EP3227283A1 - Bicyclic compounds as pest control agents - Google Patents

Bicyclic compounds as pest control agents

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Publication number
EP3227283A1
EP3227283A1 EP15801853.1A EP15801853A EP3227283A1 EP 3227283 A1 EP3227283 A1 EP 3227283A1 EP 15801853 A EP15801853 A EP 15801853A EP 3227283 A1 EP3227283 A1 EP 3227283A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
radical
optionally substituted
substituted
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Withdrawn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
EP15801853.1A
Other languages
German (de)
French (fr)
Inventor
Thomas Bretschneider
Silvia Cerezo-Galvez
Arnd Voerste
Reiner Fischer
Martin FÜSSLEIN
Alexander ARLT
Peter Jeschke
Kerstin Ilg
Ulrich Görgens
Olga Malsam
Peter Lösel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP3227283A1 publication Critical patent/EP3227283A1/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D417/14—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 three or more hetero rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present application relates to novel bicyclic compounds, agents containing these compounds, their use for combating animal pests and methods and intermediates for their preparation.
  • WO 2012/102387 Al heterocyclic compounds are described, which can be used in particular as insecticides and acaricides.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides from various aspects.
  • B is a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
  • R 1 is a radical from the series hydrogen, alkyl, alkoxy and cyano
  • R 2 a) is a B radical from the series
  • dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or R 2 f) represents a radical of the formula wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
  • R 2 g) is optionally substituted phenyl, wherein is hydrogen or a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, optionally substituted and optionally interrupted by one or more heteroatoms saturated or unsaturated cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated Alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, bis (alkoxy) alkyl,
  • R 8 is where the dotted line represents the bond to the B residues
  • X is oxygen or sulfur
  • X 1 is a radical selected from among hydrogen, halogen, cyano, nitro, alkyl, haloalkyl,
  • X 2 is oxygen, sulfur, NR 5 or NOH
  • L is oxygen or sulfur
  • R is NR 18 R 19 or represents a respectively optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S (0) -alkyl, alkyl-S (0) 2 alkyl, R 18 -CO-alkyl, NR 18 R 19 is -CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl,
  • R 3 is hydrogen or alkyl
  • R 4 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl
  • R 5 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
  • R 3 and R 4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, or
  • R 3 and R 5 together with the nitrogen atoms to which they are attached form a ring
  • R 6 is hydrogen or alkyl
  • R 7 is a radical selected from hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
  • R 6 and R 7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
  • R 8 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl and optionally by halogen, alkyl, alkoxy, haloalkyl and cyano is substituted cycloalkylcarbonyl, or represents a cation or an optionally substituted by alkyl or arylalkyl ammonium ion,
  • R 9 is a radical from the series in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
  • R and R in the radicals (Cl) and (Fl) may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the or a plurality of further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group, R is hydrogen or alkyl,
  • R 8 and R 10 in the radicals (C-2) and (F-2) may also together with the N atoms to which they are bonded represent a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the at least one further heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
  • R and R in the radicals (C-2) and (F-2) may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
  • R U is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio stands,
  • R represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio .
  • R and R in the radicals (C-3) and (F-3) may also together with the phosphorus atom to which they are attached form a saturated or unsaturated and optionally substituted 5- to 7-membered ring, one or two Heteroatoms from the series oxygen (oxygen atoms may not be immediately adjacent) and may contain sulfur,
  • R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
  • R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
  • R 15 is a radical from the series each optionally substituted alkyl, alkenyl and alkynyl, each optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be included, respectively substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
  • R 8 and R 15 in the radicals (C-6) and (F-6) also together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring can form one or more other heteroatoms from the series sulfur,
  • Oxygen (where oxygen atoms are not immediately adjacent) and may contain nitrogen and / or at least one carbonyl group, a radical selected from the group consisting of hydrogen, each optionally substituted alkyl, alkoxy, alkenyl and alkynyl, respectively optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in in which each of the rings is at least one heteroatom selected from the group consisting of sulfur, oxygen (where oxygen atoms are not immediately adjacent) and nitrogen, optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
  • R “ and R 16 in the radicals (C-7) and (F-7) together with the N-atom to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or more other heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group, a radical from the series each optionally substituted alkyl, alkoxy, alkenyl and alkynyl, respectively optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl in which the rings may contain at least one heteroatom selected from sulfur, oxygen (where oxygen atoms are not immediately adjacent) and nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group R 8 and R 17 in the radicals (C-8) and (F-8) also together with the NC (X) group to which they are attached may form a saturated or
  • R 19 is a radical selected from the group consisting of hydrogen, an alkali metal or alkaline earth metal ion or an optionally monosubstituted to trisubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or an optionally halogen or cyano-substituted radical from the series consisting of alkyl, alkoxy, Alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl,
  • Y 3 is a radical from the group consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR 20 R 21 ,
  • W is a radical from the series O, S, SO and SO2,
  • R 22 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis (alkoxy) alkyl, optionally halogen-substituted alkylsulfanylalkyl, alkylcarbonylalkyl optionally substituted by halogen, optionally alkyl substituted by halogen, alkylsulphonylalkyl optionally substituted by halogen, dialkylaminosulphanylalkyl, dialkylaminosulphinylalkyl, dialkylaminosulphonylalkyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-substituted alkoxycarbon
  • alkyl is a radical selected from among hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy , Alkylsulfonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalky
  • R is a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, Haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cyanoalkyl, and compounds of the formula (I) in which A is the A radical (Aa)
  • G 1 is N or CB 1 ,
  • B 1 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
  • B 2 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
  • T oxygen or a pair of electrons
  • R 1 is a radical selected from the group consisting of hydrogen, alkyl, alkoxy and cyano,
  • the dashed line represents the bond to the carbon atom of the bicyclic compound of the formula (I) in which hydrogen or a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, optionally substituted and optionally saturated or unsaturated cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, haloalkylthioalkyl interrupted by one or more heteroatoms,
  • the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I)
  • wonn is a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, optionally substituted and optionally interrupted by one or more heteroatoms saturated or unsaturated cycloalkyl, cycloalkylalkyl, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylthioalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, bis (alkoxy) alkyl, bis (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl,
  • R 2 c is a radical of the formula
  • R f is a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
  • X is oxygen or sulfur
  • X 2 is oxygen, sulfur or NOH
  • L is oxygen or sulfur
  • R 4 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl, or
  • R 3 and R 4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
  • R 6 is hydrogen or alkyl
  • R 7 is a radical selected from hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
  • R 6 and R 7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
  • R 8 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl and optionally by halogen, alkyl, alkoxy, haloalkyl and cyano substituted Is cycloalkylcarbonyl, or is a cation or an optionally substituted by alkyl or arylalkyl ammonium ion,
  • R 9 is a radical from the series in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
  • R 10 is hydrogen or alkyl
  • R and R in the radicals (C-2) and (F-2) may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more other heteroatoms from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group, each of an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, Alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio, represents an optionally substituted radical from the series alkyl
  • R and R in the radicals (C-3) and (F-3) may also together with the phosphorus atom to which they are attached form a saturated or unsaturated and optionally substituted 5- to 7-membered ring, one or two Heteroatoms from the series oxygen (where
  • Oxygen atoms may not be immediately adjacent) and may contain sulfur, R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
  • R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
  • R 15 is a radical from the series each optionally substituted alkyl, alkenyl and alkynyl, each optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
  • R 8 and R 15 in the radicals (C-6) and (F-6) also together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
  • R 16 is a radical from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings are at least one heteroatom selected from the group consisting of sulfur, oxygen (oxygen atoms not being directly adjacent may each contain) and nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
  • R 8 and R 16 in the radicals (C-7) and (F-7) together with the N-atom to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, which may contain one or more further heteroatoms from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
  • R 17 is a radical from the series in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings are at least one heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and each may contain nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R 8 and R 17 in the radicals (C-8) and (F-8) together with the NC (X) group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring can contain one or more further heteroatoms from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group, and in the case that R 2 is one of the radicals listed under f) .
  • R 22 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis (alkoxy) alkyl, optionally halogen-substituted alkylsulfanylalkyl, optionally substituted by halogen alkylsulfinylalkyl, optionally substituted by halogen alkylsulfinylalkyl, optionally substituted by halogen alkylsulfinylalkyl, optionally substituted by halogen alkylsulfonylalkyl, dialkylaminosulfanylalkyl, dialkylaminosulfinylalkyl, dialkylaminosulfonyl
  • R 18 is a radical selected from the group consisting of hydrogen, hydroxy, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the rings at least one
  • R 20 is a radical selected from among hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy,
  • R 23 is a radical from the series consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl and alkoxyalkyl or, if R 2 is one of the radicals listed under f) stands,
  • R 22 and R 23 together with the nitrogen atom to which they are attached form a ring which may contain one or more other nitrogen, oxygen and sulfur heteroatoms, and
  • R is hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and
  • R is hydrogen or an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
  • R 27 is hydrogen or alkyl and R 26 is a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and Cyanoalkyl stands.
  • the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I) in which, for hydrogen or a radical from the series, halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno-C 1 -C 4 -alkylamino , di (Ci-C4-alkyl) amino, Ci-C4-alkyl, halo-Ci-C4- alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C3-C6 cycloalkyl C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy,
  • C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, ⁇ - ⁇ A-hydroxyimino-C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-imino-C 1 -C 4 -alkoxycarbonyl -C-C 4 alkyl, C (X 2) NR 3 R 4, NR 6 R 7, C 1 -C4- alkylthio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylthio , C1-C4 haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, the heterocyclyl
  • the dashed line denotes the bond to the B radicals, a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl, X is oxygen or sulfur,
  • X 1 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy,
  • X 2 is oxygen, sulfur, NR 5 or NOH
  • n is 1 or 2
  • R for NR 18 R 19 or for any given by halogen, oxygen (leads to C 0) or cyano substituted Ci-Ce-alkyl, C 3 -C 6 alkenyl, Cs-Ce-alkynyl, Ci-C 6 alkoxy -C-C 4 alkyl, Ci-C 6 - alkyl-S-Ci-C4-alkyl, Ci-C 6 alkyl-S (0) -C C-4 alkyl, Ci-C 6 alkyl S (0) 2- Ci-C 4 -alkyl, for R 18 -CO-Ci-C 4 -alkyl, for NR 18 R 19 -CO-Ci-C 4 -alkyl, optionally optionally once or twice by
  • R 4 is a radical selected from hydrogen, Ci-C 4 alkyl, halo-Ci-C4-alkyl, cyano-Ci-C 4 alkyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl , C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl , C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, R 5 is a radical from the series consisting of hydrogen, C 1 -C 4 Alkyl, halo-C 1 -C 4 -alkyl, cyano-C
  • R 3 and R 4 together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (where oxygen and sulfur atoms are not immediately adjacent may contain)
  • R 6 is hydrogen or C 1 -C 4 -alkyl
  • R 7 is a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 4 cycloalkyl-Ci-C4-alkyl, Ci-C 4 alkoxy, halogen-Ci-C 4 - alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxycarbonyl, Ci-C4 alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C 4 alkyl, aryl, aryl-Ci-C4-alkyl or hetaryl-Ci-C4 -alkyl, or
  • R 6 and R 7 together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (with oxygen and sulfur atoms not being immediately adjacent may contain)
  • R 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by halogen, Ci-Cö-alkyl, Ci-C6 Alkoxy, C 1 -C 6 -haloalkyl and cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or represents a cation or an ammonium ion which
  • R 9 is a radical from the series in each case optionally substituted by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 4 -alkyl -Cö-alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyl -
  • C6-cycloalkyl-Ci-C6-alkyl and C3-C6-cycloalkenyl in which a ring member by a heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
  • R 8 and R 9 in the radical (Cl) and in the radical (Fl) can also be used together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 -alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably a carbonyl group may contain, in particular R 8 and R 9 together with the NS (0) n group to which they are attached, a radical from the series
  • a radical from the series in each case optionally substituted by methyl, cyano, carbamoyl-substituted Ci-Cö-alkyl, C2-C6-alkenyl and C2-C6-alkynyl each optionally substituted by methyl, trifluoromethyl, halogen, cyano or carbamoyl substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C 2 -alkyl and C3-C6-cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur , Oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each optionally substituted by Ci-C i-alkyl, C1-C4-haloalkyl, Ci-C i-alkoxy, Ci-C i -haloalkoxy, Ci-C i alkylthio,
  • R 8 and R 15 in the radical (C-6) together with the NS (0) n group to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or two further heteroatoms from the series sulfur, oxygen (oxygen and sulfur atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group, a radical from the series hydrogen, in each case optionally by methyl, cyano, carbamoyl or carboxyl substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, each optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkyl cycloalkyl, Ci-Ce-alkoxy, Ci-Ce-halo
  • R is a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C -alkenyl, C 2 -C 6 Alkynyl, Cs-Ce-cycloalkyl (which is optionally substituted by halogen, cyano, Ci-C i-alkyl and C3-C6-cycloalkyl), C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 hal
  • R 21 is a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl Ci-Ce-alkyl, cyano-Ci-Ce-alkyl, Ci-C 6 - alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, Ci-C6-haloalkylcarbonyl, C 2 -C6-
  • R 23 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkoxy alkenyloxy, C2-C6 alkynyloxy, C3-C6-cycloalkyloxy, Ci-C4-alkylthio-Ci-C4-alkyl, C2-C4-alkenylthio Ci- C4-alkyl, cyano-Ci-C4- alkyl, Ci-C4- Alkoxy-Ci-C 4 -alkyl, or, in the case that R 2 is one of the radicals mentioned under c) or f)
  • R 22 and R 23 together with the nitrogen atom to which they are attached form a saturated ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms, and
  • R 24 is hydrogen or a radical optionally substituted by halogen or cyano radical from the series Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-Ci-C 2 alkyl stands, R is hydrogen or a radical optionally substituted by halogen or cyano radical from the series Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-Ci-C 2 alkyl .
  • R 27 is hydrogen or C i-alkyl
  • R 26 is a radical from the group of hydrogen, Ci-C / i-alkyl, Ci-C i-haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, C 3 -C 6 cycloalkyl, C3- C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 2 alkyl, Ci-C 6 - alkylsulfanyl, Ci-C6-Halogenalkylsulfanyl Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci- Ce-alkylsulfonyl, Ci-C4-alkylthio-Ci-C 2 alkyl, Ci-C 4 -Alkylsulfmyl-Ci-C 2 alkyl, C 1 -C4- alkylsulphonyl-Ci-C
  • G 1 is N or CB 1 ,
  • B 1 is a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
  • B 2 is a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
  • T oxygen or a pair of electrons
  • R 1 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy,
  • R 2 c is a radical of the formula
  • R 2 d is a radical of the formula
  • R 2 e for an F radical from the series (F-8), (F-10) and (F-11) wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
  • R 2 f is a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
  • X is oxygen or sulfur
  • X 2 is oxygen, sulfur or NOH
  • n is 1 or 2
  • R 3 is hydrogen or C 1 -C 6 -alkyl
  • R 4 is a radical from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl , C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl
  • Ci-C 4 -alkyl and hetaryl-Ci-C 4 -alkyl or
  • R 3 and R 4 together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (where oxygen and sulfur atoms are not immediately adjacent may contain)
  • R 6 is hydrogen or C 1 -C 4 -alkyl
  • R 7 is a radical from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 4 cycloalkyl-Ci-C4-alkyl, Ci-C 4 alkoxy, halogen-Ci-C 4 - alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 - alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C4-alkyl, Ci-C alkylthio-Ci-C alkyl, aryl, aryl-C alkyl or hetaryl-Ci-C -alkyl, or
  • R 6 and R 7 together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (with oxygen and sulfur atoms not being immediately adjacent may contain)
  • R 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by halogen, Ci-Cö-alkyl, Ci-C6 Alkoxy, C 1 -C 6 -haloalkyl and cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or represents a cation or an ammonium ion which
  • R 9 is a radical from the series in each case optionally substituted by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 4 -alkyl -Cö-alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyl -
  • C6-cycloalkyl-Ci-C6-alkyl and C3-C6-cycloalkenyl in which a ring member by a heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
  • R 15 is a radical from the series each optionally substituted by methyl, cyano, carbamoyl, substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each optionally substituted by methyl, trifluoromethyl, halogen, cyano or carbamoyl C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl and C 3 -C 6 -cycloalkenyl in which the rings may contain at least one heteroatom selected from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen in each case optionally by C 1 -C -alkyl, C 1 -C 4 -haloalkyl, C 1 -C -alkoxy, C 1 -C -haloalkoxy, C 1 -C 4 -alkylthio
  • R 8 and R 15 in the radical (C-6) together with the NS (0) n group to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or two further heteroatoms from the series sulfur, oxygen (where oxygen and sulfur atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
  • R 16 is a radical from the series hydrogen, in each case optionally substituted by methyl, cyano, carbamoyl or carboxyl-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, in each case optionally by halogen, Cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -cycloalkyl Alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkyls
  • R 2 is one of the radicals listed under f
  • a radical is selected from hydrogen, Ci-COE-alkyl, C 2 -C 6 haloalkyl, cyano-Ci-C6-alkyl, C 2 -C 4 alkenyl, C 2 -C i-haloalkenyl, C 2 -C 4 alkynyl, C 2 C 4 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl optionally substituted by halogen, optionally bis-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl substituted by halogen alkyl, optionally halogen-substit
  • Haloalkylsulfonyl amino, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-, haloalkoxy-Ci-Ce-alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, Ci-C 6 - alkylcarbonyl, CI-C ⁇ - alkoxycarbonyl or Aminocarbonyl substituted hetaryl-C 1 -C 6 -alkyl, and, in the case where R 2 is one of the radicals listed under c),
  • X 1 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy,
  • Y 3 is a radical selected from hydrogen, halogen, cyano, Ci-COE-alkyl, Ci-C6-haloalkyl, C3-Ce-cycloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, and NR 20 R 21 stands,
  • W is a radical from the series S, SO and SO2,
  • R 18 is a radical from the series consisting of hydrogen, hydroxyl, in each case optionally monosubstituted or polysubstituted by halogen or mono- or disubstituted by cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 - alkyl, Ci-C 6 alkyl-S-Ci-C4-alkyl, Ci-C 6 alkyl-S (0) -C C-4 alkyl, Ci-C 6 - alkyl-S (0) 2 - Ci-C4-alkyl, Ci-C6 alkylcarbonyl, Ci-C 6 alkoxycarbonyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - cycloalkenyl, C3-C6-cycloalkyl-Ci-C3-alkyl, C3 C6-cycloalkenyl-C
  • R 19 represents hydrogen, an alkali or alkaline earth metal ion or an optionally monosubstituted to cis-C 4 -alkyl-substituted ammonium ion or an optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted radical from the series Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S-Ci-C4-alkyl, C1-C4 alkyl-S (0 ) -Ci-C 4 -alkyl and Ci-C 4 -alkyl-S (0) 2 -Ci-C 4 -alkyl, in the case that R 2 is one of the radicals listed under f)
  • R 22 also for one of the E radicals (E-1) to (E-11)
  • R is a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C -alkenyl, C 2 -C 6 Alkynyl, Cs-Ce-cycloalkyl (which is optionally substituted by halogen, cyano, Ci-C i-alkyl and C3-C6-cycloalkyl), C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -
  • R 21 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl Ci-Ce-alkyl, cyano-Ci-C 6 alkyl, C 6 - alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, Ci-C6-haloalkylcarbonyl, C 2 -C6-
  • R 23 is a radical from the group of hydrogen, Ci-COE-alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C3-C6 cycloalkyl, C3-C6-cycloalkenyl, Ci-C6-alkoxy, C2- C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 4 -alkoxy-C 1 -C 4 -alkyl, or, if R 2 is one of the radicals listed under f),
  • R 24 is hydrogen or a radical optionally substituted by halogen or cyano radical from the series Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-Ci-C 2 alkyl stands,
  • R 25 is hydrogen or in each case optionally substituted by halogen or cyano radical from the series Ci-C 4 alkyl, C 2 -Ce-alkenyl, C 2 -C 6 -alkynyl, phenyl and phenyl-Ci-C 2 alkyl,
  • R 27 is hydrogen or C 1 -C 4 -alkyl
  • R 26 is a radical from the group of hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, C 3 -C 6 cycloalkyl, C3- C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 2 alkyl, Ci-C 6 - alkylsulfanyl, Ci-C6-Halogenalkylsulfanyl Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci- Ce-alkylsulfonyl, Ci-C4-alkylthio-Ci-C 2 alkyl, Ci-C 4 -Alkylsulfmyl-Ci-C 2 alkyl, C 1 -C4- alkylsulphonyl-Ci-C 2 alkyl,
  • B 2 is a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C -haloalkyl, Q is sulfur, R 1 is a radical selected from the group consisting of hydrogen, C 1 -C -alkyl and carbonyl.
  • C i-alkoxy, R 2 a) is a B radical from the series
  • R 2 c is a radical of the formula
  • R 23 is where the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or e) for an F radical from the series (Fl), (F-8) and (F-10)
  • R 2 g is a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
  • halogen is hydrogen or a radical from the series halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno-C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkyl, halogen C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkyl) 4 -alkoxy) -Ci-C 4 -alkyl, bis (halo-C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, C 1 -C 4 -al
  • X I is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkyl -C 4 haloalkoxy,
  • X 2 is oxygen, sulfur, NR 5 or NOH, n is 2,
  • R 3 is C 1 -C 4 -alkyl, a radical selected from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 - C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl and C 1 -C 4 -alkyl 4- alkylthio-C 1 -C 4 -alkyl,
  • R 5 is a radical from the group of hydrogen, Ci-C 4 alkyl, halo-Ci-C4-alkyl, cyano-Ci-C 4 alkyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl , C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
  • R 6 is hydrogen or C 1 -C 4 -alkyl
  • R 7 is a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, halogen -C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-Ci- -C 4 alkyl, aryl-Ci-C 4 - alkyl is or hetaryl-Ci-C4 alkyl, or
  • R 8 is a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 Alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, in each case optionally halogen-substituted C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkylsulfonyl, optionally C 1 -C 4 -alkoxycarbonyl which is substituted by halogen and optionally by halogen, C 1
  • R represents a radical from the series in each case optionally substituted by halogen, Ci-C4 alkoxy, C1-C4 haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl-substituted C 1 -C 4 - alkyl, C 2 -C 4 alkenyl and C 2 -C 4 alkynyl each optionally substituted by halogen, Ci-C 4 - Alkyl,
  • R 8 and R 9 in the radical (Cl) and in the radical (Fl) can also be used together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally halogen, CI-C ⁇ -alkyl, Ci -Cö-haloalkyl, Ci-C 6 alkoxy, Ci-C6-haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably contain exactly one carbonyl group, in particular R 8 and R 9 may together with the NS (0) n group to which they are attached, stand for a residue from the series
  • R 15 is a radical from the series each optionally substituted by methyl Ci-Cö-alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl and each optionally substituted by methyl, halogen, cyano or carbamoyl substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl and C3-C6-cycloalkenyl,
  • R 8 and R 15 in the radical (C-6) together with the NS (0) n group to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or two further heteroatoms from the series sulfur, oxygen (where Oxygen and sulfur atoms may not be immediately adjacent) and may contain nitrogen and / or at least one carbonyl group, a radical from the series in each case optionally substituted by halogen, Ci-C i-alkoxy, C1-C4-haloalkoxy, Ci-C4-alkylthio , C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -halogenoalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4
  • E-49 E-51 is, or, in the case that R 2 is one of the radicals listed under d)
  • R 23 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 Alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 -C 4 -alkyl, cyano-ci- C 4 -alkyl and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or, in the case where R 2 is one of the radicals listed under c) or f),
  • R 27 is hydrogen or C 1 -C 4 -alkyl
  • R 26 is a radical from the group of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 2 alkyl, C 1 -C4-
  • G 1 is N or CB 1 ,
  • B 1 is a radical selected from hydrogen, halogen, Ci-COE-alkyl and Ci-C i-haloalkyl
  • B 2 is a radical selected from hydrogen, halogen, Ci-COE-alkyl and Ci-C / i- Haloalkyl is
  • T oxygen or a pair of electrons
  • R 1 is a radical selected from the group consisting of hydrogen, C 1 -C -alkyl and C 1 -C -alkoxy,
  • R 2 d is a radical of the formula
  • X 2 is oxygen, sulfur or NOH, n is 2,
  • R 3 is C 1 -C 4 -alkyl
  • R 4 is a radical selected from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl , C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, R 6 represents hydrogen or C 1 -C 4 -alkyl,
  • R 7 is a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, halogen -C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-Ci- -C 4 alkyl, aryl-Ci-C 4 - alkyl or hetaryl-Ci-C 4 -alkyl, or R 6 and R 7 together with the nitrogen atom to which they are attached, a 4- to 7-membered ring
  • R 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by halogen, Ci-Cö-alkyl, Ci-C6 Alkoxy, Ci-C6-haloalkyl and cyano substituted C3-C6-cycloalkylcarbonyl, or represents a cation or an optionally substituted by Ci-Cö-alkyl or ary
  • R 8 and R 15 in the radical (C-6) together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring may contain one or two further heteroatoms selected from the group consisting of sulfur, oxygen (oxygen and sulfur atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group; C 1 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 - C 4 -C 4 -alkyl, C 2 -C 4 -alkenyl
  • R 19 is hydrogen, an alkali or alkaline earth metal ion, an optionally monosubstituted to fourfold substituted by Ci-C 4 alkyl ammonium ion or a each optionally mono- or polysubstituted by halogen or mono- or cyano-double-substituted radical from the series Ci- C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S-C 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S ( 0) -CC-C 2 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, or
  • R 23 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 4 -cycloalkyl C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl and C 1 -C 4 -alkyl C4-alkoxy-Ci-C 4 alkyl, or, when R 2 is one of the radicals listed under f
  • R 22 and R 23 may also together with the nitrogen atom to which they are attached form a saturated four- to six-membered ring which may contain another heteroatom from the series consisting of nitrogen, oxygen and sulfur,
  • R 27 is hydrogen or C 1 -C 4 -alkyl
  • R 26 is a radical from the group of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - Cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 4 alkylsulfonyl, Ci-C4-alkylthio-Ci-C 2 alkyl, Ci-C 4 -Alkylsulfmyl-Ci-C 2 alkyl, C 1 -C
  • R 1 is hydrogen
  • R 2 c is a radical of the formula
  • the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or f) a radical of the formula wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or g) a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
  • G 2 is hydrogen or a radical selected from halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkyl, halogen -C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy alkyl, bis-C 4 -C (Ci-C 4 alkoxy) alkyl, bis-C 4 -C (halo-Ci-C4-alkoxy) alkyl, Ci-C4 alkoxy (Ci- C4 -alkylsulfanyl)
  • the dashed line represents the bond to the B-radicals, a radical from the series hydrogen, halogen, Ci-C 4 - alkyl and Ci-C 4 haloalkyl, represents oxygen, a radical from the series Is hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, is oxygen, sulfur, NR 5 or NOH, is 2, NR 18 R 19 or any one of them once, twice, three times, four times or five times by fluorine, chlorine or mono- or disubstituted by cyano radical from the series Ci- C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 2 -alkoxy-Ci-C 2 alkyl, and Ci-C2 alkyl-S-Ci-C 2 - alkyl, Ci-C2 alkyl, Ci
  • R 3 is C 1 -C 4 -alkyl
  • R 4 is a radical from the series consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C3-C6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 Alkoxycarbonyl-C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
  • R 5 is a radical from the group of hydrogen, Ci-C 4 alkyl, halo-Ci-C4-alkyl, cyano-Ci-C 4 alkyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl , C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
  • R 6 is hydrogen or C 1 -C 4 -alkyl
  • R 7 is a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, halogen -C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-Ci- -C 4 alkyl, aryl-Ci-C 4 - alkyl is or hetaryl-Ci-C4 alkyl, or
  • R 6 and R 7 together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (with oxygen and sulfur atoms not being immediately adjacent may contain)
  • R 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by halogen, Ci-Cö-alkyl, Ci-C6 alkoxy, Ci-C6-haloalkyl and cyano substituted C3-C6 cycloalkylcarbonyl group, or an optionally a cation or CI-C ⁇ - represents alkyl or
  • R represents a radical from the series in each case optionally substituted by halogen, Ci-C4 alkoxy, C1-C4 haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4 alkylsulfinyl, C1-C4 Haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, each optionally substituted by halogen, C 1 -C 4 -alkyl, C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, substituted C 3 -C 6 -cycloalkyl, C 3 -C 6
  • R 8 and R 9 in the radical (Cl) and in the radical (Fl) can also be used together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally halogen, CI-C ⁇ -alkyl, Ci -Cö-haloalkyl, Ci-C 6 alkoxy, Ci-C6-haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably a carbonyl group may contain, in particular R 8 and R 9 may together with the NS (0) n group to which they are attached, stand for a residue from the series
  • R 27 is hydrogen or methyl and R 26 is a radical from the group consisting of hydrogen, methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl, propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl, methylsulfanyl, trifluoromethylsulfanyl, ethylsulfanyl, Trifluoroethylsulfanyl, methylsulfinyl,
  • G 1 is N or CB 1 ,
  • B 1 is a radical from the series hydrogen and fluorine
  • T oxygen or an electron pair
  • Q is sulfur
  • R 1 is hydrogen
  • G 2 is a radical from the group consisting of halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, halogeno C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, bis (halogen-C 1 -C 4 -alkoxy) -C-C 4 alkyl, Ci-C4-alkoxy- (Ci-C4-alkylsulfanyl) -C-C 4 alkyl, Ci-C4-alkoxy- (Ci-C 4 - alkylsulfanyl
  • G 2 is also one of the following C radicals
  • R is where the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I), or
  • X is oxygen
  • X 2 is oxygen
  • sulfur NOH
  • n 2
  • R 3 is C 1 -C 4 -alkyl
  • R 4 is a radical selected from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl , C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
  • R 5 is a radical from the group of hydrogen, Ci-C 4 alkyl, halo-Ci-C4-alkyl, cyano-Ci-C 4 alkyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl , C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
  • R 6 is hydrogen or C 1 -C 4 -alkyl
  • R 7 is a radical from the series consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkyl, C 4 -alkynyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkoxy C 4 alkyl, Ci-C4-alkylthio-Ci-C 4 alkyl, aryl-Ci-C 4 - alkyl is or hetaryl-Ci-C4 alkyl, or
  • R 6 and R 7 together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms
  • R 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by
  • Ci-Cö-alkyl, Ci-C6-Alkoxy, Ci-C6-haloalkyl and Cyano substituted C3-C6-Cycloalkylcarbonyl stands, or for a cation or an optionally by Ci-Cö-alkyl or Aryl-Ci-Cö-alkyl substituted ammonium ion is, 1 ⁇
  • - 106 - is a radical from the series in each case optionally substituted by halogen, Ci-C i-alkoxy, C1-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl , C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, each optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, Haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy-sub
  • Alkyl a radical selected from the group consisting of hydrogen, hydroxyl, in each case optionally mono-, di-, tri-, tetra- or quintuple by fluorine, chlorine or mono- or di-cyano-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-S-C 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S (0) -CC-C 2 -alkyl, C 1 -C 4 -alkyl -C 4 alkyl-S (0) 2 -C-C 2 alkyl, Ci-C 4 alkylcarbonyl, C 1 -C4- alkoxycarbonyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C3-al
  • R is NR R, or for an in each case optionally monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted by fluorine, chlorine or mono- or disubstituted by cyano radical from the series Ci- C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, Ci-C 2 alkoxy-Ci-C 2 alkyl, and Ci-C2 alkyl-S-Ci-C 2 - alkyl, Ci-C2 alkyl-S (0) -ci- C 2 -alkyl, C 1 -C 2 -alkyl-S (0) 2 -C 1 -C 2 -alkyl, for R 18 -CO-C 1 -C 2 -alkyl, for NR 18 R 19 -CO-C 1 -C 2 alkyl, optionally mono- or disubstituted by Ci-
  • X 1 is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
  • W is a radical from the series S, SO and S0 2 ,
  • Y 3 is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, or
  • R 23 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkoxy Alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 1 -C 4 Alkoxy-Ci-C 4 -alkyl, or, if R 2 is one of the radicals listed under f)
  • R 22 and R 23 are also taken together with the nitrogen atom to which they are attached, for pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl-1-oxide, thiomorpholinyl-1,1-dioxide, piperazinyl, 1-methylpiperazinyl or 2-oxo l-methylpiperazinyl, R 27 is hydrogen or methyl and
  • R 26 is a radical from the group consisting of hydrogen, methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl, propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl, methylsulfanyl, trifluoromethylsulfanyl, ethylsulfanyl, trifluoroethylsulfanyl, methylsulfinyl,
  • Preferred Range (4) A preferred group of compounds of the formula (I) are those in which
  • G 1 stands for CB 1 ,
  • B 1 is hydrogen or fluorine
  • B 2 is hydrogen
  • T stands for a pair of electrons
  • Q stands for sulfur
  • R 1 is hydrogen
  • the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or f) a radical of the formula wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or g) a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
  • G 2 is hydrogen or a radical from the series Ci-C i-alkyl, halo-Ci-C i-alkyl and pyrimidyl,
  • G 3 is a radical selected from the group consisting of hydrogen, halogen and C 1 -C 1 -alkyl,
  • X I is a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl and ethyl,
  • R represents optionally mono-, di-, tri-, tetra- or quintuply fluorine-, chlorine-substituted Ci-C / i-alkyl
  • W is a radical from the series S, SO and SO2
  • R 23 is hydrogen or C 1 -C 6 -alkyl, or
  • R 22 and R 23 together with the nitrogen atom to which they are attached represent morpholinyl.
  • G 1 is N or CB 1 ,
  • B 1 is a radical selected from the group consisting of hydrogen and fluorine
  • B 2 is hydrogen
  • T stands for a pair of electrons
  • R 1 is hydrogen
  • G 2 is hydrogen or a radical from the series Ci-C i-alkyl, halo-Ci-C i-alkyl, Ci-C i-alkoxy, halo-Ci-C i-alkoxy, Ci-C4-alkylthio-Ci C4-alkyl, halogenated Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylthio, C1-C4 haloalkylsulfinyl , Ci-C4-haloalkylsulfonyl, or
  • R 2 c) is a radical of the formula
  • R is wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I), is oxygen, the D moiety
  • R is optionally substituted once, twice, three times, four times or five times by fluorine, chlorine or mono- or disubstituted cyano-substituted GC i-alkyl,
  • X 1 is hydrogen, methyl or fluorine,
  • W is a radical from the series S, SO and SO 2
  • Y 3 is hydrogen or methyl
  • R 23 is a radical from the series hydrogen and Ci-Cö-alkyl.
  • Cation an alkali metal ion selected from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or a
  • Alkaline earth ion selected from the series beryllium, magnesium, calcium, strontium, barium, preferably from the series magnesium, calcium,
  • Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine, aryl (also part of a larger unit such as arylalkyl) selected from the series phenyl, naphthyl, anthryl, phenanthrenyl and stands again preferred for phenyl,
  • Hetaryl (equivalent to heteroaryl, also as part of a larger unit such as hetarylalkyl) selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1, 2,4-triazolyl, oxazolyl, isoxazolyl , Thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1, 2,4 Thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5- Thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1, 2,4-triazinyl, 1,3,5-triazinyl, benzof
  • Heterocyclyl a saturated 4-, 5- or 6-membered ring containing 1 or 2 nitrogen atoms and / or an oxygen atom and / or a sulfur atom, for example azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl , Tetrahydrofuryl, piperazinyl, morpholinyl.
  • the combination of which forms the preferred range (2) unless otherwise stated,
  • Alkaline earth ion selected from the series beryllium, magnesium, calcium, strontium, barium, preferably from the series magnesium, calcium,
  • Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
  • Aryl also as part of a larger unit, such as arylalkyl selected from the group phenyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents phenyl, hetaryl (equivalent to heteroaryl, also as part of a larger unit, such as hetarylalkyl) selected from of the series pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1, 2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1, 2, 4-triazinyl, 1,3,5-triazinyl,
  • Heterocyclyl selected from azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl, piperazinyl, morpholinyl.
  • Hetaryl (synonymous with heteroaryl, as part of a larger unit, such as hetarylalkyl) for a radical from the series pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, thiazolyl and pyrazolyl.
  • Halogen for fluorine, chlorine, bromine and iodine preferably again fluorine, chlorine and bromine.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • (A-a) is an electron pair, the remainder is as a pyridine derivative of the formula
  • (A-a) is oxygen, the remainder is a pyridine-N-oxide derivative of the formula
  • a preferred embodiment of the invention relates to compounds of the formula (I) in which A represents the radical of the formula (Aa)
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyridin-3-yl.
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A is 5-fluoropyridin-3-yl.
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyrimidin-5-yl.
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyridazin-4-yl.
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under a).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under b).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under c).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under d).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under e).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under f).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under g).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical (D-2)
  • radical definitions or explanations given above apply to the end products (also for the compounds of the formulas (IA) to (IP) listed below and correspondingly to the starting materials and intermediates.) These radical definitions can be used among one another, ie also between the respective Preferred areas, can be combined arbitrarily.
  • the invention relates to compounds of the formula (I-C)
  • the invention relates to compounds of the formula (ID)
  • the invention relates to compounds of the formula (I-E)
  • the invention relates to compounds of the formula (I-F)
  • the invention relates to compounds of the formula (I-G)
  • the invention relates to compounds of the formula (I-H)
  • the invention relates to compounds of the formula (II)
  • the invention relates to compounds of the formula (IJ)
  • the invention relates to compounds of the formula (IK)
  • the invention relates to compounds of the formula (III) _
  • the invention relates to compounds of the formula (I-N)
  • the invention relates to compounds of the formula (I-O)
  • the invention relates to compounds of the formula (IP)
  • the compounds of the formula (I) and their acid addition salts and metal salt complexes have good activity, in particular for combating animal pests, which include arthropods and in particular insects.
  • Suitable salts of the compounds of the general formula (I) may be customary non-toxic salts, ie salts with corresponding bases and salts with added acids.
  • salts with inorganic bases such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases and with inorganic amines, for example triethylammonium, dicyclohexylammonium, ⁇ , ⁇ '- Dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates, or phosphates, salts with organic carboxylic acids or organic sulfonic acid, for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesul
  • the compounds of the formula (I) may also be present in different compositions as stereoisomers, ie as geometric and / or optical isomers or mixtures of isomers. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.
  • the invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for controlling animal pests, which include arthropods and in particular insects.
  • optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention.
  • the substituted anilines of the formula (Al-I) with activated carboxylic acids (for example as the carboxylic acid chloride or its hydrochloride) of the formula (AI-II) in the presence of basic reaction auxiliaries in a first reaction step to compounds of formula (AI -III ) are implemented. These are then by sulfur donors such. B. Lawesson's reagent to compounds of formula (AI -IV) thionated. In a third reaction step, these can then be cyclized in the presence of a suitable base, for example potassium carbonate, to give the compounds of the formula (I).
  • a suitable base for example potassium carbonate
  • Method A - Step 1 The compounds of the formula (Al-I) are known in some cases and are commercially available or can be prepared by methods known in principle (for example for R 1 HH, R 2 BrBr 4 -bromo-2 fluoraniline (see GB 2 065 654 A).
  • Suitable condensing agents are all condensing agents customarily used for such amidation reactions. Examples which may be mentioned are acid halide formers such as phosgene, phosphorus trichloride, oxalyl chloride or thionyl chloride; Carbodiimides such as NN-dicyclohexylcarbodiimide (DCC) and 1- (3-dimethylaminopropyl) -3-ethyl-carbodiimide (EDCI), or other conventional condensing agents such as phosphorus pentoxide, polyphosphoric acid, NN-carbonyldiimidazole, 2-chloropyridine 1-methiodide (Mukaiyamas reagent ), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyrrolidino-phosphonium hexafluorophosphat
  • Suitable acid acceptors are all customary inorganic or organic bases, for example triethylamine, diisopropylethylamine, N-methylmorpholine or N, N-dimethylaminopyridine. If appropriate, process A according to the invention is carried out in the presence of a suitable reaction auxiliary, for example N, N-dimethylformamide or N, N-dimethylaminopyridine.
  • Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons (such as petroleum ether, toluene), halogenated hydrocarbons (such as chlorotoluene, dichloromethane, chloroform, 1, 2-dichloroethane), ethers (such as diethyl ether, dioxane, tetrahydrofuran , 1, 2-dimethoxyethane), esters (such as ethyl acetate or methyl ester), nitrohydrocarbons (such as nitromethane, nitroethane, nitrobenzene), nitriles (such as acetonitrile, benzonitrile), amides (such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide , N-methylpyrrolidone, hexamethylphosphoric triamide) and dimethyl sulfoxide or water or
  • LG COOR
  • R alkyl, aryl
  • chloroformates can be used, such.
  • diethylacetyl chloride, trimethylacetyl chloride and the like can be used therefor.
  • Method A - Step 2 The amide function of the carboxylic acid amides of type (AI-III) can be achieved by suitable sulfurization reagents, e.g. Lawesson's reagent or phosphorus (V) sulfide, with heating in a suitable solvent, e.g. As toluene or anisole, are converted into a thioamide function, whereby compounds of the type (AI -IV) are formed [cp. z. WO2013 / 33901 for 5-bromo-N- (2,6-difluorophenyl) -pyridine-3-carbothioamide]. Partial cyclization to the type of compound (I) can already take place in this type of reaction.
  • suitable sulfurization reagents e.g. Lawesson's reagent or phosphorus (V) sulfide
  • a suitable solvent e.g. As toluene or anisole
  • the compounds of the formula (I) can be prepared by methods known from the literature (cf., for example, WO2013 / 33901 for 2- (5-bromopyridin-3-yl) -4-fluoro-1, 3 benzothiazole)) by heating in a suitable solvent, e.g. For example, toluene or DMF, in the presence of a base such as. As sodium hydride or potassium carbonate, in the thiazoles of the formula (I) convert.
  • brominated benzothiazoles can be prepared with in situ generated substituted arylboronic acids or aryl boronic acid pinacol esters in the presence of coupling catalysts, such as tetrakis (triphenylphosphine) palladium (0) or 1,1'-bis (diphenylphosphino) ferrocene] dichloro-palladium (II), in the presence of a base such.
  • coupling catalysts such as tetrakis (triphenylphosphine) palladium (0) or 1,1'-bis (diphenylphosphino) ferrocene] dichloro-palladium (II)
  • a base such as sodium carbonate, in an inert organic solvent or diluent, for.
  • arylation As dioxane in combination with water, arylation (Method B), whereby carbon-linked compounds of the type (I-b) [cf.
  • the compounds of the formula (I-a) can first be converted by methods known from the literature into compounds of the type (I-h) which are then subsequently reacted with halogen-activated and optionally, further substituted heterocycles according to Reaction Scheme II (Method F) [cf. T. Ishiyama et al, J. Org. Chem., 1995, 60, 7508-7510; WO 2010/151601] continue to react in an inert organic solvent or diluent to give carbon-bonded compounds of the type (I-i).
  • Suitable coupling catalysts are palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II)] or tetrakis (triphenylphosphine) palladium (O).
  • palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II)] or tetrakis (triphenylphosphine) palladium (O).
  • the basic reaction auxiliaries for carrying out the processes according to Reaction Scheme II are preferably carbonates of sodium or potassium.
  • the solvents used are preferably nitriles, such as acetonitrile, benzonitrile, in particular acetonitrile, or ethers, such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, in particular 1,2-dimethoxyethane in combination with water.
  • nitriles such as acetonitrile, benzonitrile, in particular acetonitrile
  • ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, in particular 1,2-dimethoxyethane in combination with water.
  • Method C By means of catalysis by suitable coupling catalysts, such as tris (dibenzylideneacetone) dipalladium (O) using suitable ligands, for.
  • suitable coupling catalysts such as tris (dibenzylideneacetone) dipalladium (O) using suitable ligands, for.
  • B. 2,2'-bis (diphenylphosphino) -l, l'binaphthyl (BINAP), and a base such as sodium tert-butoxide can be brominated benzothiazoles of the formula (Ia) in an inert organic solution or Diluents with optionally substituted aliphatic primary or secondary amines to give compounds of the type (Ic) or (Id) [cf. z.
  • Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons (for example toluene).
  • Method D With optionally substituted anilines, brominated benzothiazoles of the formula (I-a) react in an inert organic solvent or diluent to give the arylamino compounds of the formula (I-e) [cf. also Application Example 18]), preferably with catalysis by coupling catalysts such as palladium (II) diacetate in the presence of a base, for. B.
  • Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons (for example toluene).
  • Method E Heterocyclic amines, such as optionally substituted imidazoles, pyrazoles or triazoles, can be prepared on the basis of the method E shown in Reaction Scheme II [cf. WO 2008/130368] preferably in the presence of suitable catalysts such as copper (I) iodide, in the presence of basic ligands, for.
  • Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons (for example toluene), but also more polar solvents such as DMF.
  • Method G - Step 1 Compounds of the formula (I) in which R 2 is halogen, for example bromine or iodine, can be prepared by methods known from the literature using carbon monoxide and an alcohol, eg. As ethanol, with catalysis by suitable metal compounds such as (1,1'-bis (diphenylphosphino) ferrocene) palladium (II) dichloride, and in the presence of bases such as triethylamine, in suitable solvents such. B. the alcohol itself, THF and / or DMF, to the corresponding carboxylic acid esters (Ij) are reacted [see.
  • suitable metal compounds such as (1,1'-bis (diphenylphosphino) ferrocene) palladium (II) dichloride
  • bases such as triethylamine
  • Method G - Step 2 The compounds of the formula (I-j) can be prepared by means of suitable bases, such. As aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as. As dioxane or THF, to compounds of formula (I-k) are reacted with free acid function.
  • suitable bases such as aqueous lithium hydroxide or sodium hydroxide solution
  • suitable solvents or diluents such as.
  • dioxane or THF to compounds of formula (I-k) are reacted with free acid function.
  • Method G - Steps 3 and 4 Compounds of the formula (I) in which R 2 is a radical from the series (Cl) to (C-9) (Type Im) or for CX-NR 22 R 23 (Type In)
  • R 2 is a radical from the series (Cl) to (C-9) (Type Im) or for CX-NR 22 R 23 (Type In)
  • compounds of formula (I) in which R 2 is a carboxyl group (type Ik) after appropriate activation (ie LG represents an optionally in situ generated nucleofuge leaving group "Leaving Group") can be prepared by well-known methods to be produced [cf. Method A, step 1].
  • Compounds of the formula (I) in which R 2 is a group of the formula -NR 23 -C (X) -R 22 can, for example, be prepared from compounds of the formula (I) in which R 2 is a group of the formula -NHR 23 , by N-acylation reaction using activated compounds of the formula LG-C (X) - R 22 , wherein LG is an optionally in situ generated nucleofuge leaving group, can be obtained.
  • LG Leaving group, z. B. halogen
  • Method III For example, compounds of the formula (I-o) can be obtained by Curtius degradation, as described in Houben-Weyl, Methods of Organic Chemistry, Volume XI / 1 (Georg Thieme Verlag Stuttgart), page 865.
  • the compounds of the formula (I-k) can react, for example, with diphenylphosphoryl azide (DPPA) in the presence of tert-butanol directly to compounds of the formula (I-o).
  • DPPA diphenylphosphoryl azide
  • the compounds of the formulas (Ip) can be obtained by N-alkylation in a first reaction step, N-deblocking (ie cleavage of the Boc group) in a second reaction step and subsequent N-acylation in a third reaction step receive.
  • the compounds of the formula (Iq) can be prepared by N-deblocking (ie cleavage of the Boc group) in a first reaction step and subsequent N-acylation in a second reaction step.
  • acidic or basic reaction auxiliaries can be used according to the literature procedure for the removal of the protective group.
  • carbamate-type protecting groups preference is given to using acidic reaction auxiliaries.
  • tert-butylcarbamate protective group for example, mixtures of mineral acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid or of organic acids such as benzoic acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, Benzenesulfonic acid or toluenesulfonic acid in a suitable diluent such as water and / or an organic solvent such as tetrahydrofuran, dioxane, dichloromethane, chloroform, ethyl acetate, ethanol or methanol.
  • suitable diluent such as water and / or an organic solvent
  • the compounds of the types Ip or Iq can also be prepared from compounds synthesized according to method A by the method H2 described below:
  • RM reducing agent, z. Fe, Zn, Sn (II), sodium cyanoborohydride, hydrogen on Pd / C, etc.
  • LG Leaving group, e.g. B. Halogen or OH Method H2: Compounds prepared according to Method A in which R 2 is nitro (Ir) can be converted into the corresponding amino compounds (Is) by reduction of the nitro group by methods known from the literature (cf., for example, WO2009 / 14674 AI, 2009 for reduction by Fe (0); US2005 / 197331 AI, 2005 for reduction by Sn (II) C12; WO2007 / 86800 AI, 2007 for reduction by sodium cyanoborohydride).
  • Compounds of the formula (I) in which W is SO (sulfoxides) or SO 2 (sulfones) can be prepared by oxidation by literature methods from compounds of the formula (I) in which W is S (thioethers), for example by an oxidizing agent in a suitable solvent or diluent.
  • Suitable oxidizing agents are, for example, dilute nitric acid, hydrogen peroxide, Oxone® and peroxycarboxylic acids, such as wefa-chloroperbenzoic acid.
  • Suitable solvents or diluents are inert organic solvents, typically acetonitrile and halogenated solvents such as dichloromethane, chloroform or dichloroethane, and water and alcohols such as methanol for the reaction with Oxone®.
  • suitable anilines R'-NF or boronic acids R 1 -B (OH) 2 in which W is SO or SO 2 , according to method D D approaching. D.
  • Enantiomerically enriched sulfoxides can be prepared by a variety of methods as described by GE O'Mahony et al in ARKIVOC (Gainesville, FL, United states), 2011, 1, 1-110: metal-catalyzed asymmetric oxidations of thioethers, for example, with titanium or vanadium as the most commonly used catalyst sources, in the form of Ti (0'Pr4) or VO (acac) 2, together with a chiral ligand and an oxidizing agent such as tert-butyl hydrogen peroxide (TBHP), 2-phenylpropan-2-yl hydroperoxide (CHP ) or hydrogen peroxide; non-metal catalyzed asymmetric oxidations by using chiral oxidants or chiral catalysts; electrochemical or biological asymmetric oxidation as well as kinetic resolution of sulfoxides and nucleophilic displacement (according to Andersen's method).
  • TBHP tert-butyl hydrogen per
  • the enantiomers can also be obtained from the racemate, for example by preparative separation by means of a chiral HPLC. With the production methods described above, it is also possible to prepare those compounds in Table 1 which do not fall under the formula (I).
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions.
  • These stereoisomers are, for example, enantiomers, Diastereomers, atropisomers or geometric isomers.
  • the invention thus comprises pure stereoisomers as well as any mixtures of these isomers.
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
  • pest control always includes the term pesticides.
  • the compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreation, storage and materials protection and hygiene. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests of the genus Arthropoda in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eotetranychus hi
  • Aulacorthum solani Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp.
  • Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., Eg Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Eg Lecanium corni ( Parthenolecanium corni), Lepidosaphes spp., Eg Lepidosaphes ulmi, Lipaphis erysimi, Lycorma americanula, Macrosiphum spp., eg Macrosiphum euphorbiae, Macrosiphum lilii, Macrosi
  • Pemphigus spp. Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseu
  • Pseudaletia unipuncta Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., eg Schoenobius bipunctifer, Scirpophaga spp., eg Scirpophaga innotata, Ontario segetum, Sesamia spp., eg Sesamia infe Spartoptera spp., Spodoptera spp., Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp.,
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
  • Pests of the Mollusca strain in particular of the bivalve class, e.g. Dreissena spp .; and from the class of Gastropoda e.g. Arion spp., E.g. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
  • Animal and human parasites from the strains of Platyhelminthes and Nematoda e.g. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp.
  • Clonorchis spp. Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp.
  • Hyostrongylus spp. Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria sp Paraglia spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma s
  • Strongyloides spp. Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp .;
  • Plant pests from the Nematoda strain ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Eg Cacopaurus pestis, Criconemella spp., eg Criconemella curvata, Criconemella onoensis, Criconemella omat
  • the compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as a remedy for MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the present invention further relates to formulations and application forms prepared therefrom as pesticides such.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the use forms contain other pesticides and / or the effect of improving adjuvants such as Penetrationsforderer, z.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetable fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts such as organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-demanding agents such as.
  • dioctylsulfosuccinate or hydroxypropyl guar polymers and / or humectants such as glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • CS capsule concentrates
  • the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • auxiliaries such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or biological properties To give properties.
  • polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such as
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic Hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g. Cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • aromatic hydrocarbons e.g. Xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or aliphatic hydrocarbons e
  • Suitable carriers are, in particular: Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: e.g.
  • Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
  • liquefied gaseous diluents or solvents can be used.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates , Arylsulfonates, protein hydrolys
  • dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
  • the formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other auxiliaries may be mineral and vegetable oils.
  • further auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Penetration promoters in the present context include all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as for example Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12)
  • fatty acid esters such as rapeseed oil or soybean oil
  • fatty amine alkoxylates such as for example Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • the formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.
  • the content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie.
  • the application is done in a custom forms adapted to the application.
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be, for example to widen the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-exposure or to prevent the development of resistance.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators
  • suitable fungicides bactericides, acaricides, molluscicides, ne
  • the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
  • the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below. If one of the following compounds can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case.
  • Insecticides / Acaricides / Nematicides The active substances mentioned here with their "common name” are known and described, for example, in the Pesticide Handbook ("The Pesticide Manual” 16th ed., British Crop Protection Council 2012) or searchable on the Internet (eg http: // www. alanwood.net/pesticides).
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and Xylylcarb or organophosphates, eg Acephate, Azamethiphos, Azinophos-ethyl, Azinophos-methyl, Cadusafos, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos,
  • GABA-controlled chloride channel antagonists such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
  • sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. Acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin,
  • Bioallethrin S-cyclopentenyl isomer bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, flumethrin, tau-fluvalinates, halfenprox, imiprothrin, kadethrin, permethrin, phen
  • nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, eg acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • nAChR nicotinergic acetylcholine receptor
  • nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
  • chloride channel activators such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone mimics such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen.
  • Juvenile hormone mimics such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen.
  • agents with unknown or non-specific mechanisms of action such as
  • Alkyl halides e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
  • mite growth inhibitors e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • Insect intestinal membrane microbial disruptors e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
  • oxidative phosphorylation inhibitors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and fenbutatin oxide or propargite or
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, Thiocyclam and Thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Moulting inhibitors especially in dipterans, ie tails), such as Cyromazine.
  • ecdysone receptor agonists such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
  • Octopaminergic agonists such as amitraz.
  • Complex III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.
  • (21) complex I electron transport inhibitors for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • (22) voltage dependent sodium channel blockers e.g. Indoxacarb or metaflumizone.
  • complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.
  • Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
  • ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide.
  • drugs with unknown or ambiguous mechanism of action such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolites, cyclaniliprole, cycloxapride, cyhalodiamide dicloromezotiaz, dicofol, diflovidazine, flometoquine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, Flaxxafon, Fluopyram, Fluralaner, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Meperfluthrin, Paichongding, Pyflubumide, Pyralidyl, Pyrifluquinazone, Pyriminostrobin, Tetramethylfluthrin
  • All listed fungicidal mixing partners of classes (1) to (15) can optionally form salts with corresponding bases or acids, provided that suitable functional groups are present. Furthermore tautomeric forms are also included for the listed five-membered hybrids of classes (1) to (15), provided that tautomerism is possible.
  • inhibitors of ergosterol biosynthesis for example (1.01) aldimorph, (1.02) azaconazole, (1.03) bitertanol, (1.04) bromuconazole, (1.05) cyproconazole, (1.06) diclobutrazole, (1.07) difenoconazole, (1.08) diniconazole, (1.09 ) Dinemonazole-M, (1.10) dodemorph, (1.11) dodemorphoacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole-cis,
  • inhibitors of mitosis and cell division for example (4.01) benomyl, (4.02) carbendazim, (4.03) chlorfenazole, (4.04) diethofencarb, (4.05) ethaboxam, (4.06) fluopicolide, (4.07) fuberidazole, (4.08) pencycuron, (4.09) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2A (4.14) 3-
  • inhibitors of amino acid and / or protein biosynthesis for example (7.01) andoprim, (7.02) blasticidin-S, (7.03) cyprodinil, (7.04) kasugamycin, (7.05) kasugamycin hydrochloride hydrate, (7.06) Mepanipyrim, (7.07) pyrimethanil, (7.08) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (7.09) oxytetracycline, (7.10) streptomycin.
  • inhibitors of ATP production for example (8.01) fentin acetate, (8.02) fentin chloride, (8.03) fentin hydroxide, (8.04) silthiofam.
  • inhibitors of cell wall synthesis for example (9.01) benthi- avalicarb, (9.02) dimethomorph, (9.03) flumorph, (9.04) iprovalicarb, (9.05) mandipropamide, (9.06) polyoxines, (9.07) polyoxorim, (9.08) validamycin A, ( 9.09) Valifenalate, (9.10) Polyoxin B, (9.11) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop -2-en-1-one, (9.12) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4
  • inhibitors of lipid and membrane synthesis for example (10.01) biphenyl, (10.02) chloroneb, (10.03) diclorane, (10.04) edifenphos, (10.05) etridiazole, (10.06) iodocarb, (10.07) Iprobenfos, (10.08) isoprothiolane , (10.09) Propamocarb, (10.10) Propamocarb hydrochloride, (10.11) Prothiocarb, (10.12) Pyrazophos, (10.13) Quintozene, (10.14) Tecnazene, (10.15) Tolclofos-methyl.
  • inhibitors of melanin biosynthesis for example (11.01) carpropamide, (11.02) diclocymet, (1.03) fenoxanil, (11.04) phthalide, (11.05) pyroquilone, (11.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl
  • inhibitors of signal mediation for example (13.01) chlozolinate, (13.02) fenpiclonil, (13.03) fludioxonil, (13.04) iprodione, (13.05) procymidone, (13.06) quinoxyfen, (13.07) vinclozoline, (13.08) proquinazide.
  • the compounds of formula (I) may be combined with biological pesticides.
  • biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that can be used or used as biological pesticides are: Adoxophyes orana (Apple peel winder) Granulosis virus (GV), Cydia pomonella (codling moth) Granulosis virus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus (NPV), Spodoptera exigua (mNPV), Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis (African Cotton worm) NPV. It also includes bacteria and fungi that are added as 'inoculant' plants or parts of plants or plant organs and promote by their special properties, plant growth and plant health. Examples are:
  • Agrobacterium spp. Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp.
  • plant extracts and those products formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
  • the compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -l-oxa 4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 52836-31-4). Plants and plant
  • plants are understood as meaning all plants and plant populations, such as desired and undesired ones Wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybean, potato, sugar beets, sugar cane, tomatoes, peas and other vegetables, cotton, tobacco, rapeseed, and Fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, nebulizing, spreading, spreading, indexing and in the case of nutrient material, in particular in the case of seeds, by further single or multi-layered sheathing.
  • plants and their parts can be treated according to the invention.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.
  • Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.
  • PV plants are understood as meaning plants with new properties ("traits”) have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the preferred plants or plant cultivars to be treated according to the invention which are to be treated include all plants which, as a result of the gene-technological modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased Tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salinity, increased flowering efficiency, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvest products.
  • Such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, caused for example by toxins formed in the plants, in particular those caused by the genetic material from Bacillus Thuringiensis (eg by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, also an increased resistance of the plants against Phytopathogenic fungi, bacteria and / or viruses, eg by systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, and increased tolerance of the plants against certain herbicidal active ingredients, such as imidazolinones, sulfonylureas, glyphosate or phosphinotric
  • transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
  • the treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, evaporating, atomising, atomizing, sprinkling, foaming, brushing, spreading, injecting, pouring, drip irrigation and propagating material, in particular in the case of seeds further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to dispense the compounds of formula (I) by the ultra-low-volume method or the use form or the compound of formula ( I) inject myself into the soil.
  • a preferred direct treatment of the plants is foliar application, ie compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be adjusted to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system. The treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant.
  • the present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I).
  • the method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
  • the invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I). The invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner. The invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner. In the case of seed which has been treated at different times with a compound of formula (I) and mixing partner, the individual substances may be contained in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture partners may optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating.
  • the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • a compound of the formula (I) acts systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
  • Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • the compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soya, cotton, canola, oilseed rape and rice are examples of seeds of cereals (eg wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice.
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed can also be used, which after drying, for example, was treated with water and then dried again, for example priming.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation.
  • suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.
  • formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solution or Diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • conventional additives such as conventional extenders and solution or Diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • polyvinylpyrrolidone polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
  • the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • animal parasites in particular ectoparasites or endoparasites.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects and acarids.
  • the compounds of formula (I) which have a favorable toxicity to warm-blooded animals, are suitable for the control of parasites used in animal breeding and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and pets occur. They are effective against all or individual stages of parasite development.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and shellfish, e.g. in aquaculture and also insects like bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians and aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
  • control means that the compounds of formula (I) effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent can. More specifically, “combating” in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication.
  • the arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp.,
  • arthropods include:
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Omithodorus spp., Otobius spp., From the family Ixodidae, such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Omithodorus spp., Otobius spp.
  • Ixodidae such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp.,
  • Parasitic protozoa include:
  • Mastigophora such as Trypanosomatidae, for example Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, such as Trichomonadidae, for example Giardia lamblia, G. canis;
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .; Apicomplexa (Sporozoa), such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis,
  • Toxoplasmadidae for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; such as Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P. falciparum, P. malariae, P.
  • P.vivax P.spec, such as piroplasmea, for example Babesia argentina, B.bovis, B.canis, B.spec, Theileriaparva, Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec.
  • Pathogenic endoparasites which are helminths, include flatworms (e.g., Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include:
  • Monogenea e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .; Cestodes: from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp.
  • Taenia spp. Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
  • Trematodes from the genus Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle
  • Roundworms Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp .; from the order Tylenchida for example: Micronema spp., Strongyloides spp .; from the order Rhabditida, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp.
  • Stephanurus spp. Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.
  • Parelaphostrongylus spp. Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp , Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia s
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
  • Pentastoma from the order Porocephalida for example Linguatula spp ..
  • the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations.
  • the administration can be prophylactic or therapeutic.
  • one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
  • Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent.
  • Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.
  • a further aspect in turn relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide.
  • Another aspect relates to the use of a compound of the formula (I) as anticancer drug, in particular an arthropodicide such as an insecticide or acaricide, for example in animal husbandry, in animal husbandry, in stables or in the hygiene sector.
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes).
  • Examples of vectors and their transmitted diseases or pathogens are:
  • Anopheles malaria, filariasis
  • - Aedes yellow fever, dengue fever, filariasis, other viral diseases
  • - Simulia transmission of worms, in particular Onchocerca volvulus
  • flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
  • Ticks Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).
  • vectors in the context of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • Compounds of formula (I) are suitable for use in the prevention of disease or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials.
  • the compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of formula (I) are present as a ready-to-use pest control agent, that is, it can be applied to the corresponding material without further changes.
  • insecticides or as fungicides in particular the above-mentioned in question are present as a ready-to-use pest control agent, that is, it can be applied to the corresponding material without further changes.
  • the compounds of the formula (I) can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, in closed Rooms, such as homes, factories, offices, vehicle cabs occur.
  • the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients.
  • they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • Application is for example in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cushions and moth gels, as granules or dusts, in litter or bait stations.
  • Pump and atomizer sprays e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cushions and moth gels, as granules or dusts, in litter or bait stations.
  • the 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity ⁇ ; 82 (intensity 2);; ⁇ ; (intensity ⁇ ;; ⁇ ⁇ (intensity n ))
  • 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 For broad signals, several peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.
  • the lists of 1H NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation. In addition, they can, like classical 1H-NMR prints solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities.
  • 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 the particular preparation process. Their peaks can thus help to detect the reproduction of our manufacturing process by "by-product fingerprints.”
  • An expert calculating the peaks of the target compounds by known methods 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.

Abstract

The invention relates to novel bicyclic compounds, to agents containing said compounds, to the use thereof for controlling animal pests and to methods and intermediate products for the production thereof.

Description

Bicyclische Verbindungen als Schädlingsbekämpfungsmittel  Bicyclic compounds as pesticides
Die vorliegende Anmeldung betrifft neue bicyclische Verbindungen, Mittel enthaltend diese Verbindungen, ihre Verwendung zur Bekämpfung von tierischen Schädlingen sowie Verfahren und Zwischenprodukte zu Ihrer Herstellung. In WO 2012/102387 AI sind heterocyclische Verbindungen beschrieben, die insbesondere als Insektizide und Akarizide verwendet werden können. The present application relates to novel bicyclic compounds, agents containing these compounds, their use for combating animal pests and methods and intermediates for their preparation. In WO 2012/102387 Al heterocyclic compounds are described, which can be used in particular as insecticides and acaricides.
Kürzlich sind bicyclische Verbindungen bekannt geworden, die Insektizide Eigenschaften besitzen (WO 2015/038503 AI) Recently, bicyclic compounds have become known which possess insecticidal properties (WO 2015/038503 A1)
In Indian Journal of Chemistry (1973), 11(11), 1112-1114, in Chemical & Pharmaceutical Bulletin (1977), 25(11), 3056-3060, in Gazzetta Chimica Italiana (1982), 112(7-8), 249-254 und in Journal of Organic Chemistry (2013), 78(4), 1471-1477 wird über die Synthese von hetarylsubstituierten Benzothiazolen bzw. Benzoxazolen berichtet. Indian Journal of Chemistry (1973), 11 (11), 1112-1114, Chemical & Pharmaceutical Bulletin (1977), 25 (11), 3056-3060, Gazzetta Chimica Italiana (1982), 112 (7-8) , 249-254 and Journal of Organic Chemistry (2013), 78 (4), 1471-1477, reports the synthesis of hetaryl-substituted benzothiazoles and benzoxazoles, respectively.
In Yaoxue Xuebao (2013), 48(1), 83-88 sind hetarylsubstituierte Benzothiazole beschrieben, für die Anti-Tumor-Eigenschaften in zellulären Assays beschrieben werden. In EP 0 334 289 AI wird über Benzoxazol-6-one und Analoga als Immunsuppressiva und Neoplasmainhibitoren berichtet. In WO 2000/055126 A2 werden Benzoxazole als Proteaseinhibitoren beschrieben. Yaoxue Xuebao (2013), 48 (1), 83-88 describes hetaryl-substituted benzothiazoles for which anti-tumor properties are described in cellular assays. EP 0 334 289 A1 reports benzoxazole-6-ones and analogs as immunosuppressants and neoplasms inhibitors. WO 2000/055126 A2 describes benzoxazoles as protease inhibitors.
Moderne Pflanzenschutzmittel müssen vielen Anforderungen genügen, beispielsweise in Bezug auf Höhe, Dauer und Breite ihrer Wirkung und möglichen Verwendung. Es spielen Fragen der Toxizität, der Kombinierbarkeit mit anderen Wirkstoffen oder Formulierhilfsmitteln eine Rolle sowie die Frage des Aufwands, der für die Synthese eines Wirkstoffs betrieben werden muss. Ferner können Resistenzen auftreten. Schon aus all diesen Gründen kann die Suche nach neuen Pflanzenschutzmitteln nicht als abgeschlossen betrachtet werden und es besteht ständig Bedarf an neuen Verbindungen mit gegenüber den bekannten Verbindungen zumindest in Bezug auf einzelne Aspekte verbesserten Eigenschaften. Modern plant protection products have to meet many requirements, for example with regard to the amount, duration and breadth of their effect and possible use. Issues of toxicity, of the ability to be combined with other active substances or formulation auxiliaries play a role, as well as the question of the effort that has to be spent on the synthesis of an active substance. Furthermore, resistances can occur. For all these reasons, the search for new pesticides can not be considered complete and there is a constant need for new compounds with improved properties compared to the known compounds, at least with regard to individual aspects.
Aufgabe der vorliegenden Erfindung war es, Verbindungen bereitzustellen, durch die das Spektrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten verbreitert wird. The object of the present invention was to provide compounds which broaden the spectrum of pesticides from various aspects.
Gelöst wird die Aufgabe, sowie weitere nicht explizit genannte Aufgaben, die aus den hierin diskutierten Zusammenhängen ableitbar oder erschließbar sind, durch Verbindungen der Formel (I) The problem is solved, as well as other tasks not explicitly mentioned, which can be derived or deduced from the relationships discussed herein, by compounds of the formula (I)
in welcher in which
A für einen A-Rest aus der Reihe (A-b) bis (A-f) A for an A radical from the series (A-b) to (A-f)
(A-b) (A-c) (A-d) (A-e) (A-f) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet und  (A-b) (A-c) (A-d) (A-e) (A-f) wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of the formula (I) and
B für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyl steht, B is a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
Q für Sauerstoff oder Schwefel steht, Q stands for oxygen or sulfur,
R1 für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkoxy und Cyano steht, R2 a) für einen B-Rest aus der Reihe R 1 is a radical from the series hydrogen, alkyl, alkoxy and cyano, R 2 a) is a B radical from the series
(B-5) (B-6) B-7) (B-8) (B-5) (B-6) B-7) (B-8)
(B-9) B-10) (B-l l) (B-12) (B-9) B-10) (Bl l) (B-12)
(B-13) (B-14) (B-15) (B-16) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder (B-13) (B-14) (B-15) (B-16) wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R b) für einen D-Rest aus der Reihe (D- 1 ) bis (D-3) R b) for a D radical from the series (D-1) to (D-3)
(D-1 ) (D-2) (D-3) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder c) für einen Rest der Formel  (D-1) (D-2) (D-3), wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or c) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder d) für einen Rest der Formel  wherein the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or d) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R2 e) für einen F-Rest aus der Reihe (F-l) bis (F-l l) „ in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I), or R 2 e) represents an F radical from the series (F1) to (F1) "
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R2 f) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder in which the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or R 2 f) represents a radical of the formula wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R2 g) für gegebenenfalls substituiertes Phenyl steht, worin für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, Alkyl, Halogenalkyl, gegebenenfalls substituiertes und gegebenenfalls durch ein oder mehrere Heteroatome unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, halogeniertes Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Bis(alkoxy)alkyl,R 2 g) is optionally substituted phenyl, wherein is hydrogen or a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, optionally substituted and optionally interrupted by one or more heteroatoms saturated or unsaturated cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated Alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, bis (alkoxy) alkyl,
Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl, Alkoxy(alkylsulfinyl)alkyl,Bis (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl, alkoxy (alkylsulfinyl) alkyl,
Alkoxy(alkylsulfonyl)alkyl, Bis(alkylsulfanyl)alkyl, Bis(halogenalkylsulfanyl)alkyl,Alkoxy (alkylsulfonyl) alkyl, bis (alkylsulfanyl) alkyl, bis (haloalkylsulfanyl) alkyl,
Bis(hydroxyalkylsulfanyl)alkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, alpha-Hydroxyimino- alkoxycarbonylalkyl, alpha-Alkoxyimino-alkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl,die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Alkyl, Halogenalkyl, Alkoxy und Alkoxyalkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Alkyl und Halogenalkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthio, Alkylthioalkyl und Cycloalkyl) und die Heteroarylalkylreste Triazolylalkyl, Pyridylalkyl, Pyrimidylalkyl und Oxadiazolylalkyl (welche selbst wiederum substituiert sein können durch Halogen und Alkyl) steht, oder für einen C-Rest aus der Reihe (C-l) bis (C-9) Bis (hydroxyalkylsulfanyl) alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyiminoalkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, morpholinyl, Triazolinonyl, oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl , Dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may themselves be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which in turn may be substituted by halogen, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals pyridyl, pyridyl-N oxide, pyrimidyl, imi dazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may be substituted by halo, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio , Alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which in turn may themselves be substituted by halogen and alkyl), or represents a C radical from the series (Cl) to (C-9)
X (C-9) X (C-9)
R8 steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, R 8 is where the dotted line represents the bond to the B residues,
X für Sauerstoff oder Schwefel steht,  X is oxygen or sulfur,
X1 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, X 1 is a radical selected from among hydrogen, halogen, cyano, nitro, alkyl, haloalkyl,
Cycloalkyl, Alkoxy und Halogenalkoxy steht,  Cycloalkyl, alkoxy and haloalkoxy,
X2 für Sauerstoff, Schwefel, NR5 oder NOH steht, X 2 is oxygen, sulfur, NR 5 or NOH,
L für Sauerstoff oder Schwefel steht, L is oxygen or sulfur,
V-Z für R24CH-CHR25 oder R24C=CR25 steht, n für 1 oder 2 steht, m für 1 , 2, 3 oder 4 steht, VZ is R 24 CH-CHR 25 or R 24 C = CR 25 , n is 1 or 2, m is 1, 2, 3 or 4,
R für NR18R19 oder für einen jeweils gegebenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkyl-S-alkyl, Alkyl-S(0)-alkyl, Alkyl-S(0)2-alkyl, R18-CO-alkyl, NR18R19-CO-alkyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkenylalkyl, Heterocyclyl, Heterocyclylalkyl, Phenyl, Phenylalkyl, Hetaryl und Hetarylalkyl steht, R is NR 18 R 19 or represents a respectively optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S (0) -alkyl, alkyl-S (0) 2 alkyl, R 18 -CO-alkyl, NR 18 R 19 is -CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl,
R3 für Wasserstoff oder Alkyl steht, R 3 is hydrogen or alkyl,
R4 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, R5 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder R 4 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl, R 5 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
R3 und R4 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, oder R 3 and R 4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, or
R3 und R5 gemeinsam mit den Stickstoffatomen, an die sie gebunden sind, einen Ring bilden, R6 für Wasserstoff oder Alkyl steht, R 3 and R 5 together with the nitrogen atoms to which they are attached form a ring, R 6 is hydrogen or alkyl,
R7 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder R 7 is a radical selected from hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, R 6 and R 7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
R8 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkoxy, Halogenalkoxy, Alkenyl, Alkoxyalkyl, jeweils gegebenenfalls durch Halogen substituiertes Alkylcarbonyl und Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonyl und gegebenenfalls durch Halogen, Alkyl, Alkoxy, Halogenalkyl und Cyano substituiertes Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch Alkyl oder Arylalkyl substituiertes Ammonium-Ion steht, R 8 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl and optionally by halogen, alkyl, alkoxy, haloalkyl and cyano is substituted cycloalkylcarbonyl, or represents a cation or an optionally substituted by alkyl or arylalkyl ammonium ion,
R9 für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 9 is a radical from the series in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
8 9 8 9
R und R in den Resten (C-l) und (F-l) auch zusammen mit der N-S(0)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R für Wasserstoff oder Alkyl steht, R and R in the radicals (Cl) and (Fl) may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the or a plurality of further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group, R is hydrogen or alkyl,
R8 und R10 in den Resten (C-2) und (F-2) auch gemeinsam mit den N- Atomen an die sie gebunden sind, für einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring stehen können, der mindestens ein weiteres Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R 8 and R 10 in the radicals (C-2) and (F-2) may also together with the N atoms to which they are bonded represent a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the at least one further heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
9 10 9 10
R und R in den Resten (C-2) und (F-2) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R and R in the radicals (C-2) and (F-2) may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
RU für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht, R U is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio stands,
12 12
R für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht,  R represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio .
11 12 11 12
R und R in den Resten (C-3) und (F-3) auch gemeinsam mit dem Phosphoratom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 5- bis 7-gliedrigen Ring bilden können, der ein oder zwei Heteroatome aus der Reihe Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Schwefel enthalten kann,  R and R in the radicals (C-3) and (F-3) may also together with the phosphorus atom to which they are attached form a saturated or unsaturated and optionally substituted 5- to 7-membered ring, one or two Heteroatoms from the series oxygen (oxygen atoms may not be immediately adjacent) and may contain sulfur,
13 13
R für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,  R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
14 14
R für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,  R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R15 für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 15 is a radical from the series each optionally substituted alkyl, alkenyl and alkynyl, each optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be included, respectively substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R8 und R15 in den Resten (C-6) und (F-6) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel,R 8 and R 15 in the radicals (C-6) and (F-6) also together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring can form one or more other heteroatoms from the series sulfur,
Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, Oxygen (where oxygen atoms are not immediately adjacent) and may contain nitrogen and / or at least one carbonyl group, a radical selected from the group consisting of hydrogen, each optionally substituted alkyl, alkoxy, alkenyl and alkynyl, respectively optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in in which each of the rings is at least one heteroatom selected from the group consisting of sulfur, oxygen (where oxygen atoms are not immediately adjacent) and nitrogen, optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R" und R16 in den Resten (C-7) und (F-7) auch zusammen mit dem N-Atom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R8 und R17 in den Resten (C-8) und (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R18 für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkylcarbonyl, Alkoxycarbonyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl und Cycloalkenylalkyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Arylalkyl, Heteroaryl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R " and R 16 in the radicals (C-7) and (F-7) together with the N-atom to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or more other heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group, a radical from the series each optionally substituted alkyl, alkoxy, alkenyl and alkynyl, respectively optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl in which the rings may contain at least one heteroatom selected from sulfur, oxygen (where oxygen atoms are not immediately adjacent) and nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group R 8 and R 17 in the radicals (C-8) and (F-8) also together with the NC (X) group to which they are attached may form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or more further heteroatoms selected from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent ) and nitrogen and / or at least one carbonyl group, R 18 is a radical selected from hydrogen, hydroxy, each optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, each optionally substituted Cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the rings at least one Heteroatom from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group,
R19 für einen Rest aus der Reihe Wasserstoff, für ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch Ci-C i-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl und Alkylsulfonylalkyl steht, R 19 is a radical selected from the group consisting of hydrogen, an alkali metal or alkaline earth metal ion or an optionally monosubstituted to trisubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or an optionally halogen or cyano-substituted radical from the series consisting of alkyl, alkoxy, Alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl,
Y1 und Y2 unabhängig voneinander für C=0 oder S(0)2 stehen, Y 1 and Y 2 independently of one another represent C = 0 or S (O) 2,
Y3 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und NR20R21 steht, Y 3 is a radical from the group consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR 20 R 21 ,
W für einen Rest aus der Reihe O, S, SO und SO2 steht, W is a radical from the series O, S, SO and SO2,
R22 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkenyl, Halogenalkenyl, Alkinyl, Halogenalkinyl, Alkoxy, Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Alkoxyalkyl, gegebenenfalls durch Halogen substituiertes Bis(alkoxy)alkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfanylalkyl, gegebenenfalls durch Halogen substituiertes Alkylcarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfinylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfonylalkyl, Dialkylaminosulfanylalkyl, Dialkylaminosulfinylalkyl, Dialkylaminosulfonylalkyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkinyloxy, gegebenenfalls durch Halogen substituiertes Alkinyloxycarbonyl, Dialkylaminocarbonyl, N-Alkyl-N-Cycloalkylaminocarbonyl, Dialkylaminocarbonylalkyl, N-Alkyl-N-Cycloalkylaminocarbonylalkyl, Heterocyclyl- carbonylalkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkylalkyl, gegebenenfalls substituiertes Heterocyclyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclylalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist)Alkoxy oder Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Amino, Alkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Halogenalkyl, Alkoxy oder Halogenalkoxy substituiertes Arylalkyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetarylalkyl steht, oder für einen D-Rest aus der Reihe (D-l) bis (D-3) R 22 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis (alkoxy) alkyl, optionally halogen-substituted alkylsulfanylalkyl, alkylcarbonylalkyl optionally substituted by halogen, optionally alkyl substituted by halogen, alkylsulphonylalkyl optionally substituted by halogen, dialkylaminosulphanylalkyl, dialkylaminosulphinylalkyl, dialkylaminosulphonylalkyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-substituted alkoxycarbonylalkyl, optionally halogen-substituted alkynyloxy, optionally halogen-substituted alkynyloxycarbonyl, dialkylaminocarbonyl, N-alkyl-N-cycloalkylaminocarbonyl, dialkylaminocarbonylalkyl, N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonyl lalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, optionally substituted by halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkyl optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkylcarbonyl, optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, Cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, Hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, Alkylcarbonyl, alkoxycarbonyl or aminocarbonyl-substituted heterocyclylalkyl, optionally substituted by halogen, cyano, nitro, hydroxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted) alkoxy or haloalkoxy-substituted aryl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, Hydroxy, amino, alkyl, cycloalkyl (which is optionally substituted), haloalkyl, alkoxy or haloalkoxy-substituted arylalkyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy , Haloalkoxy, alkylth io, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl-substituted hetarylalkyl, or a D radical from the series (D1) to (D-3)
(D-1 ) (D-2) (D-3) für einen E-Rest aus der Reihe (E-l) bis (E-l 1) (D-1) (D-2) (D-3) for an E group from the series (El) to (El 1)
E-26 - 14 - E-26 - 14 -
E-37 E-38 E-39 E-40  E-37 E-38 E-39 E-40
E-44 E-45 E-46 E-47 E-44 E-45 E-46 E-47
E-48 E-49 E-50 E-51 steht, oder  E-48 E-49 E-50 E-51 stands, or
im Fall, dass R2 für einen der Reste unter d) steht in the case where R 2 is one of the radicals under d)
auch für einen E-Rest aus der Reihe E-12 bis E-17  also for an E-rest from the series E-12 to E-17
steht, für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy und jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylcarbonyloxy, Alkenylcarbonyloxy, Alkinylcarbonyloxy, Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Alkylsulfonyloxy, Alkylamino, Alkenylamino, Alkinylamino, Cycloalkylamino, Alkylthio, Halogenalkylthio, Alkenylthio, Alkinylthio, Cycloalkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylcarbonyl, Alkoxyiminoalkyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, is a radical selected from among hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy , Alkylsulfonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Dialkylaminocarbonyl, Aminothiocarbonyl, Alkylaminosulfonyl, Alkylsulfonylamino, Alkylcarbonylamino, Alkenylcarbonylamino, Alkinylcarbonylamino, Cycloalkylcarbonylamino, Alkoxycarbonylamino, Alkylthiocarbonylamino, Bicycloalkyl, Aryl, Aryloxy, Heteroaryl und Heteroaryloxy steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl und Halogenalkyl, für einen Rest aus der Reihe Wasserstoff, Alkyl, Cycloalkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Cyanoalkyl, Alkylcarbonyl, Alkenylcarbonyl, Halogenalkylcarbonyl, Halogenalkenylcarbonyl, Alkoxyalkyl, Alkoxycarbonyl, Alkylsulfonyl und Halogenalkylsulfonyl steht, für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylthioalkyl, Alkenylthioalkyl, Cyanoalkyl und Alkoxyalkyl steht oder, im Fall, dass R2 für einen der Reste unter c) oder f) steht und R23 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, und für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht und für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht, für Wasserstoff oder Alkyl steht und Dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, wherein the substituents are independently selected from halo, cyano, nitro, hydroxy, amino, alkyl and haloalkyl, a radical selected from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl, a radical selected from the group consisting of hydrogen, Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl and alkoxyalkyl or, in the case where R 2 is one of the radicals under c) or f) and R 23 is taken together with the nitrogen to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, and represents hydrogen or an optionally substituted radical selected from alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and is hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, is hydrogen or alkyl and
R für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy-alkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl Cyanoalkyl steht, und Verbindungen der Formel (I), in welcher A für den A-Rest (A-a) R is a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, Haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cyanoalkyl, and compounds of the formula (I) in which A is the A radical (Aa)
T  T
(A-a) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet und  (A-a), wherein the dotted line represents the bond to the carbon atom of the bicyclic of the formula (I), and
G1 für N oder C-B1 steht, G 1 is N or CB 1 ,
B1 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyl steht, B 1 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
B2 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyl steht, B 2 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
T für Sauerstoff oder ein Elektronenpaar steht, T is oxygen or a pair of electrons,
Q für Sauerstoff oder Schwefel steht, Q stands for oxygen or sulfur,
R1 für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkoxy und Cyano steht, R 1 is a radical selected from the group consisting of hydrogen, alkyl, alkoxy and cyano,
R2 a) für einen der folgenden B-Reste R 2 a) for one of the following B radicals
(B-5) (B-6) (B-7) (B-8) (B-5) (B-6) (B-7) (B-8)
(B-9) (B-10) (B-l l) (B-12) - 18 - (B-9) (B-10) (B1) (B-12) - 18 -
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, Alkyl, Halogenalkyl, gegebenenfalls substituiertes und gegebenenfalls durch ein oder mehrere Heteroatome unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, halogeniertes Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Halogenalkylthioalkyl, in which the dashed line represents the bond to the carbon atom of the bicyclic compound of the formula (I) in which hydrogen or a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, optionally substituted and optionally saturated or unsaturated cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, haloalkylthioalkyl interrupted by one or more heteroatoms,
Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl Bis(alkoxy)alkyl, Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl, Alkoxy(alkylsulfinyl)alkyl, Alkoxy(alkylsulfonyl)alkyl,Haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, bis (alkoxy) alkyl, bis (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl, alkoxy (alkylsulfinyl) alkyl, alkoxy (alkylsulfonyl) alkyl,
Bis(alkylsulfanyl)alkyl, Bis(halogenalkylsulfanyl)alkyl, Bis(hydroxyalkylsulfanyl)alkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, alpha-Hydroxyimino-alkoxycarbonylalkyl, alpha- Alkoxyimino-alkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Alkyl, Halogenalkyl, Alkoxy und Alkoxyalkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Alkyl und Halogenalkyl), die Heteroarylreste Pyridyl, Pyridy-N-oxid, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthio, Alkylthioalkyl und Cycloalkyl) und die Heteroarylalkylreste Triazolylalkyl, Pyridylalkyl, Pyrimidylalkyl und Oxadiazolylalkyl (welche selbst wiederum substituiert sein können durch Halogen und Alkyl) steht, oder aa) für einen der folgenden B-Reste Bis (alkylsulfanyl) alkyl, bis (haloalkylsulfanyl) alkyl, bis (hydroxyalkylsulfanyl) alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyimino-alkoxycarbonylalkyl, alpha-alkoxyimino-alkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio , alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid , Oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which themselves may be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which in turn may itself be substituted by halogen, cyano, nitro, Alkyl and haloalkyl), d The heteroaryl radicals pyridyl, pyridyl-N-oxide, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may be substituted by halogen, nitro, alkyl , Haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which themselves may be substituted by halogen and alkyl), or aa) is one of the following B radicals
(B-3) (B-4) (B-3) (B-4)
(B-25) (B-26) (B-27) (B-25) (B-26) (B-27)
(B-31) (B-32)  (B-31) (B-32)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, wonn für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, gegebenenfalls substituiertes und gegebenenfalls durch ein oder mehrere Heteroatome unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Cycloalkylalkyl, Halogenalkoxy, Alkoxyalkyl, halogeniertes Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Halogenalkylthioalkyl, Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl Bis(alkoxy)alkyl, Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl, in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I), wonn is a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, optionally substituted and optionally interrupted by one or more heteroatoms saturated or unsaturated cycloalkyl, cycloalkylalkyl, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylthioalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, bis (alkoxy) alkyl, bis (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl,
Alkoxy(alkylsulfinyl)alkyl, Alkoxy(alkylsulfonyl)alkyl, Bis(alkylsulfanyl)alkyl,Alkoxy (alkylsulfinyl) alkyl, alkoxy (alkylsulfonyl) alkyl, bis (alkylsulfanyl) alkyl,
Bis(halogenalkylsulfanyl)alkyl, Bis(hydroxyalkylsulfanyl)alkyl, Alkoxycarbonyl,Bis (haloalkylsulfanyl) alkyl, bis (hydroxyalkylsulfanyl) alkyl, alkoxycarbonyl,
Alkoxycarbonylalkyl, alpha-Hydroxyimino-alkoxycarbonylalkyl, alpha- Alkoxyimino- alkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Alkyl, Halogenalkyl, Alkoxy und Alkoxyalkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Alkyl und Halogenalkyl), die Heteroarylreste Imidazolyl, Pyrazolyl, Oxazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl,Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthio, Alkylthioalkyl und Cycloalkyl) und die Heteroarylalkylreste Triazolylalkyl, Pyridylalkyl, Pyrimidylalkyl und Oxadiazolylalkyl (welche selbst wiederum substituiert sein können durch Halogen und Alkyl) steht, oder wenn R für einen der unter a) oder aa) aufgeführten Reste steht, auch für einen C-Rest aus der Reihe Alkoxycarbonylalkyl, alpha-hydroxyimino-alkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio, alkylsulfmyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl , Oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyloxide, oxathiolanyloxide, oxathialpanyloxide, oxathiocanyloxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathienpanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, Dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may themselves be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which itself may be substituted by halogen, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals imidazolyl, pyrazolyl, Oxazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which themselves may be substituted by halo, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which themselves may be substituted by halogen and alkyl), or when R is one of the radicals listed under a) or aa), also represents a C radical from the series
steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, wherein the dashed line indicates the bond to the B radicals,
oder or
R2 c) für einen Rest der Formel R 2 c) is a radical of the formula
X X
U ^  U ^
N  N
1  1
R  R
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R2 d) für einen Rest der Formel wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or R 2 d) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R e) für einen F-Rest aus der Reihe (F-2) bis (F-11)  in which the dashed line denotes the bond to the carbon atom of the bicycle of the formula (I), or R e) represents an F radical from the series (F-2) to (F-11)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder  wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R f) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, R f) is a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
X für Sauerstoff oder Schwefel steht, X is oxygen or sulfur,
X2 für Sauerstoff, Schwefel oder NOH steht, X 2 is oxygen, sulfur or NOH,
L für Sauerstoff oder Schwefel steht, L is oxygen or sulfur,
V-Z für R24CH-CHR25 oder R24C=CR25 steht, n für 1 oder 2 steht, m für 1 , 2, 3 oder 4 steht, R3 für Wasserstoff oder Alkyl steht, VZ is R 24 CH-CHR 25 or R 24 C = CR 25 , n is 1 or 2, m is 1, 2, 3 or 4, R 3 is hydrogen or alkyl,
R4 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder R 4 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl, or
R3 und R4 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, R 3 and R 4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
R6 für Wasserstoff oder Alkyl steht, R 6 is hydrogen or alkyl,
R7 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder R 7 is a radical selected from hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, R 6 and R 7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
R8 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkoxy, Halogenalkoxy, Alkenyl, Alkoxyalkyl, jeweils gegebenenfalls durch Halogen substituiertes Alkylcarbonyl und Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonyl und gegebenenfalls durch Halogen, Alkyl, Alkoxy, Halogenalkyl und Cyano substituiertes Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch Alkyl oder Arylalkyl substituiertes Ammonium-Ion steht, R 8 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl and optionally by halogen, alkyl, alkoxy, haloalkyl and cyano substituted Is cycloalkylcarbonyl, or is a cation or an optionally substituted by alkyl or arylalkyl ammonium ion,
R9 für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 9 is a radical from the series in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R10 für Wasserstoff oder Alkyl steht, R8 und R10 in den Resten (C-2) und (F-2) auch gemeinsam mit den N- Atomen an die sie gebunden sind, für einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring stehen können, der mindestens ein weiteres Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R 10 is hydrogen or alkyl, R 8 and R 10 in the radicals (C-2) and (F-2) to which they are bound together with the N atoms, a saturated or unsaturated and optionally substituted 4- may be to 8-membered ring which may contain at least one further heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
9 10 9 10
R und R in den Resten (C-2) und (F-2) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht, für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht, R and R in the radicals (C-2) and (F-2) may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more other heteroatoms from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group, each of an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, Alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio, represents an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, Alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzy loxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,
11 12 11 12
R und R in den Resten (C-3) und (F-3) auch gemeinsam mit dem Phosphoratom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 5- bis 7-gliedrigen Ring bilden können, der ein oder zwei Heteroatome aus der Reihe Sauerstoff (wobei R and R in the radicals (C-3) and (F-3) may also together with the phosphorus atom to which they are attached form a saturated or unsaturated and optionally substituted 5- to 7-membered ring, one or two Heteroatoms from the series oxygen (where
Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Schwefel enthalten kann, R für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht, Oxygen atoms may not be immediately adjacent) and may contain sulfur, R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
14 14
R für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,  R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R15 für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 15 is a radical from the series each optionally substituted alkyl, alkenyl and alkynyl, each optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R8 und R15 in den Resten (C-6) und (F-6) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R 8 and R 15 in the radicals (C-6) and (F-6) also together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R16 für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 16 is a radical from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings are at least one heteroatom selected from the group consisting of sulfur, oxygen (oxygen atoms not being directly adjacent may each contain) and nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R8 und R16 in den Resten (C-7) und (F-7) auch zusammen mit dem N-Atom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R 8 and R 16 in the radicals (C-7) and (F-7) together with the N-atom to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, which may contain one or more further heteroatoms from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R17 für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R8 und R17 in den Resten (C-8) und (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, und im Fall, dass R2 für einen der unter f) aufgeführten Reste steht, R 17 is a radical from the series in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings are at least one heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and each may contain nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R 8 and R 17 in the radicals (C-8) and (F-8) together with the NC (X) group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring can contain one or more further heteroatoms from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group, and in the case that R 2 is one of the radicals listed under f) .
R22 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkenyl, Halogenalkenyl, Alkinyl, Halogenalkinyl, Alkoxy, Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Alkoxyalkyl, gegebenenfalls durch Halogen substituiertes Bis(alkoxy)alkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfanylalkyl, gegebenenfalls durch Halogen substituiertes Alkylcarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfinylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfonylalkyl, Dialkylaminosulfanylalkyl, Dialkylaminosulfinylalkyl, Dialkylaminosulfonylalkyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkinyloxy, Dialkylaminocarbonylalkyl, N-Alkyl-N-Cycloalkylaminocarbonylalkyl, Heterocyclyl- carbonylalkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkylalkyl, gegebenenfalls substituiertes Heterocyclyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclylalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist)Alkoxy oder Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Amino, Alkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Halogenalkyl, Alkoxy oder Halogenalkoxy substituiertes Arylalkyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetarylalkyl steht, und im Fall, dass R2 für einen der unter c), d) oder f) aufgeführten Reste steht R auch für einen D-Rest aus der Reihe (D-l) bis (D-3) R 22 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis (alkoxy) alkyl, optionally halogen-substituted alkylsulfanylalkyl, optionally substituted by halogen alkylsulfinylalkyl, optionally substituted by halogen alkylsulfinylalkyl, optionally substituted by halogen alkylsulfonylalkyl, dialkylaminosulfanylalkyl, dialkylaminosulfinylalkyl, dialkylaminosulfonylalkyl, optionally halogen substituted alkoxycarbonylalkyl, optionally halogen substituted alkynyloxy, dialkylaminocarbonylalkyl, N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonylalkyl, Alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, if appropriate by halogen, cyano, nitro, alkyl, cycloalkyl, Haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkyl, optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which optionally itself substituted by alkyl or halogen) substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio , Alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl substituted heterocyclylalkyl, optionally all aryl substituted by halogen, cyano, nitro, hydroxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted) alkoxy or haloalkoxy, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, amino, alkyl, cycloalkyl ( which is optionally substituted), haloalkyl, alkoxy or haloalkoxy-substituted arylalkyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl , Alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, Alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl-substituted hetarylalkyl, and in the case where R 2 is one of the radicals listed under c), d) or f), R is also a D. Residue from the series (D1) to (D-3)
(D-1 ) (D-2) (D-3) wonn für NR R oder für einen jeweils gegebenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkyl-S-alkyl, Alkyl-S(0)-alkyl, Alkyl-S(0)2-alkyl, R18-CO-alkyl, NR18R19-CO-alkyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkenylalkyl, Heterocyclyl, Heterocyclylalkyl, Phenyl, Phenylalkyl, Hetaryl und Hetarylalkyl steht, für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy und Halogenalkoxy steht, für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und NR20R21 steht, für einen Rest aus der Reihe S, SO und SO2 steht, (D-1) (D-2) (D-3) wonn for NR R or for an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S (0) - alkyl, alkyl-S (O) 2 -alkyl, R 18 -CO-alkyl, NR 18 R 19 -CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl, for a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy and haloalkoxy, a radical from the series consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR 20 R 21 stands for a remainder of the series S, SO and SO2,
R18 für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkylcarbonyl, Alkoxycarbonyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl und Cycloalkenylalkyl, in welchen die Ringe mindestens einR 18 is a radical selected from the group consisting of hydrogen, hydroxy, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the rings at least one
Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Arylalkyl, Heteroaryl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, für einen Rest aus der Reihe Wasserstoff, für ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch Ci-C i-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl und Alkylsulfonylalkyl steht, und im Fall, dass R2 für einen der unter f) aufgeführten Reste steht auch für einen E-Rest aus der Reihe (E-l) bis (E-l 1) Heteroatom from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group, a radical selected from the group consisting of hydrogen, an alkali metal or alkaline earth metal ion or an optionally monosubstituted to trisubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or an optionally halogen or cyano-substituted radical from the series consisting of alkyl, alkoxy, alkoxyalkyl, Alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl, and in the case that R 2 is one of the radicals listed under f) is also an E radical from the series (El) to (El 1)
und (E-l 8) bis (E-51) and (El 8) to (E-51)
E-22 E-23 E-24 E-25 E-22 E-23 E-24 E-25
E-27 E-28 E-29 E-30 E-27 E-28 E-29 E-30
E-32 E-33 E-34 E-32 E-33 E-34
E-35 E-36 E-35 E-36
E-37 E-38 E-39 E-40  E-37 E-38 E-39 E-40
E-44 E-45 E-46 E-47  E-44 E-45 E-46 E-47
E-48 E-49 E-50 E-51 steht,  E-48 E-49 E-50 E-51 stands,
R20 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy und jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylcarbonyloxy, Alkenylcarbonyloxy,R 20 is a radical selected from among hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy,
Alkinylcarbonyloxy, Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Alkylsulfonyloxy, Alkylamino, Alkenylamino, Alkinylamino, Cycloalkylamino, Alkylthio, Halogenalkylthio, Alkenylthio, Alkinylthio, Cycloalkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylcarbonyl, Alkoxyiminoalkyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Aminothiocarbonyl, Alkylaminosulfonyl, Alkylsulfonylamino,Alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulphonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino,
Alkylcarbonylamino, Alkenylcarbonylamino, Alkinylcarbonylamino, Cycloalkylcarbonylamino, Alkoxycarbonylamino, Alkylthiocarbonylamino, Bicycloalkyl, Aryl, Aryloxy, Heteroaryl und Heteroaryloxy steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl und Halogenalkyl, R für einen Rest aus der Reihe Wasserstoff, Alkyl, Cycloalkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Cyanoalkyl, Alkylcarbonyl, Alkenylcarbonyl, Halogenalkylcarbonyl, Halogenalkenylcarbonyl, Alkoxyalkyl, Alkoxycarbonyl, Alkylsulfonyl und Halogenalkylsulfonyl steht, Alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, wherein the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, alkyl and haloalkyl, R is a radical the series hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, Haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl,
R23 für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylthioalkyl, Alkenylthioalkyl, Cyanoalkyl und Alkoxyalkyl steht oder, wenn für R2 für einen der unter f) aufgeführten Reste steht, R 23 is a radical from the series consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl and alkoxyalkyl or, if R 2 is one of the radicals listed under f) stands,
R22 und R23 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, und R 22 and R 23 together with the nitrogen atom to which they are attached form a ring which may contain one or more other nitrogen, oxygen and sulfur heteroatoms, and
24 24
R für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht und R is hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and
25 25
R für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,  R is hydrogen or an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R27 für Wasserstoff oder Alkyl steht und R26 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy-alkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl und Cyanoalkyl steht. R 27 is hydrogen or alkyl and R 26 is a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and Cyanoalkyl stands.
Weiterhin wurde gefunden, dass die Verbindungen der Formel (I) und auch diejenigen in der Tabelle 1 aufgeführten Verbindungen, die nicht unter die Formel (I) fallen eine gute Wirksamkeit als Schädlingsbekämpfungsmittel, beispielsweise gegen Arthropoden und insbesondere Insekten, besitzen und darüber hinaus in der Regel insbesondere gegenüber Kulturpflanzen sehr gut pflanzenverträglich sind und/oder über günstige toxikologische und/oder günstige umweltrelevante Eigenschaften verfügen. It has furthermore been found that the compounds of the formula (I) and also those compounds listed in Table 1 which do not fall under the formula (I) have good activity as pesticides, for example against arthropods and in particular insects, and furthermore in US Pat Rule especially with respect to crop plants are very good plant compatibility and / or have favorable toxicological and / or favorable environmental properties.
Vorzugsbereich (1): Bevorzugt sind Verbindungen der Formel (I), in welchen A für einen der folgenden A-Reste Preferred range (1): Preference is given to compounds of the formula (I) in which A is one of the following A radicals
(A-b) (A-f) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, und (Down) (af) wherein the dashed line represents the bond to the carbon atom of the bicyclic of the formula (I), and
für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C6-Alkyl und Ci-C i-Halogenalkyl steht, für Schwefel steht,  a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C -haloalkyl, represents sulfur,
für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl und Ci-C6-Alkoxy steht,  represents a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy,
a) für einen der folgenden B-Reste  a) for one of the following B radicals
(B-5) (B-6) B-7) (B-8)  (B-5) (B-6) B-7) (B-8)
(B-25) (B-26) (B-27) (B-28) (B-25) (B-26) (B-27) (B-28)
(B-33) (B-34) (B-35) (B-36) (B-37)  (B-33) (B-34) (B-35) (B-36) (B-37)
(B-38) (B-39) (B-40) (B-41 ) (B-38) (B-39) (B-40) (B-41)
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder ) für einen D-Rest aus der Reihe (D- 1 ) bis (D-3) (B-42) (B-43) (B-44) (B-45), wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or) represents a D radical of the series ( D-1) to (D-3)
(D-1 ) (D-2) (D-3) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder c) für einen Rest der Formel  (D-1) (D-2) (D-3), wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or c) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder d) für einen Rest der Formel wherein the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or d) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder für einen F-Rest aus der Reihe (F-l), (F-8), (F-10) und (F-l 1) in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I), or for an F radical from the series (F1), (F-8), (F-10) and (F1)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder f) für einen Rest der Formel in which the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or f) a radical of the formula
22 22
-R  -R
23 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder g) für einen Rest der Formel  23, wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or g) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin für Wasserstoff oder für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, C1-C4- Alkylamino, Halogen-Ci-C4-alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkyl, Halogen-Ci-C4- alkyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy, in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I) in which, for hydrogen or a radical from the series, halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno-C 1 -C 4 -alkylamino , di (Ci-C4-alkyl) amino, Ci-C4-alkyl, halo-Ci-C4- alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C3-C6 cycloalkyl C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy,
Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, halogeniertes Ci-C4-Alkoxy-Ci-C4-alkyl, Bis(Ci-C4-alkoxy)-Ci-C4-alkyl, Bis(halogen-Ci-C4-alkoxy)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfinyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci- C4-alkylsulfonyl)-Ci-C4-alkyl, Bis(Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(halogen-Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Bis(hydroxy-Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl,Halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, Bis (halogeno-C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 - alkylsulfanyl) -CC-C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfinyl) -Ci-C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfonyl) -Ci-C 4 alkyl, bis (C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, bis (halogeno-C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, bis (hydroxy-C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl alkyl, C 1 -C 4 -alkoxycarbonyl,
Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, a//jAfl-Hydroxyimino-C 1 -C4-alkoxycarbonyl-C 1 -C4-alkyl, fl^Afl-Ci-C4-Alkoxy-imino-Ci-C4-alkoxycarbonyl-Ci-C4-alkyl, C(X2)NR3R4, NR6R7, C1-C4- Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylthio, C1-C4- Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyl- dioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxy und Ci-C4-Alkoxy-Ci-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Ci-C4-Alkyl und Halogen-Ci-C4-alkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxy, Halogen-Ci-C4- alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkylthio, Ci-C4-Alkylthio-Ci-C4-alkyl und C3-C6- Cycloalkyl) und die Heteroaryl-Ci-C4-alkylreste Triazolyl-Ci-C4-alkyl, Pyridyl-Ci-C4-alkyl, Pyrimidyl-Ci-C4-alkyl und Oxadiazolyl-Ci-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und Ci-C4-Alkyl) steht, oder für einen C-Rest aus der Reihe (C-l) und (C-6) bis (C-9)C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, α-αA-hydroxyimino-C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-imino-C 1 -C 4 -alkoxycarbonyl -C-C 4 alkyl, C (X 2) NR 3 R 4, NR 6 R 7, C 1 -C4- alkylthio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylthio , C1-C4 haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, the heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid , Oxathiepanyldioxid, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may be substituted by Ci-C4-alkyl, halo-Ci-C4-alkyl, Ci-C4-alkoxy and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl), phenyl (which in turn may itself be substituted by halogen, cyano, nitro , C 1 -C 4 -alkyl and halogen-C 1 -C 4 -alkyl), the heteroaryl radicals pyridyl, pyridyl-N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, Triazinyl, tetrazinyl and isoquinolinyl (which in turn may themselves be substituted by halogen, nitro, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 - alkoxy-Ci-C4-alkyl, Ci-C 4 alkylthio, Ci-C4-alkylthio-Ci-C 4 alkyl and C 3 -C 6 - cycloalkyl) and the heteroaryl Ci-C4-alkyl radicals triazolyl-Ci -C4-alkyl, pyridyl-C 1 -C 4 -alkyl, pyrimidyl-C 1 -C 4 -alkyl and oxadiazolyl-C 1 -C 4 -alkyl (which in turn may themselves be substituted by halogen and C 1 -C 4 -alkyl), or a C Radical from the series (Cl) and (C-6) to (C-9)
steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C6-Alkyl und Ci-C6-Halogenalkyl steht, X für Sauerstoff oder Schwefel steht, in which the dashed line denotes the bond to the B radicals, a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl, X is oxygen or sulfur,
XI für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Ci-Cö-Alkyl, CI-CÖ- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy und Ci-C6-Halogenalkoxy steht, X 1 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy,
X2 für Sauerstoff, Schwefel, NR5 oder NOH steht, V-Z für R24CH-CHR25 oder R24C=CR25 steht, n für 1 oder 2 steht, X 2 is oxygen, sulfur, NR 5 or NOH, VZ is R 24 CH-CHR 25 or R 24 is C = CR 25 , n is 1 or 2,
R für NR18R19 oder für jeweils gegebenfalls durch Halogen, Sauerstoff (führt zu C=0) oder Cyano substituiertes Ci-Ce-Alkyl, C3-C6-Alkenyl, Cs-Ce-Alkinyl, Ci-C6-Alkoxy-Ci-C4-alkyl, Ci-C6- Alkyl-S-Ci-C4-alkyl, Ci-C6-Alkyl-S(0)-Ci-C4-alkyl, Ci-C6-Alkyl-S(0)2-Ci-C4-alkyl, für R18-CO- Ci-C4-alkyl, für NR18R19-CO-Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durchR for NR 18 R 19 or for any given by halogen, oxygen (leads to C = 0) or cyano substituted Ci-Ce-alkyl, C 3 -C 6 alkenyl, Cs-Ce-alkynyl, Ci-C 6 alkoxy -C-C 4 alkyl, Ci-C 6 - alkyl-S-Ci-C4-alkyl, Ci-C 6 alkyl-S (0) -C C-4 alkyl, Ci-C 6 alkyl S (0) 2- Ci-C 4 -alkyl, for R 18 -CO-Ci-C 4 -alkyl, for NR 18 R 19 -CO-Ci-C 4 -alkyl, optionally optionally once or twice by
Sauerstoff (führt zu C=0), Ci-C4-Alkyl, C3-C8-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C8-Cycloalkenyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, Cs-Ce-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C6-Oxygen (resulting in C = 0) Ci-C 4 alkyl, C 3 -C 8 cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted C3-C6-cycloalkyl, mono- or di-optionally substituted by oxygen (resulting in C = 0) Ci-C4 alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted C3-C8-cycloalkenyl, optionally monosubstituted or disubstituted (with oxygen leads to C = 0) Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted C3-C6
Cycloalkyl-Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, Cs-Ce-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3- C6-Cycloalkenyl-Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, Cs-Ce-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), C1-C4- Cycloalkyl-Ci-C4-alkyl, optionally substituted once or twice by oxygen (leading to C = 0) Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl substituted C 3 -C 6 -cycloalkenyl-C 1 -C 4 -alkyl, which may be monosubstituted or disubstituted by oxygen (gives C = 0), C 1 -C 4 -alkyl, C 1 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -cycloalkyl-C 1 -C 4 -alkyl C 4 haloalkyl-substituted heterocyclyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 -C 4
Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes Heterocyclyl-Ci- C4-alkyl oder für jeweils gegebenenfalls einfach bis dreifach durch Halogen, Cyano, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy substituiertes Phenyl, Phenyl-Ci-C4-alkyl, Hetaryl und Hetaryl-Ci-C4-alkyl steht, R3 für Wasserstoff oder Ci-Ce-Alkyl steht, Alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl substituted heterocyclyl-Ci- C4-alkyl or represents in each case optionally mono- to trisubstituted by halogen, cyano, Ci-C 4 alkyl, C -C 4 haloalkyl, C3-C6-cycloalkyl, Ci-C 4 alkoxy or Ci-C is 4 -haloalkoxy-substituted phenyl, phenyl-Ci-C4-alkyl, hetaryl and hetaryl-Ci-C4-alkyl, R 3 is hydrogen or C 1 -C 6 -alkyl,
R4 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Aryl, Aryl- Ci-C4-alkyl und Hetaryl-Ci-C4-alkyl steht, R5 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen- Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Aryl, Aryl- Ci-C4-alkyl und Hetaryl-Ci-C4-alkyl steht, oder R 4 is a radical selected from hydrogen, Ci-C 4 alkyl, halo-Ci-C4-alkyl, cyano-Ci-C 4 alkyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl , C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl , C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, R 5 is a radical from the series consisting of hydrogen, C 1 -C 4 Alkyl, halo-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 - alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C4-alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, or
R3 und R4 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann, R 3 and R 4, together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (where oxygen and sulfur atoms are not immediately adjacent may contain)
R6 für Wasserstoff oder Ci-C4-Alkyl steht, R 6 is hydrogen or C 1 -C 4 -alkyl,
R7 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C4-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy, Halogen-Ci-C4- alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Aryl, Aryl-Ci-C4-alkyl oder Hetaryl-Ci-C4-alkyl steht, oder R 7 is a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 4 cycloalkyl-Ci-C4-alkyl, Ci-C 4 alkoxy, halogen-Ci-C 4 - alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxycarbonyl, Ci-C4 alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C 4 alkyl, aryl, aryl-Ci-C4-alkyl or hetaryl-Ci-C4 -alkyl, or
R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann, R 6 and R 7, together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (with oxygen and sulfur atoms not being immediately adjacent may contain)
R8 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, Cyano-Ci-C6-alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C2-C6-Alkenyl, Ci-C6-Alkoxy-Ci-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes Ci-Cö-Alkylcarbonyl und Ci-Cö-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxycarbonyl und gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkyl und Cyano substituiertes C3-C6- Cycloalkylcarbonyl steht, oder für ein Kation oder für ein gegebenenfalls durch Ci-Cö-Alkyl oder Aryl-Ci-Cö-alkyl substituiertes Ammonium-Ion steht, R 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by halogen, Ci-Cö-alkyl, Ci-C6 Alkoxy, C 1 -C 6 -haloalkyl and cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or represents a cation or an ammonium ion which is optionally substituted by C 1 -C 6 -alkyl or aryl-C 1 -C 6 -alkyl,
R9 für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C6-Alkoxy, C1-C6- Halogenalkoxy, Ci-C6-Alkylthio, Ci-C6-Halogenalkylthio, Ci-C6-Alkylsulfinyl, C1-C6- Halogenalkylsulfinyl, Ci-Cö-Alkylsulfonyl und Ci-C6-Halogenalkylsulfonyl substituiertes C1-C6- Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci- Cö-Halogenalkyl, Ci-C6-Alkoxy oder Ci-C6-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-R 9 is a radical from the series in each case optionally substituted by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 4 -alkyl -Cö-alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyl -C6-alkoxy or Ci-C6-haloalkoxy-substituted C3-C6-cycloalkyl, C3-
C6-Cycloalkyl-Ci-C6-alkyl und C3-C6-Cycloalkenyl, in welchen ein Ringglied durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein kann (und dabei insbesondere für C6-cycloalkyl-Ci-C6-alkyl and C3-C6-cycloalkenyl, in which a ring member by a heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
wobei der Pfeil jeweils die Bindung zum S-Atom im Rest (C-l) und im Rest (F-l) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C6-Alkyl, CI-CÖ- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-C6-Alkylthio, CI-CÖ- Halogenalkylthio, Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci-C6-Alkylsulfonyl, CI-CÖ- Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, CI-CÖ- Alkylcarbonylamino, Ci-C6-Alkoxycarbonylamino, Ci-Ce-Alkoxy-Ci-Ce-alkyl, Ci-Ce- Halogenalkoxy-Ci-Ce-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Ci-C6- Alkylcarbonyl, Ci-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl- Ci-Ce-alkyl, Heteroaryl-Ci-C6-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, Ci-C6-Halogenalkyl, C3-C6- Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Alkylcarbonyl und Ci-C6-Alkoxylcarbonyl stehen, oder wherein the arrow in each case marks the bond to the S atom in the radical (Cl) and in the radical (Fl)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, CI- C 1 - haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, -Ce- haloalkoxy-Ci-Ce-alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, Ci-C 6 - alkylcarbonyl, Ci-C6- Alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-Ci-Ce-alkyl, heteroaryl-Ci-C6-alkyl or NR'R ", wherein R 'and R" are independently a radical from the series hydrogen, Ci-Cö Alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl, or
R8 und R9 können im Rest (C-l) und im Rest (F-l) auch zusammen mit der N-S(0)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, CI-CÖ- Alkyl, Ci-C6-Halogenalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine und bevorzugt eine Carbonylgruppe enthalten kann, insbesondere können R8 und R9 zusammen mit der N-S(0)n-Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe R 8 and R 9 in the radical (Cl) and in the radical (Fl) can also be used together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 -alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably a carbonyl group may contain, in particular R 8 and R 9 together with the NS (0) n group to which they are attached, a radical from the series
stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert), für einen Rest aus der Reihe jeweils gegebenenfalls durch Methyl, Cyano, Carbamoyl substituiertes Ci-Cö-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Methyl, Trifluormethyl, Halogen, Cyano oder Carbamoyl substituiertes C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C2-alkyl und C3-C6-Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls durch Ci-C i-Alkyl, C1-C4- Halogenalkyl, Ci-C i-Alkoxy, Ci-C i-Halogenalkoxy, Ci-C i-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)- amino, Halogen, Nitro oder Cyano substituiertes Aryl, Heteroaryl, Aryl-Ci-C i-alkyl und Heteroaryl-Ci-C2-alkyl und eine gegebenenfalls durch Ci-C i-Alkyl, Ci-C i-Alkylcarbonyl, C1-C4- Alkyl-Ci-C4-alkoxycarbonyl oder Ci-C4-Alkylsulfonyl substituierte Aminogruppe steht, (in which the arrow in each case marks the bond to the C (X) group), a radical from the series in each case optionally substituted by methyl, cyano, carbamoyl-substituted Ci-Cö-alkyl, C2-C6-alkenyl and C2-C6-alkynyl each optionally substituted by methyl, trifluoromethyl, halogen, cyano or carbamoyl substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C 2 -alkyl and C3-C6-cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur , Oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each optionally substituted by Ci-C i-alkyl, C1-C4-haloalkyl, Ci-C i-alkoxy, Ci-C i -haloalkoxy, Ci-C i alkylthio, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, Ci-C 4 alkylamino, di- (Ci-C 4 alkyl) - amino, halogen, nitro or cyano-substituted aryl, heteroaryl, aryl-Ci-C i-alkyl and heteroaryl-C 1 -C 2 -alkyl and an optionally by Ci-C i-alkyl, Ci-C i-alkylcarbonyl, C 1 -C 4 Alkyl-C 1 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkylsulfonyl-substituted amino group,
R8 und R15 im Rest (C-6) auch zusammen mit der N-S(0)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls durch Methyl, Cyano, Carbamoyl oder Carboxyl substituiertes Ci-C6-Alkyl, Ci-C6-Alkoxy, C2-C4-Alkenyl und C2-C4- Alkinyl, jeweils gegebenenfalls durch Halogen, Cyano, Nitro, Ci-C6-Alkyl, Ci-C6-Halogenalkyl, C3-C6-Cycloalkyl, Ci-Ce-Alkoxy, Ci-Ce-Halogenalkoxy, Ci-Ce-Alkylthio, Ci-Ce- Halogenalkylthio, Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci-C6-Alkylsulfonyl, CI-CÖ- Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, CI-CÖ- Alkylcarbonylamino, Ci-C6-Alkoxycarbonylamino, C2-C6-Alkenyl, C2-C6-Alkinyl oder CI-CÖ- Alkylcarbonyl substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl und C3-C6- Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls durch Halogen, Cyano, Nitro, Ci-Ce-Alkyl, Ci-Ce- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-Ce-Alkylthio, Ci-Ce- Halogenalkylthio, Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci-C6-Alkylsulfonyl, CI-CÖ- Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, CI-CÖ- Alkylcarbonylamino, Ci-C6-Alkoxycarbonylamino, C2-C6-Alkenyl, C2-C6-Alkinyl oder CI-CÖ- Alkylcarbonyl substituiertes Aryl, Heteroaryl, Aryl-Ci-C2-alkyl und Heteroaryl-Ci-C2-alkyl und eine gegebenenfalls durch Ci-Cö-Alkyl, Ci-C6-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-Ce-Halogenalkoxy, Ci-Ce-Alkylthio, Ci-Ce-Halogenalkylthio, Ci-Ce-Alkylsulfinyl, Ci-Ce- Halogenalkylsulfinyl, Ci-C6-Alkylsulfonyl, Ci-C6-Halogenalkylsulfonyl, C2-C6-Alkenyl, C2-C6- Alkinyl oder Ci-C6-Alkylcarbonyl substituierte Aminogruppe steht, für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C6-Alkoxy, CI-CÖ- Halogenalkoxy, Ci-Cö-Alkylthio, Ci-C6-Halogenalkylthio, Ci-C6-Alkylsulfinyl, CI-CÖ- Halogenalkylsulfinyl, Ci-C6-Alkylsulfonyl oder Ci-C6-Halogenalkylsulfonyl substituiertes CI-CÖ- Alkyl, Ci-C6-Alkoxy, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci-C6-Halogenalkyl, Ci-C6-Alkoxy oder Ci-C6-Halogenalkoxy substituiertes C3-C6- Cycloalkyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Cs-Ce-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N- Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-l -oxid, N-Thiomorpholinyl-l , l -dioxid, N- Piperazinyl, N-l -Methylpiperazinyl und N-2-Oxo-l -methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C6-Alkyl, Ci-C6-Halogenalkyl, C3-C6- Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-C6-Alkylthio, Ci-C6-Halogenalkylthio, Ci- C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci-C6-Alkylsulfonyl, Ci-C6-Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, Ci-C6-Alkylcarbonylamino, CI-CÖ- Alkoxycarbonylamino, Ci-C6-Alkoxy-Ci-C6-alkyl, Ci-C6-Halogenalkoxy-Ci-C6-alkyl, C2-C6- Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Ci-C6-Alkylcarbonyl, Ci-C6- Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-Ci-C6-alkyl, Heteroaryl-Ci-C6-alkyl und NR'R" steht, worin R' und R" unabhängig voneinander jeweils für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, Ci-C6-Haloalkyl, C3-C6-Cycloalkyl, CI-CÖ- Alkoxy, Ci-Cö-Alkylcarbonyl und Ci-C6-Alkoxylcarbonyl stehen, und R17 können im Rest (C-8) und im Rest (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, CI-CÖ- Alkyl, Ci-Cö-Halogenalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder eine Carbonylgruppe enthalten kann, insbesondere können R8 und R17 zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe R 8 and R 15 in the radical (C-6) together with the NS (0) n group to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or two further heteroatoms from the series sulfur, oxygen (oxygen and sulfur atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group, a radical from the series hydrogen, in each case optionally by methyl, cyano, carbamoyl or carboxyl substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, each optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkyl cycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, CI-C Ö - haloalkylsulfonyl , Amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamine O, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkylcarbonyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkenyl in which the rings are at least a heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each optionally substituted by halogen, cyano, nitro, Ci-Ce-alkyl, Ci-Ce- haloalkyl, C3-C6-cycloalkyl, Ci C6-alkoxy, Ci-C6-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, CI-C Ö - haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkylcarbonyl-substituted aryl, Heteroaryl, aryl-Ci-C 2 -alkyl and heteroaryl-Ci-C 2 -alkyl and an optionally by Ci-Cö-alkyl, Ci-C6-haloalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-Ce Haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-Halogens n-alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkylcarbonyl-substituted amino groups, for a radical from the series in each case optionally substituted by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkoxy alkylsulfonyl or Ci-C6-haloalkylsulfonyl-substituted CI-C Ö - alkyl, Ci-C6-alkoxy, C2-C6-alkenyl and C2-C6 alkynyl, each optionally substituted by halogen, Ci-COE-alkyl, Ci-C6-haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 1 -C 12 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N- Thiomorpholinyl, N-thiomorpholinyl-l-oxide, N-thiomorpholinyl-l, l-dioxide, N- Piperazinyl, N-methylpiperazinyl and N-2-oxo-1-methylpiperazinyl, each optionally substituted by halogen, cyano (also in the alkyl portion), nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, ci C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, ci C 6 -alkylamino, di (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -cycloalkyl alkyl, C 2 -C6- alkenyl, C 2 -C 6 alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, Ci-C6 alkylcarbonyl, Ci-C 6 - alkoxycarbonyl or aminocarbonyl substituted aryl, heteroaryl, aryl C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl and NR'R ", where R 'and R" are each independently a radical from the series consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl, and R 17 may be substituted in the radical (C-8) and in the radical (F-8) also together with the NC (X) group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, Ci-C6-haloalkoxy-substituted 5- to 7-membered ring form, which may contain one or two further heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or a carbonyl group, in particular R 8 and R 17, together with the NC (X) group to which they are attached, are out of line for a remainder
stehen (worin der Pfeil jeweils die Bindung zum S-Atom im Rest (C-8) und im Rest (F-8) markiert), für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituiertes CI-CÖ- Alkyl, Ci-C6-Alkoxy, Ci-C6-Alkoxy-Ci-C4-alkyl, Ci-C6-Alkyl-S-Ci-C4-alkyl, Ci-C6-Alkyl-S(0)-Ci-C4-alkyl, Ci-C6- Alkyl-S(0)2-Ci-C4-alkyl, Ci-C6-Alkylcarbonyl, Ci-C6-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6- Cycloalkenyl, C3-C6-Cycloalkyl-Ci-C3-alkyl, C3-C6-Cycloalkenyl-Ci-C3-alkyl, Heterocyclyl, Heterocyclyl-Ci-C3-alkyl und jeweils gegebenenfalls einfach bis vierfach durch Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, C3-C6-Cycloalkyl, Halogen oder Cyano substituiertes Phenyl, Phenyl-Ci-C3-alkyl, Hetaryl und Hetaryl-Ci-C3-alkyl steht, für Wasserstoff, ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch Ci-C i-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkyl-S-Ci-C4-alkyl, C1-C4- Alkyl-S(0)-Ci-C4-alkyl und Ci-C4-Alkyl-S(0)2-Ci-C4-alkyl steht, für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, C3- Ce-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy und NR20R21 steht, für einen Rest aus der Reihe O, S, SO und SO2 steht, für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C2-C6-Halogenalkyl, Cyano-Ci-C6-alkyl, C2-C4-Alkenyl, C2-C4-Halogenalkenyl, C2-C4-Alkinyl, C2-C4-Halogenalkinyl, Ci-Ce-Alkoxy, Ci- C6-Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxy-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Bis(Ci-C6-alkoxy)-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkylsulfanyl-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkylcarbonyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci- C6-Alkylsulfinyl-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkylsulfonyl- Ci-C6-alkyl, Di-(Ci-C6-alkyl)-aminosulfanyl-Ci-C6-alkyl, Di-(Ci-C6-alkyl)-aminosulfinyl-Ci-C6- alkyl, Di-(Ci-C6-alkyl)-aminosulfonyl-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxycarbonyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxycarbonyl-Ci- Cö-alkyl, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxy, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxycarbonyl, Di-(Ci-C6-alkyl)-aminocarbonyl, N-CI-CÖ- Alkyl-N-C3-C6-cycloalkylaminocarbonyl, Di-(Ci-C6-alkyl)-aminocarbonyl-Ci-C6-alkyl, N-CI-CÖ- Alkyl-N-C3-C6-cycloalkylaminocarbonyl-Ci-C6-alkyl, Heterocyclylcarbonyl-Ci-C6-alkyl, CI-CÖ- Alkylsulfanyl, Ci-C6-Halogenalkylsulfanyl, Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci- Cö-Alkylsulfonyl, Ci-C6-Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Ci- Ce-Alkyl, Ci-Ce-Halogenalkyl, Cs-Ce-Cycloalkyl, Ci-Ce-Alkoxy, Ci-Ce-Halogenalkoxy, Ci-Ce- Alkoxycarbonyl, Ci-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Ci-C6-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-C6-Alkoxycarbonyl, Ci-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Ci-Cö-Alkyl oder Halogen substituiert ist) substituiertes C3- C6-Cycloalkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Ci-Cö-Alkyl, CI-CÖ- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-C6-Alkoxycarbonyl, Ci-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Ci-Cö-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl-Ci-C6-alkyl, gegebenenfalls durch Halogen, Cyano (auch im Ci-C6-Alkylteil von Heterocyclyl-Ci-C6-alkyl), Nitro, Hydroxy, CI-CÖ- Alkyl, Ci-C6-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci- Ce-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, CI-CÖ- Alkylthio, Ci-Ce-Halogenalkylthio, Ci-Ce-Alkylsulfmyl, Ci-Ce-Alkylsulfonyl, Ci-Ce- Halogenalkylsulfinyl, Ci-C6-Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)- amino, Ci-C6-Alkylcarbonylamino, Ci-C6-Alkoxycarbonylamino, Ci-C6-Alkoxy-Ci-C6-alkyl, Ci- Ce-Halogenalkoxy-Ci-Ce-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Ci- Cö-Alkylcarbonyl, Ci-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclyl-Ci-C6- alkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Ci-C6-Alkyl, CI-CÖ- Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-Cö-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C6-Alkoxy oder Ci-C6-Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im Ci-C6-Alkylteil von Aryl-Ci-Cö-alkyl), Nitro, Hydroxy, Amino, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-Cö-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C6-Alkoxy oder Ci- C6-Halogenalkoxy substituiertes Aryl-Ci-Cö-alkyl, gegebenenfalls durch Halogen, Cyano (auch im Ci-Ce-Alkylteil von Hetaryl-Ci-Ce-alkyl), Nitro, Hydroxy, Ci-Ce-Alkyl, Ci-Ce-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-Cö-Alkyl und C3-C6- Cycloalkyl substituiert ist), Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-Cö-Alkylthio, CI-CÖ- Halogenalkylthio, Ci-C6-Alkylsulfinyl, Ci-Cö-Alkylsulfonyl, Ci-C6-Halogenalkylsulfinyl, CI-CÖ- Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, CI-CÖ- Alkylcarbonylamino, Ci-C6-Alkoxycarbonylamino, Ci-C6-Alkoxy-Ci-C6-alkyl, CI-CÖ- Halogenalkoxy-Ci-Ce-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Ci-C6- Alkylcarbonyl, Ci-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetaryl-Ci-C6-alkyl, oder für einen D-Rest aus der Reihe (D- 1 ) bis (D-3) (in which the arrow in each case marks the bond to the S atom in the radical (C-8) and in the radical (F-8)), a radical from the series hydrogen, hydroxy, in each case optionally monosubstituted or polysubstituted by halogen or by a simple or disubstituted by cyano CI-C Ö - alkyl, Ci-C6-alkoxy, Ci-C 6 alkoxy-Ci-C4-alkyl, Ci-C 6 alkyl-S-Ci-C4-alkyl, Ci-C 6 alkyl-S (0) -C C-4 alkyl, Ci-C 6 - alkyl-S (0) 2 -C-C 4 alkyl, Ci-C6 alkylcarbonyl, Ci-C 6 alkoxycarbonyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - cycloalkenyl, C3-C6-cycloalkyl-Ci-C3-alkyl, C3-C6-cycloalkenyl-Ci-C3-alkyl, heterocyclyl, heterocyclyl-Ci-C3-alkyl and in each case optionally mono- to tetrasubstituted by Ci-C 4 alkyl, Ci- C4 haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6 cycloalkyl, halogen or cyano-substituted phenyl, phenyl-Ci C 3 -alkyl, hetaryl and hetaryl-C 1 -C 3 -alkyl, for hydrogen, an alkali or alkaline earth metal ion or for an optionally monosubstituted to fourfold by Ci-C i-alkyl-substituted ammonium ion or for each optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted radical from the series Ci-C 4 - Alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-S-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-S (0) - C 1 -C 4 -alkyl and C 1 -C 4 -alkyl-S (0) 2 -C 1 -C 4 -alkyl, a radical from the series consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 4 -alkyl, haloalkyl, C3-Ce-cycloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, and NR 20 R 21, represents a radical from the series O, S, SO and SO2, represents a radical from the group of hydrogen , Ci-COE-alkyl, C 2 -C 6 haloalkyl, cyano-Ci-C6-alkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 -haloalkynyl, Ci-Ce-alkoxy, Ci-C6-haloalkoxy, optionally substituted by halogen Ci-C6-alkoxy-Ci-C6-alkyl, if necessary Is substituted by halogen bis (Ci-C6-alkoxy) -Ci-C6-alkyl, optionally substituted by halogen Ci-C6-alkylsulfanyl-Ci-C6-alkyl, optionally substituted by halogen Ci-C 4 alkylcarbonyl-Ci-C 4 C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, and di- (C 1 -C 6 -alkyl) -aminosulfanyl-C 1 -C 6 -alkyl optionally substituted by halogen -alkyl, di- (Ci-C6-alkyl) -aminosulfinyl-Ci-C6-alkyl, di (Ci-C6-alkyl) -aminosulfonyl-Ci-C6-alkyl, optionally substituted by halogen Ci-C6-Alkoxycarbonyl, if necessary halogen-substituted Ci-C6-alkoxycarbonyl-Ci Coe-alkyl, optionally halogen-substituted C2-C4 alkynyloxy, optionally substituted by halogen C 2 -C 4 -alkynyloxycarbonyl, di- (Ci-C6-alkyl) aminocarbonyl, N CI-COE alkyl-N-C3-C6-cycloalkylaminocarbonyl, di- (Ci-C6-alkyl) aminocarbonyl-Ci-C6-alkyl, N-CI-C Ö - alkyl-N-C3-C6-cycloalkylaminocarbonyl C 1 -C 6 -alkyl, heterocyclylcarbonyl -C-C6-alkyl, CI-C Ö - alkylsulfanyl, Ci-C6-Halogenalkylsulfanyl, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci Coe-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, optionally substituted by halogen, cyano, Nitro, ce-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl or hetaryl (which optionally itself by Ci-C6-alkyl or halogen is substituted) substituted C3-C6-cycloalkyl, optionally substituted by halogen, cyano, nitro, Ci-Cö-alkyl, Ci-Cö-haloalkyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, Ci -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl or hetaryl (which is unsubstituted or itself substituted by C 1 -C 6 -alkyl or halogen), C 3 -C 6 -cycloalkylcarbonyl optionally substituted by halogen, cyano, nitro, ci Cö-alkyl, CI-CÖ-haloalkyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl or hetaryl (which ge optionally itself substituted by Ci-Cö-alkyl or halogen) substituted C3-C6-cycloalkyl-Ci-C6-alkyl, optionally substituted by halogen, cyano (also in the Ci-C6-alkyl portion of heterocyclyl-Ci-C6-alkyl), nitro , Hydroxy, CI-C Alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is unsubstituted or substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, Cl- C 6 alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfmyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl ) - amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, ciCe-haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 C 6 -alkynyl, C 1 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl-substituted heterocyclyl-C 1 -C 6 -alkyl, where appropriate by halogen, cyano, nitro, hydroxyl, Amino, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is unsubstituted or substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 6 -alkoxy or C6-haloalkoxy-substituted aryl, optionally substituted by halogen, cyano (also in the Ci-C6-alkyl portion of aryl-Ci-C alkyl), nitro, hydroxy, amino, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl), Ci-C6-alkoxy or Ci-C6-haloalkoxy-substituted aryl-Ci-Cö-alkyl, optionally substituted by halogen, cyano (also in the Ci-Ce-alkyl portion of hetaryl-Ci-Ce-alkyl), nitro, hydroxy, Ci-Ce -Alkyl, Ci-Ce-haloalkyl, C3-C6-cycloalkyl (which is optionally substituted by halogen, cyano, Ci-Cö-alkyl and C3-C6-cycloalkyl), Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci -Cö-alkylthio, CI-CÖ-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-Cö-alkylsulfonyl, Ci-C6-haloalkylsulfinyl, CI-C Ö - haloalkylsulfonyl, amino, Ci-C6-alkylamino, di (Ci-C6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 8 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, Ci-C 6 - alkylcarbonyl, Ci-C6-alkoxycarbonyl or aminocarbonyl substitutability hetaryl-C 1 -C 6 -alkyl, or for a D radical from the series (D-1) to (D-3)
(D-1 ) (D-2) (D-3) einen der E-Reste aus der Reihe (E-l) bis (E-l 1) (D-1) (D-2) (D-3) one of the E radicals from the series (El) to (El 1)
E-26 -45 - E-26 -45 -
E-37 E-38 E-39 E-40  E-37 E-38 E-39 E-40
E-44 E-45 E-46 E-47  E-44 E-45 E-46 E-47
E-48 E-49 E-50 E-51 steht, oder im Fall, dass R für einen der unter d) genannten Reste steht  E-48 E-49 E-50 E-51, or in case R stands for one of the radicals mentioned under d)
auch für einen E-Rest aus der Reihe E-12 bis E-17  also for an E-rest from the series E-12 to E-17
steht, R für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy, Ci-C6-Alkyl, Ci-Ce-Halogenalkyl, Cyano-Ci-Ce-alkyl, C2-Ce-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C i-Alkyl und C3-C6-Cycloalkyl substituiert ist), C3-C6-Cycloalkyl-Ci-C6-alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C3-C6-Alkenyloxy, C3- Cö-Alkinyloxy, C3-C6-Cycloalkyloxy, Ci-Cö-Alkylcarbonyloxy, C2-C6-Alkenylcarbonyloxy, C2- Cö-Alkinylcarbonyloxy, C3-C6-Cycloalkylcarbonyloxy, Ci-C6-Alkoxycarbonyloxy, CI-CÖ- Alkylsulfonyloxy, Ci-C6-Alkylamino, C3-C6-Alkenylamino, C3-C6-Alkinylamino, C3-C6- Cycloalkylamino, Ci-C6-Alkylthio, Ci-C6-Halogenalkylthio, C3-C6-Alkenylthio, C3-C6- Alkinylthio, C3-C6-Cycloalkylthio, Ci-Ce-Alkylsulfinyl, Ci-Ce-Alkylsulfonyl, Ci-C6- Alkylcarbonyl, Ci-C6-Alkoxyimino-Ci-C6-alkyl, Ci-C6-Alkoxycarbonyl, Aminocarbonyl, CI-CÖ- Alkylaminocarbonyl, Di-(Ci-C6-alkyl)-aminocarbonyl, Aminothiocarbonyl, CI-CÖ- Alkylaminosulfonyl, Ci-C6-Alkylsulfonylamino, Ci-C6-Alkylcarbonylamino, CI-CÖ- Alkylthiocarbonylamino, jeweils gegebenenfalls durch einen Rest aus der Reihe Halogen, Cyano, Nitro, Amino, Hydroxy, Ci-Cö-Alkyl oder Ci-C6-Halogenalkyl substituiertes Phenyl, Phenoxy, Pyridinyl und Pyridinyloxy steht, stands, R is a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C -alkenyl, C 2 -C 6 Alkynyl, Cs-Ce-cycloalkyl (which is optionally substituted by halogen, cyano, Ci-C i-alkyl and C3-C6-cycloalkyl), C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 -alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, ci C 6 -alkoxycarbonyloxy, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 -alkynylamino, C 3 -C 6 -cycloalkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -alkoxy alkenylthio, C3-C6 alkynylthio, C 3 -C 6 cycloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-C 6 - alkylcarbonyl, Ci-C6-alkoxyimino-Ci-C6-alkyl, Ci-C6 alkoxycarbonyl, aminocarbonyl, CI-C Ö - alkylaminocarbonyl, di- (Ci-C6-alkyl) aminocarbonyl, aminothiocarbonyl, Cl-C Ö - alkylaminosulfonyl , C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkylthiocarbonylamino, in each case optionally substituted by a radical from the series halogen, cyano, nitro, amino, hydroxy, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl-substituted phenyl , Phenoxy, pyridinyl and pyridinyloxy,
R21 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C3-C6-Cycloalkyl, Ci-C6-Halogenalkyl, C3-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Cyano-Ci-Ce-alkyl, Ci-C6- Alkylcarbonyl, C2-C6-Alkenylcarbonyl, Ci-C6-Halogenalkylcarbonyl, C2-C6-R 21 is a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl Ci-Ce-alkyl, cyano-Ci-Ce-alkyl, Ci-C 6 - alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, Ci-C6-haloalkylcarbonyl, C 2 -C6-
Halogenalkenylcarbonyl, Ci-Ce-Alkoxy-Ci-Ce-alkyl, Ci-C6-Alkoxycarbonyl, Ci-C6-Alkylsulfonyl und Ci-C6-Halogenalkylsulfonyl steht, Haloalkenylcarbonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl,
R23 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6- Cycloalkyl, C3-C6-Cycloalkenyl, Ci-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6- Alkinyloxy, C3-C6- Cycloalkyloxy, Ci-C4-Alkylthio-Ci-C4-alkyl, C2-C4-Alkenylthio- Ci- C4-alkyl, Cyano-Ci-C4- alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl steht, oder, im Fall, dass R2 für einen der unter c) oder f) genannten Reste steht R 23 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkoxy alkenyloxy, C2-C6 alkynyloxy, C3-C6-cycloalkyloxy, Ci-C4-alkylthio-Ci-C4-alkyl, C2-C4-alkenylthio Ci- C4-alkyl, cyano-Ci-C4- alkyl, Ci-C4- Alkoxy-Ci-C 4 -alkyl, or, in the case that R 2 is one of the radicals mentioned under c) or f)
R22 und R23 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gesättigten Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, und R 22 and R 23 together with the nitrogen atom to which they are attached form a saturated ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms, and
R24 für Wasserstoff oder einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Phenyl und Phenyl-Ci-C2-alkyl steht, R für Wasserstoff oder einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Phenyl und Phenyl-Ci-C2-alkyl steht, R 24 is hydrogen or a radical optionally substituted by halogen or cyano radical from the series Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-Ci-C 2 alkyl stands, R is hydrogen or a radical optionally substituted by halogen or cyano radical from the series Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-Ci-C 2 alkyl .
