 (2.4); 8.4540 (2.5); 7.2600 (50.1); 7.1466 (0.6); 7.1320 (0.8); 7.1275 (1.3); 7.1086 (1.0); 7.1037 (0.7); 7.1005 (0.6); 7.0893 (0.6); 7.0826 (0.6); 7.0253 (1.2); 7.0133 (2.3); 7.0013 (1.2); 6.9459 (1.0); 6.9421 (1.0); 6.9225 (2.5); 6.9030 (1.3); 4.1807
(15.2); 3.8470 (16.0); 1.7916 (0.5); 0.0078 (0.6); -0.0002 (17.6); -0.0083 (0.8) (15.2); 3.8470 (16.0); 1.7916 (0.5); 0.0078 (0.6); -0.0002 (17.6); -0.0083 (0.8)
1-357: 1H-NMR(400.0 MHz, CDC13):  1-357: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2987 (8.4); 7.2600 (55.7); 7.2059 (1.6); 7.2005 (0.7); 7.1930 (1.7); 7.1890 (0.8); 7.1875 (0.8); 7.1835 (2.0); 7.1762 (0.8); 7.1707 (1.9); 6.8844 (1.9); 6.8789 (0.6); 6.8675 (0.7); 6.8630 (2.8); 6.8576 (0.7); 6.8463 (0.6); 6.8408 (1.6); 4.1623 (15.5);δ = 8.2987 (8.4); 7.2600 (55.7); 7.2059 (1.6); 7.2005 (0.7); 7.1930 (1.7); 7.1890 (0.8); 7.1875 (0.8); 7.1835 (2.0); 7.1762 (0.8); 7.1707 (1.9); 6.8844 (1.9); 6.8789 (0.6); 6.8675 (0.7); 6.8630 (2.8); 6.8576 (0.7); 6.8463 (0.6); 6.8408 (1.6); 4.1623 (15.5);
3.8633 (16.0); 1.5858 (2.5); 0.0080 (0.6); -0.0002 (19.7); -0.0084 (0.7) 3.8633 (16.0); 1.5858 (2.5); 0.0080 (0.6); -0.0002 (19.7); -0.0084 (0.7)
1-358: 1H-NMR(400.0 MHz, CDC13):  1-358: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3259 (8.9); 7.2599 (67.2); 7.0390 (0.6); 7.0333 (0.6); 7.0207 (0.5); 7.0150 (0.6); 7.0125 (0.6); 7.0069 (1.0); 6.9954 (0.6); 6.9884 (0.7); 6.9853 (0.9); 6.9657 (0.8); 6.9604 (0.8); 6.9408 (1.1); 6.9375 (0.6); 6.9350 (0.6); 6.9319 (0.5); 6.9291 (0.7); 6.9270δ = 8.3259 (8.9); 7.2599 (67.2); 7.0390 (0.6); 7.0333 (0.6); 7.0207 (0.5); 7.0150 (0.6); 7.0125 (0.6); 7.0069 (1.0); 6.9954 (0.6); 6.9884 (0.7); 6.9853 (0.9); 6.9657 (0.8); 6.9604 (0.8); 6.9408 (1.1); 6.9375 (0.6); 6.9350 (0.6); 6.9319 (0.5); 6.9291 (0.7); 6.9270
(0.7); 6.9238 (0.6); 6.9214 (0.5); 4.1823 (15.5); 3.8625 (16.0); 1.6157 (0.7); 0.0079 (0.8); -0.0002 (23.8); -0.0085 (0.8) (0.7); 6.9238 (0.6); 6.9214 (0.5); 4.1823 (15.5); 3.8625 (16.0); 1.6157 (0.7); 0.0079 (0.8); -0.0002 (23.8); -0.0085 (0.8)
1-359: 1H-NMR(400.0 MHz, CDC13):  1-359: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4693 (3.4); 8.4573 (3.4); 7.2603 (36.6); 7.1349 (0.9); 7.1317 (1.5); 7.1299 (1.5); 7.1259 (0.9); 7.0836 (0.7); 7.0821 (0.7); 7.0725 (0.8); 7.0674 (3.0); 7.0652 (4.2); 7.0618 (2.1); 7.0548 (1.8); 7.0500 (1.6); 7.0479 (0.8); 7.0438 (0.6); 7.0213 (1.4); 7.0094δ = 8.4693 (3.4); 8.4573 (3.4); 7.2603 (36.6); 7.1349 (0.9); 7.1317 (1.5); 7.1299 (1.5); 7.1259 (0.9); 7.0836 (0.7); 7.0821 (0.7); 7.0725 (0.8); 7.0674 (3.0); 7.0652 (4.2); 7.0618 (2.1); 7.0548 (1.8); 7.0500 (1.6); 7.0479 (0.8); 7.0438 (0.6); 7.0213 (1.4); 7.0094
(2.6); 6.9974 (1.4); 4.2010 (15.5); 3.8325 (16.0); 1.5495 (2.2); -0.0002 (14.0); -0.0085 (0.5) (2.6); 6.9974 (1.4); 4.2010 (15.5); 3.8325 (16.0); 1.5495 (2.2); -0.0002 (14.0); -0.0085 (0.5)
1-360: 1H-NMR(400.0 MHz, CDC13):  1-360: 1H NMR (400.0 MHz, CDC13):
δ= 8.2925 (9.8); 7.2601 (33.7); 7.1173 (0.8); 7.1162 (0.8); 7.1114 (1.8); 7.1089 (1.0); 7.1069 (1.0); 7.0943 (0.9); 7.0815 (0.5); 7.0770 (2.5); 7.0752 (2.0); 7.0709 (2.5); 7.0665 (1.8); 7.0622 (1.7); 7.0577 (2.0); 7.0526 (1.0); 7.0398 (0.6); 4.1958 (15.7);δ = 8.2925 (9.8); 7.2601 (33.7); 7.1173 (0.8); 7.1162 (0.8); 7.1114 (1.8); 7.1089 (1.0); 7.1069 (1.0); 7.0943 (0.9); 7.0815 (0.5); 7.0770 (2.5); 7.0752 (2.0); 7.0709 (2.5); 7.0665 (1.8); 7.0622 (1.7); 7.0577 (2.0); 7.0526 (1.0); 7.0398 (0.6); 4.1958 (15.7);
3.8425 (16.0); 2.0046 (0.6); 1.5463 (1.1); -0.0002 (12.6) 3.8425 (16.0); 2.0046 (0.6); 1.5463 (1.1); -0.0002 (12.6)
1-361 : 1H-NMR(400.0 MHz, CDC13):  1-361: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4643 (2.1); 8.4524 (2.1); 7.2600 (33.4); 7.1127 (2.3); 7.1082 (0.8); 7.0968 (0.9); 7.0922 (3.0); 7.0167 (1.1); 7.0047 (2.2);δ = 8.4643 (2.1); 8.4524 (2.1); 7.2600 (33.4); 7.1127 (2.3); 7.1082 (0.8); 7.0968 (0.9); 7.0922 (3.0); 7.0167 (1.1); 7.0047 (2.2);
6.9928 (1.1); 6.9475 (2.2); 6.9277 (1.8); 4.1607 (14.8); 3.8404 (16.0); 2.2406 (8.0); -0.0002 (12.3) 6.9928 (1.1); 6.9475 (2.2); 6.9277 (1.8); 4.1607 (14.8); 3.8404 (16.0); 2.2406 (8.0); -0.0002 (12.3)
1-362: 1H-NMR(400.0 MHz, CDC13):  1-362: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2598 (9.2); 7.2599 (28.5); 7.0904 (2.2); 7.0859 (0.8); 7.0746 (0.9); 7.0699 (3.0); 6.9563 (2.3); 6.9365 (1.7); 4.1578 (15.7);δ = 8.2598 (9.2); 7.2599 (28.5); 7.0904 (2.2); 7.0859 (0.8); 7.0746 (0.9); 7.0699 (3.0); 6.9563 (2.3); 6.9365 (1.7); 4.1578 (15.7);
3.8505 (16.0); 2.2527 (8.0); 1.5722 (1.7); -0.0002 (10.7) 3.8505 (16.0); 2.2527 (8.0); 1.5722 (1.7); -0.0002 (10.7)
1-363: 1H-NMR(400.0 MHz, CDC13):  1-363: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4945 (3.3); 8.4825 (3.4); 7.2607 (35.4); 7.0538 (1.2); 7.0418 (2.4); 7.0299 (1.2); 6.5510 (1.6); 6.5346 (1.8); 6.5292 (1.9);δ = 8.4945 (3.3); 8.4825 (3.4); 7.2607 (35.4); 7.0538 (1.2); 7.0418 (2.4); 7.0299 (1.2); 6.5510 (1.6); 6.5346 (1.8); 6.5292 (1.9);
6.5128 (1.6); 6.5088 (0.5); 4.1263 (15.6); 3.9589 (16.0); 2.0050 (0.6); -0.0002 (13.6); -0.0085 (0.6) 6.5128 (1.6); 6.5088 (0.5); 4.1263 (15.6); 3.9589 (16.0); 2.0050 (0.6); -0.0002 (13.6); -0.0085 (0.6)
1-364: 1H-NMR(400.0 MHz, CDC13):  1-364: 1H NMR (400.0 MHz, CDC13):
δ= 8.3474 (9.5); 7.2604 (33.2); 6.5879 (1.6); 6.5714 (1.9); 6.5662 (1.9); 6.5498 (1.6); 4.1204 (15.9); 3.9599 (16.0); 2.0055 (0.7);δ = 8.3474 (9.5); 7.2604 (33.2); 6.5879 (1.6); 6.5714 (1.9); 6.5662 (1.9); 6.5498 (1.6); 4.1204 (15.9); 3.9599 (16.0); 2.0055 (0.7);
-0.0002 (12.7) -0.0002 (12.7)
1-365: 1H-NMR(400.0 MHz, CDC13):  1-365: 1H NMR (400.0 MHz, CDC13):
δ= 8.3300 (5.4); 8.3181 (5.6); 7.2609 (17.5); 7.1896 (2.4); 7.1843 (0.8); 7.1729 (0.9); 7.1676 (2.6); 7.1377 (0.5); 7.1236 (0.7); 7.1189 (1.9); 7.1163 (1.5); 7.1030 (5.4); 7.0975 (4.2); 7.0857 (0.6); 7.0812 (1.0); 7.0663 (0.8); 7.0619 (0.7); 7.0598 (0.5); 7.0449 (0.9); 6.9942 (1.6); 6.9822 (3.0); 6.9703 (1.5); 6.7224 (3.1); 6.7171 (1.0); 6.7058 (0.9); 6.7006 (2.8); 5.2965 (2.5); 5.2909 (5.2); 4.3385 (1.1); 4.3207 (3.6); 4.3029 (3.6); 4.2851 (1.1); 3.7304 (16.0); 1.2246 (3.7); 1.2068 (8.0); 1.1890 (3.6); -0.0002 (6.8) 1-366: 1H-NMR(400.0 MHz, CDC13): δ = 8.3300 (5.4); 8.3181 (5.6); 7.2609 (17.5); 7.1896 (2.4); 7.1843 (0.8); 7.1729 (0.9); 7.1676 (2.6); 7.1377 (0.5); 7.1236 (0.7); 7.1189 (1.9); 7.1163 (1.5); 7.1030 (5.4); 7.0975 (4.2); 7.0857 (0.6); 7.0812 (1.0); 7.0663 (0.8); 7.0619 (0.7); 7.0598 (0.5); 7.0449 (0.9); 6.9942 (1.6); 6.9822 (3.0); 6.9703 (1.5); 6.7224 (3.1); 6.7171 (1.0); 6.7058 (0.9); 6.7006 (2.8); 5.2965 (2.5); 5.2909 (5.2); 4.3385 (1.1); 4.3207 (3.6); 4.3029 (3.6); 4.2851 (1.1); 3.7304 (16.0); 1.2246 (3.7); 1.2068 (8.0); 1.1890 (3.6); -0.0002 (6.8) 1-366: 1H-NMR (400.0 MHz, CDC13):
δ= 8.1096 (8.8); 7.2605 (11.1); 6.9007 (0.8); 6.8968 (0.8); 6.8802 (1.2); 6.8208 (2.3); 6.8196 (2.3); 6.8014 (1.3); 3.7468 (12.9);δ = 8.1096 (8.8); 7.2605 (11.1); 6.9007 (0.8); 6.8968 (0.8); 6.8802 (1.2); 6.8208 (2.3); 6.8196 (2.3); 6.8014 (1.3); 3.7468 (12.9);
2.3816 (16.0); 2.3109 (12.7); -0.0002 (4.4) 2.3816 (16.0); 2.3109 (12.7); -0.0002 (4.4)
1-367: 1H-NMR(400.0 MHz, CDC13):  1-367: 1H-NMR (400.0 MHz, CDC13):
δ= 8.6063 (1.1); 8.5944 (1.2); 8.4888 (2.1); 8.4769 (2.2); 8.1944 (0.9); 8.1880 (0.9); 7.2611 (39.5); 7.2409 (0.6); 7.2336 (0.6); 7.2207 (0.7); 7.2189 (0.8); 7.2134 (0.7); 7.2116 (0.8); 7.1988 (0.7); 7.1915 (0.7); 7.1117 (0.9); 7.0528 (1.8); 7.0409 (2.6); 7.0289 (1.4); 7.0210 (0.6); 4.2179 (15.1); 4.2022 (6.1); 3.9482 (6.2); 3.7912 (16.0); -0.0002 (14.8); -0.0085 (0.6) 1-368: 1H-NMR(400.0 MHz, CDC13): δ = 8.6063 (1.1); 8.5944 (1.2); 8.4888 (2.1); 8.4769 (2.2); 8.1944 (0.9); 8.1880 (0.9); 7.2611 (39.5); 7.2409 (0.6); 7.2336 (0.6); 7.2207 (0.7); 7.2189 (0.8); 7.2134 (0.7); 7.2116 (0.8); 7.1988 (0.7); 7.1915 (0.7); 7.1117 (0.9); 7.0528 (1.8); 7.0409 (2.6); 7.0289 (1.4); 7.0210 (0.6); 4.2179 (15.1); 4.2022 (6.1); 3.9482 (6.2); 3.7912 (16.0); -0.0002 (14.8); -0.0085 (0.6) 1-368: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4163 (12.0); 7.3102 (0.5); 7.2602 (52.4); 6.9765 (0.6); 6.9632 (0.6); 6.9535 (1.2); 6.9402 (1.2); 6.9304 (0.7); 6.9171 (0.6); 6.8157 (0.6); 6.8081 (0.6); 6.7949 (0.6); 6.7880 (1.0); 6.7814 (0.7); 6.7680 (0.6); 6.7606 (0.8); 6.6823 (0.5); 6.6781 (0.6); 6.6747δ = 8.4163 (12.0); 7.3102 (0.5); 7.2602 (52.4); 6.9765 (0.6); 6.9632 (0.6); 6.9535 (1.2); 6.9402 (1.2); 6.9304 (0.7); 6.9171 (0.6); 6.8157 (0.6); 6.8081 (0.6); 6.7949 (0.6); 6.7880 (1.0); 6.7814 (0.7); 6.7680 (0.6); 6.7606 (0.8); 6.6823 (0.5); 6.6781 (0.6); 6.6747
(0.7); 6.6708 (0.6); 5.2987 (0.6); 3.7587 (16.0); 2.2061 (15.0); 1.5426 (10.7); 0.0079 (0.5); -0.0002 (18.4); -0.0085 (0.7) (0.7); 6.6708 (0.6); 5.2987 (0.6); 3.7587 (16.0); 2.2061 (15.0); 1.5426 (10.7); 0.0079 (0.5); -0.0002 (18.4); -0.0085 (0.7)
1-369: 1H-NMR(400.0 MHz, CDC13):  1-369: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3336 (1.2); 8.3296 (1.2); 8.3275 (1.2); 7.8342 (0.8); 7.8291 (0.8); 7.8127 (0.8); 7.8075 (0.8); 7.2602 (31.3); 6.9640 (1.7); 6.9519 (0.6); 6.9422 (2.5); 6.9289 (1.2); 6.9192 (0.7); 6.9059 (0.6); 6.7820 (0.6); 6.7746 (0.7); 6.7612 (0.6); 6.7544 (1.0); 6.7477 (0.7); 6.7343 (0.6); 6.7269 (0.7); 6.6677 (0.5); 6.6635 (0.7); 6.6600 (0.8); 6.6564 (0.6); 3.7592 (16.0); 2.2122 (15.0); 1.5447 (2.3); -0.0002 (11.1) δ = 8.3336 (1.2); 8.3296 (1.2); 8.3275 (1.2); 7.8342 (0.8); 7.8291 (0.8); 7.8127 (0.8); 7.8075 (0.8); 7.2602 (31.3); 6.9640 (1.7); 6.9519 (0.6); 6.9422 (2.5); 6.9289 (1.2); 6.9192 (0.7); 6.9059 (0.6); 6.7820 (0.6); 6.7746 (0.7); 6.7612 (0.6); 6.7544 (1.0); 6.7477 (0.7); 6.7343 (0.6); 6.7269 (0.7); 6.6677 (0.5); 6.6635 (0.7); 6.6600 (0.8); 6.6564 (0.6); 3.7592 (16.0); 2.2122 (15.0); 1.5447 (2.3); -0.0002 (11.1)
1-370: 1H-NMR(400.0 MHz, CDC13):  1-370: 1H NMR (400.0 MHz, CDC13):
δ= 8.6139 (0.6); 8.6019 (0.6); 8.4643 (8.9); 8.4524 (9.2); 7.2611 (35.9); 7.2596 (29.3); 7.2051 (2.5); 7.2010 (3.5); 7.1957 (1.4); 7.1824 (6.6); 7.1808 (6.7); 7.1629 (2.4); 7.1601 (3.5); 7.1548 (1.2); 7.1428 (6.7); 7.1386 (2.6); 7.1231 (3.3); 7.1059 (1.8); 7.1021 (3.0); 7.0986 (1.7); 7.0910 (1.2); 7.0843 (3.1); 7.0774 (0.8); 7.0670 (0.9); 7.0267 (2.8); 7.0147 (5.3); 7.0028 (2.7); 5.2978 (5.8); 5.2964 (4.6); 4.4552 (0.5); 4.4374 (0.5); 4.3627 (2.4); 4.3449 (7.4); 4.3270 (7.6); 4.3091 (2.6); 3.8026 (0.7); 2.0456 (1.2); 1.4446 (0.6); 1.4269 (1.1); 1.4080 (0.7); 1.3898 (0.5); 1.2749 (0.6); 1.2515 (8.2); 1.2337 (16.0); 1.2158 (7.6); -0.0002 (12.9); -0.0017δ = 8.6139 (0.6); 8.6019 (0.6); 8.4643 (8.9); 8.4524 (9.2); 7.2611 (35.9); 7.2596 (29.3); 7.2051 (2.5); 7.2010 (3.5); 7.1957 (1.4); 7.1824 (6.6); 7.1808 (6.7); 7.1629 (2.4); 7.1601 (3.5); 7.1548 (1.2); 7.1428 (6.7); 7.1386 (2.6); 7.1231 (3.3); 7.1059 (1.8); 7.1021 (3.0); 7.0986 (1.7); 7.0910 (1.2); 7.0843 (3.1); 7.0774 (0.8); 7.0670 (0.9); 7.0267 (2.8); 7.0147 (5.3); 7.0028 (2.7); 5.2978 (5.8); 5.2964 (4.6); 4.4552 (0.5); 4.4374 (0.5); 4.3627 (2.4); 4.3449 (7.4); 4.3270 (7.6); 4.3091 (2.6); 3.8026 (0.7); 2.0456 (1.2); 1.4446 (0.6); 1.4269 (1.1); 1.4080 (0.7); 1.3898 (0.5); 1.2749 (0.6); 1.2515 (8.2); 1.2337 (16.0); 1.2158 (7.6); -0.0002 (12.9); -0.0017
(10-1) (10-1)
1-371 : 1H-NMR(400.0 MHz, CDC13):  1-371: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4985 (9.6); 8.4865 (9.8); 8.3901 (0.6); 8.3782 (0.6); 7.5189 (0.8); 7.2600 (138.3); 7.0749 (3.6); 7.0715 (1.0); 7.0629 (5.5); 7.0571 (1.2); 7.0552 (1.2); 7.0510 (3.6); 7.0464 (1.2); 7.0329 (1.0); 7.0274 (1.1); 6.9961 (1.0); 6.9848 (0.6); 6.9793 (3.0); 6.9753 (2.7); 6.9702 (1.5); 6.9670 (1.9); 6.9657 (1.9); 6.9631 (2.9); 6.9584 (3.3); 6.9434 (1.7); 5.2565 (0.6); 4.4081 (2.3); 4.3903 (7.3); 4.3724 (7.4); 4.3664 (0.8); 4.3546 (2.4); 4.3485 (0.6); 3.8089 (1.4); 3.7898 (0.7); 2.0443 (2.1); 1.3244 (7.7); 1.3066 (16.0); 1.2977 (1.0); 1.2888 (7.7); 1.2798 (1.4); 1.2767 (1.5); 1.2620 (1.4); 1.2588 (2.1); 1.2409 (0.7); 0.8818 (1.5); 0.8641 (0.6); 0.0079δ = 8.4985 (9.6); 8.4865 (9.8); 8.3901 (0.6); 8.3782 (0.6); 7.5189 (0.8); 7.2600 (138.3); 7.0749 (3.6); 7.0715 (1.0); 7.0629 (5.5); 7.0571 (1.2); 7.0552 (1.2); 7.0510 (3.6); 7.0464 (1.2); 7.0329 (1.0); 7.0274 (1.1); 6.9961 (1.0); 6.9848 (0.6); 6.9793 (3.0); 6.9753 (2.7); 6.9702 (1.5); 6.9670 (1.9); 6.9657 (1.9); 6.9631 (2.9); 6.9584 (3.3); 6.9434 (1.7); 5.2565 (0.6); 4.4081 (2.3); 4.3903 (7.3); 4.3724 (7.4); 4.3664 (0.8); 4.3546 (2.4); 4.3485 (0.6); 3.8089 (1.4); 3.7898 (0.7); 2.0443 (2.1); 1.3244 (7.7); 1.3066 (16.0); 1.2977 (1.0); 1.2888 (7.7); 1.2798 (1.4); 1.2767 (1.5); 1.2620 (1.4); 1.2588 (2.1); 1.2409 (0.7); 0.8818 (1.5); 0.8641 (0.6); 0.0079
(1.7); -0.0002 (53.4); -0.0085 (2.0) (1.7); -0.0002 (53.4); -0.0085 (2.0)
1-372: 1H-NMR(400.0 MHz, CDC13):  1-372: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4709 (5.0); 8.4590 (5.1); 7.3357 (0.5); 7.3165 (1.2); 7.2960 (0.9); 7.2605 (39.8); 7.2107 (1.3); 7.1867 (1.3); 7.1803 (1.5); 7.1412 (0.9); 7.1353 (0.7); 7.1207 (0.7); 6.9873 (1.6); 6.9753 (3.1); 6.9634 (1.6); 3.7925 (16.0); 2.1622 (15.5); 1.5489 (9.3); -δ = 8.4709 (5.0); 8.4590 (5.1); 7.3357 (0.5); 7.3165 (1.2); 7.2960 (0.9); 7.2605 (39.8); 7.2107 (1.3); 7.1867 (1.3); 7.1803 (1.5); 7.1412 (0.9); 7.1353 (0.7); 7.1207 (0.7); 6.9873 (1.6); 6.9753 (3.1); 6.9634 (1.6); 3.7925 (16.0); 2.1622 (15.5); 1.5489 (9.3); -
0.0002 (15.1); -0.0085 (0.8) 0.0002 (15.1); -0.0085 (0.8)
1-373: 1H-NMR(400.0 MHz, CDC13):  1-373: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3257 (10.2); 7.2613 (15.2); 6.8919 (0.6); 6.8846 (2.9); 6.8808 (0.7); 6.8783 (1.1); 6.8721 (3.0); 6.8656 (3.8); 6.8599 (3.6);δ = 8.3257 (10.2); 7.2613 (15.2); 6.8919 (0.6); 6.8846 (2.9); 6.8808 (0.7); 6.8783 (1.1); 6.8721 (3.0); 6.8656 (3.8); 6.8599 (3.6);
6.8563 (0.7); 6.8501 (0.5); 5.2982 (0.6); 3.7615 (16.0); 2.1569 (15.5); 1.5624 (1.6); -0.0002 (9.2) 6.8563 (0.7); 6.8501 (0.5); 5.2982 (0.6); 3.7615 (16.0); 2.1569 (15.5); 1.5624 (1.6); -0.0002 (9.2)
1-374: 1H-NMR(400.0 MHz, CDC13):  1-374: 1H NMR (400.0 MHz, CDC13):
δ= 8.3583 (1.2); 8.3545 (1.2); 8.3524 (1.2); 7.8195 (0.8); 7.8133 (0.8); 7.7978 (0.8); 7.7917 (0.8); 7.2602 (18.2); 6.9522 (1.5); 6.9404 (0.5); 6.9307 (1.4); 6.8973 (0.9); 6.8910 (0.6); 6.8807 (1.1); 6.8781 (0.9); 6.8738 (2.9); 6.8662 (0.6); 6.8614 (0.6); 6.8542 (3.0); 6.8480 (3.2); 6.8434 (0.8); 6.8414 (0.9); 6.8367 (3.0); 6.8312 (0.7); 6.8297 (0.7); 6.8246 (0.9); 6.8128 (0.6); 5.2978 (1.2); 3.8696 (2.8); 3.7620 (16.0); 3.6386 (2.6); 3.1475 (0.7); 2.3930 (0.6); 2.1662 (14.0); 2.1572 (0.5); 2.0751 (2.6); 1.5536 (2.8); -δ = 8.3583 (1.2); 8.3545 (1.2); 8.3524 (1.2); 7.8195 (0.8); 7.8133 (0.8); 7.7978 (0.8); 7.7917 (0.8); 7.2602 (18.2); 6.9522 (1.5); 6.9404 (0.5); 6.9307 (1.4); 6.8973 (0.9); 6.8910 (0.6); 6.8807 (1.1); 6.8781 (0.9); 6.8738 (2.9); 6.8662 (0.6); 6.8614 (0.6); 6.8542 (3.0); 6.8480 (3.2); 6.8434 (0.8); 6.8414 (0.9); 6.8367 (3.0); 6.8312 (0.7); 6.8297 (0.7); 6.8246 (0.9); 6.8128 (0.6); 5.2978 (1.2); 3.8696 (2.8); 3.7620 (16.0); 3.6386 (2.6); 3.1475 (0.7); 2.3930 (0.6); 2.1662 (14.0); 2.1572 (0.5); 2.0751 (2.6); 1.5536 (2.8); -
0.0002 (10.4) 0.0002 (10.4)
1-375: 1H-NMR(400.0 MHz, CDC13):  1-375: 1H NMR (400.0 MHz, CDC13):
δ= 8.4973 (5.5); 8.4853 (5.6); 7.2610 (27.5); 7.0032 (1.7); 6.9912 (3.2); 6.9793 (1.6); 6.8765 (12.3); 6.8609 (9.1); 3.7712 (16.0);δ = 8.4973 (5.5); 8.4853 (5.6); 7.2610 (27.5); 7.0032 (1.7); 6.9912 (3.2); 6.9793 (1.6); 6.8765 (12.3); 6.8609 (9.1); 3.7712 (16.0);
2.1609 (15.4); 1.5570 (4.0); 0.0080 (0.5); -0.0002 (15.3); -0.0085 (0.5) 2.1609 (15.4); 1.5570 (4.0); 0.0080 (0.5); -0.0002 (15.3); -0.0085 (0.5)
1-376: 1H-NMR(400.0 MHz, CDC13):  1-376: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4283 (0.7); 8.4057 (11.9); 7.2608 (23.6); 6.8952 (0.7); 6.8882 (2.8); 6.8817 (0.8); 6.8796 (0.8); 6.8732 (3.2); 6.8691 (3.6); 6.8659 (1.8); 6.8612 (3.4); 6.8573 (0.7); 6.8510 (0.6); 3.7625 (16.0); 3.6680 (0.7); 2.1559 (15.6); 2.0929 (0.6); 1.5531 (7.4); -δ = 8.4283 (0.7); 8.4057 (11.9); 7.2608 (23.6); 6.8952 (0.7); 6.8882 (2.8); 6.8817 (0.8); 6.8796 (0.8); 6.8732 (3.2); 6.8691 (3.6); 6.8659 (1.8); 6.8612 (3.4); 6.8573 (0.7); 6.8510 (0.6); 3.7625 (16.0); 3.6680 (0.7); 2.1559 (15.6); 2.0929 (0.6); 1.5531 (7.4); -
0.0002 (13.1) 0.0002 (13.1)
1-377: 1H-NMR(400.0 MHz, CDC13):  1-377: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3450 (10.7); 7.2622 (13.4); 7.0233 (0.5); 7.0008 (1.1); 6.9763 (1.1); 6.9539 (0.6); 6.7964 (0.5); 6.7889 (0.6); 6.7800 (0.6); 6.7725 (0.6); 6.7675 (0.6); 6.7600 (0.6); 6.7511 (0.5); 6.7436 (0.6); 6.6592 (0.7); 6.6548 (0.6); 6.6365 (0.6); 6.6321 (0.6); 5.2987δ = 8.3450 (10.7); 7.2622 (13.4); 7.0233 (0.5); 7,0008 (1.1); 6.9763 (1.1); 6.9539 (0.6); 6.7964 (0.5); 6.7889 (0.6); 6.7800 (0.6); 6.7725 (0.6); 6.7675 (0.6); 6.7600 (0.6); 6.7511 (0.5); 6.7436 (0.6); 6.6592 (0.7); 6.6548 (0.6); 6.6365 (0.6); 6.6321 (0.6); 5.2987
(0.9); 3.7697 (16.0); 2.1583 (15.5); 1.5658 (3.1); -0.0002 (7.7) (0.9); 3.7697 (16.0); 2.1583 (15.5); 1.5658 (3.1); -0.0002 (7.7)
1-378: 1H-NMR(400.0 MHz, CDC13):  1-378: 1H-NMR (400.0 MHz, CDC13):
δ= 8.5053 (4.1); 8.4933 (4.2); 7.2631 (11.1); 7.0196 (1.6); 7.0077 (3.2); 6.9957 (1.6); 6.9828 (1.1); 6.9582 (1.1); 6.9358 (0.6); 6.8050 (0.5); 6.7974 (0.6); 6.7885 (0.6); 6.7810 (0.6); 6.7759 (0.6); 6.7684 (0.6); 6.7595 (0.5); 6.7520 (0.6); 6.6665 (0.6); 6.6621δ = 8.5053 (4.1); 8.4933 (4.2); 7.2631 (11.1); 7.0196 (1.6); 7.0077 (3.2); 6.9957 (1.6); 6.9828 (1.1); 6.9582 (1.1); 6.9358 (0.6); 6.8050 (0.5); 6.7974 (0.6); 6.7885 (0.6); 6.7810 (0.6); 6.7759 (0.6); 6.7684 (0.6); 6.7595 (0.5); 6.7520 (0.6); 6.6665 (0.6); 6.6621
(0.6); 6.6438 (0.6); 6.6394 (0.6); 5.2986 (1.0); 3.7740 (16.0); 2.1613 (15.6); 1.5816 (2.6); -0.0002 (6.2) (0.6); 6.6438 (0.6); 6.6394 (0.6); 5.2986 (1.0); 3.7740 (16.0); 2.1613 (15.6); 1.5816 (2.6); -0.0002 (6.2)
1-379: 1H-NMR(400.0 MHz, CDC13):  1-379: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4962 (3.4); 8.4843 (3.4); 7.2621 (12.8); 7.1012 (0.8); 7.0980 (0.5); 7.0828 (0.8); 7.0796 (1.4); 7.0612 (0.8); 7.0594 (0.9); 6.9893 (1.4); 6.9773 (2.7); 6.9654 (1.4); 6.5266 (0.7); 6.5245 (0.9); 6.5209 (0.9); 6.5187 (1.2); 6.5115 (0.8); 6.5093 (0.8); 6.5056 (1.6); 6.5029 (1.7); 6.4983 (1.2); 6.4901 (1.6); 6.4871 (3.6); 6.4841 (2.4); 6.4786 (0.7); 5.2975 (1.1); 3.7647 (14.7); 3.7263δ = 8.4962 (3.4); 8.4843 (3.4); 7.2621 (12.8); 7.1012 (0.8); 7.0980 (0.5); 7.0828 (0.8); 7.0796 (1.4); 7.0612 (0.8); 7.0594 (0.9); 6.9893 (1.4); 6.9773 (2.7); 6.9654 (1.4); 6.5266 (0.7); 6.5245 (0.9); 6.5209 (0.9); 6.5187 (1.2); 6.5115 (0.8); 6.5093 (0.8); 6.5056 (1.6); 6.5029 (1.7); 6.4983 (1.2); 6.4901 (1.6); 6.4871 (3.6); 6.4841 (2.4); 6.4786 (0.7); 5.2975 (1.1); 3.7647 (14.7); 3.7263
(16.0) ; 2.1556 (14.3); 1.5916 (0.5); -0.0002 (6.9) (16.0); 2.1556 (14.3); 1.5916 (0.5); -0.0002 (6.9)
1-380: 1H-NMR(400.0 MHz, CDC13):  1-380: 1H NMR (400.0 MHz, CDC13):
δ= 8.3215 (9.7); 7.2600 (29.3); 7.1098 (1.0); 7.0895 (2.2); 7.0690 (1.2); 6.5221 (0.6); 6.5202 (0.9); 6.5162 (0.8); 6.5143 (1.2); 6.5110 (0.9); 6.5090 (0.8); 6.5049 (1.3); 6.5025 (1.1); 6.4995 (0.8); 6.4959 (0.9); 6.4937 (1.1); 6.4909 (0.7); 6.4886 (0.7); 6.4847 (1.3); 6.4826 (0.9); 6.4740 (1.6); 6.4683 (2.0); 6.4626 (0.8); 3.7615 (15.2); 3.7345 (16.0); 2.1753 (0.5); 2.1562 (14.8); 1.5457δ = 8.3215 (9.7); 7.2600 (29.3); 7.1098 (1.0); 7.0895 (2.2); 7.0690 (1.2); 6.5221 (0.6); 6.5202 (0.9); 6.5162 (0.8); 6.5143 (1.2); 6.5110 (0.9); 6.5090 (0.8); 6.5049 (1.3); 6.5025 (1.1); 6.4995 (0.8); 6.4959 (0.9); 6.4937 (1.1); 6.4909 (0.7); 6.4886 (0.7); 6.4847 (1.3); 6.4826 (0.9); 6.4740 (1.6); 6.4683 (2.0); 6.4626 (0.8); 3.7615 (15.2); 3.7345 (16.0); 2.1753 (0.5); 2.1562 (14.8); 1.5457
(5.6); 0.0691 (0.5); 0.0079 (0.6); -0.0002 (16.7); -0.0084 (0.6) (5.6); 0.0691 (0.5); 0.0079 (0.6); -0.0002 (16.7); -0.0084 (0.6)
1-392: 1H-NMR(400.0 MHz, CDC13):  1-392: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4671 (4.6); 8.4552 (4.8); 7.2608 (46.7); 7.1978 (1.3); 7.1931 (0.5); 7.1778 (1.8); 7.1764 (1.9); 7.1602 (0.9); 7.1565 (1.7); 7.0033 (1.2); 6.9967 (3.0); 6.9843 (3.2); 6.9804 (2.3); 6.9769 (1.6); 6.9727 (1.6); 6.9251 (0.6); 6.9224 (1.0); 6.9196 (1.4); 6.9167 (1.5); 6.9141 (1.1); 6.9021 (3.2); 6.8995 (3.9); 6.8967 (3.0); 3.8617 (16.0); 2.2979 (14.7); 1.5544 (9.5); 0.0080 (0.5); -0.0002δ = 8.4671 (4.6); 8.4552 (4.8); 7.2608 (46.7); 7.1978 (1.3); 7.1931 (0.5); 7.1778 (1.8); 7.1764 (1.9); 7.1602 (0.9); 7.1565 (1.7); 7.0033 (1.2); 6.9967 (3.0); 6.9843 (3.2); 6.9804 (2.3); 6.9769 (1.6); 6.9727 (1.6); 6.9251 (0.6); 6.9224 (1.0); 6.9196 (1.4); 6.9167 (1.5); 6.9141 (1.1); 6.9021 (3.2); 6.8995 (3.9); 6.8967 (3.0); 3.8617 (16.0); 2.2979 (14.7); 1.5544 (9.5); 0.0080 (0.5); -0.0002
(17.1) ; -0.0084 (0.8) 1-394: 1H-NMR(400.0 MHz, CDC13): (17.1); -0.0084 (0.8) 1-394: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4852 (5.4); 8.4733 (5.5); 7.2611 (17.9); 7.0767 (1.3); 7.0568 (2.5); 7.0369 (1.5); 6.9965 (1.6); 6.9845 (2.9); 6.9726 (1.5); 6.6616 (1.4); 6.6424 (1.4); 6.6277 (1.5); 6.6221 (2.5); 6.6177 (1.7); 6.6039 (1.4); 6.5982 (0.9); 6.5834 (1.2); 6.5778 (0.9); 5.2975 (3.8); 3.9678 (1.3); 3.9503 (3.9); 3.9328 (4.0); 3.9154 (1.3); 3.8382 (16.0); 2.3014 (15.6); 1.5683 (4.4); 1.3825 (4.1); 1.3651δ = 8.4852 (5.4); 8.4733 (5.5); 7.2611 (17.9); 7.0767 (1.3); 7.0568 (2.5); 7.0369 (1.5); 6.9965 (1.6); 6.9845 (2.9); 6.9726 (1.5); 6.6616 (1.4); 6.6424 (1.4); 6.6277 (1.5); 6.6221 (2.5); 6.6177 (1.7); 6.6039 (1.4); 6.5982 (0.9); 6.5834 (1.2); 6.5778 (0.9); 5.2975 (3.8); 3.9678 (1.3); 3.9503 (3.9); 3.9328 (4.0); 3.9154 (1.3); 3.8382 (16.0); 2.3014 (15.6); 1.5683 (4.4); 1.3825 (4.1); 1.3651