R27 für Wasserstoff oder Ci-C i-Alkyl steht und R 27 is hydrogen or C i-alkyl, and
R26 für einen Rest aus der Reihe Wasserstoff, Ci-C/i-Alkyl, Ci-C i-Halogenalkyl, C2-C4-Alkenyl, C2- C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C2-alkyl, Ci-C6- Alkylsulfanyl, Ci-C6-Halogenalkylsulfanyl Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci- Ce-Alkylsulfonyl, Ci-C4-Alkylthio-Ci-C2-alkyl, Ci-C4-Alkylsulfmyl-Ci-C2-alkyl, C1-C4- Alkylsulfonyl-Ci-C2-alkyl und Cyano-Ci-C4-alkyl steht, und R 26 is a radical from the group of hydrogen, Ci-C / i-alkyl, Ci-C i-haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, C 3 -C 6 cycloalkyl, C3- C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 2 alkyl, Ci-C 6 - alkylsulfanyl, Ci-C6-Halogenalkylsulfanyl Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci- Ce-alkylsulfonyl, Ci-C4-alkylthio-Ci-C 2 alkyl, Ci-C 4 -Alkylsulfmyl-Ci-C 2 alkyl, C 1 -C4- alkylsulphonyl-Ci-C 2 alkyl, and cyano Ci-C 4 alkyl, and
Verbindungen der Formel (I), in welchen Compounds of the formula (I) in which
A für den folgenden A-Rest A for the following A remainder
(A-a) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, und  (A-a), wherein the dotted line represents the bond to the carbon atom of the bicyclic of the formula (I), and
G1 für N oder C-B1 steht, G 1 is N or CB 1 ,
B1 für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C6-Alkyl und Ci-C4-Halogenalkyl steht, B 1 is a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
B2 für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C6-Alkyl und Ci-C4-Halogenalkyl steht, B 2 is a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
T für Sauerstoff oder ein Elektronenpaar steht, T is oxygen or a pair of electrons,
Q für Schwefel steht, Q stands for sulfur,
R1 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl und Ci-C6-Alkoxy steht, R 1 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy,
R2 a) für einen der folgenden B-Reste -49- R 2 a) for one of the following B radicals -49-
(B-38) (B-39) (B-40) (B-38) (B-39) (B-40)
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin für Wasserstoff oder für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, C1-C4- Alkylamino, Halogen-Ci-C4-alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkyl, Halogen-Ci-C4- alkyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, halogeniertes Ci-C4-Alkoxy-Ci-C4-alkyl, Bis(Ci-C4-alkoxy)-Ci-C4-alkyl, Bis(halogen-Ci-C4-alkoxy)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfinyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci- C4-alkylsulfonyl)-Ci-C4-alkyl, Bis(Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(halogen-Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Bis(hydroxy-Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, a//jAa-Hydroxyimino-Ci-C4-alkoxycarbonyl-Ci-C4-alkyl, fl^Afl-Ci-C4-Alkoxy-imino-Ci-C4-alkoxycarbonyl-Ci-C4-alkyl, C(X2)NR3R4, NR6R7, C1-C4- Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylthio, C1-C4- Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyl- dioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxy und Ci-C4-Alkoxy-Ci-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Ci-C4-Alkyl und Halogen-Ci-C t-alkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Ci-C i-Alkyl, Halogen-Ci-C i-alkyl, Ci-C i-Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkylthio, Ci-C -Alkylthio-Ci-C -alkyl und C3-C6-Cycloalkyl) und die Heteroaryl-Ci-C4-alkylreste Triazolyl-Ci-C4-alkyl, Pyridyl-Ci-C4- alkyl, Pyrimidyl-Ci-C4-alkyl und Oxadiazolyl-Ci-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und C1-C4- Alkyl) steht, oder aa) für einen der folgenden B-Reste (B-42) (B-43) (B-44) (B- 45), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I) wherein, in the case of hydrogen or a group selected from the group consisting of halogen , Nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno-C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 3 - C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C3-C6 cycloalkyl-Ci-C4-alkyl, Ci-C 4 alkoxy-alkoxy, halogen-Ci-C 4, C 4 alkoxy C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, bis (halogen-C 1 -C 4 -alkoxy) -C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfinyl) -Ci-C 4- alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfonyl) C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, bis (halogeno-C 1 -C 4 -alkylsulfanyl) -C 1 -C 4 -alkyl, bis (hydroxy-C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, a / / αA-Hydroxyimino-C 1 -C 4 -alkoxycarbonyl -Ci-C 4 -alkyl, fl ^ Afl-C 1 -C 4 -alkoxy-imino-C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 1 -C4- alkylthio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylthio, C1-C4 haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, the heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl , Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyl- dioxide, morpholinyl, Triazolinonyl, oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and Pyrazolinonyl (Which in turn may be substituted by C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl), phenyl (which itself is in turn may be substituted by halogen, cyano, nitro, Ci-C 4 alkyl and halo-C 1 -C 4 -alkyl), the heteroaryl radicals pyridyl, pyridyl-N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may be substituted by halogen, nitro, Ci-C i-alkyl, halo-Ci-C i-alkyl, Ci-C i-alkoxy, halo-Ci-C 4 -alkoxy, Ci-C 4 -alkoxy -C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl) and the heteroaryl-C 1 -C 4 -alkyl radicals triazolyl-C 1 -C 4 - alkyl, pyridyl-Ci-C 4 - alkyl, pyrimidyl-Ci-C 4 alkyl, and oxadiazolyl-Ci-C4-alkyl (which itself can in turn be substituted by halogen and C1-C4 alkyl), or aa) one of the following B residues
(B-31) (B-32)  (B-31) (B-32)
(B-33) (B-35) (B-36) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet und worin für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Ci-C i-Alkylamino, Halogen-Ci-C i- alkylamino, Di-(Ci-C4-alkyl)-amino, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C3-C6-Cycloalkyl- Ci-C4-alkyl, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, halogeniertes Ci-C4-Alkoxy-Ci- C4-alkyl, Bis(Ci-C4-alkoxy)-Ci-C4-alkyl, Bis(halogen-Ci-C4-alkoxy)-Ci-C4-alkyl, Ci-C4-Alkoxy- (Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfinyl)-Ci-C4-alkyl, C1-C4- Alkoxy-(Ci-C4-alkylsulfonyl)-Ci-C4-alkyl, Bis(Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(halogen-Ci- C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(hydroxy-Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, C1-C4-(B-33) (B-35) (B-36), wherein the broken line represents the bond to the carbon atom of the bicycle of the formula (I) and wherein a radical from the group halogen, nitro, amino, cyano, C 1 -C -alkylamino, halogeno-C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 3 -C 6 -cycloalkyl, C 3 -C 4 -alkyl, C 6 -cycloalkenyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (Ci-C4-alkoxy) -C-C4-alkyl, bis (halo-Ci-C4-alkoxy) -C-C4-alkyl, Ci-C4-alkoxy- (Ci-C4-alkylsulfanyl) -C-C 4 C 1 -C 4 alkoxy- (C 1 -C 4 -alkylsulfonyl) C 1 -C 4 -alkyl, bis (C 1 -C 4) -alkyl C4-alkylsulfanyl) -Ci-C4-alkyl, bis (halo-Cis-C4-alkylsulfanyl) -Ci-C4-alkyl, bis (hydroxy-Ci-C4-alkylsulfanyl) -Ci-C4-alkyl, C 1 -C 4 -
Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, a//jAa-Hydroxyimino-Ci-C4- alkoxycarbonyl-Ci-C4-alkyl, alpha-Ci-CA- Alkoxy- imino-Ci-C4-alkoxycarbonyl-Ci-C4-alkyl, C(X2)NR3R4, NR6R7, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, C1-C4- Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch C1-C4- Alkyl, Halogen-Ci-C4-alkyl, C1-C4- Alkoxy und Ci-C4-Alkoxy-Ci-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Ci-C4-Alkyl und Halogen-Ci-C4-alkyl), die Heteroarylreste Imidazolyl, Pyrazolyl, Oxazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkylthio, Ci-C4-Alkylthio-Ci-C4-alkyl und C3-C6-Cycloalkyl) und die Heteroaryl-Ci-C4-alkylreste Triazolyl-Ci-C4-alkyl, Pyridyl-Ci-C4- alkyl, Pyrimidyl-Ci-C4-alkyl und Oxadiazolyl-Ci-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und C1-C4- Alkyl) steht, Alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, α-αA-hydroxyimino-C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxycarbonyl-Ci -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkyl haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, the heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid , morpholinyl, Triazolinonyl, oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and Pyrazolinonyl (which may in turn be substituted itself by C 1 -C4- alkyl, halo-Ci-C4-alkyl, C 1 -C 4 - alkoxy and Ci-C4 Alkoxy-Ci-C4-alkyl), phenyl (which in turn may be substituted by halogen , Cyano, nitro, C 1 -C 4 -alkyl and halogeno-C 1 -C 4 -alkyl), the heteroaryl radicals imidazolyl, pyrazolyl, oxazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl ( which in turn may themselves be substituted by halogen, nitro, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl) and the heteroaryl-C 1 -C 4 -alkyl radicals triazolyl-C 1 -C 4 -alkyl , Pyridyl-C 1 -C 4 -alkyl, pyrimidyl-C 1 -C 4 -alkyl and oxadiazolyl-C 1 -C 4 -alkyl (which may in turn themselves be substituted by halogen and C 1 -C 4 -alkyl),
, wenn R2 für einen der unter a) oder aa) aufgeführten Reste steht, auch für einen C-Rest aus der Reihe if R 2 stands for one of the radicals listed under a) or aa), also a C-radical from the series
steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, oder wherein the dashed line represents the bond to the B radicals, or
R2 c) für einen Rest der Formel R 2 c) is a radical of the formula
X X
N N
1  1
R  R
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder  wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R2 d) für einen Rest der Formel R 2 d) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R2 e) für einen F-Rest aus der Reihe (F-8), (F- 10) und (F- 11 ) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R 2 e) for an F radical from the series (F-8), (F-10) and (F-11) wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R2 f) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, R 2 f) is a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
X für Sauerstoff oder Schwefel steht, X is oxygen or sulfur,
X2 für Sauerstoff, Schwefel oder NOH steht, V-Z für R24CH-CHR25 oder R24C=CR25 steht, n für 1 oder 2 steht, X 2 is oxygen, sulfur or NOH, VZ is R 24 CH-CHR 25 or R 24 is C = CR 25 , n is 1 or 2,
R3 für Wasserstoff oder Ci-Ce-Alkyl steht, R 3 is hydrogen or C 1 -C 6 -alkyl,
R4 für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl, Halogen-Ci-C i-alkyl, Cyano-Ci-C i-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Aryl, Aryl-R 4 is a radical from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl , C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl
Ci-C4-alkyl und Hetaryl-Ci-C4-alkyl steht, oder Ci-C 4 -alkyl and hetaryl-Ci-C 4 -alkyl, or
R3 und R4 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann, R6 für Wasserstoff oder Ci-C4-Alkyl steht, R 3 and R 4, together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (where oxygen and sulfur atoms are not immediately adjacent may contain) R 6 is hydrogen or C 1 -C 4 -alkyl,
R7 für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl, Halogen-Ci-C i-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C4-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy, Halogen-Ci-C4- alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C -Alkylthio-Ci-C -alkyl, Aryl, Aryl-Ci-C -alkyl oder Hetaryl-Ci-C -alkyl steht, oder R 7 is a radical from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 4 cycloalkyl-Ci-C4-alkyl, Ci-C 4 alkoxy, halogen-Ci-C 4 - alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 - alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C4-alkyl, Ci-C alkylthio-Ci-C alkyl, aryl, aryl-C alkyl or hetaryl-Ci-C -alkyl, or
R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann, R 6 and R 7, together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (with oxygen and sulfur atoms not being immediately adjacent may contain)
R8 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, Cyano-Ci-C6-alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C2-C6-Alkenyl, Ci-C6-Alkoxy-Ci-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes Ci-Cö-Alkylcarbonyl und Ci-Cö-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxycarbonyl und gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkyl und Cyano substituiertes C3-C6- Cycloalkylcarbonyl steht, oder für ein Kation oder für ein gegebenenfalls durch Ci-Cö-Alkyl oder Aryl-Ci-Cö-alkyl substituiertes Ammonium-Ion steht, R 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by halogen, Ci-Cö-alkyl, Ci-C6 Alkoxy, C 1 -C 6 -haloalkyl and cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or represents a cation or an ammonium ion which is optionally substituted by C 1 -C 6 -alkyl or aryl-C 1 -C 6 -alkyl,
R9 für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C6-Alkoxy, C1-C6- Halogenalkoxy, Ci-C6-Alkylthio, Ci-C6-Halogenalkylthio, Ci-C6-Alkylsulfinyl, C1-C6- Halogenalkylsulfinyl, Ci-Cö-Alkylsulfonyl und Ci-C6-Halogenalkylsulfonyl substituiertes C1-C6- Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci- Cö-Halogenalkyl, Ci-C6-Alkoxy oder Ci-C6-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-R 9 is a radical from the series in each case optionally substituted by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 4 -alkyl -Cö-alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyl -C6-alkoxy or Ci-C6-haloalkoxy-substituted C3-C6-cycloalkyl, C3-
C6-Cycloalkyl-Ci-C6-alkyl und C3-C6-Cycloalkenyl, in welchen ein Ringglied durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein kann (und dabei insbesondere für C6-cycloalkyl-Ci-C6-alkyl and C3-C6-cycloalkenyl, in which a ring member by a heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
wobei der Pfeil jeweils die Bindung zum S-Atom im Rest (C-l) und im Rest (F-l) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-Cö-Alkyl, CI-CÖ- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-Cö-Alkylthio, CI-CÖ- Halogenalkylthio, Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci-Cö-Alkylsulfonyl, CI-CÖ- Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, CI-CÖ- Alkylcarbonylamino, Ci-C6-Alkoxycarbonylamino, Ci-Ce-Alkoxy-Ci-Ce-alkyl, Ci-Ce- wherein the arrow in each case marks the bond to the S atom in the radical (Cl) and in the radical (F1)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, CI- C 1 - haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, -Ce-
Halogenalkoxy-Ci-Ce-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Ci-C6- Alkylcarbonyl, Ci-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl- Ci-C6-alkyl, Heteroaryl-Ci-C6-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, Ci-C6-Alkyl, Ci-C6-Halogenalkyl, C3-C6- Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Alkylcarbonyl und Ci-C6-Alkoxylcarbonyl stehen, Haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 12 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 - Alkylcarbonyl, Ci-C6-alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-Ci-C6-alkyl, heteroaryl-Ci-C6-alkyl or NR'R ", wherein R 'and R" independently of one another from the Hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl,
R15 für einen Rest aus der Reihe jeweils gegebenenfalls durch Methyl, Cyano, Carbamoyl, substituiertes Ci-C6-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Methyl, Trifluormethyl, Halogen, Cyano oder Carbamoyl, substituiertes C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C2-alkyl und C3-C6-Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls durch Ci-C i-Alkyl, C1-C4- Halogenalkyl, Ci-C i-Alkoxy, Ci-C i-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)- amino, Halogen, Nitro oder Cyano substituiertes Aryl, Heteroaryl, Aryl-Ci-C4-alkyl und Heteroaryl-Ci-C2-alkyl und eine gegebenenfalls durch Ci-C4-Alkyl, Ci-C4-Alkylcarbonyl, C1-C4- Alkyl-Ci-C4-alkoxycarbonyl oder Ci-C4-Alkylsulfonyl substituierte Aminogruppe steht, R 15 is a radical from the series each optionally substituted by methyl, cyano, carbamoyl, substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each optionally substituted by methyl, trifluoromethyl, halogen, cyano or carbamoyl C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl and C 3 -C 6 -cycloalkenyl in which the rings may contain at least one heteroatom selected from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen in each case optionally by C 1 -C -alkyl, C 1 -C 4 -haloalkyl, C 1 -C -alkoxy, C 1 -C -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkyl, -C4-haloalkylsulfonyl, Ci-C4-alkylamino, di (Ci-C4-alkyl) - amino, halogen, nitro or cyano substituted aryl, heteroaryl, aryl-Ci-C4-alkyl and heteroaryl-Ci-C2-alkyl and a optionally substituted by Ci-C4-alkyl, Ci-C4-alkylcarbonyl, C1-C4-alkyl-Ci-C4-alkoxycarbonyl or Ci-C4-alkylsulfonyl substituted amino group ste ht,
R8 und R15 im Rest (C-6) auch zusammen mit der N-S(0)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R 8 and R 15 in the radical (C-6) together with the NS (0) n group to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or two further heteroatoms from the series sulfur, oxygen (where oxygen and sulfur atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
R16 für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls durch Methyl, Cyano, Carbamoyl oder Carboxyl substituiertes Ci-Cö-Alkyl, Ci-C6-Alkoxy, C2-C4-Alkenyl und C2-C4- Alkinyl, jeweils gegebenenfalls durch Halogen, Cyano, Nitro, Ci-Cö-Alkyl, Ci-C6-Halogenalkyl, C3-C6-Cycloalkyl, Ci-Ce-Alkoxy, Ci-Ce-Halogenalkoxy, Ci-Ce-Alkylthio, Ci-Ce- Halogenalkylthio, Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci-C6-Alkylsulfonyl, CI-CÖ- Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, CI-CÖ- Alkylcarbonylamino, Ci-C6-Alkoxycarbonylamino, C2-C6-Alkenyl, C2-C6-Alkinyl oder CI-CÖ- Alkylcarbonyl substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl und C3-C6- Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls durch Halogen, Cyano, Nitro, Ci-Ce-Alkyl, Ci-Ce- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-Ce-Alkylthio, Ci-Ce- Halogenalkylthio, Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci-C6-Alkylsulfonyl, CI-CÖ- Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, CI-CÖ- Alkylcarbonylamino, Ci-C6-Alkoxycarbonylamino, C2-C6-Alkenyl, C2-C6-Alkinyl oder CI-CÖ- Alkylcarbonyl substituiertes Aryl, Heteroaryl, Aryl-Ci-C2-alkyl und Heteroaryl-Ci-C2-alkyl und eine gegebenenfalls durch Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-Ce-Halogenalkoxy, Ci-Ce-Alkylthio, Ci-Ce-Halogenalkylthio, Ci-Ce-Alkylsulfmyl, Ci-Ce- Halogenalkylsulfinyl, Ci-Cö-Alkylsulfonyl, Ci-C6-Halogenalkylsulfonyl, C2-C6-Alkenyl, C2-C6- Alkinyl oder Ci-Cö-Alkylcarbonyl substituierte Aminogruppe steht, für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C6-Alkoxy, CI-CÖ- Halogenalkoxy, Ci-C6-Alkylthio, Ci-C6-Halogenalkylthio, Ci-C6-Alkylsulfinyl, CI-CÖ- Halogenalkylsulfinyl, Ci-C6-Alkylsulfonyl oder Ci-C6-Halogenalkylsulfonyl substituiertes CI-CÖ- Alkyl, Ci-C6-Alkoxy, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, Ci-C6-Alkoxy oder Ci-C6-Halogenalkoxy substituiertes C3-C6- Cycloalkyl, C3-C6-Cycloalkyl-Ci-C6-alkyl, C3-C6-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N- Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-l -oxid, N-Thiomorpholinyl-l , l -dioxid, N- Piperazinyl, N-l -Methylpiperazinyl und N-2-Oxo-l -methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, C3-C6- Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-C6-Alkylthio, Ci-C6-Halogenalkylthio, Ci- C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci-Cö-Alkylsulfonyl, Ci-C6-Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, Ci-C6-Alkylcarbonylamino, CI-CÖ- Alkoxycarbonylamino, Ci-Ce-Alkoxy-Ci-Ce-alkyl, Ci-C6-Halogenalkoxy-Ci-C6-alkyl, C2-C6- Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Ci-C6-Alkylcarbonyl, Ci-C6- Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-Ci-C6-alkyl, Heteroaryl-Ci-C6-alkyl und NR'R" steht, worin R' und R" unabhängig voneinander jeweils für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, Ci-Cö-Haloalkyl, C3-C6-Cycloalkyl, CI-CÖ- Alkoxy, Ci-Cö-Alkylcarbonyl und Ci-C6-Alkoxylcarbonyl stehen, und R17 können im Rest (C-8) und im Rest (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, CI-CÖ- Alkyl, Ci-Cö-Halogenalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder eine Carbonylgruppe enthalten kann, insbesondere können R8 und R17 zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe R 16 is a radical from the series hydrogen, in each case optionally substituted by methyl, cyano, carbamoyl or carboxyl-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, in each case optionally by halogen, Cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -cycloalkyl Alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, CI-C Ö - haloalkylsulfonyl, amino, Ci-C6-alkylamino, di- (Ci-C6-alkyl) -amino, CI-CÖ-alkylcarbonylamino, Ci-C6 Alkoxycarbonylamino, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkylcarbonyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkenyl in which the rings are at least a heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each optionally substituted by halogen, cyano, nitro, Ci-Ce-alkyl, Ci-Ce- haloalkyl, C3-C6-Cyc loalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, CI-C Ö - haloalkylsulfonyl , Amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkynyl Alkylcarbonyl substituted aryl, heteroaryl, aryl-Ci-C 2 -alkyl and heteroaryl-Ci-C 2 -alkyl and optionally by Ci-Cö-alkyl, Ci-Cö-haloalkyl, C3-C6-cycloalkyl, Ci-C6-alkoxy , C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfmyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkylcarbonyl-substituted amino group, a radical from the series in each case optionally substituted by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio , Ci-C6-alkylsulfinyl, CI-COE haloalkylsulfinyl, Ci-C6-alkylsulfonyl or Ci-C6-haloalkylsulfonyl-substituted CI-C Ö - alkyl, Ci-C6 alkoxy, C 2 -C 6 alkenyl and C 2 -C6- Alkynyl, in each case optionally substituted by halogen, Ci-Cö-alkyl, Ci-Cö-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy-substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3 -C6-cycloalkenyl, N-pyrrolidinyl, N-piperidine yl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-l-oxide, N-thiomorpholinyl-l, l-dioxide, N-piperazinyl, Nl -methylpiperazinyl and N-2-oxo-l -methylpiperazinyl, each optionally with halogen , Cyano (also in the alkyl part), nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -cycloalkyl Haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkyl Alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -alkynyl cycloalkyl-Ci-Ce-alkyl, Ci-C6 alkylcarbonyl, Ci-C 6 - alkoxycarbonyl or aminocarbonyl substituted aryl, heteroaryl, aryl-Ci-C6-alkyl, heteroaryl-Ci-C6-alkyl, and NR'R ", wherein R 'and R "independently of one another in each case represent a radical from the series consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C C 1 -C 8 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl, and R 17 can also be used in radical (C-8) and in radical (F-8) together with the NC (X) group to which they are bonded, a saturated or unsaturated and optionally halogen, C 1 -C 8 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring form, the one or two further heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and may contain nitrogen and / or a carbonyl group, in particular R 8 and R 17 together with the NC (X) group to which they are attached, for a rest of the series
stehen (worin der Pfeil jeweils die Bindung zum S-Atom im Rest (C-8) und im Rest (F-8) markiert), und, im Fall, dass R2 für einen der unter f) aufgeführten Reste steht für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C2-C6-Halogenalkyl, Cyano-Ci-C6-alkyl, C2-C4-Alkenyl, C2-C i-Halogenalkenyl, C2-C4-Alkinyl, C2-C4-Halogenalkinyl, Ci-Ce-Alkoxy, Ci- C6-Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxy-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Bis(Ci-C6-alkoxy)-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkylsulfanyl-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkylcarbonyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci- C6-Alkylsulfinyl-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkylsulfonyl- Ci-Ce-alkyl, Di-(Ci-C6-alkyl)-aminosulfanyl-Ci-C6-alkyl, Di-(Ci-C6-alkyl)-aminosulfinyl-Ci-C6- alkyl, Di-(Ci-C6-alkyl)-aminosulfonyl-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxycarbonyl-Ci-C6-alkyl, gegebenenfalls durch Halogen substituiertes C2-C4- Alkinyloxy, Di-(Ci-C6-alkyl)-aminocarbonyl-Ci-C6-alkyl, N-Ci-C6-Alkyl-N-C3-C6- cycloalkylaminocarbonyl-Ci-C6-alkyl, Heterocyclylcarbonyl-Ci-C6-alkyl, Ci-C6-Alkylsulfanyl, Ci-C6-Halogenalkylsulfanyl, Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, CI-CÖ- Alkylsulfonyl, Ci-C6-Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, CI-CÖ- Alkyl, Ci-Ce-Halogenalkyl, Cs-Ce-Cycloalkyl, Ci-Ce-Alkoxy, Ci-Ce-Halogenalkoxy, Ci-Ce- Alkoxycarbonyl, Ci-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Ci-C6-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-C6-Alkoxycarbonyl, Ci-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Ci-Cö-Alkyl oder Halogen substituiert ist) substituiertes C3- C6-Cycloalkyl-Ci-C6-alkyl, gegebenenfalls durch Halogen, Cyano (auch im Ci-C6-Alkylteil von Heterocyclyl-Ci-C6-alkyl), Nitro, Hydroxy, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-Cö-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-Cö-Alkylthio, Ci-C6-Halogenalkylthio, CI-CÖ- Alkylsulfinyl, Ci-Cö-Alkylsulfonyl, Ci-C6-Halogenalkylsulfinyl, Ci-C6-Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, Ci-C6-Alkylcarbonylamino, CI-CÖ- Alkoxycarbonylamino, Ci-C6-Alkoxy-Ci-C6-alkyl, Ci-C6-Halogenalkoxy-Ci-C6-alkyl, C2-C6- Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Ci-C6-Alkylcarbonyl, Ci-C6- Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclyl-Ci-C6-alkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Ci-C6-Alkyl, Ci-C6-Halogenalkyl, C3-C6- Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-Cö-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C6-Alkoxy oder Ci-C6-Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im Ci-C6-Alkylteil von Aryl-Ci-C6-alkyl), Nitro, Hydroxy, Amino, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-Cö-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C6-Alkoxy oder CI-CÖ- Halogenalkoxy substituiertes Aryl-Ci-Cö-alkyl, gegebenenfalls durch Halogen, Cyano (auch im Ci-Ce-Alkylteil von Hetaryl-Ci-Ce-alkyl), Nitro, Hydroxy, Ci-Ce-Alkyl, Ci-C6-Halogenalkyl, C3- C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-Cö-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-C6-Alkylthio, Ci-C6-Halogenalkylthio, Ci-Ce-Alkylsulfmyl, Ci-Ce-Alkylsulfonyl, Ci-Ce-Halogenalkylsulfmyl, Ci-Ce- (in which the arrow in each case the bond to the S atom in the radical (C-8) and in the radical (F-8) labeled), and, in the case that R 2 is one of the radicals listed under f) is a radical is selected from hydrogen, Ci-COE-alkyl, C 2 -C 6 haloalkyl, cyano-Ci-C6-alkyl, C 2 -C 4 alkenyl, C 2 -C i-haloalkenyl, C 2 -C 4 alkynyl, C 2 C 4 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl optionally substituted by halogen, optionally bis-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl substituted by halogen alkyl, optionally halogen-substituted C 1 -C 6 -alkylsulfanyl-C 1 -C 6 -alkyl, optionally C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl which is substituted by halogen, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl optionally substituted by halogen, optionally substituted by halogen Ci-C6-alkylsulfonyl-Ci-Ce-alkyl, di- (Ci-C6-alkyl) -aminosulfanyl-Ci-C6-alkyl, di- (Ci-C6-alkyl) -aminosulfinyl-Ci-C6- alkyl, di (Ci-C6-alkyl) -aminosulfonyl-Ci-C6-alkyl, optionally by Hal oxy-substituted C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, optionally C 1 -C 4 -alkynyloxy substituted by halogen, di (C 1 -C 6 -alkyl) aminocarbonyl-C 1 -C 6 -alkyl, N-C 1 -C 6 -alkyl- N-C 3 -C 6 -cycloalkylaminocarbonyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, CI- CE - Alkylsulfonyl, Ci-C6-haloalkylsulfonyl, optionally substituted by halogen, cyano, nitro, CI-CÖ-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce Alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl or hetaryl (which is unsubstituted or substituted itself by C 1 -C 6 -alkyl or halogen), C 3 -C 6 -cycloalkyl which is substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, Haloalkyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by Ci-Cö-alkyl or halogen) substitui C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, where appropriate by halogen, cyano (also in the C 1 -C 6 -alkyl portion of heterocyclyl-C 1 -C 6 -alkyl), nitro, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -alkyl, Haloalkyl, C3-C6-cycloalkyl (which is optionally substituted by halogen, cyano, Ci-Cö-alkyl and C3-C6-cycloalkyl), Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-Cö-alkylthio, Ci C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -haloalkylsulfonyl, Amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxyamino Ci-C6-alkyl, C 2 -C6- alkenyl, C 2 -C 6 alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, Ci-C6 alkylcarbonyl, Ci-C 6 - alkoxycarbonyl or aminocarbonyl substituted heterocyclyl -Ci-C6-alkyl, optionally substituted by halogen, cyano, nitro, hydroxy, amino, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl (which is optionally substituted by halogen, cyano, Ci-Cö-alkyl and C 3 -C 6 -cycloalkyl is substituted), C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy-substituted aryl, where appropriate by halogen, cyano (also in the C 1 -C 6 -alkyl portion of aryl-C 1 -C 6 -alkyl), nitro, hydroxy, Amino, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is unsubstituted or substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 6 -alkoxy or C 1 -C 6 -cycloalkyl CÖ haloalkoxy-substituted aryl-Ci-Cö-alkyl, optionally substituted by halogen, cyano (also in the Ci-Ce-alkyl part of v on hetaryl-C 1 -C 6 -alkyl), nitro, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 Cycloalkyl is substituted), C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfmyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfmyl, Ce
Halogenalkylsulfonyl, Amino, Ci-C6-Alkylamino, Di-(Ci-C6-alkyl)-amino, CI-CÖ- Alkylcarbonylamino, Ci-C6-Alkoxycarbonylamino, Ci-C6-Alkoxy-Ci-C6-alkyl, CI-CÖ- Halogenalkoxy-Ci-Ce-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Ci-C6- Alkylcarbonyl, CI-CÖ- Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetaryl-Ci-C6-alkyl, und, im Fall, dass R2 für eine der unter c), d), oder f) aufgeführten Reste steht, auch für einen D-Rest aus der Reihe (D-l) bis (D-3) Haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-, haloalkoxy-Ci-Ce-alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, Ci-C 6 - alkylcarbonyl, CI-C Ö - alkoxycarbonyl or Aminocarbonyl substituted hetaryl-C 1 -C 6 -alkyl, and, in the case where R 2 is one of the radicals listed under c), d), or f), also represents a D radical from the series (Dl) to (D -3)
(D-1 ) (D-2) (D-3) worin für NR R oder für jeweils gegebenfalls durch Halogen, Sauerstoff (führt zu C=0) oder Cyano substituiertes Ci-Ce-Alkyl, C3-C6-Alkenyl, Cs-Ce-Alkinyl, Ci-C6-Alkoxy-Ci-C4-alkyl, Ci-C6- Alkyl-S-Ci-C4-alkyl, Ci-C6-Alkyl-S(0)-Ci-C4-alkyl, Ci-C6-Alkyl-S(0)2-Ci-C4-alkyl, für R18-CO- Ci-C4-alkyl, für NR18R19-CO-Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, C3-C8-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C8-Cycloalkenyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C6- Cycloalkyl-Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, Cs-Cö-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3- C6-Cycloalkenyl-Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, Cs-Cö-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), C1-C4- Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes Heterocyclyl-Ci- C4-alkyl oder für jeweils gegebenenfalls einfach bis dreifach durch Halogen, Cyano, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy substituiertes Phenyl, Phenyl-Ci-C4-alkyl, Hetaryl und Hetaryl-Ci-C4-alkyl steht, (D-1) (D-2) (D-3) wherein C 1 -C 6 -alkenyl which is substituted by NR, halogen or oxygen (resulting in C = O) or cyano is C 1 -C 6 -alkyl , Cs-Ce-alkynyl, Ci-C 6 alkoxy-Ci-C4-alkyl, Ci-C 6 - alkyl-S-Ci-C4-alkyl, Ci-C 6 alkyl-S (0) -C C 4 alkyl, C 1 -C 6 alkylS (O) 2 -Ci-C 4 alkyl, for R 18 -CO-C 1 -C 4 alkyl, for NR 18 R 19 -CO-Ci-C 4 alkyl, optionally substituted once or twice by oxygen 3 -C (leading to C = 0) Ci-C 4 alkyl, C 8 -cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl substituted C 3 -C 6 -cycloalkyl, optionally C3-C8-substituted by oxygen (leading to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl optionally substituted once or twice Cycloalkenyl, for optionally mono- or disubstituted by oxygen (leads to C = 0), Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted C3-C6-cycloalkyl-Ci-C4 C 3 -C 6 -cycloalkenyl-C 1 -C 4 -alkyl which is optionally monosubstituted or disubstituted by oxygen (leads to C = 0), C 1 -C 4 -alkyl, C 5 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl C4-alkyl, optionally substituted once or twice by oxygen (leads to C = 0), Ci-C4-alkyl, Cs-Cö-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted heterocyclyl, optionally optionally mono- or di-twice by oxygen (leads to C = 0), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted heterocyclyl-C 1 -C 4 -alkyl or in each case optionally monosubstituted to trisubstituted a by halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted phenyl, phenyl-C 1 -C 4 -alkyl, hetaryl and hetaryl C 1 -C 4 -alkyl,
X1 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Ci-Ce-Alkyl, Ci-Ce- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy und Ci-C6-Halogenalkoxy steht, X 1 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy,
Y3 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Ci-Cö-Alkyl, Ci-C6-Halogenalkyl, C3- Ce-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy und NR20R21 steht, Y 3 is a radical selected from hydrogen, halogen, cyano, Ci-COE-alkyl, Ci-C6-haloalkyl, C3-Ce-cycloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, and NR 20 R 21 stands,
W für einen Rest aus der Reihe S, SO und SO2 steht, W is a radical from the series S, SO and SO2,
R18 für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituiertes Ci-Cö-Alkyl, Ci-C6-Alkoxy, Ci-C6-Alkoxy-Ci-C4-alkyl, Ci-C6-Alkyl-S-Ci-C4-alkyl, Ci-C6-Alkyl-S(0)-Ci-C4-alkyl, Ci-C6- Alkyl-S(0)2-Ci-C4-alkyl, Ci-C6-Alkylcarbonyl, Ci-C6-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6- Cycloalkenyl, C3-C6-Cycloalkyl-Ci-C3-alkyl, C3-C6-Cycloalkenyl-Ci-C3-alkyl, Heterocyclyl, Heterocyclyl-Ci-C3-alkyl und jeweils gegebenenfalls einfach bis vierfach durch Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, C3-C6-Cycloalkyl, Halogen oder Cyano substituiertes Phenyl, Phenyl-Ci-C3-alkyl, Hetaryl und Hetaryl-Ci-C3-alkyl steht, R 18 is a radical from the series consisting of hydrogen, hydroxyl, in each case optionally monosubstituted or polysubstituted by halogen or mono- or disubstituted by cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 - alkyl, Ci-C 6 alkyl-S-Ci-C4-alkyl, Ci-C 6 alkyl-S (0) -C C-4 alkyl, Ci-C 6 - alkyl-S (0) 2 - Ci-C4-alkyl, Ci-C6 alkylcarbonyl, Ci-C 6 alkoxycarbonyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - cycloalkenyl, C3-C6-cycloalkyl-Ci-C3-alkyl, C3 C6-cycloalkenyl-Ci-C3-alkyl, heterocyclyl, heterocyclyl-Ci-C3-alkyl and in each case optionally mono- to tetrasubstituted by Ci-C 4 alkyl, Ci- C4 haloalkyl, Ci-C4-alkoxy, Ci- C 4 haloalkoxy, C 3 -C 6 -cycloalkyl, halogen or cyano-substituted phenyl, phenyl-C 1 -C 3 -alkyl, hetaryl and hetaryl-C 1 -C 3 -alkyl,
R19 für Wasserstoff, ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch Ci-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkyl-S-Ci-C4-alkyl, C1-C4- Alkyl-S(0)-Ci-C4-alkyl und Ci-C4-Alkyl-S(0)2-Ci-C4-alkyl steht, im Fall, dass R2 für einen der unter f) aufgeführten Reste steht R 19 represents hydrogen, an alkali or alkaline earth metal ion or an optionally monosubstituted to cis-C 4 -alkyl-substituted ammonium ion or an optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted radical from the series Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S-Ci-C4-alkyl, C1-C4 alkyl-S (0 ) -Ci-C 4 -alkyl and Ci-C 4 -alkyl-S (0) 2 -Ci-C 4 -alkyl, in the case that R 2 is one of the radicals listed under f)
R22 auch für einen der E-Reste (E- 1 ) bis (E- 11 ) R 22 also for one of the E radicals (E-1) to (E-11)
E-26 -62- E-26 -62-
E-37 E-38 E-39 E-40  E-37 E-38 E-39 E-40
steht, stands,
R für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy, Ci-C6-Alkyl, Ci-Ce-Halogenalkyl, Cyano-Ci-Ce-alkyl, C2-Ce-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C i-Alkyl und C3-C6-Cycloalkyl substituiert ist), C3-C6-Cycloalkyl-Ci-C6-alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C3-C6-Alkenyloxy, C3- Cö-Alkinyloxy, C3-C6-Cycloalkyloxy, Ci-Cö-Alkylcarbonyloxy, C2-C6-Alkenylcarbonyloxy, C2- Cö-Alkinylcarbonyloxy, C3-C6-Cycloalkylcarbonyloxy, Ci-C6-Alkoxycarbonyloxy, CI-CÖ- Alkylsulfonyloxy, Ci-C6-Alkylamino, C3-C6-Alkenylamino, C3-C6-Alkinylamino, C3-C6- Cycloalkylamino, Ci-C6-Alkylthio, Ci-C6-Halogenalkylthio, C3-C6-Alkenylthio, C3-C6- Alkinylthio, C3-C6-Cycloalkylthio, Ci-Ce-Alkylsulfinyl, Ci-Ce-Alkylsulfonyl, Ci-C6- Alkylcarbonyl, Ci-C6-Alkoxyimino-Ci-C6-alkyl, Ci-C6-Alkoxycarbonyl, Aminocarbonyl, CI-CÖ- Alkylaminocarbonyl, Di-(Ci-C6-alkyl)-aminocarbonyl, Aminothiocarbonyl, CI-CÖ- Alkylaminosulfonyl, Ci-C6-Alkylsulfonylamino, Ci-C6-Alkylcarbonylamino, CI-CÖ- Alkylthiocarbonylamino, jeweils gegebenenfalls durch einen Rest aus der Reihe Halogen, Cyano, Nitro, Amino, Hydroxy, Ci-Cö-Alkyl oder Ci-Cö-Halogenalkyl substituiertes Phenyl, Phenoxy, Pyridinyl und Pyridinyloxy steht, R is a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C -alkenyl, C 2 -C 6 Alkynyl, Cs-Ce-cycloalkyl (which is optionally substituted by halogen, cyano, Ci-C i-alkyl and C3-C6-cycloalkyl), C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 -alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, ci C 6 -alkoxycarbonyloxy, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 -alkynylamino, C 3 -C 6 -cycloalkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -alkoxy alkenylthio, C3-C6 alkynylthio, C 3 -C 6 cycloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-C 6 - alkylcarbonyl, Ci-C6-alkoxyimino-Ci-C6-alkyl, Ci-C6 alkoxycarbonyl, aminocarbonyl, CI-C Ö - alkylaminocarbonyl, di- (Ci-C6-alkyl) aminocarbonyl, aminothiocarbonyl, Cl-C Ö - alkylaminosulfonyl , C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkylthiocarbonylamino, in each case optionally by a radical from the series halogen, cyano, Is nitro, amino, hydroxy, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl-substituted phenyl, phenoxy, pyridinyl and pyridinyloxy,
R21 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C3-C6-Cycloalkyl, Ci-Cö-Halogenalkyl, C3-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, Cyano-Ci-C6-alkyl, Ci-C6- Alkylcarbonyl, C2-C6-Alkenylcarbonyl, Ci-C6-Halogenalkylcarbonyl, C2-C6-R 21 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl Ci-Ce-alkyl, cyano-Ci-C 6 alkyl, C 6 - alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, Ci-C6-haloalkylcarbonyl, C 2 -C6-
Halogenalkenylcarbonyl, Ci-C6-Alkoxy-Ci-C6-alkyl, Ci-C6-Alkoxycarbonyl, Ci-Cö-Alkylsulfonyl und Ci-C6-Halogenalkylsulfonyl steht, Haloalkenylcarbonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl,
R23 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6- Cycloalkyl, C3-C6-Cycloalkenyl, Ci-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6- Alkinyloxy, C3-C6- Cycloalkyloxy, Ci-C4-Alkylthio-Ci-C4-alkyl, C2-C4-Alkenylthio-Ci- C4-alkyl, Cyano-Ci-C4- alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl steht, oder, wenn R2 für einen der unter f) aufgeführten Reste steht, R 23 is a radical from the group of hydrogen, Ci-COE-alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C3-C6 cycloalkyl, C3-C6-cycloalkenyl, Ci-C6-alkoxy, C2- C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 4 -alkoxy-C 1 -C 4 -alkyl, or, if R 2 is one of the radicals listed under f),
R22 und R23 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gesättigten R 22 and R 23 together with the nitrogen atom to which they are attached, a saturated
bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und enthalten kann, und  form, which may contain one or two further heteroatoms from the series nitrogen, oxygen and, and
R24 für Wasserstoff oder einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Phenyl und Phenyl-Ci-C2-alkyl steht, R 24 is hydrogen or a radical optionally substituted by halogen or cyano radical from the series Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-Ci-C 2 alkyl stands,
R25 für Wasserstoff oder einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, C2-Ce-Alkenyl, C2-C6-Alkinyl, Phenyl und Phenyl-Ci-C2-alkyl steht, R 25 is hydrogen or in each case optionally substituted by halogen or cyano radical from the series Ci-C 4 alkyl, C 2 -Ce-alkenyl, C 2 -C 6 -alkynyl, phenyl and phenyl-Ci-C 2 alkyl,
R27 für Wasserstoff oder Ci-C4-Alkyl steht und R 27 is hydrogen or C 1 -C 4 -alkyl and
R26 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C2-C4-Alkenyl, C2- C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C2-alkyl, Ci-C6- Alkylsulfanyl, Ci-C6-Halogenalkylsulfanyl Ci-C6-Alkylsulfinyl, Ci-C6-Halogenalkylsulfinyl, Ci- Ce-Alkylsulfonyl, Ci-C4-Alkylthio-Ci-C2-alkyl, Ci-C4-Alkylsulfmyl-Ci-C2-alkyl, C1-C4- Alkylsulfonyl-Ci-C2-alkyl und Cyano-Ci-C4-alkyl steht. R 26 is a radical from the group of hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, C 3 -C 6 cycloalkyl, C3- C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 2 alkyl, Ci-C 6 - alkylsulfanyl, Ci-C6-Halogenalkylsulfanyl Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci- Ce-alkylsulfonyl, Ci-C4-alkylthio-Ci-C 2 alkyl, Ci-C 4 -Alkylsulfmyl-Ci-C 2 alkyl, C 1 -C4- alkylsulphonyl-Ci-C 2 alkyl, and cyano Ci-C 4 alkyl.
Vorzugsbereich (2): Besonders bevorzugt sind Verbindungen der Formel (I), worin Preferred range (2): Particular preference is given to compounds of the formula (I) in which
A für einen A-Rest aus der Reihe (A-b) und (A-f) A for an A-residue from the series (Ab) and (Af)
(A-b) (A-f) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, (A-b) (A-f), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I),
B2 für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C6-Alkyl und Ci-C i-Halogenalkyl steht, Q für Schwefel steht, R1 für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl und Ci-C i-Alkoxy steht, R2 a) für einen B-Rest aus der Reihe B 2 is a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C -haloalkyl, Q is sulfur, R 1 is a radical selected from the group consisting of hydrogen, C 1 -C -alkyl and carbonyl. C i-alkoxy, R 2 a) is a B radical from the series
(B-5) (B-6) B-7) (B-8) (B-5) (B-6) B-7) (B-8)
(B-9) (B-10) (B-l l) (B-12)  (B-9) (B-10) (B-1) (B-12)
(B-35) (B-36) (B-37)  (B-35) (B-36) (B-37)
(B-38) (B-39) (B-40) (B-41 ) (B-38) (B-39) (B-40) (B-41)
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder b) für einen D-Rest aus der Reihe (D- 1 ) bis (D-3) (B-42) (B-43) (B-44) (B-45), wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or b) a D radical of the series (D-1) to (D-3)
(D-1 ) (D-2) (D-3) „ (D-1) (D-2) (D-3) "
- 67 - steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder  Wherein the dashed line represents the bond to the carbon atom of the bicyclic compound of the formula (I), or
R2 c) für einen Rest der Formel R 2 c) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder d) für einen Rest der Formel wherein the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or d) a radical of the formula
X X
^ R22 ^ R22
R23 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder e) für einen F-Rest aus der Reihe (F-l), (F-8) und (F-10) R 23 is where the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or e) for an F radical from the series (Fl), (F-8) and (F-10)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom in der Formel (I) bedeutet, oder R2 f) für einen Rest der Formel wherein the dotted line represents the bond to the carbon atom in the formula (I), or R 2 f) represents a radical of the formula
- / R22 - / R 22
I  I
R  R
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder  wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R2 g) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, R 2 g) is a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Ci-C4-Alkylamino, Halogen-Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, C1-C4- Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, halogeniertes Ci-C4-Alkoxy-Ci-C4- alkyl, Bis(Ci-C4-alkoxy)-Ci-C4-alkyl, Bis(halogen-Ci-C4-alkoxy)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci- C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfmyl)-Ci-C4-alkyl, Ci-C4-Alkoxy- (Ci-C4-alkylsulfonyl)-Ci-C4-alkyl, Bis(Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(halogen-Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Bis(hydroxy-Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, C(X2)NR3R4, NR6R7, Ci-C4-Alkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Alkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Ci- C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxy und Ci-C4-Alkoxy-Ci-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Ci-C4-Alkyl und Halogen- Ci-C4-alkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxy, Halogen-Ci-C4-alkoxy, C1-C4- Alkoxy-Ci-C4-alkyl, Ci-C4-Alkylthio, Ci-C4-Alkylthio-Ci-C4-alkyl und C3-C6-Cycloalkyl) und die Heteroaryl-Ci-C4-alkylreste Triazolyl-Ci-C4-alkyl, Pyridyl-Ci-C4-alkyl, Pyrimidyl-Ci-C4-alkyl und Oxadiazolyl-Ci-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und Ci-C4-Alkyl), oder für einen C-Rest aus der Reihe (C- 1 ), (C-6) und (C-9) steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, G3 für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C6-Alkyl und Ci-C6-Halogenalkyl steht, is hydrogen or a radical from the series halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno-C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkyl, halogen C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkyl) 4 -alkoxy) -Ci-C 4 -alkyl, bis (halo-C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfanyl) -Ci-C 4- alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfinyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfonyl) C 1 -C 4 -alkyl, bis (Ci-C 4 alkylsulphanyl) -C-C 4 alkyl, bis (halo-Ci-C 4 - alkylsulfanyl) -C-C4-alkyl, bis (hydroxy-Ci-C4-alkylsulfanyl) -C-C4-alkyl , Ci-C4-alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl, C (X 2) NR 3 R 4, NR 6 R 7, C 4 alkylthio, Ci-C4 alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyloxide, O xathiolanyloxide, oxathialpanyloxide, oxathiocanyloxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may be substituted by C 1 -C 4 -alkyl, haloC 1 -C 4 -alkyl , C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl), phenyl (which in turn may itself be substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl and halogen-C 1 -C 4 -alkyl) in which the heteroaryl radicals are pyridyl, pyridyl-N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which themselves may be substituted by halogen, Nitro, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl) and the ethers roaryl-C 1 -C 4 -alkyl radicals triazolyl-C 1 -C 4 -alkyl, pyridyl-C 1 -C 4 -alkyl, pyrimidyl-C 1 -C 4 -alkyl and oxadiazolyl-C 1 -C 4 -alkyl (which in turn may themselves be substituted by halogen and C 1 -C 4 -alkyl), or for a C radical from the series (C-1), (C-6) and (C-9) in which the dashed line denotes the bond to the B radicals, G 3 represents a radical from the series consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl,
X für Sauerstoff steht, X stands for oxygen,
XI für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Jod, Cyano, Nitro, Ci-C i-Alkyl, Ci- C i-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C i-Alkoxy und Ci-C4-Halogenalkoxy steht, X I is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkyl -C 4 haloalkoxy,
X2 für Sauerstoff, Schwefel, NR5 oder NOH steht, n für 2 steht, X 2 is oxygen, sulfur, NR 5 or NOH, n is 2,
R für NR18R19 oder für jeweils gegebenfalls einfach bis siebenfach durch Halogen, einfach oder zweifach durch Sauerstoff (führt zu C=0) oder einfach oder zweifach durch Cyano substituiertes Ci-Ce-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, Ci-C4-Alkoxy-Ci-C3-alkyl, Ci-C4-Alkyl-S-Ci-C3- alkyl, Ci-C4-Alkyl-S(0)-Ci-C3-alkyl, Ci-C4-Alkyl-S(0)2-Ci-C3-alkyl, für R18-CO-Ci-C2-alkyl, für NR18R19-CO-Ci-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3- C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4- Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-Cs- Cycloalkenyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4- Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl- Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), C1-C4- Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C6- Cycloalkenyl-Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), C1-C4- Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes Heterocyclyl-Ci- C4-alkyl oder für jeweils gegebenenfalls einfach bis dreifach durch Halogen, Cyano, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy substituiertes Phenyl, Phenyl-Ci-C4-alkyl, Hetaryl und Hetaryl-Ci-C4-alkyl steht, R is NR 18 R 19 or, if appropriate, monosubstituted to trisubstituted by halogen, monosubstituted or disubstituted by oxygen (leads to C = 0) or mono- or disubstituted by cyano-substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 alkynyl, Ci-C 4 -alkoxy-Ci-C 3 alkyl, Ci-C4-alkyl-S-Ci-C 3 - alkyl, Ci-C 4 alkyl-S (0) -C C 3 alkyl, C 1 -C 4 alkylS (O) 2 -Ci-C 3 alkyl, for R 18 -CO-C 1 -C 2 alkyl, for NR 18 R 19 -CO-Ci-C 2 -alkyl which is optionally monosubstituted or disubstituted by oxygen (leading to C = 0) Ci-C4 alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy and Ci-C 4 -halogenoalkyl-substituted C 3 - C6-cycloalkyl, optionally substituted once or twice by oxygen (leading to C = 0) Ci-C 4 - alkyl, C 3 -C 6 cycloalkyl, Ci-C4-alkoxy and Ci-C 4 -halogenoalkyl-substituted C 3 - Cs cycloalkenyl, optionally substituted once or twice by oxygen (leading to C = 0) Ci-C 4 - alkyl, C 3 -C 6 cycloalkyl, Ci-C4-alkoxy and Ci-C 4 -halogenoalkyl-substituted C 3 - C6-cy oalkyl- Ci-C 4 alkyl, optionally substituted once or twice by oxygen (leading to C = 0), C1-C4 alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl substituted C 3 -C 6 -cycloalkenyl-C 1 -C 4 -alkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = 0), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and Ci-C 4 haloalkyl substituted heterocyclyl, mono- or di-optionally substituted by oxygen (leading to C = 0), C1-C4 alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy and Ci-C 4 - haloalkyl substituted heterocyclyl-Ci- C4-alkyl or represents in each case optionally mono- to trisubstituted by halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyl, Ci-C 4 alkoxy or Ci-C4-haloalkoxy, phenyl-Ci-C4-alkyl, hetaryl and hetaryl-Ci-C4 -alkyl,
R3 für Ci-C4-Alkyl steht, für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl und Ci-C4-Alkylthio-Ci-C4-alkyl steht, R 3 is C 1 -C 4 -alkyl, a radical selected from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 - C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl and C 1 -C 4 -alkyl 4- alkylthio-C 1 -C 4 -alkyl,
R5 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl und Ci-C4-Alkylthio-Ci-C4-alkyl steht, R 5 is a radical from the group of hydrogen, Ci-C 4 alkyl, halo-Ci-C4-alkyl, cyano-Ci-C 4 alkyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl , C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R6 für Wasserstoff oder Ci-C4-Alkyl steht, R 6 is hydrogen or C 1 -C 4 -alkyl,
R7 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, Ci-C4-Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Aryl-Ci-C4- alkyl oder Hetaryl-Ci-C4-alkyl steht, oder R 7 is a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, halogen -C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-Ci- -C 4 alkyl, aryl-Ci-C 4 - alkyl is or hetaryl-Ci-C4 alkyl, or
R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann, R8 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, Cyano-Ci-C6-alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C2-C6-Alkenyl, Ci-C6-Alkoxy-Ci-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes Ci-Cö-Alkylcarbonyl und Ci-Cö-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Ci-Ce- Alkoxycarbonyl und gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkyl und Cyano substituiertes C3-C6- Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch Ci-Cö-Alkyl oderR 6 and R 7, together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (with oxygen and sulfur atoms not being immediately adjacent R 8 is a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 Alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, in each case optionally halogen-substituted C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkylsulfonyl, optionally C 1 -C 4 -alkoxycarbonyl which is substituted by halogen and optionally by halogen, C 1 -C 6 -alkylcarbonyl Alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or represents a cation or an optionally C 1 -C 6 -alkyl or
Aryl-Ci-Cö-alkyl substituiertes Ammonium-Ion steht, Aryl-C 1 -C 6 -alkyl-substituted ammonium ion,
9 9
R für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C4-Alkoxy, C1-C4- Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, C1-C4- Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl und Ci-C4-Halogenalkylsulfonyl substituiertes C1-C4- Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-C4-Alkyl, Ci-R represents a radical from the series in each case optionally substituted by halogen, Ci-C4 alkoxy, C1-C4 haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl-substituted C 1 -C 4 - alkyl, C 2 -C 4 alkenyl and C 2 -C 4 alkynyl each optionally substituted by halogen, Ci-C 4 - Alkyl,
C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C4-alkyl und C3-C4-Cycloalkenyl, in welchen ein oder zwei Ringglieder jeweils durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein können (und dabei insbesondere für C 4 haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy-substituted C3-C6-cycloalkyl, C3-C6 cycloalkyl-Ci-C4-alkyl and C3-C4 cycloalkenyl, in which one or two Ring members in each case by a heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
wobei der Pfeil jeweils die Bindung zum S-Atom in dem Rest (C-l) und im Rest (F-l) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C i-Alkyl, C1-C4- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C i-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, C1-C4- Halogenalkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl, C1-C4- Halogenalkylsulfonyl, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, C1-C4- Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, C1-C4- Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl- Ci-C4-alkyl und Heteroaryl-Ci-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und Ci-C4-Alkyl stehen, oder wherein the arrow in each case marks the bond to the S atom in the radical (Cl) and in the radical (F1), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C -alkyl, C 1 -C 4 -alkyl Haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl , C 1 -C 4 -haloalkylsulphonyl, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 - C4- alkylcarbonyl, Ci-C4-alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-Ci-C4-alkyl and heteroaryl-Ci-C4-alkyl or NR'R ", wherein R 'and R" independently represent a radical from the series hydrogen and Ci-C4-alkyl, or
R8 und R9 können im Rest (C-l) und im Rest (F-l) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, CI-CÖ- Alkyl, Ci-Cö-Halogenalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine und bevorzugt genau eine Carbonylgruppe enthalten kann, insbesondere können R8 und R9 zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe R 8 and R 9 in the radical (Cl) and in the radical (Fl) can also be used together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally halogen, CI-CÖ-alkyl, Ci -Cö-haloalkyl, Ci-C 6 alkoxy, Ci-C6-haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably contain exactly one carbonyl group, in particular R 8 and R 9 may together with the NS (0) n group to which they are attached, stand for a residue from the series
stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert), R15 für einen Rest aus der Reihe jeweils gegebenenfalls durch Methyl substituiertes Ci-Cö-Alkyl, C2- Cö-Alkenyl und C2-C6-Alkinyl und jeweils gegebenenfalls durch Methyl, Halogen, Cyano oder Carbamoyl substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C2-alkyl und C3-C6- Cycloalkenyl steht, (wherein the arrow in each case marks the bond to the C (X) group), R 15 is a radical from the series each optionally substituted by methyl Ci-Cö-alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl and each optionally substituted by methyl, halogen, cyano or carbamoyl substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl and C3-C6-cycloalkenyl,
R8 und R15 im Rest (C-6) auch zusammen mit der N-S(0)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C i-Alkoxy, C1-C4- Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, C1-C4- Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl und Ci-C4-Halogenalkylsulfonyl substituiertes C1-C4- Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C4-alkyl, C3-C4-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N- Thiomorpholinyl, N-Thiomorpholinyl-l -oxid, N-Thiomorpholinyl-l , l -dioxid, N-Piperazinyl, N-l - Methylpiperazinyl und N-2-Oxo-l -methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4- Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, Amino, C1-C4- Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-Ci-C4-alkyl und Heteroaryl-Ci-C4-alkyl oder für NR'R"steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und Ci-C4-Alkyl stehen, für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituiertes Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkyl-S-Ci-C3-alkyl, Ci-C4-Alkyl-S(0)-Ci-C3-alkyl, C1-C4- Alkyl-S(0)2-Ci-C3-alkyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C3-alkyl, Heterocyclyl, Heterocyclyl-Ci-C3-alkyl und jeweils gegebenenfalls einfach bis dreifach durch Ci-C4-Alkyl, Ci-C3-Halogenalkyl, Ci-C3-Alkoxy, C1-C3- Halogenalkoxy, Cyclopropyl, Fluor Chlor, Brom oder Cyano substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl und Thiazolylmethyl steht, für Wasserstoff, für ein Alkali- oder Erdalkalimetallion, für ein gegebenfalls einfach bis vierfach durch Ci-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C2-alkyl, Ci-C4-Alkyl-S-Ci-C2-alkyl, C1-C4- Alkyl-S(0)-Ci-C2-alkyl und Ci-C4-Alkyl-S(0)2-Ci-C2-alkyl steht, für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Jod, Cyano, Ci-C4-Alkyl, C1-C4- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkoxy steht, für einen Rest aus der Reihe S, SO und SO2 steht, für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl, C2-C4-Halogenalkyl, Cyano-Ci-C4-alkyl, C2- C4-Alkenyl, C2-C4-Halogenalkenyl, C2-C4-Alkinyl, C2-C4-Halogenalkinyl, Ci-C4-Alkoxy, C1-C4- Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Ci-C2-Alkoxy-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Bis(Ci-C2-alkoxy)-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkylsulfanyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkylcarbonyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci- C4-Alkylsulfinyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkylsulfonyl- Ci-C4-alkyl, Di-(Ci-C4-alkyl)-aminosulfanyl-Ci-C4-alkyl, Di-(Ci-C4-alkyl)-aminosulfinyl-Ci-C4- alkyl, Di-(Ci-C4-alkyl)-aminosulfonyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkoxycarbonyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkoxycarbonyl-Ci- C4-alkyl, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxy, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxycarbonyl, Di-(Ci-C4-alkyl)-aminocarbonyl, N-C1-C4- Alkyl-N-C3-C6-cycloalkylaminocarbonyl, Di-(Ci-C4-alkyl)-aminocarbonyl-Ci-C4-alkyl, N-C1-C4- Alkyl-N-C3-C6-cycloalkylaminocarbonyl-Ci-C4-alkyl, Heterocyclylcarbonyl-Ci-C4-alkyl, C1-C4- Alkylsulfanyl, Ci-C4-Halogenalkylsulfanyl, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci- C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Ci- C4-Alkyl, Ci-C4-Halogenalkyl, Cs-Ce-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, C1-C4- Alkoxycarbonyl, Ci-C4-Halogenalkoxycarbonyl oder Pyridyl (welches gegebenenfalls selbst durch Ci-C4-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkoxycarbonyl, Ci-C4-Halogenalkoxycarbonyl oder Pyridyl (welches gegebenenfalls selbst durch Ci-C4-Alkyl oder Halogen substituiert ist) substituiertes C3- Ce-Cycloalkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Ci-C4-Alkyl, C1-C4- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkoxycarbonyl, Ci-C4-Halogenalkoxycarbonyl, Pyridyl, Pyrimidyl, Pyrazanyl, Pyridazinyl, Thiazolyl, Isothiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Oxadiazolyl, Pyrazolyl, Triazinyl oder Triazolyl (wobei die genannten Hetaryle gegebenenfalls selbst durch Ci-C4-Alkyl oder Halogen substituiert sind) substituiertes C3-C6-Cycloalkyl-Ci-C4-alkyl, gegebenenfalls durch Halogen, Cyano (auch im Ci-C4-Alkylteil von Heterocyclyl-Ci-C4-alkyl), Nitro, Hydroxy, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C4-Alkyl und C3-C6- Cycloalkyl substituiert ist), Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, C1-C4- Halogenalkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfinyl, C1-C4- Halogenalkylsulfonyl, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, C1-C4- Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, C1-C4- Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclyl-Ci-C4- alkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Ci-C i-Alkyl, C1-C4- Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im Ci-C4-Alkylteil von Aryl-Ci-C4-alkyl), Nitro, Hydroxy, Amino, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C4-Alkoxy oder Ci- C4-Halogenalkoxy substituiertes Aryl-Ci-C4-alkyl, gegebenenfalls durch Halogen, Cyano (auch im Ci-C4-Alkylteil von Hetaryl-Ci-C4-alkyl), Nitro, Hydroxy, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C4-Alkyl und C3-C6- Cycloalkyl substituiert ist), Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, C1-C4- Halogenalkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfinyl, C1-C4- Halogenalkylsulfonyl, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, C1-C4- Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, C1-C4- Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetaryl-Ci-C4-alkyl, oder für einen D-Rest aus der Reihe (D- 1 ) bis (D-3) R 8 and R 15 in the radical (C-6) together with the NS (0) n group to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or two further heteroatoms from the series sulfur, oxygen (where Oxygen and sulfur atoms may not be immediately adjacent) and may contain nitrogen and / or at least one carbonyl group, a radical from the series in each case optionally substituted by halogen, Ci-C i-alkoxy, C1-C4-haloalkoxy, Ci-C4-alkylthio , C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -halogenoalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl , in each case optionally substituted by halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy-substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3- C4-cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-l-oxide, N-thiomorpholinyl-l, l-dioxide, N-piperazinyl, Nl-methylpiperazinyl and N-2 Oxo-l -methylpiperazinyl, in each case optionally by halogen, cyano (also in the alkyl portion), nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloal koxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di (Ci C4-alkyl) amino, Ci-C4-alkylcarbonylamino, Ci-C4-alkoxycarbonylamino, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C 4 alkyl, C 2 C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-Ci-C4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or NR'R ", in which R 'and R" independently of one another represent a radical from the series consisting of hydrogen and C 1 -C 4 -alkyl, a radical from the series consisting of hydrogen, hydroxyl , in each case optionally monosubstituted or polysubstituted by halogen or mono- or disubstituted by cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl- S-Ci-C 3 alkyl, Ci-C 4 alkyl-S (0) -C-C 3 alkyl, C 1 -C4- alkyl-S (0) 2 -C-C 3 alkyl, Ci- C 4 alkylcarbon yl, Ci-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - cycloalkyl-Ci-C 3 alkyl, heterocyclyl, heterocyclyl-Ci-C 3 alkyl and in each case optionally mono- to trisubstituted by C C4-alkyl, Ci-C3 haloalkyl, Ci-C 3 alkoxy, C 1 -C 3 haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or cyano-substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, Furanyl, pyridinylmethyl and thiazolylmethyl, represents hydrogen, an alkali or alkaline earth metal ion, an optionally mono- to quadruply substituted by Ci-C 4 alkyl substituted ammonium ion or each optionally mono- or polysubstituted by halogen or mono- or cyano double-substituted radical from the series C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S-C 1 -C 2 -alkyl, C 1 -C 4 - alkyl-S (0) -CC-C 2 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, Iodine, cyano, C 1 -C 4 -alkyl, C 1 -C4- haloalkyl, C 3 -C 6 cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, is a radical from the series S, SO and SO2, a radical from the group of hydrogen, Ci-C i-alkyl, C 2 -C 4 haloalkyl, cyano-Ci-C4-alkyl, C 2 - C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, Ci-C4-alkoxy, C 1 -C 4 - haloalkoxy, optionally halogen-substituted Ci-C2-alkoxy-Ci-C4-alkyl optionally substituted by halogen bis (Ci-C 2 -alkoxy) -Ci-C4-alkyl, optionally substituted by halogen Ci-C4-alkylsulfanyl-Ci-C4-alkyl, optionally substituted by halogen Ci-C4-alkylcarbonyl-Ci-C4 C 1 -C 4 -alkylsulfinyl-C 1 -C 4 -alkyl optionally substituted by halogen, C 1 -C 4 -alkylsulfonyl-C 1 -C 4 -alkyl optionally substituted by halogen, or di- (C 1 -C 4 -alkyl) -aminosulfanyl-C 1 -C 4 -alkyl -alkyl, di (Ci-C4-alkyl) -aminosulfinyl-Ci-C4-alkyl, di (Ci-C4-alkyl) -aminosulfonyl-Ci-C4-alkyl, optionally substituted by halogen Ci-C4-Alkoxycarbonyl, if necessary halogen-substituted C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 alkyl, optionally halogen-substituted C2-C4-alkynyloxy, optionally halogen-substituted C2-C4-alkynyloxycarbonyl, di- (C1-C4-alkyl) -aminocarbonyl, N-C1-C4-alkyl-N-C3-C6-cycloalkylaminocarbonyl, Di- (C 1 -C 4 -alkyl) aminocarbonyl-C 1 -C 4 -alkyl, N-C 1 -C 4 -alkyl-N-C 3 -C 6 -cycloalkylaminocarbonyl-C 1 -C 4 -alkyl, heterocyclylcarbonyl-C 1 -C 4 -alkyl, C 1 C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, where appropriate by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl or pyridyl (which may optionally itself be substituted by C 1 -C 4 -alkyl or halogen is) substituted C3-C6-cycloalkyl, optionally substituted by halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, Ci-C 4 alkoxy, Ci-4 haloalkoxy C , Ci-C 4 alkoxycarbonyl, Ci-C 4 -Halogenal koxycarbonyl or pyridyl (which is optionally itself substituted by Ci-C4-alkyl or halogen) substituted C3-Ce-cycloalkylcarbonyl, optionally substituted by halogen, cyano, nitro, Ci-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl , C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, pyridyl, pyrimidyl, pyrazanyl, pyridazinyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, pyrazolyl, triazinyl or Triazolyl (where said hetaryl are optionally themselves substituted by Ci-C 4 alkyl or halogen) substituted C3-C6-cycloalkyl-Ci-C4-alkyl, optionally substituted by halogen, cyano (also in the Ci-C4-alkyl portion of heterocyclyl-Ci C 4 -alkyl), nitro, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkyl isulfonyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkyl Alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 - alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted heterocyclyl-C 1 -C 4 - alkyl, where appropriate by halogen, cyano, nitro, hydroxy, amino, C 1 -C -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl and C 3 -C 6 -Cycloalkyl substituted), Ci-C4-alkoxy or Ci-C4-haloalkoxy-substituted aryl, optionally substituted by halogen, cyano (also in the Ci-C 4 alkyl portion of aryl-Ci-C 4 -alkyl), nitro, hydroxy, amino , Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl (which is optionally substituted by halogen, cyano, Ci-C 4 alkyl, and C3-C6-cycloalkyl), Ci-C 4 alkoxy or C 1 -C 4 -haloalkoxy-substituted aryl-C 1 -C 4 -alkyl, where appropriate by halogen, cyano (also in the C 1 -C 4 -alkyl portion of hetaryl C 1 -C 4 -alkyl), nitro, hydroxy, C 1 -C 4 -alkyl , Ci-C4-haloalkyl, C3-C6-cycloalkyl (which is optionally substituted by halogen, cyano, Ci-C4-alkyl and C3-C6 cycloalkyl), Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-alkylthio, C1-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C 4-haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-ci- C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 C 1-4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted hetaryl-C 1 -C 4 -alkyl, or for a D radical from the series (D-1) to (D-3)
(D-1 ) (D-2) (D-3) oder einen der folgenden E-Reste (D-1) (D-2) (D-3) or one of the following E radicals
- 75 - - 75 -
E-49 E-51 steht, oder, im Fall, dass R2 für einen der unter d) aufgeführten Reste steht E-49 E-51 is, or, in the case that R 2 is one of the radicals listed under d)
R22 auch für den Rest (E- 13) R 22 also for the rest (E- 13)
E-13 steht, R23 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6- Cycloalkyl, C3-C6-Cycloalkenyl, Ci-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6- Cycloalkyloxy, Ci-C4-Alkylthio-Ci-C4-alkyl, C2-C4-Alkenylthio-Ci-C4-alkyl, Cyano-Ci-C4-alkyl und Ci-C4-Alkoxy-Ci-C4alkyl steht, oder, im Fall, dass R2 für einen der unter c) oder f) aufgeführten Reste steht R22 und R23 auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gesättigten vier- bis sechsgliedrigen Ring bilden können, der ein weiteres Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, E-13, R 23 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 Alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 -C 4 -alkyl, cyano-ci- C 4 -alkyl and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or, in the case where R 2 is one of the radicals listed under c) or f), R 22 and R 23 are also taken together with the nitrogen atom to which they are bonded to form a saturated four- to six-membered ring, which may contain another heteroatom from the series nitrogen, oxygen and sulfur,
R27 für Wasserstoff oder Ci-C4-Alkyl steht und R 27 is hydrogen or C 1 -C 4 -alkyl and
R26 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C2-C4-Alkenyl, C2- C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C2-alkyl, C1-C4-R 26 is a radical from the group of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 2 alkyl, C 1 -C4-
Alkylsulfanyl, Ci-C4-Halogenalkylsulfanyl, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci- C4-Alkylsulfonyl, Ci-C4-Alkylthio-Ci-C2-alkyl, Ci-C4-Alkylsulfmyl-Ci-C2-alkyl, C1-C4- Alkylsulfonyl-Ci-C2-alkyl und Cyano-Ci-C4-alkyl steht und Alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfmyl-ci C 2 -alkyl, C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl and cyano-C 1 -C 4 -alkyl and
Verbindungen der Formel (I), worin A für den A-Rest Compounds of the formula (I) in which A is the A radical
(A-a) „ (Aa) "
- 78 - steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,  Wherein the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
G1 für N oder C-B1 steht, G 1 is N or CB 1 ,
B1 für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-Cö-Alkyl und Ci-C i-Halogenalkyl steht, B2 für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-Cö-Alkyl und Ci-C/i-Halogenalkyl steht, B 1 is a radical selected from hydrogen, halogen, Ci-COE-alkyl and Ci-C i-haloalkyl, B 2 is a radical selected from hydrogen, halogen, Ci-COE-alkyl and Ci-C / i- Haloalkyl is
T für Sauerstoff oder ein Elektronenpaar steht, T is oxygen or a pair of electrons,
Q für Schwefel steht, Q stands for sulfur,
R1 für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl und Ci-C i-Alkoxy steht, R 1 is a radical selected from the group consisting of hydrogen, C 1 -C -alkyl and C 1 -C -alkoxy,
R2 a) für einen B-Rest aus der Reihe R 2 a) for a B residue from the series
(B-9) (B-10) (B-l l) (B-12) (B-9) (B-10) (B-1) (B-12)
(B-38) (B-39) (B-40) (B-38) (B-39) (B-40)
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Ci-C4-Alkylamino, Halogen-Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, C1-C4- Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, halogeniertes Ci-C4-Alkoxy-Ci-C4- alkyl, Bis(Ci-C4-alkoxy)-Ci-C4-alkyl, Bis(halogen-Ci-C4-alkoxy)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci- C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfmyl)-Ci-C4-alkyl, Ci-C4-Alkoxy- (Ci-C4-alkylsulfonyl)-Ci-C4-alkyl, Bis(Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(halogen-Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Bis(hydroxy-Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, C(X2)NR3R4, NR6R7, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, C1-C4- Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Ci- C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxy und Ci-C4-Alkoxy-Ci-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Ci-C4-Alkyl und Halogen- Ci-C4-alkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxy, Halogen-Ci-C4-alkoxy, C1-C4- Alkoxy-Ci-C4-alkyl, Ci-C4-Alkylthio, Ci-C4-Alkylthio-Ci-C4-alkyl und C3-C6-Cycloalkyl) und die Heteroaryl-Ci-C4-alkylreste Triazolyl-Ci-C4-alkyl, Pyridyl-Ci-C4-alkyl, Pyrimidyl-Ci-C4-alkyl und Oxadiazolyl-Ci-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und Ci-C4-Alkyl) steht, oder aa) für einen der folgenden B-Reste (B-42) (B-43) (B-44) (B- 45), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I) wherein, for hydrogen or a halogen radical, Nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno-C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl Alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 - alkyl, bis (halogeno-C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy - (C 1 -C 4 -alkylsulfmyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfonyl) C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkylsulfanyl) -Ci -C 4 alkyl, bis (halo-Ci-C 4 - alkylsulfanyl) -C-C4-alkyl, bis (hydroxy-Ci-C4-alkylsulfanyl) -C-C4-alkyl, Ci-C4-alkoxycarbonyl, Ci-C 4- alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkyl Halogenoalkylthio, Ci-C4-Halogenalkylsulfiny l, C 1 -C 4 -haloalkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, morpholinyl, Triazolinonyl, oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and Pyrazolinonyl (which itself may in turn be substituted by C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl), phenyl (which itself may in turn be substituted by halogen, cyano , Nitro, C 1 -C 4 -alkyl and halogen-C 1 -C 4 -alkyl), the heteroaryl radicals pyridyl, pyridyl-N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, Pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may themselves be substituted by halogen, nitro, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C1-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 alkylthio, Ci-C4-alkylthio-Ci-C 4 alkyl and C 3 -C 6 -cycloalkyl) and the heteroaryl-Ci-C4- alkyl radicals triazolyl-C 1 -C 4 -alkyl, pyridyl-C 1 -C 4 -alkyl, pyrimidyl-C 1 -C 4 -alkyl and oxadiazolyl-C 1 -C 4 -alkyl (which in turn may themselves be substituted by halogen and C 1 -C 4 -alkyl) , or aa) for one of the following B radicals
(B-31) (B-32) (B-31) (B-32)
(B-33) (B-35) (B-36) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet und worin für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Ci-C i-Alkylamino, Halogen-Ci-C i- Alkylamino, Di-(Ci-C4-alkyl)-amino, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, halogeniertes Ci-C4-Alkoxy-Ci-C4-alkyl, Bis(Ci-C4-alkoxy)-Ci-C4-alkyl, Bis(halogen-Ci-C4- alkoxy)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4- alkylsulfmyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfonyl)-Ci-C4-alkyl, Bis(Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Bis(halogen-Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(hydroxy-Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, C(X2)NR3R4, NR6R7, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, C1-C4- Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch C1-C4- Alkyl, Halogen-Ci-C4-alkyl, C1-C4- Alkoxy und Ci-C4-Alkoxy-Ci-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Ci-C4-Alkyl und Halogen-Ci-C4-alkyl), die Heteroarylreste Imidazolyl, Pyrazolyl, Oxazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkylthio, Ci-C4-Alkylthio-Ci-C4-alkyl und C3-C6-Cycloalkyl) und die Heteroaryl-Ci-C4-alkylreste Triazolyl-Ci-C4-alkyl, Pyridyl-Ci-C4- alkyl, Pyrimidyl-Ci-C4-alkyl und Oxadiazolyl-Ci-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und C1-C4- Alkyl) steht, oder wenn R2 für einen der unter a) oder aa) aufgeführten Reste steht, auch für einen C-Rest aus der Reihe (C-6) und (C-9) steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, oder R2 c) für einen Rest der Formel (B-33) (B-35) (B-36), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I) and wherein a group selected from the group consisting of halogen, nitro, amino, cyano, Ci -C 1 -alkylamino, halogeno-C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) amino, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkylamino, C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, bis (halogeno-C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- Ci-C4-alkylsulfanyl) -C-C 4 alkyl, Ci-C4-alkoxy- (Ci-C 4 - alkylsulfmyl) -C-C 4 alkyl, Ci-C4-alkoxy- (Ci-C 4 - alkylsulfonyl) -C-C 4 alkyl, bis (Ci-C 4 - alkylsulfanyl) -C-C4-alkyl, bis (halo-Ci-C4-alkylsulfanyl) -C-C4-alkyl, bis (hydroxy-Ci-C4 alkylsulfanyl) -CC-C4-alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxep Anyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl. dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, morpholinyl, Triazolinonyl, oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and Pyrazolinonyl (which in turn may be substituted by C 1 -C 4 alkyl, halo-C 1 -C 4 -alkyl, C 1 -C 4 alkoxy and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl), phenyl (which in turn is substituted may be halogen, cyano, nitro, C 1 -C 4 -alkyl and halogeno-C 1 -C 4 -alkyl), the heteroaryl radicals imidazolyl, pyrazolyl, oxazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, Tetrazinyl and isoquinolinyl (which in turn may themselves be substituted by halogen, nitro, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 4 alcohol xy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl) and the heteroaryl-C 1 -C 4 -alkyl radicals triazolyl-C 1 -C 4 -alkyl, pyridyl-C 1 -C 4 -alkyl, pyrimidyl-C 1 -C 4 -alkyl and oxadiazolyl-C 1 -C 4 -alkyl (which in turn may themselves be substituted by halogen and C 1 -C 4 -alkyl), or when R 2 stands for one of the radicals listed under a) or aa), also for a C radical from the series (C-6) and (C-9) wherein the dotted line represents the bond to the B radicals, or R 2 c) represents a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R2 d) für einen Rest der Formel R 2 d) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R2 e) für einen F-Rest aus der Reihe F-8) und (F-10) R 2 e) for an F radical from the series F-8) and (F-10)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom in der Formel (I) bedeutet, oder R2 f) für einen Rest der Formel wherein the dotted line represents the bond to the carbon atom in the formula (I), or R 2 f) represents a radical of the formula
- / R22 - / R 22
I  I
R steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
X für Sauerstoff steht, X stands for oxygen,
X2 für Sauerstoff, Schwefel oder NOH steht, n für 2 steht, X 2 is oxygen, sulfur or NOH, n is 2,
R3 für Ci-C4-Alkyl steht, R 3 is C 1 -C 4 -alkyl,
R4 für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C i-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl und Ci-C4-Alkylthio-Ci-C4-alkyl steht, R6 für Wasserstoff oder Ci-C4-Alkyl steht, R 4 is a radical selected from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl , C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, R 6 represents hydrogen or C 1 -C 4 -alkyl,
R7 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, Ci-C4-Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Aryl-Ci-C4- alkyl oder Hetaryl-Ci-C4-alkyl steht, oder R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann, R 7 is a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, halogen -C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-Ci- -C 4 alkyl, aryl-Ci-C 4 - alkyl or hetaryl-Ci-C 4 -alkyl, or R 6 and R 7 together with the nitrogen atom to which they are attached, a 4- to 7-membered ring which may contain one or two further heteroatoms selected from nitrogen, oxygen and sulfur (oxygen and sulfur atoms may not be immediately adjacent),
R8 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, Ci-C6-Halogenalkyl, Cyano-Ci-C6-alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C2-C6-Alkenyl, Ci-C6-Alkoxy-Ci-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes Ci-Cö-Alkylcarbonyl und Ci-Cö-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxycarbonyl und gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkyl und Cyano substituiertes C3-C6- Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch Ci-Cö-Alkyl oder Aryl-Ci-Cö-alkyl substituiertes Ammonium-Ion steht, R15 für einen Rest aus der Reihe jeweils gegebenenfalls durch Methyl substituiertes Ci-Cö-Alkyl, C2- Cö-Alkenyl und C2-C6-Alkinyl und jeweils gegebenenfalls durch Methyl, Halogen, Cyano oder Carbamoyl substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C2-alkyl und C3-C6- Cycloalkenyl steht, R 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by halogen, Ci-Cö-alkyl, Ci-C6 Alkoxy, Ci-C6-haloalkyl and cyano substituted C3-C6-cycloalkylcarbonyl, or represents a cation or an optionally substituted by Ci-Cö-alkyl or aryl-Ci-Cö-alkyl-substituted ammonium ion, R 15 is a radical from the series in each case optionally substituted by methyl Ci-Cö-alkyl, C2-Cö-alkenyl and C 2 -C6-alkynyl and in each case optionally substituted by methyl, halogen, cyano or carbamoyl C3-C6-cycloalkyl, C3-C6-cycloalkyl Ci-C2-alkyl and C3-C6-cycloalkenyl,
R8 und R15 im Rest (C-6) auch zusammen mit der N-S(0)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C i-Alkoxy, C1-C4- Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, C1-C4- Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl und Ci-C4-Halogenalkylsulfonyl substituiertes C1-C4- Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C4-alkyl, C3-C4-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N- Thiomorpholinyl, N-Thiomorpholinyl-l -oxid, N-Thiomorpholinyl-l , l -dioxid, N-Piperazinyl, N-l - Methylpiperazinyl und N-2-Oxo-l -methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Cs-Ce-Cycloalkyl, C1-C4- Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, Amino, C1-C4- Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-Ci-C4-alkyl und Heteroaryl-Ci-C4-alkyl oder für NR'R"steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und Ci-C4-Alkyl stehen, im Fall, dass R2 für einen der unter f) aufgeführten Reste steht, für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, C2-C4-Halogenalkyl, Cyano-Ci-C4-alkyl, C2- C4-Alkenyl, C2-C4-Halogenalkenyl, C2-C4-Alkinyl, C2-C4-Halogenalkinyl, Ci-C4-Alkoxy, C1-C4- Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Ci-C2-Alkoxy-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Bis(Ci-C2-alkoxy)-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkylsulfanyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkylcarbonyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci- C4-Alkylsulfinyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkylsulfonyl- Ci-C4-alkyl, Di-(Ci-C4-alkyl)-aminosulfanyl-Ci-C4-alkyl, Di-(Ci-C4-alkyl)-aminosulfinyl-Ci-C4- alkyl, Di-(Ci-C4-alkyl)-aminosulfonyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, gegebenenfalls durch Halogen substituiertes C2-C4- Alkinyloxy, Di-(Ci-C4-alkyl)-aminocarbonyl-Ci-C4-alkyl, N-Ci-C4-Alkyl-N-C3-C6- cycloalkylaminocarbonyl-Ci-C4-alkyl, Heterocyclylcarbonyl-Ci-C4-alkyl, Ci-C4-Alkylsulfanyl, Ci-C4-Halogenalkylsulfanyl, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, C1-C4- Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C4- Alkyl, Ci-C i-Halogenalkyl, Cs-Ce-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, C1-C4- Alkoxycarbonyl, Ci-C4-Halogenalkoxycarbonyl oder Pyridyl (welches gegebenenfalls selbst durch Ci-C4-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkoxycarbonyl, Ci-C4-Halogenalkoxycarbonyl, Pyridyl, Pyrimidyl, Pyrazanyl, Pyridazinyl, Thiazolyl, Isothiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Oxadiazolyl, Pyrazolyl, Triazinyl oder Triazolyl (wobei die genannten Hetaryle gegebenenfalls selbst durch Ci- C4- Alkyl oder Halogen substituiert sind) substituiertes C3-C6-Cycloalkyl-Ci-C4-alkyl, gegebenenfalls durch Halogen, Cyano (auch im Ci-C4-Alkylteil von Heterocyclyl-Ci-C4-alkyl), Nitro, Hydroxy, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C4-Alkoxy, C1-C4- Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, C1-C4- Alkylsulfonyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Amino, C1-C4- Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclyl-Ci-C4-alkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C4-Alkoxy oder C1-C4- Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im C1-C4- Alkylteil von Aryl-Ci-C4-alkyl), Nitro, Hydroxy, Amino, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3- C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy substituiertes Aryl-Ci-C4-alkyl, gegebenenfalls durch Halogen, Cyano (auch im Ci-C4-Alkylteil von Hetaryl-Ci-C4-alkyl), Nitro, Hydroxy, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, Ci-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), Ci-C4-Alkoxy, C1-C4- Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, C1-C4- Alkylsulfonyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Amino, C1-C4- Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetaryl-Ci-C4-alkyl, und im Fall, dass R2 für einen der unter c), d) oder f) aufgeführten Reste steht, auch für einen D-Rest aus der Reihe (D-l) bis (D-3) R 8 and R 15 in the radical (C-6) together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring may contain one or two further heteroatoms selected from the group consisting of sulfur, oxygen (oxygen and sulfur atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group; C 1 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 - C 4 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, in each case optionally C 3 -C 6 -substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-1-oxide, N-thiomorpholinyl-1, l-dioxide, N-piperazinyl, Nl - methylpiperazinyl and N-2-oxo-l -methylpiperazinyl, each optionally substituted by halogen, cyano (also in the alkyl portion), N itro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 - 6 cycloalkyl C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or NR'R ", in which R 3 'and R "independently represent a radical from the series of hydrogen and Ci-C4-alkyl, in the case that R 2 is one of the radicals listed under f), a radical selected from the group hydrogen, Ci-C4-alkyl , C 2 -C 4 haloalkyl, cyano-Ci-C4-alkyl, C 2 - C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, Ci-C4-alkoxy , C 1 -C4- haloalkoxy, optionally substituted by halogen, Ci-C2-alkoxy-Ci-C4-alkyl, optionally substituted bis (Ci-C 2 alkoxy) by halogen -C-C4-alkyl, optionally substituted by halogen, Ci- C 1 -C 4 -alkylsulfanyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl optionally substituted by halogen, C 1 -C 4 -alkylsulfinyl-C 1 -C 4 -alkyl optionally substituted by halogen, optionally C 1 -C 4 -substituted by halogen Alkylsulfonyl-C 1 -C 4 -alkyl, di- (C 1 -C 4 -alkyl) -aminosulfanyl-C 1 -C 4 -alkyl, di- (C 1 -C 4 -alkyl) -aminosulfinyl-C 1 -C 4 -alkyl, di- (C 1 -C 4 -alkyl -alkyl) -aminosulfonyl-C 1 -C 4 -alkyl, optionally C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl substituted by halogen, C 2 -C 4 -alkynyloxy optionally substituted by halogen, di- (C 1 -C 4 -alkyl) aminocarbonyl- C 1 -C 4 -alkyl, N-C 1 -C 4 -alkyl-N-C 3 -C 6 -cycloalkylaminocarbonyl-C 1 -C 4 -alkyl, heterocyclylcarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 Alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, where appropriate by halogen, cyano, nitro, C 1 -C 4 -alkyl, Alkyl, Ci-C i-haloalkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4alkoxycarbonyl, Ci-C4-haloalkoxycarbonyl or pyridyl (which may be itself by Ci-C4-alkyl or halogen is substituted) substituted C 3 -C 6 -cycloalkyl, if appropriate by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, pyridyl, pyrimidyl, pyrazanyl, pyridazinyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, pyrazolyl, triazinyl or triazolyl (where the said hetaryl is optionally itself substituted by C 1 -C 4 -alkyl substituted or halo) substituted C3-C6-cycloalkyl-Ci-C4-alkyl, optionally substituted by halogen, cyano (also in Ci-C 4 alkyl moiety of heterocyclyl-Ci-C4 alkyl), nitro, hydroxy, Ci-C 4- alkyl, Ci-C 4 -haloalkyl, C3-C6-cycloalkyl (which optionally substituted by halogen, cyano, Ci-C4-alkyl and C3-C6-cycloalkyl is), Ci-C4-alkoxy, C1-C4 haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C4 alkylsulfonyl, Ci-C4-haloalkylsulfinyl, Ci-C4- haloalkylsulfonyl, amino, C 1 -C 4 - alkylamino, di- (Ci-C4-alkyl) amino, Ci-C4-alkylcarbonylamino, Ci-C4-alkoxycarbonylamino, Ci-C4-alkoxy-Ci-C 4 alkyl , Ci-C4-haloalkoxy-Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 - 6 cycloalkyl-Ci-C4-alkyl, Ci-C 4 - alkylcarbonyl, Ci-C 4 alkoxycarbonyl or aminocarbonyl substituted heterocyclyl-Ci-C4-alkyl, optionally substituted by halogen, cyano, nitro, hydroxy, amino, Ci-C 4 alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted aryl, optionally by halogen, cyano (also in the C 1 -C 4 -alkyl portion of aryl-C 1 -C 4 -alkyl), nitro, hydroxy, amino, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl (which may be substituted by Halogen, cyano, C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl is substituted), C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted aryl-C 1 -C 4 -alkyl, where appropriate by halogen, cyano (also in the Ci-C 4- alkyl part of hetaryl-C 1 -C 4 -alkyl), nitro, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl is substituted), C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfinyl , C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-Ci C4-alkyl, Ci-C4-haloalkoxy-Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 - 6 cycloalkyl-Ci-C 4 alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted hetaryl-C 1 -C 4 -alkyl, and in the case where R 2 is one of the radicals listed under c), d) or f) e is also a D radical from the series (D1) to (D-3)
(D-1 ) (D-2) (°-3) steht, worin für NR18R19 oder für jeweils gegebenfalls einfach bis siebenfach durch Halogen, einfach oder zweifach durch Sauerstoff (führt zu C=0) oder einfach oder zweifach durch Cyano substituiertes Ci-Ce-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, Ci-C4-Alkoxy-Ci-C3-alkyl, Ci-C4-Alkyl-S-Ci-C3- alkyl, Ci-C4-Alkyl-S(0)-Ci-C3-alkyl, Ci-C4-Alkyl-S(0)2-Ci-C3-alkyl, für R18-CO-Ci-C2-alkyl, für NR18R19-CO-Ci-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3- C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), C1-C4- Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-Cs- Cycloalkenyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), C1-C4- Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl- Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), C1-C4- Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes C3-C6- Cycloalkenyl-Ci-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), Ci-C4-Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=0), C1-C4- Alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkyl substituiertes Heterocyclyl-Ci- C4-alkyl oder für jeweils gegebenenfalls einfach bis dreifach durch Halogen, Cyano, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy substituiertes Phenyl, Phenyl-Ci-C4-alkyl, Hetaryl und Hetaryl-Ci-C4-alkyl steht, für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Jod, Cyano, Nitro, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkoxy steht, für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Jod, Cyano, Ci-C4-Alkyl, C1-C4- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy und Ci-C4-Halogenalkoxy steht, für einen Rest aus der Reihe S, SO und SO2 steht, R für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituiertes Ci-C i-Alkyl, Ci-C i-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkyl-S-Ci-C3-alkyl, Ci-C4-Alkyl-S(0)-Ci-C3-alkyl, C1-C4- Alkyl-S(0)2-Ci-C3-alkyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C3-alkyl, Heterocyclyl, Heterocyclyl-Ci-C3-alkyl und jeweils gegebenenfalls einfach bis dreifach durch Ci-C4-Alkyl, Ci-C3-Halogenalkyl, Ci-C3-Alkoxy, Ci-C3- Halogenalkoxy, Cyclopropyl, Fluor Chlor, Brom oder Cyano substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl und Thiazolylmethyl steht, (D-1) (D-2) (° - 3 ), wherein for NR 18 R 19 or for any single to seven times by halogen, single or double by oxygen (leads to C = 0) or single or double cyano substituted Ci-Ce-alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, Ci-C 4 -alkoxy-Ci-C 3 alkyl, Ci-C4-alkyl-S-C 3 -alkyl, C 1 -C 4 -alkyl-S (0) -Cl-C 3 -alkyl, C 1 -C 4 -alkyl-S (O) 2- Ci-C 3 -alkyl, for R 18 -CO-Ci C 2 -alkyl, for NR 18 R 19 -CO-C 1 -C 2 -alkyl, for optionally mono- or disubstituted by oxygen (leads to C = 0), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, Ci-C4-alkoxy and Ci-C 4 -halogenoalkyl-substituted C 3 - 6 cycloalkyl, optionally monosubstituted or disubstituted by oxygen (leading to C = 0), C1-C4 alkyl, C 3 -C 6 cycloalkyl, C -C 4 alkoxy and Ci-C 4 -haloalkyl-substituted C 3 -CS- cycloalkenyl, optionally monosubstituted or disubstituted by oxygen (leading to C = 0), C1-C4 alkyl, C3-C6-cycloalkyl, Ci- C 4 alkoxy and Ci-C4 -Halogenalky l is substituted C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and Ci-C 4 -haloalkyl-substituted C 3 -C6- cycloalkenyl-Ci-C4-alkyl, optionally substituted once or twice by oxygen (leading to C = 0) Ci-C 4 alkyl, C 3 -C 6 cycloalkyl , Ci-C4-alkoxy and Ci-C4-haloalkyl substituted heterocyclyl, mono- or optionally disubstituted by oxygen (leading to C = 0), C1-C4 alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy and C 1 -C 4 -haloalkyl-substituted heterocyclyl-C 1 -C 4 -alkyl or, in each case optionally mono- to trisubstituted by halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted phenyl, phenyl-C 1 -C 4 -alkyl, hetaryl and hetaryl-C 1 -C 4 -alkyl, a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6- Cycloalkyl, Ci-C4-alkoxy and Ci-C4 haloalkoxy, a radical from the series comprising hydrogen, fluorine, chlorine, bromine, iodine, cyano, Ci-C4-alkyl, C1-C4 haloalkyl, C 3 - C6-cycloalkyl, Ci-C4-alkoxy and Ci-C is 4 -haloalkoxy, a radical from the series S, SO and SO2 group, R is a radical from the series hydrogen, hydroxy, in each case optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted Ci-C i-alkyl, Ci-C i-alkoxy, Ci-C 4 -alkoxy-Ci-C 4 alkyl, Ci-C4-alkyl-S-Ci-C 3 alkyl, Ci-C 4 alkyl-S (0) -C-C 3 alkyl, C 1 -C4- alkyl-S (0) 2 -C-C 3 alkyl, Ci-C4-alkylcarbonyl, Ci-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - cycloalkyl-Ci-C 3 alkyl, heterocyclyl, heterocyclyl-Ci -C 3 alkyl and in each case optionally mono- to trisubstituted by Ci-C 4 alkyl, Ci-C3 haloalkyl, Ci-C 3 alkoxy, C 3 - substituted haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or cyano, phenyl , Benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl,
R19 für Wasserstoff, für ein Alkali- oder Erdalkalimetallion, für ein gegebenfalls einfach bis vierfach durch Ci-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C2-alkyl, Ci-C4-Alkyl-S-Ci-C2-alkyl, C1-C4- Alkyl-S(0)-Ci-C2-alkyl und Ci-C4-Alkyl-S(0)2-Ci-C2-alkyl steht, oder R 19 is hydrogen, an alkali or alkaline earth metal ion, an optionally monosubstituted to fourfold substituted by Ci-C 4 alkyl ammonium ion or a each optionally mono- or polysubstituted by halogen or mono- or cyano-double-substituted radical from the series Ci- C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S-C 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S ( 0) -CC-C 2 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, or
R22 für einen der folgenden E-Reste R 22 for one of the following E radicals
_ _
E-31 E-31
E-35 E-36 E-35 E-36
E-39  E-39
E-49 E-51 steht,  E-49 E-51 stands,
R23 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6- Cycloalkyl, C3-C6-Cycloalkenyl, Ci-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6- Cycloalkyloxy, Ci-C4-Alkylthio-Ci-C4-alkyl, C2-C4-Alkenylthio-Ci-C4-alkyl, Cyano-Ci-C4-alkyl und Ci-C4-Alkoxy-Ci-C4alkyl steht, oder, wenn R2 für einen der unter f) aufgeführten Reste steht R 23 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 4 -cycloalkyl C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl and C 1 -C 4 -alkyl C4-alkoxy-Ci-C 4 alkyl, or, when R 2 is one of the radicals listed under f)
R22 und R23 auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gesättigten vier- bis sechsgliedrigen Ring bilden können, der ein weiteres Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, R 22 and R 23 may also together with the nitrogen atom to which they are attached form a saturated four- to six-membered ring which may contain another heteroatom from the series consisting of nitrogen, oxygen and sulfur,
R27 für Wasserstoff oder Ci-C4-Alkyl steht und R 27 is hydrogen or C 1 -C 4 -alkyl and
R26 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C2-C4-Alkenyl, C2- C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C2-alkyl, C1-C4- Alkylsulfanyl, Ci-C4-Halogenalkylsulfanyl, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci- C4-Alkylsulfonyl, Ci-C4-Alkylthio-Ci-C2-alkyl, Ci-C4-Alkylsulfmyl-Ci-C2-alkyl, C1-C4- Alkylsulfonyl-Ci-C2-alkyl und Cyano-Ci-C4-alkyl steht. Vorzugsbereich (3): Ganz besonders bevorzugt sind Verbindungen der Formel (I), in welchen für einen der folgenden A-Reste R 26 is a radical from the group of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - Cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 4 alkylsulfonyl, Ci-C4-alkylthio-Ci-C 2 alkyl, Ci-C 4 -Alkylsulfmyl-Ci-C 2 alkyl, C 1 -C4- alkylsulphonyl-Ci-C 2 alkyl, and cyano-Ci C4 alkyl. Preferred range (3): Very particular preference is given to compounds of the formula (I) in which one of the following A radicals
(A-b) (A-f) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,  (A-b) (A-f), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I),
B2 für Wasserstoff steht, B 2 is hydrogen,
Q für Schwefel steht, Q stands for sulfur,
R1 für Wasserstoff steht, R 1 is hydrogen,
R2 a) für einen B-Rest aus der Reihe R 2 a) for a B residue from the series
B-5) (B-9) (B- 10) B-l l)  B-5) (B-9) (B-10) B-1)
(B-27) (B-28) (B-31 ) (B-27) (B-28) (B-31)
(B-38) (B-39) (B-40) (B-41 ) (B-38) (B-39) (B-40) (B-41)
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder (B-42) (B-43) (B-44) (B- 45) wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of the formula (I), or
R2 b) für einen D-Rest aus der Reihe (D- 1 ) bis (D-3) R 2 b) for a D radical from the series (D-1) to (D-3)
(D-1 ) (D-2) (D-3) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder  (D-1) (D-2) (D-3), wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or
R2 c) für einen Rest der Formel R 2 c) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R2 d) für einen Rest der Formel wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or R 2 d) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R2 e) für einen Rest aus der Reihe (F- 1 ), (F-8) und (F- 10) in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I), or R 2 e) represents a radical from the series (F-1), (F-8) and (F-10)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder f) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder g) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, in which the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or f) a radical of the formula wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or g) a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
G2 für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Ci-C4-Alkylamino, Halogen Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, C1-C4- Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, halogeniertes Ci-C4-Alkoxy-Ci-C4- alkyl, Bis(Ci-C4-alkoxy)-Ci-C4-alkyl, Bis(halogen-Ci-C4-alkoxy)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci- C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfmyl)-Ci-C4-alkyl, Ci-C4-Alkoxy- (Ci-C4-alkylsulfonyl)-Ci-C4-alkyl, Bis(Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(halogen-Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Bis(hydroxy-Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, C(X2)NR3R4, NR6R7, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C4- Halogenalkylsulfonyl und die Heteroarylreste Pyridyl, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl steht, oder für einen der folgenden C-Reste G 2 is hydrogen or a radical selected from halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkyl, halogen -C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy alkyl, bis-C 4 -C (Ci-C 4 alkoxy) alkyl, bis-C 4 -C (halo-Ci-C4-alkoxy) alkyl, Ci-C4 alkoxy (Ci- C4 -alkylsulfanyl) -Ci-C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfmyl) -Ci-C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfonyl) - C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, bis (halogeno-C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, bis (hydroxy-C 1 -C 4 -alkyl) 4- alkylsulfanyl) -Ci-C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfinyl, Ci-C 4 - haloalkylsulphonyl, and the heteroaryl groups pyridyl, pyrimidyl, imidazolyl, pyrazolyl, Oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl, or one of the following C radicals
steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C4- Alkyl und Ci-C4-Halogenalkyl steht, für Sauerstoff steht, für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy und Trifluormethoxy steht, für Sauerstoff, Schwefel, NR5 oder NOH steht, für 2 steht, für NR18R19 oder für einen jeweils gegebenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe Ci- C4-Alkyl, C3-C4-Alkenyl, C3-C4-Alkinyl, Ci-C2-Alkoxy-Ci-C2-alkyl und Ci-C2-Alkyl-S-Ci-C2- alkyl, Ci-C2-Alkyl-S(0)-Ci-C2-alkyl, Ci-C2-Alkyl-S(0)2-Ci-C2-alkyl, für R18-CO-Ci-C2-alkyl, für NR18R19-CO-Ci-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, Ci-C2- Alkoxy oder Ci-C2-Halogenalkyl oder durch ein Sauerstoffatom (führt zu C=0) substituiertes C3- is wherein the dashed line represents the bond to the B-radicals, a radical from the series hydrogen, halogen, Ci-C 4 - alkyl and Ci-C 4 haloalkyl, represents oxygen, a radical from the series Is hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, is oxygen, sulfur, NR 5 or NOH, is 2, NR 18 R 19 or any one of them once, twice, three times, four times or five times by fluorine, chlorine or mono- or disubstituted by cyano radical from the series Ci- C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 2 -alkoxy-Ci-C 2 alkyl, and Ci-C2 alkyl-S-Ci-C 2 - alkyl, Ci-C2 alkyl-S (0) -C-C 2 -alkyl, C 2 -Alkyl-S (0) 2- Ci-C 2 -alkyl, for R 18 -CO-Ci-C 2 -alkyl, for NR 18 R 19 -CO-Ci-C 2 -alkyl, optionally optionally once or twice by Ci-C 2 alkyl, C 2 - alkoxy or Ci-C 2 haloalkyl, or by an oxygen atom (leads to C = 0) substituted C3-
C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, Ci-C2-Alkoxy oder Ci-C2-Halogenalkyl oder durch ein Sauerstoffatom (führt zu C=0) substituiertes C3-C6- Cycloalkenyl, für gegebenenfalls einfach bis zweifach durch Ci-C2-Alkyl, Ci-C2-Alkoxy oder Ci- C2-Halogenalkyl substituiertes C3-C6-Cycloalkyl-Ci-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, Ci-C2-Alkoxy oder Ci-C2-Halogenalkyl substituiertes C3-C6- Cycloalkenyl-Ci-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, C1-C2- Alkoxy oder Ci-C2-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, Ci-C2-Alkoxy oder Ci-C2-Halogenalkyl substituiertes Heterocyclyl- Ci-C2-alkyl oder für jeweils gegebenenfalls einfach oder zweifach durch Fluor, Chlor, Brom,C6-cycloalkyl, for optionally mono- or disubstituted by Ci-C 2 alkyl, Ci-C 2 -alkoxy or Ci-C 2 -haloalkyl or by an oxygen atom (leads to C = 0) substituted C3-C6-cycloalkenyl, optionally mono- or disubstituted by Ci-C 2 alkyl, Ci-C 2 alkoxy or C 2 C -halogenoalkyl-substituted C3-C6-cycloalkyl-Ci-C 2 alkyl, optionally monosubstituted or C 2 -C 6 -cycloalkenyl-C 1 -C 2 -alkyl which is monosubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl and is optionally mono- or disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 - Alkoxy or Ci-C2-haloalkyl-substituted heterocyclyl, optionally substituted once or twice by Ci-C 2 alkyl, Ci-C 2 alkoxy or Ci-C 2 -haloalkyl substituted heterocyclyl Ci-C 2 alkyl or for each optionally mono- or disubstituted by fluorine, chlorine, bromine,
Cyano, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl oder Thiazolylmethyl steht, Cyano, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl or thiazolylmethyl,
R3 für Ci-C4-Alkyl steht, R4 für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C i-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl und Ci-C4-Alkylthio-Ci-C4-alkyl steht, R 3 is C 1 -C 4 -alkyl, R 4 is a radical from the series consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C3-C6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 Alkoxycarbonyl-C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R5 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl und Ci-C4-Alkylthio-Ci-C4-alkyl steht, R 5 is a radical from the group of hydrogen, Ci-C 4 alkyl, halo-Ci-C4-alkyl, cyano-Ci-C 4 alkyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl , C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R6 für Wasserstoff oder Ci-C4-Alkyl steht, R 6 is hydrogen or C 1 -C 4 -alkyl,
R7 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, Ci-C4-Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Aryl-Ci-C4- alkyl oder Hetaryl-Ci-C4-alkyl steht oder R 7 is a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, halogen -C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-Ci- -C 4 alkyl, aryl-Ci-C 4 - alkyl is or hetaryl-Ci-C4 alkyl, or
R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann, R 6 and R 7, together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms (with oxygen and sulfur atoms not being immediately adjacent may contain)
R8 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, Cyano-Ci-C6-alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C2-C6-Alkenyl, Ci-C6-Alkoxy-Ci-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes Ci-Cö-Alkylcarbonyl und Ci-Cö-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxycarbonyl und gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkyl und Cyano substituiertes C3-C6- Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch CI-CÖ- Alkyl oder Aryl-Ci-Cö-alkyl substituiertes Ammonium-Ion steht, R 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by halogen, Ci-Cö-alkyl, Ci-C6 alkoxy, Ci-C6-haloalkyl and cyano substituted C3-C6 cycloalkylcarbonyl group, or an optionally a cation or CI-C Ö - represents alkyl or aryl-Ci-COE-alkyl-substituted ammonium ion,
9 9
R für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C4-Alkoxy, C1-C4- Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, C1-C4- Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl und Ci-C4-Halogenalkylsulfonyl substituiertes C1-C4- Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C4- Alkyl, Ci- C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C4-alkyl und C3-C4-Cycloalkenyl, in welchen ein oder zwei Ringglieder jeweils durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein können (und dabei insbesondere für R represents a radical from the series in each case optionally substituted by halogen, Ci-C4 alkoxy, C1-C4 haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4 alkylsulfinyl, C1-C4 Haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, each optionally substituted by halogen, C 1 -C 4 -alkyl, C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl in which one or two ring members are each represented by a heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
wobei der Pfeil jeweils die Bindung zum S-Atom im Rest (C-l) und im Rest (F-l) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C4-Alkyl, C1-C4- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, C1-C4- Halogenalkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl, C1-C4- Halogenalkylsulfonyl, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, C1-C4- Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, C1-C4- Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl- Ci-C4-alkyl und Heteroaryl-Ci-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und Ci-C4-Alkyl stehen, wherein the arrow in each case marks the bond to the S atom in the radical (Cl) and in the radical (F1)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylthio C 4 haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino C 4 haloalkoxy-Ci-C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-Ci-C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, Ci C4-alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-Ci-C4-alkyl and heteroaryl-Ci-C4-alkyl or NR'R ", wherein R 'and R" are independently a radical from the series of hydrogen and Ci-C4-alkyl,
R8 und R9 können im Rest (C-l) und im Rest (F-l) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, CI-CÖ- Alkyl, Ci-Cö-Halogenalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine und bevorzugt eine Carbonylgruppe enthalten kann, insbesondere können R8 und R9 zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe R 8 and R 9 in the radical (Cl) and in the radical (Fl) can also be used together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally halogen, CI-CÖ-alkyl, Ci -Cö-haloalkyl, Ci-C 6 alkoxy, Ci-C6-haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably a carbonyl group may contain, in particular R 8 and R 9 may together with the NS (0) n group to which they are attached, stand for a residue from the series
stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert), für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C i-Alkoxy, C1-C4- Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, C1-C4- Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl und Ci-C4-Halogenalkylsulfonyl substituiertes C1-C4- Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C4-alkyl, C3-C4-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N- Thiomorpholinyl, N-Thiomorpholinyl-l -oxid, N-Thiomorpholinyl-l , l -dioxid, N-Piperazinyl, N-l - Methylpiperazinyl und N-2-Oxo-l -methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Cs-Ce-Cycloalkyl, C1-C4- Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, Amino, C1-C4- Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-Ci-C4-alkyl und Heteroaryl-Ci-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und Ci- C4-Alkyl stehen, für einen Rest aus der Reihe Wasserstoff, Hydroxy, für jeweils gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituiertes Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkyl-S-Ci-C2-alkyl, Ci-C4-Alkyl-S(0)-Ci-C2-alkyl, Ci-C4-Alkyl-S(0)2-Ci-C2-alkyl, Ci-C4-Alkylcarbonyl, C1-C4- Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C3-alkyl, Heterocyclyl und Heterocyclyl-Ci-C3-alkyl und jeweils gegebenenfalls einfach bis dreifach durch Ci-C4-Alkyl, Ci- C3-Halogenalkyl, Ci-C3-Alkoxy, Ci-C3-Halogenalkoxy, Cyclopropyl, Fluor, Chlor, Brom oder Cyano substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl und Thiazolylmethyl steht, für Wasserstoff, ein Alkali- oder Erdalkalimetallion, für ein gegebenfalls einfach bis vierfach durch Ci-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C2-alkyl und Ci-C4-Alkyl-S-Ci-C2-alkyl, Ci-C4-Alkyl-S(0)-Ci-C2-alkyl und Ci-C4-Alkyl-S(0)2-Ci-C2- alkyl steht, für einen Rest aus der Reihe S, SO und S02 steht, für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy und Trifluormethoxy steht, für einen Rest aus der Reihe Methyl, Ethyl, Isopropyl, n-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2,2-Difluor-n-propyl, Methylsulfanyl-methyl, Methylsulfanylethyl, Methylsulfanyl-n-propyl, Trifluormethylsulfonylmethyl, (in which the arrow in each case marks the bond to the C (X) group), a radical from the row in each case optionally substituted by halogen, C 1 -C -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C4 haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl-substituted C 1 -C 4 - alkyl, C 2 -C 4 alkenyl and C 2 -C 4 alkynyl, in each case optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C3-C4-cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-l-oxide, N-thiomorpholinyl-l, l-dioxide, N-piperazinyl, Nl - methylpiperazinyl and N-2-oxo-l-methylpiperazinyl, each optionally substituted by halogen, cyano (also in the alkyl portion), nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C i -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkyl ulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkyl sulfonyl, alkoxycarbonylamino, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 - C6 -Cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or for NR 'R' is where R 'and R''independently of one another represent a radical from the series consisting of hydrogen and C 1 -C 4 -alkyl, a radical from the series consisting of hydrogen, hydroxy, in each case optionally mono-, di-, tri-quadruple or five-fold by fluorine, chlorine or mono- or disubstituted by cyano-substituted Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkyl-S-Ci -C 2 -alkyl, C 1 -C 4 -alkyl-S (O) -CC-C 2 -alkyl, C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, C 1 -C 4 - Alkylcarbonyl, C C 1 -C 4 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkyl, heterocyclyl and heterocyclyl-C 1 -C 3 -alkyl and in each case optionally monosubstituted to trisubstituted by C 1 -C 4 -alkyl, C 1 -C 3 -Haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or cyano-substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl stands for hydrogen , an alkali or alkaline earth metal ion, for an optionally mono- to quadruply substituted by Ci-C 4 alkyl substituted ammonium ion or each optionally optionally mono-, di-, tri-, tetra- or quintuply fluorine, chlorine or mono- or di-cyano-substituted radical of the Series C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl and C 1 -C 4 -alkyl-S-C 1 -C 2 -alkyl, C 1 -C 4 - Alkyl-S (O) -Ci-C 2 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, a radical from the series S, SO and S0 2 , is a radical from the series of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, a radical from the series methyl, ethyl, isopropyl, n-propyl, n-butyl iso-butyl, sec-butyl, tert -butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2,2-difluoro-n-propyl, methylsulfanylmethyl, methylsulfanylethyl, methylsulfanyl-n-propyl, trifluoromethylsulfonylmethyl .