(8.2) ; 1.3476 (3.9); -0.0002 (6.4) (8.2); 1.3476 (3.9); -0.0002 (6.4)
1-408: 1H-NMR(400.0 MHz, CDC13):  1-408: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4545 (0.6); 8.4455 (0.6); 8.3125 (4.8); 8.3035 (4.8); 7.3215 (0.6); 7.2693 (11.6); 7.2604 (11.7); 6.2263 (4.6); 6.2231 (4.5); 6.1812 (2.5); 3.8881 (0.6); 3.8319 (8.0); 3.8229 (8.0); 3.7753 (1.3); 3.7520 (1.9); 3.7212 (15.9); 3.7122 (16.0); 2.3151 (7.7);δ = 8.4545 (0.6); 8.4455 (0.6); 8.3125 (4.8); 8.3035 (4.8); 7.3215 (0.6); 7.2693 (11.6); 7.2604 (11.7); 6.2263 (4.6); 6.2231 (4.5); 6.1812 (2.5); 3.8881 (0.6); 3.8319 (8.0); 3.8229 (8.0); 3.7753 (1.3); 3.7520 (1.9); 3.7212 (15.9); 3.7122 (16.0); 2.3151 (7.7);
2.3060 (8.1); 1.5582 (2.4); 0.0086 (4.5); -0.0002 (4.6) 2.3060 (8.1); 1.5582 (2.4); 0.0086 (4.5); -0.0002 (4.6)
1-409: 1H-NMR(400.0 MHz, CDC13):  1-409: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4929 (4.0); 7.2700 (9.0); 7.2611 (9.1); 7.0007 (1.8); 6.9906 (1.8); 6.9791 (0.8); 6.2501 (4.8); 6.2468 (4.6); 6.1737 (2.3); 3.8911 (0.6); 3.8358 (7.9); 3.8268 (7.8); 3.7160 (16.0); 3.7070 (16.0); 2.3115 (7.7); 2.3025 (7.7); 2.2353 (0.5); 1.5732 (1.2);δ = 8.4929 (4.0); 7.2700 (9.0); 7.2611 (9.1); 7,0007 (1.8); 6.9906 (1.8); 6.9791 (0.8); 6.2501 (4.8); 6.2468 (4.6); 6.1737 (2.3); 3.8911 (0.6); 3.8358 (7.9); 3.8268 (7.8); 3.7160 (16.0); 3.7070 (16.0); 2.3115 (7.7); 2.3025 (7.7); 2.2353 (0.5); 1.5732 (1.2);
0.0087 (3.5); -0.0002 (3.5) 0.0087 (3.5); -0.0002 (3.5)
1-410: 1H-NMR(400.0 MHz, CDC13):  1-410: 1H NMR (400.0 MHz, CDC13):
δ= 8.2578 (10.8); 7.2619 (39.0); 6.7663 (3.3); 6.7647 (3.1); 6.7169 (1.4); 6.7152 (1.4); 4.1782 (15.6); 3.8604 (16.0); 2.1803δ = 8.2578 (10.8); 7.2619 (39.0); 6.7663 (3.3); 6.7647 (3.1); 6.7169 (1.4); 6.7152 (1.4); 4.1782 (15.6); 3.8604 (16.0); 2.1803
(16.0); 2.1790 (15.2); 1.5543 (10.9); -0.0002 (14.2) (16.0); 2.1790 (15.2); 1.5543 (10.9); -0.0002 (14.2)
1-411 : 1H-NMR(400.0 MHz, CDC13):  1-411: 1H NMR (400.0 MHz, CDC13):
δ= 8.2581 (10.3); 7.2622 (21.1); 7.0574 (0.5); 7.0389 (0.8); 7.0360 (1.2); 7.0212 (0.6); 7.0176 (1.0); 6.9723 (1.0); 6.9709 (1.0); 6.9694 (1.0); 6.9551 (2.1); 6.9537 (2.3); 6.9522 (2.1); 6.9125 (0.9); 6.8947 (0.7); 6.8931 (0.7); 4.1793 (15.7); 3.8443 (16.0);δ = 8.2581 (10.3); 7.2622 (21.1); 7.0574 (0.5); 7.0389 (0.8); 7.0360 (1.2); 7.0212 (0.6); 7.0176 (1.0); 6.9723 (1.0); 6.9709 (1.0); 6.9694 (1.0); 6.9551 (2.1); 6.9537 (2.3); 6.9522 (2.1); 6.9125 (0.9); 6.8947 (0.7); 6.8931 (0.7); 4.1793 (15.7); 3.8443 (16.0);
2.2236 (8.1); 1.5593 (5.4); -0.0002 (7.9) 2.2236 (8.1); 1.5593 (5.4); -0.0002 (7.9)
1-412: 1H-NMR(400.0 MHz, CDC13):  1-412: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2724 (10.1); 7.2623 (30.5); 7.0887 (0.8); 7.0693 (1.9); 7.0497 (1.4); 7.0127 (0.9); 7.0083 (1.9); 7.0041 (1.2); 6.9671 (0.8); 6.9644 (1.2); 6.9598 (1.0); 6.9501 (1.2); 6.9474 (1.6); 6.9456 (1.6); 6.9430 (1.4); 6.9402 (0.7); 6.9310 (0.8); 6.9283 (0.7); 6.9266δ = 8.2724 (10.1); 7.2623 (30.5); 7.0887 (0.8); 7.0693 (1.9); 7.0497 (1.4); 7.0127 (0.9); 7.0083 (1.9); 7.0041 (1.2); 6.9671 (0.8); 6.9644 (1.2); 6.9598 (1.0); 6.9501 (1.2); 6.9474 (1.6); 6.9456 (1.6); 6.9430 (1.4); 6.9402 (0.7); 6.9310 (0.8); 6.9283 (0.7); 6.9266
(0.8); 6.9239 (0.6); 4.1842 (15.3); 3.8526 (15.4); 2.4078 (16.0); 1.5563 (8.3); -0.0002 (11.2) (0.8); 6.9239 (0.6); 4.1842 (15.3); 3.8526 (15.4); 2.4078 (16.0); 1.5563 (8.3); -0.0002 (11.2)
1-413: 1H-NMR(400.0 MHz, CDC13):  1-413: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2662 (10.6); 7.2627 (19.9); 7.0691 (1.0); 7.0491 (1.9); 7.0292 (1.2); 6.7411 (0.8); 6.7388 (0.9); 6.7368 (1.0); 6.7346 (0.9); 6.7217 (0.7); 6.7194 (0.8); 6.7174 (0.9); 6.7151 (0.8); 6.6756 (1.1); 6.6699 (1.6); 6.6653 (1.2); 6.6328 (0.9); 6.6306 (0.9); 6.6266 (0.7); 6.6245 (0.7); 6.6122 (0.8); 6.6101 (0.8); 6.6060 (0.7); 6.6039 (0.6); 4.1808 (15.7); 3.9544 (1.0); 3.9369 (3.3); 3.9194 (3.3);δ = 8.2662 (10.6); 7.2627 (19.9); 7.0691 (1.0); 7.0491 (1.9); 7.0292 (1.2); 6.7411 (0.8); 6.7388 (0.9); 6.7368 (1.0); 6.7346 (0.9); 6.7217 (0.7); 6.7194 (0.8); 6.7174 (0.9); 6.7151 (0.8); 6.6756 (1.1); 6.6699 (1.6); 6.6653 (1.2); 6.6328 (0.9); 6.6306 (0.9); 6.6266 (0.7); 6.6245 (0.7); 6.6122 (0.8); 6.6101 (0.8); 6.6060 (0.7); 6.6039 (0.6); 4.1808 (15.7); 3.9544 (1.0); 3.9369 (3.3); 3.9194 (3.3);
3.9020 (1.0); 3.8391 (16.0); 1.5639 (4.6); 1.3903 (3.6); 1.3729 (7.5); 1.3554 (3.5); -0.0002 (7.4) 3.9020 (1.0); 3.8391 (16.0); 1.5639 (4.6); 1.3903 (3.6); 1.3729 (7.5); 1.3554 (3.5); -0.0002 (7.4)
1-414: 1H-NMR(400.0 MHz, CDC13):  1-414: 1H NMR (400.0 MHz, CDC13):
δ= 8.5127 (2.7); 8.5008 (2.7); 7.2632 (9.1); 6.9942 (0.8); 6.9822 (1.5); 6.9702 (0.7); 6.2802 (1.8); 6.2745 (2.1); 6.2100 (0.6);δ = 8.5127 (2.7); 8,5008 (2.7); 7.2632 (9.1); 6.9942 (0.8); 6.9822 (1.5); 6.9702 (0.7); 6.2802 (1.8); 6.2745 (2.1); 6.2100 (0.6);
6.2044 (1.0); 6.1987 (0.5); 3.7367 (7.3); 3.7034 (16.0); 3.5603 (2.9); 2.1622 (6.6); -0.0002 (3.4) 6.2044 (1.0); 6.1987 (0.5); 3.7367 (7.3); 3.7034 (16.0); 3.5603 (2.9); 2.1622 (6.6); -0.0002 (3.4)
1-415: 1H-NMR(400.0 MHz, CDC13):  1-415: 1H NMR (400.0 MHz, CDC13):
δ= 8.2693 (10.4); 7.2623 (28.0); 7.0871 (1.0); 7.0671 (2.0); 7.0471 (1.3); 6.7560 (0.8); 6.7538 (1.0); 6.7518 (1.0); 6.7496 (1.0); 6.7366 (0.7); 6.7344 (0.8); 6.7323 (0.9); 6.7302 (0.8); 6.6950 (1.1); 6.6892 (1.6); 6.6847 (1.2); 6.6486 (0.9); 6.6465 (0.9); 6.6423 (0.8); 6.6402 (0.7); 6.6280 (0.8); 6.6259 (0.8); 6.6217 (0.7); 6.6196 (0.6); 4.1804 (15.8); 3.8409 (16.0); 3.7249 (15.8); 1.5580δ = 8.2693 (10.4); 7.2623 (28.0); 7.0871 (1.0); 7.0671 (2.0); 7.0471 (1.3); 6.7560 (0.8); 6.7538 (1.0); 6.7518 (1.0); 6.7496 (1.0); 6.7366 (0.7); 6.7344 (0.8); 6.7323 (0.9); 6.7302 (0.8); 6.6950 (1.1); 6.6892 (1.6); 6.6847 (1.2); 6.6486 (0.9); 6.6465 (0.9); 6.6423 (0.8); 6.6402 (0.7); 6.6280 (0.8); 6.6259 (0.8); 6.6217 (0.7); 6.6196 (0.6); 4.1804 (15.8); 3.8409 (16.0); 3.7249 (15.8); 1.5580
(8.0); -0.0002 (10.5) (8.0); -0.0002 (10.5)
1-416: 1H-NMR(400.0 MHz, CDC13):  1-416: 1H NMR (400.0 MHz, CDC13):
δ= 8.5007 (5.0); 8.4887 (5.1); 7.2634 (12.6); 7.1002 (0.7); 7.0802 (1.5); 7.0605 (0.8); 6.9851 (1.5); 6.9731 (3.0); 6.9612 (1.5); 6.7200 (0.9); 6.7185 (0.9); 6.7166 (0.7); 6.7012 (0.8); 6.6996 (0.8); 6.6597 (0.6); 6.6548 (1.4); 6.6534 (1.4); 6.6494 (1.8); 6.6289δ = 8,5007 (5.0); 8.4887 (5.1); 7.2634 (12.6); 7.1002 (0.7); 7.0802 (1.5); 7.0605 (0.8); 6.9851 (1.5); 6.9731 (3.0); 6.9612 (1.5); 6.7200 (0.9); 6.7185 (0.9); 6.7166 (0.7); 6.7012 (0.8); 6.6996 (0.8); 6.6597 (0.6); 6.6548 (1.4); 6.6534 (1.4); 6.6494 (1.8); 6.6289
(0.7); 6.6225 (0.5); 3.7369 (14.4); 3.7214 (16.0); 3.5995 (4.8); 2.1572 (12.5); -0.0002 (4.6) (0.7); 6.6225 (0.5); 3.7369 (14.4); 3.7214 (16.0); 3.5995 (4.8); 2.1572 (12.5); -0.0002 (4.6)
1-417: 1H-NMR(400.0 MHz, CDC13):  1-417: 1H NMR (400.0 MHz, CDC13):
δ= 8.4983 (0.7); 8.4902 (2.3); 8.4870 (3.3); 8.4784 (2.1); 8.4750 (2.8); 7.2732 (7.9); 7.2652 (24.2); 7.2618 (32.9); 7.0166 (1.1); 7.0079 (1.2); 7.0047 (1.6); 6.9970 (0.7); 6.9928 (0.8); 6.2902 (3.2); 6.1857 (1.3); 6.1806 (1.4); 4.1500 (2.1); 4.1426 (6.1); 4.1394 (7.7); 3.8910 (4.0); 3.8837 (2.5); 3.8754 (6.4); 3.8721 (8.1); 3.6977 (4.2); 3.6901 (12.5); 3.6869 (16.0); 1.5652 (2.4); 1.5576δ = 8.4983 (0.7); 8.4902 (2.3); 8.4870 (3.3); 8.4784 (2.1); 8.4750 (2.8); 7.2732 (7.9); 7.2652 (24.2); 7.2618 (32.9); 7.0166 (1.1); 7.0079 (1.2); 7.0047 (1.6); 6.9970 (0.7); 6.9928 (0.8); 6.2902 (3.2); 6.1857 (1.3); 6.1806 (1.4); 4.1500 (2.1); 4.1426 (6.1); 4.1394 (7.7); 3.8910 (4.0); 3.8837 (2.5); 3.8754 (6.4); 3.8721 (8.1); 3.6977 (4.2); 3.6901 (12.5); 3.6869 (16.0); 1.5652 (2.4); 1.5576
(7.3) ; 1.5543 (10.6); 0.0112 (3.1); 0.0032 (9.0); -0.0002 (12.2); -0.0084 (0.8) (7.3); 1.5543 (10.6); 0.0112 (3.1); 0.0032 (9.0); -0.0002 (12.2); -0.0084 (0.8)
1-418: 1H-NMR(400.0 MHz, CDC13):  1-418: 1H NMR (400.0 MHz, CDC13):
δ= 8.3112 (5.1); 7.2616 (67.2); 6.2386 (1.5); 6.2329 (2.1); 6.2070 (0.7); 6.2014 (0.9); 3.7382 (7.3); 3.7085 (16.0); 3.5503 (2.6);δ = 8.3112 (5.1); 7.2616 (67.2); 6.2386 (1.5); 6.2329 (2.1); 6.2070 (0.7); 6.2014 (0.9); 3.7382 (7.3); 3.7085 (16.0); 3.5503 (2.6);
2.1835 (6.5); 1.5511 (15.8); 0.0079 (0.8); -0.0002 (24.8); -0.0084 (1.0) 2.1835 (6.5); 1.5511 (15.8); 0.0079 (0.8); -0.0002 (24.8); -0.0084 (1.0)
1-419: 1H-NMR(400.0 MHz, CDC13):  1-419: 1H NMR (400.0 MHz, CDC13):
δ= 8.4776 (5.4); 8.4657 (5.5); 7.2622 (26.7); 7.0704 (1.0); 7.0507 (1.6); 7.0310 (1.2); 7.0107 (1.5); 6.9987 (3.0); 6.9868 (1.4); 6.7285 (0.9); 6.7095 (0.8); 6.6771 (0.9); 6.6714 (1.3); 6.6675 (1.0); 6.6290 (0.8); 6.6273 (0.8); 6.6226 (0.6); 6.6085 (0.7); 6.6021δ = 8.4776 (5.4); 8.4657 (5.5); 7.2622 (26.7); 7.0704 (1.0); 7.0507 (1.6); 7.0310 (1.2); 7.0107 (1.5); 6.9987 (3.0); 6.9868 (1.4); 6.7285 (0.9); 6.7095 (0.8); 6.6771 (0.9); 6.6714 (1.3); 6.6675 (1.0); 6.6290 (0.8); 6.6273 (0.8); 6.6226 (0.6); 6.6085 (0.7); 6.6021
(0.6); 4.1390 (15.0); 3.9258 (5.0); 3.8619 (15.7); 3.7070 (16.0); 1.5662 (6.1); -0.0002 (10.2) (0.6); 4.1390 (15.0); 3.9258 (5.0); 3.8619 (15.7); 3.7070 (16.0); 1.5662 (6.1); -0.0002 (10.2)
1-420: 1H-NMR(400.0 MHz, CDC13):  1-420: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2674 (10.4); 7.2622 (17.6); 7.0691 (0.6); 7.0503 (0.9); 7.0474 (0.8); 7.0282 (0.9); 6.6996 (1.0); 6.6812 (0.8); 6.6799 (0.8); 6.6267 (2.3); 6.6243 (2.3); 6.6180 (0.8); 6.6100 (0.9); 4.1360 (15.0); 3.9272 (4.9); 3.8760 (16.0); 3.7124 (15.8); 1.5684 (4.3); -δ = 8.2674 (10.4); 7.2622 (17.6); 7.0691 (0.6); 7.0503 (0.9); 7.0474 (0.8); 7.0282 (0.9); 6.6996 (1.0); 6.6812 (0.8); 6.6799 (0.8); 6.6267 (2.3); 6.6243 (2.3); 6.6180 (0.8); 6.6100 (0.9); 4.1360 (15.0); 3.9272 (4.9); 3.8760 (16.0); 3.7124 (15.8); 1.5684 (4.3); -
0.0002 (6.5) 0.0002 (6.5)
1-421 : 1H-NMR(400.0 MHz, CDC13):  1-421: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2782 (5.4); 7.2626 (9.4); 6.2452 (1.7); 6.2395 (2.1); 6.1848 (0.6); 6.1791 (1.0); 4.1358 (7.6); 3.8867 (9.3); 3.6934 (16.0);δ = 8.2782 (5.4); 7.2626 (9.4); 6.2452 (1.7); 6.2395 (2.1); 6.1848 (0.6); 6.1791 (1.0); 4.1358 (7.6); 3.8867 (9.3); 3.6934 (16.0);
1.5687 (2.7); -0.0002 (3.5) 1.5687 (2.7); -0.0002 (3.5)
1-422: 1H-NMR(400.0 MHz, CDC13):  1-422: 1H NMR (400.0 MHz, CDC13):
δ= 8.4607 (5.3); 8.4488 (5.5); 7.2622 (45.7); 7.2604 (29.1); 7.0790 (1.1); 7.0589 (2.3); 7.0389 (1.4); 7.0133 (1.5); 7.0014 (3.0); 6.9894 (1.5); 6.7710 (1.4); 6.7689 (1.5); 6.7668 (1.4); 6.7515 (1.2); 6.7496 (1.3); 6.7474 (1.3); 6.7184 (1.4); 6.7125 (2.2); 6.7085 (1.5); 6.6336 (1.3); 6.6295 (1.0); 6.6274 (1.1); 6.6130 (1.2); 6.6089 (0.9); 6.6068 (1.0); 4.1852 (15.8); 3.8271 (16.0); 3.7179 (15.9); 1.5570 (12.8); -0.0002 (16.6); -0.0022 (10.7); -0.0083 (0.9) 1-441 : 1H-NMR(400.1 MHz, d6-DMSO): δ = 8.4607 (5.3); 8.4488 (5.5); 7.2622 (45.7); 7.2604 (29.1); 7.0790 (1.1); 7.0589 (2.3); 7.0389 (1.4); 7.0133 (1.5); 7.0014 (3.0); 6,984 (1.5); 6.7710 (1.4); 6.7689 (1.5); 6.7668 (1.4); 6.7515 (1.2); 6.7496 (1.3); 6.7474 (1.3); 6.7184 (1.4); 6.7125 (2.2); 6.7085 (1.5); 6.6336 (1.3); 6.6295 (1.0); 6.6274 (1.1); 6.6130 (1.2); 6.6089 (0.9); 6.6068 (1.0); 4.1852 (15.8); 3.8271 (16.0); 3.7179 (15.9); 1.5570 (12.8); -0.0002 (16.6); -0.0022 (10.7); -0.0083 (0.9) 1-441: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 12.1042 (1.2); 8.6572 (4.8); 7.2599 (1.7); 7.2412 (3.6); 7.2202 (2.1); 7.2020 (2.8); 7.1826 (1.4); 7.1151 (0.9); 7.0976 (1.2);δ = 12.1042 (1.2); 8.6572 (4.8); 7.2599 (1.7); 7.2412 (3.6); 7.2202 (2.1); 7.2020 (2.8); 7.1826 (1.4); 7.1151 (0.9); 7.0976 (1.2);
7.0815 (0.6); 3.3313 (34.2); 2.6750 (0.5); 2.5075 (75.8); 2.3335 (0.7); 1.7809 (8.1); 1.4901 (16.0); 1.2418 (1.7) 7.0815 (0.6); 3.3313 (34.2); 2.6750 (0.5); 2.5075 (75.8); 2.3335 (0.7); 1.7809 (8.1); 1.4901 (16.0); 1.2418 (1.7)
1-442: 1H-NMR(400.1 MHz, d6-DMSO):  1-442: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 8.8108 (0.5); 8.7249 (5.4); 7.3005 (1.9); 7.2824 (3.7); 7.2653 (2.6); 7.2471 (3.1); 7.2304 (1.8); 7.1529 (1.1); 7.1354 (1.4); 7.1181 (0.8); 3.5813 (9.3); 3.4326 (0.9); 3.3214 (26.2); 2.6772 (1.1); 2.5085 (95.5); 2.3350 (1.3); 1.7461 (0.4); 1.7037 (9.3);δ = 8.8108 (0.5); 8.7249 (5.4); 7.3005 (1.9); 7.2824 (3.7); 7.2653 (2.6); 7.2471 (3.1); 7.2304 (1.8); 7.1529 (1.1); 7.1354 (1.4); 7.1181 (0.8); 3.5813 (9.3); 3.4326 (0.9); 3.3214 (26.2); 2.6772 (1.1); 2.5085 (95.5); 2.3350 (1.3); 1.7461 (0.4); 1.7037 (9.3);
1.6299 (1.0); 1.5790 (0.5); 1.4663 (16.0); 1.3439 (0.7); 1.3264 (0.4); 1.3036 (0.4); 1.2430 (2.7); 0.8607 (0.3) 1.6299 (1.0); 1.5790 (0.5); 1.4663 (16.0); 1.3439 (0.7); 1.3264 (0.4); 1.3036 (0.4); 1.2430 (2.7); 0.8607 (0.3)
1-443: 1H-NMR(400.1 MHz, d6-DMSO):  1-443: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 8.6614 (3.5); 8.6496 (3.5); 7.3214 (1.6); 7.3029 (3.0); 7.2752 (1.9); 7.2650 (1.8); 7.2537 (3.6); 7.2412 (1.9); 7.2377 (1.5); 7.1572 (0.8); 7.1394 (1.2); 7.1215 (0.5); 3.7248 (0.5); 3.5782 (10.0); 3.3191 (13.0); 3.2994 (0.4); 3.2960 (0.4); 2.5105 (39.6); 2.5070 (47.9); 2.4338 (1.0); 2.3337 (0.5); 2.2919 (0.4); 1.6677 (9.9); 1.4475 (16.0); 1.2413 (0.6) δ = 8.6614 (3.5); 8.6496 (3.5); 7.3214 (1.6); 7.3029 (3.0); 7.2752 (1.9); 7.2650 (1.8); 7.2537 (3.6); 7.2412 (1.9); 7.2377 (1.5); 7.1572 (0.8); 7.1394 (1.2); 7.1215 (0.5); 3.7248 (0.5); 3.5782 (10.0); 3.3191 (13.0); 3.2994 (0.4); 3.2960 (0.4); 2.5105 (39.6); 2.5070 (47.9); 2.4338 (1.0); 2.3337 (0.5); 2.2919 (0.4); 1.6677 (9.9); 1.4475 (16.0); 1.2413 (0.6)
1-444: 1H-NMR(400.1 MHz, d6-DMSO):  1-444: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 12.0791 (2.6); 8.5723 (5.8); 8.5606 (5.6); 7.2238 (2.3); 7.2121 (3.9); 7.2004 (3.0); 7.1839 (5.8); 7.1693 (14.1); 7.1044 (1.5); 7.0953 (1.7); 7.0894 (1.8); 7.0745 (0.9); 5.7597 (0.9); 3.8939 (0.8); 3.8760 (2.1); 3.8577 (2.1); 3.8397 (0.8); 3.3193 (20.3); 2.6754 (0.4); 2.5066 (52.5); 2.3334 (0.5); 2.0626 (16.0); 2.0068 (0.5); 1.9939 (1.0); 1.4073 (8.9); 1.3890 (8.8); 1.3428 (1.0);δ = 12.0791 (2.6); 8.5723 (5.8); 8.5606 (5.6); 7.2238 (2.3); 7.2121 (3.9); 7.2004 (3.0); 7.1839 (5.8); 7.1693 (14.1); 7.1044 (1.5); 7.0953 (1.7); 7.0894 (1.8); 7.0745 (0.9); 5.7597 (0.9); 3.8939 (0.8); 3.8760 (2.1); 3.8577 (2.1); 3.8397 (0.8); 3.3193 (20.3); 2.6754 (0.4); 2.5066 (52.5); 2.3334 (0.5); 2.0626 (16.0); 2.0068 (0.5); 1.9939 (1.0); 1.4073 (8.9); 1.3890 (8.8); 1.3428 (1.0);
1.3040 (0.3); 1.2417 (4.2); 1.1980 (0.4); 1.1802 (0.5); 0.8593 (0.5) 1.3040 (0.3); 1.2417 (4.2); 1.1980 (0.4); 1.1802 (0.5); 0.8593 (0.5)
1-445: 1H-NMR(400.1 MHz, d6-DMSO):  1-445: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 12.1429 (2.3); 8.5482 (5.8); 8.5363 (5.8); 7.2269 (1.0); 7.2174 (2.1); 7.2056 (4.9); 7.1938 (2.1); 7.1839 (1.4); 7.1788 (1.8); 7.1571 (1.1); 7.1500 (1.1); 7.1451 (1.0); 7.1300 (1.0); 7.1248 (1.2); 7.1196 (1.1); 7.1145 (1.0); 7.0993 (0.9); 7.0947 (0.9); 6.9896 (1.3); 6.9851 (1.3); 6.9801 (1.3); 6.9691 (1.1); 3.9438 (0.6); 3.9259 (1.8); 3.9078 (1.8); 3.8897 (0.6); 3.3121 (13.5); 3.2884 (0.4);δ = 12.1429 (2.3); 8.5482 (5.8); 8.5363 (5.8); 7.2269 (1.0); 7.2174 (2.1); 7.2056 (4.9); 7.1938 (2.1); 7.1839 (1.4); 7.1788 (1.8); 7.1571 (1.1); 7.1500 (1.1); 7.1451 (1.0); 7.1300 (1.0); 7.1248 (1.2); 7.1196 (1.1); 7.1145 (1.0); 7.0993 (0.9); 7.0947 (0.9); 6.9896 (1.3); 6.9851 (1.3); 6.9801 (1.3); 6.9691 (1.1); 3.9438 (0.6); 3.9259 (1.8); 3.9078 (1.8); 3.8897 (0.6); 3.3121 (13.5); 3.2884 (0.4);
2.5088 (42.6); 2.5052 (51.5); 2.3321 (0.4); 2.1167 (16.0); 1.4056 (8.4); 1.3874 (8.5); 1.3413 (0.5); 1.2393 (1.9) 2.5088 (42.6); 2.5052 (51.5); 2.3321 (0.4); 2.1167 (16.0); 1.4056 (8.4); 1.3874 (8.5); 1.3413 (0.5); 1.2393 (1.9)
1-446: 1H-NMR(400.1 MHz, d6-DMSO):  1-446: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 12.0933 (2.6); 8.5409 (5.7); 8.5292 (5.6); 8.3487 (2.0); 8.3381 (2.0); 7.5883 (1.1); 7.5850 (1.1); 7.5693 (2.2); 7.5503 (1.3); 7.2137 (1.9); 7.2020 (3.3); 7.1903 (1.8); 7.1123 (1.8); 7.0977 (4.5); 7.0794 (3.3); 5.7603 (0.8); 3.9763 (0.7); 3.9582 (2.0); 3.9401 (2.1); 3.9220 (0.8); 3.3191 (15.0); 2.6760 (0.4); 2.5071 (48.8); 2.3341 (0.8); 2.2799 (0.5); 2.1850 (0.4); 2.1211 (16.0); 2.0423 (0.4); 2.0175 (0.4); 1.9999 (0.4); 1.9595 (0.3); 1.4629 (9.1); 1.4447 (9.1); 1.3426 (1.2); 1.3041 (0.8); 1.2418 (6.3); 1.1937 (0.5);δ = 12.0933 (2.6); 8.5409 (5.7); 8.5292 (5.6); 8.3487 (2.0); 8.3381 (2.0); 7.5883 (1.1); 7.5850 (1.1); 7.5693 (2.2); 7.5503 (1.3); 7.2137 (1.9); 7.2020 (3.3); 7.1903 (1.8); 7.1123 (1.8); 7.0977 (4.5); 7.0794 (3.3); 5.7603 (0.8); 3.9763 (0.7); 3.9582 (2.0); 3.9401 (2.1); 3.9220 (0.8); 3.3191 (15.0); 2.6760 (0.4); 2.5071 (48.8); 2.3341 (0.8); 2.2799 (0.5); 2.1850 (0.4); 2.1211 (16.0); 2.0423 (0.4); 2.0175 (0.4); 1.9999 (0.4); 1.9595 (0.3); 1.4629 (9.1); 1.4447 (9.1); 1.3426 (1.2); 1.3041 (0.8); 1.2418 (6.3); 1.1937 (0.5);
0.8594 (0.8); 0.8423 (0.5) 0.8594 (0.8); 0.8423 (0.5)
1-447: 1H-NMR(400.1 MHz, d6-DMSO):  1-447: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 8.5462 (5.4); 8.5344 (5.5); 8.3423 (1.7); 8.3316 (1.7); 7.5832 (0.9); 7.5796 (0.9); 7.5639 (1.8); 7.5604 (1.8); 7.5451 (1.1); 7.5412 (1.0); 7.2180 (1.6); 7.2062 (3.0); 7.1944 (1.7); 7.1096 (3.7); 7.0906 (3.9); 7.0794 (1.5); 3.9969 (0.6); 3.9789 (1.8); 3.9606δ = 8.5462 (5.4); 8.5344 (5.5); 8.3423 (1.7); 8.3316 (1.7); 7.5832 (0.9); 7.5796 (0.9); 7.5639 (1.8); 7.5604 (1.8); 7.5451 (1.1); 7.5412 (1.0); 7.2180 (1.6); 7.2062 (3.0); 7.1944 (1.7); 7.1096 (3.7); 7.0906 (3.9); 7.0794 (1.5); 3.9969 (0.6); 3.9789 (1.8); 3.9606
(1.8) ; 3.9423 (0.7); 3.6246 (15.9); 3.3108 (18.6); 2.6759 (0.6); 2.5071 (118.8); 2.3340 (0.9); 2.1553 (16.0); 1.4575 (7.7); 1.4393(1.8); 3.9423 (0.7); 3.6246 (15.9); 3.3108 (18.6); 2.6759 (0.6); 2: 5071 (118.8); 2.3340 (0.9); 2.1553 (16.0); 1.4575 (7.7); 1.4393
(7.9) ; 1.2414 (0.5) (7.9); 1.2414 (0.5)
1-448: 1H-NMR(400.1 MHz, d6-DMSO):  1-448: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 8.5579 (5.5); 8.5461 (5.6); 7.2273 (2.2); 7.2152 (3.4); 7.2070 (2.1); 7.2034 (2.4); 7.1854 (1.1); 7.1802 (1.5); 7.1660 (1.0); 7.1595 (1.3); 7.1464 (0.9); 7.1410 (1.0); 7.1359 (0.9); 7.1306 (0.9); 7.1157 (0.8); 7.1108 (0.8); 7.0057 (1.0); 7.0007 (1.0); 6.9960δ = 8.5579 (5.5); 8.5461 (5.6); 7.2273 (2.2); 7.2152 (3.4); 7.2070 (2.1); 7.2034 (2.4); 7.1854 (1.1); 7.1802 (1.5); 7.1660 (1.0); 7.1595 (1.3); 7.1464 (0.9); 7.1410 (1.0); 7.1359 (0.9); 7.1306 (0.9); 7.1157 (0.8); 7.1108 (0.8); 7.0057 (1.0); 7,0007 (1.0); 6.9960
(1.0) ; 6.9852 (0.9); 3.9688 (0.5); 3.9507 (1.4); 3.9325 (1.5); 3.9146 (0.5); 3.6324 (16.0); 3.6060 (0.4); 3.4561 (0.4); 3.3189 (14.1); 3.2958 (0.4); 2.5109 (29.6); 2.5069 (35.6); 2.3338 (0.4); 2.1474 (16.0); 2.1212 (0.4); 2.0382 (0.4); 1.3952 (7.0); 1.3769(1.0); 6.9852 (0.9); 3.9688 (0.5); 3.9507 (1.4); 3.9325 (1.5); 3.9146 (0.5); 3.6324 (16.0); 3.6060 (0.4); 3.4561 (0.4); 3.3189 (14.1); 3.2958 (0.4); 2.5109 (29.6); 2.5069 (35.6); 2.3338 (0.4); 2.1474 (16.0); 2.1212 (0.4); 2.0382 (0.4); 1.3952 (7.0); 1.3769
(7.1) ; 1.2407 (0.7) (7.1); 1.2407 (0.7)
1-449: 1H-NMR(400.1 MHz, d6-DMSO):  1-449: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 8.5807 (5.3); 8.5689 (5.3); 7.2307 (1.8); 7.2188 (3.3); 7.2070 (2.0); 7.1880 (10.0); 7.1774 (10.0); 7.1190 (0.3); 7.1087 (0.8); 7.0981 (1.3); 7.0876 (1.4); 7.0771 (0.9); 7.0663 (0.4); 3.9180 (0.6); 3.8998 (1.7); 3.8815 (1.8); 3.8632 (0.6); 3.6192 (15.9); 3.3111 (15.1); 3.2915 (0.5); 2.6761 (0.4); 2.5073 (49.8); 2.3339 (0.4); 2.0952 (16.0); 1.3977 (7.4); 1.3793 (7.5); 1.3456 (0.4);δ = 8.5807 (5.3); 8.5689 (5.3); 7.2307 (1.8); 7.2188 (3.3); 7.2070 (2.0); 7.1880 (10.0); 7.1774 (10.0); 7.1190 (0.3); 7,1087 (0.8); 7.0981 (1.3); 7.0876 (1.4); 7.0771 (0.9); 7.0663 (0.4); 3.9180 (0.6); 3.8998 (1.7); 3.8815 (1.8); 3.8632 (0.6); 3.6192 (15.9); 3.3111 (15.1); 3.2915 (0.5); 2.6761 (0.4); 2.5073 (49.8); 2.3339 (0.4); 2.0952 (16.0); 1.3977 (7.4); 1.3793 (7.5); 1.3456 (0.4);
1.2424 (0.9) 1.2424 (0.9)
1-450: 1H-NMR(400.1 MHz, d6-DMSO):  1-450: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 8.6756 (4.0); 7.2431 (0.4); 7.2232 (2.0); 7.2091 (5.6); 7.1547 (0.4); 7.1484 (0.5); 7.1398 (0.6); 7.1338 (0.6); 3.9739 (0.8);δ = 8.6756 (4.0); 7.2431 (0.4); 7.2232 (2.0); 7.2091 (5.6); 7.1547 (0.4); 7.1484 (0.5); 7.1398 (0.6); 7.1338 (0.6); 3.9739 (0.8);
3.9556 (0.8); 3.6737 (7.2); 3.3747 (5.6); 2.5609 (16.0); 2.1786 (7.2); 1.4661 (3.4); 1.4477 (3.4); 1.2949 (0.5) 3.9556 (0.8); 3.6737 (7.2); 3.3747 (5.6); 2.5609 (16.0); 2.1786 (7.2); 1.4661 (3.4); 1.4477 (3.4); 1.2949 (0.5)
1-451 : 1H-NMR(400.1 MHz, d6-DMSO):  1-451: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 8.6355 (9.2); 7.2361 (0.6); 7.2145 (1.4); 7.2099 (1.0); 7.1927 (1.1); 7.1878 (1.5); 7.1662 (0.8); 7.1473 (0.8); 7.1427 (0.9); 7.1273 (0.9); 7.1224 (1.0); 7.1173 (1.0); 7.1123 (1.0); 7.0970 (0.9); 7.0926 (0.8); 6.9813 (1.2); 3.9851 (0.5); 3.9671 (1.5); 3.9490 (1.6); 3.9313 (0.6); 3.6308 (16.0); 3.4394 (0.4); 3.3164 (10.9); 3.2932 (0.4); 2.5069 (39.3); 2.3338 (0.4); 2.1640 (16.0); 2.0132δ = 8.6355 (9.2); 7.2361 (0.6); 7.2145 (1.4); 7.2099 (1.0); 7.1927 (1.1); 7.1878 (1.5); 7.1662 (0.8); 7.1473 (0.8); 7.1427 (0.9); 7.1273 (0.9); 7.1224 (1.0); 7.1173 (1.0); 7.1123 (1.0); 7.0970 (0.9); 7.0926 (0.8); 6.9813 (1.2); 3.9851 (0.5); 3.9671 (1.5); 3.9490 (1.6); 3.9313 (0.6); 3.6308 (16.0); 3.4394 (0.4); 3.3164 (10.9); 3.2932 (0.4); 2.5069 (39.3); 2.3338 (0.4); 2.1640 (16.0); 2.0132
(0.4); 1.4048 (7.2); 1.3866 (7.3); 1.2408 (0.3) (0.4); 1.4048 (7.2); 1.3866 (7.3); 1.2408 (0.3)
1-452: 1H-NMR(400.1 MHz, d6-DMSO):  1-452: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 8.6020 (8.8); 8.3193 (1.7); 8.3110 (1.6); 7.5847 (0.9); 7.5807 (0.9); 7.5655 (1.8); 7.5618 (1.7); 7.5465 (1.1); 7.5425 (1.0); 7.1004 (3.0); 7.0806 (2.8); 4.0219 (0.6); 4.0037 (1.8); 3.9855 (1.8); 3.9672 (0.6); 3.6238 (15.8); 3.3144 (19.3); 3.2747 (0.3); 2.6762 (0.6); 2.5074 (59.2); 2.3347 (0.9); 2.1767 (16.0); 2.0791 (0.6); 2.0278 (0.3); 2.0186 (0.4); 1.4687 (7.9); 1.4504 (7.8) 1-453: 1H-NMR(400.1 MHz, d6-DMSO): δ = 8.6020 (8.8); 8.3193 (1.7); 8.3110 (1.6); 7.5847 (0.9); 7.5807 (0.9); 7.5655 (1.8); 7.5618 (1.7); 7.5465 (1.1); 7.5425 (1.0); 7.1004 (3.0); 7.0806 (2.8); 4.0219 (0.6); 4.0037 (1.8); 3,9855 (1.8); 3.9672 (0.6); 3.6238 (15.8); 3.3144 (19.3); 3.2747 (0.3); 2.6762 (0.6); 2.5074 (59.2); 2.3347 (0.9); 2.1767 (16.0); 2.0791 (0.6); 2.0278 (0.3); 2.0186 (0.4); 1.4687 (7.9); 1.4504 (7.8) 1-453: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 12.1175 (2.6); 8.5979 (9.4); 8.3290 (2.1); 8.3187 (2.1); 7.5883 (1.2); 7.5698 (2.3); 7.5513 (1.3); 7.1135 (1.7); 7.0936 (4.2); 7.0734 (2.8); 5.7606 (0.5); 3.9998 (0.8); 3.9819 (2.1); 3.9638 (2.1); 3.9460 (0.8); 3.3200 (16.4); 2.6760 (0.5); 2.5075 (51.0); 2.3335 (0.9); 2.3011 (0.6); 2.2664 (0.5); 2.1794 (0.7); 2.1425 (16.0); 2.0917 (1.1); 2.0426 (0.9); 2.0180 (0.5); 2.0006 (0.4); 1.9818 (0.4); 1.4731 (8.8); 1.4550 (8.8); 1.3622 (0.5); 1.3429 (0.9); 1.3040 (0.7); 1.2423 (6.8); 0.8598 (0.9); 0.8428 (0.5) 1-454: 1H-NMR(400.1 MHz, d6-DMSO): δ = 12.1175 (2.6); 8.5979 (9.4); 8.3290 (2.1); 8.3187 (2.1); 7.5883 (1.2); 7.5698 (2.3); 7.5513 (1.3); 7.1135 (1.7); 7.0936 (4.2); 7.0734 (2.8); 5.7606 (0.5); 3.9998 (0.8); 3.9819 (2.1); 3.9638 (2.1); 3.9460 (0.8); 3.3200 (16.4); 2.6760 (0.5); 2.5075 (51.0); 2.3335 (0.9); 2.3011 (0.6); 2.2664 (0.5); 2.1794 (0.7); 2.1425 (16.0); 2.0917 (1.1); 2.0426 (0.9); 2.0180 (0.5); 2,0006 (0.4); 1.9818 (0.4); 1.4731 (8.8); 1.4550 (8.8); 1.3622 (0.5); 1.3429 (0.9); 1.3040 (0.7); 1.2423 (6.8); 0.8598 (0.9); 0.8428 (0.5) 1-454: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 12.1712 (2.6); 8.6262 (9.8); 7.2365 (0.7); 7.2150 (1.5); 7.1883 (1.6); 7.1668 (0.8); 7.1306 (1.0); 7.1102 (1.2); 7.1054 (1.2); 7.1004 (1.1); 7.0847 (1.0); 7.0806 (0.9); 6.9688 (1.4); 3.9600 (0.6); 3.9420 (1.7); 3.9239 (1.8); 3.9058 (0.7); 3.3165 (13.6); 3.2890 (0.5); 2.6756 (0.3); 2.5067 (49.3); 2.3336 (0.5); 2.1358 (16.0); 2.0911 (0.4); 2.0507 (0.4); 1.9937 (0.6); 1.4148 (7.8); 1.3966 (7.9); 1.2407 (0.9); 1.1804 (0.3) 1-455: 1H-NMR(400.1 MHz, d6-DMSO): δ = 12.1712 (2.6); 8.6262 (9.8); 7.2365 (0.7); 7.2150 (1.5); 7.1883 (1.6); 7.1668 (0.8); 7.1306 (1.0); 7.1102 (1.2); 7.1054 (1.2); 7.1004 (1.1); 7.0847 (1.0); 7.0806 (0.9); 6.9688 (1.4); 3.9600 (0.6); 3.9420 (1.7); 3.9239 (1.8); 3.9058 (0.7); 3.3165 (13.6); 3.2890 (0.5); 2.6756 (0.3); 2.5067 (49.3); 2.3336 (0.5); 2.1358 (16.0); 2.0911 (0.4); 2.0507 (0.4); 1.9937 (0.6); 1.4148 (7.8); 1.3966 (7.9); 1.2407 (0.9); 1.1804 (0.3) 1-455: 1H-NMR (400.1 MHz, d6-DMSO):
δ= 12.1057 (2.5); 8.6121 (9.8); 7.1908 (1.3); 7.1716 (4.0); 7.1539 (6.4); 7.1449 (7.2); 7.1284 (2.5); 7.1005 (1.5); 7.0836 (2.0); 7.0720 (0.8); 7.0668 (0.9); 3.9137 (0.6); 3.8957 (1.9); 3.8774 (1.9); 3.8592 (0.7); 3.3475 (0.4); 3.3443 (0.6); 3.3412 (0.7); 3.3213 (39.0); 3.2984 (1.0); 3.2950 (0.8); 3.2918 (0.7); 3.2853 (0.4); 2.6759 (0.4); 2.5071 (69.2); 2.3337 (0.5); 2.0942 (16.0); 1.4222δ = 12.1057 (2.5); 8.6121 (9.8); 7.1908 (1.3); 7.1716 (4.0); 7.1539 (6.4); 7.1449 (7.2); 7.1284 (2.5); 7.1005 (1.5); 7.0836 (2.0); 7.0720 (0.8); 7.0668 (0.9); 3.9137 (0.6); 3.8957 (1.9); 3.8774 (1.9); 3.8592 (0.7); 3.3475 (0.4); 3.3443 (0.6); 3.3412 (0.7); 3.3213 (39.0); 3.2984 (1.0); 3.2950 (0.8); 3.2918 (0.7); 3.2853 (0.4); 2.6759 (0.4); 2.5071 (69.2); 2.3337 (0.5); 2.0942 (16.0); 1.4222
(8.3); 1.4039 (8.4); 1.3429 (0.4); 1.2415 (2.4) (8.3); 1.4039 (8.4); 1.3429 (0.4); 1.2415 (2.4)
1-456: 1H-NMR(400.0 MHz, CDC13):  1-456: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3352 (11.2); 7.2610 (15.3); 6.8082 (0.9); 6.8064 (1.0); 6.8023 (0.9); 6.7996 (1.0); 6.7977 (1.0); 6.7940 (0.8); 6.7895 (1.0);δ = 8.3352 (11.2); 7.2610 (15.3); 6.8082 (0.9); 6.8064 (1.0); 6.8023 (0.9); 6.7996 (1.0); 6.7977 (1.0); 6.7940 (0.8); 6.7895 (1.0);
6.7857 (2.4); 6.7757 (1.0); 6.7730 (1.7); 3.8136 (16.0); 2.3463 (13.6); 2.0047 (1.3); 1.5517 (1.7); -0.0002 (8.6) 6.7857 (2.4); 6.7757 (1.0); 6.7730 (1.7); 3.8136 (16.0); 2.3463 (13.6); 2.0047 (1.3); 1.5517 (1.7); -0.0002 (8.6)
1-457: 1H-NMR(400.0 MHz, CDC13):  1-457: 1H-NMR (400.0 MHz, CDC13):
δ= 8.4596 (5.2); 8.4477 (5.3); 7.2617 (13.0); 7.0291 (1.5); 7.0172 (2.9); 7.0052 (1.4); 6.8887 (1.0); 6.8833 (1.1); 6.8689 (1.0); 6.8635 (1.2); 6.8607 (1.1); 6.8395 (1.6); 6.8333 (0.9); 6.8122 (1.6); 6.7873 (0.9); 6.7819 (0.8); 6.7764 (1.0); 6.7711 (0.9); 6.7662 (0.5); 6.7608 (0.5); 4.1673 (15.8); 3.8841 (16.0); 3.7929 (14.6); -0.0002 (7.5) δ = 8.4596 (5.2); 8.4477 (5.3); 7.2617 (13.0); 7.0291 (1.5); 7.0172 (2.9); 7.0052 (1.4); 6.8887 (1.0); 6.8833 (1.1); 6.8689 (1.0); 6.8635 (1.2); 6.8607 (1.1); 6.8395 (1.6); 6.8333 (0.9); 6.8122 (1.6); 6.7873 (0.9); 6.7819 (0.8); 6.7764 (1.0); 6.7711 (0.9); 6.7662 (0.5); 6.7608 (0.5); 4.1673 (15.8); 3.8841 (16.0); 3.7929 (14.6); -0.0002 (7.5)
1-458: 1H-NMR(400.0 MHz, CDC13):  1-458: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3407 (10.3); 7.2609 (13.7); 6.9343 (0.5); 6.8089 (0.8); 6.8035 (0.6); 6.7911 (0.5); 6.7858 (0.8); 4.1628 (16.0); 3.9072 (16.0);δ = 8.3407 (10.3); 7.2609 (13.7); 6.9343 (0.5); 6.8089 (0.8); 6.8035 (0.6); 6.7911 (0.5); 6.7858 (0.8); 4.1628 (16.0); 3.9072 (16.0);
-0.0002 (7.9) -0.0002 (7.9)
1-459: 1H-NMR(400.0 MHz, CDC13):  1-459: 1H-NMR (400.0 MHz, CDC13):
δ= 8.2854 (11.2); 7.2607 (14.2); 7.0775 (1.2); 7.0721 (0.5); 7.0639 (1.3); 7.0556 (1.5); 7.0476 (0.6); 7.0420 (1.4); 6.8365 (1.8); 6.8311 (0.6); 6.8199 (0.6); 6.8147 (3.3); 6.8093 (0.7); 6.7981 (0.5); 6.7928 (1.5); 5.0014 (0.5); 4.1474 (16.0); 3.9576 (4.2); 2.0043 (0.9); 1.9019 (0.5); 1.8867 (0.7); 1.8767 (0.8); 1.7119 (0.6); 1.7040 (0.7); 1.6892 (0.6); 1.6799 (0.5); 1.4460 (0.6); 1.4402δ = 8.2854 (11.2); 7.2607 (14.2); 7.0775 (1.2); 7.0721 (0.5); 7.0639 (1.3); 7.0556 (1.5); 7.0476 (0.6); 7.0420 (1.4); 6.8365 (1.8); 6.8311 (0.6); 6.8199 (0.6); 6.8147 (3.3); 6.8093 (0.7); 6.7981 (0.5); 6.7928 (1.5); 5.0014 (0.5); 4.1474 (16.0); 3.9576 (4.2); 2.0043 (0.9); 1.9019 (0.5); 1.8867 (0.7); 1.8767 (0.8); 1.7119 (0.6); 1.7040 (0.7); 1.6892 (0.6); 1.6799 (0.5); 1.4460 (0.6); 1.4402
(0.6); 1.4162 (1.5); 1.3954 (1.4); 1.3726 (0.5); 1.3650 (0.7); -0.0002 (8.1) (0.6); 1.4162 (1.5); 1.3954 (1.4); 1.3726 (0.5); 1.3650 (0.7); -0.0002 (8.1)
1-460: 1H-NMR(400.0 MHz, CDC13):  1-460: 1H NMR (400.0 MHz, CDC13):
δ= 8.2737 (10.8); 7.2599 (28.2); 7.1473 (1.7); 7.1421 (0.7); 7.1345 (1.8); 7.1301 (0.9); 7.1251 (2.0); 7.1176 (0.8); 7.1123 (1.9); 6.8763 (2.0); 6.8708 (0.6); 6.8594 (0.7); 6.8547 (3.3); 6.8496 (0.7); 6.8382 (0.6); 6.8328 (1.6); 5.0137 (0.7); 4.1763 (16.0); 1.8439 (0.5); 1.8309 (0.6); 1.8147 (0.6); 1.8059 (0.7); 1.7129 (0.6); 1.7048 (0.6); 1.6969 (0.6); 1.6890 (0.7); 1.6818 (0.6); 1.4843 (0.5); 1.4597 (0.6); 1.4516 (0.7); 1.4286 (0.9); 1.4018 (0.7); 1.3983 (0.7); 1.3706 (0.9); 1.3628 (0.6); 1.3463 (0.7); 1.3382 (0.8);δ = 8.2737 (10.8); 7.2599 (28.2); 7.1473 (1.7); 7.1421 (0.7); 7.1345 (1.8); 7.1301 (0.9); 7.1251 (2.0); 7.1176 (0.8); 7.1123 (1.9); 6.8763 (2.0); 6.8708 (0.6); 6.8594 (0.7); 6.8547 (3.3); 6.8496 (0.7); 6.8382 (0.6); 6.8328 (1.6); 5.0137 (0.7); 4.1763 (16.0); 1.8439 (0.5); 1.8309 (0.6); 1.8147 (0.6); 1.8059 (0.7); 1.7129 (0.6); 1.7048 (0.6); 1.6969 (0.6); 1.6890 (0.7); 1.6818 (0.6); 1.4843 (0.5); 1.4597 (0.6); 1.4516 (0.7); 1.4286 (0.9); 1.4018 (0.7); 1.3983 (0.7); 1.3706 (0.9); 1.3628 (0.6); 1.3463 (0.7); 1.3382 (0.8);
0.0080 (0.6); -0.0002 (16.0); -0.0085 (0.5) 0.0080 (0.6); -0.0002 (16.0); -0.0085 (0.5)
1-461 : lH-NMR(400.0 MHz, d6-DMSO):  1-461: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 9.3888 (2.8); 8.6067 (6.2); 7.0468 (0.6); 7.0279 (2.2); 7.0235 (1.3); 7.0069 (2.4); 6.9971 (0.5); 6.9900 (0.6); 6.8376 (0.5); 6.8353 (0.6); 6.8311 (0.5); 6.8291 (0.5); 6.7282 (2.5); 6.7231 (0.8); 6.7118 (0.7); 6.7068 (2.2); 5.0703 (3.1); 3.5123 (2.4); 3.3129 (16.0); 2.5188 (0.6); 2.5101 (6.6); 2.5056 (13.6); 2.5010 (18.5); 2.4965 (13.1); 2.4920 (6.1); 2.2069 (7.1); 1.9879 (1.0); 1.1747δ = 9.3888 (2.8); 8.6067 (6.2); 7.0468 (0.6); 7.0279 (2.2); 7.0235 (1.3); 7.0069 (2.4); 6.9971 (0.5); 6.9900 (0.6); 6.8376 (0.5); 6.8353 (0.6); 6.8311 (0.5); 6.8291 (0.5); 6.7282 (2.5); 6.7231 (0.8); 6.7118 (0.7); 6.7068 (2.2); 5.0703 (3.1); 3.5123 (2.4); 3.3129 (16.0); 2.5188 (0.6); 2.5101 (6.6); 2.5056 (13.6); 2.5010 (18.5); 2.4965 (13.1); 2.4920 (6.1); 2.2069 (7.1); 1.9879 (1.0); 1.1747
(0.6); -0.0002 (0.8) (0.6); -0.0002 (0.8)
1-462: lH-NMR(400.0 MHz, CDC13):  1-462: 1H NMR (400.0 MHz, CDC13):
δ= 7.7391 (1.6); 7.7162 (1.8); 7.2846 (1.0); 7.2619 (7.9); 6.9960 (0.7); 6.9827 (0.7); 6.7694 (0.6); 5.2984 (16.0); 3.7581 (9.1);δ = 7.7391 (1.6); 7.7162 (1.8); 7.2846 (1.0); 7.2619 (7.9); 6.9960 (0.7); 6.9827 (0.7); 6.7694 (0.6); 5.2984 (16.0); 3.7581 (9.1);
2.2023 (9.2); 1.5669 (0.6); -0.0002 (3.8) 2.2023 (9.2); 1.5669 (0.6); -0.0002 (3.8)
1-463: 1H-NMR(400.0 MHz, CDC13):  1-463: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3257 (13.0); 7.2603 (24.9); 7.1238 (0.5); 7.1086 (0.6); 7.1041 (1.1); 7.0889 (1.1); 7.0844 (0.8); 7.0692 (0.7); 6.8524 (1.1); 6.8509 (1.1); 6.8334 (1.0); 6.8318 (1.0); 6.7744 (0.7); 6.7688 (0.9); 6.7470 (1.2); 6.7259 (0.6); 6.7219 (0.8); 3.6139 (16.0);δ = 8.3257 (13.0); 7.2603 (24.9); 7.1238 (0.5); 7.1086 (0.6); 7.1041 (1.1); 7.0889 (1.1); 7.0844 (0.8); 7.0692 (0.7); 6.8524 (1.1); 6.8509 (1.1); 6.8334 (1.0); 6.8318 (1.0); 6.7744 (0.7); 6.7688 (0.9); 6.7470 (1.2); 6.7259 (0.6); 6.7219 (0.8); 3.6139 (16.0);
3.6057 (6.5); 2.1592 (15.2); 1.5732 (0.9); -0.0002 (14.2); -0.0085 (0.5) 3.6057 (6.5); 2.1592 (15.2); 1.5732 (0.9); -0.0002 (14.2); -0.0085 (0.5)
1-464: 1H-NMR(400.0 MHz, CDC13):  1-464: 1H-NMR (400.0 MHz, CDC13):
δ= 7.7435 (3.1); 7.7208 (3.4); 7.2715 (3.3); 7.2598 (52.4); 7.2487 (3.3); 7.0126 (0.6); 6.9994 (0.6); 6.9895 (1.2); 6.9762 (1.2); 6.9665 (0.7); 6.9533 (0.7); 6.8200 (0.6); 6.8126 (0.7); 6.7994 (0.6); 6.7924 (1.1); 6.7858 (0.7); 6.7725 (0.6); 6.7651 (0.7); 6.7108 (0.5); 6.6960 (0.5); 6.6922 (0.7); 6.6884 (0.8); 6.6848 (0.6); 5.2983 (0.6); 3.7627 (15.9); 2.1975 (16.0); 1.5366 (11.4); 0.0079δ = 7.7435 (3.1); 7.7208 (3.4); 7.2715 (3.3); 7.2598 (52.4); 7.2487 (3.3); 7.0126 (0.6); 6.9994 (0.6); 6.9895 (1.2); 6.9762 (1.2); 6.9665 (0.7); 6.9533 (0.7); 6.8200 (0.6); 6.8126 (0.7); 6.7994 (0.6); 6.7924 (1.1); 6.7858 (0.7); 6.7725 (0.6); 6.7651 (0.7); 6.7108 (0.5); 6.6960 (0.5); 6.6922 (0.7); 6.6884 (0.8); 6.6848 (0.6); 5.2983 (0.6); 3.7627 (15.9); 2.1975 (16.0); 1.5366 (11.4); 0.0079
(0.9); -0.0002 (29.0); -0.0085 (1.2) (0.9); -0.0002 (29.0); -0.0085 (1.2)
1-465: 1H-NMR(400.0 MHz, CDC13):  1-465: 1H-NMR (400.0 MHz, CDC13):
δ= 7.4203 (2.8); 7.3975 (3.3); 7.2608 (19.2); 7.1262 (3.3); 7.1034 (2.8); 7.0320 (0.6); 7.0186 (0.6); 7.0088 (1.2); 6.9955 (1.2); 6.9857 (0.7); 6.9723 (0.6); 6.8184 (0.6); 6.8110 (0.7); 6.7977 (0.6); 6.7909 (1.0); 6.7841 (0.7); 6.7708 (0.6); 6.7634 (0.6); 6.6898δ = 7.4203 (2.8); 7.3975 (3.3); 7.2608 (19.2); 7.1262 (3.3); 7.1034 (2.8); 7.0320 (0.6); 7.0186 (0.6); 7.0088 (1.2); 6.9955 (1.2); 6.9857 (0.7); 6.9723 (0.6); 6.8184 (0.6); 6.8110 (0.7); 6.7977 (0.6); 6.7909 (1.0); 6.7841 (0.7); 6.7708 (0.6); 6.7634 (0.6); 6.6898
(0.7); 6.6862 (0.8); 6.6825 (0.6); 5.2983 (1.1); 3.7449 (16.0); 2.1783 (15.3); 1.5539 (5.5); -0.0002 (10.1) (0.7); 6.6862 (0.8); 6.6825 (0.6); 5.2983 (1.1); 3.7449 (16.0); 2.1783 (15.3); 1.5539 (5.5); -0.0002 (10.1)
1-466: lH-NMR(400.0 MHz, d6-DMSO):  1-466: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 8.7158 (13.8); 7.1183 (0.7); 7.0971 (0.6); 7.0914 (1.8); 7.0854 (0.6); 7.0743 (0.8); 7.0685 (2.8); 7.0646 (0.8); 7.0535 (0.7); 7.0473 (2.4); 6.9210 (2.6); 6.9130 (1.1); 6.9100 (2.7); 6.9039 (1.4); 6.9008 (0.9); 6.8979 (1.9); 6.8929 (0.8); 6.8870 (1.8); 5.7522 (4.2); 4.1638 (1.2); 4.1460 (4.3); 4.1283 (5.0); 4.1106 (2.2); 4.0546 (16.0); 3.9481 (4.0); 3.8259 (4.3); 3.4990 (1.3); 2.5239 (0.6); 2.5192 (0.8); 2.5105 (10.5); 2.5060 (21.9); 2.5014 (30.0); 2.4968 (21.2); 2.4923 (9.9); 0.9948 (4.4); 0.9771 (9.4); 0.9593 (4.2); -δ = 8.7158 (13.8); 7.1183 (0.7); 7.0971 (0.6); 7.0914 (1.8); 7.0854 (0.6); 7.0743 (0.8); 7.0685 (2.8); 7.0646 (0.8); 7.0535 (0.7); 7.0473 (2.4); 6.9210 (2.6); 6.9130 (1.1); 6.9100 (2.7); 6.9039 (1.4); 6.9008 (0.9); 6.8979 (1.9); 6.8929 (0.8); 6.8870 (1.8); 5.7522 (4.2); 4.1638 (1.2); 4.1460 (4.3); 4.1283 (5.0); 4.1106 (2.2); 4.0546 (16.0); 3.9481 (4.0); 3.8259 (4.3); 3.4990 (1.3); 2.5239 (0.6); 2.5192 (0.8); 2.5105 (10.5); 2.5060 (21.9); 2.5014 (30.0); 2.4968 (21.2); 2.4923 (9.9); 0.9948 (4.4); 0.9771 (9.4); 0.9593 (4.2); -
0.0002 (4.1) 0.0002 (4.1)
1-467: 1H-NMR(400.0 MHz, CDC13):  1-467: 1H-NMR (400.0 MHz, CDC13):
δ= 8.3578 (1.3); 8.3500 (4.0); 7.2601 (44.8); 6.9805 (0.7); 6.9672 (0.7); 6.9575 (1.4); 6.9442 (1.4); 6.9345 (0.8); 6.9212 (0.8); 6.8214 (0.8); 6.8140 (0.9); 6.8006 (0.9); 6.7938 (1.4); 6.7871 (1.0); 6.7738 (0.8); 6.7664 (0.9); 6.7127 (0.6); 6.7082 (0.6); 6.7053 (0.6); 6.7008 (0.5); 6.6932 (0.7); 6.6889 (0.9); 6.6856 (1.0); 6.6818 (0.8); 6.6780 (0.5); 6.6705 (0.5); 6.6659 (0.6); 5.2981 (1.0); 3.8966 (0.6); 3.6676 (0.6); 2.5008 (0.8); 2.2491 (16.0); 2.1351 (0.6); 2.0444 (0.5); 1.2588 (1.0); 0.0080 (0.8); -0.0002 (25.6); - 0.0085 (0.9) NMR-Daten ausgewählter Intermediate (Peakliste) δ = 8.3578 (1.3); 8.3500 (4.0); 7.2601 (44.8); 6.9805 (0.7); 6.9672 (0.7); 6.9575 (1.4); 6.9442 (1.4); 6.9345 (0.8); 6.9212 (0.8); 6.8214 (0.8); 6.8140 (0.9); 6.8006 (0.9); 6.7938 (1.4); 6.7871 (1.0); 6.7738 (0.8); 6.7664 (0.9); 6.7127 (0.6); 6.7082 (0.6); 6.7053 (0.6); 6.7008 (0.5); 6.6932 (0.7); 6.6889 (0.9); 6.6856 (1.0); 6.6818 (0.8); 6.6780 (0.5); 6.6705 (0.5); 6.6659 (0.6); 5.2981 (1.0); 3.8966 (0.6); 3.6676 (0.6); 2,5008 (0.8); 2.2491 (16.0); 2.1351 (0.6); 2.0444 (0.5); 1.2588 (1.0); 0.0080 (0.8); -0.0002 (25.6); - 0.0085 (0.9) NMR data of selected intermediates (peak list)
NMR-Daten ausgewählter Intermediate (manuelle Auswertung) Beispielnummer NMR data of selected intermediates (manual evaluation) example number
A-07 'H-NMR (400 MHz, CDC13): δ = 8.26 (s, 2H), 5.81 (s, 1H), 3.87 (s, 3H), 3.72 (s, 3H), 2.28 (s, 3H) A-07 'H-NMR (400 MHz, CDC1 3 ): δ = 8.26 (s, 2H), 5.81 (s, 1H), 3.87 (s, 3H), 3.72 (s, 3H), 2.28 (s, 3H )
A-l l 'H-NMR (400 MHz, CDCI3): δ = 8.46 (d, 1H), 7.93 (dd, 1H), 7.13 (d, 1H), 3.83 (s, 3H), 2.33 (s, 3H)  A-1 'H-NMR (400 MHz, CDCl3): δ = 8.46 (d, 1H), 7.93 (dd, 1H), 7.13 (d, 1H), 3.83 (s, 3H), 2.33 (s, 3H)
A-12 'H-NMR (400 MHz, CDCI3): δ = 8.83 (s, 2H), 3.84 (s, 3H), 2.35 (s, 3H)  A-12'-H NMR (400 MHz, CDCl 3): δ = 8.83 (s, 2H), 3.84 (s, 3H), 2.35 (s, 3H)
A-13 'H-NMR (400 MHz, CDCI3): δ = 8.25 (s, 2H), 3.88 (s, 3H), 3.82 (s, 3H), 2.32 (s, 3H) A-13 'H NMR (400 MHz, CDCl3): δ = 8.25 (s, 2H), 3.88 (s, 3H), 3.82 (s, 3H), 2.32 (s, 3H)
A-34 'H-NMR (400 MHz, CDCI3): δ = 7.26-7.14 (m, 5H), 3.88 (s, 3H), 3.64 (s, 2H), 3.62 (s, 3H), 2.06 (s, 3H) A-34 'H NMR (400 MHz, CDCl3): δ = 7.26-7.14 (m, 5H), 3.88 (s, 3H), 3.64 (s, 2H), 3.62 (s, 3H), 2.06 (s, 3H)
A-35 'H-NMR (400 MHz, CDCI3): δ = 7.29-7.24 (m, 2H), 7.01-6.92 (m, 3H), 3.87 (s, 3H), 3.64 (s, 3H), 2.07 (s, 3H)  A-35 'H NMR (400 MHz, CDCl3): δ = 7.29-7.24 (m, 2H), 7.01-6.92 (m, 3H), 3.87 (s, 3H), 3.64 (s, 3H), 2.07 ( s, 3H)
A-36 'H-NMR (400 MHz, CDCI3): δ = 7.30-7.26 (m, 2H), 7.01-6.98 (m, 3H), 3.57 (s, 3H), 2.07 (s, 3H)  A-36 'H NMR (400 MHz, CDCl3): δ = 7.30-7.26 (m, 2H), 7.01-6.98 (m, 3H), 3.57 (s, 3H), 2.07 (s, 3H)
A-37 'H-NMR (400 MHz, de-DMSO): δ = 7.28-7.24 (m, 1H), 7.04-7.00 (m, 1H), 6.84-6.78 (m, 1H), 3.60 (s, 3H), 2.17 (s, 3H)  A-37 'H-NMR (400 MHz, de-DMSO): δ = 7.28-7.24 (m, 1H), 7.04-7.00 (m, 1H), 6.84-6.78 (m, 1H), 3.60 (s, 3H 2.17 (s, 3H)
A-38 'H-NMR (400 MHz, de-DMSO): δ = 7.49-7.46 (m, 2H), 7.31-7.29 (m, 2H), 3.62 (s, 3H), 2.17 (s, 3H)  A-38 'H-NMR (400 MHz, de-DMSO): δ = 7.49-7.46 (m, 2H), 7.31-7.29 (m, 2H), 3.62 (s, 3H), 2.17 (s, 3H)
A-39 'H-NMR (400 MHz, de-DMSO): δ = 7.28-7.26 (m, 1H), 7.16-7.14 (m, 1H), 7.00-6.95 (m, 2H), 3.62 (s, 3H), 2.16 (s, 3H)  A-39 'H NMR (400 MHz, de-DMSO): δ = 7.28-7.26 (m, 1H), 7.16-7.14 (m, 1H), 7.00-6.95 (m, 2H), 3.62 (s, 3H 2.16 (s, 3H)
A-40 'H-NMR (400 MHz, de-DMSO): δ = 7.42-7.38 (m, 1H), 7.09-7.05 (m, 1H), 6.91-6.87 (m, 1H), 3.67 (s, 3H), 2.23 (s, 3H)  A-40 'H-NMR (400 MHz, de-DMSO): δ = 7.42-7.38 (m, 1H), 7.09-7.05 (m, 1H), 6.91-6.87 (m, 1H), 3.67 (s, 3H 2.23 (s, 3H)
A-41 'H-NMR (400 MHz, CDCI3): δ = 7.26-6.99 (m, 5H), 3.83 (s, 3H), 1.64-1.60 (m, 1H), 0.99- 0.95 (m, 4H)  A41 'H-NMR (400 MHz, CDCl3): δ = 7.26-6.99 (m, 5H), 3.83 (s, 3H), 1.64-1.60 (m, 1H), 0.99-0.95 (m, 4H)
A-42 'H-NMR (400 MHz, de-DMSO): δ = 7.29-7.25 (m, 1H), 7.14 (d, 1H), 6.96-6.92 (m, 2H), 3.71 (s, 3H), 1.79-1.75 (m, 1H), 0.91-0.86 (m, 2H), 0.81-0.77 (m, 2H)  A-42 'H-NMR (400 MHz, de-DMSO): δ = 7.29-7.25 (m, 1H), 7.14 (d, 1H), 6.96-6.92 (m, 2H), 3.71 (s, 3H), 1.79-1.75 (m, 1H), 0.91-0.86 (m, 2H), 0.81-0.77 (m, 2H)
A-43 'H-NMR (400 MHz, de-DMSO): δ = 7.37-7.30 (m, 1H), 7.01-6.96 (m, 1H), 6.81-6.78 (m, 2H), 3.70 (s, 3H), 1.79-1.74 (m, 1H), 0.91-0.86 (m, 2H), 0.81-0.78 (m, 2H)  A-43 'H-NMR (400 MHz, de-DMSO): δ = 7.37-7.30 (m, 1H), 7.01-6.96 (m, 1H), 6.81-6.78 (m, 2H), 3.70 (s, 3H ), 1.79-1.74 (m, 1H), 0.91-0.86 (m, 2H), 0.81-0.78 (m, 2H)
A-44 'H-NMR (400 MHz, CDCI3): δ = 7.32-7.30 (m, 3H), 7.20-7.19 (m, 1H), 3.92 (s, 3H), 3.73 (s, 3H), 2.23 (s, 3H)  A-44 'H-NMR (400 MHz, CDCl3): δ = 7.32-7.30 (m, 3H), 7.20-7.19 (m, 1H), 3.92 (s, 3H), 3.73 (s, 3H), 2.23 ( s, 3H)
A-45 'H-NMR (400 MHz, CDCI3): δ = 7.01-6.99 (m, 1H), 6.85-6.79 (m, 2H), 3.92 (s, 3H), 3.72 (s, 3H), 2.22 (s, 3H)  A-45 'H-NMR (400 MHz, CDCl3): δ = 7.01-6.99 (m, 1H), 6.85-6.79 (m, 2H), 3.92 (s, 3H), 3.72 (s, 3H), 2.22 ( s, 3H)
A-46 'H-NMR (400 MHz, CDCI3): δ = 7.14-7.10 (m, 1H), 7.05-7.02 (m, 1H), 6.99-6.93 (m, 2H), 3.92 (s, 3H), 3.72 (s, 3H), 2.22 (s, 3H)  A-46'H NMR (400 MHz, CDCl3): δ = 7.14-7.10 (m, 1H), 7.05-7.02 (m, 1H), 6.99-6.93 (m, 2H), 3.92 (s, 3H), 3.72 (s, 3H), 2.22 (s, 3H)
A-47 'H-NMR (400 MHz, CDCI3): δ = 6.89-6.86 (m, 1H), 6.79-6.73 (m, 2H), 3.92 (s, 3H), 3.70 (s, 3H), 2.24 (s, 3H)  A-47'-H NMR (400 MHz, CDCl 3): δ = 6.89-6.86 (m, 1H), 6.79-6.73 (m, 2H), 3.92 (s, 3H), 3.70 (s, 3H), 2.24 ( s, 3H)
A-48 'H-NMR (400 MHz, CDCI3): δ = 7.21-7.18 (m, 2H), 7.08-7.03 (m, 3H), 3.90 (s, 3H), 3.82 (s, 3H), 1.61 (quintet, 1H), 0.92 (d, 4H)  A-48 'H NMR (400 MHz, CDCl 3): δ = 7.21-7.18 (m, 2H), 7.08-7.03 (m, 3H), 3.90 (s, 3H), 3.82 (s, 3H), 1.61 ( quintet, 1H), 0.92 (d, 4H)
A-49 'H-NMR (400 MHz, de-DMSO): δ = 8.83 (s, 2H), 4.07 (s, 3H), 3.88 (s, 3H)  A-49 'H-NMR (400 MHz, de-DMSO): δ = 8.83 (s, 2H), 4.07 (s, 3H), 3.88 (s, 3H)
Gegenstand der vorliegenden Erfindung ist weiterhin die Verwendung einer oder mehrerer The present invention furthermore relates to the use of one or more
Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-001) bis (1-240) und/oder deren Salze, jeweils wie oben definiert, als Herbizid und/oder Pflanzenwachstumsregulator, vorzugsweise in Kulturen von Nutz- und/oder Zierpflanzen. Gegenstand der vorliegenden Erfindung ist ferner ein Verfahren zur Bekämpfung von Schadpflanzen und/oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-001) bis (1-240) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, Compounds of general formula (I) and / or their salts, as defined above, preferably in one of the preferred embodiment or particularly preferred embodiment, in particular one or more compounds of the formulas (1-001) to (1-240) and / or salts thereof, each as defined above, as a herbicide and / or plant growth regulator, preferably in crops of commercial and / or ornamental plants. The present invention furthermore relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one the embodiment characterized as being preferred or particularly preferred, in particular one or more compounds of the formulas (1-001) to (1-240) and / or salts thereof, each as defined above, or of an agent according to the invention, as defined below,
auf die (Schad)Pflanzen, (Schad)Pflanzensamen, den Boden, in dem oder auf dem die  on the (harmful) plants, (harmful) plant seeds, the soil, in or on the
(Schad)Pflanzen wachsen, oder die Anbaufläche appliziert wird.  (Schad) plants grow, or the acreage is applied.
Gegenstand der vorliegenden Erfindung ist auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen, vorzugsweise in Nutzpflanzenkulturen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichnetenThe present invention also provides a process for controlling undesirable plants, preferably in crops, characterized in that an effective amount of one or more compounds of general formula (I) and / or salts thereof, as defined above, preferably in one of preferred or particularly preferred marked
Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-001) bis (1-240) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, Embodiment, in particular one or more compounds of the formulas (1-001) to (1-240) and / or salts thereof, each as defined above, or an agent according to the invention, as defined below,