Ethylsulfonylmethyl, 2,2,2-Trifluorethylsulfonylmethyl, 2,2-Difluorethylsulfonylmethyl, Isopropylsulfanylmethyl, Methylsulfinylmethyl, Trifluormethylsulfinylmethyl, Ethylsulfinyl- methyl, 2,2,2-Trifluorethylsulfinylmethyl, 2,2-Difluorethylsulfinylmethyl, Isopropyl- sulfinylmethyl, Methylsulfonylmethyl, Trifluormethylsulfonylmethyl, Ethylsulfonylmethyl, 2,2,2- Trifluorethylsulfonylmethyl, 2,2-Difluorethylsulfonylmethyl, Isopropylsulfonylmethyl, Methoxycarbonyl, Ethoxycarbonyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, Dimethylaminocarbonyl, Diethylaminocarbonyl, N- Ethyl-N-methylaminocarbonyl, N-Isopropyl-N-methylaminocarbonyl, Dimethylamino- carbonylmethyl, Diethylaminocarbonylmethyl, N-Ethyl-N-methylaminocarbonylmethyl, N- Isopropyl-N-methylaminocarbonylmethyl, Dimethylaminocarbonylethyl, Diethylamino- carbonylethyl, N-Ethyl-N-methylaminocarbonylethyl, N-Isopropyl-N-methylaminocarbonylethyl, N-Cyclopropyl-N-methylaminocarbonylmethyl, N-Cyclopropyl-N-methylaminocarbonylethyl, Methylsulfanyl, Trifluormethylsulfanyl, Ethylsulfanyl, 2,2,2-Trifluorethylsulfanyl, 2,2- Difluorethylsulfanyl, Isopropylsulfanyl, Methylsulfinyl, Trifluormethylsulfinyl, Ethylsulfinyl, 2,2,2-Trifluorethylsulfinyl, 2,2-Difluorethylsulfinyl, Isopropylsulfinyl, Methylsulfonyl, Trifluormethylsulfonyl, Ethylsulfonyl, 2,2,2-Trifluorethylsulfonyl, 2,2-Difluorethylsulfonyl, Isopropylsulfonyl, Cyclopropyl, 1 -Cyanocyclopropyl, 1 -Chlorcyclopropyl, 1 -Fluorcyclopropyl, 2- Cyanocyclopropyl, 2-Chlorcyclopropyl, 2-Fluorcyclopropyl, 2,2,3, 3-Tetrafluorcyclopropyl, 2- Cyclopropylcyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 4-Trifluormethylcyclohexyl, Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl N-Cyclopropyl-N-methylaminocarbonyl Morpholin-4-ylcarbonylmethyl, Piperazin- 1 -ylcarbonylmethyl, 4-Methyl-piperazin- 1 - ylcarbonylmethyl, jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Heterocyclylmethyl und Heterocyclylethyl, jeweils durch Cyclopropyl substituiertes Heterocyclylmethyl und Heterocyclylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Aryl, durch Cyclopropyl substituiertes Aryl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Arylmethyl und Arylethyl, durch Cyclopropyl substituiertes Arylmethyl und Arylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Hetarylmethyl und Hetarylethyl, durch Cyclopropyl substituiertes Hetarylmethyl und Hetarylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, steht, oder für einen D-Rest aus der Reihe (D-l) bis (D-3) Ethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2,2-difluoroethylsulfonylmethyl, isopropylsulfanylmethyl, methylsulfinylmethyl, trifluoromethylsulfinylmethyl, ethylsulfinylmethyl, 2,2,2-trifluoroethylsulfinylmethyl, 2,2-difluoroethylsulfinylmethyl, isopropylsulfinylmethyl, methylsulfonylmethyl, trifluoromethylsulfonylmethyl, ethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2,2-difluoroethylsulfonylmethyl, isopropylsulfonylmethyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, dimethylaminocarbonyl, diethylaminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-isopropyl-N-methylaminocarbonyl, dimethylamino carbonylmethyl, diethylaminocarbonylmethyl, N-ethyl-N-methylaminocarbonylmethyl, N-isopropyl-N-methylaminocarbonylmethyl, dimethylaminocarbonylethyl, diethylaminocarbonylethyl, N-ethyl-N-methylaminocarbonylethyl, N-isopropyl-N-methylaminocarbonylethyl, N-cyclopropyl-N-methylaminocarbonylmethyl, N-Cyc lopropyl-N-methylaminocarbonylethyl, methylsulfanyl, trifluoromethylsulfanyl, ethylsulfanyl, 2,2,2-trifluoroethylsulfanyl, 2,2-difluoroethylsulfanyl, isopropylsulfanyl, methylsulfinyl, trifluoromethylsulfinyl, ethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, isopropylsulfinyl, Methylsulfonyl, trifluoromethylsulfonyl, ethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2,2-difluoroethylsulfonyl, isopropylsulfonyl, cyclopropyl, 1-cyano-cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 2-cyanocyclopropyl, 2-chlorocyclopropyl, 2-fluorocyclopropyl, 2, 2,3, 3-tetrafluorocyclopropyl, 2-cyclopropylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-trifluoromethylcyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, N-cyclopropyl-N-methylaminocarbonyl, morpholin-4-ylcarbonylmethyl, piperazine-1-ylcarbonylmethyl, 4-methyl- piperazin-1-ylcarbonylmethyl, in each case optionally mono-, di- or trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, Hydroxyl, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy-substituted heterocyclylmethyl and heterocyclylethyl, in each case cyclopropyl-substituted heterocyclylmethyl and heterocyclylethyl, where the cyclopropyl radical is optionally mono- or disubstituted by methyl, fluorine, chlorine, Cyano or is simply substituted by cyclopropyl, optionally mono-, di- or trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy Substituted difluoromethoxy, aryl substituted by cyclopropyl, wherein the cyclopropyl optionally substituted once or twice by methyl, fluorine, chlorine, cyano or simply by cyclopropyl, respectively optionally mono-, di- or trisubstituted, identically or differently, arylmethyl and arylethyl substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy Cyclopropyl-substituted arylmethyl and arylethyl, where the cyclopropyl radical is optionally monosubstituted or disubstituted by methyl, fluorine, chlorine, cyano or simply by cyclopropyl, in each case optionally monosubstituted or disubstituted by identical or different substituents, by fluorine, chlorine, bromine, cyano, nitro, hydroxy, Amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy-substituted hetarylmethyl and hetarylethyl, cyclopropyl-substituted hetarylmethyl and hetarylethyl, where the cyclopropyl optionally mono- or disubstituted by methyl, fluorine, chlorine, cyano or simply is substituted by cyclopropyl, stands for one or D radical from the series (D1) to (D-3)
(D-1 ) (D-2) (D-3) oder einen der folgenden E-Reste  (D-1) (D-2) (D-3) or one of the following E radicals
E-1 E-2 E-3 E-4  E-1 E-2 E-3 E-4
E-10 E-11 E-10 E-11
E-31 E-31
E-35 E-36 E-35 E-36
E-39  E-39
E-49 E-51 steht, oder, im Fall R = d), auch für den E-Rest (E-13)  E-49 E-51 stands, or, in the case R = d), also for the E-residue (E-13)
E-1 3 steht, steht für einen Rest aus der Reihe Wasserstoff, Ci-C6-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C6-Cycloalkyl, C3-C6-Cycloalkenyl, Ci-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6- Cycloalkyloxy, Ci-C4-Alkylthio-Ci-C4-alkyl, C2-C4-Alkenylthio-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl steht, oder, für R = c) oder f), R und R auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für Pyrrolidinyl, Piperidinyl, Morpholinyl, Thiomorpholinyl, Thiomorpholinyl-l-oxid, Thiomorpholinyl-1,1- dioxid, Piperazinyl, 1 -Methylpiperazinyl oder 2-Oxo-l-methylpiperazinyl stehen können, E-1 3, is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy , C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl , C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or, for R = c) or f), R and R also together with the nitrogen atom to which they are bonded, for pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl-l-oxide, thiomorpholinyl-1,1-dioxide, piperazinyl, 1-methylpiperazinyl or 2-oxo-l methylpiperazinyl can stand,
R27 für Wasserstoff oder Methyl steht und R26 für einen Rest aus der Reihe Wasserstoff, Methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, Propenyl, Propargyl, Cyclopropyl, Cyclopropylmethyl, Methoxymethyl, Methylsulfanyl, Trifluormethylsulfanyl, Ethylsulfanyl, Trifluorethylsulfanyl, Methylsulfinyl,R 27 is hydrogen or methyl and R 26 is a radical from the group consisting of hydrogen, methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl, propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl, methylsulfanyl, trifluoromethylsulfanyl, ethylsulfanyl, Trifluoroethylsulfanyl, methylsulfinyl,
Trifluormethylsulfinyl, Ethylsulfinyl, Trifluorethylsulfinyl, Methylthioethyl, Methylsulfinylethyl, Methylsulfonylethyl oder Cyanomethyl steht und Verbindungen der Formel (I), in welchen Trifluoromethylsulfinyl, ethylsulfinyl, trifluoroethylsulfinyl, methylthioethyl, methylsulfinylethyl, methylsulfonylethyl or cyanomethyl and compounds of the formula (I) in which
A für den A-Rest A for the A-remainder
(A-a) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,  (A-a), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I),
G1 für N oder C-B1 steht, G 1 is N or CB 1 ,
B1 für einen Rest aus der Reihe Wasserstoff und Fluor steht, B 1 is a radical from the series hydrogen and fluorine,
B2 für Wasserstoff steht, B 2 is hydrogen,
T für Sauerstoff oder ein Elektronenpaar steht, Q für Schwefel steht, T is oxygen or an electron pair, Q is sulfur,
R1 für Wasserstoff steht, R 1 is hydrogen,
R2 a) für einen B-Rest aus der Reihe R 2 a) for a B residue from the series
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Ci-C4-Alkylamino, Halogen Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, C1-C4- Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, halogeniertes Ci-C4-Alkoxy-Ci-C4- alkyl, Bis(Ci-C4-alkoxy)-Ci-C4-alkyl, Bis(halogen-Ci-C4-alkoxy)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci- C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfmyl)-Ci-C4-alkyl, Ci-C4-Alkoxy- (Ci-C4-alkylsulfonyl)-Ci-C4-alkyl, Bis(Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(halogen-Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Bis(hydroxy-Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, C(X2)NR3R4, NR6R7, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl und die Heteroarylreste Pyridyl, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl steht, oder i) für einen der folgenden B-Reste (B-42) (B-43) (B-44) (B- 45), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I) wherein, for hydrogen or a halogen radical, Nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy , C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl , Bis (halogeno-C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy (C 1 -C 4 -alkylsulfmyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfonyl) C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkylsulfanyl) ci C 4 alkyl, bis (halo-Ci-C 4 - alkylsulfanyl) -C-C4-alkyl, bis (hydroxy-Ci-C4-alkylsulfanyl) -C-C4-alkyl, Ci-C4-alkoxycarbonyl, Ci-C 4 Alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl and the heteroaryl radicals pyridyl, pyrimidyl , Imidaz olyl, pyrazolyl, oxazolyl, Thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl, or i) one of the following B radicals
(B-l)  (B-l)
(B-2) (B-3) (B-4)  (B-2) (B-3) (B-4)
(B-21) (B-23) (B-25) (B-21) (B-23) (B-25)
(B-27) (B-28) (B-27) (B-28)
wonn  Wonn
G2 für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Ci-C i-Alkylamino, Halogen C1-C4- Alkylamino, Di-(Ci-C4-alkyl)-amino, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, halogeniertes Ci-C4-Alkoxy-Ci-C4-alkyl, Bis(Ci-C4-alkoxy)-Ci-C4-alkyl, Bis(halogen-Ci-C4- alkoxy)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4- alkylsulfmyl)-Ci-C4-alkyl, Ci-C4-Alkoxy-(Ci-C4-alkylsulfonyl)-Ci-C4-alkyl, Bis(Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Bis(halogen-Ci-C4-alkylsulfanyl)-Ci-C4-alkyl, Bis(hydroxy-Ci-C4- alkylsulfanyl)-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, C(X2)NR3R4, NR6R7, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, C1-C4- Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl und die Heteroarylreste Imidazolyl, Pyrazolyl, Oxazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl steht, oder „ Λ G 2 is a radical from the group consisting of halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, halogeno C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, bis (halogen-C 1 -C 4 -alkoxy) -C-C 4 alkyl, Ci-C4-alkoxy- (Ci-C4-alkylsulfanyl) -C-C 4 alkyl, Ci-C4-alkoxy- (Ci-C 4 - alkylsulfmyl) -C-C 4 alkyl, C 1 -C 4 alkoxy- (C 1 -C 4 alkylsulfonyl) C 1 -C 4 alkyl, bis (C 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, bis (haloC 1 -C 4 -alkylsulfanyl ) C 1 -C 4 -alkyl, bis (hydroxy-C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl and the heteroaryl radicals imidazolyl , Pyrazolyl, oxazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl, o of the " Λ
- 104 - wenn R2 für einen der unter a) oder aa) aufgeführten Reste steht G2 auch für einen der folgenden C-Reste When R 2 is one of the radicals listed under a) or aa), G 2 is also one of the following C radicals
steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, R2 c) für einen Rest der Formel wherein the dashed line is the bond to the B radicals, R 2 c) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder d) für einen Rest der Formel  wherein the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or d) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder e) für einen Rest aus der Reihe (F-8) und (F-10) in which the dashed line denotes the bond to the carbon atom of the bicycle of the formula (I), or e) a radical from the series (F-8) and (F-10)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder f) für einen Rest der Formel 22 in which the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or f) a radical of the formula 22
- R  - R
ΊΜ' ΊΜ '
I 9Q  I 9Q
R steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder  R is where the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I), or
X für Sauerstoff steht, X2 für Sauerstoff, Schwefel, NOH steht, n für 2 steht, X is oxygen, X 2 is oxygen, sulfur, NOH, n is 2,
R3 für Ci-C4-Alkyl steht, R 3 is C 1 -C 4 -alkyl,
R4 für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C i-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl und Ci-C4-Alkylthio-Ci-C4-alkyl steht, R 4 is a radical selected from the group consisting of hydrogen, C 1 -C -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl , C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R5 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci- C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl und Ci-C4-Alkylthio-Ci-C4-alkyl steht, R 5 is a radical from the group of hydrogen, Ci-C 4 alkyl, halo-Ci-C4-alkyl, cyano-Ci-C 4 alkyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl , C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C 4 alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R6 für Wasserstoff oder Ci-C4-Alkyl steht, R7 für einen Rest aus der Reihe Wasserstoff, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, C2-C4-Alkinyl, Ci-C4-Alkoxy, Halogen-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Aryl-Ci-C4- alkyl oder Hetaryl-Ci-C4-alkyl steht oder R 6 is hydrogen or C 1 -C 4 -alkyl, R 7 is a radical from the series consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkyl, C 4 -alkynyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkoxy C 4 alkyl, Ci-C4-alkylthio-Ci-C 4 alkyl, aryl-Ci-C 4 - alkyl is or hetaryl-Ci-C4 alkyl, or
R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und SchwefelR 6 and R 7, together with the nitrogen atom to which they are attached, form a 4- to 7-membered ring containing one or two further nitrogen, oxygen and sulfur heteroatoms
(wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann, (where oxygen and sulfur atoms are not allowed to be immediately adjacent) may contain
R8 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, Cyano-Ci-C6-alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C2-C6-Alkenyl, Ci-C6-Alkoxy-Ci-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes Ci-Cö-Alkylcarbonyl und Ci-Cö-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Ci-C6-Alkoxycarbonyl und gegebenenfalls durchR 8 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, ci C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-Cö-alkylcarbonyl and Ci-Cö-alkylsulfonyl, optionally substituted by halogen Ci-C6-alkoxycarbonyl and optionally by
Halogen, Ci-Cö-Alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkyl und Cyano substituiertes C3-C6- Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch Ci-Cö-Alkyl oder Aryl-Ci-Cö-alkyl substituiertes Ammonium-Ion steht, 1 ^ Halogen, Ci-Cö-alkyl, Ci-C6-Alkoxy, Ci-C6-haloalkyl and Cyano substituted C3-C6-Cycloalkylcarbonyl stands, or for a cation or an optionally by Ci-Cö-alkyl or Aryl-Ci-Cö-alkyl substituted ammonium ion is, 1 ^
- 106 - für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C i-Alkoxy, C1-C4- Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, C1-C4- Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl und Ci-C4-Halogenalkylsulfonyl substituiertes C1-C4- Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C4-alkyl und C3-C4-Cycloalkenyl, in welchen ein oder zwei Ringglieder jeweils durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein können (und dabei insbesondere für - 106 - is a radical from the series in each case optionally substituted by halogen, Ci-C i-alkoxy, C1-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl , C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, each optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, Haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl, in which one or two ring members in each case by a heteroatom from the Sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
wobei der Pfeil jeweils die Bindung zum S-Atom im Rest (C-l) und im Rest (F-l) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C4-Alkyl, C1-C4- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, C1-C4- Halogenalkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl, C1-C4- Halogenalkylsulfonyl, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, C1-C4- Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, C1-C4- Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl- Ci-C4-alkyl und Heteroaryl-Ci-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und Ci-C4-Alkyl stehen, für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, Ci-C4-Alkoxy, C1-C4- Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, C1-C4- Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl und Ci-C4-Halogenalkylsulfonyl substituiertes C1-C4- Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C4-alkyl, C3-C4-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N- Thiomorpholinyl, N-Thiomorpholinyl-l -oxid, N-Thiomorpholinyl-l , l -dioxid, N-Piperazinyl, N-l - Methylpiperazinyl und N-2-Oxo-l -methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Cs-Cö-Cycloalkyl, C1-C4- Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, Amino, C1-C4- Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-Ci-C4-alkyl und Heteroaryl-Ci-C i-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und Ci- C i-Alkyl stehen, für einen Rest aus der Reihe Wasserstoff, Hydroxy, für jeweils gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituiertes Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkyl-S-Ci-C2-alkyl, Ci-C4-Alkyl-S(0)-Ci-C2-alkyl, Ci-C4-Alkyl-S(0)2-Ci-C2-alkyl, Ci-C4-Alkylcarbonyl, C1-C4- Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C3-alkyl, Heterocyclyl und Heterocyclyl-Ci-C3-alkyl und jeweils gegebenenfalls einfach bis dreifach durch Ci-C4-Alkyl, Ci- C3-Halogenalkyl, Ci-C3-Alkoxy, Ci-C3-Halogenalkoxy, Cyclopropyl, Fluor, Chlor, Brom oder Cyano substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl und Thiazolylmethyl steht, für Wasserstoff, ein Alkali- oder Erdalkalimetallion, für ein gegebenfalls einfach bis vierfach durch Ci-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C2-alkyl und Ci-C4-Alkyl-S-Ci-C2-alkyl, Ci-C4-Alkyl-S(0)-Ci-C2-alkyl und Ci-C4-Alkyl-S(0)2-Ci-C2- alkyl steht, und im Fall, dass R2 für einen der unter f) aufgeführten Reste steht für einen Rest aus der Reihe Methyl, Ethyl, Isopropyl, n-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert- Butyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2,2-Difluor-n-propyl, Methylsulfanyl-methyl, Methylsulfanylethyl, Methylsulfanyl-n-propyl, Trifluormethylsulfonylmethyl, wherein the arrow in each case marks the bond to the S atom in the radical (Cl) and in the radical (F1)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylthio C 4 haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino C 4 haloalkoxy-Ci-C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-Ci-C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, Ci C4-alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-Ci-C4-alkyl and heteroaryl-Ci-C4-alkyl or NR'R ", wherein R 'and R" are independently a radical from the series of hydrogen and Ci-C4-alkyl, a radical from the series in each case optionally substituted by halogen, Ci-C4-alkoxy, C1-C4-haloalkoxy , C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -halogenoalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, in each case optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C4 -alkyl, C3-C4-cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-l-oxide, N-thiomorpholinyl-l, l-dioxide, N-piperazinyl, Nl - methylpiperazinyl and N-2-oxo-l-methylpiperazinyl, in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di - (Ci-C4-alkyl) -amino, Ci-C4-Alkylcarbonylamino, Ci-C4-Alkoxycarbonylamino, Ci -C 4 alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 - C 6 cycloalkyl C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or represents NR'R ", in which R 'and R" independently of one another represent a radical from the series consisting of hydrogen and C 1 -C 4 -alkyl. Alkyl, a radical selected from the group consisting of hydrogen, hydroxyl, in each case optionally mono-, di-, tri-, tetra- or quintuple by fluorine, chlorine or mono- or di-cyano-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-S-C 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S (0) -CC-C 2 -alkyl, C 1 -C 4 -alkyl -C 4 alkyl-S (0) 2 -C-C 2 alkyl, Ci-C 4 alkylcarbonyl, C 1 -C4- alkoxycarbonyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C3-alkyl , Heterocyclyl and heterocyclyl-C 1 -C 3 -alkyl and in each case optionally mono- to trisubstituted by C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or Cyano substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl, for hydrogen, is an alkali or alkaline earth metal ion, an optionally monosubstituted to cis-C 4 alkyl-substituted ammonium ion, or each optionally optionally mono-, di-, tri-, tetra- or quintuple fluoro, chloro, or mono- or di-cyano substituted by cyano radical from the series Ci-C 4 alkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 2 -alkyl and Ci-C 4 -alkyl-S-Ci-C 2 -alkyl , Ci-C 4 -alkyl-S (0) -Ci-C 2 -alkyl and Ci-C 4 -alkyl-S (0) 2 -Ci-C 2 - alkyl, and in the case that R 2 is a the radicals listed under f) is a radical from the series methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2,2,2-trifluoroethyl, 2,2 -Difluoroethyl, 2,2-difluoro-n-propyl, methylsulfanylmethyl, methylsulfanylethyl, methylsulfanyl-n-propyl, trifluoromethylsulfonylmethyl,
Ethylsulfonylmethyl, 2,2,2-Trifluorethylsulfonylmethyl, 2,2-Difluorethylsulfonylmethyl, Isopropylsulfanylmethyl, Methylsulfinylmethyl, Trifluormethylsulfinylmethyl, Ethylsulfinyl- methyl, 2,2,2-Trifluorethylsulfinylmethyl, 2,2-Difluorethylsulfinylmethyl, Isopropyl- sulfinylmethyl, Methylsulfonylmethyl, Trifluormethylsulfonylmethyl, Ethylsulfonylmethyl, 2,2,2- Trifluorethylsulfonylmethyl, 2,2-Difluorethylsulfonylmethyl, Isopropylsulfonylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, Dimethylamino-carbonylmethyl, Diethylaminocarbonylmethyl, N-Ethyl-N- methylaminocarbonylmethyl, N-Isopropyl-N-methylaminocarbonylmethyl, Dimethylaminocarbonylethyl, Diethylamino-carbonylethyl, N-Ethyl-N- methylaminocarbonylethyl, N-Isopropyl-N-methylaminocarbonylethyl, N-Cyclopropyl-N- methylaminocarbonylmethyl, N-Cyclopropyl-N-methylaminocarbonylethyl, Methylsulfanyl, Trifluormethylsulfanyl, Ethylsulfanyl, 2,2,2-Trifluorethylsulfanyl, 2,2-Difluorethylsulfanyl, Isopropylsulfanyl, Methylsulfinyl, Trifluormethylsulfinyl, Ethylsulfinyl, 2,2,2- Trifluorethylsulfinyl, 2,2-Difluorethylsulfinyl, Isopropylsulfinyl, Methylsulfonyl, Trifluormethylsulfonyl, Ethylsulfonyl, 2,2,2-Trifluorethylsulfonyl, 2,2-Difluorethylsulfonyl, Isopropylsulfonyl, Cyclopropyl, 1 -Cyanocyclopropyl, 1 -Chlorcyclopropyl, 1 -Fluorcyclopropyl, 2- Cyanocyclopropyl, 2-Chlorcyclopropyl, 2-Fluorcyclopropyl, 2,2,3, 3-Tetrafluorcyclopropyl, 2- Cyclopropylcyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 4-Trifluormethylcyclohexyl, Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Morpholin-4-ylcarbonylmethyl, Piperazin- 1 -ylcarbonylmethyl, 4-Methyl-piperazin- 1 -ylcarbonylmethyl, j eweils Ethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2,2-difluoroethylsulfonylmethyl, isopropylsulfanylmethyl, methylsulfinylmethyl, trifluoromethylsulfinylmethyl, ethylsulfinylmethyl, 2,2,2-trifluoroethylsulfinylmethyl, 2,2-difluoroethylsulfinylmethyl, isopropylsulfinylmethyl, methylsulfonylmethyl, trifluoromethylsulfonylmethyl, ethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2,2-difluoroethylsulfonylmethyl, isopropylsulfonylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, dimethylamino-carbonylmethyl, diethylaminocarbonylmethyl, N-ethyl-N-methylaminocarbonylmethyl, N-isopropyl-N-methylaminocarbonylmethyl, dimethylaminocarbonylethyl, diethylamino carbonylethyl, N-ethyl-N-methylaminocarbonylethyl, N-isopropyl-N-methylaminocarbonylethyl, N-cyclopropyl-N-methylaminocarbonylmethyl, N-cyclopropyl-N-methylaminocarbonylethyl, methylsulfanyl, Trifluoromethylsulfanyl, ethylsulfanyl, 2,2,2-trifluoroethylsulfanyl, 2,2-difluoroethylsulfanyl, isopropylsulfanyl, methylsulfinyl, trifluoromethylsulfinyl, ethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, isopropylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl, ethylsulfonyl, 2, 2,2-trifluoroethylsulfonyl, 2,2-difluoroethylsulfonyl, isopropylsulfonyl, cyclopropyl, 1-cyano-cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 2-cyano-cyclopropyl, 2-chlorocyclopropyl, 2-fluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 2-cyclopropylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-trifluoromethylcyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, morpholin-4-ylcarbonylmethyl, piperazine-1-ylcarbonylmethyl, 4-methyl-piperazine-1-ylcarbonylmethyl, in each case
gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Heterocyclylmethyl und Heterocyclylethyl, jeweils durch Cyclopropyl substituiertes Heterocyclylmethyl und Heterocyclylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Aryl, durch Cyclopropyl substituiertes Aryl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Arylmethyl und Arylethyl, durch Cyclopropyl substituiertes Arylmethyl und Arylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Hetarylmethyl und Hetarylethyl, durch Cyclopropyl substituiertes Hetarylmethyl und Hetarylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, steht, und im Fall, dass R2 für einen der unter c), d) oder f) aufgeführten Reste steht auch für einen D-Rest aus der Reihe (D-l) bis (D-3) optionally mono-, di- or trisubstituted, identically or differently, heterocyclylmethyl and heterocyclylethyl substituted by fluoro, chloro, bromo, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, respectively Cyclopropyl-substituted heterocyclylmethyl and heterocyclylethyl, where the cyclopropyl radical is optionally monosubstituted or disubstituted by methyl, fluorine, chlorine, cyano or simply by cyclopropyl, optionally monosubstituted, disubstituted or trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, Hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy-substituted aryl, cyclopropyl-substituted aryl, where the cyclopropyl optionally mono- or di-methyl, fluorine, chlorine, cyano or simply by cyclopropyl is substituted, if appropriate simply, two or three times, identically or differently, arylmethyl and arylethyl substituted by fluoro, chloro, bromo, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, arylethyl, cyclopropyl-substituted arylmethyl and arylethyl, wherein the cyclopropyl radical is optionally monosubstituted or disubstituted by methyl, fluorine, chlorine, cyano or simply by cyclopropyl, each optionally mono- or disubstituted by identical or different fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl , Ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy-substituted hetarylmethyl and hetarylethyl, cyclopropyl-substituted hetarylmethyl and hetarylethyl, where the cyclopropyl optionally monosubstituted or disubstituted by methyl, fluorine, chlorine, cyano or simply substituted by cyclopropyl is, stands, and in the case that R 2 for one of the un ter c), d) or f) radicals also stands for a D radical from the series (D1) to (D-3)
(D-1 ) (D-2) (D-3) steht, worin  (D-1) (D-2) (D-3) wherein
R für NR R oder für einen jeweils gegebenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe Ci- C4-Alkyl, C3-C4-Alkenyl, C3-C4-Alkinyl, Ci-C2-Alkoxy-Ci-C2-alkyl und Ci-C2-Alkyl-S-Ci-C2- alkyl, Ci-C2-Alkyl-S(0)-Ci-C2-alkyl, Ci-C2-Alkyl-S(0)2-Ci-C2-alkyl, für R18-CO-Ci-C2-alkyl, für NR18R19-CO-Ci-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, Ci-C2- Alkoxy oder Ci-C2-Halogenalkyl oder durch ein Sauerstoffatom (führt zu C=0) substituiertes C3- C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, Ci-C2-Alkoxy oder Ci-C2-Halogenalkyl oder durch ein Sauerstoffatom (führt zu C=0) substituiertes C3-C6- Cycloalkenyl, für gegebenenfalls einfach bis zweifach durch Ci-C2-Alkyl, Ci-C2-Alkoxy oder Ci- C2-Halogenalkyl substituiertes C3-C6-Cycloalkyl-Ci-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, Ci-C2-Alkoxy oder Ci-C2-Halogenalkyl substituiertes C3-C6- Cycloalkenyl-Ci-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, C1-C2- Alkoxy oder Ci-C2-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Ci-C2-Alkyl, Ci-C2-Alkoxy oder Ci-C2-Halogenalkyl substituiertes Heterocyclyl- Ci-C2-alkyl oder für jeweils gegebenenfalls einfach oder zweifach durch Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl oder Thiazolylmethyl steht, R is NR R, or for an in each case optionally monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted by fluorine, chlorine or mono- or disubstituted by cyano radical from the series Ci- C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, Ci-C 2 alkoxy-Ci-C 2 alkyl, and Ci-C2 alkyl-S-Ci-C 2 - alkyl, Ci-C2 alkyl-S (0) -ci- C 2 -alkyl, C 1 -C 2 -alkyl-S (0) 2 -C 1 -C 2 -alkyl, for R 18 -CO-C 1 -C 2 -alkyl, for NR 18 R 19 -CO-C 1 -C 2 alkyl, optionally mono- or disubstituted by Ci-C 2 alkyl, C 2 - alkoxy or Ci-C 2 haloalkyl, or by an oxygen atom (resulting in C = 0) substituted C3-C6-cycloalkyl, optionally mono- or disubstituted by Ci-C 2 alkyl, Ci-C 2 alkoxy or C 2 -haloalkyl, or by an oxygen atom (resulting in C = 0) substituted C3-C6 cycloalkenyl, which is optionally mono- or disubstituted by Ci-C 2 -alkyl, Ci-C 2 alkoxy or C 2 C -halogenoalkyl-substituted C3-C6-cycloalkyl-Ci-C 2 alkyl, optionally mono- od he disubstituted by Ci-C 2 alkyl, Ci-C 2 alkoxy or C 2 -halogenoalkyl-substituted C3-C6-cycloalkenyl-Ci-C 2 alkyl, mono- or di-optionally substituted by Ci-C 2 alkyl, C 1 -C 2 - alkoxy or Ci-C 2 haloalkyl substituted heterocyclyl, mono- or di-optionally substituted by Ci-C 2 alkyl, Ci-C 2 alkoxy or C 2 -haloalkyl substituted heterocyclyl Ci-C 2 or phenyl optionally substituted once or twice by fluorine, chlorine, bromine, cyano, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, Furanyl, pyridinylmethyl or thiazolylmethyl,
X1 für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy und Trifluormethoxy steht, X 1 is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
W für einen Rest aus der Reihe S, SO und S02 steht, W is a radical from the series S, SO and S0 2 ,
Y3 für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy und Trifluormethoxy steht, oder Y 3 is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, or
R für einen der folgenden E-Reste R for one of the following E radicals
E-23 E-25 E-23 E-25
E-49 E-51 stellt, E-49 E-51 provides,
R23 für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6- Cycloalkyl, C3-C6-Cycloalkenyl, Ci-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6- Cycloalkyloxy, Ci-C4-Alkylthio-Ci-C4-alkyl, C2-C4-Alkenylthio-Ci-C4-alkyl, Cyano-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl steht, oder, wenn R2 für einen der unter f) aufgeführten Reste steht R 23 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkoxy Alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 1 -C 4 Alkoxy-Ci-C 4 -alkyl, or, if R 2 is one of the radicals listed under f)
R22 und R23 auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für Pyrrolidinyl, Piperidinyl, Morpholinyl, Thiomorpholinyl, Thiomorpholinyl-l-oxid, Thiomorpholinyl-1,1- dioxid, Piperazinyl, 1 -Methylpiperazinyl oder 2-Oxo-l-methylpiperazinyl stehen können, R27 für Wasserstoff oder Methyl steht und R 22 and R 23 are also taken together with the nitrogen atom to which they are attached, for pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl-1-oxide, thiomorpholinyl-1,1-dioxide, piperazinyl, 1-methylpiperazinyl or 2-oxo l-methylpiperazinyl, R 27 is hydrogen or methyl and
R26 für einen Rest aus der Reihe Wasserstoff, Methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, Propenyl, Propargyl, Cyclopropyl, Cyclopropylmethyl, Methoxymethyl, Methylsulfanyl, Trifluormethylsulfanyl, Ethylsulfanyl, Trifluorethylsulfanyl, Methylsulfinyl,R 26 is a radical from the group consisting of hydrogen, methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl, propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl, methylsulfanyl, trifluoromethylsulfanyl, ethylsulfanyl, trifluoroethylsulfanyl, methylsulfinyl,
Trifluormethylsulfinyl, Ethylsulfinyl, Trifluorethylsulfinyl Methylthioethyl, Methylsulfinylethyl, Methylsulfonylethyl oder Cyanomethyl steht. Trifluoromethylsulfinyl, ethylsulfinyl, trifluoroethylsulfinyl, methylthioethyl, methylsulfinylethyl, methylsulfonylethyl or cyanomethyl.
Vorzugsbereich (4): Eine hevorgehobene Gruppe von Verbindungen der Formel (I) sind solche, in welchen Preferred Range (4): A preferred group of compounds of the formula (I) are those in which
A für A for
(A-a) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,  (A-a), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I),
G1 für C-B1 steht, G 1 stands for CB 1 ,
B1 für Wasserstoff oder Fluor steht, B2 für Wasserstoff steht, B 1 is hydrogen or fluorine, B 2 is hydrogen,
T für ein Elektronenpaar steht, Q für Schwefel steht, T stands for a pair of electrons, Q stands for sulfur,
R1 für Wasserstoff steht, R 1 is hydrogen,
R2 a) für einen B-Rest aus der Reihe R 2 a) for a B residue from the series
(B-l)  (B-l)
(B-2)  (B-2)
(B-10)  (B-10)
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder (B-42) (B-43) (B-44) (B-45), wherein the broken line represents the bond to the carbon atom of the bicycle of the formula (I), or
R b) für (D-2) Rb) for (D-2)
(D-2) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder c) für einen Rest der Formel (D-2) in which the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or c) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder f) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder g) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, in which the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or f) a radical of the formula wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or g) a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
G2 für Wasserstoff oder einen Rest aus der Reihe Ci-C i-Alkyl, Halogen-Ci-C i-alkyl und Pyrimidyl steht, G 2 is hydrogen or a radical from the series Ci-C i-alkyl, halo-Ci-C i-alkyl and pyrimidyl,
G3 für einen Rest aus der Reihe Wasserstoff, Halogen und Ci-C/i-Alkyl steht, G 3 is a radical selected from the group consisting of hydrogen, halogen and C 1 -C 1 -alkyl,
X für Sauerstoff steht, X stands for oxygen,
XI für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Methyl und Ethyl steht, X I is a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl and ethyl,
R für gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor substituiertes Ci-C/i-Alkyl steht, W für einen Rest aus der Reihe S, SO und SO2 steht, für einen Rest aus der Reihe Wasserstoff, Methyl und Ethyl steht, für einen Rest aus der Reihe Methyl, Ethyl, Isopropyl, n-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2,2-Difluor-n-propyl, Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Arylmethyl, Arylethyl und Pyridylmethyl, oder für (D-l) oder (D-2) R represents optionally mono-, di-, tri-, tetra- or quintuply fluorine-, chlorine-substituted Ci-C / i-alkyl, W is a radical from the series S, SO and SO2, is a radical from the series hydrogen, methyl and ethyl, is a radical from the series methyl, ethyl, isopropyl, n-propyl, n-butyl, iso-butyl , sec-butyl, tert-butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2,2-difluoro-n-propyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, arylmethyl, arylethyl and pyridylmethyl, or for (Dl) or (D-2)
(D-1 ) (D-2) steht,  (D-1) (D-2),
R23 für Wasserstoff oder Ci-Ce-Alkyl steht, oder R 23 is hydrogen or C 1 -C 6 -alkyl, or
R22 und R23 auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für Morpholinyl stehen. R 22 and R 23 together with the nitrogen atom to which they are attached represent morpholinyl.
Vorzugsbereich (5): Eine weitere hervorgehobene Gruppe von Verbindungen der Formel (I) sind solche, in welchen Preferred range (5): Another highlighted group of compounds of the formula (I) are those in which
A für den A-Rest A for the A-remainder
(A-a) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,  (A-a), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I),
G1 für N oder C-B1 steht, G 1 is N or CB 1 ,
B1 für einen Rest aus der Reihe Wasserstoff und Fluor steht, B2 für Wasserstoff steht, T für ein Elektronenpaar steht, B 1 is a radical selected from the group consisting of hydrogen and fluorine, B 2 is hydrogen, T stands for a pair of electrons,
Q für Schwefel steht, Q stands for sulfur,
R1 für Wasserstoff steht, R 1 is hydrogen,
R2 a) für einen B-Rest aus der Reihe R 2 a) for a B residue from the series
(B-39) (B-40) (B-41 ) (B-39) (B-40) (B-41)
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin (B-42) (B-43) (B-44) (B- 45), wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of the formula (I) wherein
G2 für Wasserstoff oder einen Rest aus der Reihe Ci-C i-Alkyl, Halogen-Ci-C i-alkyl, Ci-C i-Alkoxy, Halogen-Ci-C i-alkoxy, Ci-C4-Alkylthio-Ci-C4-alkyl, halogeniertes Ci-C4-Alkylthio-Ci-C4-alkyl, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylthio, C1-C4- Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl steht, oder G 2 is hydrogen or a radical from the series Ci-C i-alkyl, halo-Ci-C i-alkyl, Ci-C i-alkoxy, halo-Ci-C i-alkoxy, Ci-C4-alkylthio-Ci C4-alkyl, halogenated Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylthio, C1-C4 haloalkylsulfinyl , Ci-C4-haloalkylsulfonyl, or
R2 aa) für den B-Rest R 2 aa) for the B radical
(B-4) (B-4)
steht, worin für Ci-C4-Alkylthio-Ci-C4-alkyl oder halogeniertes Ci-C4-Alkylthio-Ci-C4-alkyl steht, oder R2 c) für einen Rest der Formel in which is C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or halogenated C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, or R 2 c) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder d) für einen Rest der Formel  wherein the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or d) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder f) für einen Rest der Formel in which the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or f) a radical of the formula
- / R22 - / R 22
I 9  I 9
R steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, für Sauerstoff steht, für den D-Rest  R is wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I), is oxygen, the D moiety
(D-2) steht, worin (D-2) in which
R für jeweils gegebenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituiertes G-C i-Alkyl steht, X1 für Wasserstoff, Methyl oder Fluor steht, R is optionally substituted once, twice, three times, four times or five times by fluorine, chlorine or mono- or disubstituted cyano-substituted GC i-alkyl, X 1 is hydrogen, methyl or fluorine,
W für einen Rest aus der Reihe S, SO und SO2 steht, Y3 für Wasserstoff oder Methyl steht, W is a radical from the series S, SO and SO 2, Y 3 is hydrogen or methyl,
R22 im Fall, dass R2 für f) steht, auch für einen Rest aus der Reihe Methyl, Ethyl, Isopropyl, n-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2,2-Difluor-n- propyl, Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Phenylmethyl, Phenylethyl und Pyridyl steht und R 22 in the case that R 2 is f), also a radical from the series methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2,2, 2-trifluoroethyl, 2,2-difluoroethyl, 2,2-difluoro-n-propyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, phenylmethyl, phenylethyl and pyridyl; and
R23 für einen Rest aus der Reihe Wasserstoff und Ci-Cö-Alkyl steht. R 23 is a radical from the series hydrogen and Ci-Cö-alkyl.
Wenn in obigen Definitionen in Ringen Schwefel und/oder Stickstoff vorkommen, wie beispielsweise in Ausdrücken wie„in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können" oder„in welchen ein oder zwei Ringglieder jeweils durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein können", dann kann, sofern nichts anderes angegeben ist, der Schwefel auch als SO oder SO2 vorliegen, der Stickstoff, sofern er nicht als -N= vorliegt, neben NH auch als N-Alkyl (insbesondere N-Ci-Cö-Alkyl) vorliegen. When in the above definitions in rings sulfur and / or nitrogen occur, as for example in terms such as "in which the rings at least one heteroatom from the series sulfur, oxygen (oxygen atoms and sulfur atoms may not be immediately adjacent) and nitrogen may contain" or "In which one or two ring members may each be replaced by a heteroatom selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen", then, unless otherwise stated, the sulfur may also be referred to as SO or SO 2 are present, the nitrogen, if it is not present as -N =, in addition to NH also as N-alkyl (especially N-Ci-Cö-alkyl) are present.
In den bevorzugten Definitionen, deren Kombination den Vorzugsbereich (1) bildet, ist, sofern nichts anderes angegeben ist, In the preferred definitions, the combination of which forms the preferred range (1), unless otherwise specified
Kation ein Alkaliion ausgewählt aus der Reihe Lithium, Natrium, Kalium, Rubidium, Cäsium, bevorzugt aus der Reihe Lithium, Natrium, Kalium oder ein Cation an alkali metal ion selected from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or a
Erdalkaliion ausgewählt aus der Reihe Beryllium, Magnesium, Calcium, Strontium, Barium, bevorzugt aus der Reihe Magnesium, Calcium, Alkaline earth ion selected from the series beryllium, magnesium, calcium, strontium, barium, preferably from the series magnesium, calcium,
Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom, Aryl (auch als Teil einer größeren Einheit, wie beispielsweise Arylalkyl) ausgewählt aus der Reihe Phenyl, Naphthyl, Anthryl, Phenanthrenyl und steht wiederum bevorzugt für Phenyl, Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine, aryl (also part of a larger unit such as arylalkyl) selected from the series phenyl, naphthyl, anthryl, phenanthrenyl and stands again preferred for phenyl,
Hetaryl (gleichbedeutend mit Heteroaryl, auch als Teil einer größeren Einheit, wie beispielsweise Hetarylalkyl) ausgewählt aus der Reihe Furyl, Thienyl, Pyrrolyl, Pyrazolyl, Imidazolyl, 1,2,3-Triazolyl, 1 ,2,4-Triazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,3,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl, 1 ,2,4-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,2,5- Thiadiazolyl, Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1,2,3-Triazinyl, 1 ,2,4-Triazinyl, 1,3,5- Triazinyl, Benzofuryl, Benzisof ryl, Benzothienyl, Benzisothienyl, Indolyl, Isoindolyl, Indazolyl, Benzothiazolyl, Benzisothiazolyl, Benzoxazolyl, Benzisoxazolyl, Benzimidazolyl, 2,1,3- Benzoxadiazole, Chinolinyl, Isochinolinyl, Cinnolinyl, Phthalazinyl, Chinazolinyl, Chinoxalinyl, Naphthyridinyl, Benzotriazinyl, Purinyl, Pteridinyl und Indolizinyl, Hetaryl (equivalent to heteroaryl, also as part of a larger unit such as hetarylalkyl) selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1, 2,4-triazolyl, oxazolyl, isoxazolyl , Thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1, 2,4 Thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5- Thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1, 2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzoflavyl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl , Benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazoles, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl and indolizinyl,
Heterocyclyl ein gesättigter 4-, 5- oder 6-Ring, der 1 oder 2 Stickstoffatome und/oder ein Sauerstoffatom und/oder ein Schwefelatom enthält, beispielsweise Azetidinyl, Azolidinyl, Azinanyl, Oxetanyl, Oxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl, Thianyl, Tetrahydrofuryl, Piperazinyl, Morpholinyl. In den besonders bevorzugten Definitionen, deren Kombination den Vorzugsbereich (2) bildet, ist, sofern nichts anderes angegeben ist, Heterocyclyl a saturated 4-, 5- or 6-membered ring containing 1 or 2 nitrogen atoms and / or an oxygen atom and / or a sulfur atom, for example azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl , Tetrahydrofuryl, piperazinyl, morpholinyl. In the particularly preferred definitions, the combination of which forms the preferred range (2), unless otherwise stated,
Kation für ein Alkaliion ausgewählt aus der Reihe Lithium, Natrium, Kalium, Rubidium, Cäsium, bevorzugt aus der Reihe Lithium, Natrium, Kalium oder ein Cation for an alkali ion selected from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or a
Erdalkaliion ausgewählt aus der Reihe Beryllium, Magnesium, Calcium, Strontium, Barium, bevorzugt aus der Reihe Magnesium, Calcium, Alkaline earth ion selected from the series beryllium, magnesium, calcium, strontium, barium, preferably from the series magnesium, calcium,
Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom, Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
Aryl (auch als Teil einer größeren Einheit, wie beispielsweise Arylalkyl) ausgewählt aus der Reihe Phenyl, Naphthyl, Anthryl, Phenanthrenyl und steht wiederum bevorzugt für Phenyl, Hetaryl (gleichbedeutend mit Heteroaryl, auch als Teil einer größeren Einheit, wie beispielsweise Hetarylalkyl) ausgewählt aus der Reihe Pyrazolyl, Imidazolyl, 1,2,3-Triazolyl, 1 ,2,4-Triazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1,2,3- Triazinyl, 1 ,2,4-Triazinyl, 1,3,5-Triazinyl, Aryl (also as part of a larger unit, such as arylalkyl) selected from the group phenyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents phenyl, hetaryl (equivalent to heteroaryl, also as part of a larger unit, such as hetarylalkyl) selected from of the series pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1, 2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1, 2, 4-triazinyl, 1,3,5-triazinyl,
Heterocyclyl ausgewählt aus der Reihe Azetidinyl, Azolidinyl, Azinanyl, Oxetanyl, Oxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl, Thianyl, Tetrahydrofuryl, Piperazinyl, Morpholinyl. Heterocyclyl selected from azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl, piperazinyl, morpholinyl.
In den ganz besonders bevorzugten Definitionen bzw. den insbesondere bevorzugten Definitionen, deren Kombination den Vorzugsbereich (3) bilden, steht, sofern nichts anderes angegeben ist, In the most particularly preferred definitions or the particularly preferred definitions whose combination form the preferred range (3), unless otherwise stated,
Kation für ein Alkaliion aus der Reihe Lithium, Natrium, Kalium, Rubidium, Cäsium, bevorzugt aus der Reihe Lithium, Natrium, Kalium oder ein Erdalkaliion aus der Reihe Beryllium, Magnesium, Calcium, Strontium, Barium, bevorzugt aus der Reihe Magnesium, Calcium, Cation for an alkali metal ion from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or a Beryllium, magnesium, calcium, strontium, barium alkaline earth metal, preferably magnesium, calcium,
Heterocyclyl für Oxetanyl, Thiethanyl, Tetrahydrof ryl und Morpholinyl. Aryl für Phenyl, Heterocyclyl for oxetanyl, thiethanyl, tetrahydrof ryl and morpholinyl. Aryl for phenyl,
Hetaryl (gleichbedeutend mit Heteroaryl, auch als Teil einer größeren Einheit, wie beispielsweise Hetarylalkyl) für einen Rest aus der Reihe Pyridyl, Pyrimidyl, Pyrazinyl, Pyridazinyl, Thiazolyl und Pyrazolyl. Hetaryl (synonymous with heteroaryl, as part of a larger unit, such as hetarylalkyl) for a radical from the series pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, thiazolyl and pyrazolyl.
In den Definitionen, die den Vorzugsbereich (4) bilden, steht In the definitions that make up the preferential range (4) stands
Halogen für Fluor, Chlor, Brom und Iod, bevorzugt wiederum für Fluor, Chlor und Brom.  Halogen for fluorine, chlorine, bromine and iodine, preferably again fluorine, chlorine and bromine.
Durch Halogen substituierte Reste, z.B. Halogenalkyl (= Haloalkyl), sind einfach oder mehrfach bis zur maximal möglichen Substituentenzahl halogeniert. Bei mehrfacher Halogenierung können die Halogenatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom oder Iod, insbesondere für Fluor, Chlor oder Brom. Halogen substituted radicals, e.g. Haloalkyl (= haloalkyl) are halogenated once or several times up to the maximum possible number of substituents. For multiple halogenation, the halogen atoms may be the same or different. Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
Gesättigte oder ungesättigte Kohlenwasserstoffreste wie Alkyl oder Alkenyl können, auch in Verbindung mit Heteroatomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein. Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
Gegebenenfalls substituierte Reste können, wenn nichts anderes erwähnt ist, einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können. Unless otherwise specified, optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
Wenn T im Rest A der Formel (A-a) When T in the radical A of the formula (A-a)
(A-a) für ein Elektronenpaar steht, liegt der Rest als Pyridinderivat der Formel  (A-a) is an electron pair, the remainder is as a pyridine derivative of the formula
vor. Wenn T im Rest A der Formel (A-a) in front. When T in the radical A of the formula (Aa)
(A-a) für Sauerstoff steht, liegt der Rest als Pyridin-N-Oxid-derivat der Formel  (A-a) is oxygen, the remainder is a pyridine-N-oxide derivative of the formula
vor. Auf die Darstellung der Formalladungen (+ am Stickstoff und - am Sauerstoff) wurde hier verzichtet. in front. The representation of the formal charges (+ on the nitrogen and - on the oxygen) was omitted here.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden. The general or preferred radical definitions or explanations given above apply correspondingly to the end products and to the starting materials and intermediates. These remainder definitions can be combined with one another as desired, ie also between the respective preferred ranges.
Erfindungsgemäß bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (1)). Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferred range (1)).
Erfindungsgemäß besonders bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (2)). Particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred (preferred range (2)).
Erfindungsgemäß ganz besonders bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (3)). Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred (preferred range (3)).
Erfindungsgemäß insbesonders bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als hervorgehoben aufgeführten Bedeutungen vorliegt (Vorzugsbereich (4))· Particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being highlighted (preferred range (4))
Eine bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für den Rest der Formel (A-a) A preferred embodiment of the invention relates to compounds of the formula (I) in which A represents the radical of the formula (Aa)
(A-a) steht.  (A-a) stands.
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für Pyridin-3-yl steht. A further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyridin-3-yl.
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für 5-Fluor-pyridin-3-yl steht. A further preferred embodiment of the invention relates to compounds of the formula (I) in which A is 5-fluoropyridin-3-yl.
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für Pyrimidin-5-yl steht. Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für Pyridazin-4-yl steht. A further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyrimidin-5-yl. A further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyridazin-4-yl.
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 die unter a) aufgeführten Bedeutungen hat. A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under a).
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 die unter b) aufgeführten Bedeutungen hat. A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under b).
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 die unter c) aufgeführten Bedeutungen hat. A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under c).
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 die unter d) aufgeführten Bedeutungen hat. Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 die unter e) aufgeführten Bedeutungen hat. A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under d). A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under e).
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 die unter f) aufgeführten Bedeutungen hat. A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under f).
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 die unter g) aufgeführten Bedeutungen hat. Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 für den Rest (D-2) A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under g). A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical (D-2)
(D-2) steht.  (D-2) stands.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte (auch für die Verbindungen der später aufgeführten Formeln (I-A) bis (I-P) und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden. The general or preferred radical definitions or explanations given above apply to the end products (also for the compounds of the formulas (IA) to (IP) listed below and correspondingly to the starting materials and intermediates.) These radical definitions can be used among one another, ie also between the respective Preferred areas, can be combined arbitrarily.
In einer bevorzugten en der Formel (I-A) In a preferred en of the formula (I-A)
In einer weiteren bevo rbindungen der Formel (I-B) In a further compound of the formula (I-B)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-C) In a further preferred embodiment, the invention relates to compounds of the formula (I-C)
,„„ , ""
- 124 - - 124 -
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-D) In a further preferred embodiment, the invention relates to compounds of the formula (ID)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-E) In a further preferred embodiment, the invention relates to compounds of the formula (I-E)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-F) In a further preferred embodiment, the invention relates to compounds of the formula (I-F)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-G) In a further preferred embodiment, the invention relates to compounds of the formula (I-G)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-H) In a further preferred embodiment, the invention relates to compounds of the formula (I-H)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-I) In a further preferred embodiment, the invention relates to compounds of the formula (II)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-J) In a further preferred embodiment, the invention relates to compounds of the formula (IJ)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-K) In a further preferred embodiment, the invention relates to compounds of the formula (IK)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-M) _ In a further preferred embodiment, the invention relates to compounds of the formula (III) _
- 126 -  - 126 -
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-N) In a further preferred embodiment, the invention relates to compounds of the formula (I-N)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-O) In a further preferred embodiment, the invention relates to compounds of the formula (I-O)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-P) In a further preferred embodiment, the invention relates to compounds of the formula (IP)
In den Formeln (I-A) bis (I-P) haben die Variablen die weiter oben genannten Bedeutungen. In the formulas (I-A) to (I-P), the variables have the meanings mentioned above.
Die Verbindungen der Formel (I) und deren Säureadditionssalze und Metallsalzkomplexe besitzen gute Wirksamkeit, insbesondere zur Bekämpfung von tierischen Schädlingen, zu denen Arthropoden und insbesondere Insekten zählen. The compounds of the formula (I) and their acid addition salts and metal salt complexes have good activity, in particular for combating animal pests, which include arthropods and in particular insects.
Als geeignete Salze der Verbindungen der allgemeinen Formel (I) können übliche nicht toxische Salze, d. h. Salze mit entsprechenden Basen und Salze mit zugesetzten Säuren genannt werden. Vorzugsweise sind Salze mit anorganischen Basen, wie Alkalimetallsalze, beispielsweise Natrium-, Kalium- oder Cäsiumsalze, Erdalkalimetallsalze, beispielsweise Calzium- oder Magnesiumsalze, Ammoniumsalze, Salze mit organischen Basen sowie mit anorganischen Aminen, beispielsweise Triethylammonium-, Dicyclohexylammonium-, Ν,Ν'-Dibenzylethylendiammonium-, Pyridinium-, Picolinium- oder Ethanolammoniumsalze, Salze mit anorganischen Säuren, beispielsweise Hydrochloride, Hydrobromide, Dihydrosulfate, Trihydrosulfate, oder Phosphate, Salze mit organischen Carbonsäuren oder organischen Sulfosäure, beispielsweise Formiate, Acetate, Trifluoracetate, Maleate, Tartrate, Methansulfonate, Benzolsulfonate oder para-Toluolsulfonate, Salze mit basischen Aminosäuren, beispielsweise Arginate, Aspartate oder Glutamate und Ähnliches zu nennen. Die Verbindungen der Formel (I) können gegebenenfalls auch in Abhängigkeit von der Art der Substituenten als Stereoisomere, d.h. als geometrische und/oder als optische Isomere oder Isomerengemische vorliegen in unterschiedlichen Zusammensetzungen vorliegen. Sowohl die reinen Stereoisomeren als auch beliebige Gemische dieser Isomeren sind Gegenstand dieser Erfindung, auch wenn hier im Allgemeinen nur von Verbindungen der Formel (I) die Rede ist. Suitable salts of the compounds of the general formula (I) may be customary non-toxic salts, ie salts with corresponding bases and salts with added acids. Preferably, salts with inorganic bases, such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases and with inorganic amines, for example triethylammonium, dicyclohexylammonium, Ν, Ν'- Dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates, or phosphates, salts with organic carboxylic acids or organic sulfonic acid, for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesulfonates, benzenesulfonates or para-toluenesulfonates, salts with basic amino acids, for example arginates, aspartates or glutamates, and the like. Depending on the nature of the substituents, the compounds of the formula (I) may also be present in different compositions as stereoisomers, ie as geometric and / or optical isomers or mixtures of isomers. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.
Die Erfindung betrifft daher sowohl die reinen Enantiomeren und Diastereomeren, als auch deren Gemische zur Bekämpfung von tierischen Schädlingen, zu denen Arthropoden und insbesondere Insekten zählen. The invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for controlling animal pests, which include arthropods and in particular insects.
Vorzugsweise werden jedoch die optisch aktiven, stereoisomeren Formen der Verbindungen der Formel (I) und deren Salze erfindungsgemäß verwendet. Preferably, however, the optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention.
Im Folgenden werden die Begriffe „Synthesebeispiel" und„Anwendungsbeispiel" gleichbedeutend verwendet, sofern nichts anderes angegeben ist. In the following, the terms "Synthesis Example" and "Application Example" are used synonymously unless otherwise specified.
Weiter wurde gefunden, dass sich Verbindungen der Formel (I) nach der im Folgenden beschriebenen Methode A herstellen lassen. Methode A: Verbindungen der Formel (I), in denen der Heterocyclus A für gegebenenfalls mit einem Rest B2 substituiertes Pyrimidin-5-yl (A-a; G1 = N), Pyridin-3-yl (A-a; G1 = C-B1), Pyrazin-2-yl (A-b), Pyridazin-3-yl (A-c), Thiazol-5-yl (A-d), Isothiazol-4-yl (A-e) und Pyrazol-4-yl (A-f) steht, können beispielsweise gemäß Methode A (vgl. Reaktionsschema I) in drei Schritten hergestellt werden. It has also been found that compounds of the formula (I) can be prepared by the method A described below. Method A: Compounds of the formula (I) in which the heterocycle A is pyrimidin-5-yl optionally substituted by a radical B 2 (Aa; G 1 = N), pyridin-3-yl (Aa; G 1 = CB 1 ), Pyrazine-2-yl (Ab), pyridazin-3-yl (Ac), thiazol-5-yl (Ad), isothiazol-4-yl (Ae) and pyrazol-4-yl (Af), for example according to method A (see Reaction Scheme I) in three steps.
Reaktionsschema I - Methode A Scheme I - Method A
(AM) (A1 -III) (AM) (A1 -III)
Lawessons'sLawessons ' s
2. Schritt Reagenz 2nd step reagent
120 °C  120 ° C
(I) (A1 -IV) (I) (A1-IV)
LG = Leaving group, z. B. Halogen, CO-OR (R = Aryl, Alkyl) LG = Leaving group, z. Halogen, CO-OR (R = aryl, alkyl)
W-lmidazol-l -yl, OH etc.  W-imidazole-1-yl, OH etc.
Im Reaktionsschema I haben A, R1 und R2 die oben genannten Bedeutungen, sofern nichts anderes angegeben ist. In Reaction Scheme I, A, R 1 and R 2 have the meanings given above unless otherwise specified.