auf unerwünschte Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut der unerwünschten Pflanzen (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die unerwünschte Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die unerwünschte Pflanzen wachsen werden) appliziert wird.  undesirable plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesirable crops), the seed of the unwanted plants (ie plant seeds, eg grains, seeds or vegetative propagules such as tubers or sprouts with buds), the soil in which or on which unwanted plants grow (eg the soil of cultivated land or non-cultivated land) or the cultivated area (ie area on which the unwanted plants will grow) is applied.
Gegenstand der vorliegenden Erfindung ist ferner auch Verfahren zur Bekämpfung zur The present invention is also a method for controlling
Wachstumsregulierung von Pflanzen, vorzugsweise von Nutzpflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-001) bis (1-240) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, Growth regulation of plants, preferably of useful plants, characterized in that an effective amount of one or more compounds of general formula (I) and / or their salts, as defined above, preferably in one of the preferred or particularly preferred Embodiment, in particular one or more compounds of the formulas (1-001) to (1-240) and / or salts thereof, each as defined above, or an agent according to the invention, as defined below,
die Pflanze, das Saatgut der Pflanze (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative the plant, the seed of the plant (i.e., plant seeds, e.g., grains, seeds or vegetative
Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die Pflanzen wachsen werden) appliziert wird. Dabei können die erfindungsgemäßen Verbindungen bzw. die erfindungsgemäßen Mittel z.B. im Vorsaat- (gegebenenfalls auch durch Einarbeitung in den Boden), Vorauflauf- und/oder Propagating organs such as tubers or sprouts with buds), the soil in which or on which the plants grow (e.g., the soil of cultivated land or non-cultivated land) or the cultivated area (i.e., area on which the plants will grow) is applied. The compounds according to the invention or the agents according to the invention may e.g. in Vorsaat- (possibly also by incorporation into the soil), pre-emergence and / or
Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Postemergence be applied. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora may be mentioned, which can be controlled by the compounds according to the invention, without the intention of being restricted to certain species.
Vorzugsweise werden in einem erfindungsgemäßen Verfahren zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung in Kulturen von Nutzpflanzen oder Zierpflanzen eingesetzt, wobei die Nutzpflanzen oder Zierpflanzen in einer bevorzugten Ausgestaltung transgene Pflanzen sind. Preferably, in a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I) and / or their salts are employed for controlling harmful plants or regulating growth in crops of crops or ornamental plants, the crops or ornamentals in a preferred embodiment are transgenic plants.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze eignen sich zur Bekämpfung der folgenden Gattungen von monokotylen und dikotylen Schadpflanzen: The compounds of the general formula (I) according to the invention and / or salts thereof are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants:
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Dikotyle Schadpflanzen der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Werden die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) vor dem Keimen der Schadpflanzen (Ungräser und/oder Unkräuter) auf die Erdoberfläche appliziert (VorauflaufVerfahren), so wird entweder das Auflaufen der Ungras- bzw. Unkrautkeimlinge vollständig verhindert oder diese wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab. Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ishumum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis Galinsoga Galium Hibiscus Ipomoea Kochia Lamium Lepidium Lindernia Matricaria Mentha Mercurialis Mullugo Myosotis Papaver Pharbitis Plantago Polygonum Portulaca Ranunculus Raphanus Rorippa Rotala Rumex , Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. If the compounds of the general formula (I) according to the invention are applied to the surface of the earth (grass weeds and / or weeds) (pre-emergence method), either the emergence of weed seedlings or weed seedlings is completely prevented or they grow up to the cotyledon stage stage but then they stop growing and eventually die off after three to four weeks.
Bei Applikation der Wirkstoffe der allgemeinen Formel (I) auf die grünen Pflanzenteile im When applying the active compounds of the general formula (I) to the green plant parts in
Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Postemergence treatment occurs after the treatment growth arrest and the harmful plants remain in the stage of growth existing at the time of application or die completely after a certain time, so that in this way harmful to the crops
Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. Weed competition is eliminated very early and sustainably.
Obgleich die erfindungsgemäßen Verbindungen der allgemeinnen Formel (I) eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Although the compounds of general formula (I) according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops are e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,
Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, abhängig von der Struktur der jeweiligen erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotylic cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, depending on the structure of the respective compound of the invention and its 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 plants.
Darüberhinaus weisen die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) (abhängig von ihrer jeweiligen Struktur und der ausgebrachten Aufwandmenge) hervorragende Moreover, the compounds of the general formula (I) according to the invention (depending on their respective structure and the applied application rate) are excellent
wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von growth regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to influence the metabolism
Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativem Wachstum, ohne dabei die Pflanzen abzutöten. EinePhytochemicals and to facilitate harvesting, e.g. be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. A
Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, as, for example, storage formation can be reduced or completely prevented.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe der allgemeinen Formel (I) auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Due to their herbicidal and plant growth regulatory properties, the active compounds of the general formula (I) can also be used for controlling harmful plants in crops of genetically modified or by conventional mutagenesis modified plants. The transgenic plants are usually distinguished 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. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Preferred for transgenic cultures is the use of the compounds of general formula (I) according to the invention and / or their salts 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, soya, rapeseed, potato, tomato, pea and other vegetables.
Vorzugsweise können die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) auch als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Preferably, the compounds of the general formula (I) according to the invention can also be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gentechnisch veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten On account of their herbicidal and plant growth-regulating properties, the compounds of the general formula (I) according to the invention can also be employed for controlling harmful plants in crops of known or yet to be developed genetically modified plants. The transgenic plants are usually characterized by particular advantageous properties, for example, by resistance to certain pesticides, especially certain
Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, 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 e.g. the crop in terms of quantity, quality, shelf life,
Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Weitere besondere Eigenschaften können in einer Toleranz oder Resistenz gegen abiotische Stressoren z.B. Hitze, Kälte, Trockenheit, Salz und ultraviolette Strahlung liegen.  Composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known. Other particular properties may include tolerance or resistance to abiotic stressors, e.g. Heat, cold, drought, salt and ultraviolet radiation are present.
Bevorzugt ist die Anwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Triticale, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Vorzugsweise können die Verbindungen der allgemeinen Formel (I) als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Preference is given to the use of the compounds of general formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, triticale, millet, rice, manioc and corn or also Cultures of sugar beet, cotton, soy, rapeseed, potato, tomato, pea and other vegetables. Preferably, the compounds of general formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant. Conventional ways of producing new plants which have modified properties in comparison with previously occurring plants consist, for example, in classical methods
Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden. Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit verändertenBreeding methods and the generation of mutants. Alternatively, new plants with altered properties can be generated using genetic engineering techniques. Numerous molecular biology techniques used to transform new transgenic plants
Eigenschaften hergestellt werden können, sind dem Fachmann bekannt. Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z.B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden. Properties can be produced, are known in the art. For such genetic engineering, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. By means of standard methods, e.g. Base exchanges are made, partial sequences removed or natural or synthetic sequences added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments.
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. The production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA- Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA- Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. For this purpose, on the one hand DNA molecules can be used which comprise the entire coding sequence of a gene product including any flanking sequences, as well as DNA molecules which comprise only parts of the coding sequence, which parts have to be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z.B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 11 (1992), 3219- 3227). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden. Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. However, to achieve localization in a particular compartment, for example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells. The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants can in principle be plants of any one
Pflanzenspezies handeln, d.h. sowohl monokotyle als auch dikotyle Pflanzen. Plant species, i. both monocotyledonous and dicotyledonous plants.
So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Vorzugsweise können die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z.B. Dicamba oder gegen Herbizide, die essentielle Pflanzenenzyme, z.B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydoxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. Thus, transgenic plants are available which have altered properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences. Preferably, the compounds of general formula (I) according to the invention can be used in transgenic cultures which are resistant to growth factors, such as e.g. Dicamba or against herbicides containing essential plant enzymes, e.g. Acetylactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), respectively, which are resistant to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogues.
Bei der Anwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze als Herbizide zur Bekämpfung von Schadpflanzen in Kulturen von Nutz- oder Zierpflanzen, gegebenenfalls in transgenen Kulturpflanzen. In the application of the compounds of the general formula (I) according to the invention in transgenic crops, in addition to the effects observed in other crops against 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, that can be combated, changed application rates, which can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crops. The invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.
Bevorzugt ist die Verwendung von Verbindungen der allgemeinen Formel (I) in Getreide, dabei vorzugsweise Mais, Weizen, Gerste, Roggen, Hafer, Hirse, oder Reis, im Vor- oder Nachauflauf. Preference is given to the use of compounds of general formula (I) in cereals, preferably corn, wheat, barley, rye, oats, millet, or rice, in the pre-or post-emergence.
Bevorzugt ist auch die Verwendung von Verbindungen der allgemeinene Formel (I) in Soja im Voroder Nachauflauf. Also preferred is the use of compounds of general formula (I) in soy in the pre or postemergence.
Die Verwendung erfindungsgemäßer Verbindungen der Formel (I) zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen schließt auch den Fall ein, bei dem einer Verbindung der allgemeinen Formel (I) oder deren Salz erst nach der Ausbringung auf der Pflanze, in der Pflanze oder im Boden aus einer Vorläufersubstanz ("Prodrug") gebildet wird. The use of compounds of the formula (I) according to the invention for controlling harmful plants or regulating the growth of plants also includes the case in which a compound of the of general formula (I) or its salt is formed only after application to the plant, in the plant or in the soil from a precursor substance ("prodrug").
Gegenstand der Erfindung ist auch die Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) oder deren Salzen bzw. eines erfindungsgemäßen Mittels (wie nachstehend definiert) (in einem Verfahren) zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass man eine wirksame Menge einer oder mehreren Verbindungen der allgemeinen Formel (I) oder deren Salzen auf die Pflanzen (Schadpflanzen, gegebenenfalls zusammen mit den Nutzpflanzen) Pflanzensamen, den Boden, in dem oder auf dem die Pflanzen wachsen, oder die Anbaufläche appliziert. The invention also provides the use of one or more compounds of the general formula (I) or salts thereof or an agent according to the invention (as defined below) (in a process) for controlling harmful plants or regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or salts thereof on the plants (harmful plants, optionally together with the useful plants) plant seeds, the soil in which or on which the plants grow, or the cultivated area.
Gegenstand der Erfindung ist auch ein herbizides und/oder pfianzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, dass das Mittel (a) eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthält wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten The invention also provides a herbicidal and / or plant growth-regulating agent, characterized in that the agent (a) contains one or more compounds of the general formula (I) and / or salts thereof as defined above, preferably in one of the preferred or particularly preferably marked
Ausgestaltung, insbesondere eine oder mehrere Verbindungen der Formeln Embodiment, in particular one or more compounds of the formulas
(1-001) bis (1-240) und/oder deren Salze, jeweils wie oben definiert, (1-001) to (1-240) and / or salts thereof, each as defined above,
und and
(b) ein oder mehrere weitere Stoffe ausgewählt aus den Gruppen (i) und/oder (ii): (b) one or more further substances selected from groups (i) and / or (ii):
(i) ein oder mehrere weitere agrochemisch wirksame Stoffe, vorzugsweise ausgewählt aus der Gruppe bestehend aus Insektiziden, Akariziden, Nematiziden, weiteren Herbiziden (d.h. solche, die nicht der oben definierten allgemeinen Formel (I) entsprechen), Fungiziden, Safenern,(i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e., those which do not correspond to the general formula (I) defined above), fungicides, safeners,
Düngemitteln und/oder weiteren Wachstumsregulatoren, Fertilizers and / or other growth regulators,
(ii) ein oder mehrere im Pflanzenschutz übliche Formulierungshilfsmittel. Die weiteren agrochemischen wirksamen Stoffe des Bestandteils (i) eines erfindungsgemäßen Mittels sind dabei vorzugsweise ausgewählt aus der Gruppe der Stoffe, die in "The Pesticide Manual", 16th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2012 genannt sind. (ii) one or more formulation aids customary in crop protection. The other agrochemically active substances of constituent (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 are mentioned.
Ein erfindungsgemäßes herbizides oder pfianzenwachstumsregulierendes Mittel, umfasst vorzugsweise ein, zwei, drei oder mehr im Pflanzenschutz übliche Formulierungshilfsmittel (ii) ausgewählt aus der Gruppe bestehend aus Tensiden, Emulgatoren, Dispergiermitteln, Filmbildnern, Verdickungsmitteln, anorganischen Salzen, Stäubemitteln, bei 25 °C und 1013 mbar festen Trägerstoffen, vorzugsweise adsorptionsfähigen, granulierten Inertmaterialien, Netzmitteln, Antioxidationsmitteln, Stabilisatoren, Puffersubstanzen, Antischaummitteln, Wasser, organischen Lösungsmitteln, vorzugsweise bei 25 °C und 1013 mbar mit Wasser in jedem beliebigen Verhältnis mischbare organische Lösungsmittel. Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können in Form von Spritzpulvern, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, die Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthalten. A herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more plant protection formulation auxiliaries (ii) selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably at 25 ° C and 1013 mbar with water in any ratio miscible organic solvents. The compounds of the general formula (I) 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 compounds of the general formula (I) and / or salts thereof.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: The compounds of the general formula (I) according to the invention and / or their salts can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. As formulation options are for example in question:
Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in- Wasser- und Wasser-in-Öl-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Wettable powders (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), dispersions Oil or water based, oil miscible solutions,
Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Capsule suspensions (CS), dusts (DP), mordants, granules for the scattering and
Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
Mikrokapseln und Wachse. Microcapsules and waxes.
Diese einzelnen Formulierungstypen und die Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind dem Fachmann bekannt, und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive These individual types of formulation and formulation aids such as inert materials, surfactants, solvents and other additives are known to those skilled in the art and are described, for example, in Watkins, Handbook of Insecticides Dust Diluents and Carriers, 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive
Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Äthylenoxidaddukte ", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler," Chemical Technology ", Volume 7, C. Hanser Verlag Munich, 4th ed., 1986.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calcium-Salze wie Dispersants), for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, dibutylnaphthalene-sodium sulfonate or sodium oleoylmethyltaurine. To produce the spray powders are the herbicidal active ingredients finely ground, for example, in conventional equipment such as hammer mills, fan 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 such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). As emulsifiers can be used for example: Alkylarylsulfonsaure calcium salts such as
Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol ester,
Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or
Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester. Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Polyoxethylenesorbitanester such. Polyoxyethylene. Dusts are obtained by milling the active ingredient with finely divided solids, e.g.
Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden. Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
Emulsionen, z.B. Öl-in- Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Emulsions, e.g. Oil-in-water emulsions (EW), for example, by means of stirrers,
Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Colloidal mills and / or static mixers using aqueous organic
Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen. Solvents and optionally surfactants, such as e.g. listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. Also suitable
Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden.  Active ingredients in the usual manner for the production of fertilizer granules - if desired, mixed with fertilizers - granulated.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt. Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulaten siehe z.B. Verfahren in "Spray- Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. 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. For the preparation of plate, fluidized bed, extruder and spray granules, see, for example, the procedure in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff .; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103. For further details on the formulation of crop protection agents see, e.g. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
Die agrochemischen Zubereitungen, vorzugsweise herbizide oder pflanzenwachstumsregulierende Mittel der vorliegenden Erfindung enthalten vorzugsweise eine Gesamtmenge von 0,1 bis 99 Gew.-%, bevorzugt 0,5 bis 95 Gew.- %, weiter bevorzugt 1 bis 90 Gew.- %, insbesondere bevorzugt 2 bis 80 Gew.-%, an Wirkstoffen der allgemeinen Formel (I) und deren Salzen. The agrochemical preparations, preferably herbicidal or plant growth-regulating agents of the present invention, preferably contain a total amount of from 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, more preferably 2 to 80 wt .-%, of active compounds of the general formula (I) and their salts.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige In wettable powders, the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Powdery
Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0,05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. Formulations contain 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 .-% of active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH- Wert und die Viskosität beeinflussende Mittel. Beispiele für Formulierungshilfsmittel sind unter anderem in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998) beschrieben. In addition, the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent. Examples of formulation auxiliaries are described inter alia in "Chemistry and Technology of Agrochemical Formulations", ed. D.A. Knowles, Kluwer Academic Publishers (1998).
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze können als solche oder in Form ihrer Zubereitungen (Formulierungen) mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Nematiziden, Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder Wachstumsregulatoren kombiniert eingesetzt werden, z.B. als Fertigformulierung oder als The compounds of the general formula (I) according to the invention or their salts can be used as such or in the form of their formulations (formulations) with other pesticidally active substances, such as, for example, Insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, e.g. as finished formulation or as
Tankmischungen. Die Kombinationsformulierungen können dabei auf Basis der obengenannten Formulierangen hergestellt werden, wobei die physikalischen Eigenschaften und Stabilitäten der zu kombinierenden Wirkstoffe zu berücksichtigen sind. Tank mixes. The combination formulations can be based on the above Formulierangen be prepared, taking into account the physical properties and stabilities of the active ingredients to be combined.
Als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in Mischungsformulierangen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA-Carboxylase, Cellulose-Synthase, Enolpyravylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p-Hydroxyphenylpyravat- Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase berahen, einsetzbar, wie sie z.B. in Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 und der dort zitierten Literatur beschrieben sind. Examples of combination partners for the compounds of the general formula (I) according to the invention in mixture formulations or in the tank mix are known active compounds which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyravylshikimate-3-phosphate Synthase, glutamine synthetase, p-hydroxyphenylpyravate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase berahen, can be used, such as in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
Von besonderem Interesse ist die selektive Bekämpfung von Schadpflanzen in Kulturen von Nutz- und Zierpflanzen. Obgleich die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) bereits in vielen Kulturen sehr gute bis ausreichende Selektivität aufweisen, können prinzipiell in einigen Kulturen und vor allem auch im Falle von Mischungen mit anderen Herbiziden, die weniger selektiv sind, Phytotoxizitäten an den Kulturpflanzen auftreten. Diesbezüglich sind Kombinationen Of particular interest is the selective control of harmful plants in crops of commercial and ornamental plants. Although the compounds of the general formula (I) according to the invention already have very good to sufficient selectivity in many cultures, phytotoxicities on the crop plants can in principle occur in some crops and, above all, in the case of mixtures with other herbicides which are less selective. In this regard, combinations are
erfindungsgemäßer Verbindungen (I) von besonderem Interesse, welche die Verbindungen der allgemeinen Formel (I) bzw. deren Kombinationen mit anderen Herbiziden oder Pestiziden und Safenern enthalten. Die Safener, welche in einem antidotisch wirksamen Gehalt eingesetzt werden, reduzieren die phytotoxischen Nebenwirkungen der eingesetzten Herbizide/Pestizide, z.B. in wirtschaftlich bedeutenden Kulturen wie Getreide (Weizen, Gerste, Roggen, Mais, Reis, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, vorzugsweise Getreide. Die Gewichtsverhältnisse von Herbizid(mischung) zu Safener hängt im Allgemeinen von der Compounds (I) of particular interest according to the invention which contain the compounds of general formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, oilseed rape, cotton and soybeans, preferably cereals. The weight ratios of herbicide (mixture) to safener generally depends on the
Aufwandmenge an Herbizid und der Wirksamkeit des jeweiligen Safeners ab und kann innerhalb weiter Grenzen variieren, beispielsweise im Bereich von 200: 1 bis 1 :200, vorzugsweise 100: 1 bis 1 : 100, insbesondere 20: 1 bis 1 :20. Die Safener können analog den Verbindungen der allgemeinen Formel (I) oder deren Mischungen mit weiteren Herbiziden/Pestiziden formuliert werden und als  Application rate of herbicide and the effectiveness of each safener and may vary within wide limits, for example in the range of 200: 1 to 1: 200, preferably 100: 1 to 1: 100, especially 20: 1 to 1: 20. The safeners can be formulated analogously to the compounds of the general formula (I) or mixtures thereof with further herbicides / pesticides and as
Fertigformulierang oder Tankmischung mit den Herbiziden bereitgestellt und angewendet werden. Fertigformulierang or tank mix with the herbicides are provided and applied.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Herbizid- oder Herbizid- Safener- Formulierangen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Äußere Bedingungen wie Temperatur, Feuchtigkeit etc. beeinflussen zu einem gewissen Teil die Aufwandmenge der Verbindungen der allgemeinen Formel (I) und/oder deren Salze. Die For use, the herbicidal or herbicidal safening formulations present in commercial form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use. External conditions such as temperature, humidity, etc. influence to a certain extent the application rate of the compounds of general formula (I) and / or their salts. The
Aufwandmenge kann dabei innerhalb weiter Grenzen variieren. Für die Anwendung als Herbizid zur Bekämpfung von Schadpflanzen liegt die Gesamtmenge an Verbindungen der allgemeinen Formel (I) und deren Salze vorzugsweise im Bereich von 0,001 bis 10,0 kg/ha, bevorzugt im Bereich von 0,005 bis 5 kg/ha, weiter bevorzugt im Bereich von 0,01 bis 1,5 kg/ha, insbesondere bevorzugt im Bereich von 0,05 bis 1 kg/ha. Dies gilt sowohl für die Anwendung im Vorauflauf oder im Nachauflauf. Application rate can vary within wide limits. For use as a herbicide for controlling harmful plants, the total amount of compounds of general formula (I) and their salts is preferably in the range of 0.001 to 10.0 kg / ha, preferably in the range of 0.005 to 5 kg / ha, more preferably in Range of 0.01 to 1.5 kg / ha, particularly preferably in the range of 0.05 to 1 kg / ha. This applies both to pre-emergence or post-emergence applications.
Bei der Anwendung von erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salzen als Pflanzenwachstumsregulator, beispielsweise als Halmverkürzer bei Kulturpflanzen, wie sie oben genannt worden sind, vorzugsweise bei Getreidepflanzen wie Weizen, Gerste, Roggen, Triticale, Hirse, Reis oder Mais, liegt die Gesamt- Aufwandmenge vorzugsweise im Bereich von 0,001 bis 2 kg/ha, vorzugsweise im Bereich von 0,005 bis 1 kg/ha, insbesondere im Bereich von 10 bis 500 g/ha, ganz besonders bevorzugt im Bereich von 20 bis 250 g/ha. Dies gilt sowohl für die Anwendung im In the application of compounds of the general formula (I) according to the invention and / or salts thereof as a plant growth regulator, for example as Halmverkürzer in crops, as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or corn , the total application rate is preferably in the range of 0.001 to 2 kg / ha, preferably in the range of 0.005 to 1 kg / ha, in particular in the range of 10 to 500 g / ha, very particularly preferably in the range of 20 to 250 g / Ha. This applies to both the application in the
Vorauflauf oder im Nachauflauf. Pre-emergence or postemergence.
Die Applikation als Halmverkürzer kann in verschiedenen Stadien des Wachstums der Pflanzen erfolgen. Bevorzugt ist beispielsweise die Anwendung nach der Bestückung am Beginn des The application as Halmverkürzer can be done in various stages of growth of the plants. For example, the application is preferred after placement at the beginning of
Längenwachstums . Length growth.
Alternativ kommt bei der Anwendung als Pflanzenwachstumsregulator auch die Behandlung des Saatguts in Frage, welche die unterschiedlichen Saatgutbeiz- und Beschichtungstechniken einschließt. Die Aufwandmenge hängt dabei von den einzelnen Techniken ab und kann in Vorversuchen ermittelt werden. Alternatively, when used as a plant growth regulator, seed treatment may be considered, including the different seed dressing and coating techniques. The application rate depends on the individual techniques and can be determined in preliminary tests.
Als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in erfindungsgemäßen Mitteln (z.B. Mischungsformulierungen oder im Tank-Mix) sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA- Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p- Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II oder As combination partners for the compounds of the general formula (I) according to the invention (eg mixture formulations or in tank mix), for example, known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvyl shikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or
Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", 16th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2012 und dort zitierter Literatur beschrieben sind. Nachfolgend werden beispielhaft bekannte Herbizide oder Pflanzenwachstumsregulatoren genannt, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, wobei diese Wirkstoffe entweder mit ihrem "common name" in der englischsprachigen Variante gemäß International Organization for Standardization (ISO) oder mit dem chemischen Namen bzw. mit der Codenummer bezeichnet sind. Dabei sind stets sämtliche Anwendungsformen wie beispielsweise Säuren, Salze, Ester sowie auch alle isomeren Formen wie Stereoisomere und optische Isomere umfaßt, auch wenn diese nicht explizit erwähnt sind. Protoporphyrinogen oxidase based, for example, as described in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and cited therein. The following are examples of known herbicides or plant growth regulators, which can be combined with the compounds of the invention, these agents either with their "common name" in the English version according to International Organization for Standardization (ISO) or with the chemical name or with the code number are designated. There are always all Use forms such as acids, salts, esters as well as all isomeric forms such as stereoisomers and optical isomers, even if they are not explicitly mentioned.
Beispiele für solche herbiziden Mischungspartner sind: Examples of such herbicidal mixture partners are:
Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim- sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac- sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3- one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen- ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2- Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-lH-tetrazol-l-yl]-phenyl]-ethansulfonamid, F- 7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-lH-benzimidazol-4-yl]-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P- ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M- methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methylphenyl ) -5-fluoropyridines-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachloro- potassium, aminocyclopyrachloromethyl, aminopyralid, amitrole, ammonium sulfamates, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron , bensulphon-methyl, bensulide, bentazone, benzobicyclone, benzofenap, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxime, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoates and -octanoates, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butraline, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorobromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, ch lorflurenol, chlorofurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlororthal-dimethyl, chlorosulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium, -diolamine , -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium , daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4-dimethyl-1,2-oxazolidine-3 - one, 2- (2,5-dichlorobenzyl) -4,4-dimethyl-l, 2-oxazolidin-3-one, dichloroprop, dichloroprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozine, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-9600, F-5231, ie N- [2-Chloro-4-fluoro-5- [4- (3-fluoro-propyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide, F-7967, ie 3- [7-chloro-5-fluoro-2- (trifluoromethyl) -1H-benzimidazol-4-yl] -1-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop- P-butyl,
flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, - dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfüron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, forarnsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium und -trimesium, H-9201, i.e. 0-(2,4-Dimethyl-6-nitrophenyl)-0-ethyl- isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron- methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. l-(Dimethoxyphosphoryl)-ethyl-(2,4- dichlorphenoxy)acetat, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin- ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-l - methyl-3-(trifluormethyl)- 1 H-pyrazol-4-yl]methyl} sulfonyl)-5,5-dimethyl-4,5-dihydro- 1 ,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium und -sodium, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, fluometuron, flurenol, flurenol-butyl, - dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, forarnsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, ie 0- (2,4-dimethyl-6-nitrophenyl) -O-ethyl-isopropylphosphoramidothioate, halo-tylose, halo-cyano-methyl, halosafenone, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfopethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW -02, ie 1- (dimethoxyphosphoryl) ethyl- (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamoxammonium, imazapic, imazapicammonium, imazapyr, imazapyrisopropylammonium, imazaquin, imazaquinammonium , imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indazifla m, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, ie 3 - ({[5- (difluoromethyl) -l - methyl-3- (trifluoromethyl) -1 H -pyrazol-4-yl] methyl} sulfonyl) -5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA , MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecopropane P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione,
methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzothiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron,
methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(l-methylethyl)- phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-l-methyl- 5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen- ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron- ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, , SYN-523, SYP-249, i.e. l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl- 5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. l-[7-Fluor-3-oxo-4-(prop-2-in-l- yl)-3,4-dihydro-2H-l,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone- methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vemolate, XDE-848, ZJ-0862, i.e. 3,4-Dichlor-N- {2- [(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: methabenzthiazuron, methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, ie N- [3-chloro -4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamide, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisul furon, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufenethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuronethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid , pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil , sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,, SYN-523, SYP-249, ie, 1-ethoxy-3-methyl-1-oxobut-3-ene -2-yl 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300, ie 1- [7-fluoro-3-oxo-4- (prop-2-yn-1-yl) -3 , 4-dihydro-2H-l, 4-benzoxazin-6-yl] -3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron , tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumetone, terbuthylazine, terbutryn, thenylchloro, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron , triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vemolate, XDE-848, ZJ-0862, ie 3,4-dichloro N- {2- [(4,6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following compounds:
Beispiele für Pflanzenwachstumsregulatoren als mögliche Mischungspartner sind: Examples of plant growth regulators as possible mixing partners are:
Acibenzolar, acibenzolar-S-methyl, 5-Aminolävulinsäure, ancymidol, 6-benzylaminopurine, Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine,
Brassinolid, Catechin, chlormequat chloride, cloprop, cyclanilide, 3-(Cycloprop-l-enyl)propionsäure, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, und mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4- indol-3-ylbutyric acid, isoprothiolane, probenazole, Jasmonsäure, Jasmonsäuremethylester, maleic hydrazide, mepiquat chloride, 1 -methylcyclopropene, 2-(l-naphthyl)acetamide, 1 -naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-0x0-4 [(2 -phenylethyl)amino]buttersäure, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, Salicylsäure, Strigolacton, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P. Brassinolide, catechin, chloroformate chloride, cloprop, cyclanilide, 3- (cycloprop-1-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothaldipotassium, -disodium, and mono (N, N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-yl-butyric acid, isoprothiolane, probenazole, jasmonic acid, methyl jasmonate maleic hydrazides, mepiquat chloride, 1-methylcyclopropene, 2- (1-naphthyl) acetamide, 1 -naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate-mixture, 4-0x0-4 [(2-phenylethyl) amino] butyric acid, paclobutrazole , N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
Ebenfalls als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) kommen beispielsweise die folgenden Safener in Frage: Verbindungen aus der Gruppe heterocyclischer Carbonsäurederivate: Also suitable as combination partners for the compounds of the general formula (I) according to the invention are, for example, the following safeners: Compounds from the group of heterocyclic carboxylic acid derivatives:
Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (Sla), vorzugsweiseDichlorophenylpyrazoline-3-carboxylic acid type compounds (Sl a ), preferably
Verbindungen wie Connections like
l-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure, l- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid,
1 -(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäureethylester (S 1 - 1 ) ("Mefenpyr-diethyl"), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind; 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S 1 - 1) ("mefenpyr-diethyl"), and related compounds as described in WO -A-91/07874;
Derivate der Dichlorphenylpyrazolcarbonsäure (Slb), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-methylpyrazol-3 -carbonsäureethylester (S 1 -2), Derivatives of dichlorophenylpyrazolecarboxylic acid (Sl b ), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (S 1 -2),
l-(2,4-Dichlorphenyl)-5-isopropylpyrazol-3-carbonsäureethylester (Sl-3), Ethyl l- (2,4-dichlorophenyl) -5-isopropylpyrazole-3-carboxylate (Sl-3),
1 -(2,4-Dichlorphenyl)-5-(l , 1 -dimethyl-ethyl)pyrazol-3-carbonsäureethylester (Sl -4) und verwandte Verbindungen, wie sie in EP-A-333131 und EP-A-269806 beschrieben sind; Ethyl 1 - (2,4-dichlorophenyl) -5- (1,1-dimethyl-ethyl) pyrazole-3-carboxylate (S1 -4) and related compounds as described in EP-A-333131 and EP-A-269806 are;
Derivate der l,5-Diphenylpyrazol-3-carbonsäure (Slc), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester (S 1 -5), Derivatives of l, 5-diphenylpyrazole-3-carboxylic acid (Sl c ), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S 1 -5),
l-(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (Sl-6) und verwandte 1- (2-chlorophenyl) -5-phenylpyrazole-3-carboxylic acid methyl ester (Sl-6) and related
Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind; Compounds as described, for example, in EP-A-268554;
Verbindungen vom Typ der Triazolcarbonsäuren (Sld), vorzugsweise Verbindungen wie Fenchlorazol(-ethylester), d.h. l-(2,4-Dichlorphenyl)-5-trichlormethyl-(lH)-l,2,4-triazol-3- carbonsäureethylester (Sl-7), und verwandte Verbindungen, wie sie in EP-A- 174562 und EP-A-346620 beschrieben sind; Compounds of the type of triazolecarboxylic acids (Sl d ), preferably compounds such as fenchlorazole (ethyl ester), ie ethyl 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1H) -l, 2,4-triazole-3-carboxylate ( Sl-7), and related compounds as described in EP-A-174562 and EP-A-346620;
Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5,5- Diphenyl-2-isoxazolin-3-carbonsäure(Sle), vorzugsweise Verbindungen wie Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid type or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
5-(2,4-Dichlorbenzyl)-2-isoxazolin-3 -carbonsäureethylester (Sl-8) oder 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (Sl-8) or
5-Phenyl-2-isoxazolin-3-carbonsäureethylester (Sl-9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazolin-carbonsäure (Sl-10) oder 5,5-Diphenyl-2-isoxazolin-3-carbonsäureethylester (Sl-11) ("Isoxadifen-ethyl")  5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-9) and related compounds, as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (Sl-10 ) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (Sl-11) ("isoxadifen-ethyl")
oder -n-propylester (Sl-12) oder 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3-carbon- säureethylester (Sl-13), wie sie in der Patentanmeldung WO-A-95/07897 beschrieben sind. Verbindungen aus der Gruppe der 8-Chinolinoxyderivate (S2): or -n-propyl ester (Sl-12) or 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-13), as described in the patent application WO-A-95/07897 are described. Compounds from the group of the 8-quinolinoxy derivatives (S2):
Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise Compounds of the 8-quinolinoxyacetic acid type (S2 a ), preferably
(5 -Chlort ^-chinolinoxy)essij *säure-(l-methylhexyl)-ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-quinolinoxy) -acetic acid (1-methylhexyl) ester ("cloquintocet-mexyl") (S2-1),
(5 -Chlort ^-chinolinoxy)essij *säure-(l,3-dimethyl-but-l -yl)-ester (S2-2), (5-chloro-quinolinoxy) -acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2),
(5 -Chlort ^-chinolinoxy)essij *säure-4-allyl-oxy-butylester (S2-3),  (5-chloro-quinolinoxy) -acetyl-4-allyl-oxy-butyl-ester (S2-3),
(5 -Chlort ^-chinolinoxy)essij ^säure- 1 -allyloxy-prop-2-ylester (S2-4),  (5-chloro-quinolinoxy) -salicyl-1-allyloxy-prop-2-yl ester (S2-4),
(5 -Chlort ^-chinolinoxy)essij jsäureethylester (S2-5),  (5-chloro-quinolinoxy) ethyl acetate (S2-5),
(5 -Chlort ^-chinolinoxy)essij *säuremethylester (S2-6),  Methyl (5-chloro-quinolinoxy) -acetate (S2-6),
(5 -Chlort ^-chinolinoxy)essij jsäureallylester (S2-7), (5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden-iminoxy)-l-ethylester (S2-8), (5-chloro-quinolinoxy) -acetyl-allyl ester (S2-7), (5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -l-ethyl ester (S2-8),
(5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop-l -ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86750, EP-A-94349 und EP-A-191736 oder EP-A-0 492 366 beschrieben sind, sowie (5-Chlor-8-chinolinoxy)essigsäure (S2-10), deren Hydrate und Salze, beispielsweise deren Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze wie sie in der WO-A-2002/34048 beschrieben sind;  (5-chloro-8-quinolinoxy) acetic acid 2-oxo-prop-1-yl-ester (S2-9) and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191736 or US Pat EP-A-0 492 366 and (5-chloro-8-quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium and aluminum salts. Iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002/34048;
Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid (S2 b ), preferably
Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester,  Compounds such as diethyl (5-chloro-8-quinolinoxy) malonate,
(5-Chlor-8-chinolinoxy)malonsäurediallylester,  (5-chloro-8-quinolinoxy) malonate,
(5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind.  (5-chloro-8-quinolinoxy) malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198.
S3) Wirkstoffe vom Typ der Dichloracetamide (S3), die häufig als Vorauflaufsafener  S3) Dichloroacetamide-type drugs (S3), often used as pre-emergence safeners
(bodenwirksame Safener) angewendet werden, wie z. B.  (soil-active safeners) are used, such. B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1),  "Dichloromid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1),
"R-29148" (3-Dichloracetyl-2,2,5-trimethyl-l,3-oxazolidin) der Firma Stauffer (S3-2), "R-28725" (3-Dichloracetyl-2,2,-dimethyl-l,3-oxazolidin) der Firma Stauffer (S3-3),  "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloro-acetyl-2,2-dimethyl) 1, 3-oxazolidine) from Stauffer (S3-3),
"Benoxacor" (4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin) (S3-4),  "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
"PPG-1292" (N-Allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloracetamid) der Firma PPG  "PPG-1292" (N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide) from PPG
Industries (S3-5),  Industries (S3-5),
"DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6),  "DKA-24" (N-allyl-N - [(allylaminocarbonyl) methyl] -dichloroacetamide) from Sagro-Chem (S3-6),
"AD-67" oder "MON 4660" (3-Dichloracetyl-l-oxa-3-aza-spiro[4,5]decan) der Firma  "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from the company
Nitrokemia bzw. Monsanto (S3-7),  Nitrokemia and Monsanto (S3-7),
"TI-35" (1-Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8),  "TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
"Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9)  "Diclonone" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9)
((RS)-l-Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-on) der Firma BASF, "Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyloxazolidin) (S3-10), sowie dessen (R)-Isomer (S3-11).  ((RS) -1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF, "furilazole" or "MON 13900" ((RS) -3-dichloroacetyl) 5- (2-furyl) -2,2-dimethyloxazolidine) (S3-10) and its (R) isomer (S3-11).
S4) Verbindungen aus der Klasse der Acylsulfonamide (S4): S4) Compounds of the class of acylsulfonamides (S4):
S4a) N-Acylsulfonamide der Formel (S4a) und deren Salze wie sie in der WO-A-97/45016 S4 a ) N-acylsulfonamides of the formula (S4 a ) and salts thereof as described in WO-A-97/45016
worin RA1 (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch VA wherein RA 1 (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, where the 2 last-mentioned radicals are represented by VA
Substituenten aus der Gruppe Halogen, (Ci-C4)Alkoxy, (Ci-C6)Haloalkoxy und (Ci- C4)Alkylthio und im Falle cyclischer Reste auch durch (Ci-C4)Alkyl und  Substituents from the group halogen, (Ci-C4) alkoxy, (Ci-C6) haloalkoxy and (Ci-C4) alkylthio and in the case of cyclic radicals by (Ci-C4) alkyl and
(Ci-C4)Haloalkyl substituiert sind;  (C 1 -C 4) haloalkyl are substituted;
RA2 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3; RA 2 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
niA 1 oder 2;  niA 1 or 2;
VA ist 0, 1 , 2 oder 3 bedeuten; V A is 0, 1, 2 or 3;
Verbindungen vom Typ der 4-(Benzoylsulfamoyl)benzamide der Formel (S4b) und deren Salze, Compounds of the 4- (benzoylsulfamoyl) benzamide of the formula (S4 b) and salts thereof,
worin  wherein
RB1, RB2 unabhängig voneinander Wasserstoff, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (C3-RB 1 , RB 2 independently of one another are hydrogen, (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -alkyl,
C6)Alkenyl, (C3-C6)Alkinyl, C 6 ) alkenyl, (C 3 -C 6 ) alkynyl,
RB 3 Halogen, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl oder (Ci-C4)Alkoxy und R B 3 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl or (Ci-C 4 ) alkoxy and
ms 1 oder 2 bedeuten,  ms 1 or 2 mean
z.B. solche worin  e.g. such
RB1 = Cyclopropyl, RB 2 = Wasserstoff und (RB3) = 2-OMe ist ("Cyprosulfamide", S4-1),RB 1 = cyclopropyl, R B 2 = hydrogen and (RB 3 ) = 2-OMe ("Cyprosulfamide", S4-1),
RB1 = Cyclopropyl, RB 2 = Wasserstoff und (RB3) = 5-Cl-2-OMe ist (S4-2), RB 1 = cyclopropyl, R B 2 = hydrogen and (RB 3 ) = 5-Cl-2-OMe (S4-2),
RB1 = Ethyl, RB 2 = Wasserstoff und (RB3) = 2-OMe ist (S4-3), RB 1 = ethyl, R B 2 = hydrogen and (RB 3 ) = 2-OMe (S4-3),
RB1 = Isopropyl, RB 2 = Wasserstoff und (RB3) = 5-Cl-2-OMe ist (S4-4) und RB 1 = isopropyl, R B 2 = hydrogen and (RB 3 ) = 5-Cl-2-OMe is (S4-4) and
RB1 = Isopropyl, RB 2 = Wasserstoff und (RB3) = 2-OMe ist (S4-5); RB 1 = isopropyl, R B 2 = hydrogen and (RB 3 ) = 2-OMe (S4-5);
S4C) Verbindungen aus der Klasse der Benzoylsulfamoylphenylharnstoffe der Formel (S4C), wie sie S4 C ) Compounds of the class of the Benzoylsulfamoylphenylharnstoffe of the formula (S4 C ), as they
worin  wherein
Rc1, Rc unabhängig voneinander Wasserstoff, (Ci-Cg)Alkyl, (C3-Cg)Cycloalkyl, (C3-Rc 1 , Rc are independently hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-
C6)Alkenyl, (C3-C6)Alkinyl, C 6 ) alkenyl, (C 3 -C 6 ) alkynyl,
Rc Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3 und Rc is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3 and
1 oder 2 bedeuten;  1 or 2;
beispielsweise 1 - [4-(N-2-Methoxybenzoylsulfamoyl)phenyl] -3 -methylharnstoff, for example 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
1 - [4-(N-2-Methoxybenzoylsulfamoyl)phenyl] -3 ,3 -dimethylharnstoff,  1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
l-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylharnstoff;  l- [4- (N-4,5-Dimethylbenzoylsulfamoyl) phenyl] -3-methyl urea;
Verbindungen vom Typ der N-Phenylsulfonylterephthalamide der Formel (S4d) und deren Salze, Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4 d ) and salts thereof,
worin  wherein
RD 4 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3; R D 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
mD 1 oder 2;  mD 1 or 2;
RD 5 Wasserstoff, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C5-R D 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -
Ce)Cycloalkenyl bedeutet. Ce) cycloalkenyl.
S5) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch-aliphatischen  S5) active ingredients from the class of hydroxyaromatic and aromatic-aliphatic
Carbonsäurederivate (S5), z.B.  Carboxylic acid derivatives (S5), e.g.
3,4,5-Triacetoxybenzoesäureethylester, 3,5-Dimethoxy-4-hydroxybenzoesäure, 3,5- Dihydroxybenzoesäure, 4-Hydroxysalicylsäure, 4-Fluorsalicyclsäure, 2-Hydroxyzimtsäure, 2,4- Dichlorzimtsäure, wie sie in der WO-A-2004/084631, WO-A-2005/015994, WO-A- 2005/016001 beschrieben sind.  3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A- 2004/084631, WO-A-2005/015994, WO-A-2005/016001.
S6) Wirkstoffe aus der Klasse der l,2-Dihydrochinoxalin-2-one (S6), z.B.  S6) active compounds from the class of 1,2-dihydroquinoxaline-2-ones (S6), e.g.
l-Methyl-3-(2-thienyl)-l,2-dihydrochinoxalin-2-on, l-Methyl-3-(2-thienyl)-l,2-dihydro- chinoxalin-2-thion, l-(2-Aminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-on-hydrochlorid, l-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-on, wie sie in der WO- A-2005/112630 beschrieben sind.  1-methyl-3- (2-thienyl) -1,2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-thione, 1- (2 -Aminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxaline-2-one hydrochloride, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxaline 2-on, as described in WO-A-2005/112630.
S7) Verbindungen aus der Klasse der Diphenylmethoxyessigsäurederivate (S7), z.B.  S7) compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g.
Diphenylmethoxyessigsäuremethylester (CAS-Reg.Nr. 41858-19-9) (S7-1),  Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1),
Diphenylmethoxyessigsäureethylester oder Diphenylmethoxyessigsäure wie sie in der WO-A- 98/38856 beschrieben sind.  Diphenylmethoxyessigsäureethylester or Diphenylmethoxyessigsäure as described in WO-A-98/38856.
S8) Verbindungen der Formel (S8), wie sie in der WO-A-98/27049 beschrieben sind,  S8) compounds of the formula (S8) as described in WO-A-98/27049,
worin die Symbole und Indizes folgende Bedeutungen haben: RD1 ist Halogen, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, RD2 ist Wasserstoff oder (Ci-C4)Alkyl, wherein the symbols and indices have the following meanings: RD 1 is halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, RD 2 is hydrogen or (Ci-C 4) alkyl,
3  3
R D ist Wasserstoff, (Ci-Cg)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; oder deren Salze, RD is hydrogen, (Ci-Cg) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted; or their salts,
nD ist eine ganze Zahl von 0 bis 2. n D is an integer from 0 to 2.
S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B. S9) Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
1 ,2-Dihydro-4-hydroxy- 1 -ethyl-3-(5-tetrazolylcarbonyl)-2-chinolon (CAS-Reg.Nr. : 219479- 18- 1,2-Dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 219479-18-
2), l,2-Dihydro-4-hydroxy-l-methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr. 2), 1,2-dihydro-4-hydroxy-1-methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS Reg.
95855-00-8), wie sie in der WO-A- 1999/000020 beschrieben sind.  95855-00-8), as described in WO-A-1999/000020.
S10) Verbindungen der Formeln (S10a) oder (S10b), S10) compounds of the formulas (S10 a ) or (S10 b ),
wie sie in der WO-A-2007/023719 und WO-A-2007/023764 beschrieben sind,  as described in WO-A-2007/023719 and WO-A-2007/023764,
(S10A) (S10B) (S10 A ) (S10 B )
worin wherein
RE1 Halogen, (Ci-C4)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 RE 1 halogen, (C 1 -C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
YE, ZE unabhängig voneinander O oder S, YE, Z E independently of one another O or S,
nE eine ganze Zahl von 0 bis 4, n E is an integer from 0 to 4,
RE2 (Ci-Ci6)Alkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, RE 2 (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl,
RE3 Wasserstoff oder (Ci-Ce)Alkyl bedeuten. RE 3 is hydrogen or (Ci-Ce) alkyl.
Si l) Wirkstoffe vom Typ der Oxyimino- Verbindungen (Si l), die als Saatbeizmittel bekannt sind, wie z. B.  Si l) active ingredients of the type of oxyimino compounds (Si l), which are known as seed dressing, such as. B.
"Oxabetrinil" ((Z)-l,3-Dioxolan-2-ylmethoxyimino(phenyl)acetonitril) (Sl 1-1), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist,  "Oxabetrinil" ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl 1-1), which is known as millet safener for millet against damage by metolachlor,
"Fluxofenim" (l-(4-Chlorphenyl)-2,2,2-trifluor-l-ethanon-0-(l,3-dioxolan-2-ylmethyl)-oxim) (Sl 1-2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, und "Cyometrinil" oder "CGA-43089" ((Z)-Cyanomethoxyimino(phenyl)acetonitril) (Sl l-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist.  "Fluxofenim" (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-0- (1,3-dioxolan-2-ylmethyl) -oxime) (S1-2) used as seed dressing Safener for millet against damage by metolachlor, and "Cyometrinil" or "CGA-43089" ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is used as a seed dressing safener for millet against damage from metolachlor is known.
S12) Wirkstoffe aus der Klasse der Isothiochromanone (S12), wie z.B. Methyl- [(3 -oxo-lH-2- benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121-04-6) (S12-1) und verwandte Verbindungen aus WO-A-1998/13361. Eine oder mehrere Verbindungen aus Gruppe (S13): S12) active substances from the class of the isothiochromanones (S12), such as, for example, methyl [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS No. 205121-04-6 ) (S12-1) and related compounds of WO-A-1998/13361. One or more compounds from group (S13):
"Naphthalic anhydrid" (1 ,8-Naphthalindicarbonsäureanhydrid) (S13-1), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist,  "Naphthalene anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides.
"Fenclorim" (4,6-Dichlor-2-phenylpyrimidin) (S13-2), das als Safener für Pretilachlor in gesätem Reis bekannt ist,  "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as safener for pretilachlor in sown rice,
"Flurazole" (Benzyl-2-chlor-4-trifluormethyl-l ,3-thiazol-5-carboxylat) (S 13-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metolachlor bekannt ist,  "Flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S 13-3), which is known as a seeder-safener for millet against damage by alachlor and metolachlor,
"CL 304415" (CAS-Reg.Nr. 31541 -57-8)  "CL 304415" (CAS No. 31541 -57-8)
(4-Carboxy-3,4-dihydro-2H-l -benzopyran-4-essigsäure) (S13-4) der Firma American  (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American
Cyanamid, das als Safener für Mais gegen Schäden von Imidazolinonen bekannt ist,  Cyanamide, which is known as safener for maize against damage of imidazolinones,
"MG 191 " (CAS-Reg.Nr. 96420-72-3) (2-Dichlormethyl-2-methyl-l ,3-dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist,  "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
"MG 838" (CAS-Reg.Nr. 133993-74-5)  "MG 838" (CAS Reg. No. 133993-74-5)
(2-propenyl l -oxa-4-azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia "Disulfoton" (0,0-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7),  (2-propenyl 1 -oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia "Disulfoton" (O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),
"Dietholate" (0,0-Diethyl-O-phenylphosphorothioat) (S 13-8),  "Dietholate" (0,0-diethyl-O-phenyl phosphorothioate) (S 13-8),
"Mephenate" (4-Chlorphenyl-methylcarbamat) (S 13-9).  "Mephenate" (4-chlorophenyl methylcarbamate) (S 13-9).
S 14) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B.  S 14) active substances which, in addition to a herbicidal activity against harmful plants, also have safener action on crops such as rice, such as, for example, rice. B.
"Dimepiperate" oder "MY-93" (S-\ -Methyl- 1 -phenylethyl-piperidin-l -carbothioat), das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist,  "Dimepiperate" or "MY-93" (S-methyl-1-phenylethyl-piperidine-1-carbothioate) known as a safener for rice against damage by the herbicide Molinate,
"Daimuron" oder "SK 23" (l -(l -Methyl-l -phenylethyl)-3-p-tolyl-harnstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist,  "Daimuron" or "SK 23" (1- (1-methyl-1-phenylethyl) -3-p-tolyl-urea) known as a safener for rice against damage by the herbicide imazosulfuron,
"Cumyluron" = "JC-940" (3-(2-Chlorphenylmethyl)-l -(l -methyl-l -phenyl-ethyl)harnstoff, siehe JP-A-60087270), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist,  "Cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenyl-ethyl) urea, see JP-A-60087270) which can be used as safener for rice against damage of some herbicides is known, "methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxy-benzophenone), which is known as a safener for rice against damage of some herbicides,
"CSB" (l -Brom-4-(chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr. 54091 -06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist.  "CSB" (1-Bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Registry No. 54091-06-4), which is known as a safener against damage of some herbicides in rice.
S 15) Verbindungen der Formel (S 15) oder deren Tautomere,  S 15) compounds of the formula (S 15) or their tautomers,
wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind, worin as described in WO-A-2008/131861 and WO-A-2008/131860, wherein
einen (Ci-C6)Haloalkylrest bedeutet und  a (Ci-C6) haloalkyl radical and
Wasserstoff oder Halogen bedeutet und  Is hydrogen or halogen and
, RH4 unabhängig voneinander Wasserstoff, (Ci-Ci6)Alkyl, (C2-Ci6)Alkenyl oder , RH 4 are independently hydrogen, (Ci-Ci6) alkyl, (C 2 -Ci 6) alkenyl or
(C2-Ci6)Alkinyl, (C 2 -C 6) alkynyl,
wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C i)Alkoxy, (Ci-C i)Haloalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Alkylamino, Di[(Ci-C4)alkyl]-amino, [(Ci-C4)Alkoxy]- carbonyl, [(Ci-C4)Haloalkoxy]-carbonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, wherein each of the last-mentioned 3 unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C i) alkoxy, (Ci-C i) haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) Alkylamino, di [(C 1 -C 4 ) alkyl] amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6) cycloalkyl which is unsubstituted or phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted,
oder (C3-C6)Cycloalkyl, (C4-C6)Cycloalkenyl, (C3-C6)Cycloalkyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, or (C3-C6) cycloalkyl, (C 4 -C 6) cycloalkenyl, (C3-C6) cycloalkyl which is fused to one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 ) Cycloalkenyl fused on one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring,
wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Alkylamino, Di[(Ci- C4)alkyl]-amino, [(Ci-C4)Alkoxy]-carbonyl, [(Ci-C4)Haloalkoxy]-carbonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, wherein each of the last-mentioned 4 unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkylamino, di [(C 1 -C 4 ) alkyl] amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(Ci-C 4 ) haloalkoxy] -carbonyl, (C3-C6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,
bedeutet oder  means or
(Ci-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet und(C 1 -C 4 ) -Alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 4 ) haloalkoxy and
Wasserstoff oder (Ci-C4)-Alkyl bedeutet oder Is hydrogen or (C 1 -C 4 ) -alkyl or
und RH4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis achtgliedrigen and RH 4 together with the directly attached N atom form a four- to eight-membered one
heterocyclischen Ring, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, Nitro, (Ci- heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which may be unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, nitro,
C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy und (Ci-C4)Alkylthio substituiert ist, bedeutet. C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted, means.
) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf) Active ingredients, which are used primarily as herbicides, but also safener effect on
Kulturpflanzen aufweisen, z. B. Have crops, z. B.
(2,4-Dichlorphenoxy)essigsäure (2,4-D),  (2,4-dichlorophenoxy) acetic acid (2,4-D),
(4-Chlorphenoxy)essigsäure,  (4-chlorophenoxy) acetic acid,
(R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop),  (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop),
4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB), (4-Chlor-o-tolyloxy)essigsäure (MCPA), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB), (4-chloro-o-tolyloxy) acetic acid (MCPA),
4-(4-Chlor-o-tolyloxy)buttersäure,  4- (4-chloro-o-tolyloxy) butyric acid,
4-(4-Chlorphenoxy)buttersäure,  4- (4-chlorophenoxy) butyric acid,
3,6-Dichlor-2-methoxybenzoesäure (Dicamba),  3,6-dichloro-2-methoxybenzoic acid (Dicamba),
1 -(Ethoxycarbonyl)ethyl-3,6-dichlor-2-methoxybenzoat (Lactidichlor- ethyl).  1 - (ethoxycarbonyl) ethyl-3,6-dichloro-2-methoxybenzoate (lacto-dichloroethyl).
Bevorzugte Safener in Kombination mit den erfindungsgemäßen Verbindungend der allgemeinen Formel (I) und/oder deren Salze, insbesondere mit den Verbindungen der Formeln (1-1) bis (1-240) und/oder deren Salze sind: Cloquintocet-mexyl, Cyprosulfamid, Fenchlorazol-ethylester, Isoxadifen- ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 und S4-5, und besonders bevorzugte Safener sind: Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl und Mefenpyr-diethyl.  Preferred safeners in combination with the compounds according to the invention of the general formula (I) and / or salts thereof, in particular with the compounds of the formulas (1-1) to (1-240) and / or salts thereof are: Cloquintocet-mexyl, cyprosulfamide, Fenchlorazole ethyl ester, isoxadifen ethyl, mefenpyr diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
Biologische Beispiele A. Herbizide Wirkung und Kulturverträglichkeit im Nachauflauf BIOLOGICAL EXAMPLES A. Herbicidal action and post-emergence culture compatibility
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen wurden in Kunststoff- oder Seeds of monocotyledonous or dicotyledonous weeds were cultivated in plastic or
Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter kontrollierten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat wurden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 1/ha auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Wood fiber pots laid in sandy loam soil, covered with soil and grown in the greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated in the single leaf stage. The compounds according to the invention formulated as wettable powders (WP) or as emulsion concentrates (EC) were then sprayed onto the green plant parts as an aqueous suspension or emulsion with the addition of 0.5% of additive at a rate of 600 l / ha. After about 3 weeks of service life of
Versuchspflanzen im Gewächshaus, unter optimalen Wachstumsbedingungen, wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0%> Wirkung = wie Kontrollpflanzen. Test plants in the greenhouse, under optimal growth conditions, the effect of the preparations was scored visually compared to untreated controls. For example, 100% means action = plants are dead, 0%> effect = like control plants.
In den nachstehenden Tabllen Bl bis B15 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß Tabelle I auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 1280 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. Tabelle Bl In the following Tables Bl to B15, the effects of selected compounds of the general formula (I) according to Table I on various harmful plants and an application rate corresponding to 1280 g / ha, which were obtained in accordance with the previously mentioned experimental procedure are shown. Table Bl
Verbindung connection
Alopecurus myosuroides Beispiel Nr.  Alopecurus myosuroides Example no.
1-140 100 1-140 100
1-133 100  1-133 100
1-093 100  1-093 100
1-158 100  1-158 100
1-141 80  1-141 80
1-126 100  1-126 100
1-060 90  1-060 90
1-036 90  1-036 90
1-183 90  1-183 90
1-044 90  1-044 90
1-087 90  1-087 90
1-163 90  1-163 90
1-122 90  1-122 90
1-092 90  1-092 90
1-069 100  1-069 100
1-157 100  1-157 100
1-155 90  1-155 90
1-090 100  1-090 100
1-120 90  1-120 90
1-097 90  1-097 90
1-091 80  1-091 80
1-134 90  1-134 90
1-062 80  1-062 80
1-192 80  1-192 80
1-063 100  1-063 100
1-089 90 Tabelle B2 1-089 90 Table B2
Verbindung  connection
Echinochloa crus-galli Beispiel Nr.  Echinochloa crus-galli Example Nr.
1-140 100  1-140 100
1-133 100  1-133 100
1-093 100  1-093 100
1-158 100  1-158 100
1-141 100  1-141 100
1-126 100  1-126 100
1-060 90  1-060 90
1-036 90  1-036 90
1-183 90  1-183 90
1-044 100  1-044 100
1-163 90  1-163 90
1-122 90  1-122 90
1-092 100  1-092 100
1-069 80  1-069 80
1-157 100  1-157 100
1-090 80  1-090 80
1-094 80  1-094 80
1-097 100  1-097 100
1-091 80  1-091 80
1-134 80  1-134 80
1-192 80  1-192 80
1-095 80  1-095 80
1-066 80 1-066 80
Tabelle B3 Table B3
Verbindung  connection
Setaria viridis Beispiel Nr.  Setaria viridis example no.
1-140 100 1-140 100
1-133 1001-133 100
1-093 1001-093 100
1-158 1001-158 100
1-141 901-141 90
1-126 1001-126 100
1-060 801-060 80
1-036 901-036 90
1-183 1001-183 100
1-044 1001-044 100
1-087 901-087 90
1-163 901-163 90
1-122 1001-122 100
1-092 1001-092 100
1-069 801-069 80
1-157 801-157 80
1-155 801-155 80
1-090 1001-090 100
1-120 801-120 80
1-097 901-097 90
1-091 1001-091 100
1-037 1001-037 100
1-203 901-203 90
1-064 1001-064 100
1-115 1001-115 100
1-063 801-063 80
1-089 801-089 80
1-205 801-205 80
1-211 90 Tabelle B4 1-211 90 Table B4
Verbindung  connection
Abutilon theophrasti Beispiel Nr.  Abutilon theophrasti Example no.
1-140 100 1-140 100
1-133 1001-133 100
1-093 901-093 90
1-158 901-158 90
1-141 901-141 90
1-126 1001-126 100
1-060 801-060 80
1-036 901-036 90
1-183 901-183 90
1-044 1001-044 100
1-087 801-087 80
1-163 901-163 90
1-122 1001-122 100
1-092 1001-092 100
1-069 801-069 80
1-157 901-157 90
1-155 801-155 80
1-090 1001-090 100
1-094 901-094 90
1-065 801-065 80
1-097 901-097 90
1-091 801-091 80
1-037 901-037 90
1-134 901-134 90
1-203 1001-203 100
1-064 801-064 80
1-115 1001-115 100
1-062 1001-062 100
1-136 901-136 90
1-192 801-192 80
1-063 1001-063 100
1-034 80 Verbindung 1-034 80 connection
Abutilon theophrasti Beispiel Nr.  Abutilon theophrasti Example no.
1-035 100  1-035 100
1-205 90  1-205 90
1-142 80  1-142 80
1-096 80  1-096 80
Tabelle B5 Table B5
Verbindung  connection
Amaranthus retroflexus Beispiel Nr.  Amaranthus retroflexus Example no.
1-140 100  1-140 100
1-133 100  1-133 100
1-093 100  1-093 100
1-158 100  1-158 100
1-141 100  1-141 100
1-126 100  1-126 100
1-060 100  1-060 100
1-036 100  1-036 100
1-183 100  1-183 100
1-044 100  1-044 100
1-087 100  1-087 100
1-092 100  1-092 100
1-069 100  1-069 100
1-157 100  1-157 100
1-155 100  1-155 100
1-090 100  1-090 100
1-094 100  1-094 100
1-120 80  1-120 80
1-065 100  1-065 100
1-097 80  1-097 80
1-091 80  1-091 80
1-037 100  1-037 100
1-134 100  1-134 100
1-203 100 Verbindung 1-203 100 connection
Amaranthus retroflexus Beispiel Nr.  Amaranthus retroflexus Example no.
1-064 100  1-064 100
1-115 100  1-115 100
1-062 100  1-062 100
1-136 100  1-136 100
1-063 100  1-063 100
1-034 100  1-034 100
1-095 100  1-095 100
1-205 90  1-205 90
1-135 100  1-135 100
1-066 80  1-066 80
1-032 90  1-032 90
1-186 100  1-186 100
1-156 100  1-156 100
1-207 90  1-207 90
1-058 80  1-058 80
1-142 90  1-142 90
1-121 80  1-121 80
1-137 80  1-137 80
1-188 100  1-188 100
Tabelle B6 Table B6
Verbindung  connection
Polygonum convolvulus Beispiel Nr.  Polygonum convolvulus Example no.
1-140 100  1-140 100
1-133 100  1-133 100
1-093 100  1-093 100
1-158 100  1-158 100
1-141 100  1-141 100
1-126 100  1-126 100
1-060 80  1-060 80
1-036 100 Verbindung 1-036 100 connection
Polygonum convolvulus Beispiel Nr.  Polygonum convolvulus Example no.
1-183 90  1-183 90
1-044 100  1-044 100
1-087 100  1-087 100
1-163 100  1-163 100
1-122 100  1-122 100
1-092 100  1-092 100
1-069 100  1-069 100
1-157 80  1-157 80
1-090 100  1-090 100
1-094 90  1-094 90
1-120 100  1-120 100
1-065 100  1-065 100
1-037 80  1-037 80
1-134 80  1-134 80
1-064 100  1-064 100
1-115 90  1-115 90
1-062 90  1-062 90
1-192 100  1-192 100
1-035 100  1-035 100
1-089 90  1-089 90
1-067 90  1-067 90
1-211 100  1-211 100
1-032 90  1-032 90
1-156 80  1-156 80
1-121 80  1-121 80
1-042 80  1-042 80
Tabelle B7 Table B7
Verbindung  connection
Stellaria media Beispiel Nr.  Stellaria media Example no.
1-140 90  1-140 90
1-133 100 Verbindung 1-133 100 connection
Stellaria media Beispiel Nr.  Stellaria media Example no.
1-093 100 1-093 100
1-158 901-158 90
1-141 1001-141 100
1-126 1001-126 100
1-060 1001-060 100
1-036 901-036 90
1-183 901-183 90
1-044 1001-044 100
1-087 1001-087 100
1-163 801-163 80
1-122 901-122 90
1-092 1001-092 100
1-155 901-155 90
1-090 1001-090 100
1-094 1001-094 100
1-120 901-120 90
1-065 901-065 90
1-037 1001-037 100
1-203 901-203 90
1-064 1001-064 100
1-115 1001-115 100
1-062 901-062 90
1-136 901-136 90
1-035 801-035 80
1-067 901-067 90
1-135 901-135 90
1-211 1001-211 100
1-032 1001-032 100
1-058 100 Tabelle B8 1-058 100 Table B8
Verbindung  connection
Viola tricolor Beispiel Nr.  Viola tricolor Example no.
1-140 100 1-140 100
1-133 1001-133 100
1-093 1001-093 100
1-158 1001-158 100
1-141 901-141 90
1-126 1001-126 100
1-060 1001-060 100
1-036 1001-036 100
1-183 1001-183 100
1-044 1001-044 100
1-087 1001-087 100
1-163 901-163 90
1-122 901-122 90
1-092 1001-092 100
1-069 1001-069 100
1-157 1001-157 100
1-155 1001-155 100
1-090 1001-090 100
1-094 1001-094 100
1-120 1001-120 100
1-065 1001-065 100
1-097 801-097 80
1-091 1001-091 100
1-037 1001-037 100
1-134 1001-134 100
1-203 1001-203 100
1-064 1001-064 100
1-115 1001-115 100
1-062 1001-062 100
1-136 1001-136 100
1-192 801-192 80
1-063 100 Verbindung 1-063 100 connection
Viola tricolor Beispiel Nr.  Viola tricolor Example no.
1-034 100 1-034 100
1-035 1001-035 100
1-095 1001-095 100
1-067 801-067 80
1-205 901-205 90
1-135 1001-135 100
1-066 1001-066 100
1-211 801-211 80
1-186 1001-186 100
1-156 1001-156 100
1-207 801-207 80
1-121 801-121 80
1-137 1001-137 100
1-038 901-038 90
1-039 1001-039 100
1-138 801-138 80
1-160 1001-160 100
1-230 80 1-230 80
Tabelle B9 Table B9
Verbindung  connection
Ipomoea purpurea Beispiel Nr.  Ipomoea purpurea Example no.
1-095 80 1-095 80
1-135 801-135 80
1-066 801-066 80
1-186 801-186 80
1-207 90 Tabelle BIO 1-207 90 Table BIO
Tabelle B12 Table B12
Verbindung  connection
Lolium rigidum Beispiel Nr.  Lolium rigidum Example no.
1-140 80 1-140 80
1-133 901-133 90
1-093 1001-093 100
1-158 1001-158 100
1-036 901-036 90
1-157 80 1-157 80
Tabelle Bl 3 Table Bl 3
Verbindung  connection
Matricaria inodora Beispiel Nr.  Matricaria inodora Example no.
1-140 100 1-140 100
1-126 801-126 80
1-060 801-060 80
1-065 80 1-065 80
Tabelle B14 Table B14
Verbindung  connection
Pharbitis purpurea Beispiel Nr.  Pharitis purpurea Example no.
1-140 100 1-140 100
1-133 1001-133 100
1-093 901-093 90
1-158 801-158 80
1-141 801-141 80
1-126 1001-126 100
1-183 1001-183 100
1-044 1001-044 100
1-087 801-087 80
1-163 901-163 90
1-122 901-122 90
1-092 801-092 80
1-155 801-155 80
1-094 100 Verbindung 1-094 100 connection
Pharbitis purpurea  Pharitis purpurea
Beispiel Nr.  Example no.
1-065 100  1-065 100
1-097 90  1-097 90
1-091 80  1-091 80
1-037 100  1-037 100
1-134 80  1-134 80
1-203 90  1-203 90
1-034 90  1-034 90
1-095 80  1-095 80
1-135 80  1-135 80
1-066 80  1-066 80
1-186 80  1-186 80
1-207 90  1-207 90
Tabelle Bl 5 Table Bl 5
Verbindung  connection
Hordeum murinum  Hordeum murinum
Beispiel Nr.  Example no.
1-140 80  1-140 80
1-133 90  1-133 90
1-093 90  1-093 90
1-126 80  1-126 80
1-069 80  1-069 80
Die Versuchsergebnisse belegen, dass erfindungsgemäße Verbindungen der allgemeinen Formel (I) bei Behandlung im Nachauflauf eine gute herbizide Wirksamkeit gegen ausgewählte Schadpflanzen wie z.B. Alopecurus myosuroides, Echinochloa crus-galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Polygonum convolvulus, Stellaria media, Viola tricolor, Ipomoea purpurea, Vcronica persica, Avena fatua, Hordeum murinum, Lolium rigidum, Matricaria inodora, Pharbitis purpurea bei einer jweiligen Aufwandmenge von 1280 g Aktivsubstanz pro Hektar aufweisen. Herbizide Wirkung und Kulturverträglichkeit im Vorauflauf The test results prove that compounds of the general formula (I) according to the invention have a good herbicidal activity against selected harmful plants such as Alopecurus myosuroides, Echinochloa crus-galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Polygonum convolvulus, Stellaria media, Viola Tricolor, Ipomoea purpurea, Vcronica persica, Avena fatua, Hordeum murinum, Lolium rigidum, Matricaria inodora, purpurea purpurea at a jweiligen application rate of 1280 g of active ingredient per hectare. Herbicidal action and culture compatibility in pre-emergence
Samen von mono- bzw. dikotylen Unkraut und Kulturpflanzen wurden in Kunststoff- oder Seeds of monocotyledonous or dicotyledonous weeds and crops were found in plastic or
Holzfasertöpfen ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 1/ha auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung wurden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Nach ca. 3 Wochen wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen in Prozentwerten bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0%> Wirkung = wie Kontrollpflanzen. Wood fiber pots designed and covered with soil. The compounds according to the invention formulated as wettable powders (WP) or as emulsion concentrates (EC) were then applied to the surface of the cover soil as an aqueous suspension or emulsion with the addition of 0.5% of additive at a rate of 600 l / ha. After treatment, the pots were placed in the greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was scored visually in comparison to untreated controls in percentages. For example, 100% means action = plants are dead, 0%> effect = like control plants.
In nachstehenden Tabllen Cl bis C 14 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß Tabelle I auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 1280 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. In the following Tables Cl to C 14, the effects of selected compounds of the general formula (I) according to Table I on various harmful plants and an application rate corresponding to 1280 g / ha, which were obtained in accordance with the previously mentioned experimental procedure are shown.
Tabelle Cl Table Cl
Verbindung connection
Alopecurus myosuroides  Alopecurus myosuroides
Beispiel Nr.  Example no.
1-205 100 1-205 100
1-126 100  1-126 100
1-093 100  1-093 100
1-091 100  1-091 100
1-158 100  1-158 100
1-094 100  1-094 100
1-095 100  1-095 100
1-044 100  1-044 100
1-133 100  1-133 100
1-069 100  1-069 100
1-134 100  1-134 100
1-135 100  1-135 100
1-062 100  1-062 100
1-092 100  1-092 100
1-036 90  1-036 90
1-140 100 Verbindung 1-140 100 connection
Alopecurus myosuroides Beispiel Nr.  Alopecurus myosuroides Example no.
1-157 100 1-157 100
1-141 90  1-141 90
1-089 90  1-089 90
1-097 100  1-097 100
1-090 100  1-090 100
1-037 100  1-037 100
1-211 90  1-211 90
1-066 80  1-066 80
1-122 100  1-122 100
1-155 100  1-155 100
1-192 100  1-192 100
1-163 90  1-163 90
1-183 100  1-183 100
1-136 100  1-136 100
1-039 100  1-039 100
1-063 100  1-063 100
1-067 90  1-067 90
1-038 80  1-038 80
1-115 90  1-115 90
1-064 90  1-064 90
1-203 90  1-203 90
1-096 100  1-096 100
1-120 90  1-120 90
1-142 80  1-142 80
Tabelle C2 Table C2
Verbindung connection
Setaria viridis Beispiel Nr.  Setaria viridis example no.
1-205 100 1-205 100
1-126 100  1-126 100
1-093 100 Verbindung 1-093 100 connection
Setaria viridis Beispiel Nr.  Setaria viridis example no.
1-091 1001-091 100
1-158 1001-158 100
1-094 1001-094 100
1-095 1001-095 100
1-044 1001-044 100
1-133 1001-133 100
1-069 1001-069 100
1-134 1001-134 100
1-135 1001-135 100
1-062 1001-062 100
1-092 1001-092 100
1-036 1001-036 100
1-140 1001-140 100
1-157 1001-157 100
1-141 1001-141 100
1-089 1001-089 100
1-097 1001-097 100
1-090 1001-090 100
1-037 1001-037 100
1-211 1001-211 100
1-066 1001-066 100
1-122 1001-122 100
1-155 1001-155 100
1-192 1001-192 100
1-163 1001-163 100
1-183 1001-183 100
1-136 1001-136 100
1-039 901-039 90
1-063 1001-063 100
1-067 1001-067 100
1-038 1001-038 100
1-115 1001-115 100
1-064 100 Verbindung 1-064 100 connection
Setaria viridis Beispiel Nr.  Setaria viridis example no.
1-203 1001-203 100
1-096 1001-096 100
1-087 1001-087 100
1-156 1001-156 100
1-060 901-060 90
1-065 1001-065 100
1-207 1001-207 100
1-142 1001-142 100
1-121 901-121 90
1-138 1001-138 100
1-186 1001-186 100
1-042 801-042 80
1-188 1001-188 100
1-137 1001-137 100
1-034 1001-034 100
1-035 90 1-035 90
Tabelle C3 Table C3
Verbindung connection
Abutilon theophrasti Beispiel Nr.  Abutilon theophrasti Example no.
1-205 1001-205 100
1-126 1001-126 100
1-093 1001-093 100
1-091 1001-091 100
1-158 1001-158 100
1-094 1001-094 100
1-095 1001-095 100
1-044 1001-044 100
1-133 1001-133 100
1-069 1001-069 100
1-134 1001-134 100
1-135 1001-135 100
1-062 1001-062 100
1-092 1001-092 100
1-036 1001-036 100
1-140 1001-140 100
1-157 1001-157 100
1-141 1001-141 100
1-089 1001-089 100
1-097 1001-097 100
1-090 1001-090 100
1-037 1001-037 100
1-211 901-211 90
1-066 901-066 90
1-122 1001-122 100
1-155 1001-155 100
1-192 1001-192 100
1-163 1001-163 100
1-183 1001-183 100
1-136 1001-136 100
1-039 1001-039 100
1-063 100 Verbindung 1-063 100 connection
Abutilon theophrasti Beispiel Nr.  Abutilon theophrasti Example no.
1-067 90 1-067 90
1-038 80  1-038 80
1-115 100  1-115 100
1-064 100  1-064 100
1-203 90  1-203 90
1-096 100  1-096 100
1-087 100  1-087 100
1-120 100  1-120 100
1-156 90  1-156 90
1-060 80  1-060 80
1-065 80  1-065 80
1-207 80  1-207 80
1-138 80  1-138 80
1-034 80  1-034 80
Tabelle C4 Table C4
Verbindung connection
Amaranthus retroflexus Beispiel Nr.  Amaranthus retroflexus Example no.
1-205 100 1-205 100
1-126 100  1-126 100
1-093 100  1-093 100
1-091 100  1-091 100
1-158 100  1-158 100
1-094 100  1-094 100
1-095 100  1-095 100
1-044 100  1-044 100
1-133 100  1-133 100
1-069 100  1-069 100
1-134 100  1-134 100
1-135 100  1-135 100
1-062 100 Verbindung 1-062 100 connection
Amaranthus retroflexus Beispiel Nr.  Amaranthus retroflexus Example no.
1-092 100 1-092 100
1-036 90  1-036 90
1-140 100  1-140 100
1-157 100  1-157 100
1-141 100  1-141 100
1-089 100  1-089 100
1-097 90  1-097 90
1-090 100  1-090 100
1-037 100  1-037 100
1-211 100  1-211 100
1-066 100  1-066 100
1-122 100  1-122 100
1-155 100  1-155 100
1-192 80  1-192 80
1-163 90  1-163 90
1-183 100  1-183 100
1-136 100  1-136 100
1-039 100  1-039 100
1-063 100  1-063 100
1-067 100  1-067 100
1-038 100  1-038 100
1-115 100  1-115 100
1-064 100  1-064 100
1-203 100  1-203 100
1-096 100  1-096 100
1-087 100  1-087 100
1-120 80  1-120 80
1-156 100  1-156 100
1-060 100  1-060 100
1-065 100  1-065 100
1-207 100  1-207 100
1-142 90  1-142 90
1-121 100 Verbindung 1-121 100 connection
Amaranthus retroflexus Beispiel Nr.  Amaranthus retroflexus Example no.
1-186 100 1-186 100
1-042 80  1-042 80
1-188 100  1-188 100
1-137 100  1-137 100
1-034 100  1-034 100
1-035 90  1-035 90
1-058 100  1-058 100
1-032 80  1-032 80
Tabelle C5 Table C5
Verbindung connection
Matricaria inodora Beispiel Nr.  Matricaria inodora Example no.
1-205 100 1-205 100
1-126 100  1-126 100
1-093 100  1-093 100
1-091 100  1-091 100
1-158 100  1-158 100
1-094 100  1-094 100
1-095 100  1-095 100
1-044 100  1-044 100
1-133 100  1-133 100
1-069 100  1-069 100
1-134 100  1-134 100
1-135 90  1-135 90
1-062 100  1-062 100
1-092 100  1-092 100
1-036 90  1-036 90
1-140 100  1-140 100
1-157 100  1-157 100
1-141 100  1-141 100
1-089 100 Verbindung 1-089 100 connection
Matricaria inodora Beispiel Nr.  Matricaria inodora Example no.
1-097 1001-097 100
1-090 1001-090 100
1-037 901-037 90
1-211 901-211 90
1-066 1001-066 100
1-122 1001-122 100
1-155 1001-155 100
1-192 1001-192 100
1-163 1001-163 100
1-183 1001-183 100
1-136 1001-136 100
1-039 901-039 90
1-063 1001-063 100
1-067 1001-067 100
1-038 901-038 90
1-115 901-115 90
1-064 901-064 90
1-203 801-203 80
1-096 1001-096 100
1-087 901-087 90
1-156 1001-156 100
1-065 901-065 90
1-186 901-186 90
1-042 901-042 90
1-032 90 1-032 90
Tabelle C6 Table C6
Verbindung connection
Stellaria media Beispiel Nr.  Stellaria media Example no.