Beispielsweise können die substituierten Aniline der Formel (Al-I) mit aktivierten Carbonsäuren (z. B. als Carbonsäurechlorid oder dessen Hydrochlorid) der Formel (AI -II) in Gegenwart von basischen Reaktionshilfsmitteln in einem ersten Reaktionsschritt zu Verbindungen der Formel (AI -III) umgesetzt werden. Diese werden dann durch Schwefeldonatoren wie z. B. Lawesson's Reagenz zu Verbindungen der Formel (AI -IV) thioniert. In einem dritten Reaktionsschritt können diese dann in Gegenwart einer geeigneten Base, beispielsweise Kaliumcarbonat, unter Bildung der Verbindungen der Formel (I) cyclisiert werden. For example, the substituted anilines of the formula (Al-I) with activated carboxylic acids (for example as the carboxylic acid chloride or its hydrochloride) of the formula (AI-II) in the presence of basic reaction auxiliaries in a first reaction step to compounds of formula (AI -III ) are implemented. These are then by sulfur donors such. B. Lawesson's reagent to compounds of formula (AI -IV) thionated. In a third reaction step, these can then be cyclized in the presence of a suitable base, for example potassium carbonate, to give the compounds of the formula (I).
Methode A - Schritt 1: Die Verbindungen der Formel (Al-I) sind teilweise bekannt und kommerziell erhältlich bzw. können nach im Prinzip bekannten Herstellungsverfahren (z. B. für R1 = H, R2 = Br; 4- Brom-2-fluoranilin (vgl. GB 2 065 654 A) erhalten werden. Method A - Step 1: The compounds of the formula (Al-I) are known in some cases and are commercially available or can be prepared by methods known in principle (for example for R 1 HH, R 2 BrBr 4 -bromo-2 fluoraniline (see GB 2 065 654 A).
Die Verbindungen der Formel (AI -II) sind teilweise bekannt und kommerziell erhältlich bzw. können nach im Prinzip bekannten Herstellungsverfahren (z. B. für A = Pyridin-3-yl, LG = Cl; Nicotinsäurechlorid (Journal of the American Chemical Society (1953), 75, 4364) oder für A = 5-Fluor- pyridin-3-yl, LG = Cl; 5-Fluornicotinoylchlorid (vgl. US 2,516,830) erhalten werden. The compounds of the formula (AI-II) are known in some cases and are commercially available or can be prepared by methods known in principle (for example for A = pyridin-3-yl, LG = Cl; Nicotinic acid chloride (Journal of the American Chemical Society (1953), 75, 4364) or for A = 5-fluoropyridin-3-yl, LG = Cl; 5-fluoronicotinoyl chloride (see US 2,516,830).
Für den Amidierungsschritt sind zahlreiche Reaktionsbedingungen beschrieben worden, z.B. G. Benz in Comprehensive Organic Synthesis, Ist Ed., Pergamon Press, Oxford, 1991, Vol. 6, S. 381-417; P.D. Bailey et al. in Comprehensive Organic Functional Group Transformation, Ist Ed., Elsevier Science Ltd., Oxford, 1995, Vol. 5, S. 257-308 und R.C. Larock in Comprehensive Organic Transformations, 2nd Ed., Wiley-VCH, New York, Weinheim, 1999, S. 1929-1994. Einige dieser Reaktionen verlaufen über intermediäre Carbonsäurechloride, die isoliert oder in-situ aus Verbindungen der Formel (AI -II, LG = OH) erzeugt eingesetzt werden können. Die Amidierungsreaktionen erfolgen gegebenenfalls in Gegenwart eines Kondensationsmittels, gegebenenfalls in Gegenwart eines Säureakzeptors und gegebenenfalls in Gegenwart eines Lösungsmittels. Numerous reaction conditions have been described for the amidation step, eg G. Benz in Comprehensive Organic Synthesis, Ist Ed., Pergamon Press, Oxford, 1991, Vol. 6, pp. 381-417; PD Bailey et al. in Comprehensive Organic Functional Group Transformation, Ist Ed., Elsevier Science Ltd., Oxford, 1995, Vol. 5, pp. 257-308 and RC Larock in Comprehensive Organic Transformations, 2nd ed., Wiley-VCH, New York, Weinheim , 1999, pp. 1929-1994. Some of these reactions proceed via intermediate carboxylic acid chlorides, which can be used in isolation or generated in situ from compounds of the formula (AI-II, LG = OH). Optionally, the amidation reactions are carried out in the presence of a condensing agent, optionally in the presence of an acid acceptor and optionally in the presence of a solvent.
Als Kondensationsmittel kommen alle üblicherweise für derartige Amidierungsreaktionen verwendbaren Kondensationsmittel infrage. Beispielhaft genannt seien Säurehalogenidbildner wie Phosgen, Phosphortrichlorid, Oxalylchlorid oder Thionylchlorid; Carbodiimide, wie NN - Dicyclohexylcarbodiimid (DCC) und l-(3-Dimethylaminopropyl)-3-ethyl-carbodiimid (EDCI), oder andere übliche Kondensationsmittel, wie Phosphorpentoxid, Polyphosphorsäure, NN - Carbonyldiimidazol, 2-Chlorpyridin 1 -Methoiodid (Mukaiyamas Reagenz), 2-Ethoxy-N- ethoxycarbonyl-l,2-dihydrochinolin (EEDQ), Triphenylphosphin/Tetrachlorkohlenstoff, Brom- tripyrrolidino-phosphonium-hexafluorphosphat (BROP), 0-( H-Benzotriazol-l- yloxy)tris(dimethylamino)phosphonium-hexafluorphosphat (BOP), Ν,Ν,Ν',Ν'-Suitable condensing agents are all condensing agents customarily used for such amidation reactions. Examples which may be mentioned are acid halide formers such as phosgene, phosphorus trichloride, oxalyl chloride or thionyl chloride; Carbodiimides such as NN-dicyclohexylcarbodiimide (DCC) and 1- (3-dimethylaminopropyl) -3-ethyl-carbodiimide (EDCI), or other conventional condensing agents such as phosphorus pentoxide, polyphosphoric acid, NN-carbonyldiimidazole, 2-chloropyridine 1-methiodide (Mukaiyamas reagent ), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyrrolidino-phosphonium hexafluorophosphate (BROP), 0- (H-benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (BOP), Ν, Ν, Ν ' , Ν ' -
Bis(tetramethylen)cloruronium-tetrafluorborat, 0-( H-Benzotriazol- 1 -yl)-N,N,N',N - tetramethyluronium-hexafluorphosphat (HBTU), 0-( H-Benzotriazol- 1 -yl)-N,N,N',N - bis(tetramethylen)uronium-hexafluorphosphat, 0-( H-Benzotriazol- 1 -yl)-N,N,N',N - tetramethyluronium-tetrafluorborat (TBTU), 0-(7H-Benzotriazol-l -yl)-N,N,N',N - bis(tetramethylen)uronium-tetrafluorborat, 0-(7-Azabenzotriazol-l-yl)-NNN',N -tetramethyluronium- hexafluorphosphat (HATU), 1 -Hydroxybenzotriazol (HOBt) und 4-(4,6-Dimethoxy-l,3,5-triazin-2-yl)- 4-methylmorpholiniumsalz (DMT.MM), meistens als Chlorid verfügbar. Diese Reagenzien können separat oder gegebenenfalls in Kombination eingesetzt werden. Als Säureakzeptor kommen alle üblichen anorganischen oder organischen Basen infrage, beispielsweise Triethylamin, Diisopropylethylamin, N-Methylmorpholin oder NN-Dimethylaminopyridin. Das erfindungsgemäße Verfahren A wird gegebenenfalls in Gegenwart eines geeigneten Reaktionshilfstoffes wie beispielsweise NN-Dimethylformamid oder NN-Dimethylaminopyridin durchgeführt. Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe (wie Petrolether, Toluol), halogenierte Kohlenwasserstoffe (wie Chlortoluol, Dichlormethan, Chloroform, 1 ,2-Dichlorethan), Ether (wie Diethylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan), Ester (wie Essigsäureethylester- oder - methylester), Nitrokohlenwasserstoffe (wie Nitromethan, Nitroethan, Nitrobenzol), Nitrile (wie Acetonitril, Benzonitril), Amide (wie NN-Dimethylformamid, NN-Dimethylacetamide, N- Methylformanilid, N-Methylpyrrolidon, Hexamethylphosphorsäuretriamid) sowie Dimethylsulfoxid oder Wasser oder Gemische der genannten Lösungsmittel. Bis (tetramethylene) cloruronium tetrafluoroborate, 0- (H-benzotriazol-1-yl) -N, N, N ' , N-tetramethyluronium hexafluorophosphate (HBTU), 0- (H-benzotriazol-1-yl) -N, N, N ' , N - bis (tetramethylene) uronium hexafluorophosphate, 0- (H-benzotriazol-1-yl) -N, N, N ' , N-tetramethyluronium tetrafluoroborate (TBTU), 0- (7H-benzotriazole) 1 -yl) -N, N, N ' , N - bis (tetramethylene) uronium tetrafluoroborate, 0- (7-azabenzotriazol-1-yl) -NNN ' , N-tetramethyluronium hexafluorophosphate (HATU), 1-hydroxybenzotriazole ( HOBt) and 4- (4,6-dimethoxy-l, 3,5-triazin-2-yl) -4-methylmorpholinium salt (DMT.MM), most commonly available as chloride. These reagents may be used separately or optionally in combination. Suitable acid acceptors are all customary inorganic or organic bases, for example triethylamine, diisopropylethylamine, N-methylmorpholine or N, N-dimethylaminopyridine. If appropriate, process A according to the invention is carried out in the presence of a suitable reaction auxiliary, for example N, N-dimethylformamide or N, N-dimethylaminopyridine. Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons (such as petroleum ether, toluene), halogenated hydrocarbons (such as chlorotoluene, dichloromethane, chloroform, 1, 2-dichloroethane), ethers (such as diethyl ether, dioxane, tetrahydrofuran , 1, 2-dimethoxyethane), esters (such as ethyl acetate or methyl ester), nitrohydrocarbons (such as nitromethane, nitroethane, nitrobenzene), nitriles (such as acetonitrile, benzonitrile), amides (such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide , N-methylpyrrolidone, hexamethylphosphoric triamide) and dimethyl sulfoxide or water or mixtures of said solvents.
Zur Synthese der Verbindungen der Formel (AI -III) können aber auch gemischte Anhydride (LG = COOR) verwendet werden (vgl. G. W. Anderson et al. J. Am. Chem. Soc. 1967, 89, 5012-5017). Bei diesem Verfahren, das über Verbindungen der Formel (AI -II, LG = CO-OR, R = Alkyl, Aryl) führt, können Chlorameisensäureester zum Einsatz kommen, wie z.B. Chlorameisensäureisobutylester (LG = COOR mit R = iso-Butyl) und Chlorameisensäure-isopropylester (LG = COOR mit R = iso-Propyl). Ebenfalls können dafür Diethylacetylchlorid, Trimethylacetylchlorid und ähnliche Verbindungen verwendet werden. However, mixed anhydrides (LG = COOR) can also be used for the synthesis of the compounds of the formula (AI-III) (compare G.W. Anderson et al., J. Am. Chem. Soc., 1967, 89, 5012-5017). In this process, which leads via compounds of the formula (AI-II, LG = CO-OR, R = alkyl, aryl), chloroformates can be used, such. Isobutyl chloroformate (LG = COOR with R = isobutyl) and isopropyl chloroformate (LG = COOR with R = isopropyl). Also, diethylacetyl chloride, trimethylacetyl chloride and the like can be used therefor.
Methode A - Schritt 2: Die Amidfunktion der Carbonsäureamide des Typs (AI -III) kann durch geeignete Schwefelungsreagenzien, z. B. Lawesson's Reagenz oder Phosphor(V)-sulfid, unter Erhitzen in einem geeigneten Lösungsmittel, z. B. Toluol oder Anisol, in eine Thioamidfunktion überführt werden, wodurch Verbindungen des Typs (AI -IV) entstehen [vgl. z. B. WO2013/33901 für 5-Brom-N- (2,6-difluorphenyl)pyridin-3-carbothioamid]. Bei diesem Reaktionstyp kann bereits teilweise eine Cyclisierung zum Verbindungstyp (I) erfolgen. Method A - Step 2: The amide function of the carboxylic acid amides of type (AI-III) can be achieved by suitable sulfurization reagents, e.g. Lawesson's reagent or phosphorus (V) sulfide, with heating in a suitable solvent, e.g. As toluene or anisole, are converted into a thioamide function, whereby compounds of the type (AI -IV) are formed [cp. z. WO2013 / 33901 for 5-bromo-N- (2,6-difluorophenyl) -pyridine-3-carbothioamide]. Partial cyclization to the type of compound (I) can already take place in this type of reaction.
Methode A - Schritt 3: Schließlich lassen sich die Verbindungen der Formel (I) nach literaturbekannten Methoden (vgl. z. B. WO2013/33901 für 2-(5-Brompyridin-3-yl)-4-fluor-l,3- benzothiazol)) durch Erhitzen in einem geeignetem Lösungsmittel, z. B. Toluol oder DMF, in Anwesenheit einer Base wie z. B. Natriumhydrid oder Kaliumcarbonat, in die Thiazole der Formel (I) überführen. Method A - Step 3: Finally, the compounds of the formula (I) can be prepared by methods known from the literature (cf., for example, WO2013 / 33901 for 2- (5-bromopyridin-3-yl) -4-fluoro-1, 3 benzothiazole)) by heating in a suitable solvent, e.g. For example, toluene or DMF, in the presence of a base such as. As sodium hydride or potassium carbonate, in the thiazoles of the formula (I) convert.
Wird bei dem erfindungsgemäßen Verfahren zur Herstellung der Verbindungen der Formel (I) als Verbindung der Formel (Al -I) 4-Brom-2-fluoranilin (R1 = H, R2 = Br) und als Verbindung der Formel (AI -II) 3-(Chlorcarbonyl)pyridiniumchlorid (A = 3-Pyridin-3-yl) eingesetzt, so entsteht zunächst das N- (4-Brom-2-fluorphenyl)nicotinamid (A = 3-Pyridin-3-yl, R1 = H, R2 = Br). Nachfolgende Thionierung und Cyclisierung führt dann zum 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1)), A = Pyridin-3-yl, R1 = H, R2 = Br) [vgl. Anwendungsbeispiel I-a-1]. Is in the process of the invention for preparing the compounds of formula (I) as the compound of formula (Al-I) 4-bromo-2-fluoroaniline (R 1 = H, R 2 = Br) and as a compound of formula (AI -II ) 3- (Chlorocarbonyl) pyridinium chloride (A = 3-pyridin-3-yl), the N- (4-bromo-2-fluorophenyl) nicotinamide (A = 3-pyridin-3-yl, R 1 = H, R 2 = Br). Subsequent thionation and cyclization then gives 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1)), A = pyridin-3-yl, R 1 = H, R 2 = Br ) [see. Application Example Ia-1].
Verbindungen der Formel (I), in denen R2 für Halogen, beispielsweise Brom oder lod, steht, können gemäß Reaktionsschema I aus halogenierten 2-Fluor-anilinderivaten der Formel (Al-I) erhalten werden. Hieraus können nach literaturbekannten Methoden (B bis F) weitere Verbindungen der Formel (I) generiert werden. Beispielhaft sind die Methoden B bis F und die daraus resultierenden Produkttypen in Reaktionsschema II dargestellt. Compounds of the formula (I) in which R 2 is halogen, for example bromine or iodine, can be obtained according to Reaction Scheme I from halogenated 2-fluoroaniline derivatives of the formula (Al-I). From this, further compounds of the formula (I) can be generated by methods known from the literature (B to F). By way of example, the methods B to F and the product types resulting therefrom are shown in Reaction Scheme II.
Methode B/F: Gemäß US 2012/253040 lassen sich bromierte Benzothiazole mit gegebenenfalls in-situ erzeugten substituierten Arylboronsäuren bzw. Arylboronsäurepinakolestern in Anwesenheit von Kupplungskatalysatoren, wie Tetrakis(triphenylphosphin)-palladium(0) oder 1,1 '- Bis(diphenylphosphino)ferrocen]dichlor-palladium(II), in Anwesenheit einer Base, wie z. B. Natriumcarbonat, in einem inerten organischen Lösungs- bzw. Verdünnungsmittel, z. B. Dioxan in Kombination mit Wasser, arylieren (Methode B), wodurch kohlenstoffverknüpfte Verbindungen des Typs (I-b) [vgl. auch Anwendungsbeispiel (9)] erhalten werden können. Auch gegebenenfalls substituierte heteroaromatische Boronsäuren bzw. deren Pinakolester können analog mit Brom- benzothiazolen nach Methode B umgesetzt werden [vgl. z. B. WO 2014/15088]. Method B / F: According to US 2012/253040, brominated benzothiazoles can be prepared with in situ generated substituted arylboronic acids or aryl boronic acid pinacol esters in the presence of coupling catalysts, such as tetrakis (triphenylphosphine) palladium (0) or 1,1'-bis (diphenylphosphino) ferrocene] dichloro-palladium (II), in the presence of a base such. For example, sodium carbonate, in an inert organic solvent or diluent, for. As dioxane in combination with water, arylation (Method B), whereby carbon-linked compounds of the type (I-b) [cf. also application example (9)] can be obtained. Even optionally substituted heteroaromatic boronic acids or their pinacol esters can be reacted analogously with bromobenzothiazoles according to Method B [cf. z. WO 2014/15088].
Alternativ können die Verbindungen der Formel (I-a) zunächst mittels literaturbekannter Methoden in Verbindungen des Typs (I-h) überführt werden, die dann anschließend mit halogen-aktivierten und gegebenenfalls, weiter substituierten Heterocyclen gemäß Reaktionsschema II (Methode F) [vgl. T. Ishiyama et al, J. Org. Chem., 1995, 60, 7508 - 7510; WO 2010/151601] in einem inerten organischen Lösungs- bzw. Verdünnungsmittel zu kohlenstoffverknüpften Verbindungen des Typs (I-i) weiterreagieren. Alternatively, the compounds of the formula (I-a) can first be converted by methods known from the literature into compounds of the type (I-h) which are then subsequently reacted with halogen-activated and optionally, further substituted heterocycles according to Reaction Scheme II (Method F) [cf. T. Ishiyama et al, J. Org. Chem., 1995, 60, 7508-7510; WO 2010/151601] continue to react in an inert organic solvent or diluent to give carbon-bonded compounds of the type (I-i).
Reaktionsschema II - Methode B bis F Reaction Scheme II - Method B to F
Für A = Fyridin-3-yl und R1 = H vergleiche auch: For A = fyridin-3-yl and R1 = H also compare:
Anwendungsbeispiel (9)  Application Example (9)
Anwendungsbeispiel (13) Application example (13)
Anwendungsbeispiel (15) Application Example (15)
Anwendungsbeispiel (18) Application example (18)
Anwendungsbeispiel (24) Application example (24)
Anwendungsbeispiel (28) Application example (28)
Als Kupplungskatalysatoren kommen Palladium-Katalysatoren wie [ 1,1 ' -Bis (diphenylphosphino)ferrocen]dichlorpalladium(II)] oder Tetrakis(triphenylphosphin) Palladium(O) in Betracht. Suitable coupling catalysts are palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II)] or tetrakis (triphenylphosphine) palladium (O).
Als basische Reaktionshilfsmittel zur Durchführung der Verfahren gemäß Reaktionsschema II finden bevorzugt Carbonate des Natriums oder Kaliums Verwendung. The basic reaction auxiliaries for carrying out the processes according to Reaction Scheme II are preferably carbonates of sodium or potassium.
Als Lösungsmittel werden bevorzugt Nitrile wie Acetonitril, Benzonitril, insbesondere Acetonitril, oder Ether wie Diethylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan, insbesondere 1,2- Dimethoxyethan in Kombination mit Wasser eingesetzt. The solvents used are preferably nitriles, such as acetonitrile, benzonitrile, in particular acetonitrile, or ethers, such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, in particular 1,2-dimethoxyethane in combination with water.
Methode C: Mittels Katalyse durch geeignete Kupplungskatalysatoren, wie Tris-(dibenzylidenaceton)- dipalladium(O) unter Verwendung geeigneter Liganden, z. B. 2,2'-Bis-(diphenylphosphino)-l,l'- binaphthyl (BINAP), und einer Base wie beispielsweise Natrium-tert-butanolat lassen sich bromierte Benzothiazole der Formel (I-a) in einem inerten organischen Lösungs- bzw. Verdünnungsmittel mit gegebenenfalls substituierten aliphatischen primären bzw. sekundären Aminen zu Verbindungen des Typs (I-c) bzw. (I-d) [vgl. z. B. WO 2011/140160; vgl. auch Anwendungsbeispiele (13) und (15)] oder Arylmethyl- bzw Hetarylmethylaminen umsetzen [vgl. z. B. WO 2003/045930 zur Synthese von N- Benzyl-2-(4-methoxyphenyl)-l,3-benzothiazol-6-amin; vgl. auch Anwendungsbeispiel 17]. Method C: By means of catalysis by suitable coupling catalysts, such as tris (dibenzylideneacetone) dipalladium (O) using suitable ligands, for. B. 2,2'-bis (diphenylphosphino) -l, l'binaphthyl (BINAP), and a base such as sodium tert-butoxide can be brominated benzothiazoles of the formula (Ia) in an inert organic solution or Diluents with optionally substituted aliphatic primary or secondary amines to give compounds of the type (Ic) or (Id) [cf. z. For example WO 2011/140160; see. also application examples (13) and (15)] or arylmethyl or hetarylmethylamines implement [cp. z. For example, WO 2003/045930 for the synthesis of N-benzyl-2- (4-methoxyphenyl) -1,3-benzothiazol-6-amine; see. also application example 17].
Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe. Bevorzugt werden aromatische Kohlenwasserstoffe (beispielsweise Toluol) eingesetzt. Methode D: Mit gegebenenfalls substituierten Anilinen reagieren bromierte Benzothiazole der Formel (I-a) in einem inerten organischen Lösungs- bzw. Verdünnungsmittel zu den Arylamino- Verbindungen der Formel (I-e) [vgl. auch Anwendungsbeispiel 18]), bevorzugt unter Katalyse durch Kupplungskatalysatoren wie Palladium(II)diacetat in Anwesenheit einer Base, z. B. Kalium-tert- butanolat (vgl. WO 2010/044441 zur Herstellung von N,2-Dimethyl-N-phenyl-l,3-benzothiazol-6- amin). Gegebenenfalls substituierte Amino-heteroaromaten lassen sich auf analoge Weise zu Verbindungen der Formel (I-f) umsetzen [vgl. auch Anwendungsbeispiel (24)], z. B. unter Katalyse durch geeignete Kupplungskatalysatoren wie Tris-(dibenzylidenaceton)-dipalladium(0), mit geeigneten Liganden, z. B. 2,2'-Bis-(diphenylphosphino)-l,l'- binaphthyl (BINAP) und einer Base, bspw. Natrium- tert-butanolat [vgl. z. B. US 2007/66588 zur Herstellung von 2-substituiertem N-(Pyrimidin-2-yl)-l,3- benzothiazol-6-amin]. Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons (for example toluene). Method D: With optionally substituted anilines, brominated benzothiazoles of the formula (I-a) react in an inert organic solvent or diluent to give the arylamino compounds of the formula (I-e) [cf. also Application Example 18]), preferably with catalysis by coupling catalysts such as palladium (II) diacetate in the presence of a base, for. B. potassium tert-butoxide (see WO 2010/044441 for the preparation of N, 2-dimethyl-N-phenyl-l, 3-benzothiazol-6-amine). Optionally substituted amino-heteroaromatics can be reacted in an analogous manner to give compounds of the formula (I-f) [cf. also application example (24)], z. Example, with catalysis by suitable coupling catalysts such as tris (dibenzylideneacetone) dipalladium (0), with suitable ligands, eg. B. 2,2'-bis (diphenylphosphino) -l, l'binaphthyl (BINAP) and a base, for example. Sodium tert-butoxide [see. z. US 2007/66588 for the preparation of 2-substituted N- (pyrimidin-2-yl) -1,3-benzothiazol-6-amine].
Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe. Bevorzugt werden aromatische Kohlenwasserstoffe (beispielsweise Toluol) eingesetzt. Methode E: Heterocyclische Amine wie gegebenenfalls substituierte Imidazole, Pyrazole oder Triazole, lassen sich in Anlehnung an die im Reaktionsschema II gezeigte Methode E [vgl. WO 2008/130368] bevorzugt in Gegenwart geeigneter Katalysatoren wie Kupfer(I)iodid, in Anwesenheit basischer Liganden, z. B. N-Methyl-2-(methylamino)ethylamin oder iraft -N,N'-Dimethylcyclohexan-l,2-diamin, und einer Base wie Kalium-tert-butanolat oder Kaliumcarbonat, in einem inerten organischen Lösungsbzw. Verdünnungsmittel in halogenierte, insbesondere bromierte oder iodierte, bicyclische Systeme einführen (vgl. Typ (I-g) und Anwendungsbeispiel 28). Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons (for example toluene). Method E: Heterocyclic amines, such as optionally substituted imidazoles, pyrazoles or triazoles, can be prepared on the basis of the method E shown in Reaction Scheme II [cf. WO 2008/130368] preferably in the presence of suitable catalysts such as copper (I) iodide, in the presence of basic ligands, for. N-methyl-2- (methylamino) ethylamine or iraft-N, N'-dimethylcyclohexane-1,2-diamine, and a base such as potassium tert-butoxide or potassium carbonate, in an inert organic solvent. Introduce diluents into halogenated, in particular brominated or iodinated, bicyclic systems (see Type (Ig) and Application Example 28).
Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe. Bevorzugt werden aromatische Kohlenwasserstoffe (beispielsweise Toluol) eingesetzt, aber auch polarere Lösungsmittel wie DMF. Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons (for example toluene), but also more polar solvents such as DMF.
Verbindungen der Formel (I), in denen R2 für Halogen, beispielsweise Brom oder lod steht, können gemäß Reaktionsschema I aus entsprechend halogenierten 2-Fluor-anilinderivaten erhalten werden. Hieraus können nach literaturbekannten Methoden (G) weitere Verbindungen der Formel (I) generiert werden, wie in Reaktionsschema III dargestellt. Compounds of the formula (I) in which R 2 is halogen, for example bromine or iodine, can be obtained according to Reaction Scheme I from correspondingly halogenated 2-fluoroaniline derivatives. From this, further compounds of the formula (I) can be generated by methods known from the literature (G), as shown in Reaction Scheme III.
Reaktionsschema III - Methode G Reaction Scheme III - Method G
Kohlenmonoxid Carbon monoxide
Pd(ll)-Katalysator  Pd (II) catalyst
Methanol  methanol
Verfahren G  Method G
Schritt 1 Step 1
)  )
Verfahren G Method G
LiOH  LiOH
Schritt 2  step 2
LG = Leaving group, z. B. Halogen, O-CO-R (R = Aryl, Alkyl)  LG = Leaving group, z. Halogen, O-CO-R (R = aryl, alkyl)
A/-lmidazol-1-yl, etc.  A / -imidazol-1-yl, etc.
Methode G - Schritt 1 : Verbindungen der Formel (I), in denen R2 für Halogen, beispielsweise Brom oder lod, steht, können nach literaturbekannten Methoden mit Kohlenmonoxid und einem Alkohol, z. B. Ethanol, unter Katalyse durch geeignete Metallverbindungen wie (1,1'- Bis(diphenylphosphino)ferrocen)-palladium(II)dichlorid, und in Anwesenheit von Basen wie Triethylamin, in geeigneten Lösungsmitteln wie z. B. dem verwendeten Alkohol selbst, THF und/oder DMF, zu den entsprechenden Carbonsäureestern (I-j) umgesetzt werden [vgl. Bioorganic and Medicinal Chemistry Letters, 2012, 22(1), 628 - 633 und darin enthaltene Referenzen für Ethyl-2-[4-(l,3-dioxan- 2-yl)-2-fluorphenyl]-l,3-benzothiazol-6-carboxylat]. Method G - Step 1: Compounds of the formula (I) in which R 2 is halogen, for example bromine or iodine, can be prepared by methods known from the literature using carbon monoxide and an alcohol, eg. As ethanol, with catalysis by suitable metal compounds such as (1,1'-bis (diphenylphosphino) ferrocene) palladium (II) dichloride, and in the presence of bases such as triethylamine, in suitable solvents such. B. the alcohol itself, THF and / or DMF, to the corresponding carboxylic acid esters (Ij) are reacted [see. Bioorganic and Medicinal Chemistry Letters, 2012, 22 (1), 628-633 and references therein for ethyl 2- [4- (1,3-dioxan-2-yl) -2-fluorophenyl] -1,3-benzothiazole-6 carboxylate].
Methode G - Schritt 2: Die Verbindungen der Formel (I-j) können mittels geeigneter Basen, wie z. B. wässriger Lithiumhydroxid- oder Natriumhydroxid-Lösung, in geeigneten Lösungs- bzw. Verdünnungsmitteln, wie z. B. Dioxan oder THF, zu Verbindungen der Formel (I-k) mit freier Säurefunktion umgesetzt werden. Method G - Step 2: The compounds of the formula (I-j) can be prepared by means of suitable bases, such. As aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as. As dioxane or THF, to compounds of formula (I-k) are reacted with free acid function.
Methode G - Alternativschritt 1/2: Alternativ zu den Schritten 1 und 2 können Verbindungen der Formel (I-k) mit freier Säurefunktion auch direkt aus Verbindungen der Formel (I), in denen R2 für Cyano steht, durch Umsetzung mit konzentrierter Salzsäure in Eisessig, gegebenenfalls unter Erwärmung, erhalten werden. Method G - Alternative Step 1/2: As an alternative to steps 1 and 2, compounds of the formula (Ik) with free acid function can also be prepared directly from compounds of the formula (I) in which R 2 is cyano by reaction with concentrated hydrochloric acid in glacial acetic acid , optionally with heating, are obtained.
Methode G - Schritt 3 und 4: Verbindungen der Formel (I), in denen R2 für einen Rest aus der Reihe (C-l) bis (C-9) (Typ I-m) oder für CX-NR22R23 (Typ I-n) steht, können beispielsweise aus Verbindungen der Formel (I), in denen R2 für eine Carboxylgruppe steht (Typ I-k), nach geeigneter Aktivierung (d.h. LG steht für eine gegebenenfalls in-situ erzeugte nucleofuge Abgangsgruppe "Leaving Group") mittels allgemein bekannter Methoden hergestellt werden [vgl. Methode A, Schritt 1]. Method G - Steps 3 and 4: Compounds of the formula (I) in which R 2 is a radical from the series (Cl) to (C-9) (Type Im) or for CX-NR 22 R 23 (Type In) For example, compounds of formula (I) in which R 2 is a carboxyl group (type Ik), after appropriate activation (ie LG represents an optionally in situ generated nucleofuge leaving group "Leaving Group") can be prepared by well-known methods to be produced [cf. Method A, step 1].
Verbindungen der Formel (I), in denen R2 für eine Gruppe der Formel -NR23-C(X)-R22 steht, können beispielsweise aus Verbindungen der Formel (I), in denen R2 für eine Gruppe der Formel -NHR23 steht, mittels N-Acylierungsreaktion unter Verwendung von aktivierten Verbindungen der Formel LG-C(X)- R22, worin LG für eine gegebenenfalls in-situ erzeugte nucleofuge Abgangsgruppe steht, erhalten werden. Compounds of the formula (I) in which R 2 is a group of the formula -NR 23 -C (X) -R 22 can, for example, be prepared from compounds of the formula (I) in which R 2 is a group of the formula -NHR 23 , by N-acylation reaction using activated compounds of the formula LG-C (X) - R 22 , wherein LG is an optionally in situ generated nucleofuge leaving group, can be obtained.
Diese Verbindungen der Formel (I), in denen R2 für -NHR23 steht, lassen sich aus Verbindungen der Formel (I), in denen R2 für eine Carboxylgruppe steht, gemäß dem Reaktionsschema IV nach bekannten Methoden darstellen. These compounds of the formula (I) in which R 2 is -NHR 23 can be prepared from compounds of the formula (I) in which R 2 is a carboxyl group in accordance with Reaction Scheme IV by known methods.
Reaktionsschema IV - Methode Hl Reaction Scheme IV - Method Hl
LG = Leaving group, z. B. Halogen  LG = Leaving group, z. B. halogen
DPPA = Diphenylphosphorylazid  DPPA = diphenylphosphoryl azide
Methode Hl: Beispielsweise können Verbindungen der Formel (I-o) mittels Curtius-Abbau, wie in Houben-Weyl, Methoden der Organischen Chemie, Band XI/1 (Georg Thieme Verlag Stuttgart), S. 865 beschrieben, erhalten werden. Method III: For example, compounds of the formula (I-o) can be obtained by Curtius degradation, as described in Houben-Weyl, Methods of Organic Chemistry, Volume XI / 1 (Georg Thieme Verlag Stuttgart), page 865.
Hierbei können die Verbindungen der Formel (I-k) beispielsweise mit Diphenylphosphorylazid (DPPA) in Gegenwart von tert-Butanol direkt zu Verbindungen der Formel (I-o) reagieren. Here, the compounds of the formula (I-k) can react, for example, with diphenylphosphoryl azide (DPPA) in the presence of tert-butanol directly to compounds of the formula (I-o).
Aus den Verbindungen der Formel (I-o) lassen sich die Verbindungen der Formeln (I-p) durch N- Alkylierung in einem ersten Reaktionsschritt, N-Deblockierung (d.h. Abspaltung der Boc-Gruppe) in einem zweiten Reaktionsschritt und nachfolgende N-Acylierung in einem dritten Reaktionsschritt erhalten. From the compounds of the formula (Io), the compounds of the formulas (Ip) can be obtained by N-alkylation in a first reaction step, N-deblocking (ie cleavage of the Boc group) in a second reaction step and subsequent N-acylation in a third reaction step receive.
Die Verbindungen der Formel (I-q) können mittels N-Deblockierung (d.h. Abspaltung der Boc-Gruppe) in einem ersten Reaktionsschritt und nachfolgende N-Acylierung in einem zweiten Reaktionsschritt hergestellt werden. Im Allgemeinen können für die Entfernung der Schutzgruppe saure oder basische Reaktionshilfsmittel nach literaturbekannter Verfahrensweise verwendet werden. Bei Verwendung von Schutzgruppen des Carbamat-Typs werden bevorzugt saure Reaktionshilfsmittel verwendet. Bei Verwendung der tert- Butylcarbamat-Schutzgruppe (Boc-Gruppe) werden beispielsweise Mischungen von Mineralsäuren wie Salzsäure, Bromwasserstoffsäure, Salpetersäure, Schwefelsäure, Phosphorsäure oder von organischen Säuren wie Benzoesäure, Ameisensäure, Essigsäure, Trifluoressigsäure, Methansulfonsäure, Benzolsulfonsäure oder Toluolsulfonsäure in einem geeigneten Verdünnungsmittel wie Wasser und/oder einem organischen Lösungsmittel wie Tetrahydrofuran, Dioxan, Dichlormethan, Chloroform, Essigester, Ethanol oder Methanol verwendet. Bevorzugt sind Mischungen von Salzsäure oder Essigsäure mit Wasser und/oder einem organischen Lösungsmittel wie Essigester. Alternativ zu Methode Hl können die Verbindungen der Typen I-p bzw. I-q auch aus nach Methode A synthetisierten Verbindungen durch die im Folgenden beschriebene Methode H2 hergestellt werden: The compounds of the formula (Iq) can be prepared by N-deblocking (ie cleavage of the Boc group) in a first reaction step and subsequent N-acylation in a second reaction step. In general, acidic or basic reaction auxiliaries can be used according to the literature procedure for the removal of the protective group. When using carbamate-type protecting groups, preference is given to using acidic reaction auxiliaries. When using the tert-butylcarbamate protective group (Boc group), for example, mixtures of mineral acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid or of organic acids such as benzoic acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, Benzenesulfonic acid or toluenesulfonic acid in a suitable diluent such as water and / or an organic solvent such as tetrahydrofuran, dioxane, dichloromethane, chloroform, ethyl acetate, ethanol or methanol. Preference is given to mixtures of hydrochloric acid or acetic acid with water and / or an organic solvent such as ethyl acetate. As an alternative to method H1, the compounds of the types Ip or Iq can also be prepared from compounds synthesized according to method A by the method H2 described below:
Reaktionsschema V - Methode H2: Reaction scheme V - method H2:
RM = Reduktionsmittel, z. B. Fe, Zn, Sn(ll), Natriumcyanoborhydrid, Wasserstoff an Pd/C etc. LG = Leaving group, z. B. Halogen or OH Methode H2: Nach Methode A hergestellte Verbindungen, in denen R2 für Nitro steht (I-r), können durch Reduktion der Nitrogruppe nach literaturbekannten Methoden in die entsprechenden Aminoverbindungen (I-s) überführt werden (vgl. z. B. WO2009/14674 AI, 2009 für die Reduktion durch Fe(0); US2005/197331 AI, 2005 für die Reduktion durch Sn(II)C12; WO2007/86800 AI, 2007 für die Reduktion durch Natriumcyanoborhydrid). Diese lassen sich durch Acylierung und ggf. nachfolgende Alkylierung nach literaturbekannten Methoden zu den erfindungsgemäßen Verbindungen des Typs (I-q) bzw. (I-p) umsetzen. Methode I - Allgemeine Verfahren für die Oxidation von Thioethern zu Sulfoxiden und Sulfonen RM = reducing agent, z. Fe, Zn, Sn (II), sodium cyanoborohydride, hydrogen on Pd / C, etc. LG = Leaving group, e.g. B. Halogen or OH Method H2: Compounds prepared according to Method A in which R 2 is nitro (Ir) can be converted into the corresponding amino compounds (Is) by reduction of the nitro group by methods known from the literature (cf., for example, WO2009 / 14674 AI, 2009 for reduction by Fe (0); US2005 / 197331 AI, 2005 for reduction by Sn (II) C12; WO2007 / 86800 AI, 2007 for reduction by sodium cyanoborohydride). These can be converted by acylation and optionally subsequent alkylation by methods known from the literature to the compounds of the type (Iq) or (Ip) according to the invention. Method I - General procedures for the oxidation of thioethers to sulfoxides and sulfones
Verbindungen der Formel (I), in welchen W für SO (Sulfoxide) oder SO2 (Sulfone) steht lassen sich durch Oxidation nach literaturbekannten Verfahren aus Verbindungen der Formel (I), in welchen W für S (Thioethern) steht, herstellen, beispielsweise durch ein Oxidationsmittel in einem geeigneten Lösungs- bzw. Verdünnungsmittel. Als Oxidationsmittel eignen sich zum Beispiel verdünnte Salpetersäure, Wasserstoffperoxid, Oxone® und Peroxycarbonsäuren, wie etwa wefa-Chlorperbenzoesäure. Als Lösungsmittel bzw. Verdünnungsmittel eignen sich inerte organische Lösungsmittel, typischerweise Acetonitril und halogenierte Lösungsmittel wie Dichlormethan, Chloroform oder Dichlorethan, sowie Wasser und Alkohole wie Methanol für die Reaktion mit Oxone®. Möglich ist auch die Einführung geeigneter Aniline R'-NF oder Boronsäuren R1-B(OH)2, in welchen W für SO oder SO2 steht, nach Verfahren D Dbzw. D. Diese lassen sich aus den entsprechenden Vorstufen, in denen W für S steht, nach literaturbekannten Verfahren oxidieren, wie zum Beispiel in WO 2013/092350 beschrieben. Compounds of the formula (I) in which W is SO (sulfoxides) or SO 2 (sulfones) can be prepared by oxidation by literature methods from compounds of the formula (I) in which W is S (thioethers), for example by an oxidizing agent in a suitable solvent or diluent. Suitable oxidizing agents are, for example, dilute nitric acid, hydrogen peroxide, Oxone® and peroxycarboxylic acids, such as wefa-chloroperbenzoic acid. Suitable solvents or diluents are inert organic solvents, typically acetonitrile and halogenated solvents such as dichloromethane, chloroform or dichloroethane, and water and alcohols such as methanol for the reaction with Oxone®. Also possible is the introduction of suitable anilines R'-NF or boronic acids R 1 -B (OH) 2, in which W is SO or SO 2 , according to method D Dbzw. D. These can be oxidized from the corresponding precursors in which W is S, according to literature methods, as described for example in WO 2013/092350.
Zur Erzeugung enantiomeren angereicherter Sulfoxide eignen sich eine Vielfalt von Methoden, wie von G. E. O'Mahony et al, in ARKIVOC (Gainesville, FL, United states), 2011, 1, 1-110, beschrieben: Metall-katalysierte asymmetrische Oxidationen von Thioethern, zum Beispiel mit Titanium oder Vanadium als meistbenutzten Katalysatorquellen, in Form von Ti(0'Pr4) oderVO(acac)2, zusammen mit einem chiralen Liganden und einem Oxidationsmittel wie tert-Butylwasserstoffperoxid (TBHP), 2- Phenylpropan-2-ylhydroperoxid (CHP) oder Wasserstoffperoxid; nicht-metall katalysierte asymmetrische Oxidationen durch Verwendung von chiralen Oxidationsmitteln oder chiralen Katalysatoren; elektrochemische oder biologische asymmetrische Oxidationen sowie kinetische Resolution von Sulfoxiden und nukleophilische Versetzung (nach Andersens Methode). Enantiomerically enriched sulfoxides can be prepared by a variety of methods as described by GE O'Mahony et al in ARKIVOC (Gainesville, FL, United states), 2011, 1, 1-110: metal-catalyzed asymmetric oxidations of thioethers, for example, with titanium or vanadium as the most commonly used catalyst sources, in the form of Ti (0'Pr4) or VO (acac) 2, together with a chiral ligand and an oxidizing agent such as tert-butyl hydrogen peroxide (TBHP), 2-phenylpropan-2-yl hydroperoxide (CHP ) or hydrogen peroxide; non-metal catalyzed asymmetric oxidations by using chiral oxidants or chiral catalysts; electrochemical or biological asymmetric oxidation as well as kinetic resolution of sulfoxides and nucleophilic displacement (according to Andersen's method).
Die Enantiomere können auch aus dem Racemat gewonnen werden, beispielsweise durch präparative Trennung mittels einer chiralen HPLC. Mit den oben beschriebenen Herstellungsverfahren können auch diejenigen Verbindungen in der Tabelle 1 hergestellt werden, die nicht unter die Formel (I) fallen. The enantiomers can also be obtained from the racemate, for example by preparative separation by means of a chiral HPLC. With the production methods described above, it is also possible to prepare those compounds in Table 1 which do not fall under the formula (I).
Wenn im Folgenden von Verbindungen der Formel (I) die Rede ist, sind auch immer diejenigen Verbindungen in der Tabelle 1 eingeschlossen, die nicht unter die Formel (I) fallen. Whenever compounds of the formula (I) are mentioned below, those compounds which are not included in the formula (I) are also included in Table 1.
Isomere Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereomere, Atropisomere oder geometrische Isomere. Die Erfindung umfasst somit reine Stereo-isomere als auch beliebige Gemische dieser Isomere. Isomers Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, Diastereomers, atropisomers or geometric isomers. The invention thus comprises pure stereoisomers as well as any mixtures of these isomers.
Verfahren und Verwendungen Methods and uses
Die Erfindung betrifft auch Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der Formel (I) auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt. Bevorzugt wird die Bekämpfung der tierischen Schädlinge in der Land- und Forstwirtschaft und im Materialschutz durchgeführt. Hierunter vorzugsweise ausgeschlossen sind Verfahren zur chirurgischen oder therapeutischen Behandlung des menschlichen oder tierischen Körpers und Diagnostizierverfahren, die am menschlichen oder tierischen Körper vorgenommen werden. Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. The invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body. The invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel immer auch den Begriff Pflanzenschutzmittel. In the context of the present application, the term pest control always includes the term pesticides.
Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen vor biotischen und abiotischen Stressfaktoren, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, Nematoden und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie können vorzugsweise als Schädlingsbekämpfungsmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören: The compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreation, storage and materials protection and hygiene. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:
Schädlinge aus dem Stamm der Arthropoda, insbesondere aus der Klasse der Arachnida z.B. Acarus spp., z.B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., z.B. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., z.B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., z.B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., z.B. Eutetranychus banksi, Eriophyes spp., z.B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z.B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z.B. Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., z.B. Panonychus citri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., z.B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., z.B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; aus der Klasse der Chilopoda z.B. Geophilus spp., Scutigera spp.; aus der Ordnung oder der Klasse der Collembola z.B. Onychiurus armatus; Sminthurus viridis; aus der Klasse der Diplopoda z.B. Blaniulus guttulatus; aus der Klasse der Insecta, z.B. aus der Ordnung der Blattodea z.B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta spp., z.B. Periplaneta americana, Periplaneta australasiae, Supella longipalpa; aus der Ordnung der Coleoptera z.B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., z.B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., z.B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., z.B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., z.B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., z.B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., z.B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., z.B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., z.B. Curculio caryae, Curculio caryatrypeSjCurculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., z.B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachna spp., z.B. Epilachna borealis, Epilachna varivestis, Epitrix spp., z.B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., z.B. Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp., Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., z.B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z.B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z.B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., z.B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., z.B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., z.B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., z.B. Sternechus paludatus, Symphyletes spp., Tanymecus spp., z.B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., z.B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., z.B. Zabrus tenebrioides; aus der Ordnung der Diptera z.B. Aedes spp., z.B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., z.B. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., z.B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., z.B. Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., z.B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici,Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., z.B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z.B. Dasineura brassicae, Delia spp., z.B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z.B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z.B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., z.B. Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., z.B. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya spp., z.B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., z.B. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., z.B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., z.B. Tipula paludosa, Tipula simplex; aus der Ordnung der Hemiptera z.B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., z.B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., z.B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., z.B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., z.B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., z.B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., z.B. Cacopsylla pyricola, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., z.B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri, Diaspis spp., Drosicha spp., Dysaphis spp., z.B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., z.B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca Solana, Empoasca stevensi, Eriosoma spp., z.B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z.B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z.B. Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., z.B. Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula, Macrosiphum spp., z.B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., z.B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae,. Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., z.B. Nephotettix cinetieeps,, Nephotettix nigropictus, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., z.B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., z.B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., z.B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z.B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., z.B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., z.B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., z.B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., z.B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., z.B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rafiabdominale, Saissetia spp., z.B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis,Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., z.B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., z.B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; aus der Unterordnung der Heteroptera z.B. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z.B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z.B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z.B. Lygocoris pabulinus, Lygus spp., z.B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Monaionion atratum, Nezara spp., z.B. Nezara viridula, Oebalus spp., Piesma quadrata, Piezodorus spp., z.B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; aus der Ordnung der Hymenoptera z.B. Acromyrmex spp., Athalia spp., z.B. Athalia rosae, Atta spp., Diprion spp., z.B. Diprion similis, Hoplocampa spp., z.B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema humile, Monomorium pharaonis, Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., z.B. Vespa crabro, Xeris spp.; aus der Ordnung der Isopoda z.B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; aus der Ordnung der Isoptera z.B. Coptotermes spp., z.B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp., z.B. Reticulitermes flavipes, Reticulitermes hesperus; aus der Ordnung der Lepidoptera z.B. Achroia grisella, Acronicta major, Adoxophyes spp., z.B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., z.B. Agrotis segetum, Agrotis ipsilon, Alabama spp., z.B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z.B. Anticarsia gemmatalis, Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., z.B. Chilo plejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z.B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., z.B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., z.B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., z.B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., z.B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., z.B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., z.B. Leucoptera coffeella, Lithocolletis spp., z.B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z.B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z.b. Lymantria dispar, Lyonetia spp., z.B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., z.B. Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., z.B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z.B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z.B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z.B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z.B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z.B. Schoenobius bipunctifer, Scirpophaga spp., z.B. Scirpophaga innotata, Scotia segetum, Sesamia spp., z.B. Sesamia inferens, Sparganothis spp., Spodoptera spp., z.b. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., z.B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; aus der Ordnung der Orthoptera oder Saltatoria z.B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., z.B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., z.B. Locusta migratoria, Melanoplus spp., z.B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; aus der Ordnung der Phthiraptera z.B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; aus der Ordnung der Psocoptera z.B. Lepinotus spp., Liposcelis spp.; aus der Ordnung der Siphonaptera z.B. Ceratophyllus spp., Ctenocephalides spp., z.B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; aus der Ordnung der Thysanoptera z.B. Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., z.B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., z.B. Thrips palmi, Thrips tabaci; aus der Ordnung der Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; aus der Klasse der Symphyla z.B. Scutigerella spp., z.B. Scutigerella immaculata; Pests of the genus Arthropoda, in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eotetranychus hicoriae , Epitrimerus pyri, Eutetranychus spp., Eg Eutetranychus banksi, Eriophyes spp., Eg Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Eg Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp. , Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Eg Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., Eg Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., Eg Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., Eg Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani , Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the genus of Chilopoda, for example Geophilus spp., Scutigera spp .; from the order or class of Collembola eg Onychiurus armatus; Sminthurus viridis; from the class Diplopoda eg Blaniulus guttulatus; from the class of the Insecta, eg from the order of the Blattodea eg Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta spp., eg Periplaneta americana, Periplaneta australasiae, Supella longipalpa; from the order of the Coleoptera eg Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., eg Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., eg Anthonomus grandis , Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., Eg Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus eg Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., eg Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., eg Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., eg Curculio caryae, Curculio caryatrypeSjCurculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., eg Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachna spp., Eg Epilachna borealis, Epilachna varivestis, Epitrix spp., Eg Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator , Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., Eg Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., eg Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp., Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., eg Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., eg Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, oryzae Oryzaphagus, Otiorhynchus spp., for example, Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., eg Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., eg Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Eg S itophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Starchus spp., eg Starchus paludatus, Symphyletes spp., Tanymecus spp., eg Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus Tribolium spp., Eg Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., Eg Zabrus tenebrioides; from the order of the Diptera eg Aedes spp., eg Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., eg Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., eg Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., eg Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp Contarinia johnsoni, Contarina nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., eg Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp. Dacus oleae, Dasineura spp., Eg, Dasineura brassicae, Delia spp., Eg Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila sp p., eg, Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., eg Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., eg Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., eg Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp , Paralauterborniella subcincta, Pegomya spp., Eg Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., Eg Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., eg Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., eg Tipula paludosa, Tipula simplex; from the order of the Hemiptera eg Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., eg Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., Eg Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., Eg Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., Eg Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines , Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., Eg Aspidiotus nerii, Atanus spp. , Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp. , eg Cacopsylla pyricola, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., eg Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri, Diaspis spp., Drosicha spp., Dysaphis spp., eg Dysaphis apiifolia, Dysaphis plantaginea , Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., Eg Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca Solana, Empoasca stevensi, Eriosoma spp., Eg Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp. Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., Eg Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Eg Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., Eg Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula, Macrosiphum spp., eg Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., eg Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae ,. Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., Eg Nephotettix cinetieeps, Nephotettix nigropictus, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Eg Paratrioza cockerelli, Parlatoria spp. Pemphigus spp., Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., Eg Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp. , Pyrilla spp., Quadraspidiotus spp., Eg Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., eg Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rafiabdominal, Saissetia spp., eg Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., eg Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., Eg Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the suborder of the Heteroptera eg Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., eg Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., eg Eusystus heros, Euschistus servus, Eustistus tristigmus, Eushtistus variolarius, Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocoris varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., Eg Lygocoris pabulinus, Lygus spp., Eg Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Monaionion atratum, Nezara spp., Eg Nezara viridula, Oebalus Spp., Piesma quadrata, Piezodorus spp., eg, Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nas hi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera eg Acromyrmex spp., Athalia spp., eg Athalia rosae, Atta spp., Diprion spp., eg Diprion similis, Hoplocampa spp., eg Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema humile, Monomorium pharaonis , Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., Eg Vespa crabro, Xeris spp .; from the order of Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera eg Coptotermes spp., eg Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp., eg Reticulitermes flavipes, Reticulitermes hesperus; from the order of the Lepidoptera eg Achroia grisella, Acronica major, Adoxophyes spp., eg Adoxophyes orana, Aedia leucomelas, Agrotis spp., eg Agrotis segetum, Agrotis ipsilon, Alabama spp., eg Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., eg Anticarsia gemmatalis, Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus pinarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp. eg, Chilo plejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., Eg Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp. eg Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., eg Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp Helicoverpa spp., eg Helicoverpa armigera, Helicoverpa zea, Heliothis spp., eg Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp , Leucinodes orbonalis, Leucoptera spp., Eg Leucoptera coffeella, Lithocolletis spp., Eg Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Eg Lobesia botrana, Loxagrotis albicosta, Lymantria spp. , eg Lymantria dispar, Lyonetia spp., eg, Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp. Orthaga spp., Ostrinia spp., Eg Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., Eg Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Eg Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp ., eg Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., eg Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp. eg Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., eg Schoenobius bipunctifer, Scirpophaga spp., eg Scirpophaga innotata, Scotia segetum, Sesamia spp., eg Sesamia infe Spartoptera spp., Spodoptera spp., Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., eg Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .; from the order of Orthoptera or Saltatoria eg Acheta domesticus, Dichroplus spp., Gryllotalpa spp., eg Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., eg Locusta migratoria, Melanoplus spp., eg Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera eg Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of Psocoptera eg Lepinotus spp., Liposcelis spp .; from the order of Siphonaptera eg Ceratophyllus spp., Ctenocephalides spp., eg Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera eg Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., eg Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus , Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., Eg Thrips palmi, Thrips tabaci; from the order of Zygentoma (= Thysanura), z. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
Schädlinge aus dem Stamm der Mollusca, insbesondere aus der Klasse der Bivalvia, z.B. Dreissena spp.; sowie aus der Klasse der Gastropoda z.B. Arion spp., z.B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., z.B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Pests of the Mollusca strain, in particular of the bivalve class, e.g. Dreissena spp .; and from the class of Gastropoda e.g. Arion spp., E.g. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
Tier- und Humanparasiten aus den Stämmen der Platyhelminthes und Nematoda, z.B. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp.; Animal and human parasites from the strains of Platyhelminthes and Nematoda, e.g. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp. , Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp. , Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria sp Paraglia spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp. , Strongyloides spp., Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp .;
Pflanzenschädlinge aus dem Stamm der Nematoda, d.h. pflanzenparasitäre Nematoden, insbesondere Aglenchus spp., z.B. Aglenchus agricola, Anguina spp., z.B. Anguina tritici, Aphelenchoides spp., z.B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., z.B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., z.B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., z.B. Cacopaurus pestis, Criconemella spp., z.B. Criconemella curvata, Criconemella onoensis, Criconemella omata, Criconemella rasium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., z.B. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., z.B. Ditylenchus dipsaci, Dolichodoras spp., Globodera spp., z.B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., z.B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., z.B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorus spp., z.B. Longidorus africanus, Meloidogyne spp., z.B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paraphelenchus spp., Paratrichodorus spp., z.B. Paratrichodorus minor, Pratylenchus spp., z.B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., z.B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., z.B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., z.B. Tylenchorhynchus annulatus, Tylenchulus spp., z.B. Tylenchulus semipenetrans, Xiphinema spp., z.B. Xiphinema index. Weiterhin lässt sich aus dem Unterreich der Protozoa die Ordnung der Coccidia z.B. Eimeria spp. bekämpfen. Plant pests from the Nematoda strain, ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Eg Cacopaurus pestis, Criconemella spp., eg Criconemella curvata, Criconemella onoensis, Criconemella omata, Criconemella rasium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., eg Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., eg Ditylenchus dipsaci, Dolichodoras spp., Globodera spp., eg Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., eg Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., eg Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorus spp , eg Longidorus africanus, Meloidogyne spp., eg Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paraphelenchus spp., Paratrichodorus spp., eg Paratrichodorus minor, Pratylenchus spp. , eg Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., eg Radopholus c itrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., eg Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., eg Tylenchorhynchus annulatus, Tylenchulus spp., eg Tylenchulus semipenetrans, Xiphinema spp ., eg Xiphinema index. Furthermore, the order of the coccidia, eg Eimeria spp., Can be determined from the sub-region of the protozoa. fight.
Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, als Mikrobizide oder Gametozide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasma- like-organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen. The compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as a remedy for MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
Formulierungen formulations
Die vorliegende Erfindung betrifft weiterhin Formulierungen und daraus bereitete Anwendungsformen als Schädlingsbekämpfungsmittel wie z. B. Drench-, Drip- und Spritzbrühen, umfassend mindestens eine Verbindung der Formel (I). Gegebenenfalls enthalten die Anwendungsformen weitere Schädlingsbekämpfungsmittel und/oder die Wirkung verbessernde Adjuvantien wie Penetrationsforderer, z. B. vegetative Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester vegetativer Fettsäuren wie beispielsweise Rapsöl- oder Sojaölmethylester oder Alkanol-alkoxylate und/oder Spreitmittel wie beispielsweise Alkylsiloxane und/oder Salze z.B. organische oder anorganische Ammonium- oder Phosphoniumsalze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat und/oder die Retention fordernde Mittel wie z. B. Dioctylsulfosuccinat oder Hydroxypropyl-guar Polymere und/oder Humectants wie z.B. Glycerin und/oder Dünger wie beispielsweise Ammonium-, Kalium- oder Phosphor-enthaltende Dünger. Übliche Formulierungen sind beispielsweise wasserlösliche Flüssigkeiten (SL), Emulsionskonzentrate (EC), Emulsionen in Wasser (EW), Suspensionskonzentrate (SC, SE, FS, OD), in Wasser dispergierbare Granulate (WG), Granulate (GR) und Kapselkonzentrate (CS); diese und weitere mögliche Formuliertypen sind beispielsweise durch Crop Life International und in Pesticide Speciiications, Manual on development and use of FAO and WHO speciiications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO/WHO Joint Meeting on Pesticide Speciiications, 2004, ISBN: 9251048576 beschrieben. Gegebenenfalls enthalten die Formulierungen neben einem oder mehreren Verbindungen der Formel (I) weitere agrochemische Wirkstoffe. The present invention further relates to formulations and application forms prepared therefrom as pesticides such. B. drench, drip and spray liquors, comprising at least one compound of formula (I). Optionally, the use forms contain other pesticides and / or the effect of improving adjuvants such as Penetrationsforderer, z. As vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetable fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts such as organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-demanding agents such as. As dioctylsulfosuccinate or hydroxypropyl guar polymers and / or humectants such as glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer. Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ; These and other possible formulation types are described, for example, by Crop Life International and in Pesticide Speci fi cations, Manual on development and use of FAO and WHO speci fi cations for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Speci fi cations, 2004, ISBN: 9251048576. If appropriate, the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitätsförderer, Trägerstoffe, Emulgiermittel, Dispergiermittel, Frostschutzmittel, Biozide, Ver dicker und/oder weitere Hilfsstoffe wie beispielsweise Adjuvantien enthalten. Ein Adjuvant in diesem Kontext ist eine Komponente, die die biologische Wirkung der Formulierung verbessert, ohne dass die Komponente selbst eine biologische Wirkung hat. Beispiele für Adjuvantien sind Mittel, die die Retention, das Spreitverhalten, das Anhaften an der Blattoberfläche oder die Penetration fördern. Preferably, they are formulations or application forms which contain adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants. An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect. Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Verbindungen der Formel (I) mit Hilfsstoffen wie beispielsweise Streckmitteln, Lösemitteln und/oder festen Trägerstoffen und/oder weiteren Hilfsstoffen wie beispielsweise oberflächenaktive Stoffe. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. These formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances. The preparation of the formulations is carried out either in suitable systems or before or during use.
Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, der Formulierung der Verbindungen der Formel (I) oder den aus diesen Formulierungen bereiteten Anwendungsformen (wie z.B. gebrauchsfähigen Schädlingsbekämpfungsmitteln wie Spritzbrühen oder Saatgutbeizen) besondere Eigenschaften, wie bestimmte physikalische, technische und/oder biologische Eigenschaften zu verleihen. Excipients which can be used are those which are suitable for the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or biological properties To give properties.
Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N- Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsulfoxid). As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfslösemittel verwendet werden. Als flüssige Lösemittel kommen im Wesentlichen infrage: Aromaten wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasser-stoffe wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser. In the case of the use of water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic Hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Grundsätzlich können alle geeigneten Lösemittel verwendet werden. Geeignete Lösemittel sind beispielsweise aromatische Kohlenwasserstoffe wie z.B. Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische oder aliphatische Kohlenwasserstoffe wie z.B. Chlorbenzol, Chlorethylen, oder Methylenchlorid, aliphatische Kohlenwasserstoffe wie z.B. Cyclohexan, Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie z.B. Methanol, Ethanol, iso-Propanol, Butanol oder Glykol sowie deren Ether und Ester, Ketone wie z.B. Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylsulfoxid sowie Wasser. In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g. Cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
Grundsätzlich können alle geeigneten Trägerstoffe eingesetzt werden. Als Trägerstoffe kommen insbesondere infrage: z.B. Ammoniumsalze und natürliche Gesteinsmehle wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehl, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse und /oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls verwendet werden. Als Trägerstoffe für Granulate kommen infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Papier, Kokosnussschalen, Maiskolben und Tabakstängel. In principle, all suitable carriers can be used. Suitable carriers are, in particular: Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Suitable carriers for granules are: e.g. Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
Auch verflüssigte gasförmige Streckmittel oder Lösemittel können eingesetzt werden. Insbesondere eignen sich solche Streckmittel oder Trägerstoffe, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid. Also, liquefied gaseous diluents or solvents can be used. Particularly suitable are those diluents or carriers which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
Beispiele für Emulgier- und/oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe sind Salze von Polyacrylsäure, Salze von Lignosulphonsäure, Salze von Phenolsulphonsäure oder Naphthalinsulphonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulphobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenole, Fettsäureester von Polyolen und Derivate der Verbindungen enthaltend Sulphate, Sulphonate und Phosphate, z.B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate, Eiweißhydrolysate, Lignin-Sulfitablaugen und Methylcellulose. Die Anwesenheit einer oberflächenaktiven Substanz ist vorteilhaft, wenn eine der Verbindungen der Formel (I) und/oder einer der inerten Trägerstoffe nicht in Wasser löslich ist und wenn die Anwendung in Wasser erfolgt. Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates , Arylsulfonates, protein hydrolysates, lignin-sulphite liquors and methylcellulose. The presence of a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.
Als weitere Hilfsstoffe können in den Formulierungen und den daraus abgeleiteten Anwendungsformen Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Nähr- und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink vorhanden sein. As further adjuvants, in the formulations and the applications derived therefrom, dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Konservierungsmittel, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel. Weiterhin enthalten sein können schaumerzeugende Mittel oder Entschäumer. Ferner können die Formulierungen und daraus abgeleiteten Anwendungsformen als zusätzliche Hilfsstoffe auch Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere enthalten wie Gummiarabikum, Polyvinylalkohol, Polyvinylacetat sowie natürliche Phospholipide wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Hilfsstoffe können mineralische und vegetabile Öle sein. Gegebenenfalls können noch weitere Hilfsstoffe in den Formulierungen und den daraus abgeleiteten Anwendungsformen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsförderer, Stabilisatoren, Sequestiermittel, Komplexbildner, Humectans, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) mit jedem festen oder flüssigen Zusatzstoff, welches für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers. In addition, the formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other auxiliaries may be mineral and vegetable oils. Optionally, further auxiliaries may be present in the formulations and in the use forms derived therefrom. Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
Als Retentionsförderer kommen alle diejenigen Substanzen in Betracht, die die dynamische Oberflächenspannung verringern wie beispielsweise Dioctylsulfosuccinat oder die die Visko-Elastizität erhöhen wie beispielsweise Hydroxypropyl-guar Polymere. As retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
Als Penetrationsförderer kommen im vorliegenden Zusammenhang alle diejenigen Substanzen in Be- tracht, die üblicherweise eingesetzt werden, um das Eindringen von agrochemischen Wirkstoffen in Pflanzen zu verbessern. Penetrationsförderer werden in diesem Zusammenhang dadurch definiert, dass sie aus der (in der Regel wässerigen) Applikationsbrühe und/oder aus dem Spritzbelag in die Kutikula der Pflanze eindringen und dadurch die Stoffbeweglichkeit (Mobilität) der Wirkstoffe in der Kutikula erhöhen können. Die in der Literatur (Baur et al., 1997, Pesticide Science 51, 131-152) beschriebene Methode kann zur Bestimmung dieser Eigenschaft eingesetzt werden. Beispielhaft werden genannt Alkoholalkoxylate wie beispielsweise Kokosfettethoxylat (10) oder Isotridecylethoxylat (12), Fettsäureester wie beispielsweise Rapsöl- oder Sojaölmethylester, Fettamine Alkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium-Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat. Penetration promoters in the present context include all those substances which are usually used to improve the penetration of agrochemical active substances into plants. Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as for example Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
Die Formulierungen enthalten bevorzugt zwischen 0,00000001 und 98 Gew.-% der Verbindung der Formel (I), besonders bevorzugt zwischen 0,01 und 95 Gew.-% der Verbindung der Formel (I), ganz besonders bevorzugt zwischen 0,5 und 90 Gew.-% der Verbindung der Formel (I), bezogen auf das Gewicht der Formulierung. The formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.
Der Gehalt an der Verbindung der Formel (I) in den aus den Formulierungen bereiteten Anwendungsformen (insbesondere Schädlingsbekämpfungsmittel) kann in weiten Bereichen variieren. Die Konzentration der Verbindung der Formel (I) in den Anwendungsformen kann üblicherweise zwischen 0,00000001 und 95 Gew.-% der Verbindung der Formel (I), vorzugsweise zwischen 0,00001 und 1 Gew.-%, bezogen auf das Gewicht der Anwendungsform, liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise. The content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges. The concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie. The application is done in a custom forms adapted to the application.
Mischungen mixtures
Die Verbindungen der Formel (I) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden, Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika, Nützlingen, Herbizide, Düngemitteln, Vogelrepellentien, Phytotonics, Sterilantien, Safenern, Semiochemicals und/oder Pflanzenwachstumsregulatoren verwendet werden, um so z.B. das Wirkungsspektrum zu verbreitern, die Wirkdauer zu verlängern, die Wirkgeschwindigkeit zu steigern, Repellenz zu verhindern oder Resistenzentwicklungen vorzubeugen. Desweiteren können solche Wirkstoffkombinationen das Pflanzenwachstum und/oder die Toleranz gegenüber abiotischen Faktoren wie z. B. hohen oder niedrigen Temperaturen, gegen Trockenheit oder gegen erhöhten Wasser- bzw. Bodensalzgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfähigkeit und Bewurzelung optimieren, die Ernte erleichtern und Ernteerträge steigern, die Reife beeinflussen, die Qualität und/oder den Ernährungswert der Ernteprodukte steigern, die Lagerfähigkeit verlängern und/oder die Bearbeitbarkeit der Ernteprodukte verbessern. The compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be, for example to widen the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-exposure or to prevent the development of resistance. Furthermore, such drug combinations plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt. Also, flowering and fruiting behavior can be improved, germination and rooting can be improved, harvesting and crop yields increased, maturity can be enhanced, crop quality and / or nutritional value increased, shelf life extended and / or crop productivity improved.
Weiterhin können die Verbindungen der Formel (I) in Mischung mit weiteren Wirkstoffen oder Semiochemicals, wie Lockstoffen und/oder Vogelrepellentien und/oder Pflanzenaktivatoren und/oder Wachstumsregulatoren und/oder Düngemitteln vorliegen. Gleichfalls können die Verbindungen der Formel (I) in Mischungen mit Mitteln zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden. Furthermore, the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
In einer besonderen erfindungsgemäßen Ausführungsform liegen die Verbindungen der Formel (I) in Formulierungen bzw. in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit weiteren Verbindungen vor, vorzugsweise solchen wie nachstehend beschrieben. Wenn eine der im Folgenden genannten Verbindungen in verschiedenen tautomeren Formen vorkommen kann sind auch diese Formen mit umfasst, auch wenn sie sie nicht in jedem Fall explizit genannt wurden. In a particular embodiment of the invention, the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below. If one of the following compounds can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case.
Insektizide / Akarizide / Nematizide Die hier mit ihrem „common name" genannten Wirkstoffe sind bekannt und beispielsweise im Pestizidhandbuch („The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) beschrieben oder im Internet recherchierbar (z.B. http://www.alanwood.net/pesticides). Insecticides / Acaricides / Nematicides The active substances mentioned here with their "common name" are known and described, for example, in the Pesticide Handbook ("The Pesticide Manual" 16th ed., British Crop Protection Council 2012) or searchable on the Internet (eg http: // www. alanwood.net/pesticides).
(1) Acetylcholinesterase (AChE) Inhibitoren, wie beispielsweise Carbamate, z.B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder organophosphate, z.B. Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl 0-(methoxyaminothio- phosphoryl) salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. (1) Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and Xylylcarb or organophosphates, eg Acephate, Azamethiphos, Azinophos-ethyl, Azinophos-methyl, Cadusafos, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinone, Dichlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Disulfone, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O- (methoxyaminothiophosphoryl) salicylate, Isoxathione, Malathion, Mecarbam, Methamidophos, Methidathione, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, triclorfone and vamidothion.
(2) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Cyclodien-organochlorine, z.B. Chlordane und Endosulfan oder Phenylpyrazole (Fiprole), z.B. Ethiprole und Fipronil. (2) GABA-controlled chloride channel antagonists, such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
(3) Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker, wie beispielsweise Pyrethroide, z.B. Acrinathrin, Allethrin, d-cis-trans Allethrin, d-trans Allethrin, Bifenthrin, Bioallethrin,(3) sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. Acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin,
Bioallethrin S-cyclopentenyl Isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta- Cypermethrin, theta-Cypermethrin, zeta-Cypermethrin, Cyphenothrin [(lR)-trans-Isomere], Deltamethrin, Empenthrin [(EZ)-(lR)-Isomere), Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [(lR)-trans-Isomer), Prallethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)- Isomere)], Tralomethrin und Transfluthrin oder DDT oder Methoxychlor. (4) Nikotinerge Acetylcholin-Rezeptor (nAChR) Agonisten, wie beispielsweise Neonikotinoide, z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nikotin oder Sulfoxaflor oder Flupyradifurone. Bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, flumethrin, tau-fluvalinates, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(lR) - trans isomer), prallethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) - isomers)], tralomethrin and transfluthrin or DDT or methoxychlor. (4) nicotinergic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, eg acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
(5) Nikotinerge Acetylcholin-Rezeptor (nAChR) allosterische Aktivatoren, wie beispielsweise Spinosine, z.B. Spinetoram und Spinosad. (5) nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
(6) Chlorid-Kanal-Aktivatoren, wie beispielsweise Avermectine/Milbemycine, z.B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (6) chloride channel activators, such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
(7) Juvenilhormon-Imitatoren, wie beispielsweise Juvenilhormon- Analoge, z.B. Hydroprene, Kinoprene und Methoprene oder Fenoxycarb oder Pyriproxyfen. (8) Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, wie beispielsweise (7) Juvenile hormone mimics, such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen. (8) agents with unknown or non-specific mechanisms of action, such as
Alkylhalide, z.B. Methylbromid und andere Alkylhalide; oderChloropicrin oder Sulfurylfluorid oder Borax oder Brechweinstein. Alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
(9) Selektive Fraßhemmer, z.B. Pymetrozine oder Flonicamid. (9) Selective feeding inhibitors, e.g. Pymetrozine or flonicamide.
(10) Milbenwachstumsinhibitoren, z.B. Clofentezine, Hexythiazox und Diflovidazin oder Etoxazole. (11) Mikrobielle Disruptoren der Insektendarmmembran, z.B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und BT Pflanzenproteine: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl . (10) mite growth inhibitors, e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole. (11) Insect intestinal membrane microbial disruptors, e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
(12) Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren, wie beispielsweise Diafenthiuron oder Organozinnverbindungen, z.B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder Propargite oder(12) oxidative phosphorylation inhibitors, ATP disruptors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and fenbutatin oxide or propargite or
Tetradifon. Tetradifon.
(13) Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten, wie beispielsweise Chlorfenapyr, DNOC und Sulfluramid. (13) Decoupling of oxidative phosphorylation by interruption of the H proton gradient, such as chlorfenapyr, DNOC, and sulfluramide.
(14) Nikotinerge Acetylcholin-Rezeptor-Antagonisten, wie beispielsweise Bensultap, Cartap- hydrochlorid, Thiocyclam und Thiosultap-Natrium. (14) Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, Thiocyclam and Thiosultap sodium.
(15) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. (15) Type 0 inhibitors of chitin biosynthesis, such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
(16) Inhibitoren der Chitinbiosynthese, Typ 1, wie beispielsweise Buprofezin. (17) Häutungshemmer (insbesondere bei Dipteren, d.h.Zweiflüglern), wie beispielsweise Cyromazine. (16) inhibitors of chitin biosynthesis, type 1, such as buprofezin. (17) Moulting inhibitors (especially in dipterans, ie tails), such as Cyromazine.
(18) Ecdyson-Rezeptor Agonisten, wie beispielsweise Chromafenozide, Halofenozide, Methoxyfenozide und Tebufenozide. (18) ecdysone receptor agonists, such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
(19) Oktopaminerge Agonisten, wie beispielsweise Amitraz. (20) Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon oder Acequinocyl oder Fluacrypyrim. (19) Octopaminergic agonists, such as amitraz. (20) Complex III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.
(21) Komplex-I-Elektronentransportinhibitoren, beispielsweise METI-Akarizide, z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Rotenone (Derris). (21) complex I electron transport inhibitors, for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
(22) Spannungsabhängige Natriumkanal-Blocker, z.B. Indoxacarb oder Metaflumizone. (23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z.B. Spirodiclofen, Spiromesifen und Spirotetramat. (22) voltage dependent sodium channel blockers, e.g. Indoxacarb or metaflumizone. (23) inhibitors of acetyl-CoA carboxylase, such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
(24) Komplex-IV-Elektronentransportinhibitoren, wie beispielsweise Phosphine, z.B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanid. (24) complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.
(25) Komplex-II-Elektronentransportinhibitoren, wie beispielsweise Cyenopyrafen und Cyflumetofen. (28) Ryanodinrezeptor-Effektoren, wie beispielsweise Diamide, z.B. Chlorantraniliprole, Cyantraniliprole und Flubendiamide. (25) Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen. (28) ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide.