1-205 1001-205 100
1-126 100 Verbindung 1-126 100 connection
Stellaria media Beispiel Nr.  Stellaria media Example no.
1-093 1001-093 100
1-091 1001-091 100
1-158 1001-158 100
1-094 1001-094 100
1-095 1001-095 100
1-044 1001-044 100
1-133 1001-133 100
1-069 1001-069 100
1-134 1001-134 100
1-135 1001-135 100
1-062 1001-062 100
1-092 901-092 90
1-036 1001-036 100
1-140 1001-140 100
1-157 1001-157 100
1-141 901-141 90
1-089 1001-089 100
1-097 1001-097 100
1-090 1001-090 100
1-037 1001-037 100
1-211 1001-211 100
1-066 1001-066 100
1-122 1001-122 100
1-155 1001-155 100
1-192 901-192 90
1-163 901-163 90
1-183 1001-183 100
1-136 1001-136 100
1-039 1001-039 100
1-063 901-063 90
1-067 901-067 90
1-038 1001-038 100
1-115 90 Verbindung 1-115 90 connection
Stellaria media Beispiel Nr.  Stellaria media Example no.
1-064 1001-064 100
1-203 801-203 80
1-096 901-096 90
1-120 1001-120 100
1-156 1001-156 100
1-065 1001-065 100
1-207 1001-207 100
1-142 901-142 90
1-121 801-121 80
1-186 1001-186 100
1-042 1001-042 100
1-188 901-188 90
1-137 1001-137 100
1-034 901-034 90
1-058 90 1-058 90
Tabelle C7 Table C7
Verbindung connection
Viola tricolor Beispiel Nr.  Viola tricolor Example no.
1-205 1001-205 100
1-126 1001-126 100
1-093 1001-093 100
1-091 1001-091 100
1-158 1001-158 100
1-094 1001-094 100
1-095 1001-095 100
1-044 1001-044 100
1-133 1001-133 100
1-069 1001-069 100
1-134 1001-134 100
1-135 100 Verbindung 1-135 100 connection
Viola tricolor Beispiel Nr.  Viola tricolor Example no.
1-062 1001-062 100
1-092 901-092 90
1-036 1001-036 100
1-140 1001-140 100
1-157 1001-157 100
1-141 1001-141 100
1-089 1001-089 100
1-097 1001-097 100
1-090 1001-090 100
1-037 1001-037 100
1-211 1001-211 100
1-066 1001-066 100
1-122 1001-122 100
1-155 1001-155 100
1-192 1001-192 100
1-163 1001-163 100
1-183 1001-183 100
1-136 1001-136 100
1-039 1001-039 100
1-063 1001-063 100
1-067 1001-067 100
1-038 1001-038 100
1-115 1001-115 100
1-064 1001-064 100
1-203 901-203 90
1-096 1001-096 100
1-087 1001-087 100
1-120 1001-120 100
1-156 1001-156 100
1-060 1001-060 100
1-065 1001-065 100
1-207 1001-207 100
1-142 100 Verbindung 1-142 100 connection
Viola tricolor Beispiel Nr.  Viola tricolor Example no.
1-121 100 1-121 100
1-138 90  1-138 90
1-186 100  1-186 100
1-042 90  1-042 90
1-188 100  1-188 100
1-137 100  1-137 100
1-034 100  1-034 100
1-035 100  1-035 100
1-058 80  1-058 80
1-160 100  1-160 100
Tabelle C8 Table C8
Verbindung  connection
Polygonum convolvulus Beispiel Nr.  Polygonum convolvulus Example no.
1-205 100  1-205 100
1-126 100  1-126 100
1-093 100  1-093 100
1-091 100  1-091 100
1-158 100  1-158 100
1-094 90  1-094 90
1-095 90  1-095 90
1-044 90  1-044 90
1-133 100  1-133 100
1-069 100  1-069 100
1-134 100  1-134 100
1-135 90  1-135 90
1-062 100  1-062 100
1-092 90  1-092 90
1-140 100  1-140 100
1-157 100 Verbindung 1-157 100 connection
Polygonum convolvulus Beispiel Nr.  Polygonum convolvulus Example no.
1-141 100  1-141 100
1-089 90  1-089 90
1-097 100  1-097 100
1-090 90  1-090 90
1-037 100  1-037 100
1-211 90  1-211 90
1-066 90  1-066 90
1-122 100  1-122 100
1-192 100  1-192 100
1-163 100  1-163 100
1-183 100  1-183 100
1-136 100  1-136 100
1-039 90  1-039 90
1-063 100  1-063 100
1-067 90  1-067 90
1-038 80  1-038 80
1-115 90  1-115 90
1-064 100  1-064 100
1-203 80  1-203 80
1-096 100  1-096 100
1-087 90  1-087 90
1-120 80  1-120 80
1-156 100  1-156 100
1-060 100  1-060 100
1-065 100  1-065 100
1-207 80  1-207 80
1-142 100  1-142 100
1-121 90  1-121 90
1-138 80  1-138 80
1-186 80  1-186 80
1-137 100  1-137 100
1-160 80 Tabelle C9 1-160 80 Table C9
Verbindung  connection
Veronica persica Beispiel Nr.  Veronica persica example no.
1-205 100 1-205 100
1-093 1001-093 100
1-091 1001-091 100
1-158 1001-158 100
1-094 1001-094 100
1-095 1001-095 100
1-044 1001-044 100
1-069 1001-069 100
1-134 1001-134 100
1-135 1001-135 100
1-092 1001-092 100
1-036 1001-036 100
1-157 1001-157 100
1-141 1001-141 100
1-089 1001-089 100
1-097 901-097 90
1-090 1001-090 100
1-037 1001-037 100
1-211 1001-211 100
1-066 1001-066 100
1-122 1001-122 100
1-192 1001-192 100
1-163 901-163 90
1-039 1001-039 100
1-067 1001-067 100
1-115 1001-115 100
1-064 1001-064 100
1-203 1001-203 100
1-096 1001-096 100
1-087 1001-087 100
1-120 1001-120 100
1-060 100 Verbindung 1-060 100 connection
Veronica persica Beispiel Nr.  Veronica persica example no.
1-207 100 1-207 100
1-142 901-142 90
1-121 1001-121 100
1-138 1001-138 100
1-042 1001-042 100
1-160 1001-160 100
1-032 90 1-032 90
Tabelle CIO Table CIO
Verbindung  connection
Avena fatua Beispiel Nr.  Avena fatua example no.
1-205 100 1-205 100
1-126 1001-126 100
1-093 1001-093 100
1-091 901-091 90
1-158 1001-158 100
1-095 1001-095 100
1-044 1001-044 100
1-133 1001-133 100
1-069 1001-069 100
1-134 801-134 80
1-135 801-135 80
1-062 801-062 80
1-092 901-092 90
1-036 901-036 90
1-140 1001-140 100
1-157 1001-157 100
1-141 801-141 80
1-089 801-089 80
1-097 801-097 80
1-090 1001-090 100
1-122 801-122 80
1-155 1001-155 100
1-136 90 Verbindung 1-136 90 connection
Avena fatua Beispiel Nr.  Avena fatua example no.
1-039 90  1-039 90
1-063 100  1-063 100
1-087 80  1-087 80
Tabelle Cl l Table Cl l
Verbindung  connection
Echinochloa crus-galli Beispiel Nr.  Echinochloa crus-galli Example Nr.
1-205 100  1-205 100
1-126 100  1-126 100
1-093 100  1-093 100
1-091 100  1-091 100
1-158 100  1-158 100
1-094 100  1-094 100
1-095 100  1-095 100
1-044 100  1-044 100
1-133 100  1-133 100
1-069 100  1-069 100
1-134 90  1-134 90
1-135 100  1-135 100
1-062 100  1-062 100
1-092 100  1-092 100
1-036 100  1-036 100
1-140 100  1-140 100
1-157 100  1-157 100
1-141 100  1-141 100
1-089 100  1-089 100
1-097 100  1-097 100
1-090 100  1-090 100
1-037 100  1-037 100
1-211 90  1-211 90
1-066 100  1-066 100
1-122 100  1-122 100
1-155 90  1-155 90
1-192 100 Verbindung 1-192 100 connection
Echinochloa crus-galli Beispiel Nr.  Echinochloa crus-galli Example Nr.
1-163 100  1-163 100
1-183 100  1-183 100
1-136 90  1-136 90
1-063 100  1-063 100
1-067 90  1-067 90
1-038 80  1-038 80
1-115 100  1-115 100
1-064 90  1-064 90
1-203 80  1-203 80
1-096 80  1-096 80
1-087 80  1-087 80
1-120 100  1-120 100
1-156 80  1-156 80
1-060 80  1-060 80
1-188 80  1-188 80
Tabelle C12 Table C12
Verbindung  connection
Lolium rigidum Beispiel Nr.  Lolium rigidum Example no.
1-205 100  1-205 100
1-126 100  1-126 100
1-093 100  1-093 100
1-091 90  1-091 90
1-158 100  1-158 100
1-094 80  1-094 80
1-095 100  1-095 100
1-044 90  1-044 90
1-133 100  1-133 100
1-069 100  1-069 100
1-134 100  1-134 100
1-135 90  1-135 90
1-062 80  1-062 80
1-092 100  1-092 100
1-036 100 Verbindung 1-036 100 connection
Lolium rigidum Beispiel Nr.  Lolium rigidum Example no.
1-140 100 1-140 100
1-157 1001-157 100
1-141 901-141 90
1-089 901-089 90
1-090 901-090 90
1-037 1001-037 100
1-211 1001-211 100
1-155 801-155 80
1-183 1001-183 100
1-136 1001-136 100
1-115 80 1-115 80
Tabelle Cl 3 Table Cl 3
Tabelle C14 Table C14
Verbindung  connection
Hordeum murinum Beispiel Nr.  Hordeum murinum Example Nr.
1-205 100 1-205 100
1-126 1001-126 100
1-093 1001-093 100
1-091 1001-091 100
1-158 1001-158 100
1-094 100 Verbindung 1-094 100 connection
Hordeum murinum  Hordeum murinum
Beispiel Nr.  Example no.
1-095 100  1-095 100
1-044 90  1-044 90
1-133 100  1-133 100
1-069 100  1-069 100
1-134 90  1-134 90
1-135 80  1-135 80
1-062 100  1-062 100
1-092 100  1-092 100
1-036 100  1-036 100
1-140 100  1-140 100
1-157 100  1-157 100
1-141 80  1-141 80
1-089 90  1-089 90
1-097 90  1-097 90
1-090 100  1-090 100
1-037 90  1-037 90
1-066 100  1-066 100
1-122 90  1-122 90
1-155 100  1-155 100
1-192 90  1-192 90
1-163 90  1-163 90
1-183 100  1-183 100
1-063 100  1-063 100
Die Versuchsergebnisse belegen, dass erfindungsgemäße Verbindungen der allgemeinen Formel (I) bei Behandlung im Vorauflauf eine gute herbizide Wirksamkeit gegen ausgewählte Schadpflanzen wie z.B. Alopecurus myosuroides, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora, Stellaria media, Viola tricolor, Polygonum convolvulus, Veronica persica, Avena fatua, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Pharbitis purpurea bei einer The test results prove that compounds of the general formula (I) according to the invention, when treated in pre-emergence, have good herbicidal activity against selected harmful plants, such as e.g. Alopecurus myosuroides, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora, Stellaria media, Viola tricolor, Polygonum convolvulus, Veronica persica, Avena fatua, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Pharitis purpurea at one
Aufwandmenge von 1280 g Aktivsubstanz pro Hektar aufweisen. Application rate of 1280 g of active ingredient per hectare.

Claims

Patentansprüche claims
1. Substituierte 3-Heteroaryloxy-lH-pyrazole der allgemeinen Formel (I) oder deren Salze 1. Substituted 3-heteroaryloxy-lH-pyrazoles of the general formula (I) or salts thereof
für Sauerstoff, -S(0)„-, -C(R3)(R4) -, -NR5- oder eine einfache Bindung steht mit n gleich 0, 1 oder 2, für ein gegebenenfalls substituiertes Aryl, Heteroaryl, (C3-Cio)-Cycloalkyl oder (C3- Cio)-Cycloalkenyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist, is oxygen, -S (O) "-, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond is n when n is 0, 1 or 2, for an optionally substituted aryl, heteroaryl, ( C3-Cio) cycloalkyl, or (C3- Cio) cycloalkenyl, where each ring or ring system is optionally substituted with up to 5 substituents from the group R 6,
oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring oder für ein gegebenenfalls substituiertes 8-10-gliedriges bicyclisches, heterocyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1 -5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N- Atome enthalten können, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können; und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR8) und S(=NR8)(=0) gewählt werden können; jeder Ring oder jedes Ringsystem ist optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert, or an optionally substituted 5-7 membered heterocyclic ring or an optionally substituted 8-10 membered bicyclic heterocyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms independently of one another up to 2O - Up to 2 S and up to 5 N atoms can contain up to three carbon atoms independently from the groups C (= 0) and C (= S) can be selected; and the sulfur ring atoms may additionally be selected from the groups S, S (= O), S (= O) 2, S (= NR 8 ), and S (= NR 8 ) (= O); each ring or ring system is optionally substituted with up to 5 substituents from the group R 6 ,
oder für ein 8-10-gliedriges bicyclisches, carbocyclisches Ringsystem steht, das ungesättigt, teilweise gesättigt oder vollständig gesättigt ist, und das mit bis zu 5 Substituenten aus der Gruppe R6 substituiert sein kann, or is an 8-10 membered bicyclic, carbocyclic ring system which is unsaturated, partially saturated or fully saturated, and which may be substituted with up to 5 substituents from the group R 6 ,
und wobei für den Fall, dass A eine einfache Bindung representiert, der Rest Q1 ungleich Imidazol oder 1 ,2,4-Triazol ist; für ein gegebenenfalls substituiertes Heteroaryl steht, wobei jeder Ring optional mit bis zu 4 Substituenten aus der Gruppe R7 substituiert ist, and in the case where A represents a single bond, the radical Q 1 is other than imidazole or 1, 2,4-triazole; is an optionally substituted heteroaryl, each ring optionally being substituted by up to 4 substituents from the group R 7 ,
für Wasserstoff, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)- Hydroxyalkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci- C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl- (Ci-C6)-alkyl, (Ci-C6)-Cycloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Cycloalkylsulfmyl-(Ci-C6)- alkyl, (Ci-C6)-Cycloalkylsulfonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)- alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2- C6)-Haloalkenyl, Tris-[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, Carboxyl, Carboxyl-(Ci-C6)- alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)-Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C8)- Haloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C2-C8)-Alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Dialkylaminocarbonyl-(Ci-C6)- alkyl, (C3-Cio)-Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C8)-Alkylcarbonyloxy-(Ci- C4)-alkyl, (Ci-C8)-Alkoxycarbonyloxy-(Ci-C4)-alkyl, (C3-C6)-Cycloalkoxycarbonyloxy- (Ci-C4)-alkyl, (Ci-C6)-Alkylsulfonyl, (Ci-C6)-Haloalkylsulfonyl, Arylsulfonyl, Phthalimidomethyl steht, is hydrogen, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (Ci-C 8) cyanoalkyl, (Ci-C 8) - hydroxyalkyl, (Ci-C 6) alkoxy (C -C 6) alkyl, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (Ci- C 6) alkylthio (Ci-C 6) alkyl, (Ci-C6) -Alkylsulfmyl - (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkylsulfonyl- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -cycloalkylthio (Ci-C 6 ) -alkyl, (Ci-C6 ) -Cycloalkylsulfmyl- (Ci-C 6) - alkyl, (Ci-C 6) -Cycloalkylsulfonyl- (Ci-C 6) alkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) - alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 8) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) - halocycloalkyl, (C 3 -C 6) -Halocycloalkyl- (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, tris - [(Ci-C6) alkyl ] silyl- (C 2 -C 6 ) -alkynyl, carboxyl, carboxyl- (C 1 -C 6 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -haloalkylcarbonyl, (C 3 -C 8 ) - cycloalkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) -Haloalkoxycarbonyl, (C3-C8) -cycloalkoxycarbonyl, (C 2 -C 8) -alkylaminocarbonyl, (C3-Cio) -Dialkylaminocarbony l, (C3-C 1 0) - cycloalkylaminocarbonyl, (Ci-C8) alkoxycarbonyl (Ci-C6) alkyl, (C 2 -C 8) - Haloalkoxycarbonyl- (Ci-C6) alkyl, (C3- C 8 ) -cycloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 8 ) -alkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 10) -dialkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 6 ) -cycloalkoxycarbonyl- (C 1 -C 6) -alkyl Cio) -Cycloalkylaminocarbonyl- (Ci-C6) alkyl, (Ci-C8) alkylcarbonyloxy (CI-C4) alkyl, (Ci-C 8) alkoxycarbonyloxy (Ci-C4) alkyl, (C3- C 6 ) cycloalkoxycarbonyloxy- (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl, (C 1 -C 6 ) -haloalkylsulfonyl, arylsulfonyl, phthalimidomethyl,
für Wasserstoff, Halogen, Cyano, (Ci-C6)-Alkyl, (Ci-C6)-Haloalkyl, (Ci-C6)- Cyanoalkyl, (Ci-C6)-Hydroxyalkyl, (Ci-C6)-Alkoxy, (Ci-C6)-Haloalkoxy, (Ci-C6)- Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl, for hydrogen, halogen, cyano, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -cyanoalkyl, (C 1 -C 6 ) -hydroxyalkyl, (C 1 -C 6 ) - alkoxy, (Ci-C 6) -haloalkoxy, (Ci-C6) - alkoxy- (Ci-C 6) alkyl, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, aryl ( C 1 -C 6 ) -alkyl,
Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C6)- alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, Tris- [(Ci-C6)-alkyl]silyl-(C2-C6)-alkmyl, Carboxyl, Carboxyl-(Ci-C6)-alkyl, (Ci-C8)- Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, (Ci-Cs)- Alkoxycarbonyl, (Ci-C6)-Alkenyloxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C3-C8)- Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C8)- Haloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C2-C8)-Alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Dialkylaminocarbonyl-(Ci-C6)- alkyl, (C3-Cio)-Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, Amino, (Ci-C6)-Alkylamino, (C2-Cio)-Dialkylamino, (Ci-C6)-Haloalkylamino, (C3-C8)-Cycloalkylamino, (C2-C8)- Alkenylamino, (C4-Cio)-Dialkenylamino, (Ci-C6)-Alkylcarbonylamino, (C2-C10)- (Dialkylcarbonyl)amino, (Ci-C6)-Haloalkylcarbonylamino, (C3-C8)- Cycloalkylcarbonylamino, (N-(Ci-C6)-Alkylcarbonyl)-(Ci-C6)-alkylamino, (CI-CÖ)-Heteroaryl- (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl , (C 3 -C 6) halocycloalkyl, (C 3 C 6) -Halocycloalkyl- (Ci-C 6) - alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, ( C 2 -C 6) haloalkenyl, (C 2 -C 6) haloalkynyl, tris [(Ci-C6) alkyl] silyl (C 2 -C 6) -alkmyl, carboxyl, carboxyl (Ci-C 6) alkyl, (Ci-C 8) - alkylcarbonyl, (Ci-C 8) haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (Ci-Cs) - alkoxycarbonyl, (Ci-C6) alkenyloxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C3-C8) - cycloalkoxycarbonyl, (C2-C8) -alkylaminocarbonyl, (C3-Cio) dialkylaminocarbonyl, (C3-Cio) cycloalkylaminocarbonyl, (Ci-C 8) - alkoxycarbonyl (Ci-C6) alkyl, (C 2 -C 8) - Haloalkoxycarbonyl- (Ci-C6) alkyl, (C3-C8) -Cycloalkoxycarbonyl- (Ci-C6) alkyl, (C2-C8 ) -Alkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 10) -dialkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 10) -cycloalkylaminocarbonyl- (C 1 -C 6) -alkyl, amino, (C 1 -C 6) -alkyl ) -Alkylamino, (C 2 -C 10) -dialkylamino, (C 1 -C 6) -hal oalkylamino, (C3-C8) cycloalkylamino, (C2-C8) - alkenylamino, (C4-Cio) -Dialkenylamino, (Ci-C6) alkylcarbonylamino, (C2-C10) - (dialkylcarbonyl) amino, (Ci- C6) -Haloalkylcarbonylamino, (C3-C8) - Cycloalkylcarbonylamino, (N- (C 1 -C 6) -alkylcarbonyl) - (C 1 -C 6) -alkylamino, (CI-CÖ) -
Alkyl-S(0)x steht, Alkyl-S (0) x is
wobei x gleich 0, 1 oder 2 ist,  where x is 0, 1 or 2,
oder or
R1 und R2 zusammen einen Alkyl-(CH2)m-Ring bilden, wobei m gleich 3, 4 oder 5 ist, R 1 and R 2 together form an alkyl (CH 2 ) m ring where m is 3, 4 or 5,
R3 und R4 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C8)-Alkyl, (Ci-Cs)- Haloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkoxy-(Ci-C6)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfinyl- (Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)- Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy, (Ci-Cg)-Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-C8)-Cycloalkylthio, stehen, oder R 3 and R 4 are independently hydrogen, hydroxy, halogen, (Ci-C 8) -alkyl, (Ci-Cs) - haloalkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) alkynyl , (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 4) -alkyl 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfinyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (Ci-C 8) - haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C4-C8) -cycloalkoxycarbonyl, (C 2 - C 8 ) -alkylaminocarbonyl, (C 3 -C 10) -dialkylaminocarbonyl, (C 3 -C 10) -cycloalkylaminocarbonyl, (C 1 -C 8 ) -alkoxy, (Ci-Cg) -alkylthio, (Ci-Cg) -haloalkylthio, (C 3 -C 8 ) -cycloalkylthio, or
R3 und R4 gemeinsam einen 3- bis 6-gliedrigen carbocyclischen Ring oder einen 3- bis 6- gliedrigen gesättigten heterocyclischen Ring mit bis zu 2 Sauerstoffatomen bilden, oder R 3 and R 4 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms, or
R3 und R4 gemeinsam einen (Ci-C3)-Alkylidenrest oder (Ci-C3)-Haloalkylidenrest bilden, R 3 and R 4 together form a (C 1 -C 3 ) -alkylidene radical or (C 1 -C 3) -haloalkylidene radical,
R5 für Wasserstoff, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci- C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)- Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C6)-alkyl, (C2-C8)-Alkenyl, (C2-C8)- Alkinyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)- Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfmyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl- (Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Formyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)-Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-C10)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl steht, R 5 represents hydrogen, (Ci-C 8) -alkyl, (Ci-C8) haloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci- C6) alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) - halocycloalkyl, (C 3 C 6) -Halocycloalkyl- (Ci-C 6) alkyl , (C 2 -C 8) alkenyl, (C 2 -C 8) - alkynyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) haloalkoxy (C -C 8) alkyl, (Ci-C 8) - alkylthio (Ci-C8) alkyl, (Ci-C 8) -Alkylsulfmyl- (Ci-C 8) alkyl, (Ci-C 8) - alkylsulfonyl (Ci-C 8) alkyl, (Ci-C 8) alkylcarbonyl, (Ci-C 8) haloalkylcarbonyl, (C 3 -C 8) - cycloalkylcarbonyl, formyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) -Haloalkoxycarbonyl, (C4-C8) -cycloalkoxycarbonyl, (C2-C8) -alkylaminocarbonyl, (C3-C10) - alkylaminocarbonyl, (C3-Cio) cycloalkylaminocarbonyl group,
R6 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl,R 6 represents hydrogen, halogen, cyano, nitro, formyl, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl,
(C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C5)-Haloalkinyl, (C1-C4)- Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)- alkyl, (Ci-C8)-Alkylsulfmyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)- Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-Cs)- Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)-Alkylsulfmyl, (Ci-C8)-Haloalkylsulfmyl, (C3-C8)-Cycloalkylsulfmyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)- Haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-C8)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 5 ) haloalkynyl, (C 1 -C 4 ) - Alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (Ci-C8) alkylthio (Ci-C8) - alkyl, (Ci- C 8 ) -alkylsulfmyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, carboxy, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C 4 -C 8) - cycloalkoxycarbonyl, (C2-C8) alkylaminocarbonyl, (C 3 -C 10) -dialkylaminocarbonyl, (C 3 -C 10) -cycloalkylaminocarbonyl, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -haloalkoxy, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkylthio , (C 3 -C 8) -cycloalkylthio, (Ci-C 8) -Alkylsulfmyl, (Ci-C 8) -Haloalkylsulfmyl, (C 3 -C 8) -Cycloalkylsulfmyl, (Ci-C8) alkylsulfonyl, (C -C 8) - haloalkylsulfonyl, (C3-C8) cycloalkylsulfonyl, (Ci-C 8) alkylaminosulfonyl, (C 2 -C 8) - dialkylaminosulphonyl or (C3-C 8) is trialkylsilyl,
R7 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (C2-C8) Alkenyl, (C2-C4)-Haloalkenyl, (C2-C5)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)- Alkylsulfmyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)-Alkylsulfmyl, (Ci-C8)-Haloalkylsulfmyl, (C3-C8)- Cycloalkylsulfmyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, (C3-C8)- cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-C8)-Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, R 7 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 5) haloalkynyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (Ci-C 8) alkylthio (Ci-C8) alkyl, (Ci-C 8) - Alkylsulfmyl- (Ci-C 8) alkyl, (Ci-C8) alkylsulfonyl (Ci-C 8) alkyl, (Ci-C 8) - alkylcarbonyl, (Ci-C 8) haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, carboxy, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C 4 -C 8) -cycloalkoxycarbonyl, (C 2 -C 8) -alkylaminocarbonyl, (C3-Cio) dialkylaminocarbonyl, (C3-C 1 0) - cycloalkylaminocarbonyl, (Ci-C 8) alkoxy, (Ci-C 8 ) alkylthio, (Ci-C8) haloalkylthio, (C 3 -C 8) -cycloalkylthio, (Ci-C 8) -Alkylsulfmyl, (Ci-C 8) -Haloalkylsulfmyl, (C 3 -C 8) - Cycloalkylsulfmyl , (Ci-C8) alkylsulfonyl, (Ci-C 8) haloalkylsulfonyl, (C 3 -C 8) - cycloalkylsulfonyl, (Ci-C 8) alkylaminosulfonyl, (C 2 -C 8) dialkylaminosulfonyl, or (C 3 -C 8 ) -trialkylsilyl ste ht,
R8 für Wasserstoff, Amino, Hydroxy, Cyano, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-Hydroxyalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Aryl- (Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-C10)- Cycloalkyl, (C3-Cio)-Cycloalkyl-(Ci-C8)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)- Halocycloalkyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C2-Cg) Alkenyl, (C2-C8)-Alkinyl, Tris-[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, Tris-[(Ci-C8)- alkyljsilyl steht. R 8 represents hydrogen, amino, hydroxyl, cyano, formyl, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -cyanoalkyl, (C 1 -C 8 ) -hydroxyalkyl, ( C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C3-C10) - cycloalkyl, (C 3 -Cio) cycloalkyl- (Ci-C 8) alkyl, (C 3 -C 8) halocycloalkyl, (C 3 -C 8) - Halocycloalkyl- (Ci-C 8) alkyl, (Ci-C 8) alkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 2 -CG) alkenyl, (C 2 -C 8) -alkynyl, tris - [(Ci-C 8) alkyl] silyl (C 2 -C 8) -alkynyl, tris - alkyljsilyl is - [(Ci-C 8).