Weitere Wirkstoffe mit unbekanntem oder nicht eindeutigem Wirkmechanismus, wie beispielsweise Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide Dicloromezotiaz, Dicofol, Diflovidazin, Flometoquin, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Meperfluthrin, Paichongding, Pyflubumide, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tioxazafen, Triflumezopyrim und Iodmethan; desweiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo) , sowie folgende bekannte wirksame Verbindungen: l- {2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}-3-(trifluormethyl)-lH- l,2,4-triazol-5-amin (bekannt aus WO2006/043635), {l'-[(2E)-3-(4-Chlorphenyl)prop-2-en-l-yl]-5- fluorspiro[indol-3,4'-piperidin]-l(2H)-yl}(2-chlorpyridin-4-yl)methanon (bekannt ausOther drugs with unknown or ambiguous mechanism of action, such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolites, cyclaniliprole, cycloxapride, cyhalodiamide dicloromezotiaz, dicofol, diflovidazine, flometoquine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, Flaxxafon, Fluopyram, Fluralaner, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Meperfluthrin, Paichongding, Pyflubumide, Pyralidyl, Pyrifluquinazone, Pyriminostrobin, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tioxazafen, Triflumezopyrim and Iodomethane; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following known active compounds: 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -3- (trifluoromethyl) -1H-l, 2,4-triazol-5-amine (known from WO2006 / 043635), {1 '- [(2E) -3- (4-chlorophenyl) prop-2-ene l-yl] -5-fluorospiro [indole-3,4'-piperidin] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone (known from
WO2003/106457), 2-Chlor-N-[2- { 1 -[(2E)-3-(4-chlorphenyl)prop-2-en- 1 -yl]piperidin-4-yl} -4-WO2003 / 106457), 2-chloro-N- [2- {1 - [(2E) -3- (4-chlorophenyl) -prop-2-en-1-yl] -piperidin-4-yl} -4-
(trifluormethyl)phenyl]isonicotinamid (bekannt aus WO2006/003494), 3-(2,5-Dimethylphenyl)-4- hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO2009/049851), 3-(2,5- Dimethylphenyl)-8-methoxy-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus WO2009/049851), 4-(But-2 n -yloxy)-6-(3,5-dimethylpiperidin-l -yl)-5-fluorpyrimidin (bekannt aus WO2004/099160), 4-(But-2-in-l -yloxy)-6-(3-chlorphenyl)pyrimidin (bekannt aus WO2003/076415), PF1364 (CAS-Reg.No. 1204776-60-2), Methyl-2-[2-({[3-brom-l-(3-chlorpyridin-2-yl)-lH-pyrazol-5- yljcarbonyl} amino)-5-chlor-3-methylbenzoyl]-2-methylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2-[2-({[3-brom-l-(3-chlorpyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)-5- cyan-3-methylbenzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2-[2-({[3- brom-l-(3-chlorpyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl]-2- methylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2-[3,5-dibrom-2-({[3-brom-l -(3- chlorpyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005/085216), N-[2-(5-Amino-l,3,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-l -(3- chlorpyridin-2-yl)-lH-pyrazol-5-carboxamid (bekannt aus CN102057925), 8-Chlor-N-[(2-chlor-5- methoxyphenyl)sulfonyl]-6-(trifluormethyl)imidazo[l ,2-a]pyridin-2-carboxamid (bekannt aus WO2010/129500), 4-[5-(3,5-Dichlo^henyl)-5-(trifluormethyl)-4,5-dihydro-l,2-oxazol-3-yl]-2-methyl- N-(l-oxidothietan-3-yl)benzamid (bekannt aus WO2009/080250), N-[(2E)-l-[(6-Chlorpyridin-3- yl)methyl]pyridin-2(lH)-yliden]-2,2,2-trifluoracetamid (bekannt aus WO2012/029672), l-[(2-Chlor-l,3- thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[l,2-a]pyrimidin-l-ium-2-olat (bekannt aus(trifluoromethyl) phenyl] isonicotinamide (known from WO2006 / 003494), 3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] dec-3-en-2-one ( known from WO2009 / 049851), 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l, 8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from WO2009 / 049851), 4- (but-2n-oxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004 / 099160), 4- (but-2-in l -yloxy) -6- (3-chlorophenyl) pyrimidine (known from WO2003 / 076415), PF1364 (CAS Reg. No. 1204776-60-2), methyl 2- [2 - ({[3-bromo- 1- (3-chloropyridin-2-yl) -1H-pyrazol-5-ylcarbonyl} amino) -5-chloro-3-methylbenzoyl] -2-methylhydrazinecarboxylate (known from WO2005 / 085216), methyl 2- [2- ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] -2-ethylhydrazinecarboxylate (known from WO2005 / 085216 ), Methyl 2- [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] - 2-methylhydrazinecarboxylate (known from WO2005 / 085216), methyl 2- [3,5-dibromo-2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl ] carbonyl} amino) benzoyl] -2-ethylhydrazinecarboxylate (known from WO2005 / 085216), N- [2- (5-amino-1, 3,4-thiadiazol-2-yl) -4-chloro-6-methylphenyl] 3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide (known from CN10205792 5), 8-chloro-N - [(2-chloro-5-methoxyphenyl) sulfonyl] -6- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxamide (known from WO2010 / 129500), 4- [5- (3,5-Dichloroyl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2-methyl-N- (1-oxidothietan-3-yl ) benzamide (known from WO2009 / 080250), N - [(2E) -1 - [(6-chloropyridin-3-yl) methyl] pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide (known from WO2012 / 029672), 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidine-1-ol -2-olate (known from
WO2009/099929), l-[(6-Chlorpyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[l,2-a]pyrimidin-l-ium- 2-olat (bekannt aus WO2009/099929), 4-(3- {2,6-Dichlor-4-[(3,3-dichlorprop-2-en-l- yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN101337940), N-[2- (tert-Butylcarbamoyl)-4-chlor-6-methylphen WO2009 / 099929), l - [(6-chloropyridin-3-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [l, 2-a] pyrimidin-1-ium-2-olate (known from WO2009 / 099929), 4- (3- {2,6-dichloro-4 - [(3,3-dichloroprop-2-en-1-yl) oxy] phenoxy} propoxy) -2-methoxy-6- (trifluoromethyl ) pyrimidine (known from CN101337940), N- [2- (tert-butylcarbamoyl) -4-chloro-6-methylphenol
carboxamid (bekannt aus WO2008/134969, 3-[Benzoyl(methyl)amino]-N-[2-brom-4-[l,2,2,2-tetrafluor- l-(trifluormethyl)ethyl]-6-(trifluormethyl)phenyl]-2-fluor-benzamid (bekannt aus WO 2010018714), Butyl-[2-(2,4-dichlorphenyl)-3-oxo-4-oxaspiro[4.5]dec-l-en-l-yl]-carbonat (bekannt aus CN 102060818), 4-[5-(3,5-Dichlorphenyl)-5-(trifluormethyl)-4H-isoxazol-3-yl]-N-[(Z)- methoxyiminomethyl]-2-methyl-benzamid (bekannt aus WO2007/026965), 3E)-3-[l-[(6-Chlor-3- pyridyl)methyl]-2-pyridyliden]-l,l,l-trifluor-propan-2-on (bekannt aus WO2013/144213, N- (Methylsulfonyl)-6-[2-(pyridin-3-yl)-l,3-thiazol-5-yl]pyridin-2-carboxamid (bekannt auscarboxamide (known from WO2008 / 134969, 3- [benzoyl (methyl) amino] -N- [2-bromo-4- [l, 2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] -6- (trifluoromethyl ) phenyl] -2-fluorobenzamide (known from WO 2010018714), butyl [2- (2,4-dichlorophenyl) -3-oxo-4-oxaspiro [4.5] dec-1-en-1-yl] - carbonate (known from CN 102060818), 4- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4H-isoxazol-3-yl] -N - [(Z) -methoxyiminomethyl] -2-methyl- benzamide (known from WO2007 / 026965), 3E) -3- [1- [(6-chloro-3-pyridyl) methyl] -2-pyridylidene] -1,1-trifluoro-propan-2-one (known from WO2013 / 144213, N- (methylsulfonyl) -6- [2- (pyridin-3-yl) -1,3-thiazol-5-yl] pyridine-2-carboxamide (known from
WO2012/000896), N-[3-(Benzylcarbamoyl)-4-chlorphenyl]-l-methyl-3-(pentafluorethyl)-4- (trifluormethyl)-lH-pyrazol-5-carboxamid bekannt aus WO2010/051926). Fungizide WO2012 / 000896), N- [3- (benzylcarbamoyl) -4-chlorophenyl] -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5-carboxamide known from WO2010 / 051926). fungicides
Die hier mit ihrem "common name" spezifizierten Wirkstoffe sind bekannt, beispielsweise beschrieben im "Pesticide Manual" oder im Internet (beispielsweise: http://www.alanwood.net/pesticides). The active ingredients specified here with their "common name" are known, for example, described in the "Pesticide Manual" or on the Internet (for example: http://www.alanwood.net/pesticides).
Alle aufgeführten fungiziden Mischpartner der Klassen (1) bis (15) können optional Salze mit entsprechenden Basen oder Säuren bilden, sofern geeignete funktionelle Gruppen vorliegen. Außerdem sind für die aufgeführten füngiziden Mischpartner der Klassen (1) bis (15) auch tautomere Formen eingeschlossen, sofern Tautomerie möglich ist. All listed fungicidal mixing partners of classes (1) to (15) can optionally form salts with corresponding bases or acids, provided that suitable functional groups are present. Furthermore tautomeric forms are also included for the listed five-membered hybrids of classes (1) to (15), provided that tautomerism is possible.
1) Inhibitoren der Ergosterolbiosynthese, zum Beispiel (1.01) Aldimorph, (1.02) Azaconazol, (1.03) Bitertanol, (1.04) Bromuconazol, (1.05) Cyproconazol, (1.06) Diclobutrazol, (1.07) Difenoconazol, (1.08) Diniconazol, (1.09) Diniconazol-M, (1.10) Dodemorph, (1.11) Dodemorphacetat, (1.12) Epoxiconazol, (1.13) Etaconazol, (1.14) Fenarimol, (1.15) Fenbuconazol, (1.16) Fenhexamid, (1.17) Fenpropidin, (1.18) Fenpropimorph, (1.19) Fluquinconazol, (1.20) Flurprimidol, (1.21) Flusilazol, (1.22) Flutriafol, (1.23) Furconazol, (1.24) Furconazol-cis, (1.25) Hexaconazol, (1.26) Imazalil, (1.27) Imazalilsulfat, (1.28) Imibenconazol, (1.29) Ipconazol, (1.30) Metconazol, (1.31) Myclobutanil, (1.32) Naftifin, (1.33) Nuarimol, (1.34) Oxpoconazol, (1.35) Paclobutrazol, (1.36) Pefurazoat, (1.37) Penconazol, (1.38) Piperalin, (1.39) Prochloraz, (1.40) Propiconazol, (1.41) Prothioconazol, (1.42) Pyributicarb, (1.43) Pyrifenox, (1.44) Quinconazol, (1.45) Simeconazol, (1.46) Spiroxamin, (1.47) Tebuconazol, (1.48) Terbinafin, (1.49) Tetraconazol, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizol, (1.54) Triforin, (1.55) Triticonazol, (1.56) Uniconazol, (1.57) Uniconazol-p, (1.58) Viniconazol, (1.59) Voriconazol, (1.60) l-(4-Chlorphenyl)-2-(lH-l,2,4-triazol-l - yl)cycloheptanol, (1 -61) 1 -(2,2-Dimethyl-2,3 -dihydro- 1 H-inden- 1 -yl)- 1 H-imidazol-5- carbonsäure~Tnethylester, (1.62) N'- {5-(Difluormethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}- N-ethyl-N-methylimidoformamid, (1.63) N-Ethyl-N-methyl-N'- {2-methyl-5-(trifluormethyl)-4-[3- (trimethylsilyl)propoxy]phenyl} imidoformamid, ( 1.64) O- [ 1 -(4-Methoxyphenoxy)-3 ,3 -dimethylbutan-2- yl]-lH-imidazol-l-carbothioat, (1.65) Pyrisoxazol, (1.66) 2- {[3-(2-Chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl} -2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.67) l- {[3-(2-Chlorphenyl)-1) inhibitors of ergosterol biosynthesis, for example (1.01) aldimorph, (1.02) azaconazole, (1.03) bitertanol, (1.04) bromuconazole, (1.05) cyproconazole, (1.06) diclobutrazole, (1.07) difenoconazole, (1.08) diniconazole, (1.09 ) Dinemonazole-M, (1.10) dodemorph, (1.11) dodemorphoacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalil sulfate, (1.28) Imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifine, (1.33) nuarimol, (1.34) oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37) penconazole, (1.38) Piperaline, (1.39) prochloroconazole, (1.42) propiconazole, (1.41) pyributicarb, (1.43) pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47) tebuconazole, (1 .48) Terbinafine, (1.49) Tetraconazole, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizole, (1.54) Triforin, (1.55) Triticonazole, (1.56) Uniconazole, (1.57) Uniconazole p, (1.58) viniconazole, (1.59) voriconazole, (1.60) 1- (4-chlorophenyl) -2- (1H-l, 2,4-triazol-1-yl) cycloheptanol, (1 -61) 1 - ( 2,2-dimethyl-2,3-dihydro-1H-inden-1-yl) -1H-imidazole-5-carboxylic acid ~ methyl ester, (1.62) N '- {5- (difluoromethyl) -2-methyl- 4- [3- (trimethylsilyl) propoxy] phenyl} -N-ethyl-N-methylimidoformamide, (1.63) N-ethyl-N-methyl-N '- {2-methyl-5- (trifluoromethyl) -4- [3 - (trimethylsilyl) propoxy] phenyl} imidoformamide, (1.64) O- [1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl] -1H-imidazole-1-carbothioate, (1.65) pyrisoxazole, (1.66 ) 2- {[3- (2-Chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-l, 2,4-triazole-3-thione , (1.67) 1- {[3- (2-chlorophenyl) -
2- (2,4-difluorphenyl)oxiran-2-yl]methyl} -lH-l,2,4-triazol-5-ylthiocyanat, (1.68) 5-(Allylsulfanyl)-l- {[3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} -lH-l,2,4-triazol, (1.69) 2-[l-(2,4- Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.70) 2- {[rel(2R,3S)-3-(2-Chlo^henyl)-2-(2,4-difl 2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -LH-l, 2,4-triazol-5-ylthiocyanate, (1.68) 5- (allylsulfanyl) -l- {[3- (2- chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-l, 2,4-triazole, (1.69) 2- [1- (2,4-dichlorophenyl) -5-hydroxy -2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.70) 2- {[rel (2R, 3S) -3- (2-Chlo ^ henyl) -2- (2,4-dIfL
3- thion, (1.71) 2- {[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)-oxiran-2-yl]methyl}-2,4- dihydro-3H-l,2,4-triazol-3-thion, (1.72) l- {[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran- 2-yl]methyl} -lH-l,2,4-triazol-5-ylthiocyanat, (1.73) l- {[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl} -lH-l,2,4-triazol-5-ylthiocyanat, (1 -74) 5-(Allylsulfanyl)-l- {[rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol, (1.75) 5- (Allylsulfanyl)-l- {[rel(2R,3R)-3-(2-chlo^henyl)-2-(2,4-difluo^henyl)oxiran-2-yl]methyl}-lH-l,2,4- triazol, (1.76) 2-[(2S,4S,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro- 3H-l,2,4-triazol-3-thion, (1.77) 2-[(2R,4S,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan- 3-thione, (1.71) 2- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro 3H-l, 2,4-triazole-3-thione, (1.72) 1 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2] yl] methyl} -1H-l, 2,4-triazol-5-ylthiocyanate, (1.73) 1- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -LH-l, 2,4-triazol-5-ylthiocyanate, (1-74) 5- (allylsulfanyl) -l- [¢ (2R, 3S) -3- (2- chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -LH-l, 2,4-triazole, (1.75) 5- (allylsulfanyl) -l- {[rel (2R, 3R) -3- (2-chlorobenhenyl) -2- (2,4-difluoroethylenium) oxiran-2-yl] methyl} -1H-l, 2,4-triazole, (1.76) 2 - [(2S, 4S, 5S) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3 thion, (1.77) 2 - [(2R, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane
4- yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.78) 2-[(2R,4R,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy- 2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.79) 2-[(2S,4R,5R)-l-(2,4-4-yl] -2,4-dihydro-3H-1, 2,4-triazole-3-thione, (1.78) 2 - [(2R, 4R, 5R) -1- (2,4-dichlorophenyl) -5 -hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.79) 2 - [(2S, 4R, 5R) - l- (2,4-
Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.80) 2- [(2S,4S,5R)-l-(2,4-Dichlo^henyl)-5-hydroxy-2,6,6 rimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4 riazol- 3- thion, (1.81) 2-[(2R,4S,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l,2,4-triazol-3-thion, (1.82) 2-[(2R,4R,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.83) 2-[(2S,4R,5S)-l-(2,4-Dichlorphenyl)- 5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.84) 2-[4-(4- Chlo^henoxy)-2-(trifluormethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (1.85) 2-[4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (1.86) 2- [4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)pentan-2-ol, (1.87) 2- [2-Chlor-4-(4- chlorphenoxy)phenyl]-l -(lH-l,2,4-triazol-l -yl)butan-2-ol, (1.88) 2-[2-Chlor-4-(2,4- dichlorphenoxy)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (1.89) (2R)-2-(l-Chlorcyclopropyl)-4- [(lR)-2,2-dichlorcyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.90) (2R)-2-(l-Chlorcyclopropyl)-Dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.80) 2- [(2S, 4S , 5R) -1- (2,4-Dichloro-1-yl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1, 2,4-riazole 3-thione, (1.81) 2 - [(2R, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro 3H-l, 2,4-triazole-3-thione, (1.82) 2 - [(2R, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane -4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.83) 2 - [(2S, 4R, 5S) -l- (2,4-dichlorophenyl) - 5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.84) 2- [4- (4-chloro henoxy) -2- (trifluoromethyl) phenyl] -1- (1H-l, 2,4-triazol-1-yl) propan-2-ol, (1.85) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.86) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl ] - 1 - (1H-1,2,4-triazol-1-yl) pentan-2-ol, (1.87) 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1- (1H -l, 2,4-triazol-1-yl) butan-2-ol, (1.88) 2- [2-chloro-4- (2,4-dichlorophenoxy) phenyl] -l- (1H-1, 2, 4-triazol-1-yl) propan-2-ol, (1.89) (2R) -2- (1-chlorocyclopropyl) -4- [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1, 2,4-triazol-1-yl) butan-2-ol, (1.90) (2R) -2- (1-chlorocyclopropyl) -
4- [(l S)-2,2-dichlorcyclopropyl]-l -(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.91) (2S)-2-(l- Chlorcyclopropyl)-4- [( 1 S)-2,2-dichlorcyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.92) (2S)-2- (l-Chlorcyclopropyl)-4-[(lR)-2,2-dichlorcyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.93) (1 S,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl- 1 -(1 H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol, (1.94) (lR,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l -(lH-l,2,4-triazol-l- ylmethyl)cyclopentanol, (1 -95) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l -(lH-l,2,4-triazol-l- ylmethyl)cyclopentanol. 4- [(1S) -2,2-dichlorocyclopropyl] -1- (1H-l, 2,4-triazol-1-yl) butan-2-ol, (1.91) (2S) -2- (1H) Chlorocyclopropyl) -4- [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.92) (2S) -2 - (1-Chlorocyclopropyl) -4 - [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.93) (1 p , 2R, 5R) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.94) (IR, 2S, 5S) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-l, 2,4-triazol-1-ylmethyl) cyclopentanol, (1-95) 5- ( 4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-l, 2,4-triazol-1-ylmethyl) cyclopentanol.
2) Inhibitoren der Atmungskette am Komplex I oder II, zum Beispiel (2.01) Bixafen, (2.02) Boscalid, (2.03) Carboxin, (2.04) Diflumetorim, (2.05) Feniuram, (2.06) Fluopyram, (2.07) Flutolanil, (2.08) Fluxapyroxad, (2.09) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam (Mischung von syn-epimerem Racemat 1RS,4SR,9RS und anti-epimerem Racemat 1RS,4SR,9SR), (2.12) Isopyrazam (anti-epimeres Racemat 1RS,4SR,9SR), (2.13) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.14) Isopyrazam (anti-epimeres Enantiomer 1 S,4R,9R), (2.15) Isopyrazam (syn-epimeres Racemat 1RS,4SR,9RS), (2.16) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.17) Isopyrazam (syn-epimeres Enantiomer 1 S,4R,9S), (2.18) Mepronil, (2.19) Oxycarboxin, (2.20) Penflufen, (2.21) Penthiopyrad, (2.22) Sedaxan, (2.23) Thifluzamid, (2.24) l-Methyl-N-[2-(l,l,2,2-tetrafluorethoxy)phenyl]-3-(trifluormethyl)-lH- pyrazol-4-carboxamid, (2.25) 3 -(Difluormethyl)- 1 -methyl-N- [2-( 1 , 1 ,2,2-tetrafluorethoxy)phenyl] - 1 H- pyrazol-4-carboxamid, (2.26) 3-(Difluormethyl)-N-[4-fluor-2-(l , 1,2,3,3, 3-hexafluorpropoxy)phenyl]-l - methyl-lH-pyrazol-4-carboxamid, (2.27) N-[l-(2,4-Dichlorphenyl)-l-methoxypropan-2-yl]-3- (difluormethyl)- l-methyl-lH-pyrazol-4-carboxamid, (2.28) 5,8-Difluor-N-[2-(2-fluor-4- {[4- (trifluormethyl)pyridin-2-yl]oxy}phenyl)ethyl]chinazolin-4-amin, (2.29) Benzovindiflupyr, (2.30) N- [(l S,4R)-9-(Dichlormethylen)-l,2,3,4-tetrahydro-l,4-methanonaphthalin-5-yl]-3-(difluormethyl)-l- methyl- 1 H-pyrazol-4-carboxamid, (2.31) N-[( 1 R,4S)-9-(Dichlormethylen)- 1 ,2,3,4-tetrahydro- 1 ,4- methanonaphthalin-5 -yl] -3 -(difluormethyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.32) 3 - (Difluormethyl)- 1 -methyl-N-( 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 H-pyrazol-4-carboxamid,2) respiratory chain inhibitors on complex I or II, for example (2.01) bixafen, (2.02) boscalid, (2.03) carboxin, (2.04) diflumetorim, (2.05) feniuram, (2.06) fluopyram, (2.07) flutolanil, (2.08 ) Fluxapyroxad, (2.09) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam (mixture of syn-epimeric racemate 1RS, 4SR, 9RS and anti-epimeric racemate 1RS, 4SR, 9SR), (2.12) isopyrazam (anti-epimeric racemate 1RS, 4SR, 9SR), (2.13) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.14) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.15) isopyrazam (syn-epimeric racemate 1RS , 4SR, 9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.18) mepronil, (2.19) oxycarboxine, ( 2.20) Penflufen, (2.21) Penthiopyrad, (2.22) Sedaxane, (2.23) Thifluzamide, (2.24) l-Methyl-N- [2- (l, l, 2,2-tetrafluoroethoxy) phenyl] -3- (trifluoromethyl) -LH-pyrazole-4-carboxamide, (2.25) 3- (difluoromethyl) -1-methyl-N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -1H-pyrazole-4-carb oxamide, (2.26) 3- (difluoromethyl) -N- [4-fluoro-2- (1,2,3,3,3-hexafluoropropoxy) phenyl] -1-methyl-1H-pyrazole-4-carboxamide, (2.27) N- [1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.28) 5.8- Difluoro-N- [2- (2-fluoro-4- {[4- (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazolin-4-amine, (2.29) benzovindiflupyr, (2.30) N- [ (1S, 4R) -9- (dichloromethylene) -1,3,3,4-tetrahydro-1,4-methanonaphthalen-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4 -carboxamide, (2.31) N - [(1R, 4S) -9- (dichloromethylene) -1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] -3- (difluoromethyl) -1 -methyl-1H-pyrazole-4-carboxamide, (2.32) 3 - (difluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl ) - 1H-pyrazole-4-carboxamide,
(2.33) l,3,5-Trimethyl-N-(l ,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-pyrazol-4-carboxamid, (2.34) 1 -Methyl-3 -(trifluormethyl)-N-( 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 H-pyrazol-4-carboxamid, (2.35) l-Methyl-3-(trifluormethyl)-N-[(3R)-l,l,3-trim (2.33) l, 3,5-Trimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.34) 1 - Methyl 3 - (trifluoromethyl) -N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1 H -pyrazole-4-carboxamide, (2.35) 1-Methyl-3- (trifluoromethyl) -N - [(3R) -l, l, 3-trim
carboxamid, (2.36) 1 -Methyl-3 -(trifluormethyl)-N- [(3 S)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, (2.37) 3 -(Difluormethyl)- 1 -methyl-N- [(3 S)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H- inden-4-yl]-lH-pyrazol-4-carboxamid, (2.38) 3-(Difluormethyl)-l-methyl-N-[(3R)-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.39) l,3,5-Trimethyl-N-[(3R)-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.40) l,3,5-Trimethyl-N-[(3S)-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.41) Benodanil, (2.42) 2-Chlor-N-(l ,l,3-trimethyl- 2,3-dihydro-lH-inden-4-yl)pyridin-3-carboxamid, (2.43) Isofetamid, (2.44) 1 -Methyl-3 -(trifluormethyl)- N-[2'-(trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (2.45) N-(4'-Chlorbiphenyl-2-yl)-3- (difluormethyl)- l-methyl-lH-pyrazol-4-carboxamid, (2.46) N-(2',4'-Dichlorbiphenyl-2-yl)-3- (difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.47) 3 -(Difluormethyl)- 1 -methyl-N- [4'- (trifluormethyl)biphenyl-2-yl] - 1 H-pyrazol-4-carboxamid, (2.48) N-(2',5'-Difluorbiphenyl-2-yl)- 1 - methyl-3-(trifluormethyl)-lH-pyrazol-4-carboxamid, (2.49) 3 -(Difluormethyl)- 1 -methyl-N- [4'-(prop-l - in- 1 -yl)biphenyl-2-yl] - 1 H-pyrazol-4-carboxamid, (2.50) 5-Fluor- 1 ,3 -dimethyl-N- [4'-(prop- 1 -in- 1 - yl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (2.51) 2-Chlor-N- [4'-(prop-l -in- l-yl)biphenyl-2- yl]nicotinamid, (2.52) 3 -(Difluormethyl)-N- [4'-(3 ,3 -dimethylbut- 1 -in- 1 -yl)biphenyl-2-yl] - 1 -methyl- 1 H- pyrazol-4-carboxamid, (2.53) N-[4'-(3,3-Dimethylbut-l-in-l-yl)biphenyl-2-yl]-5-fluor-l,3-dimethyl-lH- pyrazol-4-carboxamid, (2.54) 3-(Difluormethyl)-N-(4'-ethinylbiphenyl-2-yl)-l-methyl-lH-pyrazol-4- carboxamid, (2.55) N-(4'-Ethinylbiphenyl-2-yl)-5-fluor-l,3-dimethyl-lH-pyrazol-4-carboxamid, (2.56) 2-Chlor-N-(4'-ethinylbiphenyl-2-yl)nicotinamid, (2.57) 2-Chlor-N-[4'-(3,3-dimethylbut-l-in-l- yl)biphenyl-2-yl]nicotinamid, (2.58) 4-(Difluormethyl)-2-methyl-N- [4'-(trifluormethyl)biphenyl-2-yl] - l,3-thiazol-5-carboxamid, (2.59) 5-Fluor-N-[4'-(3-hydroxy-3-methylbut-l-in-l -yl)biphenyl-2-yl]-l,3- dimethyl- 1 H-pyrazol-4-carboxamid, (2.60) 2-Chlor-N- [4'-(3 -hydroxy-3 -methylbut- 1 -in- 1 -yl)biphenyl-2- yl]nicotinamid, (2.61) 3 -(Difluormethyl)-N- [4'-(3 -methoxy-3 -methylbut- 1 -in- 1 -yl)biphenyl-2-yl] - 1 - methyl- lH-pyrazol-4-carboxamid, (2.62) 5-Fluor-N-[4'-(3-methoxy-3-methylbut-l-in-l-yl)biphenyl-2- yl] - 1 ,3 -dimethyl- 1 H-pyrazol-4-carboxamid, (2.63) 2-Chlor-N- [4'-(3 -methoxy-3 -methylbut- 1 -in- 1 - yl)biphenyl-2-yl]nicotinamid, (2.64) l,3-Dimethyl-N-(l ,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH- pyrazol-4-carboxamid, (2.65) l,3-Dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH- pyrazol-4-carboxamid, (2.66) l,3-Dimethyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH- pyrazol-4-carboxamid, (2.67) 3-(Difluormethyl)-N-methoxy-l-methyl-N-[l-(2,4,6- trichlorphenyl)propan-2-yl]-lH-pyrazol-4-carboxamid, (2.68) 3-(Difluormethyl)-N-(7-fluor-l,l,3- trimethyl-2,3-dihydro-lH-inden-4-yl)-l-methyl-lH-pyrazol-4-carboxamid, (2.69) 3-(Difluormethyl)-N- [(3R)-7-fluor-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazol-4-carboxamid, (2.70) 3- (Difluormethyl)-N- [(3 S)-7-fluor- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 -methyl- 1 H-pyrazol-4- carboxamid. carboxamide, (2.36) 1-Methyl-3 - (trifluoromethyl) -N- [(3S) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1 H- pyrazole-4-carboxamide, (2.37) 3 - (Difluoromethyl) -1-methyl-N- [(3S) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -LH-pyrazole-4-carboxamide, (2.38) 3- (difluoromethyl) -l-methyl-N - [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl ] -lH-pyrazole-4-carboxamide, (2.39) l, 3,5-trimethyl-N - [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -lH-pyrazole-4-carboxamide, (2.40) l, 3,5-trimethyl-N - [(3S) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] - 1H-pyrazole-4-carboxamide, (2.41) benodanil, (2.42) 2-chloro-N- (1, 1, 3-trimethyl-2,3-dihydro-1H-inden-4-yl) pyridine-3-carboxamide , (2.43) Isofetamide, (2.44) 1-Methyl-3 - (trifluoromethyl) - N - [2 '- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (2.45) N- (4 '-Chlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.46) N- (2', 4'-dichlorobiphenyl-2-yl) -3- (difluoromethyl ) -l-methyl-1H-pyrazole-4-carboxamide, (2.47) 3- (difluoromethyl) -1 -methyl-N- [4'- (trifluoromethyl) biphenyl-2-yl] -1-H-pyrazole-4-carboxamide, (2.48) N- (2 ', 5'-difluorobiphenyl-2-yl) -1-methyl -3- (trifluoromethyl) -1H-pyrazole-4-carboxamide, (2.49) 3- (difluoromethyl) -1-methyl-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl ] - 1 H-pyrazole-4-carboxamide, (2.50) 5-fluoro-1, 3-dimethyl-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] -lH- pyrazole-4-carboxamide, (2.51) 2-chloro-N- [4 '- (prop-1-yl-yl) biphenyl-2-yl] nicotinamide, (2.52) 3 - (difluoromethyl) -N- [ 4 '- (3,3-dimethylbut-1-yn-1-yl) biphenyl-2-yl] -1-methyl-1H-pyrazole-4-carboxamide, (2.53) N- [4' - (3, 3-dimethylbut-1-yn-1-yl) biphenyl-2-yl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (2.54) 3- (difluoromethyl) -N- (4 '-ethynyl-biphenyl-2-yl) -l-methyl-1H-pyrazole-4-carboxamide, (2.55) N- (4'-ethynyl-biphenyl-2-yl) -5-fluoro-1,3-dimethyl-1H-pyrazole 4-carboxamide, (2.56) 2-chloro-N- (4'-ethynylbiphenyl-2-yl) nicotinamide, (2.57) 2-chloro-N- [4 '- (3,3-dimethylbut-1-yne] 1-yl) biphenyl-2-yl] nicotinamide, (2.58) 4- (difluoromethyl) -2-methyl -N- [4 '- (trifluoromethyl) biphenyl-2-yl] -1,3-thiazole-5-carboxamide, (2.59) 5-fluoro-N- [4' - (3-hydroxy-3-methylbut-1 -in-1-yl) biphenyl-2-yl] -1,3-dimethyl-1H-pyrazole-4-carboxamide, (2.60) 2-chloro-N- [4 '- (3-hydroxy-3-methylbut - 1-yn-1-yl) biphenyl-2-yl] nicotinamide, (2.61) 3- (difluoromethyl) -N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl -2-yl] - 1-methyl-1H-pyrazole-4-carboxamide, (2.62) 5-fluoro-N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl 2-yl] -1,3-dimethyl-1H-pyrazole-4-carboxamide, (2.63) 2-chloro-N- [4 '- (3-methoxy-3-methylbut-1-in-1-yl) biphenyl-2-yl] nicotinamide, (2.64) 1,3-dimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide , (2.65) 1,3-dimethyl-N - [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.66 ) 1,3-Dimethyl-N - [(3S) -1,3,1-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.67) 3- (Difluoromethyl) -N-methoxy-1-methyl-N- [1- (2,4,6-trichlorophenyl) propan-2-yl] -1H-pyrazole-4-carboxamide, (2.68) 3- (Difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1-methyl-1H-pyrazole-4-carboxamide, (2.69 ) 3- (Difluoromethyl) -N- [(3R) -7-fluoro-1,1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4 carboxamide, (2.70) 3- (difluoromethyl) -N- [(3S) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] - 1 - methyl-1H-pyrazole-4-carboxamide.
3) Inhibitoren der Atmungskette am Komplex III, zum Beispiel (3.01) Ametoctradin, (3.02) Amisulbrom, (3.03) Azoxystrobin, (3.04) Cyazofamid, (3.05) Coumethoxystrobin, (3.06) Coumoxystrobin, (3.07) Dimoxys robin, (3.08) Enoxas robin, (3.09) Famoxadon, (3.10) Fenamidon, (3.11) Flufenoxystrobin, (3.12) Fluoxastrobin, (3.13) Kresoxim-methyl, (3.14) Metominostrobin, (3.15) Orysastrobin, (3.16) Picoxystrobin, (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E)-2-(2- {[6- (3-Chlor-2-methylphenoxy)-5-fluo^yrimidin-4-yl]oxy}phenyl)-2-^ 3) Complex III respiratory chain inhibitors, for example (3.01) ametoctradine, (3.02) amisulbrom, (3.03) azoxystrobin, (3.04) cyazofamide, (3.05) coumethoxystrobin, (3.06) Coumoxystrobin, (3.07) Dimoxys robin, (3.08) Enoxas robin, (3.09) Famoxadone, (3.10) Fenamidone, (3.11) Flufenoxystrobin, (3.12) Fluoxastrobin, (3.13) Kresoxim-methyl, (3.14) Metominostrobin, (3.15) Orysastrobin , (3.16) Picoxystrobin, (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E) -2- (2- [ 6- (3-chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yl] oxy} phenyl) -2- ^
(3.24) (2E)-2-(Methoxyimino)-N-methyl-2-(2- { [( {(1 E)- 1 -[3 -(trifluormethyl)phenyl]-ethyli- den}_,amino)oxy]methyl}phenyl)acetamid, (3.25) (2E)-2-(Methoxyimino)-N-methyl-2- {2-[(E)-({l -[3- (trifluormethyl)phenyl] ethoxy } imino)methyl]phenyl} acetamid, (3.26) (2E)-2- {2- [( { [( 1 E)- 1 -(3 - { [(E)- 1 - Fluor-2-phenylvinyl] oxy } phenyl)ethyliden] amino } oxy)methyl]phenyl} -2-(methoxyimino)-N-methyl- acetamid, (3.27) Fenaminostrobin, (3.28) 5-Methoxy-2-methyl-4-(2- {[( {(lE)-l-[3- (trifluormethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-l,2,4-triazol-3-on, (3.29) (2E)-2- {2-[( {Cyclopropyl[(4-methoxyphenyl)imino]methyl} sulfanyl)methyl]phenyl} -3-methoxy- acrylsäuremethylester, (3.30) N-(3-Ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamid, (3.31) 2- {2-[(2,5-Dimethylphenoxy)methyl]phenyl} -2-methoxy-N-methylacetamid, (3.32) 2- {2-[(2,5- Dimethylphenoxy)methyl]phenyl} -2-methoxy-N-methylacetamid, (3.33) (2E,3Z)-5- {[l-(4-Chlor- phenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid. (3.24) (2E) -2- (methoxyimino) -N-methyl-2- (2- {[({(1E) -1- [3 - (trifluoromethyl) phenyl] ethylidene} , amino) oxy] methyl} phenyl) acetamide, (3.25) (2E) -2- (methoxyimino) -N-methyl-2- {2 - [(E) - ({1- [3- (trifluoromethyl) phenyl] ethoxy} imino ) methyl] phenyl} acetamide, (3.26) (2E) -2- {2- [({[(1E) -1- (3 - {[(E) -1-fluoro-2-phenylvinyl) oxy} phenyl ) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylacetamide, (3.27) fenaminostrobin, (3.28) 5-methoxy-2-methyl-4- (2- {[({( lE) -l- [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) -2,4-dihydro-3H-l, 2,4-triazol-3-one, (3.29) (2E) -2- {2 - [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxy-acrylic acid methyl ester, (3.30) N- (3-ethyl-3,5,5-trimethylcyclohexyl ) -3-formamido-2-hydroxybenzamide, (3.31) 2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.32) 2- {2 - [(2 , 5-Dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.33) (2E, 3Z) -5- {[1- (4-chlorophenyl) -lH-pyrazole-3 -yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide.
4) Inhibitoren der Mitose und Zellteilung, zum Beispiel (4.01) Benomyl, (4.02) Carbendazim, (4.03) Chlorfenazol, (4.04) Diethofencarb, (4.05) Ethaboxam, (4.06) Fluopicolid, (4.07) Fuberidazol, (4.08) Pencycuron, (4.09) Thiabendazol, (4.10) Thiophanat-methyl, (4.11) Thiophanat, (4.12) Zoxamid, (4.13) 5-Chlor-7-(4-methylpiperidin-l -yl)-6-(2A (4.14) 3-4) inhibitors of mitosis and cell division, for example (4.01) benomyl, (4.02) carbendazim, (4.03) chlorfenazole, (4.04) diethofencarb, (4.05) ethaboxam, (4.06) fluopicolide, (4.07) fuberidazole, (4.08) pencycuron, (4.09) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2A (4.14) 3-
Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin. Chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) -pyridazine.
5) Verbindungen, die dazu fähig sind, an mehreren Stellen anzugreifen („Multisite Action"), zum Beispiel (5.01) Bordeaux-Mischung, (5.02) Captafol, (5.03) Captan, (5.04) Chlorothalonil, (5.05) Kupferhydroxid, (5.06) Kupfernaphthenat, (5.07) Kupferoxid, (5.08) Kupferoxychlorid, (5.09) Kupfer(2+)-sulfat, (5.10) Dichlofluanid, (5.11) Dithianon, (5.12) Dodin, (5.13) Dodin freie Base, (5.14) Ferbam, (5.15) Fluorofolpet, (5.16) Folpet, (5.17) Guazatin, (5.18) Guazatinacetat, (5.19) Iminoctadin, (5.20) Iminoctadinalbesilat, (5.21) Iminoctadintriacetat, (5.22) Mancopper, (5.23) Mancozeb, (5.24) Maneb, (5.25) Metiram, (5.26) Metiram-Zink, (5.27) Oxin-Kupfer, (5.28) Propamidin, (5.29) Propineb, (5.30) Schwefel und Schwefelzubereitungen einschließlich Calciumpolysulfid, (5.31) Thiram, (5.32) Tolylfluanid, (5.33) Zineb, (5.34) Ziram, (5.35) Anilazin. 5) compounds capable of attacking at multiple sites ("multisite action"), for example (5.01) Bordeaux mixture, (5.02) captafol, (5.03) captan, (5.04) chlorothalonil, (5.05) copper hydroxide, ( 5.06) copper naphthenate, (5.07) copper oxide, (5.08) copper oxychloride, (5.09) copper (2+) sulfate, (5.10) dichlorofluanide, (5.11) dithianon, (5.12) dodin, (5.13) dodine free base, (5.14) Ferbam, (5.15) fluorofolpet, (5.16) folpet, (5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20) iminoctadinalbesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) Maneb, (5.25) metiram, (5.26) metiram-zinc, (5.27) oxine-copper, (5.28) propamidine, (5.29) propineb, (5.30) sulfur and sulfur compounds including calcium polysulfide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34) ziram, (5.35) anilazine.
6) Verbindungen, die dazu fähig sind, eine Abwehrreaktion des Wirtes zu induzieren, zum Beispiel (6.01) Acibenzolar-S-methyl, (6.02) Isotianil, (6.03) Probenazol, (6.04) Tiadinil, (6.05) Laminarin. 6) Compounds capable of inducing host defense response, for example (6.01) acibenzolar-S-methyl, (6.02) isotianil, (6.03) probenazole, (6.04) tiadinil, (6.05) laminarin.
7) Inhibitoren der Aminosäure- und/oder Proteinbiosynthese, zum Beispiel (7.01) Andoprim, (7.02) Blasticidin-S, (7.03) Cyprodinil, (7.04) Kasugamycin, (7.05) Kasugamycinhydrochlorid-hydrat, (7.06) Mepanipyrim, (7.07) Pyrimethanil, (7.08) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l- yl)chinolin, (7.09) Oxytetracyclin, (7.10) Streptomycin. 7) inhibitors of amino acid and / or protein biosynthesis, for example (7.01) andoprim, (7.02) blasticidin-S, (7.03) cyprodinil, (7.04) kasugamycin, (7.05) kasugamycin hydrochloride hydrate, (7.06) Mepanipyrim, (7.07) pyrimethanil, (7.08) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (7.09) oxytetracycline, (7.10) streptomycin.
8) Inhibitoren der ATP-Produktion, zum Beispiel (8.01) Fentinacetat, (8.02) Fentinchlorid, (8.03) Fentinhydroxid, (8.04) Silthiofam. 9) Inhibitoren der Zellwandsynthese, zum Beispiel (9.01) Benthiavalicarb, (9.02) Dimethomorph, (9.03) Flumorph, (9.04) Iprovalicarb, (9.05) Mandipropamid, (9.06) Polyoxine, (9.07) Polyoxorim, (9.08) Validamycin A, (9.09) Valifenalat, (9.10) Polyoxin B, (9.11) (2E)-3-(4-tert.-Butylphenyl)-3-(2- chlorpyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-on, (9.12) (2Z)-3-(4-tert.-Butylphenyl)-3-(2- chlorpyridin-4-yl)- 1 -(morpholin-4-yl)prop-2-en- 1 -on. 10) Inhibitoren der Lipid- und Membransynthese, zum Beispiel (10.01) Biphenyl, (10.02) Chloroneb, (10.03) Dicloran, (10.04) Edifenphos, (10.05) Etridiazol, (10.06) Iodocarb, (10.07) Iprobenfos, (10.08) Isoprothiolan, (10.09) Propamocarb, (10.10) Propamocarbhydrochlorid, (10.11) Prothiocarb, (10.12) Pyrazophos, (10.13) Quintozen, (10.14) Tecnazen, (10.15) Tolclofos-methyl. 8) inhibitors of ATP production, for example (8.01) fentin acetate, (8.02) fentin chloride, (8.03) fentin hydroxide, (8.04) silthiofam. 9) inhibitors of cell wall synthesis, for example (9.01) benthi- avalicarb, (9.02) dimethomorph, (9.03) flumorph, (9.04) iprovalicarb, (9.05) mandipropamide, (9.06) polyoxines, (9.07) polyoxorim, (9.08) validamycin A, ( 9.09) Valifenalate, (9.10) Polyoxin B, (9.11) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop -2-en-1-one, (9.12) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) propyl 2-en-1-on. 10) inhibitors of lipid and membrane synthesis, for example (10.01) biphenyl, (10.02) chloroneb, (10.03) diclorane, (10.04) edifenphos, (10.05) etridiazole, (10.06) iodocarb, (10.07) Iprobenfos, (10.08) isoprothiolane , (10.09) Propamocarb, (10.10) Propamocarb hydrochloride, (10.11) Prothiocarb, (10.12) Pyrazophos, (10.13) Quintozene, (10.14) Tecnazene, (10.15) Tolclofos-methyl.
11) Inhibitoren der Melaninbiosynthese, zum Beispiel (11.01) Carpropamid, (11.02) Diclocymet, (1 1.03) Fenoxanil, (11.04) Phthalid, (11.05) Pyroquilon, (11.06) Tricyclazol, (11.07) 2,2,2-Trifluorethyl11) inhibitors of melanin biosynthesis, for example (11.01) carpropamide, (11.02) diclocymet, (1.03) fenoxanil, (11.04) phthalide, (11.05) pyroquilone, (11.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl
{3-methyl-l-[(4-methylbenzoyl)amino]butan-2-yl}carbamat. {3-methyl-l - [(4-methylbenzoyl) amino] butan-2-yl} carbamate.
12) Inhibitoren der Nukleinsäuresynthese, zum Beispiel (12.01) Benalaxyl, (12.02) Benalaxyl-M (Kiralaxyl), (12.03) Bupirimat, (12.04) Clozylacon, (12.05) Dimethirimol, (12.06) Ethirimol, (12.07) Furalaxyl, (12.08) Hymexazol, (12.09) Metalaxyl, (12.10) Metalaxyl-M (Mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinsäure, (12.14) Octhilinon. 12) Inhibitors of Nucleic Acid Synthesis, for example (12.01) Benalaxyl, (12.02) Benalaxyl-M (Kiralaxyl), (12.03) Bupirimat, (12.04) Clozylacone, (12.05) Dimethirimol, (12.06) Ethirimol, (12.07) Furalaxyl, (12.08 ) Hymexazole, (12.09) Metalaxyl, (12.10) Metalaxyl-M (mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinic acid, (12.14) Octhilinone.
13) Inhibitoren der Signalvermittlung, zum Beispiel (13.01) Chlozolinat, (13.02) Fenpiclonil, (13.03) Fludioxonil, (13.04) Iprodion, (13.05) Procymidon, (13.06) Quinoxyfen, (13.07) Vinclozolin, (13.08) Proquinazid. 13) inhibitors of signal mediation, for example (13.01) chlozolinate, (13.02) fenpiclonil, (13.03) fludioxonil, (13.04) iprodione, (13.05) procymidone, (13.06) quinoxyfen, (13.07) vinclozoline, (13.08) proquinazide.
14) Verbindungen, die als Entkoppler wirken können, zum Beispiel (14.01) Binapacryl, (14.02) Dinocap, (14.03) Ferimzon, (14.04) Fluazinam, (14.05) Meptyldinocap. 14) compounds which may act as decouplers, for example (14.01) binapacryl, (14.02) dinocap, (14.03) ferimzone, (14.04) fluazinam, (14.05) meptyldinocap.
15) Weitere Verbindungen, zum Beispiel (15.001) Benthiazol, (15.002) Bethoxazin, (15.003) Capsimycin, (15.004) Carvon, (15.005) Chinomethionat, (15.006) Pyriofenon (Chlazafenon), (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamid, (15.011) Dazomet, (15.012) Debacarb, (15.013) Dichlorophen, (15.014) Diclomezin, (15.015) Difenzoquat, (15.016) Difenzoquatmetilsulfat, (15.017) Diphenylamin, (15.018) Ecomat, (15.019) Fenpyrazamin, (15.020) Flumetover, (15.021) Fluoroimid, (15.022) Flusulfamid, (15.023) Flutianil, (15.024) Fosetyl- Aluminium, (15.025) Fosetyl-Calcium, (15.026) Fosetyl-Natrium, (15.027) Hexachlorbenzol, (15.028) Irumamycin, (15.029) Methasulfocarb, (15.030) Methylisothiocyanat, (15.031) Metrafenon, (15.032) Mildiomycin, (15.033) Natamycin, (15.034) Nickeldimethyldithiocarbamat, (15.035) Nitrothal- isopropyl, (15.036) Oxamocarb, (15.037) Oxyfenthiin, (15.038) Pentachlorphenol und Salze, (15.039) Phenothrin, (15.040) phosphorige Säure und deren Salze, (15.041) Propamocarb-fosetylat, (15.042) Propanosin-Natrium, (15.043) Pyrimorph, (15.044) Pyrrolnitrin, (15.045) Tebufloquin, (15.046) Tecloftalam, (15.047) Tolnifanid, (15.048) Triazoxid, (15.049) Trichlamid, (15.050) Zarilamid, (15.051) 2-Methylpropansäure-(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2- yl}carbonyl)amino]-6-methyl-4,9-dioxo-l,5-dioxonan-7-ylester, (15.052) l-(4- {4-[(5R)-5-(2,6- Difluorphenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3- (trifluormethyl)-lH-pyrazol-l-yl]ethanon, (15.053) l-(4- {4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro- l,2-oxazol-3-yl]-l,3 hiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluormethyl)-lH-pyrazol-l- yljethanon, (15.054) Oxathiapiprolin, (15.055) lH-Imidazol-l -carbonsäure-l-(4-methoxyphenoxy)-3,3- dimethylbutan-2-ylester, (15.056) 2,3,5, 6-Tetrachlor-4-(methylsulfonyl)pyridin, (15.057) 2,3-Dibutyl-6- chlorthieno[2,3-d]pyrimidin-4(3H)-on, (15.058) 2,6-Dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrol- l,3,5,7(2H,6H)-tetron, (15.059) 2-[5-Methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]-l-(4- {4-[(5R)-5- phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)ethanon, (15.060) 2-[5-Methyl-3- (trifluormethyl)- 1 H-pyrazol- 1 -yl] - 1 -(4- yl}piperidin-l -yl)ethanon, (15.061) 2-[5-Methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]-l- {4-[4-(5-phenyl- 4,5-dihydro-l,2-oxazol-3-yl)-l,3-thiazol-2-yl]piperidin-l-yl}ethanon, (15.062) 2-Butoxy-6-iod-3- propyl-4H-chromen-4-on, (15.063) 2-Chlor-5-[2-chlor-l-(2,6-difluor-4-methoxyphenyl)-4-methyl-lH- imidazol-5-yl]pyridin, (15.064) 2-Phenylphenol und Salze, (15.065) 3-(4,4,5-Trifluor-3,3-dimethyl-3,4- dihydroisochinolin-l -yl)chinolin, (15.066) 3,4,5-Trichlorpyridin-2,6-dicarbonsäurenitril, (15.067) 3- Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (15.068) 4-(4-Chlorphenyl)-5-(2,6- difluorphenyl)-3,6-dimethylpyridazin, (15.069) 5-Amino-l,3,4-thiadiazol-2-thiol, (15.070) 5-Chlor-N'- phenyl-N'-(prop-2-in-l-yl)thiophen-2-sulfonohydrazid, (15.071) 5-Fluor-2-[(4- fluorbenzyl)oxy]pyrimidin-4-amin, (15.072) 5-Fluor-2-[(4-methylbenzyl)oxy]pyrimidin-4-amin, (15.073) 5-Methyl-6-octyl[l,2,4]triazolo[l,5-a]pyrimidin-7-amin, (15.074) (2Z)-3-Amino-2-cyano-3- phenylacrylsäureethylester, (15.075) N'-(4- {[3-(4-Chlorbenzyl)-l,2,4-thiadiazol-5-yl]oxy} -2,5- dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.076) N-(4-Chlorbenzyl)-3 - [3 -methoxy-4-(prop- 2-in-l-yloxy)phenyl]propanamid, (15.077) N-[(4-Chlorphenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2- in-l-yloxy)phenyl]propanamid, (15.078) N-[(5-Brom-3-chlorpyridin-2-yl)methyl]-2,4- dichlornicotinamid, (15.079) N-[l -(5-Brom-3-chlorpyridin-2-yl)ethyl]-2,4-dichlornicotinamid, (15.080) N-[l-(5-Brom-3-chlorpyridin-2-yl)ethyl]-2-fluor-4-iodnicotinamid, (15.081) N- {(E)-[(Cyclo- propylmethoxy)imino] [6-(difluormethoxy)-2,3-difluorphenyl]methyl} -2-phenylacetamid, (15.082) N- {(Z)-[(Cyclopropylmethoxy)imino][6-(difluormethoxy)-2,3-difluorphenyl]methyl} -2-phenylacetamid, (15.083) N'- {4-[(3-tert.-Butyl-4-cyano-l,2-thiazol-5-yl)oxy]-2-chlor-5-methylphenyl}-N-ethyl-N- methylimidoformamid, (15.084) N-Methyl-2-( 1 - { [5-methyl-3 -(trifluormethyl)- 1 H-pyrazol- 1 - yl] acetyl} iperidin-4-yl)-N-( 1 ,2,3 ,4-tetrahydronaphthalin- 1 -yl)- 1 ,3 -thiazol-4-carboxamid, (15.085) N- Methyl-2-( 1 - { [5-methyl-3 -(trifluormethyl)-l H-pyrazol- 1 -yl] acetyl} piperidin-4-yl)-N-[(lR)-l,2,3,4- tetrahydronaphthalin-l-yl]-l,3-thiazol-4-carboxamid, (15.086) N-Methyl-2-(l- {[5-methyl-3- (trifluormethyl)- 1 H-pyrazol- 1 -yl] acetyl} piperidin-4-yl)-N- [(1S)-1 ,2,3 ,4-tetrahydronaphthalin- 1 -yl] -1,3- thiazol-4-carboxamid, (15.087) {6-[({[(l-Methyl-lH-tetrazol-5-yl)(phenyl)methy- len] amino } oxy)methyl]pyridin-2-yl} -■carbamidsäurepentylester, (15.088) Phenazin- 1 -carbonsäure, (15.089) Chinolin-8-ol, (15.090) Chinolin-8-olsulfat (2: 1), (15.091) {6-[({[(l-Methyl-lH-tetrazol-5- yl)(phenyl)methylen] _,amino } -Oxy)methyl] pyridin-2 -yl } carbamidsäure-tert. -butylester, (15.092) (5- Brom-2-methoxy-4-methyl_,pyridm-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanon, (15.093) N-[2- (4- { [3 -(4-Chlorphenyl)prop-2-in- 1 -yl] oxy } -3 -methoxyphenyl)ethyl] -N2-(methylsulfonyl)valinamid,15) Further compounds, for example (15.001) Benthiazole, (15.002) Bethoxazine, (15.003) Capsimycin, (15.004) Carvone, (15.005) Quinomethionate, (15.006) Pyriofenone (Chlazafenone), (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Dazomet, (15.012) Debacarb, (15.013) Dichlorophene, (15.014) Diclomecine, (15.015) Difenzoquat, (15.016) Difenzoquatmetyl sulfate, (15.017) Diphenylamine, (15.018) Ecomat, (15.019) fenpyrazamine, (15.020) flumetover, (15.021) fluoroimide, (15.022) flusulfamide, (15.023) flutianil, (15.024) fosetyl-aluminum, (15.025) fosetyl-calcium, (15.026) fosetyl-sodium, (15.027) hexachlorobenzene , (15,028) Irumamycin, (15.029) methasulfocarb, (15.030) methyl isothiocyanate, (15.031) metrafenone, (15.032) mildiomycin, (15.033) natamycin, (15.034) nickel dimethyldithiocarbamate, (15.035) nitrothal isopropyl, (15.036) oxamocarb, (15.037) oxyfenthiine, ( 15.038) pentachlorophenol and salts, (15.039) phenothrin, (15.040) phosphorous acid and its salts, (15.041) propamocarb-fosetylate, (15.042) propanosine sodium, (15.043) pyrimorphine, (15.044) pyrrolitrin, (15.045) tebufloquine, 15.046) Tecloftalam, (15.047) Tolnifanide, (15.048) Triazoxide, (15.049) Trichlamide, (15.050) Zarilamide, (15.051) 2-Methylpropanoic acid (3S, 6S, 7R, 8R) -8-benzyl-3 - [({ 3 - [(isobutyryloxy) methoxy] -4-methoxypyridin-2-yl} carbonyl) amino] -6-methyl-4,9-dioxo-l, 5-dioxonan-7-yl ester, (15.052) l- (4- {4 - [(5R) -5- (2,6-Difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl ) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (15.053) 1- (4- {4 - [(5S) -5- (2,6-difluorophenyl) -4,5-dihydro-l, 2-oxazol-3-yl] -1,3-hiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl-isethanone, (15.054) oxathiapiproline, (15.055) 1H-imidazole-1-carboxylic acid 1- (4-methoxyphenoxy ) -3,3-dimethylbutan-2-yl ester, (15.056) 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, (15,057) 2,3-dibutyl-6-chlorothieno [2,3-d ] pyrimidin-4 (3H) -one, (15.058) 2,6-dimethyl-1H, 5H- [l, 4] dithiino [2,3-c: 5,6-c '] dipyrrole, 3.5 , 7 (2H, 6H) -tetron, (15.059) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- (4- {4 - [(5R) -5- phenyl-4,5-dihydro-1,2-oxazol-3-yl] -l, 3-thiazol-2-yl} piperidin-1-yl) ethanone, (15.060) 2- [5-methyl-3 ( trifluoromethyl) -1 H -pyrazol-1-yl] -1- (4-yl) piperidin-1-yl) ethanone, (15.061) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazole-1-one yl] -l- {4- [4- (5-phenyl-4,5-dihydro-l, 2-oxazol-3-yl) -l, 3-thiazol-2-yl] -piperidin-1-yl} ethanone , (15.062) 2-Butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.063) 2-Chloro-5- [2-chloro-L- (2,6-difluoro-4-methoxyphenyl ) -4-methyl-1H-imidazol-5-yl] pyridine, (15.064) 2-phenylphenol and salts, (15.065) 3- (4,4,5-trifluoro- 3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.066) 3,4,5-trichloropyridine-2,6-dicarboxylic acid nitrile, (15.067) 3-chloro-5- (4-chlorophenyl) - 4- (2,6-difluorophenyl) -6-methylpyridazine, (15.068) 4- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (15,069) 5-amino-1, 3,4-thiadiazole-2-thiol, (15.070) 5-chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene-2-sulfonohydrazide, (15.071) 5-fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidin-4-amine, (15.072) 5-fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15.073) 5-methyl-6-octyl [l , 2,4] triazolo [l, 5-a] pyrimidin-7-amine, (15.074) (2Z) -3-amino-2-cyano-3-phenylacrylic acid ethyl ester, (15.075) N '- (4- {[3 - (4-chlorobenzyl) -1,2,4-thiadiazol-5-yl] oxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (15.076) N- (4-chlorobenzyl) -3 - [3-Methoxy-4- (prop-2-yn-1-yloxy) phenyl] propanamide, (15.077) N - [(4-chlorophenyl) (cyano) methyl] -3- [3-methoxy-4- (prop -2-in-1-yloxy) phenyl] propanamide, (15.078) N - [(5-bromo-3-chloropyridin-2-yl) methyl] -2,4-dichloronotinamide, (15.079) N - [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloronotinamide, (15,080) N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] - 2-fluoro-4-iodo nicotinamide, (15.081) N - {(E) - [(Cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, (15.082) N - {(Z) - [(Cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, (15.083) N '- {4 - [(3-tert-butyl) 4-cyano-1,2-thiazol-5-yl) oxy] -2-chloro-5-methylphenyl} -N-ethyl-N-methylimidoformamide, (15.084) N-methyl-2- (1 - {[5- Methyl-3 - (trifluoromethyl) -1-H-pyrazole-1 - yl] acetyl} iperidin-4-yl) -N- (1,2,3,4-tetrahydronaphthalene-1-yl) -1,3-thiazole-4-carboxamide, (15.085) N-methyl-2- (1 - {[5-methyl-3 - (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N - [(1R) -l, 2,3,4-tetrahydronaphthalene-1-one yl] -l, 3-thiazole-4-carboxamide, (15.086) N-methyl-2- (1- {[5-methyl-3- (trifluoromethyl) -1 H -pyrazol-1-yl] acetyl} piperidine 4-yl) -N- [(1S) -1, 2,3, 4-tetrahydronaphthalene-1-yl] -1,3-thiazole-4-carboxamide, (15.087) {6 - [({[(1R)] methyl-lH-tetrazol-5-yl) (phenyl) methylene len] amino} oxy) methyl] pyridin-2-yl} - ■ carbamidsäurepentylester (15,088) phenazine 1-carboxylic acid, (15,089) quinolin-8-ol , (15,090) quinoline-8-olsulfate (2: 1), (15,091) {6 - [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] _, amino} -oxy) methyl] pyridin-2-yl} carbamic acid tert. butyl ester, (15,092) (5-bromo-2-methoxy-4-methyl _, pyridm-3-yl) (2,3,4-trimethoxy-6-methylphenyl) methanone, (15,093) N- [2- ( 4- {[3- (4-chlorophenyl) prop-2-yn-1-yl] oxy} -3-methoxyphenyl) ethyl] -N2- (methylsulfonyl) valinamide,
(15.094) 4-Oxo-4-[(2-phenylethyl)amino]butansäure, (15.095) {6-[({[(Z)-(l -Methyl-lH-tetrazol-5- yl)(phenyl)methylen]^amino}oxy)methyl]pyridin-2-yl}carbamidsäurebut-3-in-l-ylester, (15.096) 4- Amino-5-fluor-,pyrimidin-2-ol (tautomere Form: 4-Amino-5-fluorpyrimidin-2(lH)-on), (15.097) 3,4,5- Trihydroxybenzoesäurepropylester, (15.098) [3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (15.099) (S)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (15.100) (R)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (15.101) 2-Fluor-6-(trifluormethyl)-N-(l ,l,3-trimethyl-2,3-dihydro- lH-inden-4-yl)benzamid, (15.102) 2-(6-Benzylpyridin-2-yl)chinazolin, (15.103) 2-[6-(3-Fluor-4- methoxyphenyl)-5-methylpyridin-2-yl]chinazolin, (15.104) 3-(4,4-Difluor-3,3-dimethyl-3,4- dihydroisochinolin-l -yl)chinolin, (15.105) Abscisinsäure, (15.106) N'-[5-Brom-6-(2,3-dihydro-lH- inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamid, (15.107) N'- {5-Brom-6-[l - (3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamid, (15.108) N'- {5- Brom-6-[(lR)-l -(3,5-difluo^henyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.109) N'- {5-Brom-6-[(l S)-l -(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl} -N-ethyl-N- methylimidoformamid, (15.110) N'- {5-Brom-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3- yl} -N-ethyl-N-methylimidoformamid, (15.111) N'- {5-Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2- methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.112) N-Cyclopropyl-3-(difluormethyl)-5- fluor-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid, (15.113) N-Cyclopropyl-N-(2- cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (15.114) N-(2-tert.- Butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (15.115) N- (5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (15.116) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-(15,094) 4-Oxo-4 - [(2-phenylethyl) amino] butanoic acid, (15,095) {6 - [({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) -methylene] ] ^ amino} oxy) methyl] pyridin-2-yl} -carbamic acid but-3-yn-1-yl ester, (15.096) 4-amino-5-fluoro , pyrimidin-2-ol (tautomeric form: 4-amino-5 -fluoropyrimidin-2 (1H) -one), (15,097) 3,4,5-trihydroxybenzoic acid propyl ester, (15,098) [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -l, 2-oxazol-4-yl] (pyridin-3-yl) -methanol, (15.099) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1, 2 - oxazol-4-yl] (pyridin-3-yl) -methanol, (15.100) (R) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -l, 2- oxazol-4-yl] (pyridin-3-yl) -methanol, (15.101) 2-fluoro-6- (trifluoromethyl) -N- (1,1,3-trimethyl-2,3-dihydro-1H-indene-4 -yl) benzamide, (15.102) 2- (6-Benzylpyridin-2-yl) quinazoline, (15.103) 2- [6- (3-Fluoro-4-methoxyphenyl) -5-methylpyridin-2-yl] quinazoline, ( 15.104) 3- (4,4-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.105) abscisic acid, (15.106) N '- [5-bromo-6- (2, 3-dihydro-1H-inden-2-ylo xy) -2-methylpyridin-3-yl] -N-ethyl-N-methylimidoformamide, (15.107) N '- {5-bromo-6- [1- (3,5-difluorophenyl) ethoxy] -2-methylpyridine 3-yl} -N-ethyl-N-methylimidoformamide, (15.108) N '- {5-bromo-6 - [(1R) -1- (3,5-difluoroethylenedioxy] -2-methylpyridine-3 -yl} -N-ethyl-N-methylimidoformamide, (15.109) N '- {5-bromo-6 - [(1S) -1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N-methylimidoformamide, (15.110) N '- {5-bromo-6 - [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide , (15.111) N'- {5-bromo-6 - [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.112) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -l-methyl-1H-pyrazole-4-carboxamide, (15.113) N-cyclopropyl-N- (2-cyclopropylbenzyl) -3- (difluoromethyl) - 5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.114) N- (2-tert-butylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H pyrazole-4-carboxamide, (15.115) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethane ethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.116) N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-one methyl-lH-pyrazol-
4- carboxamid, (15.117) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-l-methyl- lH-pyrazol-4-carboxamid, (15.118) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(5-fluor-2- isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid, (15.119) N-Cyclopropyl-N-(2-cyclopropyl-5- fluorbenzyl)-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (15.120) N-(2-Cyclopentyl-4-carboxamide, (15.117) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.118) N- Cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -l-methyl-1H-pyrazole-4-carboxamide, (15.119) N-cyclopropyl-N- (2-cyclopropyl- 5-fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.120) N- (2-cyclopentyl-
5- fluorbenzyl)-N-cyclopropyl-3 -(difluormethyl)-5 -fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.121) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-l -methyl-lH-pyrazol-4- carboxamid, (15.122) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-l -methyl- lH-pyrazol-4-carboxamid, (15.123) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5- methylbenzyl)-l -methyl-lH-pyrazol-4-carboxamid, (15.124) N-Cyclopropyl-N-(2-cyclopropyl-5- methylbenzyl)-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4-carboxamid, (15.125) N-(2-tert.-Butyl- 5-methylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4-carboxam (15.126) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-l -m 5-fluorobenzyl) -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.121) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.122) N-cyclopropyl-3- (difluoromethyl) N- (2-ethyl-5-methylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide; (15.123) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2 -isopropyl-5-methylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.124) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1 -methyl-1H-pyrazole-4-carboxamide, (15.125) N- (2-tert-butyl-5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole -4-carboxy (15,126) N- [5-chloro-2- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1m
carboxamid, (15.127) N-Cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl-N-[5-methyl-2-carboxamide, (15.127) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-N- [5-methyl-2-
(trifluormethyl)benzyl] - 1 H-pyrazol-4-carboxamid, (15.128) N- [2-Chlor-6-(trifluormethyl)benzyl] -N- cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4-carboxamid, (15.129) N-[3-Chlor-2- fluor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4- carboxamid, (15.130) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-l - methyl-lH-pyrazol-4-carboxamid, (15.131) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2- isopropylbenzyl)-l -methyl-lH-pyrazol-4-carbothioamid, (15.132) N'-(2,5-Dimethyl-4-phenoxyphenyl)- N-ethyl-N-methylimidoformamid, (15.133) N'- {4-[(4,5-Dichlor-l ,3-thiazol-2-yl)oxy]-2,5- dimethylphenyl} -N-ethyl-N-methylimidoformamid, (15.134) N-(4-Chlor-2,6-difluorphenyl)-4-(2-chlor- 4-fluorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.135) 9-Fluor-2,2-dimethyl-5-(chinolin-3-yl)-2,3- dihydro-l ,4-benzoxazepin, (15.136) 2- {2-Fluor-6-[(8-fluor-2-methylchinolin-3-yl)oxy]phenyl}propan- 2-ol, (15.137) 2- {2-[(7,8-Difluor-2-methylchinolin-3-yl)oxy]-6-fluorphenyl}propan-2-ol, (15.138) 4-(2- Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-l ,3-dimethyl-l H-pyrazol-5-amin, (15.139) 4-(2-Chlor-4- fluorphenyl)-N-(2,6-difluorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.140) 4-(2-Chlor-4- fluorphenyl)-N-(2-chlor-6-fluorphenyl)- 1 ,3 -dimethyl- 1 H-pyrazol-5-amin, (15.141) 4-(2-Brom-4- fluorphenyl)-N-(2-chlor-6-fluorphenyl)-l ,3-dimethyl-l H-pyrazol-5-amin, (15.142) N-(2-Brom-6- fluorphenyl)-4-(2-chlor-4-fluorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.143) 4-(2-Brom-4- fluorphenyl)-N-(2-bromphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.144) 4-(2-Brom-4-fluorphenyl)- N-(2-brom-6-fluorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.145) 4-(2-Brom-4-fluorphenyl)-N-(2- chlorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.146) N-(2-Bromphenyl)-4-(2-chlor-4-fluorphenyl)- l ,3-dimethyl-lH-pyrazol-5-amin, (15.147) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-l ,3-dimethyl- 1 H-pyrazol-5-amin, (15.148) 4-(2-Brom-4-fluorphenyl)-N-(2,6-difluorphenyl)- 1 ,3-dimethyl- 1 H- pyrazol-5-amin, (15.149) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)-l ,3-dimethyl-lH-pyrazol-5- amin, (15.150) N'-(4- {3-[(Difluormethyl)sulfanyl]phenoxy} -2,5-dimethylphenyl)-N-ethyl-N- methylimidoformamid, (15.151) N'-(2,5-Dimethyl-4- {3-[(l , 1 ,2,2-tetrafluorethyl)sulfanyl]phe- noxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.152) N'-(2,5-Dimethyl-4- {3-[(2,2,2- trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.153) N'-(2,5-Dimethyl-4- {3-[(2,2,3,3-tetrafluorpropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.154) N'- (2,5-Dimethyl-4- {3-[(pentafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.155) N'-(4- {[3-(Difluormethoxy)phenyl]sulfanyl} -2,5-dimethylphenyl)-N-ethyl-N-methyl- imidoformamid, (15.156) N'-(2,5-Dimethyl-4- { [3 -( 1 , 1 ,2,2-tetrafluorethoxy)phenyl] sulfanyl} phenyl)-N- ethyl-N-methylimidoformamid, (15.157) N'-(2,5-Dimethyl-4- {[3-(2,2,2-trifluorethoxy)phenyl]sul- fanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.158) N'-(2,5-Dimethyl-4- {[3-(2,2,3,3- tetrafluorpropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.159) N'-(2,5- Dimethyl-4- {[3-(pentafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid (15.160) 2-[3,5-Bis(difluormethylHH-pyrazoM (trifluoromethyl) benzyl] -1 H -pyrazole-4-carboxamide, (15.128) N- [2-chloro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl -lH-pyrazole-4-carboxamide, (15.129) N- [3-chloro-2-fluoro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H pyrazole-4-carboxamide, (15.130) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.131) N-Cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carbothioamide, (15.132) N '- (2,5-dimethyl- 4-phenoxyphenyl) - N-ethyl-N-methylimidoformamide, (15.133) N '- {4 - [(4,5-dichloro-l, 3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} - N-ethyl-N-methylimidoformamide, (15.134) N- (4-Chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine , (15.135) 9-Fluoro-2,2-dimethyl-5- (quinolin-3-yl) -2,3-dihydro-1,4-benzoxazepine, (15,136) 2- {2-fluoro-6 - [( 8-fluoro-2-methylquinolin-3-yl) oxy] phenyl} propan-2-ol, (15,137) 2- {2 - [(7,8-difluoro r-2-methylquinolin-3-yl) oxy] -6-fluorophenyl} -propan-2-ol, (15.138) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -l, 3 dimethyl-1H-pyrazol-5-amine, (15.139) 4- (2-chloro-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (15.140) 4- (2-Chloro-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.141) 4- (2- Bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15,142) N- (2-bromo-6-fluorophenyl) -4 (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.143) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (15.144) 4- (2-bromo-4-fluorophenyl) -N- (2-bromo-6-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5 -amine, (15.145) 4- (2-bromo-4-fluorophenyl) -N- (2-chlorophenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (15.146) N- (2-bromophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.147) 4- (2-chloro-4-fluorophenyl) -N- (2-chlorophenyl) - 1,3-dimethyl-1H-pyrazol-5-amine, (15.148) 4- (2-bromo-4-fluorophenyl) -N- (2, 6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.149) 4- (2-bromo-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl-1H pyrazole-5-amine, (15.150) N '- (4- {3 - [(difluoromethyl) sulfanyl] phenoxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (15.151) N' - ( 2,5-Dimethyl-4- {3 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.152) N '- (2.5 -Dimethyl-4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.153) N '- (2,5-dimethyl-4- {3 - [(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.154) N '- (2,5-dimethyl-4- {3 - [(pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.155) N '- (4- {[3- (difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N-ethyl-N-methyl - imidoformamide, (15.156) N '- (2,5-Dimethyl-4- {[3- (1,1,2,2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.157) N '- (2,5-dimethyl-4- {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.158) N' - (2 , 5-Dimethyl-4- {[3- (2,2,3,3-tetrafluoropropoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15,159) N '- (2,5-dimethyl) 4- {[3- (pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide (15.160) 2- [3,5-bis (difluoromethylHH-pyrazole .M
oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.161) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l- yl] -[4-(4- {5-[2-fluor-6-(prop-2 n-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2- yl)piperidin-l-yl]ethanon, (15.162) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l -[4-(4- {5-[2-chlor-6- (prop-2-in- 1 -yloxy)phenyl] -4,5-dihydro- 1 ,2-oxazol-3-yl} - 1 ,3-thiazol-2-yl)piperidin- 1 -yl]ethanon, (15.163) 2- {3-[2-(l- {[3,5-Bis(difluormethyl)-lH-pyrazol-l^^^ oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.161) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] - [ 4- (4- {5- [2-fluoro-6- (prop-2-nylloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazole-2 - yl) piperidin-1-yl] ethanone, (15.162) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1 - [4- (4- {5- [2-chloro -6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidine-1-yl] ethanone, (15.163) 2- {3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazole]
4,5-dihydro-l,2-oxazol-5-yl}phenylmethansulfonat, (15.164) 2- {3-[2-(l- {[3,5-Bis(difluormethyl)-lH- pyrazol-l-yl]_,acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3- chlorphenylmethansulfonat, (15.165) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4- {(5S)-5-[2- (prop-2-in- 1 -yloxy)phenyl] -4,5-dihydro- 1 ,2-oxazol-3-yl} - 1 ,3-thiazol-2-yl)piperidin- 1 -yl]ethanon,4,5-dihydro-l, 2-oxazol-5-yl} phenylmethanesulfonate, (15.164) 2- {3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl ] _, acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-l, 2-oxazol-5-yl} -3-chlorophenylmethanesulfonate, (15.165) 2- [ 3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4-{(5S) -5- [2- (prop-2-yn-1-ynyloxy) phenyl] - 4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidine-1-yl] ethanone,
(15.166) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4- {(5R)-5-[2-(prop-2-in-l-yloxy)phenyl]- 4,5-dihydro-l ,2-oxazol-3-yl} -1 ,3-thiazol-2-yl)piperidin-l -yl]ethanon, (15.167) 2-[3,5-Bis(difluor- methyl)-lH-pyrazol-l-yl]-l-[4-(4- {(5S)-5-[2-fluor-6-(prop-2-in-l -yloxy)phenyl]-4,5-dihydro-l,2- oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.168) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l- yl]-l-[4-(4- {(5R)-5-[2-fluor-6-(prop-2-in-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl} -l,3-thiazol-2- yl)piperidin-l-yl]ethanon, (15.169) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4- {(5S)-5-[2- chlor-6-(prop-2-in-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl} -l,3-thiazol-2-yl)piperidin-l- yl]ethanon, (15.170) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4- {(5R)-5-[2-chlor-6-(prop-2-in- l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.171) 2- {(5S)-3-[2-(l- {[3,5-Bis(difluomethyl)-lH-pyr (15.166) 2- [3,5-Bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4-{(5R) -5- [2- (prop-2-yn-1 -yloxy) phenyl] - 4,5-dihydro-l, 2-oxazol-3-yl} -1, 3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.167) 2- [3.5 Bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4-{(5S) -5- [2-fluoro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-l, 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.168) 2- [3,5-bis ( difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4-{(5R) -5- [2-fluoro-6- (prop-2-yn-1-yloxy) phenyl] -4, 5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.169) 2- [3,5-bis (difluoromethyl) -lH- pyrazol-1-yl] -1- [4- (4- {(5S) -5- [2-chloro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1 , 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.170) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl ] 1- [4- (4- {(5R) -5- [2-chloro-6- (prop-2-yl-yloxy) -phenyl] -4,5-dihydro-1,2-oxazole 3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.171) 2- {(5S) -3- [2- (1 - {[3,5-bis (difluomethyl ) -lH-pyr
dihydro-l,2-oxazol-5-yl}phenylmethansulfonat, (15.172) 2- {(5R)-3-[2-(l- {[3,5-Bis(difluormethyl)-lH- pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}phenylmethansul- fonat, (15.173) 2- {(5S)-3-[2-(l- {[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3- thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl} -3-chlorphenylmethansulfonat, (15.174) 2- {(5R)-3-[2-(l- {[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro oxazol-5 -yl} -3 -chlorphenylmethansulfonat. dihydro-l, 2-oxazol-5-yl} phenylmethanesulfonate, (15.172) 2- {(5R) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl ] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-l, 2-oxazol-5-yl} phenylmethanesulphonate, (15.173) 2- {(5S) -3- [2- (1 - {(3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4, 5-dihydro-l, 2-oxazol-5-yl} -3-chlorophenylmethanesulfonate, (15.174) 2- {(5R) -3- [2- (1 - {[3,5-bis (difluoromethyl) -lH- pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydrooxazol-5-yl-3-chlorophenyl methanesulfonate.
Biologische Schädlingsbekämpfungsmittel als Mischungspartner Biological pesticides as a mix partner
Die Verbindungen der Formel (I) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden. Biologische Schädlingsbekämpfungsmittel umfassen insbesondere Bakterien, Pilze, Hefen, Pflanzenextrakte, und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte. The compounds of formula (I) may be combined with biological pesticides. Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms, including proteins and secondary metabolites.
Biologische Schädlingsbekämpfungsmittel umfassen Bakterien wie sporenbildende Bakterien, wurzelbesiedelnde Bakterien und Bakterien, die als biologische Insektizide, Fungizide oder Nematizide wirken. Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
Beispiele für solche Bakterien, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of such bacteria which can be used as biological pesticides are:
Bacillus amyloliquefaciens, Stamm FZB42 (DSM 231179), oder Bacillus cereus, insbesondere B. cereus Stamm CNCM 1-1562 oder Bacillus firmus, Stamm 1-1582 (Accession number CNCM 1-1582) oder Bacillus pumilus, insbesondere Stamm GB34 (Accession No. ATCC 700814) und Stamm QST2808 (Accession No. NRRL B-30087), oder Bacillus subtilis, insbesondere Stamm GB03 (Accession No. ATCC SD-1397), oder Bacillus subtilis Stamm QST713 (Accession No. NRRL B-21661) oder Bacillus subtilis Stamm OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, insbesondere B. thuringiensis subspecies israelensis (serotype H-14), Stamm AM65-52 (Accession No. ATCC 1276), oder B. thuringiensis subsp. aizawai, insbesondere Stamm ABTS- 1857 (SD-1372), oder B. thuringiensis subsp. kurstaki Stamm HD-1, oder B. thuringiensis subsp. tenebrionis Stamm NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus Stamm AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Stamm AQ 6047 (Acession Number NRRL 30232). Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) -PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Accession Number NRRL 30232).
Beispiele für Pilze und Hefen, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of fungi and yeasts which can be used as biological pesticides are:
Beauveria bassiana, insbesondere Stamm ATCC 74040, Coniothyrium minitans, insbesondere Stamm CON/M/91-8 (Accession No. DSM-9660), Lecanicillium spp., insbesondere Stamm HRO LEC 12, Lecanicillium lecanii, (ehemals bekannt als Verticillium lecanii), insbesondere Stamm KV01, Metarhizium anisopliae, insbesondere Stamm F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, insbesondere Stamm NRRL Y-30752, Paecilomyces fumosoroseus (neu: Isaria fümosorosea), insbesondere Stamm IFPC 200613, oder Stamm Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, insbesondere P. lilacinus Stamm 251 (AGAL 89/030550), Talaromyces flavus, insbesondere Stamm VI 17b, Trichoderma atroviride, insbesondere Stamm SCI (Accession Number CBS 122089), Trichoderma harzianum, insbesondere T. harzianum rifai T39. (Accession Number CNCM 1-952). Beauveria bassiana, especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Adoxophyes orana (Apfelschalenwickler) Granulosevirus (GV), Cydia pomonella (Apfelwickler) Granulosevirus (GV), Helicoverpa armigera (Baumwollkapselwurm) Nuklear Polyhedrosis Virus (NPV), Spodoptera exigua (Zuckerrübeneule) mNPV, Spodoptera frugiperda (Heerwurm) mNPV, Spodoptera littoralis (Afrikanischer Baumwollwurm) NPV. Es sind auch Bakterien und Pilze umfasst, die als ,Inokulant' Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt: Examples of viruses that can be used or used as biological pesticides are: Adoxophyes orana (Apple peel winder) Granulosis virus (GV), Cydia pomonella (codling moth) Granulosis virus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus (NPV), Spodoptera exigua (mNPV), Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis (African Cotton worm) NPV. It also includes bacteria and fungi that are added as 'inoculant' plants or parts of plants or plant organs and promote by their special properties, plant growth and plant health. Examples are:
Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., insbesondere Burkholderia cepacia (ehemals bekannt als Pseudomonas cepacia), Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.. Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp. Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.
Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of plant extracts and those products formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense,Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Saponinextrakt), Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,„Requiem™ Insecticide", Rotenon, Ryania/Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen-Extrakt, insbesondere Raps- oder Senfpulver. Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, Requiem ™ Insecticide, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen extract , in particular rapeseed or mustard powder.
Safener als Mischpartner Safener as mixing partner
Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamid (CAS 129531-12-0), 4-(Dichloroacetyl)-l-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-Trimethyl-3- (dichloroacetyl)-l,3-oxazolidine (CAS 52836-31-4). Pflanzen und Pflanzenteile The compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ({4 - [(methylcarbamoyl) amino] phenyl} sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -l-oxa 4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 52836-31-4). Plants and plant parts
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen), beispielsweise Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen. According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired ones Wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybean, potato, sugar beets, sugar cane, tomatoes, peas and other vegetables, cotton, tobacco, rapeseed, and Fruit plants (with the fruits apples, pears, citrus fruits and grapes). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lager-raum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Auf^streichen, Indizieren und bei VennehrungsTnaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehr-'schichtiges Um-'hüllen. The treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, nebulizing, spreading, spreading, indexing and in the case of nutrient material, in particular in the case of seeds, by further single or multi-layered sheathing.
Wie bereits oben erwähnt können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden wie Kreuzung oder Protoplastenfusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff„Teile" bzw.„Teile von Pflanzen" oder„Pflanzenteile" wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "parts of plants" has been explained above.Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.PV plants are understood as meaning plants with new properties ("traits") have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
Transgene Pflanze, Saatgutbehandlung und Integrationsereignisse Transgenic plant, seed treatment and integration events
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gen-techno^logisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gen-techno- logische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegen-'über hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungs-wert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernte-produkte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehrfähigkeit der Pflanzen gegen tierische und mikrobielle Schädlinge, wie Insekten, Spinnentiere, Nematoden, Milben, Schnecken, bewirkt z.B. durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z.B. durch die Gene CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden, ferner eine erhöhte Abwehrfähigkeit der Pflanzen gegen pflanzenpathogene Pilze, Bakterien und/oder Viren, bewirkt z.B. durch Systemisch Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine, sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe, beispielsweise Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Weizen, Reis, Kartoffel, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehrfähigkeit der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken. The preferred plants or plant cultivars to be treated according to the invention which are to be treated include all plants which, as a result of the gene-technological modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased Tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salinity, increased flowering efficiency, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvest products. Further and particularly emphasized examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, caused for example by toxins formed in the plants, in particular those caused by the genetic material from Bacillus Thuringiensis (eg by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, also an increased resistance of the plants against Phytopathogenic fungi, bacteria and / or viruses, eg by systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, and increased tolerance of the plants against certain herbicidal active ingredients, such as imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg, "PAT" gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
Pflanzenschutz - Behandlungsarten Plant protection - types of treatment
Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, (Ver-) Spritzen, (Ver-)Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, (Ver-) Streuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen, usw. Es ist ferner möglich, die Verbindungen der Formel (I) nach dem Ultra-Low- Volume- Verfahren auszubringen oder die Anwendungsform oder die Verbindung der Formel (I) selbst in den Boden zu injizieren. The treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, evaporating, atomising, atomizing, sprinkling, foaming, brushing, spreading, injecting, pouring, drip irrigation and propagating material, in particular in the case of seeds further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to dispense the compounds of formula (I) by the ultra-low-volume method or the use form or the compound of formula ( I) inject myself into the soil.
Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d.h. Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte. Bei systemisch wirksamen Verbindungen gelangen die Verbindungen der Formel (I) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Verbindungen der Formel (I) auf den Lebensraum der Pflanze. Das kann beispielsweise durch Drenchen, Einmischen in den Boden oder die Nährlösung sein, d.h. der Standort der Pflanze (z.B. Boden oder hydroponische Systeme) wird mit einer flüssigen Form der Verbindungen der Formel (I) getränkt, oder durch die Bodenapplikation, d.h. die Verbindungen der Formel (I) werden in fester Form, (z.B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Wasserreiskulturen kann das auch durch Zudosieren der Verbindung der Formel (I) in einer festen Anwendungsform (z.B. als Granulat) in ein überflutetes Reisfeld sein. Saatgutbehandlung A preferred direct treatment of the plants is foliar application, ie compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be adjusted to the infestation pressure of the respective pest. In the case of systemically active compounds, the compounds of the formula (I) also enter the plants via the root system. The treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant. This can be, for example, by drenching, mixing in the soil or the nutrient solution, ie the location of the plant (eg soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by the soil application, ie the compounds of Formula (I) are introduced in solid form, (eg in the form of granules) in the location of the plants. In water rice crops, this may also be by metered addition of the compound of formula (I) in a solid form (eg as granules) into a flooded paddy field. seed treatment
Die Bekämpfung von tierischen Schädlingen durch die Behandlung des Saatguts von Pflanzen ist seit langem bekannt und ist Gegenstand ständiger Verbesserungen. Dennoch ergeben sich bei der Behandlung von Saatgut eine Reihe von Problemen, die nicht immer zufriedenstellend gelöst werden können. So ist es erstrebenswert, Verfahren zum Schutz des Saatguts und der keimenden Pflanze zu entwickeln, die das zusätzliche Ausbringen von Schädlingsbekämpfungsmitteln bei der Lagerung, nach der Saat oder nach dem Auflaufen der Pflanzen überflüssig machen oder zumindest deutlich verringern. Es ist weiterhin erstrebenswert, die Menge des eingesetzten Wirkstoffs dahingehend zu optimieren, dass das Saatgut und die keimende Pflanze vor dem Befall durch tierische Schädlinge bestmöglich geschützt werden, ohne jedoch die Pflanze selbst durch den eingesetzten Wirkstoff zu schädigen. Insbesondere sollten Verfahren zur Behandlung von Saatgut auch die intrinsischen Insektiziden bzw. nematiziden Eigenschaften schädlingsresistenter bzw. - toleranter transgener Pflanzen einbeziehen, um einen optimalen Schutz des Saatguts und der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen. The control of animal pests by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which eliminate or at least significantly reduce the additional application of pesticides during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment methods should also incorporate the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and germinating plant with a minimum of pesticide cost.
Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (I) behandelt wird. Das erfindungsgemäße Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen umfasst ferner ein Verfahren, in dem das Saatgut gleichzeitig in einem Vorgang oder sequentiell mit einer Verbindung der Formel (I) und Mischungspartner behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wird. The present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I). The method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (I) zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor tierischen Schädlingen. Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer Verbindung der Formel (I) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut enthalten sein. Dabei können die Schichten, die eine Verbindung der Formel (I) und Mischungspartner enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) und Mischungspartner als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. The invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I). The invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner. The invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner. In the case of seed which has been treated at different times with a compound of formula (I) and mixing partner, the individual substances may be contained in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture partners may optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating.
Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Verbindung der Formel (I) einem Filmcoating - Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden. Einer der auftretenden Vorteile, wenn eine der Verbindungen der Formel (I) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed. One of the advantages that occurs when one of the compounds of the formula (I) acts systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
Ein weiterer Vorteil ist darin zu sehen, dass durch die Behandlung des Saatguts mit einer Verbindung der Formel (I) Keimung und Auflauf des behandelten Saatguts gefördert werden können. Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt werden können. Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.
Verbindungen der Formel (I) können ferner in Kombination mit Mitteln der Signaltechnologie eingesetzt werden, wodurch eine bessere Besiedlung mit Symbionten, wie zum Beispiel Rhizobien, Mycorrhiza und/oder endophytischen Bakterien oder Pilzen, stattfindet und/oder es zu einer optimierten Stickstofffixierung kommt. Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
Die Verbindungen der Formel (I) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Getreide (z. B. Weizen, Gerste, Roggen, Hirse und Hafer), Mais, Baum-wolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z.B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, Zwiebeln und Salat), Obstpflanzen, Rasen und Zierpflanzen. Besondere Bedeutung kommt der Behandlung des Saatguts von Getreide (wie Weizen, Gerste, Roggen und Hafer), Mais, Soja, Baumwolle, Canola, Raps und Reis zu. Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere Insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikro- Organismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von trans-genem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt. Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hülle, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z.B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. Im Falle von Reissaatgut ist es auch möglich Saatgut zu verwenden, das zum Beispiel in Wasser bis zu einem bestimmten Stadium vorgequollen wurde (pigeon breast Stadium), was zu einer verbesserten Keimung und zu einem gleichmäßigeren Auflaufen führt. The compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants. Of particular importance is the treatment of seeds of cereals (such as wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice. As already mentioned above, the treatment of transgenic seed with a compound of the formula (I) is also of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide with in particular insecticidal or nematicidal properties. The heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis. In the context of the present invention, the compound of the formula (I) is applied to the seed. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp. For example, seed may be used that has been harvested, cleaned and dried to a moisture content that is storable. Alternatively, seed can also be used, which after drying, for example, was treated with water and then dried again, for example priming. In the case of rice seed, it is also possible to use seeds that have been pre-swollen in water, for example, to a certain stage (pigeon breast stage), resulting in improved germination and more even emergence.
Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge der auf das Saatgut aufgebrachten Verbindung der Formel (I) und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. In general, when treating seed, care must be taken to ensure that the amount of compound of formula (I) and / or other additives applied to the seed is not such as to affect the germination of the seed or to damage the resulting plant becomes. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.
Die Verbindungen der Formel (I) werden in der Regel in Form einer geeigneten Formulierung auf das Saatgut aufgebracht. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt. The compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
Die Verbindungen der Formel (I) können in die üblichen Beizmittel-Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen. The compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, indem man Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. These formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solution or Diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
Als Farbstoffe, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.I. Pigment Red 112 und C.I. Solvent Red 1 bekannten Farbstoffe. Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutyl-naphthalin-Sulfonate. Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Beizmittel- Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vor-zugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid Blockpolymere, Alkylphenolpolyglykolether sowie Tri- stryrylphenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat- Formaldehydkondensate. Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
Als Entschäumer können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat. Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably usable are silicone defoamers and magnesium stearate.
Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal. Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
Als Kleber, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline AI, A3 (= Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler „Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401- 412). Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. Gibberellins which may be present in the seed dressing formulations which can be used in accordance with the invention are preferably the gibberellins AI, A3 (= gibberellic acid), A4 and A7, particularly preferably gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, pp. 401-412).
Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen können entweder direkt oder nach vorherigem Verdünnen mit Wasser zur Behandlung von Saatgut der verschiedensten Art eingesetzt werden. So lassen sich die Konzentrate oder die daraus durch Verdünnen mit Wasser erhältlichen Zubereitungen einsetzen zur Beizung des Saatgutes von Getreide, wie Weizen, Gerste, Roggen, Hafer und Triticale, sowie des Saatgutes von Mais, Reis, Raps, Erbsen, Bohnen, Baumwolle, Sonnenblumen, Soja und Rüben oder auch von Gemüsesaatgut der verschiedensten Natur. Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder deren verdünnte Anwendungsformen können auch zum Beizen von Saatgut transgener Pflanzen eingesetzt werden. The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds. Thus, the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature. The seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder daraus hergestellten Anwendungsformen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer im diskontinuierlichem oder kontinuierlichem Betrieb gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungsvorgang an. For the treatment of seed with the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom, all mixing devices which can usually be used for the dressing can be considered. Specifically, the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed. Optionally, a drying process follows.
Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formulierungen kann inner-halb eines größeren Bereiches variiert werden. Sie richtet sich nach dem jeweiligen Gehalt der Verbindungen der Formel (I) in den Formulierungen und nach dem Saatgut. Die Aufwandmengen bei der Verbindung der Formel (I) liegen im Allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 15 g pro Kilogramm Saatgut. The application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed. The application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
Tiergesundheit animal Health
Auf dem Gebiet der Tiergesundheit, d.h. dem Gebiet der Tiermedizin, sind die Verbindungen der Formel (I) gegen Tierparasiten, insbesondere Ektoparasiten oder Endoparasiten, wirksam. Der Begriff Endoparasiten umfasst insbesondere Helminthen und Protozoa wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten und Akariden. In the field of animal health, i. In the veterinary field, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects and acarids.
Auf dem Gebiet der Tiermedizin eignen sich die Verbindungen der Formel (I), die eine günstige Toxizität gegenüber Warmblütern aufweisen, für die Bekämpfung von Parasiten, die in der Tierzucht und Tierhaltung bei Nutztieren, Zuchttieren, Zootieren, Laboratoriumstieren, Versuchstieren und Haustieren auftreten. Sie sind gegen alle oder einzelne Entwicklungsstadien der Parasiten wirksam. In the field of veterinary medicine, the compounds of formula (I), which have a favorable toxicity to warm-blooded animals, are suitable for the control of parasites used in animal breeding and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and pets occur. They are effective against all or individual stages of parasite development.
Zu den landwirtschaftlichen Nutztieren zählen zum Beispiel Säugetiere wie Schafe, Ziegen, Pferde, Esel, Kamele, Büffel, Kaninchen, Rentiere, Damhirsche und insbesondere Rinder und Schweine; Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; Fische und Krustentiere, z.B. in der Aquakultur und auch Insekten wie Bienen. Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and shellfish, e.g. in aquaculture and also insects like bees.
Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel, Reptilien, Amphibien und Aquariumfische. Gemäß einer bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Säugetiere verabreicht. The domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians and aquarium fish. In a preferred embodiment, the compounds of formula (I) are administered to mammals.
Gemäß einer weiteren bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel und insbesondere Geflügel, verabreicht. According to a further preferred embodiment, the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
Durch Verwendung der Verbindungen der Formel (I) für die Bekämpfung von Tierparasiten sollen Krankheit, Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig und dergleichen) verringert bzw. vorgebeugt werden, so dass eine wirtschaftlichere und einfachere Tierhaltung ermöglicht wird und ein besseres Wohlbefinden der Tiere erzielbar ist. By using the compounds of formula (I) for the control of animal parasites disease, deaths and reductions (in meat, milk, wool, hides, eggs, honey and the like) are to be reduced or prevented, so that a more economical and easier animal husbandry allows and a better well-being of the animals is achievable.
In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen", dass durch die Verbindungen der Formel (I) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert werden kann. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindung der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern kann. With regard to the field of animal health, the term "control" or "combat" means that the compounds of formula (I) effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent can. More specifically, "combating" in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication.
Zu den Arthropoden zählen: aus der Ordnung Anoplurida, zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina and Ischnocerina, zum Beispiel Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilla spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; aus der Ordnung Siphonapterida, zum Beispiel Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Triatoma spp., R odnius spp., Panstrongylus spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida. The arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia Spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp. , Fannia spp., Glossina spp., Calliphora spp., Lucilla spp., Chrysomyia Spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp .; from the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .; from the order Heteropterida, for example Cimex spp., Triatoma spp., R odnius spp., Panstrongylus spp .; as well as pests and hygiene pests from the order Blattarida.
Weiterhin zählen zu den Arthropoden: Furthermore, the arthropods include:
Aus der Unterklasse Akari (Acarina) und der Ordnung Metastigmata, zum Beispiel aus der Familie Argasidae, wie Argas spp., Omithodorus spp., Otobius spp., aus der Familie Ixodidae, wie Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; aus der Ordnung Actinedida (Prostigmata), zum Beispiel Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp.; und aus der Ordnung Acaridida (Astigmata), zum Beispiel Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.. From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Omithodorus spp., Otobius spp., From the family Ixodidae, such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the original genus of multi-pronged ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp .; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp. , Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
Zu parasitären Protozoen zählen: Parasitic protozoa include:
Mastigophora (Flagellata), wie zum Beispiel Trypanosomatidae, zum Beispiel Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, wie zum Beispiel Trichomonadidae, zum Beispiel Giardia lamblia, G. canis; Mastigophora (Flagellata), such as Trypanosomatidae, for example Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, such as Trichomonadidae, for example Giardia lamblia, G. canis;
Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba histolytica, Hartmanellidae, zum Beispiel Acanthamoeba sp., Harmanella sp.; Apicomplexa (Sporozoa), wie Eimeridae, zum Beispiel Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis,Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .; Apicomplexa (Sporozoa), such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis,
E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media, E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans,E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E.media, E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E.ovis, E.parva, E.pavonis, E. perforans,
E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec, E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec, Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec, I. suis, Cystisospora spec, Cryptosporidium spec, insbesondere C. parvum; wie Toxoplasmadidae, zum Beispiel Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; wie Sarcocystidae, zum Beispiel Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec, S. suihominis, wie Leucozoidae, zum Beispiel Leucozytozoon simondi, wie Plasmodiidae, zum Beispiel Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P. vivax, P. spec, wie Piroplasmea, zum Beispiel Babesia argentina, B. bovis, B. canis, B. spec, Theileria parva, Theileria spec, wie Adeleina, zum Beispiel Hepatozoon canis, H. spec. E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E.spec, E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec., In particular C. parvum; as Toxoplasmadidae, for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; such as Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P.spec, such as piroplasmea, for example Babesia argentina, B.bovis, B.canis, B.spec, Theileriaparva, Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec.
Zu pathogenen Endoparasiten, bei denen es sich um Helminthen handelt, zählen Plattwürmer (z.B. Monogenea, Cestodes und Trematodes), Rundwürmer, Acanthocephala und Pentastoma. Dazu zählen: Pathogenic endoparasites, which are helminths, include flatworms (e.g., Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include:
Monogenea: z.B.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.; Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.; aus der Ordnung Cyclophyllida zum Beispiel: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.; Monogenea: e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .; Cestodes: from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp. , Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
Trematodes: aus der Klasse Digenea zum Beispiel: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp.; Trematodes: from the genus Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp. , Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp .;
Rundwürmer: Trichinellida zum Beispiel: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp.; aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Strongyloides spp.; aus der Ordnung Rhabditida zum Beispiel: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.; aus der Ordnung Spirurida zum Beispiel: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.; Roundworms: Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp .; from the order Tylenchida for example: Micronema spp., Strongyloides spp .; from the order Rhabditida, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp. , Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp , Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp .; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp .; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp .; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp .;
Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp.; aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.; Acanthocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp.. Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch oder therapeutisch erfolgen. Pentastoma: from the order Porocephalida for example Linguatula spp .. In the field of veterinary medicine and animal husbandry, the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. The administration can be prophylactic or therapeutic.
So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verwendung einer Verbindung der Formel (I) als Arzneimittel. Ein weiterer Aspekt bezieht sich auf die Verwendung einer Verbindung der Formel (I) als Antiendoparasitikum, insbesondere als ein Helminthizid oder ein Mittel gegen Protozoen. Verbindungen der Formel (I) eignen sich für die Verwendung als Antiendoparasitikum, insbesondere als ein Helminthizid oder Mittel gegen Protozoen, beispielsweise in der Tierzucht, in der Tierhaltung, in Ställen und auf dem Hygienesektor. Ein weiterer Aspekt wiederum betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder ein Akarizid Ein weiterer Aspekt betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder Akarizid, zum Beispiel in der Tierhaltung, in der Tierzucht, in Ställen oder auf dem Hygienesektor. Thus, one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament. Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent. Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector. A further aspect in turn relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide. Another aspect relates to the use of a compound of the formula (I) as anticancer drug, in particular an arthropodicide such as an insecticide or acaricide, for example in animal husbandry, in animal husbandry, in stables or in the hygiene sector.
Vektorkontrolle vector control
Die Verbindungen der Formel (I) können auch in der Vektorkontrolle eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arachnide, der in der Lage ist, Krankheitserreger wie z. B. Viren, Würmer, Einzeller und Bakterien aus einem Reservoir (Pflanze, Tier, Mensch, etc.) auf einen Wirt zu übertragen. Die Krankheitserreger können entweder mechanisch (z.B. Trachoma durch nicht-stechende Fliegen) auf einem Wirt, oder nach Injektion (z.B. Malaria-Parasiten durch Mücken) in einen Wirt übertragen werden. Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: The compounds of formula (I) can also be used in vector control. A vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such. As viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer. The pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes). Examples of vectors and their transmitted diseases or pathogens are:
1) Mücken 1) mosquitoes
- Anopheles: Malaria, Filariose; - Anopheles: malaria, filariasis;
- Culex: Japanische Encephalitis, Filariasis, weitere virale Erkrankungen, Übertragung von Würmern; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of worms;
- Aedes: Gelbfieber, Dengue-Fieber, Filariasis, weitere virale Erkrankungen; - Simulien: Übertragung von Würmern insbesondere Onchocerca volvulus; - Aedes: yellow fever, dengue fever, filariasis, other viral diseases; - Simulia: transmission of worms, in particular Onchocerca volvulus;
2) Läuse: Hautinfektionen, Fleckfieber (epidemic typhus); 2) lice: skin infections, typhus (epidemic typhus);
3) Flöhe: Pest, endemisches Fleckfieber; 3) Fleas: plague, endemic typhus fever;
4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
5) Milben: Acariose, Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis-Enzephalitis, virale Hirnhautentzündung (FSME), Krim-Kongo-Fieber, Borreliose; 5) mites: acariosis, typhus, rickettsipox, tularemia, Saint-Louis encephalitis, viral meningitis (TBE), Crimean Congo fever, Lyme disease;
6) Zecken: Borelliosen wie Borrelia duttoni, Frühsommer-Meningoenzephalitis, Q-Fieber (Coxiella burnetii), Babesien (Babesia canis canis). 6) Ticks: Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).
Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten wie Aphiden, Fliegen, Zikaden oder Thripse, die Pflanzenviren auf Pflanzen übertragen können. Weitere Vektoren, die Pflanzenviren übertragen können, sind Spinnmilben, Läuse, Käfer und Nematoden. Examples of vectors in the context of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
Weitere Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten und Arachniden wie Mücken, insbesondere der Gattungen Aedes, Anopheles, z.B. A. gambiae, A. arabiensis, A. funestus, A. dirus (Malaria) und Culex, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können. Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
Eine Vektorkontrolle ist auch möglich, wenn die Verbindungen der Formel (I) Resistenz-brechend sind. Vector control is also possible when the compounds of formula (I) are resistance-disrupting.
Verbindungen der Formel (I) sind zur Verwendung in der Prävention von Krankheiten bzw. vor Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) zur Vektorkontrolle, z.B. in der Landwirtschaft, im Gartenbau, in Forsten, in Gärten und Freizeiteinrichtungen sowie im Vorratsund Materialschutz. Compounds of formula (I) are suitable for use in the prevention of disease or pathogens transmitted by vectors. Thus, another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials.
Schutz von technischen Materialen Die Verbindungen der Formel (I) eignen sich zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten, z.B. aus der Ordnung Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma. Protection of Engineering Materials The compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt. Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints. The application of the invention for the protection of wood is particularly preferred.
In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. In a further embodiment, the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
In einer weiteren Ausführungsform liegen die Verbindungen der Formel (I) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d.h., es kann ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder als Fungizide kommen insbesondere die oben genannten in Frage. In a further embodiment, the compounds of formula (I) are present as a ready-to-use pest control agent, that is, it can be applied to the corresponding material without further changes. As further insecticides or as fungicides in particular the above-mentioned in question.
Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, verwendet werden können. Gleichfalls können die Verbindungen der Formel (I) allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden. Surprisingly, it has also been found that the compounds of the formula (I) can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water. Likewise, the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
Bekämpfung von tierischen Schädlingen auf dem Hygienesektor Control of animal pests in the hygiene sector
Die Verbindungen der Formel (I) eignen sich zur Bekämpfung von tierischen Schädlingen auf dem Hygienesektor. Insbesondere kann die Erfindung im Haushalts-, Hygiene- und Vorratsschutz verwendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen vorkommen. Zur Bekämpfung der tierischen Schädlinge werden die Verbindungen der Formel (I) allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie in Haushaltsinsektizid-Produkten verwendet. Die Verbindungen der Formel (I) sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. The compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, in closed Rooms, such as homes, factories, offices, vehicle cabs occur. To combat animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients. Preferably, they are used in household insecticide products. The compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
Zu diesen Schädlingen gehören beispielsweise Schädlinge aus der Klasse Arachnida, aus den Ordnungen Scorpiones, Araneae und Opiliones, aus den Klassen Chilopoda und Diplopoda, aus der Klasse Insecta die Ordnung Blattodea, aus den Ordnungen Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda. These pests include, for example, pests of the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
Die Anwendung erfolgt beispielsweise in Aerosolen, drucklosen Sprühmitteln, z.B. Pump- und Zerstäubersprays, Nebelautomaten, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. Application is for example in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cushions and moth gels, as granules or dusts, in litter or bait stations.
Erläuterung der Verfahren und Zwischenprodukte Explanation of processes and intermediates
Die folgenden Herstellungs- und Verwendungsbeispiele illustrieren die Erfindung, ohne sie zu beschränken. Die Produkte wurden mittels 'H-NMR Spektroskopie und/oder LC/MS (Liquid Chromatography Mass Spectrometry) charakterisiert. The following examples of preparation and use illustrate the invention without limiting it. The products were characterized by 'H-NMR spectroscopy and / or LC / MS (Liquid Chromatography Mass Spectrometry).
Die Bestimmung der logP Werte erfolgte gemäß OECD Guideline 117 (EC Directive 92/69/EEC) durch HPLC (High Performance Liquid Chromatography) an reversed-phase (RP) Säulen (C18), mit nachfolgenden Methoden: The determination of the logP values was carried out according to OECD Guideline 117 (EC Directive 92/69 / EEC) by HPLC (High Performance Liquid Chromatography) on reversed-phase (RP) columns (C18), using the following methods:
[a] Die Bestimmung mit der LC-MS im sauren Bereich erfolgt bei pH 2,7 mit 0,1 % wässriger Ameisensäure und Acetonitril (enthält 0,1% Ameisensäure) als Eluenten; linearer Gradient von 10%[a] The determination with the LC-MS in the acidic range is carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid) as eluent; linear gradient of 10%
Acetonitril bis 95% Acetonitril. Acetonitrile to 95% acetonitrile.
[b] Die Bestimmung mit der LC-MS im neutralen Bereich erfolgt bei pH 7.8 mit 0,001 molarer wässriger Ammoniumhydrogencarbonat-Lösung und Acetonitril als Eluenten; linearer Gradient von 10%) Acetonitril bis 95% Acetonitril. Die Eichung erfolgt mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP- Werte bekannt sind (Bestimmung der logP-Werte anhand der Retentionszeiten durch lineare Interpolation zwischen zwei aufeinander folgenden Alkanonen). Die NMR- Spektren wurden mit einem Broker Avance 400, ausgestattet mit einem Durchflussprobenkopf (60 μΐ Volumen), bestimmt. In Einzelfällen wurden die NMR Spektren mit einem Broker Avance II 600 gemessen. [b] The determination with the LC-MS in the neutral range is carried out at pH 7.8 with 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as eluent; linear gradient of 10%) acetonitrile to 95% acetonitrile. The calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones). The NMR spectra were determined with an Avance 400 broker equipped with a 60 μΐ volume flowhead probe. In individual cases, the NMR spectra were measured with a broker Avance II 600.
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) Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektroms 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 peak list of an example therefore has the form: δι (intensity ^; 82 (intensity 2);; δ; (intensity ^;; δ η (intensity n )) 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 For broad signals, several peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.
Zur Kalibrierung der chemischen Verschiebung von IH-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 IH-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 1H-NMR-Peaks sind ähnlich den klassischen 1H-NMR- Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. Darüber hinaus können sie wie klassische 1H-NMR- Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. The lists of 1H NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation. In addition, they can, like classical 1H-NMR prints solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities.
Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 1H-NMR-Peaks die gewöhnlichen Lösungsmitte lpeaks, zum Beispiel Peaks von DMSO in DMSO-DÖ 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 1H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D δ and the peak of water, usually on 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 Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von "Nebenprodukt-Fingerabdrucken" zu erkennen. 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 the particular preparation process. Their peaks can thus help to detect the reproduction of our 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 IH-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Further details on IH NMR peaks can be found in Research Disclosure Database Number 564025.
Synthese von Benzothiazolen der Formel (I) nach Methode A Synthesis of benzothiazoles of the formula (I) according to method A.
6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1) 6-Bromo-2- (pyridin-3-yl) -1,3-benzothiazole (I-a-1)
Schritt 1: N-(4-Brom-2-fluorphenyl)nicotinamid (A-III-1) Step 1: N- (4-Bromo-2-fluorophenyl) nicotinamide (A-III-1)
16,3 g (85,9 mmol) 4-Brom-2-fluoranilin wurden in 200 ml Pyridin gelöst, im Eisbad abgekühlt und portionsweise mit 16,5 g (92,7 mmol) 3-(Chlorcarbonyl)pyridiniumchlorid versetzt. Der Ansatz wurde auf Raumtemperatur erwärmt, am Rotationsverdampfer im lauwarmen Wasserbad für 20 Minuten gedreht und anschließend im Vakuum eingedampft. Der erhaltene Rückstand wurde mit Wasser und wässriger Ammoniaklösung versetzt und der ausfallende Feststoff abgesaugt. Dieser wurde noch mit wässriger Ammoniaklösung, Wasser und Petrolether gewaschen und getrocknet. Man erhielt so 25,9 g (100 % Reinheit, 94,5 % d. Th.) der Titelverbindung (A-III-1). 16.3 g (85.9 mmol) of 4-bromo-2-fluoroaniline were dissolved in 200 ml of pyridine, cooled in an ice bath and treated portionwise with 16.5 g (92.7 mmol) of 3- (chlorocarbonyl) pyridinium chloride. The batch was warmed to room temperature, rotated on a rotary evaporator in a lukewarm water bath for 20 minutes and then evaporated in vacuo. The residue obtained was mixed with water and aqueous ammonia solution and the precipitated solid was filtered off with suction. This was washed with aqueous ammonia solution, water and petroleum ether and dried. This gave 25.9 g (100% purity, 94.5% of theory) of the title compound (A-III-1).
1H-NMR (399,9 MHz, d6-DMSO): δ = 10,424 (13,4); 9,112 (13,1); 9,108 (13,1); 8,790 (10,3); 8,786 (11,0); 8,778 (11,0); 8,774 (10,8); 8,315 (5,8); 8,310 (8,0); 8,305 (5,8); 8,295 (6,2); 8,290 (8,5); 8,286 (5,9); 7,690 (9,5); 7,685 (9,9); 7,665 (9,6); 7,659 (10,3); 7,654 (8,2); 7,633 (16,0); 7,612 (9,9); 7,595 (7,6); 7,594 (7,6); 7,583 (7,4); 7,582 (7,5); 7,576 (7,3); 7,574 (7,2); 7,564 (7,0); 7,562 (7,0); 7,479 (7,4); 7,477 (8,1); 7,474 (7,5); 7,472 (7,1); 7,458 (5,8); 7,455 (6,3); 7,453 (5,9); 7,450 (5,6); 7,401 (0,3); 7,387 (0,3); 3,328 (96,4); 2,677 (0,5); 2,672 (0,8); 2,667 (0,6); 2,525 (1,9); 2,512 (40,9); 2,508 (83,6); 2,503 (111,4); 2,498 (80,6); 2,494 (38,4); 2,334 (0,5); 2,330 (0,7); 2,325 (0,5); 0,146 (0,5); 0,008 (4,0); 0,000 (116,0); -0,009 (3,8); -0,150 (0,5) 1 H NMR (399.9 MHz, d 6 -DMSO): δ = 10.424 (13.4); 9,112 (13,1); 9,108 (13,1); 8,790 (10.3); 8,786 (11.0); 8,778 (11.0); 8,774 (10.8); 8,315 (5.8); 8,310 (8.0); 8,305 (5.8); 8.295 (6.2); 8,290 (8.5); 8,286 (5.9); 7,690 (9.5); 7.685 (9.9); 7.665 (9.6); 7,659 (10.3); 7,654 (8.2); 7,633 (16.0); 7,612 (9.9); 7,595 (7.6); 7,594 (7.6); 7,583 (7.4); 7,582 (7.5); 7,576 (7.3); 7,574 (7.2); 7,564 (7.0); 7,562 (7.0); 7,479 (7,4); 7,477 (8,1); 7.474 (7.5); 7,472 (7.1); 7,458 (5,8); 7,455 (6,3); 7,453 (5.9); 7,450 (5.6); 7.401 (0.3); 7,387 (0.3); 3,328 (96.4); 2,677 (0.5); 2,672 (0.8); 2,667 (0.6); 2,525 (1.9); 2,512 (40.9); 2,508 (83.6); 2,503 (111,4); 2,498 (80.6); 2,494 (38.4); 2.334 (0.5); 2,330 (0.7); 2.325 (0.5); 0.146 (0.5); 0.008 (4.0); 0.000 (116.0); -0.009 (3.8); -0.150 (0.5)
Schritt 2: N-(4-Brom-2-fluorphenyl)pyridin-3-carbothioamid (A-IV-1) Step 2: N- (4-Bromo-2-fluorophenyl) pyridine-3-carbothioamide (A-IV-1)
18,3 g (61,8 mmol) N-(4-Brom-2-fluorphenyl)nicotinamid (A-III-1) und 25,0 g (61,8 mmol) 2,4-Bis(4- methoxyphenyl)-l,3,2,4-dithiadiphosphetan-2,4-disulfid (Lawesson's Reagenz) wurden in möglichst wenig Anisol gelöst und für 2 Stunden bei 120 °C gerührt. Anschließend wurde der Ansatz eingeengt und gekühlt. Der kristalline Niederschlag wurde abfiltriert, mit wenig kaltem Anisol gewaschen, filtriert und getrocknet. Da die Hauptmenge Produkt im Filtrat verblieb, wurden sowohl Feststoff als auch Filtrat in Ethylacetat gelöst und nacheinander mit wässriger Natrium-EDTA-Lösung und wässriger NaOH- Lösung gewaschen. Die Waschlösungen wurden noch zweimal mit Ethylacetat extrahiert und die vereinigten organischen Phasen über Magnesiumsulfat getrocknet, filtriert und eingedampft. Man erhielt ein Produktgemisch enthaltend 11,3 g (49,5 % Reinheit, 29,1 % d. Th.) der Titelverbindung (A-IV-1). Gleichzeitig waren bereits 39,9 % der Zielverbindung (I-a-1) enthalten. Das erhaltene Gemisch wurde direkt in Schritt 3 weiter umgesetzt. 18.3 g (61.8 mmol) of N- (4-bromo-2-fluorophenyl) nicotinamide (A-III-1) and 25.0 g (61.8 mmol) of 2,4-bis (4-methoxyphenyl) -l, 3,2,4-dithiadiphosphetane-2,4-disulphide (Lawesson's reagent) were dissolved in as little as possible anisole and stirred for 2 hours at 120 ° C. The mixture was then concentrated and cooled. The crystalline precipitate was filtered off, washed with a little cold anisole, filtered and dried. Since most of the product remained in the filtrate, both solid and filtrate were dissolved in ethyl acetate and washed successively with aqueous sodium EDTA solution and aqueous NaOH solution. The washings were extracted twice more with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and evaporated. A product mixture containing 11.3 g (49.5% purity, 29.1% of theory) of the title compound (A-IV-1) was obtained. At the same time, 39.9% of the target compound (Ia-1) were already included. The resulting mixture was reacted further directly in step 3.
LC-MS: m/z 312 [M+H+] LC-MS: m / z 312 [M + H + ]
Schritt 3: 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1) Step 3: 6-Bromo-2- (pyridin-3-yl) -1,3-benzothiazole (I-a-1)
17,9 g (28,8 mmol; angenommene Reinheit 100 %) N-(4-Brom-2-fluorphenyl)pyridin-3-carbothioamid (A-IV-1) und 17,9 g (129,4 mmol) Kaliumcarbonat wurden mit 150 ml DMF versetzt und zwei Stunden bei 120 °C gerührt. Nach dem Abkühlen wurde der Ansatz filtriert und eingedampft. Der Rückstand wurde in Wasser gelöst und mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und eingedampft. Das erhaltene Rohprodukt wurde chromatographisch mittels MPLC gereinigt (Fließmittelgradient Cyclohexan/Ethylacetat). Man erhielt 7,7 g (100 % Reinheit, 91,94 % d. Th.) der Titelverbindung (I-a-1).  17.9 g (28.8 mmol, 100% pure) of N- (4-bromo-2-fluorophenyl) pyridine-3-carbothioamide (A-IV-1) and 17.9 g (129.4 mmol) of potassium carbonate were added with 150 ml of DMF and stirred at 120 ° C for two hours. After cooling, the batch was filtered and evaporated. The residue was dissolved in water and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and evaporated. The crude product obtained was purified by chromatography using MPLC (solvent gradient cyclohexane / ethyl acetate). This gave 7.7 g (100% purity, 91.94% of theory) of the title compound (I-a-1).
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,279 (11 ,7); 9,274 (12,2); 8,784 (8,3); 8,780 (9,5); 8,772 (9,3); 8,768 (9,6); 8,529 (13,9); 8,524 (14,9); 8,479 (5,0); 8,474 (7,7); 8,470 (5,8); 8,459 (5,7); 8,454 (8,2); 8,450 (6,0); 8,318 (0,4); 8,064 (14,0); 8,042 (16,0); 7,750 (9,5); 7,745 (10,1); 7,728 (8,4); 7,723 (8,9); 7,645 (7,1); 7,633 (7,4); 7,625 (7,4); 7,613 (6,9); 3,329 (124,4); 2,673 (1,6); 2,504 (239,2); 2,500 (195,8); 2,330 (1,6); 1,990 (0,3); 0,146 (1,2); 0,000 (239,6); -0,150 (1,2) 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.279 (11, 7); 9,274 (12,2); 8,784 (8.3); 8,780 (9.5); 8,772 (9.3); 8,768 (9.6); 8,529 (13.9); 8,524 (14.9); 8,479 (5.0); 8,474 (7,7); 8,470 (5,8); 8,459 (5,7); 8,454 (8,2); 8,450 (6.0); 8.318 (0.4); 8.064 (14.0); 8,042 (16.0); 7,750 (9.5); 7,745 (10.1); 7,728 (8.4); 7,723 (8.9); 7,645 (7.1); 7.633 (7.4); 7.625 (7.4); 7.613 (6.9); 3,329 (124.4); 2,673 (1.6); 2,504 (239.2); 2,500 (195,8); 2,330 (1.6); 1,990 (0.3); 0.146 (1.2); 0,000 (239.6); -0.150 (1.2)
6-Iod-2-(pyridin-3-yl)- 1 ,3-benzothiazol (I-a-2) 6-iodo-2- (pyridin-3-yl) -1,3-benzothiazole (I-a-2)
Schritt 1: N-(2-Fluor-4-iodphenyl)nicotinamid (A-III-2) Step 1: N- (2-Fluoro-4-iodophenyl) nicotinamide (A-III-2)
Zu einer gerührten Lösung von 2-Fluor-4-iod-anilin (50 g, 210,9 mmol) in 500 ml Dichlormethan wurden 34 ml Pyridin (421,9 mmol) gegeben. Anschließend wurden bei 0 °C tropfenweise 51 g (421,9 mmol) Nicotino ylchlorid zugesetzt und der Ansatz noch 16 Stunden bei Raumtemperatur gerührt. Die Reaktionsmischung wurde dann im Vakuum eingedampft und das Rohprodukt mit Ethylacetat gewaschen, filtriert und unter Vakuum getrocknet. Man erhielt so 40 g (116,9 mmol bei angenommener Reinheit von 100%, 55% d. Th.) der Titelverbindung (A-III-2), die ohne weitere Reinigung in Schritt 2 umgesetzt wurde. To a stirred solution of 2-fluoro-4-iodo-aniline (50 g, 210.9 mmol) in 500 mL dichloromethane was added 34 mL pyridine (421.9 mmol). 51 g (421.9 mmol) of nicotinoyl chloride were then added dropwise at 0 ° C. and the mixture was stirred at room temperature for a further 16 hours. The reaction mixture was then evaporated in vacuo and the crude product washed with ethyl acetate, filtered and dried under vacuum. This gave 40 g (116.9 mmol with assumed purity of 100%, 55% of theory) of the title compound (A-III-2), which was reacted in step 2 without further purification.
Schritt 2: N-(2-Fluor-4-iodphenyl)pyridin-3-carbothioamid (A-IV-2) Step 2: N- (2-Fluoro-4-iodophenyl) pyridine-3-carbothioamide (A-IV-2)
Zu einer gerührten Lösung von 40 g (116,9 mmol, angenommene Reinheit 100%) N-(2-Fluor- 4-iodphenyl)nicotinamid (A-III-2) in 400 ml Toluol wurden 31,1 g (140,3 mmol) Phosphorpentasulphid zugegeben und die Reaktionsmischung für 16 Stunden unter Rückfluss erhitzt. Nach vollständiger Umsetzung des Ausgangsmaterials wurde das Toluol im Vakuum entfernt und das erhaltene Rohprodukt (40 g, 111,7 mmol bei angenommener Reinheit von 100%), 95,6%o d. Th.) ohne weitere Reinigung in Schritt 3 weiter umgesetzt. To a stirred solution of 40 g (116.9 mmol, assumed purity 100%) of N- (2-fluoro-4-iodophenyl) nicotinamide (A-III-2) in 400 ml of toluene was added 31.1 g (140.3 mmol) of phosphorus pentasulphide and the reaction mixture heated at reflux for 16 hours. After complete conversion of the starting material, the toluene was removed in vacuo and the resulting crude product (40 g, 111.7 mmol assuming purity of 100%), 95.6% o. Th.) Further reacted in step 3 without further purification.
Schritt 3: 6-Iod-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-2) Step 3: 6-iodo-2- (pyridin-3-yl) -1,3-benzothiazole (I-a-2)
Zu einer gerührten Lösung von 40 g (111,7 mmol, angenommene Reinheit 100 %) N-(2-Fluor- 4-iodphenyl)pyridin-3-carbothioamid (A-IV-2) in 400 ml DMF wurden 30,8 g (223,4 mmol) Kaliumcarbonat gegeben und die Reaktionsmischung noch 3 Stunden auf 120 °C erhitzt. Nach Beendigung der Reaktion wurde der Ansatz auf Eiswasser gegossen, der sich abscheidende Feststoff ab filtriert, mit Wasser gewaschen und im Vakuum getrocknet. Man erhielt 20 g (100% Reinheit, 53%> d. Th.) der Titelverbindung (I-a-2). 1H-NMR(400,0 MHz, de-DMSO): 5 = 9,271(8,0); 9,267(8,2); 8,777(6,0); 8,774(6,4); 8,765(6,4); 8,762(6,3); 8,657(10,6); 8,654(10,4); 8,470(3,5); 8,466(4,8); 8,460(3,5); 8,450(3,8); 8,445(5,0); 8,440(3,6); 7,915(3,5); 7,894(16,0); 7,884(11,4); 7,880(10,7); 7,863(2,4); 7,859(2,6); 7,639(4,4); 7,637(4,3); 7,627(4,4); 7,625(4,3); 7,619(4,4); 7,607(4,2); 7,605(4,0); 3,329(37,2); 2,893(0,3); 2,678(0,5); 2,673(0,6); 2,669(0,5); 2,527(1,4); 2,509(74,3); 2,504(98,2); 2,500(71,8); 2,335(0,5); 2,331(0,7); 2,327(0,5); 0,008(0,9); 0,000(26,8); - 0,008(1,1) To a stirred solution of 40 g (111.7 mmol, assumed purity 100%) of N- (2-fluoro-4-iodophenyl) pyridine-3-carbothioamide (A-IV-2) in 400 ml of DMF was added 30.8 g (223.4 mmol) of potassium carbonate and the reaction mixture heated to 120 ° C for 3 hours. After completion of the reaction, the batch was poured into ice-water, the precipitated solid filtered off, washed with water and dried in vacuo. 20 g (100% pure, 53% of theory) of the title compound (Ia-2) were obtained. 1 H NMR (400.0 MHz, de-DMSO): 5 = 9.271 (8.0); 9,267 (8.2); 8.777 (6.0); 8,774 (6.4); 8,765 (6.4); 8.762 (6.3); 8.657 (10.6); 8,654 (10.4); 8,470 (3.5); 8,466 (4.8); 8,460 (3.5); 8,450 (3.8); 8,445 (5.0); 8,440 (3.6); 7.915 (3.5); 7,894 (16.0); 7,884 (11.4); 7,880 (10.7); 7,863 (2.4); 7,859 (2.6); 7.639 (4.4); 7,637 (4.3); 7.627 (4.4); 7,625 (4.3); 7,619 (4.4); 7,607 (4.2); 7,605 (4.0); 3,329 (37.2); 2,893 (0.3); 2,678 (0.5); 2,673 (0.6); 2,669 (0.5); 2,527 (1.4); 2,509 (74.3); 2,504 (98.2); 2,500 (71.8); 2,335 (0.5); 2.331 (0.7); 2,327 (0.5); 0.008 (0.9); 0,000 (26.8); - 0.008 (1.1)
Synthese von Verbindungen der Formel (I) nach Methode B und I Synthesis of compounds of the formula (I) according to Method B and I
6-(3-Methylphenyl)-2-(pyridin-3-yl)-l,3-benzothiazol (3) 6- (3-methylphenyl) -2- (pyridin-3-yl) -1,3-benzothiazole (3)
Unter Argon wurden 100 mg (0,34 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 51,4 mg (0,37 mmol) (3-Methylphenyl)borsäure, 11,9 mg (0,01 mmol) Tetrakis(triphenylphosphin)palladium(0) und 72,8 mg (0,68 mmol) Natriumcarbonat in ein Mikrowellen-Reaktionsgefäß eingewogen und mit 1,1 ml einer 1 : 1 -Mischung von entgastem Dioxan und Wasser versetzt. Das Gefäß wurde erneut mit Argon geflutet, verschlossen und für 30 Minuten bei 130 °C in einer Biotage Initiator Mikrowelle erhitzt. Der abgekühlte Ansatz wurde mit Wasser verdünnt und mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über eine Kieselgel-Kartusche filtriert, mit Dichlormethan gewaschen und das Filtrat im Vakuum eingeengt. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittelgradient Cyclohexan/Ethylacetat). Man erhielt 24,5 mg (100 % Reinheit, 23,6 % d. Th.) der Titelverbindung (3).  Under argon, 100 mg (0.34 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 51.4 mg (0.37 mmol) (3-methylphenyl ) boric acid, 11.9 mg (0.01 mmol) of tetrakis (triphenylphosphine) palladium (0) and 72.8 mg (0.68 mmol) of sodium carbonate were weighed into a microwave reaction vessel and treated with 1.1 ml of a 1: 1. Mixture of degassed dioxane and water added. The vessel was again flooded with argon, sealed and heated for 30 minutes at 130 ° C in a Biotage initiator microwave. The cooled mixture was diluted with water and extracted several times with dichloromethane. The combined organic phases were filtered through a silica gel cartridge, washed with dichloromethane and the filtrate was concentrated in vacuo. The purification was carried out by chromatography using MPLC (mobile phase gradient cyclohexane / ethyl acetate). 24.5 mg (100% purity, 23.6% of theory) of the title compound (3) were obtained.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,302 (2,8); 9,297 (2,9); 8,779 (2,0); 8,775 (2,3); 8,767 (2,2); 8,763 (2,3); 8,521 (3,7); 8,517 (4,0); 8,498 (1,2); 8,494 (1,7); 8,489 (1,3); 8,478 (1,3); 8,473 (1,8); 8,469 (1,3); 8,183 (3,3); 8,161 (3,8); 7,894 (2,3); 7,889 (2,4); 7,872 (2,0); 7,868 (2,1); 7,652 (1,6); 7,640 (1,7); 7,631 (2,4); 7,622 (4,1); 7,594 (1,6); 7,575 (1,9); 7,422 (1,7); 7,403 (3,2); 7,384 (1,7); 7,243 (2,0); 7,224 (1,6); 3,332 (108,8); 2,677 (0,5); 2,672 (0,6); 2,668 (0,5); 2,525 (1,6); 2,508 (71,1); 2,503 (95,3); 2,499 (72,6); 2,413 (16,0); 2,334 (0,4); 2,330 (0,6); 2,325 (0,5); 0,008 (1,7); 0,000 (53,6); -0,008 (2,5) 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.302 (2.8); 9,297 (2.9); 8,779 (2.0); 8.775 (2.3); 8,767 (2,2); 8.763 (2.3); 8,521 (3.7); 8,517 (4.0); 8.498 (1.2); 8.494 (1.7); 8.489 (1.3); 8.478 (1.3); 8.473 (1.8); 8.469 (1.3); 8,183 (3,3); 8,161 (3,8); 7.894 (2.3); 7,889 (2,4); 7,872 (2.0); 7,868 (2,1); 7.652 (1.6); 7.640 (1.7); 7.631 (2.4); 7,622 (4,1); 7,594 (1.6); 7,575 (1.9); 7.422 (1.7); 7,403 (3,2); 7,384 (1.7); 7.243 (2.0); 7.224 (1.6); 3,332 (108.8); 2,677 (0.5); 2,672 (0.6); 2,668 (0.5); 2,525 (1.6); 2,508 (71.1); 2,503 (95.3); 2,499 (72.6); 2,413 (16.0); 2.334 (0.4); 2,330 (0.6); 2.325 (0.5); 0.008 (1.7); 0,000 (53.6); -0.008 (2.5)
6-(3-Methylphenyl)-2-(pyridin-3-yl)-l,3-benzothiazol (7) l 6- (3-methylphenyl) -2- (pyridin-3-yl) -1,3-benzothiazole (7) l
Unter Argon wurden 100 mg (0,34 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 59,1 mg (0,37 mmol) (3-Chlorphenyl)borsäure, 11,9 mg (0,01 mmol) Tetrakis(triphenylphosphin)palladium(0) und 72,8 mg (0,68 mmol) Natriumcarbonat in ein Mikrowellen-Reaktionsgefäß eingewogen und mit 1,1 ml einer 1 : 1 -Mischung von entgastem Dioxan und Wasser versetzt. Das Gefäß wurde erneut mit Argon geflutet, verschlossen und für 30 Minuten bei 130 °C in einer Biotage Initiator Mikrowelle erhitzt. Der abgekühlte Ansatz wurde mit Wasser verdünnt und mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über eine Kieselgel-Kartusche filtriert, mit Dichlormethan nachgewaschen und das Filtrat im Vakuum eingeengt. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittelgradient Cyclohexan/Ethylacetat). Man erhielt 99,0 mg (85,7 % Reinheit, 76,5 % d. Th.) der Titelverbindung (7). Under argon, 100 mg (0.34 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 59.1 mg (0.37 mmol) of (3-chlorophenyl ) boric acid, 11.9 mg (0.01 mmol) of tetrakis (triphenylphosphine) palladium (0) and 72.8 mg (0.68 mmol) of sodium carbonate were weighed into a microwave reaction vessel and treated with 1.1 ml of a 1: 1. Mixture of degassed dioxane and water added. The vessel was again flooded with argon, sealed and heated for 30 minutes at 130 ° C in a Biotage initiator microwave. The cooled mixture was diluted with water and extracted several times with dichloromethane. The combined organic phases were filtered through a silica gel cartridge, washed with dichloromethane and the filtrate concentrated in vacuo. The purification was carried out by chromatography using MPLC (mobile phase gradient cyclohexane / ethyl acetate). 99.0 mg (85.7% purity, 76.5% of theory) of the title compound (7) were obtained.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,311 (11 ,4); 9,306 (12,2); 8,785 (8,5); 8,781 (9,1); 8,773 (9,2); 8,769 (9,1); 8,604 (15,0); 8,600 (16,0); 8,507 (4,9); 8,503 (7,4); 8,498 (4,9); 8,487 (5,4); 8,483 (7,7); 8,478 (5,1); 8,319 (0,5); 8,201 (13,4); 8,179 (15,8); 7,942 (9,5); 7,938 (9,4); 7,921 (8,1); 7,916 (8,1); 7,880 (8,6); 7,876 (15,6); 7,872 (9,8); 7,791 (7,6); 7,772 (8,7); 7,656 (7,2); 7,645 (8,1); 7,636 (7,6); 7,625 (8,6); 7,617 (2,0); 7,599 (1,9); 7,570 (7,4); 7,551 (15,6); 7,531 (9,8); 7,492 (9,1); 7,490 (8,6); 7,474 (4,4); 7,472 (4,9); 7,470 (5,0); 5,759 (7,6); 3,333 (249,3); 2,677 (1,3); 2,673 (1,8); 2,669 (1,3); 2,526 (4,8); 2,508 (202,5); 2,504 (262,6); 2,500 (195,5); 2,335 (1,3); 2,331 (1,7); 2,327 (1,3); 1,228 (0,5); 0,146 (0,4); 0,008 (3,1); 0,000 (87,7); -0,008 (3,6); -0,149 (0,4) 6-{2,4-Dimethyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl}-2-(pyridin-3-yl)-l,3-benzothiazol (9) 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.311 (11, 4); 9,306 (12.2); 8,785 (8.5); 8,781 (9.1); 8,773 (9,2); 8,769 (9.1); 8,604 (15.0); 8,600 (16.0); 8.507 (4.9); 8.503 (7.4); 8,498 (4.9); 8,487 (5.4); 8,483 (7,7); 8,478 (5.1); 8.319 (0.5); 8,201 (13.4); 8,179 (15,8); 7.942 (9.5); 7.938 (9.4); 7,921 (8,1); 7,916 (8,1); 7,880 (8.6); 7.876 (15.6); 7,872 (9.8); 7,791 (7.6); 7,772 (8.7); 7,656 (7.2); 7,645 (8.1); 7.636 (7.6); 7.625 (8.6); 7.617 (2.0); 7,599 (1.9); 7,570 (7.4); 7,551 (15.6); 7,531 (9.8); 7,492 (9.1); 7,490 (8,6); 7,474 (4,4); 7,472 (4.9); 7,470 (5.0); 5,759 (7.6); 3,333 (249.3); 2,677 (1.3); 2,673 (1.8); 2,669 (1.3); 2,526 (4,8); 2,508 (202.5); 2,504 (262.6); 2,500 (195.5); 2.335 (1.3); 2.331 (1.7); 2,327 (1,3); 1,228 (0.5); 0.146 (0.4); 0.008 (3.1); 0.000 (87.7); -0.008 (3.6); -0.149 (0.4) 6- {2,4-dimethyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} -2- (pyridin-3-yl) -l, 3-benzothiazole (9 )
Unter Argon wurden 100 mg (0,34 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 130,8 mg (0,37 mmol) {2,4-Dimethyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}borsäure, 11,9 mg (0,01 mmol) Tetrakis(triphenylphosphin)palladium(0) und 72,8 mg (0,68 mmol) Natriumcarbonat in ein Mikrowellen-Reaktionsgefäß eingewogen und mit 4,8 ml einer 5:1 -Mischung von entgastem Dioxan und Wasser versetzt. Das Gefäß wurde verschlossen und für 30 Minuten bei 130 °C in einer Biotage Initiator Mikrowelle erhitzt. Der abgekühlte Ansatz wurde im Vakuum eingeengt, mit Dichlormethan versetzt und mit wenig Wasser gewaschen. Die organische Phase wurde getrocknet, filtriert und eingeengt. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 88,0 mg (95,0% Reinheit, 56,5% d. Th.) der Titelverbindung (9). Under argon, 100 mg (0.34 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 130.8 mg (0.37 mmol) of {2.4 Dimethyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} boric acid, 11.9 mg (0.01 mmol) of tetrakis (triphenylphosphine) palladium (0) and 72.8 mg (0.68 mmol) Sodium carbonate in one Weighed out the microwave reaction vessel and mixed with 4.8 ml of a 5: 1 mixture of degassed dioxane and water. The vessel was sealed and heated for 30 minutes at 130 ° C in a Biotage initiator microwave. The cooled mixture was concentrated in vacuo, treated with dichloromethane and washed with a little water. The organic phase was dried, filtered and concentrated. The purification was carried out by chromatography using MPLC (solvent gradient water / acetonitrile). 88.0 mg (95.0% purity, 56.5% of theory) of the title compound (9) were obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 9,304 (2,2); 8,782 (1,6); 8,773 (1,6); 8,503 (1,2); 8,499 (1,7); 8,494 (1,3); 8,483 (1,3); 8,478 (1,7); 8,474 (1,3); 8,213 (3,8); 8,209 (3,9); 8,176 (3,4); 8,155 (3,7); 8,137 (1,0); 7,659 (1,5); 7,646 (1,5); 7,639 (1,5); 7,627 (1,4); 7,571 (2,4); 7,567 (2,4); 7,550 (2,3); 7,546 (2,3); 7,468 (5,7); 7,261 (4,7); 3,992 (1,2); 3,966 (3,8); 3,940 (3,9); 3,914 (1,3); 3,331 (36,9); 2,677 (0,4); 2,672 (0,6); 2,668 (0,5); 2,526 (1,4); 2,512 (32,8); 2,508 (67,8); 2,503 (90,2); 2,499 (67,5); 2,495 (34,6); 2,413 (14,5); 2,334 (0,5); 2,330 (0,6); 2,326 (0,5); 2,252 (16,0); 1,232 (0,4); 0,146 (0,5); 0,008 (4,0); 0,000 (111,4); -0,009 (5,1); -0,150 (0,5) 1 H NMR (400.0 MHz, de-DMSO): δ = 9.304 (2.2); 8,782 (1.6); 8,773 (1.6); 8,503 (1,2); 8,499 (1.7); 8.494 (1.3); 8.483 (1.3); 8.478 (1.7); 8.474 (1.3); 8.213 (3.8); 8,209 (3,9); 8,176 (3,4); 8,155 (3.7); 8.137 (1.0); 7.659 (1.5); 7.646 (1.5); 7.639 (1.5); 7.627 (1.4); 7,571 (2,4); 7,567 (2,4); 7,550 (2.3); 7,546 (2,3); 7,468 (5.7); 7,261 (4,7); 3,992 (1.2); 3,966 (3.8); 3,940 (3.9); 3.914 (1.3); 3,331 (36.9); 2,677 (0.4); 2,672 (0.6); 2,668 (0.5); 2,526 (1.4); 2,512 (32,8); 2,508 (67.8); 2,503 (90.2); 2,499 (67.5); 2,495 (34.6); 2,413 (14.5); 2.334 (0.5); 2,330 (0.6); 2,326 (0.5); 2.252 (16.0); 1,232 (0.4); 0.146 (0.5); 0.008 (4.0); 0.000 (111.4); -0.009 (5.1); -0.150 (0.5)
6-{2,4-Dimethyl-5-[(2,2,2-trifluorethyl)sulfmyl]phenyl}-2-(pyridin-3-yl)-l,3-benzothiazol (10) 6- {2,4-Dimethyl-5 - [(2,2,2-trifluoroethyl) sulfmyl] -phenyl} -2- (pyridin-3-yl) -l, 3-benzothiazole (10)
88,0 mg (0,20 mmol) 6- {2,4-Dimethyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl} -2-(pyridin-3-yl)-l,3- benzothiazol (9) wurden in 2 ml Dichlormethan vorgelegt und bei 0 °C mit 47,0 mg (0,21 mmol) meta- Chlorperbenzoesäure versetzt. Der Ansatz wurde bis zum vollständigen Umsatz des Edukts (DC- Kontrolle) bei Raumtemperatur gerührt. Anschließend wurde mit gesättigter wässriger Natriumcarbonatlösung versetzt und die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden getrocknet, filtriert und eingeengt. Durch Verrühren des Rückstands mit Acetonitril konnten 46,0 mg (100 %> Reinheit, 50,4 % d. Th.) der Titelverbindung (10) erhalten werden. 88.0 mg (0.20 mmol) of 6- {2,4-dimethyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} -2- (pyridin-3-yl) -l, 3 benzothiazole (9) were introduced into 2 ml of dichloromethane and treated at 0 ° C with 47.0 mg (0.21 mmol) of meta-chloroperbenzoic acid. The batch was stirred until complete conversion of the starting material (TLC check) at room temperature. Subsequently, it was mixed with saturated aqueous sodium carbonate solution and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried, filtered and concentrated. By stirring the residue with acetonitrile, 46.0 mg (100%> purity, 50.4% of theory) of the title compound (10) was obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 9,315 (3,1); 9,310 (3,1); 8,788 (2,3); 8,784 (2,5); 8,776 (2,4); 8,772 (2,6); 8,511 (1,3); 8,506 (1,8); 8,501 (1,4); 8,491 (1,4); 8,485 (1,9); 8,481 (1,4); 8,319 (0,5); 8,289 (4,1); 8,285 (4,1); 8,213 (3,5); 8,192 (3,8); 7,773 (6,6); 7,660 (1,7); 7,648 (1,7); 7,638 (3,1); 7,633 (2,7); 7,630 (2,1); 7,617 (2,3); 7,612 (2,3); 7,357 (4,7); 4,175 (0,8); 4,148 (2,4); 4,118 (2,4); 4,090 (0,9); 3,334 (14,9); 2,677 (0,5); 2,672 (0,6); 2,668 (0,5); 2,525 (1,9); 2,512 (38,3); 2,508 (76,3); 2,503 (100,2); 2,499 (75,0); 2,413 (15,1); 2,356 (16,0); 2,340 (0,6); 2,334 (0,7); 2,330 (0,8); 2,325 (0,6); 2,252 (0,5); 0,008 (2,5); 0,000 (63,7); -0,008 (3,2) 1 H NMR (400.0 MHz, de-DMSO): δ = 9.315 (3.1); 9,310 (3,1); 8.788 (2.3); 8.784 (2.5); 8.776 (2.4); 8.772 (2.6); 8,511 (1,3); 8.506 (1.8); 8,501 (1.4); 8.491 (1.4); 8.485 (1.9); 8.481 (1.4); 8.319 (0.5); 8,289 (4,1); 8,285 (4,1); 8.213 (3.5); 8,192 (3,8); 7,773 (6.6); 7.606 (1.7); 7.648 (1.7); 7,638 (3,1); 7.633 (2.7); 7.630 (2.1); 7.617 (2.3); 7.612 (2.3); 7,357 (4,7); 4.175 (0.8); 4.148 (2.4); 4.118 (2.4); 4,090 (0.9); 3,334 (14.9); 2,677 (0.5); 2,672 (0.6); 2,668 (0.5); 2,525 (1.9); 2,512 (38.3); 2,508 (76.3); 2,503 (100,2); 2,499 (75.0); 2,413 (15,1); 2.356 (16.0); 2,340 (0.6); 2.334 (0.7); 2,330 (0.8); 2.325 (0.6); 2.252 (0.5); 0.008 (2.5); 0.000 (63.7); -0.008 (3,2)
6-{2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl}-2-(pyridin-3-yl)-l,3-benzothiazol (11) 6- {2-Fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} -2- (pyridin-3-yl) -1,3-benzothiazole (11)
Unter Argon wurden 200,0 mg (0,51 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 203,0 mg (0,75 mmol) {2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl}borsäure, 24,0 mg (0,02 mmol) Tetrakis(triphenylphosphin)palladium(0) und 146,0 mg (1,37 mmol) Natriumcarbonat in ein Mikrowellen-Reaktionsgefäß eingewogen und mit 4,8 ml einer 5:1 -Mischung von entgastem Dioxan und Wasser versetzt. Das Gefäß wurde verschlossen und für 30 Minuten bei 130 °C in einer Biotage Initiator Mikrowelle erhitzt. Der abgekühlte Ansatz wurde mit Wasser verdünnt und mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über eine Kieselgel-Kartusche filtriert, mit Dichlormethan nachgewaschen und das Filtrat im Vakuum eingeengt. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 52 mg (95,0% Reinheit, 16,6% d. Th.) der Titelverbindung (11). 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,320 (1,2); 8,787 (1,2); 8,507 (1,7); 8,487 (1,8); 8,440 (4,0); 8,218 (3,5); 8,197 (3,9); 7,820 (3,0); 7,800 (3,0); 7,784 (2,2); 7,763 (2,1); 7,662 (1,3); 7,650 (1,4); 7,643 (1,5); 7,631 (1,4); 7,374 (2,7); 7,344 (2,6); 4,077 (1,3); 4,051 (4,0); 4,025 (4,1); 3,999 (1,4); 3,338 (12,1); 2,678 (0,4); 2,674 (0,5); 2,669 (0,4); 2,509 (57,7); 2,504 (74,0); 2,500 (55,5); 2,460 (16,0); 2,331 (0,5); 0,008 (1,5); 0,000 (35,8) 6-{2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}-2-(pyridin-3-yl)-l,3-benzothiazol (12) Under argon, 200.0 mg (0.51 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 203.0 mg (0.75 mmol) of {2 -Fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} boric acid, 24.0 mg (0.02 mmol) of tetrakis (triphenylphosphine) palladium (0) and 146.0 mg (1 , 37 mmol) sodium carbonate weighed into a microwave reaction vessel and mixed with 4.8 ml of a 5: 1 mixture of degassed dioxane and water. The vessel was sealed and heated for 30 minutes at 130 ° C in a Biotage initiator microwave. The cooled mixture was diluted with water and extracted several times with dichloromethane. The combined organic phases were filtered through a silica gel cartridge, washed with dichloromethane and the filtrate concentrated in vacuo. The purification was carried out by chromatography using MPLC (solvent gradient water / acetonitrile). 52 mg (95.0% purity, 16.6% of theory) of the title compound (11) were obtained. 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.320 (1.2); 8,787 (1.2); 8.507 (1.7); 8.487 (1.8); 8.440 (4.0); 8.218 (3.5); 8,197 (3.9); 7,820 (3.0); 7,800 (3.0); 7.784 (2.2); 7,763 (2,1); 7.662 (1.3); 7,650 (1.4); 7.643 (1.5); 7,631 (1.4); 7,374 (2.7); 7,344 (2.6); 4,077 (1.3); 4,051 (4.0); 4.025 (4.1); 3,999 (1.4); 3,338 (12.1); 2,678 (0.4); 2,674 (0.5); 2,669 (0.4); 2,509 (57.7); 2,504 (74.0); 2,500 (55.5); 2,460 (16.0); 2.331 (0.5); 0.008 (1.5); 0.000 (35.8) 6- {2-Fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -2- (pyridin-3-yl) -l, 3-benzothiazole ( 12)
52,0 mg (0,11 mmol) 6- {2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl} -2-(pyridin-3-yl)-l,3- benzothiazol (11) wurden in 2 ml Dichlormethan vorgelegt und bei 0 °C mit 26,0 mg (0,12 mmol) meta- Chlorperbenzoesäure versetzt. Der Ansatz wurde bis zum vollständigen Umsatz des Edukts (DC- Kontrolle) bei Raumtemperatur gerührt. Anschließend wurde mit gesättigter wässriger Natriumcarbonatlösung versetzt und die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden getrocknet, filtriert und eingeengt. Durch Verrühren des Rückstands mit Acetonitril konnten 26,0 mg (100 % Reinheit, 50,8% d. Th.) der Titelverbindung (12) erhalten werden. 52.0 mg (0.11 mmol) of 6- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} -2- (pyridin-3-yl) -1, 3-benzothiazole (11) were initially charged in 2 ml of dichloromethane and treated at 0 ° C with 26.0 mg (0.12 mmol) of meta-chloroperbenzoic acid. The batch was stirred until complete conversion of the starting material (TLC check) at room temperature. Subsequently, it was mixed with saturated aqueous sodium carbonate solution and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried, filtered and concentrated. By stirring the residue with acetonitrile, 26.0 mg (100% purity, 50.8% of theory) of the title compound (12) was obtained.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,323 (2,8); 9,322 (3,0); 9,318 (3,0); 9,316 (2,9); 8,793 (2,4); 8, 789 (2,5); 8,781 (2,5); 8,777 (2,6); 8,521 (3,9); 8,519 (4,0); 8,515 (2,3); 8,509 (1,4); 8,499 (1,5); 8,494 ( 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.323 (2.8); 9,322 (3.0); 9,318 (3.0); 9.316 (2.9); 8.793 (2.4); 8, 789 (2.5); 8,781 (2.5); 8.777 (2.6); 8,521 (3.9); 8,519 (4.0); 8.515 (2.3); 8.509 (1.4); 8,499 (1.5); 8.494 (
1,8); 8,493 (1,8); 8,489 (1,4); 8,318 (0,4); 8,259 (3,4); 8,238 (3,8); 8,097 (3,1); 8,077 (3,1); 7,851 (1,2);1.8); 8.493 (1.8); 8.489 (1.4); 8.318 (0.4); 8,259 (3,4); 8.238 (3.8); 8,097 (3.1); 8.077 (3.1); 7.851 (1.2);
7,847 (2,1); 7,843 (1,2); 7,830 (1,1); 7,826 (1,9); 7,822 (1,1); 7,664 (1,7); 7,662 (1,7); 7,652 (1,6); 7,6507,847 (2.1); 7,843 (1.2); 7.830 (1.1); 7,826 (1.9); 7.822 (1.1); 7.664 (1.7); 7.662 (1.7); 7.652 (1.6); 7,650
(1,6); 7,644 (1,6); 7,642 (1,6); 7,632 (1,6); 7,630 (1,6); 7,485 (2,4); 7,456 (2,3); 5,758 (16,0); 4,273 (0,6(1.6); 7.644 (1.6); 7.642 (1.6); 7.632 (1.6); 7,630 (1.6); 7.485 (2.4); 7.456 (2.3); 5,758 (16.0); 4,273 (0.6
); 4,267 (0,5); 4,255 (0,4); 4,246 (1,8); 4,239 (1,7); 4,219 (1,8); 4,211 (1,9); 4,202 (0,4); 4,192 (0,6); 4,1 84 (0,7); 3,330 (79,8); 2,676 (0,7); 2,672 (0,9); 2,668 (0,7); 2,525 (2,3); 2,521 (3,5); 2,512 (51,9); 2,507); 4,267 (0.5); 4.255 (0.4); 4.246 (1.8); 4,239 (1.7); 4,219 (1.8); 4,211 (1.9); 4,202 (0.4); 4.192 (0.6); 4.1 84 (0.7); 3,330 (79.8); 2,676 (0.7); 2,672 (0.9); 2,668 (0.7); 2.525 (2.3); 2,521 (3.5); 2,512 (51.9); 2,507
(107,9); 2,503 (143,1); 2,498 (104,6); 2,494 (51,7); 2,464 (14,8); 2,334 (0,7); 2,330 (0,9); 2,325 (0,7); 0,(107.9); 2,503 (143.1); 2,498 (104.6); 2,494 (51.7); 2,464 (14.8); 2.334 (0.7); 2,330 (0.9); 2.325 (0.7); 0
146 (1,0); 0,008 (7,7); 0,000 (228,8); -0,009 (10,1); -0,150 (1,0) 146 (1.0); 0.008 (7.7); 0.000 (228.8); -0.009 (10.1); -0.150 (1.0)
Synthese von Verbindungen der Formel (I) nach Methode C Synthesis of compounds of the formula (I) by Method C.