Verbindung der allgemeinen Formel (I) nach Anspruch 1 oder deren Salze, worin A compound of general formula (I) according to claim 1 or its salts, wherein
A für Sauerstoff, -S(0)„-, -C(R3)(R4) -, -NR5- oder eine einfache Bindung steht, wobei n gleich 0, 1 oder 2 ist, A is oxygen, -S (O) "-, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond, where n is 0, 1 or 2,
Q1 für ein gebenenfalls substituiertes Aryl, Heteroaryl, (C3-Cio)-Cycloalkyl oder (C3-C10)- Cycloalkenyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist, Q 1 is an optionally substituted aryl, heteroaryl, (C 3 -C 10) -cycloalkyl or (C 3 -C 10) -cycloalkenyl, each ring or ring system being optionally substituted with up to 5 substituents from the group R 6 ,
oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring, oder für ein gegebenenfalls substituiertes 8-10-gliedriges bicyclisches, heterocyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N- Atome enthalten können, besteht und wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR8) und S(=NR8)(=0) gewählt werden können;, or an optionally substituted 5-7 membered heterocyclic ring, or an optionally substituted 8-10 membered bicyclic heterocyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms independently of one another up to 2 O, up to 2 S and up to 5 N atoms may contain, and wherein up to three carbon ring atoms independently from the groups C (= 0) and C (= S) can be selected and the sulfur ring atoms in addition from the Groups S, S (= 0), S (= 0) 2, S (= NR 8 ) and S (= NR 8 ) (= 0) can be selected ;,
jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist, each ring or ring system is optionally substituted with up to 5 substituents from the group R 6 ,
oder für ein 8-10-gliedriges bicyclisches, carbocyclisches Ringsystem steht, das ungesättigt, teilweise gesättigt oder vollständig gesättigt ist, und das mit bis zu 5 Substituenten aus der Gruppe R6 substituiert sein kann, or is an 8-10 membered bicyclic, carbocyclic ring system which is unsaturated, partially saturated or fully saturated, and which may be substituted with up to 5 substituents from the group R 6 ,
und wobei für den Fall, dass A eine einfache Bindung ist, der Rest Q1 ungleich Imidazol oder 1 ,and in the case where A is a single bond, the radical Q 1 is different from imidazole or 1,
2,4-Triazol ist, 2,4-triazole is,
Q2 für die Gruppen Q- 1 bis Q- 10 steht Q 2 stands for the groups Q-1 to Q-10
Q-l Q-2 Q-3 Q-4 Q-5 Q-1 Q-2 Q-3 Q-4 Q-5
Q-6 Q-7 Q-8 Q-9 Q-10  Q-6 Q-7 Q-8 Q-9 Q-10
R1 für Wasserstoff, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-R 1 represents hydrogen, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (Ci-C 8) cyanoalkyl, (Ci-C 8) -
Hydroxyalkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci- C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl- (Ci-C6)-alkyl, (Ci-C6)-Cycloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Cycloalkylsulfmyl-(Ci-C6)- alkyl, (Ci-C6)-Cycloalkylsulfonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)- alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2- C6)-Haloalkenyl, Tris-[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, Carboxyl, Carboxyl-(Ci-C6)- alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-Cg)-Cycloalkylcarbonyl, (Ci-Cg)-Alkoxycarbonyl, (C2-Cg)-Haloalkoxycarbonyl, (C3-Cg)-Cycloalkoxycarbonyl, (C2-Cg)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-Cg)-Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-Cg)- Haloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-Cg)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C2-Cg)-Alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Dialkylaminocarbonyl-(Ci-C6)- alkyl, (C3-Cio)-Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-Cg)-Alkylcarbonyloxy-(Ci- C4)-alkyl, (Ci-Cg)-Alkoxycarbonyloxy-(Ci-C4)-alkyl, (C3-C6)-Cycloalkoxycarbonyloxy- (Ci-C4)-alkyl, (Ci-C6)-Alkylsulfonyl, (Ci-C6)-Haloalkylsulfonyl, Arylsulfonyl, Phthalimidomethyl steht, für Wasserstoff, Halogen, Cyano, (Ci-C6)-Alkyl, (Ci-C6)-Haloalkyl, (Ci-C6)-Hydroxyalkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (ci) C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfmyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (Ci-C 6) alkyl, (Ci-C 6) cycloalkylthio (Ci-C 6) alkyl, (Ci-C6) -Cycloalkylsulfmyl- (Ci-C 6) - alkyl, (Ci-C 6) -Cycloalkylsulfonyl- (Ci-C 6) alkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) - alkyl, heterocyclyl- (Ci-C 6) alkyl, (C 3 -C 8) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) -Halocycloalkyl- (Ci-C 6) alkyl , (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, tris - [(Ci-C6) alkyl] silyl (C2-C6) alkynyl, carboxyl, carboxyl (CI- C 6 ) -alkyl, (C 1 -C 8) -alkylcarbonyl, (C 1 -C 8) -haloalkylcarbonyl, (C 3 -C 9) -cycloalkylcarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 2 -Cg) -haloalkoxycarbonyl, (C 3 -C 4) -haloalkylcarbonyl, Cg) -cycloalkoxycarbonyl, (C 2 -Cg) -alkylaminocarbonyl, (C 3 -C 10) -dialkylaminocarbonyl, (C 3 -C 10) -cycloalkylaminocarbonyl, (Ci-Cg) -alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -Cg) - haloalkoxycarbonyl- (Ci-C6) -alkyl, (C3-Cg) -cycloalkoxycarbonyl- (Ci-C6) -alkyl, (C2-Cg) -alkylaminocarbonyl- (Ci-C6) -alkyl, (C3- Cio) -Dialkylaminocarbonyl- (Ci-C6) - alkyl, (C3-Cio) -Cycloalkylaminocarbonyl- (Ci -C6) alkyl, (Ci-Cg) -Alkylcarbonyloxy- (Ci-C4) -alkyl, (Ci-Cg) -Alkoxycarbonyloxy- (Ci-C4) -alkyl, (C3-C6) -Cycloalkoxycarbonyloxy- (Ci-C 4 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl, (C 1 -C 6 ) -haloalkylsulfonyl, arylsulfonyl, phthalimidomethyl, represents hydrogen, halogen, cyano, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) Haloalkyl, (Ci-C 6 ) -
Cyanoalkyl, (Ci-C6)-Hydroxyalkyl, (Ci-C6)-Alkoxy, (Ci-C6)-Haloalkoxy, (Ci-C6)- Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl, Cyanoalkyl, (Ci-C 6) hydroxyalkyl, (Ci-C 6) alkoxy, (Ci-C 6) -haloalkoxy, (Ci-C6) - alkoxy- (Ci-C 6) alkyl, (Ci- C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl,
Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C6)- alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkmyl, Tris- [(Ci-C6)-alkyl]silyl-(C2-C6)-alkmyl, Carboxyl, Carboxyl-(Ci-C6)-alkyl, (Ci-Cg)- Alkylcarbonyl, (Ci-Cg)-Haloalkylcarbonyl, (C3-Cg)-Cycloalkylcarbonyl, (Ci-Cg)- Alkoxycarbonyl, (Ci-C6)-Alkenyloxycarbonyl, (C2-Cg)- Haloalkoxycarbonyl, (C3-Cg)- Cycloalkoxycarbonyl, (C2-Cg)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-Cg)-Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-Cg)- Haloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-Cg)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C2-Cg)-Alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-Cio)-Dialkylaminocarbonyl-(Ci-C6)- alkyl, (C3-Cio)-Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, Amino, (Ci-C6)-Alkylamino, (C2-Cio)-Dialkylamino, (Ci-C6)-Haloalkylamino, (C3-Cg)-Cycloalkylamino, (C2-Cg)- Alkenylamino, (C4-Cio)-Dialkenylamino, (Ci-C6)-Alkylcarbonylamino, (C2-C10)- (Dialkylcarbonyl)amino, (Ci-C6)-Haloalkylcarbonylamino, (C3-Cg)- Cycloalkylcarbonylamino, (N-(Ci-C6)-Alkylcarbonyl)-(Ci-C6)-alkylamino,(Ci-C6)- Alkyl-S(0)x steht, wobei x gleich 0, 1 oder 2 ist, R1 und R2 zusammen einen Alkyl-(CH2)m-Ring bilden, wobei m gleich 3, 4 oder 5 ist, Heteroaryl- (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl , (C 3 -C 6) halocycloalkyl, (C 3 C 6) -Halocycloalkyl- (Ci-C 6) - alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, ( C 2 -C 6) haloalkenyl, (C 2 -C 6) -Haloalkmyl, tris [(Ci-C6) alkyl] silyl (C 2 -C 6) -alkmyl, carboxyl, carboxyl (Ci-C 6 ) -alkyl, (Ci-Cg) - alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C3-Cg) -cycloalkylcarbonyl, (Ci-Cg) - alkoxycarbonyl, (Ci-C6) -alkenyloxycarbonyl, (C 2 -Cg ) - haloalkoxycarbonyl, (C3-Cg) - cycloalkoxycarbonyl, (C 2 -Cg) -alkylaminocarbonyl, (C3-Cio) -dialkylaminocarbonyl, (C3-Cio) -cycloalkylaminocarbonyl, (Ci-Cg) -alkoxycarbonyl- (Ci-C6) -alkyl, (C 2 -Cg) - haloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 9) -cycloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 8) -alkylaminocarbonyl- (C 1 -C 6) - alkyl, (C 3 -C 10) -dialkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 10) -cycloalkylaminocarbonyl- (C 1 -C 6) -alkyl, amino, (C 1 -C 6) -alkylamino, (C 2 -C 10) -alkyl Dialkylamino, (Ci-C6) -haloalkylamino, (C3-Cg) - Cycloalkylamino, (C 2 -C 9) -alkenylamino, (C 4 -C 10) -dialkenylamino, (C 1 -C 6) -alkylcarbonylamino, (C 2 -C 10) - (dialkylcarbonyl) -amino, (C 1 -C 6) -haloalkylcarbonylamino, (C 3 -Cg) - cycloalkylcarbonylamino, (N- (C 1 -C 6) -alkylcarbonyl) - (C 1 -C 6) -alkylamino, (C 1 -C 6) -alkyl-S (O) x , where x is 0, 1 or 2, R 1 and R 2 together form an alkyl (CH 2) m ring, where m is 3, 4 or 5,
R3 und R4 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C8)-Alkyl, (Ci-Cs)- Haloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkoxy-(Ci-C6)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfinyl- (Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)- Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy, (Ci-Cg)-Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-C8)-Cycloalkylthio, stehen, oder R 3 and R 4 are independently hydrogen, hydroxy, halogen, (Ci-C 8) -alkyl, (Ci-Cs) - haloalkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) alkynyl , (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 4) -alkyl 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfinyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (Ci-C 8) - haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C4-C8) -cycloalkoxycarbonyl, (C2-C 8 ) -alkylaminocarbonyl, (C 3 -C 10) -dialkylaminocarbonyl, (C 3 -C 10) -cycloalkylaminocarbonyl, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkylthio, (C 1 -C 6) -haloalkylthio, (C 3 - C 8 ) -cycloalkylthio, or
R3 und R4 zusammen einen 3- bis 6-gliedrigen carbocyclischen Ring oder einen 3- bis 6- gliedrigen gesättigten heterocyclischen Ring mit bis zu 2 Sauerstoffatomen bilden; oder R 3 and R 4 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms; or
R3 und R4 zusammen einen (Ci-C3)-Alkylidenrest oder R 3 and R 4 together form a (C 1 -C 3 ) -alkylidene radical or
(Ci-C3)-Haloalkylidenrest bilden, Form (C 1 -C 3) -haloalkylidene radicals,
R5 für Wasserstoff, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci- C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)- Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C6)-alkyl, (C2-C8)-Alkenyl, (C2-C8)- Alkinyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)- Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfmyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl- (Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Formyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)-Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-C10)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl steht, R 5 represents hydrogen, (Ci-C 8) -alkyl, (Ci-C8) haloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci- C6) alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) - halocycloalkyl, (C 3 C 6) -Halocycloalkyl- (Ci-C 6) alkyl , (C 2 -C 8) alkenyl, (C 2 -C 8) - alkynyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) haloalkoxy (C -C 8) alkyl, (Ci-C 8) - alkylthio (Ci-C8) alkyl, (Ci-C 8) -Alkylsulfmyl- (Ci-C 8) alkyl, (Ci-C 8) - alkylsulfonyl (Ci-C 8) alkyl, (Ci-C 8) alkylcarbonyl, (Ci-C 8) haloalkylcarbonyl, (C 3 -C 8) - cycloalkylcarbonyl, formyl, (Ci-C8) alkoxycarbonyl, (C2-C8) -Haloalkoxycarbonyl, (C4-C8) -cycloalkoxycarbonyl, (C2-C8) -alkylaminocarbonyl, (C3-C10) - alkylaminocarbonyl, (C3-Cio) cycloalkylaminocarbonyl group,
R6 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl,R 6 represents hydrogen, halogen, cyano, nitro, formyl, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl,
(C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C5)-Haloalkinyl, (C1-C4)- Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)- alkyl, (Ci-C8)-Alkylsulfmyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (C2-C8)- Haloalkoxycarbonyl, (C4-C8)-Cycloalkoxycarbonyl, (C2-C8)-Alkylaminocarbonyl, (C3-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-Cg)-Alkoxy, (Ci-Cg)-Haloalkoxy, (Ci-Cg)-Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-Cg)-Cycloalkylthio, (Ci-Cg)-Alkylsulfmyl, (Ci-Cg)- Haloalkylsulfmyl, (C3-Cg)-Cycloalkylsulfmyl, (Ci-Cg)-Alkylsulfonyl, (Ci-Cg)- Haloalkylsulfonyl, (C3-Cg)-Cycloalkylsulfonyl, (Ci-Cg)-Alkylaminosulfonyl, (C2-Cg)- Dialkylaminosulfonyl oder (C3-Cg)-Trialkylsilyl steht, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 4 ) -haloalkenyl, (C 2 -C 5 ) -haloalkynyl, (C 1 -C 4 ) -alkoxy- (Ci -C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (Ci-C (8) alkylthio Ci-C 8) - alkyl, (Ci-C 8) - Alkylsulfmyl- (Ci-C 8) alkyl, (Ci-C8) alkylsulfonyl (Ci-C 8) alkyl, (Ci-C 8) - alkylcarbonyl, (Ci-C 8) haloalkylcarbonyl, (C3- C8) cycloalkylcarbonyl, carboxy, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C4-C8) -cycloalkoxycarbonyl, (C 2 -C 8) -alkylaminocarbonyl, (C 3 -C 10) -dialkylaminocarbonyl, (C 3 -C 10) -cycloalkylaminocarbonyl, (C 1 -C 6) -alkoxy, (C 1 -C 6) -haloalkoxy, (C 1 -C 8) -alkylthio, (Ci -Cg) -haloalkylthio, (C 3 -Cg) -cycloalkylthio, (Ci-Cg) -alkylsulfmyl, (Ci-Cg) - haloalkylsulfmyl, (C 3 -Cg) -cycloalkylsulfmyl, (Ci-Cg) -alkylsulfonyl, (Ci -Cg) - haloalkylsulfonyl, (C3-Cg) -cycloalkylsulfonyl, (Ci-Cg) -alkylaminosulfonyl, (C 2 -Cg) - dialkylaminosulfonyl or (C3-Cg) -trialkylsilyl,
R8 für Wasserstoff, Amino, Hydroxy, Cyano, Formyl, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl, (Ci-Cg)-Cyanoalkyl, (Ci-Cg)-Hydroxyalkyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-alkyl, Aryl- (Ci-Cg)-alkyl, Heteroaryl-(Ci-Cg)-alkyl, Heterocyclyl-(Ci-Cg)-alkyl, (C3-C10)- Cycloalkyl, (C3-Cio)-Cycloalkyl-(Ci-Cg)-alkyl, (C3-Cg)-Halocycloalkyl, (C3-Cg)- Halocycloalkyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)-Alkoxycarbonyl, (C2-Cg)- Alkenyl, (C2-Cg)-Alkinyl, Tris-[(Ci-Cg)-alkyl]silyl-(C2-Cg)-alkinyl, Tris-[(Ci-Cg)- alkyljsilyl steht, R 8 represents hydrogen, amino, hydroxyl, cyano, formyl, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl, (C 1 -C 8) -cyanoalkyl, (C 1 -C 8) -hydroxyalkyl, (C 1 -C 4) Alkoxy- (Ci-Cg) -alkyl, aryl- (Ci-Cg) -alkyl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-Cg) -alkyl, (C3-C10) -cycloalkyl, ( C 3 -C 10) -cycloalkyl- (Ci-Cg) -alkyl, (C 3 -Cg) -halocycloalkyl, (C 3 -Cg) -halocycloalkyl- (Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) alkoxycarbonyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, tris - [(Ci-Cg) alkyl] silyl (C 2 -Cg) alkynyl, tris [(Ci-Cg) - alkyl] silyl,
R9, R10, R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl, (C2-Cg)-Alkenyl, (C2-C4)-Haloalkenyl, (C2-C5)- Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-Cg)- Alkylthio-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylsulfmyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylsulfonyl- (Ci-Cg)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)-Haloalkylcarbonyl, (C3-Cg)- Cycloalkylcarbonyl, Carboxyl, (Ci-Cg)-Alkoxycarbonyl, (C2-Cg)- Haloalkoxycarbonyl, (C4-Cg)-Cycloalkoxycarbonyl, (C2-Cg)-Alkylaminocarbonyl, (C3-C10)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-Cg)-Alkoxy, (Ci-Cg)- Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-Cg)-Cycloalkylthio, (Ci-Cg)-Alkylsulfmyl, (Ci-Cg)-Haloalkylsulfmyl, (C3-Cg)-Cycloalkylsulfmyl, (Ci-Cg)-Alkylsulfonyl, (Ci-Cg)- Haloalkylsulfonyl, (C3-Cg)-cycloalkylsulfonyl, (Ci-Cg)-Alkylaminosulfonyl, (C2-Cg)- Dialkylaminosulfonyl oder (C3-Cg)-Trialkylsilyl steht. R 9 , R 10 , R 11 and R 12 independently of one another represent hydrogen, halogen, cyano, nitro, formyl, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl, (C 2 -C 6) -alkenyl, ( C 2 -C 4) haloalkenyl, (C2-C5) - haloalkynyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) -alkyl, (Ci-Cg) - alkylthio (Ci-Cg) -alkyl, (Ci-Cg) -alkylsulfmyl (Ci-Cg) -alkyl, (Ci-Cg) -alkylsulfonyl- (Ci-Cg) -alkyl , (Ci-Cg) -alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C 3 -Cg) -cycloalkylcarbonyl, carboxyl, (Ci-Cg) -alkoxycarbonyl, (C 2 -Cg) -haloalkoxycarbonyl, (C 4 -Cg ) -Cycloalkoxycarbonyl, (C 2 -C 9) -alkylaminocarbonyl, (C 3 -C 10) -dialkylaminocarbonyl, (C 3 -C 10) -cycloalkylaminocarbonyl, (C 1 -C 6) -alkoxy, (C 1 -C 6) -alkylthio, (C 1 -C 8) Haloalkylthio, (C 3 -C 6) -cycloalkylthio, (C 1 -C 6) -alkylsulfmyl, (C 1 -C 6) -haloalkylsulfmyl, (C 3 -C 6) -cycloalkylsulfmyl, (C 1 -C 8) -alkylsulfonyl, (C 1 -C 8) - Haloalkylsulfonyl, (C3-Cg) -cycloalkylsulfonyl, (Ci-Cg) -alkylaminosulfonyl, (C 2 -Cg) -dialkylaminosulfonyl or (C3-Cg) -trialkylsilyl.
Verbindung der allgemeinen Formel (I) nach Anspruch 1 oder deren Salze, worin A für Sauerstoff, Schwefel, -C(R3)(R4) -, -NR5- oder eine einfache Bindung steht, A compound of the general formula (I) according to claim 1 or salts thereof, in which A is oxygen, sulfur, -C (R 3 ) (R 4 ) -, -NR 5 - or a simple bond,
Q1 für ein gegebnenfalls substituiertes Aryl oder Heteroaryl steht, wobei jeder Ring Q 1 is an optionally substituted aryl or heteroaryl, each ring
optional mit bis zu 5 Substituenten aus der Gruppe R6 substituiert ist, und wobei für den Fall, dass A eine einfache Bindung ist, der Rest Q1 ungleich Imidazol oder 1 ,2,4-Triazol ist, für die Gruppen Q-l 1 bis Q-14 steht, optionally substituted with up to 5 substituents from the group R 6 , and in the case where A is a single bond, the radical Q 1 is other than imidazole or 1, 2,4-triazole, groups Ql 1 to Q-14,
Q-l l Q-12 Q-13 Q-14 Q-1 Q-12 Q-13 Q-14
R1 für Wasserstoff, Methyl, Ethyl, Isopropyl, (Ci-C2)-Haloalkyl, Cyanomethyl, (Ci-C4)- Alkoxy-(Ci-C2)-alkyl, (Ci-C4)-Alkylthio-(Ci-C2)-alkyl, (Ci-C4)-Alkylsulfinyl-(Ci-C2)- alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C2)-alkyl, Arylmethyl, (C2-C6)-Alkenyl, (Ci-C6)- Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (Ci-C6)-Alkoxycarbonyloxy-(Ci-C2)- alkyl, (Ci-C6)-Alkylcarbonyloxy-(Ci-C2)-alkyl steht, R 1 represents hydrogen, methyl, ethyl, isopropyl, (Ci-C 2) haloalkyl, cyanomethyl, (Ci-C4) - alkoxy- (Ci-C 2) alkyl, (Ci-C 4) alkylthio ( Ci-C 2) alkyl, (Ci-C 4) alkylsulfinyl (Ci-C 2) - alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 2) alkyl, arylmethyl, (C 2 - C 6) alkenyl, (Ci-C6) - alkoxycarbonyl, (C3-C6) cycloalkoxycarbonyl, (Ci-C6) alkoxycarbonyloxy (Ci-C 2) - alkyl, (Ci-C6) alkylcarbonyloxy (C -C 2 ) -alkyl,
R2 für Wasserstoff, Halogen, Cyano, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-R 2 is hydrogen, halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -
Cyanoalkyl, (Ci-C4)-Hydroxyalkyl, (Ci-C3)-Alkoxy-(Ci-C4)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C4)-alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C2-C4)- Haloalkenyl, (C2-C4)-Haloalkinyl, (Ci-C6)-Alkoxycarbonyl, (Ci-Ce)- Alkenyloxycarbonyl, (C2-C6)-Haloalkoxycarbonyl, (Ci-C6)-Alkoxycarbonyl-(Ci-C4)- alkyl, (C2-C6)-Haloalkoxycarbonyl-(Ci-C4)-alkyl, Amino, (Ci-C4)-Alkylamino, (C2-Ce)- Dialkylamino, (C2-C4)-Alkenylamino, (Ci-C4)-Alkylcarbonylamino, steht, oder Cyanoalkyl, (Ci-C 4) hydroxyalkyl, (Ci-C 3) alkoxy (Ci-C 4) alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -cycloalkyl- ( Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -alkynyl, (C 2 -C 4) - haloalkenyl, (C 2 -C 4) haloalkynyl, (C C6) alkoxycarbonyl, (Ci-Ce) - alkenyloxycarbonyl, (C 2 -C 6) -Haloalkoxycarbonyl, (Ci-C6) alkoxycarbonyl (Ci-C4) - alkyl, (C 2 -C 6) -Haloalkoxycarbonyl- ( Ci-C 4) alkyl, amino, (Ci-C4) alkylamino, (C2 -Ce) - dialkylamino, (C 2 -C 4) -alkenylamino, (Ci-C4) alkylcarbonylamino, stands, or
R1 und R2 gemeinsam einen Alkyl-(CH2)m-ring bilden, wobei m gleich 3 oder 4 ist, R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, Methyl oder Ethyl steht, R5 für Wasserstoff, Methyl, Ethyl, Formyl oder Acetyl steht, R 1 and R 2 together form an alkyl (CH 2 ) m ring, where m is 3 or 4, R 3 and R 4 independently of one another are hydrogen, halogen, methyl or ethyl, R 5 is hydrogen, methyl, Ethyl, formyl or acetyl,
R6 für Wasserstoff, Halogen, Cyano, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C3)-Alkoxy, (Ci-C3)-Haloalkoxy, Methyl-S(0)n steht, wobei n gleich 0, 1 oder 2 sein kann, R 6 is hydrogen, halogen, cyano, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C 3) alkoxy, (Ci-C 3) -haloalkoxy, methyl-S (0 ) n , where n can be 0, 1 or 2,
R für Wasserstoff, Halogen, Cyano, Methyl, Trifluormethyl, Methoxy steht. R is hydrogen, halogen, cyano, methyl, trifluoromethyl, methoxy.
4. Herbizide Mittel, gekennzeichnet durch einen herbizid wirksamen Gehalt an mindestens einer Verbindung der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3. 4. A herbicidal composition, characterized by a herbicidally active content of at least one compound of the general formula (I) according to one of claims 1 to 3.
5. Herbizide Mittel nach Anspruch 4 in Mischung mit Formulierungshilfsmitteln. 5. A herbicidal composition according to claim 4 in admixture with formulation auxiliaries.
6. Herbizide Mittel nach Anspruch 4 oder 5 enthaltend mindestens einen weiteren pestizid 6. A herbicidal composition according to claim 4 or 5 containing at least one further pesticide
wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und Wachstumsregulatoren.  active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
7. Herbizide Mittel nach Anspruch 6 enthaltend einen Safener. 7. A herbicidal composition according to claim 6 containing a safener.
8. Herbizide Mittel nach Anspruch 7 enthaltend Cyprosulfamid, Cloquintocet-mexyl, Mefenpyr- diethyl oder Isoxadifen-ethyl. 8. A herbicidal composition according to claim 7 containing cyprosulfamide, Cloquintocet-mexyl, Mefenpyr- diethyl or isoxadifen-ethyl.
9. Herbizide Mittel nach einem der Ansprüche 4 bis 8 enthaltend ein weiteres Herbizid. 9. A herbicidal composition according to any one of claims 4 to 8 containing a further herbicide.
10. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge mindestens einer Verbindung der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3 oder eines herbiziden Mittels nach einem der Ansprüche 4 bis 9 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 10. A method for controlling undesirable plants, characterized in that an effective amount of at least one compound of general formula (I) according to any one of claims 1 to 3 or a herbicidal composition according to any one of claims 4 to 9 on the plants or on the place of undesired plant growth.
11. Verwendung von Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach einem der Ansprüche 4 bis 9 zur Bekämpfung unerwünschter Pflanzen. 11. Use of compounds of general formula (I) according to any one of claims 1 to 3 or of herbicidal compositions according to any one of claims 4 to 9 for controlling unwanted plants.
12. Verwendung nach Anspruch 11, dadurch gekennzeichnet, daß die Verbindungen der 12. Use according to claim 11, characterized in that the compounds of
allgemeinen Formel (I) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden.  general formula (I) for controlling undesirable plants in crops of crops.
13. Verwendung nach Anspruch 12, dadurch gekennzeichnet, daß die Nutzpflanzen transgene Nutzpflanzen sind. 13. Use according to claim 12, characterized in that the crops are transgenic crops.
EP18737304.8A 2017-07-18 2018-07-12 Substituted 3-heteroaryloxy-1h-pyrazoles and salts thereof and their use as herbicidal active substances Withdrawn EP3655402A1 (en)

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Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220135537A1 (en) * 2019-02-20 2022-05-05 Sumitomo Chemical Company, Limited Ether compound and harmful arthropod-controlling composition containing same
GB202011068D0 (en) * 2020-07-17 2020-09-02 Syngenta Crop Protection Ag Improvements in or relating to organic compounds
WO2023112033A2 (en) * 2021-12-15 2023-06-22 Adama Agan Ltd. Compounds useful for the preparation of various agrochemicals and markers thereof

Family Cites Families (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MA19709A1 (en) 1982-02-17 1983-10-01 Ciba Geigy Ag APPLICATION OF QUINOLEIN DERIVATIVES TO THE PROTECTION OF CULTIVATED PLANTS.
ATE103902T1 (en) 1982-05-07 1994-04-15 Ciba Geigy Ag USE OF QUINOLINE DERIVATIVES TO PROTECT CROPS.
DE3334799A1 (en) 1983-09-26 1985-04-04 Bayer Ag, 5090 Leverkusen 1,3-DIARYL-5-METHYLENE PERHYDROPYRIMIDINE-2-ONE
DE3525205A1 (en) 1984-09-11 1986-03-20 Hoechst Ag, 6230 Frankfurt PLANT PROTECTIVE AGENTS BASED ON 1,2,4-TRIAZOLE DERIVATIVES AND NEW DERIVATIVES OF 1,2,4-TRIAZOLE
DE3680212D1 (en) 1985-02-14 1991-08-22 Ciba Geigy Ag USE OF CHINOLINE DERIVATIVES FOR PROTECTING CROPS.
DE3633840A1 (en) 1986-10-04 1988-04-14 Hoechst Ag PHENYLPYRAZOLIC CARBONIC ACID DERIVATIVES, THEIR PRODUCTION AND USE AS PLANT GROWTH REGULATORS AND SAFENERS
US5078780A (en) 1986-10-22 1992-01-07 Ciba-Geigy Corporation 1,5-diphenylpyrazole-3-carboxylic acid derivatives for the protection of cultivated plants
DE3808896A1 (en) 1988-03-17 1989-09-28 Hoechst Ag PLANT PROTECTION AGENTS BASED ON PYRAZOL CARBON SEA DERIVATIVES
DE3817192A1 (en) 1988-05-20 1989-11-30 Hoechst Ag PLANT-PROTECTIVE AGENTS CONTAINING 1,2,4-TRIAZOLE DERIVATIVES AND NEW DERIVATIVES OF 1,2,4-TRIAZOLE
ES2054088T3 (en) 1988-10-20 1994-08-01 Ciba Geigy Ag SULFAMOILFENILUREAS.
DE3939010A1 (en) 1989-11-25 1991-05-29 Hoechst Ag ISOXAZOLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PLANT PROTECTIVE AGENT
DE3939503A1 (en) 1989-11-30 1991-06-06 Hoechst Ag NEW PYRAZOLINE FOR THE PROTECTION OF CULTURAL PLANTS AGAINST HERBICIDES
EP0492366B1 (en) 1990-12-21 1997-03-26 Hoechst Schering AgrEvo GmbH New 5-chloroquinolin-8-oxyalkanecarbonic acid derivatives, process for their preparation and their use as antidotes for herbicides
TW259690B (en) 1992-08-01 1995-10-11 Hoechst Ag
DE4331448A1 (en) 1993-09-16 1995-03-23 Hoechst Schering Agrevo Gmbh Substituted isoxazolines, processes for their preparation, compositions containing them and their use as safeners
JPH07285962A (en) * 1994-04-20 1995-10-31 Nissan Chem Ind Ltd Pyridinecarboxylic acid amide derivative
DE19621522A1 (en) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh New N-acylsulfonamides, new mixtures of herbicides and antidots and their use
DE69707907T2 (en) 1996-09-26 2002-05-16 Syngenta Participations Ag HERBICIDAL COMPOSITION
US5663365A (en) 1996-10-29 1997-09-02 Japan Hydrazine Co., Ltd. Process for the preparation of pyrazolones
DE19652961A1 (en) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh New 2-fluoroacrylic acid derivatives, new mixtures of herbicides and antidots and their use
US6071856A (en) 1997-03-04 2000-06-06 Zeneca Limited Herbicidal compositions for acetochlor in rice
DE19727410A1 (en) 1997-06-27 1999-01-07 Hoechst Schering Agrevo Gmbh 3- (5-tetrazolylcarbonyl) -2-quinolones and crop protection agents containing them
DE19742951A1 (en) 1997-09-29 1999-04-15 Hoechst Schering Agrevo Gmbh Acylsulfamoylbenzoic acid amides, crop protection agents containing them and process for their preparation
JP2000095778A (en) 1998-09-28 2000-04-04 Ube Ind Ltd Pyrazole derivative, production thereof and horticultural bactericide
AR031027A1 (en) 2000-10-23 2003-09-03 Syngenta Participations Ag AGROCHEMICAL COMPOSITIONS
EP1362852B1 (en) * 2001-02-20 2011-04-06 Sagami Chemical Research Center Pyrazole derivative, intermediate therefor, processes for producing these, and herbicide containing these as active ingredient
JP4559690B2 (en) 2001-03-23 2010-10-13 公益財団法人相模中央化学研究所 Pyrazole derivatives, production intermediates thereof, production methods thereof, and herbicides containing them as active ingredients
CA2456241A1 (en) 2001-08-08 2003-02-20 Basf Aktiengesellschaft Benzoylcyclohexenone derivatives
MXPA05010296A (en) 2003-03-26 2005-11-17 Bayer Cropscience Gmbh Use of aromatic hydroxy compounds as safeners.
DE10335725A1 (en) 2003-08-05 2005-03-03 Bayer Cropscience Gmbh Safener based on aromatic-aliphatic carboxylic acid derivatives
DE10335726A1 (en) 2003-08-05 2005-03-03 Bayer Cropscience Gmbh Use of hydroxyaromatics as safener
EP2522670A1 (en) 2004-04-07 2012-11-14 Takeda Pharmaceutical Company Limited Heterocyclic CRF receptor antagonists
DE102004023332A1 (en) 2004-05-12 2006-01-19 Bayer Cropscience Gmbh Quinoxaline-2-one derivatives, crop protection agents containing them, and processes for their preparation and their use
JPWO2007023719A1 (en) 2005-08-22 2009-02-26 クミアイ化学工業株式会社 Pesticide mitigation agent and herbicide composition with reduced phytotoxicity
JPWO2007023764A1 (en) 2005-08-26 2009-02-26 クミアイ化学工業株式会社 Pesticide mitigation agent and herbicide composition with reduced phytotoxicity
ES2358618T3 (en) 2006-07-14 2011-05-12 Chemocentryx, Inc. TRIAZOL PIRIDIL BENCENOSULFONAMIDAS AS MODULATORS OF CCR2 OR CCR9 FOR THE TREATMENT OF ARTERIOSCLEROSIS.
EP1987718A1 (en) 2007-04-30 2008-11-05 Bayer CropScience AG Utilisation of pyridine-2-oxy-3-carbon amides as safener
EP1987717A1 (en) 2007-04-30 2008-11-05 Bayer CropScience AG Pyridon carboxamides, agents containing these but not impacting useful plants and method for their manufacture and application
UA110324C2 (en) 2009-07-02 2015-12-25 Genentech Inc Jak inhibitory compounds based on pyrazolo pyrimidine
BR112012007349A2 (en) 2009-10-02 2019-09-24 Sanofi Sa use of compound with inhibitory activity of sglt-1 / sglt-2 for the production of drugs to treat bone diseases.
CN101838227A (en) 2010-04-30 2010-09-22 孙德群 Safener of benzamide herbicide
UY34585A (en) 2012-01-24 2013-09-02 Aicuris Gmbh & Co Kg B-LACTAMIC COMPOUNDS REPLACED WITH AMIDINE, ITS PREPARATION AND USE
US9422290B2 (en) * 2012-11-13 2016-08-23 Boehringer Ingelheim International Gmbh Triazolopyridazine
MX2015008912A (en) 2013-01-10 2015-10-22 Gruenenthal Gmbh Pyrazolyl-based carboxamides ii as crac channel inhibitors.
CN104513253A (en) 2013-10-01 2015-04-15 南京波尔泰药业科技有限公司 Macrocyclic compounds for the treatment of proliferative diseases
US9663502B2 (en) 2013-12-20 2017-05-30 Lycera Corporation 2-Acylamidomethyl and sulfonylamidomethyl benzoxazine carbamates for inhibition of RORgamma activity and the treatment of disease
EP3212636B1 (en) 2014-10-31 2023-11-29 F. Hoffmann-La Roche AG New pyridinyloxy- and phenyloxy-pyrazolyl compounds
JP6743032B2 (en) 2015-02-06 2020-08-19 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Pyrazole compounds as nitrification inhibitors

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