2-(Pyridin-3-yl)-N-(2,2,2-trifluorethyl)-l,3-benzothiazol-6-amin (13) 2- (pyridin-3-yl) -N- (2,2,2-trifluoroethyl) -1,3-benzothiazol-6-amine (13)
150 mg (0,52 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 76,5 mg (0,77 mmol) 2,2,2- Trifluor-l-aminoethan, 11,8 mg (0,01 mmol) Tris(dibenzylidenaceton)dipalladium(0), 64,2 mg (0,10 mmol) rac-BINAP, 148,5 mg (1,55 mmol) Natrium-tert-butanolat und 3 ml THF wurden in einem Mikrowellenvial vermischt. Der Ansatz wurde anschließend in einer Biotage Initiator Mikrowelle für 1 Stunde auf 120 °C erhitzt. Anschließend wurde der abgekühlte Ansatz in 10 ml Wasser gegeben und mehrfach mit Dichlormethan extrahiert, filtriert und eingedampft. Die Reinigung des Rückstandes erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 108,0 mg (95,0 % Reinheit, 64,4 % d. Th.) der Titelverbindung (13). 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,172 (12,8); 9,167 (13,0); 8,690 (8,5); 8,687 (9,6); 8,678 (9,1); 8,675 (9,5); 8,352 (4,8); 8,348 (7,8); 8,343 (5,3); 8,332 (5,2); 8,328 (8,3); 8,323 (5,4); 7,846 (15,0); 7,824 (16,0); 7,584 (7,6); 7,572 (7,5); 7,564 (7,4); 7,552 (7,1); 7,421 (13,7); 7,415 (14,5); 7,357 (0,3); 7,342 (0,4); 7,033 (8,2); 7,028 (8,2); 7,011 (7,8); 7,005 (7,9); 6,745 (4,0); 6,728 (8,6); 6,710 (4,1); 5,759 (1,8); 4,097 (2,2); 4,073 (7,1); 4,056 (7,7); 4,049 (8,2); 4,032 (7,2); 4,007 (2,4); 3,332 (97,6); 2,673 (1,2); 2,669 (1,0); 2,508 (144,1); 2,504 (188,9); 2,499 (144,6); 2,330 (1,2); 2,326 (1,0); 0,146 (1,5); 0,007 (11,7); 0,000 (282,0); -0,008 (17,0); -0,150 (1,5) 150 mg (0.52 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 76.5 mg (0.77 mmol) of 2,2,2-trifluoro -l-aminoethane, 11.8 mg (0.01 mmol) of tris (dibenzylideneacetone) dipalladium (0), 64.2 mg (0.10 mmol) of rac-BINAP, 148.5 mg (1.55 mmol) of sodium tert-butoxide and 3 ml of THF were mixed in a microwave vial. The batch was then heated in a Biotage initiator microwave for 1 hour at 120 ° C. The cooled mixture was then added to 10 ml of water and extracted several times with dichloromethane, filtered and evaporated. The residue was purified by chromatography using MPLC (solvent gradient water / acetonitrile). 108.0 mg (95.0% purity, 64.4% of theory) of the title compound (13) were obtained. 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.172 (12.8); 9.167 (13.0); 8,690 (8.5); 8,687 (9.6); 8,678 (9.1); 8,675 (9.5); 8,352 (4,8); 8,348 (7.8); 8,343 (5.3); 8,332 (5.2); 8,328 (8,3); 8,323 (5.4); 7,846 (15.0); 7,824 (16.0); 7,584 (7.6); 7,572 (7.5); 7,564 (7.4); 7,552 (7.1); 7,421 (13,7); 7,415 (14.5); 7.357 (0.3); 7,342 (0.4); 7,033 (8.2); 7.028 (8.2); 7,011 (7.8); 7.005 (7.9); 6,745 (4.0); 6,728 (8.6); 6,710 (4,1); 5,759 (1.8); 4.097 (2.2); 4,073 (7.1); 4.056 (7.7); 4,049 (8.2); 4.032 (7.2); 4,007 (2,4); 3,332 (97.6); 2,673 (1.2); 2,669 (1.0); 2,508 (144.1); 2,504 (188.9); 2,499 (144.6); 2,330 (1.2); 2,326 (1.0); 0.146 (1.5); 0.007 (11.7); 0,000 (282,0); -0.008 (17.0); -0.150 (1.5)
6-(Morpholin-4-yl)-2-(pyridin-3-yl)-l,3-benzothiazol (15) 6- (morpholin-4-yl) -2- (pyridin-3-yl) -1,3-benzothiazole (15)
150 mg (0,52 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 11,8 mg (0,01 mmol) Tris(dibenzylidenaceton)dipalladium(0), 64,2 mg (0,10 mmol) rac-BINAP und 148,5 mg (1,55 mmol) Natrium-tert-butanolat wurden in ein mit Argon geflutetes Schlenk-Gefäß eingewogen. Anschließend wurden 4 ml THF eingespritzt, der Ansatz suspendiert und eine Lösung von 53,9 (0,62 mmol) Morpholin in 3 ml THF zugegeben. Die Mischung wurde unter Argon unter Rückfluss über Nacht erhitzt. Der abgekühlte Ansatz wurde anschließend eingedampft, mit wässriger Natriumcarbonatlösung versetzt und mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit Kochsalzlösung gewaschen, über Natriumsulfat getrocknet, filtriert und eingedampft. Die Reinigung des Rückstandes erfolgte chromatographisch per MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 125,0 mg (100 % Reinheit, 81,6 % d. Th.) der Titelverbindung (15). 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,203 (3,8); 8,711 (2,9); 8,701 (2,9); 8,387 (2,9); 8,382 (4,1); 8,377 (2,9); 8,367 (3,2); 8,362 (4,3); 8,357 (3,0); 7,947 (9,0); 7,924 (9,8); 7,641 (8,3); 7,635 (8,6); 7,600 (3,4); 7,588 (3,5); 7,580 (3,4); 7,568 (3,2); 7,296 (4,8); 7,290 (4,7); 7,273 (4,5); 7,267 (4,5); 3,794 (12,8); 3,782 (16,0); 3,770 (13,9); 3,382 (0,5); 3,348 (226,0); 3,246 (13,5); 3,234 (15,9); 3,222 (12,2); 2,676 (0,4); 2,528 (1,0); 2,515 (23,8); 2,511 (47,4); 2,506 (61,7); 2,502 (45,2); 2,498 (22,6); 2,333 (0,4); 0,000 (9,3); -0,009 (0,4) 150 mg (0.52 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 11.8 mg (0.01 mmol) of tris (dibenzylideneacetone) dipalladium (0 ), 64.2 mg (0.10 mmol) of rac-BINAP and 148.5 mg (1.55 mmol) of sodium tert-butoxide were weighed into an argon-flooded Schlenk flask. Subsequently, 4 ml THF were injected, the batch was suspended and a solution of 53.9 (0.62 mmol) morpholine in 3 ml THF was added. The mixture was heated under argon at reflux overnight. The cooled mixture was then evaporated, treated with aqueous sodium carbonate solution and extracted several times with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography by MPLC (solvent gradient water / acetonitrile). 125.0 mg (100% purity, 81.6% of theory) of the title compound (15) were obtained. 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.203 (3.8); 8,711 (2.9); 8,701 (2.9); 8.387 (2.9); 8,382 (4,1); 8.377 (2.9); 8,367 (3,2); 8,362 (4,3); 8.357 (3.0); 7,947 (9.0); 7,924 (9.8); 7,641 (8.3); 7.635 (8.6); 7,600 (3,4); 7,588 (3.5); 7,580 (3,4); 7,568 (3,2); 7.296 (4.8); 7,290 (4,7); 7,273 (4,5); 7.267 (4.5); 3,794 (12.8); 3,782 (16.0); 3,770 (13.9); 3,382 (0.5); 3,348 (226,0); 3,246 (13.5); 3,234 (15.9); 3,222 (12.2); 2,676 (0.4); 2,528 (1.0); 2,515 (23.8); 2,511 (47.4); 2,506 (61.7); 2,502 (45.2); 2,498 (22.6); 2.333 (0.4); 0.000 (9.3); -0.009 (0.4)
6-(Morpholin-4-yl)-2-(pyridin-3-yl)-l,3-benzothiazol (17) 6- (morpholin-4-yl) -2- (pyridin-3-yl) -1,3-benzothiazole (17)
150 mg (0,52 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 11,8 mg (0,01 mmol) Tris(dibenzylidenaceton)dipalladium(0), 64,2 mg (0,10 mmol) rac-BINAP und 148,5 mg (1,55 mmol) Natrium-tert-butanolat wurden in ein mit Argon geflutetes Schlenk-Gefäß eingewogen. Anschließend wurden 4 ml THF eingespritzt, der Ansatz suspendiert und eine Lösung von 74,9 (0,62 mmol) 1- Phenylethanamin in 3 ml THF zugegeben. Die Mischung wurde unter Argon unter Rückfluss über Nacht erhitzt. Der abgekühlte Ansatz wurde eingedampft, mit wässriger Natriumcarbonatlösung versetzt und mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit Brine gewaschen, über Natriumsulfat getrocknet, filtriert und eingedampft. Die Reinigung des Rückstandes erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 125,0 mg (100 % Reinheit, 81,6 % d. Th.) der Titelverbindung (17). 150 mg (0.52 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 11.8 mg (0.01 mmol) of tris (dibenzylideneacetone) dipalladium (0 ), 64.2 mg (0.10 mmol) of rac-BINAP and 148.5 mg (1.55 mmol) of sodium tert-butoxide were weighed into an argon-flooded Schlenk flask. Subsequently, 4 ml of THF were injected, the batch was suspended, and a solution of 74.9 (0.62 mmol) of 1-phenylethanamine in 3 ml of THF was added. The mixture was heated under argon at reflux overnight. The cooled mixture was evaporated, treated with aqueous sodium carbonate solution and extracted several times with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography using MPLC (solvent gradient water / acetonitrile). 125.0 mg (100% pure, 81.6% of theory) of the title compound (17) were obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 9,106 (6,3); 9,102 (6,4); 8,653 (4,8); 8,649 (5,1); 8,641 (5,1); 8,637 (5,1); 8,283 (2,7); 8,279 (3,8); 8,273 (2,8); 8,263 (2,9); 8,258 (4,0); 8,253 (2,8); 7,742 (7,8); 7,719 (8,3); 7,549 (3,6); 7,548 (3,6); 7,537 (3,6); 7,529 (3,6); 7,528 (3,5); 7,517 (3,4); 7,516 (3,4); 7,432 (7,7); 7,413 (10,7); 7,356 (0,4); 7,330 (6,2); 7,312 (11,0); 7,293 (6,0); 7,211 (3,6); 7,193 (5,3); 7,175 (2,0); 6,974 (7,0); 6,969 (8,1); 6,910 (4,6); 6,905 (4,0); 6,888 (4,3); 6,882 (3,9); 6,762 (4,4); 6,744 (4,4); 5,759 (0,7); 4,625 (0,6); 4,608 (2,3); 4,591 (3,6); 4,574 (2,3); 4,557 (0,6); 3,332 (41,4); 2,677 (0,4); 2,672 (0,6); 2,668 (0,5); 2,526 (1,4); 2,508 (70,0); 2,503 (91,6); 2,499 (68,3); 2,335 (0,5); 2,330 (0,6); 2,326 (0,5); 2,275 (1,1); 2,076 (2,7); 1,474 (16,0); 1,457 (16,0); 1,421 (0,5); 1,404 (0,5); 1,257 (0,4); 1,240 (0,5); 0,008 (0,5); 0,000 (13,5); -0,008 (0,6) 1 H NMR (400.0 MHz, de-DMSO): δ = 9.106 (6.3); 9,102 (6,4); 8,653 (4,8); 8,649 (5.1); 8,641 (5.1); 8,637 (5.1); 8,283 (2.7); 8,279 (3.8); 8,273 (2.8); 8.263 (2.9); 8.258 (4.0); 8,253 (2.8); 7,742 (7.8); 7,719 (8.3); 7,549 (3.6); 7,548 (3.6); 7,537 (3.6); 7,529 (3.6); 7,528 (3.5); 7,517 (3,4); 7,516 (3,4); 7,432 (7,7); 7.413 (10.7); 7.356 (0.4); 7,330 (6.2); 7,312 (11.0); 7,293 (6.0); 7.211 (3.6); 7,193 (5,3); 7.175 (2.0); 6,974 (7.0); 6,969 (8,1); 6.910 (4.6); 6.905 (4.0); 6,888 (4,3); 6,882 (3.9); 6,762 (4.4); 6,744 (4.4); 5,759 (0.7); 4.625 (0.6); 4,608 (2,3); 4,591 (3.6); 4.574 (2.3); 4,557 (0.6); 3,332 (41.4); 2,677 (0.4); 2,672 (0.6); 2,668 (0.5); 2,526 (1.4); 2,508 (70.0); 2,503 (91.6); 2,499 (68.3); 2.335 (0.5); 2,330 (0.6); 2,326 (0.5); 2.275 (1.1); 2.076 (2.7); 1,474 (16.0); 1,457 (16.0); 1,421 (0.5); 1.404 (0.5); 1.257 (0.4); 1.240 (0.5); 0.008 (0.5); 0.000 (13.5); -0.008 (0.6)
Synthese von Verbindungen der Formel (I) nach Methoden D und I Synthesis of compounds of the formula (I) according to Methods D and I
N-{2,4-Dimethyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl}-2-(pyridin-3-yl)-l,3-benzothiazol-6-amin (18) N- {2,4-dimethyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} -2- (pyridin-3-yl) -1,3-benzothiazol-6-amine (18)
250 mg (0,85 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 242,5 mg (1,03 mmol) 2,4- Dimethyl-5-[(2,2,2-trifluorethyl)sulfanyl]anilin, 31,0 mg (0,13 mmol) Palladium(II)acetat, 96,0 mg (0,15 mmol) rac-BINAP, 504,0 mg (1,54 mmol) Cäsiumcarbonat und 5 ml Toluol wurden in einem Mikrowellenvial vermischt. Der Ansatz wurde anschließend in einer Biotage Initiator Mikrowelle für 2,5 Stunden auf 130 °C erhitzt. Anschließend wurde der abgekühlte Ansatz in 10 ml Wasser gegeben und zweimal mit Dichlormethan, einmal mit Ethylacetat extrahiert, filtriert und eingedampft. Die Reinigung des Rückstandes erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 190,0 mg (92,0 % Reinheit, 45,7% d. Th.) der Titelverbindung (18). 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,177 (3,3); 9,172 (3,4); 8,692 (2,5); 8,683 (2,4); 8,680 (2,5); 8,354 (1,9); 8,339 (1,5); 8,334 (2,1); 7,902 (6,9); 7,879 (3,6); 7,586 (1,7); 7,573 (1,8); 7,566 (1,8); 7,554 (1,6); 7,41 1 (5,7); 7,341 (4,0); 7,336 (4,2); 7,181 (5,0); 7,115 (2,0); 7,110 (2,1); 7,093 (2,0); 7,088 (2,0); 4,056 (0,4); 4,038 (1,2); 4,020 (1,2); 4,002 (0,5); 3,880 (1,2); 3,854 (3,8); 3,828 (3,9); 3,802 (1,4); 3,332 (34,3); 2,673 (0,6); 2,504 (94,6); 2,350 (15,3); 2,180 (16,0); 1,990 (5,0); 1,231 (0,5); 1,193 (1,3); 1,176 (2,6); 1,158 (1,3); 0,000 (2,6) 250 mg (0.85 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 242.5 mg (1.03 mmol) of 2,4-dimethyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] aniline, 31.0 mg (0.13 mmol) palladium (II) acetate, 96.0 mg (0.15 mmol) rac-BINAP, 504.0 mg ( 1.54 mmol) of cesium carbonate and 5 ml of toluene were mixed in a microwave vial. The batch was then heated in a Biotage initiator microwave for 2.5 hours at 130 ° C. The cooled mixture was then added to 10 ml of water and extracted twice with dichloromethane, once with ethyl acetate, filtered and evaporated. The residue was purified by chromatography using MPLC (solvent gradient water / acetonitrile). 190.0 mg (92.0% purity, 45.7% of theory) of the title compound (18) were obtained. 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.177 (3.3); 9,172 (3,4); 8,692 (2.5); 8.683 (2.4); 8,680 (2.5); 8,354 (1.9); 8.399 (1.5); 8,334 (2,1); 7.902 (6.9); 7,879 (3.6); 7,586 (1.7); 7,573 (1.8); 7,566 (1.8); 7,554 (1.6); 7.41 1 (5.7); 7,341 (4.0); 7,336 (4,2); 7,181 (5.0); 7.115 (2.0); 7,110 (2,1); 7,093 (2.0); 7.088 (2.0); 4.056 (0.4); 4.038 (1.2); 4,020 (1.2); 4.002 (0.5); 3.880 (1.2); 3,854 (3.8); 3.828 (3.9); 3.802 (1.4); 3,332 (34.3); 2,673 (0.6); 2,504 (94.6); 2,350 (15.3); 2,180 (16.0); 1,990 (5.0); 1.231 (0.5); 1.193 (1.3); 1.176 (2.6); 1.158 (1.3); 0,000 (2,6)
N-{2,4-Dimethyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}-2-(pyridin-3-yl)-l,3-benzothiazol-6-amin (19) N- {2,4-dimethyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -2- (pyridin-3-yl) -1,3-benzothiazol-6-amine (19)
172,0 mg (0,35 mmol) N- {2,4-Dimethyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl} -2-(pyridin-3-yl)-l,3- benzothiazol-6-amin (18) wurden in 1 ml Dichlormethan vorgelegt und bei 0 °C mit 81,0 mg (0,36 mmol) meta-Chlorperbenzoesäure versetzt. Der Ansatz wurde bis zum vollständigen Umsatz des Edukts (ca. 40 min, DC-Kontrolle) bei Raumtem eratur gerührt. Anschließend wurde mit gesättigter wässriger Natriumcarbonatlösung versetzt und die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden getrocknet, filtriert und eingeengt. Durch Verrühren des Rückstands mit Acetonitril konnten 100,0 mg (96 % Reinheit, 58,6 % d. Th.) der Titelverbindung (19) erhalten werden. 172.0 mg (0.35 mmol) of N- {2,4-dimethyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} -2- (pyridin-3-yl) -l, 3 benzothiazole-6-amine (18) were initially charged in 1 ml of dichloromethane and treated at 0 ° C with 81.0 mg (0.36 mmol) of meta-chloroperbenzoic acid. The batch was stirred at room temperature until complete conversion of the starting material (about 40 min, TLC check). Subsequently, it was mixed with saturated aqueous sodium carbonate solution and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried, filtered and concentrated. Trituration of the residue with acetonitrile gave 100.0 mg (96% purity, 58.6% of theory) of the title compound (19).
1H-NMR(400,0 MHz, de-DMSO):□ = 9,193 (3,1); 9,189 (3,2); 8,708 (2,3); 8,704 (2,5); 8,696 (2,5); 8,692 (2,5); 8,380 (1,3); 8,376 (1,8); 8,370 (1,3); 8,360 (1,5); 8,354 (2,0); 8,350 (1,4); 8,318 (1,0); 8,037 (4,3); 7,953 (3,5); 7,931 (3,9); 7,734 (6,2); 7,598 (1,7); 7,586 (1,7); 7,578 (1,7); 7,566 (1,7); 7,565 (1,6); 7,516 (3,8); 7,510 (3,8); 7,238 (4,9); 7,218 (2,2); 7,213 (2,1); 7,196 (2,1); 7, 190 (2,0); 4,108 (0,6); 4,099 (0,5); 4,081 (0,7); 4,071 (1,4); 4,056 (0,6); 4,044 (1,5); 4,030 (1,4); 4,017 (0,7); 4,002 (1,5); 3,993 (0,7); 3,975 (0,6); 3,966 (0,6); 3,331 (36,1); 3,308 (0,5); 2,672 (0,5); 2,508 (59,1); 2,503 (76,1); 2,499 (56,7); 2,350 (0,8); 2,334 (0,5); 2,330 (0,7); 2,325 (0,6); 2,308 (15,7); 2,282 (16,0); 2,180 (0,8); 0,000 (0,9) 1 H NMR (400.0 MHz, de-DMSO): □ = 9.193 (3.1); 9,189 (3,2); 8,708 (2,3); 8,704 (2.5); 8.696 (2.5); 8,692 (2.5); 8,380 (1.3); 8.376 (1.8); 8,370 (1.3); 8.360 (1.5); 8.354 (2.0); 8,350 (1.4); 8.318 (1.0); 8.037 (4.3); 7,953 (3.5); 7,931 (3.9); 7,734 (6.2); 7,598 (1.7); 7,586 (1.7); 7,578 (1.7); 7,566 (1.7); 7,565 (1.6); 7,516 (3.8); 7,510 (3.8); 7.238 (4.9); 7.218 (2.2); 7.213 (2.1); 7,196 (2,1); 7, 190 (2.0); 4.108 (0.6); 4,099 (0.5); 4,081 (0.7); 4,071 (1.4); 4.056 (0.6); 4,044 (1.5); 4,030 (1.4); 4.017 (0.7); 4.002 (1.5); 3,993 (0.7); 3.975 (0.6); 3.966 (0.6); 3,331 (36.1); 3.308 (0.5); 2,672 (0.5); 2,508 (59.1); 2,503 (76.1); 2,499 (56.7); 2,350 (0.8); 2.334 (0.5); 2,330 (0.7); 2.325 (0.6); 2.308 (15.7); 2,282 (16.0); 2,180 (0.8); 0,000 (0.9)
N-{2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl}-2-(pyridin-3-yl)-l,3-benzothiazol-6- amin (20) N- {2-Fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} -2- (pyridin-3-yl) -1,3-benzothiazole-6-amine (20)
250 mg (0,85 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 246,0 mg (1,03 mmol) 2-Fluor- 4-methyl-5-[(2,2,2-trifluorethyl)sulfanyl]anilin, 31,0 mg (0,13 mmol) Palladium(II)-acetat, 96,0 mg (0,15 mmol) rac-BINAP, 504,0 mg (1,54 mmol) Cäsiumcarbonat und 5 ml Toluol wurden in einem Mikrowellenvial vermischt. Der Ansatz wurde anschließend in einer Biotage Initiator Mikrowelle für 3 Stunden auf 130 °C erhitzt. Anschließend wurde der abgekühlte Ansatz in 10 ml Wasser gegeben, zweimal mit Dichlormethan, einmal mit Ethylacetat extrahiert, filtriert und eingedampft. Die Reinigung des Rückstandes erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 37,0 mg (95,0 % Reinheit, 9,1 % d. Th.) der Titelverbindung (20). 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,197 (2,9); 9,193 (2,9); 9,191 (2,8); 8,711 (2,3); 8,707 (2,6); 8,699 (2,5); 8,695 (2,6); 8,382 (1,4); 8,376 (1,8); 8,372 (1,6); 8,362 (5,3); 8,352 (1,7); 7,947 (3,8); 7,925 (4,2); 7,599 (1,7); 7,597 (1,8); 7,587 (1,6); 7,585 (1,7); 7,579 (1,7); 7,577 (1,7); 7,565 (2,2); 7,560 (3,5); 7,557 (3,6); 7,551 (3,3); 7,540 (2,9); 7,274 (2,6); 7,244 (2,7); 7,207 (2,0); 7,201 (1,9); 7,184 (1,9); 7,179 (1,9); 5,759 (2,4); 3,922 (1,2); 3,895 (3,9); 3,869 (4,1); 3,843 (1,4); 3,333 (29,2); 2,673 (0,4); 2,526 (0,9); 2,513 (20,8); 2,508 (43,4); 2,504 (57,9); 2,499 (42,1); 2,495 (20,4); 2,380 (16,0); 2,331 (0,4); 2,304 (0,6); 0,000 (0,4) N-{2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}-2-(pyridin-3-yl)-l,3-benzothiazol-6- amin (21) 250 mg (0.85 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 246.0 mg (1.03 mmol) of 2-fluoro-4-methyl -5 - [(2,2,2-trifluoroethyl) sulfanyl] aniline, 31.0 mg (0.13 mmol) palladium (II) acetate, 96.0 mg (0.15 mmol) rac-BINAP, 504, 0 mg (1.54 mmol) of cesium carbonate and 5 ml of toluene were mixed in a microwave vial. The batch was then heated in a Biotage initiator microwave at 130 ° C for 3 hours. The cooled mixture was then added to 10 ml of water, extracted twice with dichloromethane, once with ethyl acetate, filtered and evaporated. The residue was purified by chromatography using MPLC (solvent gradient water / acetonitrile). 37.0 mg (95.0% purity, 9.1% of theory) of the title compound (20) were obtained. 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.197 (2.9); 9.193 (2.9); 9,191 (2,8); 8.711 (2.3); 8,707 (2.6); 8,699 (2.5); 8.695 (2.6); 8,382 (1.4); 8.376 (1.8); 8.372 (1.6); 8,362 (5.3); 8.352 (1.7); 7,947 (3.8); 7.925 (4.2); 7,599 (1.7); 7,597 (1.8); 7,587 (1.6); 7,585 (1.7); 7,579 (1.7); 7,577 (1.7); 7,565 (2,2); 7,560 (3.5); 7,557 (3.6); 7,551 (3.3); 7,540 (2.9); 7.274 (2.6); 7.244 (2.7); 7,207 (2,0); 7,201 (1.9); 7.184 (1.9); 7.179 (1.9); 5,759 (2,4); 3.922 (1.2); 3,895 (3.9); 3,869 (4,1); 3,843 (1.4); 3,333 (29.2); 2,673 (0.4); 2,526 (0.9); 2,513 (20.8); 2,508 (43.4); 2,504 (57.9); 2,499 (42.1); 2,495 (20.4); 2,380 (16.0); 2,331 (0.4); 2.304 (0.6); 0.000 (0.4) N- {2-Fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -2- (pyridin-3-yl) -l, 3-benzothiazole 6- amine (21)
100,0 mg (0,21 mmol) N- {2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl} -2-(pyridin-3-yl)- l,3-benzothiazol-6-amin (20) wurden in 1 ml Dichlormethan vorgelegt und bei 0 °C mit 48,0 mg (0,21 mmol) meta-Chlorperbenzoesäure versetzt. Der Ansatz wurde bis zum vollständigen Umsatz des Edukts (ca. 40 min, DC-Kontrolle) bei Raumtemperatur gerührt. Anschließend wurde mit gesättigter wässriger Natriumcarbonatlösung versetzt und die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden getrocknet, filtriert und eingeengt. Die Reinigung des Rückstandes erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 55,0 mg (96% Reinheit, 53,8% d. Th.) der Titelverbindung (21). 100.0 mg (0.21 mmol) of N- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} -2- (pyridin-3-yl) -1, 3-benzothiazol-6-amine (20) were initially charged in 1 ml of dichloromethane and admixed at 0 ° C with 48.0 mg (0.21 mmol) of meta-chloroperbenzoic acid. The mixture was stirred until complete conversion of the starting material (about 40 minutes, TLC check) at room temperature. Subsequently, it was mixed with saturated aqueous sodium carbonate solution and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried, filtered and concentrated. The residue was purified by chromatography using MPLC (solvent gradient water / acetonitrile). 55.0 mg (96% purity, 53.8% of theory) of the title compound (21) were obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 9,212 (3,0); 9,208 (3,1); 8,721 (2,0); 8,718 (2,2); 8,709 (2,2); 8,706 (2,2); 8,598 (3,8); 8,400 (1,3); 8,396 (1,8); 8,390 (1,3); 8,380 (1,4); 8,375 (1,9); 8,370 (1,4); 7,998 (3,6); 7,976 (3,9); 7,849 (3,0); 7,829 (3,0); 7,706 (3,3); 7,701 (3,5); 7,608 (1,6); 7,596 (1,6); 7,589 (1,6); 7,577 (1,5); 7,351 (2,5); 7,321 (2,6); 7,307 (2,1); 7,301 (2,0); 7,284 (1,9); 7,279 (1,9); 5,755 (5,4); 4,159 (0,4); 4,149 (0,5); 4,132 (0,8); 4,122 (1,7); 4,107 (1,6); 4,095 (1,8); 4,080 (1,7); 4,069 (0,8); 4,053 (0,6); 4,043 (0,4); 3,338 (104,4); 3,311 (0,4); 2,673 (0,3); 2,509 (44,0); 2,504 (57,4); 2,500 (42,8); 2,334 (16,0); 1,990 (0,7); 1,176 (0,4); 0,008 (2,5); 0,000 (61,8); -0,008 (3,1) 1 H NMR (400.0 MHz, de-DMSO): δ = 9.212 (3.0); 9,208 (3,1); 8,721 (2.0); 8.718 (2.2); 8,709 (2.2); 8.706 (2.2); 8,598 (3.8); 8,400 (1.3); 8.396 (1.8); 8.390 (1.3); 8,380 (1.4); 8.375 (1.9); 8,370 (1.4); 7,998 (3.6); 7.976 (3.9); 7,849 (3.0); 7.829 (3.0); 7,706 (3.3); 7.701 (3.5); 7.608 (1.6); 7,596 (1.6); 7,589 (1.6); 7,577 (1.5); 7.351 (2.5); 7,321 (2,6); 7,307 (2,1); 7,301 (2.0); 7.284 (1.9); 7.279 (1.9); 5,755 (5.4); 4.159 (0.4); 4,149 (0.5); 4,132 (0.8); 4.122 (1.7); 4.107 (1.6); 4,095 (1.8); 4,080 (1.7); 4.069 (0.8); 4,053 (0.6); 4,043 (0.4); 3,338 (104.4); 3,311 (0.4); 2,673 (0.3); 2,509 (44.0); 2,504 (57.4); 2,500 (42.8); 2,334 (16.0); 1,990 (0.7); 1.176 (0.4); 0.008 (2.5); 0,000 (61.8); -0.008 (3,1)
N-(Pyridin-2-yl)-2-(pyridin-3-yl)-l,3-benzothiazol-6-amin (24) N- (pyridin-2-yl) -2- (pyridin-3-yl) -1,3-benzothiazol-6-amine (24)
150 mg (0,52 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 58 mg (0,62 mmol) Aminopyridin, 19,0 mg (0,08 mmol) Palladium(II)acetat, 58,0 mg (0,09 mmol) rac-BINAP, 302,0 mg (0,9 mmol) Cäsiumcarbonat und 5 ml Toluol wurden in einem Mikrowellenvial vermischt. Der Ansatz wurde anschließend in einer Biotage Initiator Mikrowelle für 2 Stunden auf 130 °C erhitzt. Anschließend wurde der abgekühlte Ansatz in 10 ml wässrige Natriumcarbonatlösung gegeben, zweimal mit Dichlormethan, einmal mit Ethylacetat extrahiert, filtriert und eingedampft. Die Reinigung des Rückstandes erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 10,0 mg (95,0 % Reinheit, 6,1 % d. Th.) der Titelverbindung (24). 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,303 (3,6); 9,299 (3,6); 8,785 (2,8); 8,781 (3,0); 8,773 (3,0); 8,769 (3,0); 8,501 (1,6); 8,497 (2,1); 8,491 (1,6); 8,481 (1,8); 8,475 (2,2); 8,471 (1,7); 8,187 (4,9); 8,183 (4,8); 8,160 (4,4); 8,138 (8,4); 7,659 (2,0); 7,657 (2,0); 7,647 (2,0); 7,645 (2,0); 7,639 (2,0); 7,637 (1,9); 7,627 (1,9); 7,625 (1,9); 7,574 (3,2); 7,569 (3,2); 7,553 (3,1); 7,548 (3,1); 7,474 (1,8); 7,457 (3,7); 7,454 (3,6); 7,435 (1,8); 7,430 (1,9); 7,418 (2,1); 7,413 (2,4); 7,398 (1,1); 7,394 (1,2); 7,339 (1,1); 7,335 (1,6); 7,320 (4,0); 7,316 (3,4); 7,307 (2,7); 7,304 (2,6); 7,290 (2,2); 7,287 (2,4); 7,271 (0,8); 7,268 (0,8); 5,759 (1,6); 3,335 (10,3); 2,915 (2,1); 2,897 (6,9); 2,878 (7,0); 2,860 (2,2); 2,673 (0,5); 2,668 (0,3); 2,526 (0,9); 2,513 (26,6); 2,508 (54,0); 2,504 (70,4); 2,499 (51,0); 2,495 (24,9); 2,335 (0,3); 2,330 (0,5); 2,326 (0,3); 2,077 (2,1); 1,185 (7,6); 1,167 (16,0); 1,148 (7,3); 0,008 (2,2); 0,000 (64,3); -0,009 (2,4) 150 mg (0.52 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 58 mg (0.62 mmol) of aminopyridine, 19.0 mg (0, 08 mmol) of palladium (II) acetate, 58.0 mg (0.09 mmol) of rac-BINAP, 302.0 mg (0.9 mmol) of cesium carbonate and 5 ml of toluene were mixed in a microwave vial. The batch was then heated in a Biotage initiator microwave at 130 ° C for 2 hours. The cooled mixture was then added to 10 ml of aqueous sodium carbonate solution, extracted twice with dichloromethane, once with ethyl acetate, filtered and evaporated. The residue was purified by chromatography using MPLC (solvent gradient water / acetonitrile). 10.0 mg (95.0% purity, 6.1% of theory) of the title compound (24) were obtained. 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.303 (3.6); 9,299 (3.6); 8,785 (2.8); 8,781 (3.0); 8,773 (3.0); 8.769 (3.0); 8,501 (1.6); 8.497 (2.1); 8.491 (1.6); 8.481 (1.8); 8.475 (2.2); 8.471 (1.7); 8,187 (4,9); 8,183 (4,8); 8,160 (4.4); 8.138 (8.4); 7.659 (2.0); 7.657 (2.0); 7.647 (2.0); 7.645 (2.0); 7.639 (2.0); 7.637 (1.9); 7,627 (1.9); 7.625 (1.9); 7,574 (3.2); 7,569 (3,2); 7,553 (3,1); 7,548 (3.1); 7.474 (1.8); 7,457 (3,7); 7.454 (3.6); 7.435 (1.8); 7,430 (1.9); 7,418 (2,1); 7.413 (2.4); 7,398 (1,1); 7.394 (1.2); 7.399 (1.1); 7.335 (1.6); 7,320 (4.0); 7,316 (3,4); 7,307 (2.7); 7.304 (2.6); 7.290 (2.2); 7,287 (2,4); 7.271 (0.8); 7.268 (0.8); 5,759 (1.6); 3,335 (10.3); 2,915 (2.1); 2,897 (6.9); 2,878 (7.0); 2,860 (2.2); 2,673 (0.5); 2,668 (0.3); 2,526 (0.9); 2,513 (26.6); 2,508 (54.0); 2,504 (70.4); 2,499 (51.0); 2,495 (24.9); 2.335 (0.3); 2.330 (0.5); 2,326 (0.3); 2,077 (2.1); 1.185 (7.6); 1.167 (16.0); 1,148 (7.3); 0.008 (2.2); 0,000 (64.3); -0.009 (2,4)
Synthese von Verbindungen der Formel (I) nach Methode E Synthesis of compounds of the formula (I) according to method E
6-(lH-Imidazol-l-yl)-2-(pyridin-3-yl)-l,3-benzothiazol (25) 6- (1H-Imidazol-1-yl) -2- (pyridin-3-yl) -1,3-benzothiazole (25)
Unter Argon wurden 500 mg (1 ,7 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 140 mg (2,1 mmol) Imidazol, 26 mg (0,14 mmol) Kupfer(I)iodid, 712 mg (5,2 mmol) Kaliumcarbonat und 50 mg (0,2 mmol) trans-l,2-Bis(2'-pyridylideneamino)cyclohexan (racemisch) [herstellbar gemäß Chem. Eur. J. 2005, 2483] in ein Reaktionsgefäß eingewogen und 19 g DMF zugegeben. Der Ansatz wurde anschließend mit 2 Tropfen Polyethylenglykol versetzt und unter Argon bei 120 °C über Nacht erhitzt. Anschließend wurden 1 g (15 mmol) Imidazol zugesetzt und der Ansatz unter Argon weitere 18 Stunden bei 120 °C gerührt. Der abgekühlte Ansatz wurde im Vakuum eingedampft, der Rückstand mit Wasser versetzt und mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden getrocknet, filtriert und eingedampft. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittel Petrolether/Aceton). Man erhielt 200,0 mg (100 % Reinheit, 41,8 % d. Th.) der Titelverbindung (25). 1H-NMR(601,6 MHz, d6-DMSO): δ = 9,954 (0,4); 9,302 (8,1); 8,784 (5,9); 8,777 (6,2); 8,560 (14,0);Under argon, 500 mg (1.7 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 140 mg (2.1 mmol) of imidazole, 26 mg (0 , 14 mmol) copper (I) iodide, 712 mg (5.2 mmol) potassium carbonate and 50 mg (0.2 mmol) of trans-l, 2-bis (2'-pyridylideneamino) cyclohexane (racemic) [can be prepared according to Chem. Eur. J. 2005, 2483] weighed into a reaction vessel and added 19 g of DMF. The batch was then mixed with 2 drops of polyethylene glycol and heated under argon at 120 ° C overnight. Subsequently, 1 g (15 mmol) of imidazole was added and the mixture stirred under argon at 120 ° C for a further 18 hours. The cooled mixture was evaporated in vacuo, the residue was mixed with water and extracted several times with ethyl acetate. The combined organic phases were dried, filtered and evaporated. The purification was carried out by chromatography using MPLC (eluent petroleum ether / acetone). 200.0 mg (100% purity, 41.8% of theory) of the title compound (25) were obtained. 1 H NMR (601.6 MHz, d 6 -DMSO): δ = 9.954 (0.4); 9,302 (8,1); 8,784 (5.9); 8,777 (6.2); 8,560 (14.0);
8,557 (14,7); 8,492 (4,8); 8,489 (7,5); 8,486 (5,3); 8,479 (5,3); 8,476 (7,8); 8,473 (5,4); 8,404 (2,2);8,557 (14.7); 8,492 (4,8); 8,489 (7.5); 8,486 (5,3); 8,479 (5,3); 8.476 (7.8); 8,473 (5.4); 8.404 (2.2);
8,325 (0,4); 8,243 (14,4); 8,228 (16,0); 7,907 (8,9); 7,904 (9,4); 7,893 (10,1); 7,889 (10,6); 7,843 (0,4);8.325 (0.4); 8,243 (14.4); 8.228 (16.0); 7.907 (8.9); 7.904 (9.4); 7,893 (10.1); 7,889 (10.6); 7,843 (0.4);
7,651 (6,2); 7,643 (6,4); 7,638 (6,4); 7,629 (6,1); 7,202 (2,1); 5,765 (2,0); 3,352 (8,3); 2,894 (0,4); 2,7357.651 (6.2); 7,643 (6.4); 7,638 (6.4); 7,629 (6,1); 7,202 (2,1); 5,765 (2.0); 3,352 (8.3); 2,894 (0.4); 2,735
(0,5); 2,620 (0,5); 2,523 (1,6); 2,511 (70,7); 2,508 (97,6); 2,505 (74,1); 2,391 (0,6); 0,097 (0,5); 0,005 (3,9); 0,000 (102,4); -0,099 (0,5) (0.5); 2,620 (0.5); 2,523 (1.6); 2,511 (70,7); 2,508 (97.6); 2,505 (74.1); 2.391 (0.6); 0.097 (0.5); 0.005 (3.9); 0,000 (102.4); -0.099 (0.5)
2-(Pyridin-3-yl)-6-[3-(trifluormethyl)-lH-pyrazol-l-yl]-l,3-benzothiazol (28) 2- (Pyridin-3-yl) -6- [3- (trifluoromethyl) -1H-pyrazol-1-yl] -1,3-benzothiazole (28)
Unter Argon wurden 300 mg (1,03 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 168 mg (1,2 mmol) 3-Trifluorpyrazol, 16 mg (0,08 mmol) Kupfer(I)iodid, 427 mg (3,1 mmol) Kaliumcarbonat und 30 mg (0,1 mmol) trans-l,2-Bis(2'-pyridylideneamino)cyclohexane (racemisch) [herstellbar gemäß Chem. Eur. J. 2005, 2483] in ein Reaktionsgefäß eingewogen und 9,5 g DMF zugegeben. Der Ansatz wurde anschließend mit 2 Tropfen Polyethylenglykol versetzt und unter Argon über Nacht auf 120 °C erhitzt. Anschließend wurde der Ansatz unter Argon weitere 10 Stunden bei 130 °C gerührt. Der abgekühlte Ansatz wurde im Vakuum eingedampft, der Rückstand mit Wasser versetzt und mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden getrocknet, filtriert und eingedampft. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittel Petrolether/Aceton). Man erhielt 244,0 mg (100 % Reinheit, 68,4 % d. Th.) der Titelverbindung (28). Under argon, 300 mg (1.03 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 168 mg (1.2 mmol) of 3-trifluoropyrrazole, 16 mg (0.08 mmol) of copper (I) iodide, 427 mg (3.1 mmol) of potassium carbonate and 30 mg (0.1 mmol) of trans-l, 2-bis (2'-pyridylideneamino) cyclohexane (racemic) [preparable according to Chem. Eur. J. 2005, 2483] was weighed into a reaction vessel and 9.5 g of DMF were added. The mixture was then mixed with 2 drops of polyethylene glycol and heated under argon overnight at 120 ° C. The mixture was then stirred under argon at 130 ° C for a further 10 hours. The cooled mixture was evaporated in vacuo, the residue was mixed with water and extracted several times with ethyl acetate. The combined organic phases were dried, filtered and evaporated. The purification was carried out by chromatography using MPLC (eluent petroleum ether / acetone). 244.0 mg (100% purity, 68.4% of theory) of the title compound (28) were obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 9,305 (3,2); 8,837 (11,4); 8,777 (16,0); 8,771 (15,8); 8,490 (6,4); 8,470 (6,7); 8,319 (0,4); 8,273 (11,0); 8,251 (14,5); 8,126 (8,6); 8,120 (8,7); 8,103 (6,5); 8,098 (6,6); 7,976 (0,6); 7,656 (4,1); 7,644 (4,6); 7,637 (4,5); 7,625 (3,8); 7,121 (12,0); 7,115 (12,1); 6,709 (0,6); 3,333 (43,9); 2,676 (0,6); 2,511 (70,7); 2,507 (90,6); 2,503 (70,5); 2,334 (0,5); 1,223 (0,7); 1,144 (0,7); 1,100 (0,4); 1,089 (0,9); 1,039 (0,6); 0,866 (0,3); 0,841 (0,4); 0,824 (0,3); 0,146 (0,5); 0,000 (99,6); -0,150 (0,5) 2-(Pyridin-3-yl)-6-[3-(pyrimidin-2-yl)-lH-pyrazol-l-yl]-l,3-benzothiazol (30) 1 H NMR (400.0 MHz, de-DMSO): δ = 9.305 (3.2); 8,837 (11,4); 8,777 (16.0); 8,771 (15,8); 8,490 (6.4); 8,470 (6,7); 8,319 (0.4); 8,273 (11.0); 8,251 (14.5); 8,126 (8,6); 8,120 (8,7); 8,103 (6.5); 8.098 (6.6); 7.976 (0.6); 7,656 (4,1); 7,644 (4.6); 7.637 (4.5); 7.625 (3.8); 7,121 (12,0); 7,115 (12: 1); 6,709 (0.6); 3,333 (43.9); 2,676 (0.6); 2,511 (70,7); 2,507 (90.6); 2,503 (70.5); 2.334 (0.5); 1,223 (0.7); 1,144 (0.7); 1,100 (0.4); 1.089 (0.9); 1.039 (0.6); 0.866 (0.3); 0.841 (0.4); 0.824 (0.3); 0.146 (0.5); 0,000 (99.6); -0.150 (0.5) 2- (pyridin-3-yl) -6- [3- (pyrimidin-2-yl) -1H-pyrazol-1-yl] -1,3-benzothiazole (30)
Unter Argon wurden 300 mg (1,03 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 753 mg (5,2 mmol) 2-(lH-Pyrazol-3-yl)pyrimidin, 16 mg (0,08 mmol) Kupfer(I)iodid, 427 mg (3,1 mmol) Kaliumcarbonat und 30 mg (0,1 mmol) trans-l,2-Bis(2'-pyridylideneamino)cyclohexan (racemisch) [herstellbar gemäß Chem. Eur. J. 2005, 2483] in ein Reaktionsgefäß eingewogen und 14,3 g DMF zugegeben. Der Ansatz wurde über Nacht unter Argon auf 120 °C erhitzt. Anschließend wurden noch einmal die oben genannten Mengen Kupfer(I)iodid und trans-l,2-Bis(2'-pyridylideneamino)cyclohexane (racemisch) zugesetzt und der Ansatz wurde unter Argon weitere 12 Stunden bei 120 °C gerührt. Der abgekühlte Ansatz wurde im Vakuum eingedampft, der Rückstand mit Wasser versetzt und mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden getrocknet, filtriert und eingedampft. Die Reinigung erfolgte chromatographisch per MPLC (Fließmittel Petrolether/Aceton). Man erhielt 92,0 mg (100 % Reinheit, 25,1 % d. Th.) der Titelverbindung (30). Under argon, 300 mg (1.03 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 753 mg (5.2 mmol) of 2- (1H-pyrazole 3-yl) pyrimidine, 16 mg (0.08 mmol) copper (I) iodide, 427 mg (3.1 mmol) potassium carbonate and 30 mg (0.1 mmol) trans-l, 2-bis (2'-bis) pyridylideneamino) cyclohexane (racemic) [can be prepared according to Chem. Eur. J. 2005, 2483] weighed into a reaction vessel and 14.3 g of DMF was added. The reaction was heated to 120 ° C overnight under argon. Subsequently, the above-mentioned amounts of copper (I) iodide and trans-l, 2-bis (2'-pyridylideneamino) cyclohexanes (racemic) were added again and the mixture was stirred under argon at 120 ° C for a further 12 hours. The cooled mixture was evaporated in vacuo, the residue was mixed with water and extracted several times with ethyl acetate. The combined organic phases were dried, filtered and evaporated. The purification was carried out by chromatography using MPLC (eluant petroleum ether / acetone). 92.0 mg (100% purity, 25.1% of theory) of the title compound (30) were obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 9,316 (0,6); 8,931 (2,0); 8,823 (3,0); 8,792 (0,7); 8,755 (3,7); 8,749 (3,8); 8,499 (1,7); 8,479 (1,7); 8,318 (0,7); 8,277 (2,2); 8,255 (4,1); 8,210 (2,0); 8,206 (2,0); 8,188 (1,0); 8,184 (1,1); 7,662 (0,9); 7,650 (1,1); 7,643 (1,1); 7,631 (0,9); 7,512 (1,0); 7,501 (1,6); 7,490 (0,9); 7,265 (3,8); 7,259 (4,0); 4,553 (2,6); 3,328 (28,5); 3,304 (0,4); 3,177 (0,5); 3,164 (0,5); 2,673 (0,4); 2,509 (50,4); 2,504 (66,9); 2,500 (51,8); 2,482 (5,0); 2,331 (0,4); 2,327 (0,3); 2,119 (7,4); 2,087 (0,4); 1,229 (0,5); 1,142 (16,0); 1,053 (0,9); 0,146 (0,4); 0,008 (2,9); 0,000 (73,9); -0,149 (0,4) 1 H NMR (400.0 MHz, de-DMSO): δ = 9.316 (0.6); 8,931 (2.0); 8.823 (3.0); 8,792 (0.7); 8,755 (3.7); 8,749 (3.8); 8,499 (1.7); 8.479 (1.7); 8.318 (0.7); 8.277 (2.2); 8,255 (4,1); 8.210 (2.0); 8.206 (2.0); 8.188 (1.0); 8.184 (1.1); 7.662 (0.9); 7.650 (1.1); 7.643 (1.1); 7,631 (0.9); 7,512 (1.0); 7,501 (1.6); 7,490 (0.9); 7.265 (3.8); 7.259 (4.0); 4,553 (2.6); 3,328 (28.5); 3.304 (0.4); 3.177 (0.5); 3.164 (0.5); 2,673 (0.4); 2,509 (50.4); 2,504 (66.9); 2,500 (51.8); 2,482 (5.0); 2,331 (0.4); 2,327 (0.3); 2,119 (7,4); 2,087 (0.4); 1,229 (0.5); 1,142 (16.0); 1,053 (0.9); 0.146 (0.4); 0.008 (2.9); 0,000 (73.9); -0.149 (0.4)
2-(Pyridin-3-yl)-6-(lH-l,2,4-triazol-l-yl)-l,3-benzothiazol (31) 2- (pyridin-3-yl) -6- (1H-l, 2,4-triazol-1-yl) -1,3-benzothiazole (31)
Unter Argon wurden 300 mg (1,03 mmol) 6-Brom-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-1), 938 mg (10,3 mmol) lH-l,2,4-triazole, 16 mg (0,08 mmol) Kupfer(I)iodid, 427 mg (3,1 mmol) Kaliumcarbonat und 30 mg (0,1 mmol) trans-l,2-Bis(2'-pyridylideneamino)cyclohexan (racemisch) [herstellbar gemäß Chem. Eur. J. 2005, 2483] in ein Reaktionsgefäß eingewogen und 19 g DMF zugegeben. Der Ansatz wurde anschließend mit 2 Tropfen Polyethylenglykol versetzt und über Nacht unter Argon auf 120 °C erhitzt. Der abgekühlte Ansatz wurde im Vakuum eingedampft, der Rückstand mit Wasser versetzt und mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden getrocknet, filtriert und eingedampft. Die Reinigung erfolgte chromatographisch per MPLC (Fließmittel Petrolether/Aceton). Man erhielt 60,0 mg (100 % Reinheit, 20,8 % d. Th.) der Titelverbindung (31). Under argon, 300 mg (1.03 mmol) of 6-bromo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-1), 938 mg (10.3 mmol) of 1H-l, 2, 4-triazoles, 16 mg (0.08 mmol) copper (I) iodide, 427 mg (3.1 mmol) potassium carbonate and 30 mg (0.1 mmol) trans-l, 2-bis (2'-pyridylideneamino) cyclohexane (racemic) [prepared according to Chem. Eur. J. 2005, 2483] weighed into a reaction vessel and added 19 g of DMF. The mixture was then mixed with 2 drops of polyethylene glycol and heated to 120 ° C overnight under argon. The cooled mixture was evaporated in vacuo, the residue was mixed with water and extracted several times with ethyl acetate. The combined organic phases were dried, filtered and evaporated. The purification was carried out by chromatography using MPLC (eluant petroleum ether / acetone). 60.0 mg (100% purity, 20.8% of theory) of the title compound (31) were obtained.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,399 (16,0); 9,307 (7,2); 9,303 (7,7); 8,789 (5,7); 8,777 (5,9); 8,756 (8,6); 8,751 (9,3); 8,563 (1,5); 8,500 (4,6); 8,480 (4,8); 8,314 (14,3); 8,298 (7,3); 8,276 (8,7); 8,114 (5,2); 8,108 (5,5); 8,091 (4,3); 8,086 (4,5); 7,982 (1,4); 7,661 (3,9); 7,649 (4,2); 7,641 (4,3); 7,629 (3,9); 3,325 (105,2); 2,673 (1,2); 2,503 (173,0); 2,330 (1,1); 0,146 (0,7); 0,000 (124,7); -0,150 (0,7) 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.399 (16.0); 9,307 (7.2); 9,303 (7,7); 8,789 (5.7); 8,777 (5.9); 8,756 (8,6); 8,751 (9.3); 8.563 (1.5); 8,500 (4.6); 8,480 (4.8); 8,314 (14,3); 8,298 (7.3); 8,276 (8,7); 8.114 (5.2); 8,108 (5.5); 8,091 (4.3); 8,086 (4,5); 7,982 (1.4); 7,661 (3.9); 7,649 (4.2); 7,641 (4.3); 7,629 (3.9); 3,325 (105.2); 2,673 (1.2); 2,503 (173,0); 2.330 (1.1); 0.146 (0.7); 0.000 (124.7); -0.150 (0.7)
5-(Ethylsulfanyl)-4-methyl-2- [2-(pyridin-3-yl)- 1 ,3-benzothiazol-6-yl] -2,4-dihydi 5- (ethylsulfanyl) -4-methyl-2- [2- (pyridin-3-yl) -1,3-benzothiazol-6-yl] -2,4-dihydric acid
l,2,4-triazol-3-on (52) l, 2,4-triazol-3-one (52)
Unter Argon wurden 200 mg (0,59 mmol) 6-Iod-2-(pyridin-3-yl)-l ,3-benzothiazol (I-a-2), 132 mg (0,83 mmol) 5-(Ethylsulfanyl)-4-methyl-2,4-dihydro-3H-l ,2,4-triazol-3-on, 1 1 mg (0,06 mmol) Kupfer(I)iodid, 245 mg (1 ,77 mmol) Kaliumcarbonat und 29 mg (0, 18 mmol) Kaliumiodid in 5 ml Dioxan vorgelegt und das Gefäß mit Argon geflutet. Anschließend wurden 17 mg (0, 12 mmol) trans-N,N'-Dimethylcyclohexan-l ,2-diamin (racemisch) hinzugegeben, das Reaktionsgefäß verschlossen und über Nacht bei 130 °C gerührt. Der abgekühlte Ansatz wurde mit 5 ml Ethylacetat verdünnt, über Celite filtriert und das Filtrat im Vakuum eingeengt. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließ mittel Wasser/ Acetonitril). Man erhielt 23,0 mg (99,0% Reinheit, 10,42% d. Th.) der Titelverbindung (52). Under argon, 200 mg (0.59 mmol) of 6-iodo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-2), 132 mg (0.83 mmol) of 5- (ethylsulfanyl) - 4-methyl-2,4-dihydro-3H-1, 2,4-triazol-3-one, 11.1mg (0.06mmol) copper (I) iodide, 245mg (1.77mmol) potassium carbonate and 29 submitted mg (0, 18 mmol) of potassium iodide in 5 ml of dioxane and flooded the vessel with argon. Subsequently, 17 mg (0.12 mmol) of trans-N, N'-dimethylcyclohexane-l, 2-diamine (racemic) were added, the reaction vessel was closed and stirred at 130 ° C overnight. The cooled mixture was diluted with 5 mL of ethyl acetate, filtered through Celite, and the filtrate was concentrated in vacuo. The Purification was carried out by chromatography using MPLC (flow medium water / acetonitrile). This gave 23.0 mg (99.0% purity, 10.42% of theory) of the title compound (52).
1H-NMR(400,0 MHz, de-DMSO): 5 = 9,269(1,7); 9,264(1,7); 8,767(1,2); 8,763(1,3); 8,755(1,3); 8,751(1,3); 8,672(2,4); 8,667(2,3); 8,462(0,8); 8,458(1,1); 8,452(0,9); 8,442(0,9); 8,437(1,1); 8,432(0,8); 8,208(1,1); 8,186(3,4); 8,169(2,3); 8,164(2,1); 8,147(0,7); 8,142(0,7); 7,643(1,0); 7,630(1,0); 7,623(0,9); 7,611(0,9); 5,753(2,1); 3,330(89,9); 3,325(76,7); 3,257(1,2); 3,239(3,7); 3,219(16,0); 3,202(1,3); 2,676(0,6); 2,671(0,8); 2,667(0,5); 2,524(2,1); 2,511(47,4); 2,507(99,4); 2,502(133,0); 2,498(94,5); 2,493(44,0); 2,333(0,6); 2,329(0,7); 2,324(0,6); 1,435(4,1); 1,417(8,7); 1,399(4,0); 0,146(0,7); 0,008(6,1); 0,000(169,2); -0,009(5,9); - 0,150(0,8) 1 H NMR (400.0 MHz, de-DMSO): 5 = 9.269 (1.7); 9,264 (1.7); 8,767 (1.2); 8.763 (1.3); 8,755 (1.3); 8.751 (1.3); 8,672 (2.4); 8,667 (2.3); 8,462 (0.8); 8.458 (1.1); 8,452 (0.9); 8.442 (0.9); 8,437 (1.1); 8,432 (0.8); 8,208 (1.1); 8,186 (3.4); 8.169 (2.3); 8,164 (2.1); 8.147 (0.7); 8,142 (0.7); 7.643 (1.0); 7,630 (1.0); 7,623 (0.9); 7,611 (0.9); 5,753 (2.1); 3,330 (89.9); 3,325 (76.7); 3.257 (1.2); 3,239 (3.7); 3,219 (16.0); 3,202 (1.3); 2,676 (0.6); 2,671 (0.8); 2,667 (0.5); 2,524 (2.1); 2,511 (47.4); 2,507 (99.4); 2.502 (133.0); 2,498 (94.5); 2,493 (44.0); 2,333 (0.6); 2.329 (0.7); 2,324 (0.6); 1.435 (4.1); 1,417 (8.7); 1,399 (4.0); 0.146 (0.7); 0.008 (6.1); 0.000 (169.2); -0.009 (5.9); - 0.150 (0.8)
4-Methyl-5- [(methylsulfanyl)methyl] -2- [2-(pyridin-3-yl)- 1 ,3-benzothiazol-6-yl] -2,4- dihydro-3H- 1 ,2,4-triazol-3-on (55) 4-Methyl-5- [(methylsulfanyl) methyl] -2- [2- (pyridin-3-yl) -1,3-benzothiazol-6-yl] -2,4-dihydro-3H-1, 2,4 -triazol-3-one (55)
Unter Argon wurden 200 mg (0,59 mmol) 6-Iod-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-2), 132 mg (0,83 mmol) 4-Methyl-5-[(methylsulfanyl)methyl]-2,4-dihydro-3H-l,2,4-triazol-3-on, 11 mg (0,06 mmol) Kupfer(I)iodid, 245 mg (1,77 mmol) Kaliumcarbonat und 29 mg (0,18 mmol) Kaliumiodid in 5 ml Dioxan vorgelegt und das Gefäß mit Argon geflutet. Anschließend wurden 17 mg (0,12 mmol) trans-N,N'-Dimethylcyclohexan-l,2-diamin (racemisch) hinzugegeben, das Reaktionsgefäß verschlossen und über Nacht bei 130 °C gerührt. Der abgekühlte Ansatz wurde mit 5 ml Ethylacetat verdünnt, über Celite filtriert und das Filtrat im Vakuum eingeengt. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittel n-Hexan/Ethylacetat). Man erhielt 120,0 mg (99,0% Reinheit, 54,4% d. Th.) der Titelverbindung (55). Under argon, 200 mg (0.59 mmol) of 6-iodo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-2), 132 mg (0.83 mmol) of 4-methyl-5- [(methylsulfanyl) methyl] -2,4-dihydro-3H-1, 2,4-triazol-3-one, 11mg (0.06mmol) copper (I) iodide, 245mg (1.77mmol) potassium carbonate and 29 mg (0.18 mmol) of potassium iodide in 5 ml of dioxane and flooded the vessel with argon. Then 17 mg (0.12 mmol) of trans-N, N'-dimethylcyclohexane-l, 2-diamine (racemic) were added, the reaction vessel was closed and stirred at 130 ° C overnight. The cooled mixture was diluted with 5 mL of ethyl acetate, filtered through Celite, and the filtrate was concentrated in vacuo. The purification was carried out by chromatography using MPLC (eluent n-hexane / ethyl acetate). 120.0 mg (99.0% purity, 54.4% of theory) of the title compound (55) were obtained.
1H-NMR(400,0 MHz, de-DMSO): 5 = 9,266(1,8); 9,260(1,8); 8,765(1,3); 8,762(1,4); 8,753(1,3); 8,750(1,4); 8,667(2,1); 8,664(2,1); 8,460(0,7); 8,455(1,0); 8,450(0,7); 8,440(0,8); 8,435(1,1); 8,430(0,8); 8,201(0,7); 8,179(3,2); 8,170(2,3); 8,165(2,2); 8,147(0,5); 8,142(0,5); 7,638(1,0); 7,627(0,9); 7,619(0,9); 7,606(0,9); 3,823(7,1); 3,316(45,8); 2,671(0,4); 2,525(0,9); 2,511(22,0); 2,507(46,4); 2,502(62,5); 2,498(44,8); 2,493(21,2); 2,329(0,4); 2,126(16,0); 0,000(1,1) 1 H NMR (400.0 MHz, de-DMSO): 5 = 9.266 (1.8); 9,260 (1.8); 8,765 (1.3); 8.762 (1.4); 8,753 (1.3); 8,750 (1.4); 8,667 (2.1); 8.664 (2.1); 8,460 (0.7); 8.455 (1.0); 8,450 (0.7); 8,440 (0.8); 8.435 (1.1); 8,430 (0.8); 8,201 (0.7); 8,179 (3.2); 8,170 (2.3); 8,165 (2.2); 8.147 (0.5); 8,142 (0.5); 7.638 (1.0); 7.627 (0.9); 7,619 (0.9); 7,606 (0.9); 3,823 (7.1); 3,316 (45.8); 2,671 (0.4); 2,525 (0.9); 2,511 (22.0); 2,507 (46.4); 2,502 (62.5); 2,498 (44.8); 2,493 (21.2); 2,329 (0.4); 2,126 (16.0); 0.000 (1.1)
4-Methyl-2-[2-(pyridin-3-yl)-l,3-benzothiazol-6-yl]-l,2,4-triazin-3,5(2H,4H)-dion (56) 4-Methyl-2- [2- (pyridin-3-yl) -1,3-benzothiazol-6-yl] -1,2,4-triazine-3,5 (2H, 4H) -dione (56)
Unter Argon wurden 200 mg (0,59 mmol) 6-Iod-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-2), 105 mg (0,83 mmol) 4-Methyl-l,2,4-triazin-3,5(2H,4H)-dion, 11 mg (0,06 mmol) Kupfer(I)iodid, 245 mg (1,77 mmol) Kaliumcarbonat und 29 mg (0,18 mmol) Kaliumiodid in 5 ml Dioxan vorgelegt und das Gefäß mit Argon geflutet. Anschließend wurden 17 mg (0,12 mmol) trans- N,N'-Dimethylcyclohexan-l,2-diamin (racemisch) hinzugegeben, das Reaktionsgefäß verschlossen und über Nacht bei 130 °C gerührt. Der abgekühlte Ansatz wurde mit 5 ml Ethylacetat verdünnt, über Celite filtriert und das Filtrat im Vakuum eingeengt. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittel n-Hexan/Ethylacetat). Man erhielt 20,0 mg (95,0% Reinheit, 9,5% d. Th.) der Titelverbindung (56). Under argon, 200 mg (0.59 mmol) of 6-iodo-2- (pyridin-3-yl) -l, 3-benzothiazole (Ia-2), 105 mg (0.83 mmol) of 4-methyl-1, 2,4-triazine-3,5 (2H, 4H) -dione, 11 mg (0.06 mmol) copper (I) iodide, 245 mg (1.77 mmol) potassium carbonate and 29 mg (0.18 mmol) potassium iodide presented in 5 ml of dioxane and flooded the vessel with argon. Subsequently, 17 mg (0.12 mmol) of trans-N, N'-dimethylcyclohexane-l, 2-diamine (racemic) were added, the reaction vessel was closed and stirred at 130 ° C overnight. The cooled mixture was diluted with 5 mL of ethyl acetate, filtered through Celite, and the filtrate was concentrated in vacuo. The purification was carried out by chromatography using MPLC (eluent n-hexane / ethyl acetate). 20.0 mg (95.0% purity, 9.5% of theory) of the title compound (56) were obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 9,302(2,2); 9,297(2,2); 8,791(1,6); 8,787(1,7); 8,779(1,7); 8,775(1,6); 8,502(0,9); 8,497(1,3); 8,492(0,9); 8,482(1,0); 8,477(1,3); 8,472(0,9); 8,373(2,8); 8,368(2,8); 8,222(2,6); 8,200(2,9); 7,809(6,0); 7,718(1,8); 7,712(1,7); 7,696(1,6); 7,690(1,6); 7,659(1,2); 7,647(1,2); 7,640(1 ,1); 7,628(1,1); 3,316(69,3); 3,246(16,0); 2,675(0,5); 2,671(0,6); 2,666(0,5); 2,510(40,9); 2,506(79,3); 2,502(102,5); 2,497(74,0); 2,333(0,5); 2,328(0,6); 2,324(0,4); 0,008(2,6); 0,000(49,1); -0,008(1,9) 1 H NMR (400.0 MHz, de-DMSO): δ = 9.302 (2.2); 9,297 (2.2); 8.791 (1.6); 8,787 (1.7); 8,779 (1.7); 8,775 (1.6); 8,502 (0.9); 8,497 (1.3); 8.492 (0.9); 8,482 (1.0); 8,477 (1.3); 8,472 (0.9); 8.373 (2.8); 8,368 (2.8); 8.222 (2.6); 8,200 (2.9); 7,809 (6.0); 7,718 (1.8); 7,712 (1.7); 7,696 (1.6); 7,690 (1.6); 7.659 (1.2); 7.647 (1.2); 7.640 (1, 1); 7.628 (1.1); 3,316 (69.3); 3,246 (16.0); 2,675 (0.5); 2,671 (0.6); 2,666 (0.5); 2,510 (40.9); 2,506 (79.3); 2.502 (102.5); 2,497 (74.0); 2,333 (0.5); 2,328 (0.6); 2,324 (0.4); 0.008 (2.6); 0,000 (49.1); -0.008 (1.9)
Synthese von Verbindunsen der Formel (I) nach Methode F Synthesis of Compounds of Formula (I) by Method F
2-(Pyridin-3-yl)-6-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)- 1 ,3-benzothiazol (I-h- 1) 2- (pyridin-3-yl) -6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,3-benzothiazole (Ih-1)
1,50 g (4,43 mmol) 6-Iod-2-(pyridin-3-yl)-l,3-benzothiazol (I-a-2) und 1,35 g (5,32 mmol) Bis(pinacolato)diboron wurden in 48 ml Acetonnitril in einem Mikrowellengefäß vorgelegt, 1,31 g (13,3 mmol) Kaliumacetat zugegeben und anschließend zur Entgasung Argon durch diese Mischung geleitet. 181 mg (0,22 mmol) (l,l'-Bis(diphenylphosphino)ferrocene)- palladium(II)-dichlorid (Dichlormethankomplex) wurden zugesetzt und das Gefäß erneut mit Argon geflutet. Das Reaktionsgefäß wurde verschlossen und der Ansatz in einer CEM- Mikrowelle für 25 Minuten bei 140 °C zur Reaktion gebracht. Anschließend wurde die Reaktionslösung mit 10 ml Ethylacetat verdünnt, über Celite filtriert und das Filtrat im Vakuum eingeengt. Die Reinigung erfolgte chromatographisch mittels MPLC. Man erhielt 870 mg (95,0% Reinheit, 55,1% d. Th.) der Titelverbindung (I-h-1). 1.50 g (4.43 mmol) of 6-iodo-2- (pyridin-3-yl) -1,3-benzothiazole (Ia-2) and 1.35 g (5.32 mmol) of bis (pinacolato) diboron were placed in 48 ml of acetonitrile in a microwave vessel, added 1.31 g (13.3 mmol) of potassium acetate and then passed to degassing argon through this mixture. 181 mg (0.22 mmol) of (1,1'-bis (diphenylphosphino) ferrocenes) palladium (II) dichloride (dichloromethane complex) were added and the vessel was again flooded with argon. The reaction vessel was closed and the reaction was allowed to react in a CEM microwave at 140 ° C for 25 minutes. Subsequently, the reaction solution was diluted with 10 ml of ethyl acetate, filtered through Celite and the filtrate was concentrated in vacuo. The purification was carried out by chromatography using MPLC. 870 mg (95.0% purity, 55.1% of theory) of the title compound (I-h-1) were obtained.
1H-NMR(400,0 MHz, de-DMSO): 5 = 9,291(0,7); 9,286(0,8); 8,782(0,5); 8,778(0,5); 8,770(0,5); 8,766(0,5); 8,514(1,2); 8,487(0,4); 8,467(0,4); 8,114(0,8); 8,093(0,9); 7,930(1,2); 7,843(0,6); 7,823(0,5); 7,646(0,4); 7,634(0,4); 7,626(0,4); 7,614(0,4); 3,927(2,3); 3,325(10,2); 2,509(8,2); 2,504(10,7); 2,500(7,9); 1,342(15,3); 1,168(1,5); 1,160(16,0); 1,072(15,9) 1 H NMR (400.0 MHz, de-DMSO): 5 = 9.291 (0.7); 9.286 (0.8); 8.782 (0.5); 8,778 (0.5); 8,770 (0.5); 8.766 (0.5); 8,514 (1.2); 8,487 (0.4); 8,467 (0.4); 8,114 (0.8); 8,093 (0.9); 7,930 (1.2); 7,843 (0.6); 7,823 (0.5); 7,646 (0.4); 7,634 (0.4); 7,626 (0.4); 7,614 (0.4); 3,927 (2.3); 3,325 (10.2); 2,509 (8.2); 2,504 (10.7); 2,500 (7.9); 1,342 (15.3); 1.168 (1.5); 1,160 (16.0); 1.072 (15.9)
4-Brom-l-[(methylsulfanyl)methyl]-lH-pyrazol 4-bromo-l - [(methylsulfanyl) methyl] -lH-pyrazole
B B
1,0 g (6,8 mmol) 4-Brom-lH-pyrazol wurden unter Argon in 30 ml DMF gelöst, bei 0 °C portionsweise mit 408 mg (10,2 mmol) Natriumhydrid (60%ige Dispersion in Paraffin) versetzt und 15 Minuten in der Kälte gerührt. Anschließend wurden 1,31 g (13,6 mmol) Chlordimethylsulfid zugeben und die Mischung über Nacht bei Raumtemperatur gerührt. Zur Aufarbeitung wurde der Ansatz vorsichtig mit Wasser versetzt und mit Ethylacetet mehrfach extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und das Filtrat im Vakuum eingedampft. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittelgradient n-Hexan/Ethylacetat). Man erhielt 1,1 g (99,0% Reinheit, 77,3% d. Th.) der Titelverbindung 4-Brom-l-[(methylsulfanyl)methyl]-lH-pyrazol. 1.0 g (6.8 mmol) of 4-bromo-1H-pyrazole were dissolved in 30 ml of DMF under argon, and 408 mg (10.2 mmol) of sodium hydride (60% dispersion in paraffin) were added in portions at 0 ° C and stirred in the cold for 15 minutes. Subsequently, 1.31 g (13.6 mmol) of chlorodimethylsulfide was added and the mixture was stirred at room temperature overnight. For workup, the mixture was carefully mixed with water and extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and the filtrate evaporated in vacuo. The purification was carried out by chromatography using MPLC (eluent gradient n-hexane / ethyl acetate). 1.1 g (99.0% purity, 77.3% of theory) of the title compound 4-bromo-1 - [(methylsulfanyl) methyl] -1H-pyrazole were obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 8,069(3,9); 7,591(3,5); 5,243(9,6); 3,317(4,6); 2,511(2,9); 2,506(5,9); 2,502(7,9); 2,497(5,7); 2,493(2,8); 2,121(16,0); 0,000(3,4) 1 H NMR (400.0 MHz, de-DMSO): δ = 8.069 (3.9); 7,591 (3.5); 5,243 (9.6); 3,317 (4.6); 2,511 (2.9); 2,506 (5.9); 2,502 (7.9); 2,497 (5.7); 2,493 (2.8); 2,121 (16.0); 0.000 (3.4)
6- { 1- [(Methylsulfanyl)methyl] - lH-pyrazol-4-yl} -2-(pyridin-3-yl)- 1 ,3-benzothiazol (38) 6- {1- [(Methylsulfanyl) methyl] -1H-pyrazol-4-yl} -2- (pyridin-3-yl) -1,3-benzothiazole (38)
91 mg (0,44 mmol) 4-Brom-l-[(methylsulfanyl)methyl]-lH-pyrazol wurden in 4 ml eines entgasten 1 : 1 Gemisches aus Wasser und 1 ,2-Dimethoxyethan in einem Mikrowellengefäß vorgelegt und 83 mg (0,6 mmol) Kaliumcarbonat sowie 150 mg (0,4 mmol) 2-(Pyridin-3-yl)-6- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3-benzothiazol (I-h-1) zugegeben. Das Reaktionsgemisch wurde anschließend in einer CEM-Mikrowelle für eine Stunde auf 100 °C erhitzt. Danach wurde die Mischung mit Wasser versetzt und mehrfach mit Ethylacetat extrahiert, über Celite filtriert und eingeengt. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 44 mg (90% Reinheit, 29,3% d. Th.) der Titelverbindung (38). 91 mg (0.44 mmol) of 4-bromo-1 - [(methylsulfanyl) methyl] -1H-pyrazole were initially charged in 4 ml of a degassed 1: 1 mixture of water and 1,2-dimethoxyethane in a microwave vessel and 83 mg of 0.6 mmol) potassium carbonate and 150 mg (0.4 mmol) of 2- (pyridin-3-yl) -6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -l, 3-benzothiazole (Ih-1) added. The reaction mixture was then heated to 100 ° C in a CEM microwave for one hour. Thereafter, the mixture was added with water and extracted several times with ethyl acetate, filtered through Celite and concentrated. The purification was carried out by chromatography using MPLC (solvent gradient water / acetonitrile). 44 mg (90% purity, 29.3% of theory) of the title compound (38) were obtained.
1H-NMR(400,0 MHz, de-DMSO): 5 = 9,276(1,9); 9,270(1,8); 8,762(1,4); 8,758(1,5); 8,750(1,4); 8,746(1,5); 8,468(0,8); 8,463(1,1); 8,458(0,9); 8,447(3,0); 8,443(3,5); 8,438(1,1); 8,403(3,6); 8,103(2,1); 8,081(2,9); 8,078(4,0); 7,844(1,5); 7,839(1,5); 7,822(1,3); 7,818(1,3); 7,639(1,0); 7,637(1,1); 7,627(1,2); 7,625(1,3); 7,617(1,1); 7,607(1,0); 7,605(1,0); 5,755(0,4); 5,308(7,6); 3,318(43,5); 2,671(0,4); 2,525(0,9); 2,520(1,4); 2,511(23,1); 2,507(49,4); 2,502(66,9); 2,498(48,5); 2,493(23,2); 2,329(0,4); 2,190(16,0); 0,000(8,8) 1 H NMR (400.0 MHz, de-DMSO): 5 = 9.276 (1.9); 9,270 (1.8); 8.762 (1.4); 8.758 (1.5); 8,750 (1.4); 8,746 (1.5); 8,468 (0.8); 8.463 (1.1); 8.458 (0.9); 8,447 (3.0); 8,443 (3.5); 8,438 (1.1); 8.403 (3.6); 8,103 (2.1); 8,081 (2.9); 8.078 (4.0); 7,844 (1.5); 7.839 (1.5); 7,822 (1.3); 7,818 (1.3); 7,639 (1.0); 7,637 (1.1); 7.627 (1.2); 7,625 (1.3); 7,617 (1.1); 7,607 (1.0); 7,605 (1.0); 5,755 (0.4); 5,308 (7.6); 3,318 (43.5); 2,671 (0.4); 2,525 (0.9); 2,520 (1.4); 2,511 (23.1); 2,507 (49.4); 2,502 (66.9); 2,498 (48.5); 2,493 (23.2); 2,329 (0.4); 2,190 (16.0); 0.000 (8.8)
6-{l-[(Methylsulfinyl)methyl]-lH-pyrazol-4-yl}-2-(pyridin-3-yl)-l,3-benzothiazol (39) 6- {1 - [(Methylsulfinyl) methyl] -1H-pyrazol-4-yl} -2- (pyridin-3-yl) -1,3-benzothiazole (39)
70,0 mg (0,18 mmol) 6-{l-[(Methylsulfanyl)methyl]-lH-pyrazol-4-yl}-2-(pyridin-3-yl)-l,3- benzothiazol (38) wurden in 3 ml Dichlormethan vorgelegt und bei 0 °C mit 41,0 mg (0,18 mmol) meta-Chlorperbenzoesäure (77%ig) versetzt. Der Ansatz wurde bis zum vollständigen Umsatz des Edukts (ca. 40 min, DC-Kontrolle) bei Raumtemperatur gerührt. Anschließend wurde mit gesättigter wässriger Natriumcarbonatlösung versetzt und die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden getrocknet, filtriert und eingeengt. Die Reinigung des Rückstandes erfolgte chromatographisch mittels MPLC (Fließmittelgradient Wasser/Acetonitril). Man erhielt 25,0 mg (90% Reinheit, 35,3% d. Th.) der Titelverbindung (39). 70.0 mg (0.18 mmol) of 6- {1 - [(methylsulfanyl) methyl] -1H-pyrazol-4-yl} -2- (pyridin-3-yl) -1,3-benzothiazole (38) initially charged in 3 ml of dichloromethane and at 0 ° C with 41.0 mg (0.18 mmol) meta-chloroperbenzoic acid (77%) was added. The mixture was stirred until complete conversion of the starting material (about 40 minutes, TLC check) at room temperature. Subsequently, it was mixed with saturated aqueous sodium carbonate solution and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried, filtered and concentrated. The residue was purified by chromatography using MPLC (solvent gradient water / acetonitrile). 25.0 mg (90% pure, 35.3% of theory) of the title compound (39) were obtained.
1H-NMR(400,0 MHz, de-DMSO): 5 = 9,278(2,2); 9,273(2,1); 8,763(1,6); 8,760(1,6); 8,751(1,7); 8,748(1,6); 8,490(0,3); 8,480(2,8); 8,476(2,9); 8,470(1,1); 8,465(1,3); 8,460(0,9); 8,450(1,1); 8,445(1,4); 8,440(1,0); 8,421(0,4); 8,335(4,3); 8,250(0,4); 8,218(4,5); 8,114(2,4); 8,105(0,4); 8,093(2,9); 7,865(1,8); 7,861(1,7); 7,844(1,5); 7,840(1,5); 7,639(1,2); 7,627(1,3); 7,619(1,2); 7,608(1,2); 5,803(0,5); 5,569(2,0); 5,536(2,6); 5,348(2,7); 5,315(2,1); 3,322(7,5); 3,078(1,1); 2,672(0,3); 2,595(16,0); 2,525(0,7); 2,512(19,6); 2,507(41,7); 2,503(56,5); 2,498(41,0); 2,494(19,7); 0,146(0,4); 0,008(2,9); 0,000(82,7); -0,009(2,9); -0,150(0,4) 1 H NMR (400.0 MHz, de-DMSO): 5 = 9.278 (2.2); 9.273 (2.1); 8.763 (1.6); 8,760 (1.6); 8.751 (1.7); 8.748 (1.6); 8,490 (0.3); 8,480 (2.8); 8,476 (2.9); 8,470 (1.1); 8,465 (1.3); 8,460 (0.9); 8,450 (1.1); 8,445 (1.4); 8,440 (1.0); 8,421 (0.4); 8,335 (4.3); 8,250 (0.4); 8,218 (4.5); 8,114 (2.4); 8,105 (0.4); 8,093 (2.9); 7,865 (1.8); 7,861 (1.7); 7,844 (1.5); 7,840 (1.5); 7,639 (1.2); 7.627 (1.3); 7,619 (1.2); 7,608 (1.2); 5,803 (0.5); 5,569 (2.0); 5,536 (2.6); 5,348 (2.7); 5,315 (2.1); 3,322 (7.5); 3,078 (1.1); 2,672 (0.3); 2,595 (16.0); 2,525 (0.7); 2,512 (19.6); 2,507 (41.7); 2,503 (56.5); 2,498 (41.0); 2,494 (19.7); 0.146 (0.4); 0.008 (2.9); 0,000 (82.7); -0.009 (2.9); -0.150 (0.4)
Synthese von Verbindungen der Formel (I) nach Methode G Synthesis of compounds of the formula (I) according to Method G
2-(Pyridin-3-yl)- 1 ,3-benzothiazol-6-carbonsäure (I-k- 1) 2- (pyridin-3-yl) -1,3-benzothiazole-6-carboxylic acid (I-k-1)
Zu einer gerührten Lösung von 6,0 g (25,29 mmol) 2-(Pyridin-3-yl)-l,3-benzothiazol-6- carbonitril (I-a-3) (hergestellt analog der Synthese zur Verbindung (I-a-2), im Unterschied ausgehend von 4-Amino-3-brombenzonitril in Methode A, Schritt 1) in 80 ml Essigsäure wurden 100 ml konzentrierte Salzsäure zugesetzt und das Gemisch für 16 Stunden bei 80 °C gerührt. Die Reaktionsmischung wurde anschließend im Vakuum eingedampft. Der Rückstand wurde mit 30 ml Dichlormethan trituriert. Man erhielt 5,60 g 2-(Pyridin-3-yl)-l ,3-benzothiazol- 6-carbonsäure (I-k-1) als Rohprodukt, das ohne weitere Reinigung weiter zu Amiden umgesetzt wurde. Hierfür wurde eine Reinheit von 100% angenommen. To a stirred solution of 6.0 g (25.29 mmol) of 2- (pyridin-3-yl) -1,3-benzothiazole-6-carbonitrile (Ia-3) (prepared analogously to the synthesis of the compound (Ia-2 ), in difference starting from 4-amino-3-bromobenzonitrile in method A, step 1) in 80 ml of acetic acid, 100 ml of concentrated hydrochloric acid were added and the mixture was stirred at 80 ° C. for 16 hours. The reaction mixture was then evaporated in vacuo. The residue was triturated with 30 ml of dichloromethane. This gave 5.60 g of 2- (pyridin-3-yl) -1,3-benzothiazole-6-carboxylic acid (Ik-1) as a crude product, which was reacted further to amides without further purification. For this purpose, a purity of 100% was assumed.
LC-MS: m/z 257 [M+H+] LC-MS: m / z 257 [M + H + ]
2-(5-Fluorpyridin-3-yl)- 1 ,3-benzothiazol-6-carbonsäure (I-k-2)  2- (5-fluoropyridin-3-yl) -1,3-benzothiazole-6-carboxylic acid (I-k-2)
Die Herstellung erfolgte in Analogie zur Synthese von (I-k-1), im Unterschied ausgehend von 3-(Chlorcarbonyl)-5-fluorpyridiniumchlorid in Methode A, Schritt 1. The preparation was carried out in analogy to the synthesis of (Ik-1), in contrast starting from 3- (chlorocarbonyl) -5-fluoropyridinium chloride in method A, step 1.
LC-MS: m/z 275 [M+H+] LC-MS: m / z 275 [M + H + ]
2-(Pyridin-3-yl)-N-(2,2,2-trifluorethyl)-l,3-benzothiazol-6-carboxamid (32) 2- (pyridin-3-yl) -N- (2,2,2-trifluoroethyl) -1,3-benzothiazole-6-carboxamide (32)
250 mg (1,0 mmol) 2-(Pyridin-3-yl)-l,3-benzothiazol-6-carbonsäure wurden in der Siedehitze mittels eines deutlichen Überschusses Thionylchlorid in das Säurechlorid überführt. Überschüssiges Thionylchlorid wurde im Vakuum entfernt und der Rückstand unter Argon mit 20 ml Dichlormethan versetzt. Anschließend wurden 99 mg (1,0 mmol) 2,2,2-Trifluorethylamin und 202 mg (2 mmol) Triethylamin zugegeben und der Ansatz bei Raumtemperatur über Nacht gerührt. Anschließend wurde eingedampft und der Rückstand chromatographisch mittels MPLC gereinigt (Fließmittel Cyclohexan/Aceton). Man erhielt 330,0 mg (95 % Reinheit, 95,3 % d. Th.) der Titelverbindung (32). 1H-NMR(399,9 MHz, d6-DMSO): δ = 9,290 (0,6); 9,289 (0,6); 9,285 (0,6); 9,086 (0,3); 8,780 (0,5); 8,776 (0,5); 8,768 (0,5); 8,764 (0,5); 8,703 (0,8); 8,700 (0,8); 8,478 (0,3); 8,473 (0,4); 8,468 (0,3); 8,458 (0,3); 8,453 (0,4); 8,452 (0,4); 8,448 (0,3); 8,192 (0,6); 8,171 (0,8); 8,077 (0,6); 8,072 (0,6); 8,055 (0,4); 8,051 (0,4); 7,637 (0,4); 7,635 (0,3); 7,625 (0,4); 7,623 (0,3); 7,617 (0,3); 7,615 (0,3); 7,605 (0,3); 7,603 (0,3); 4,156 (0,5); 4,140 (0,5); 4,132 (0,5); 4,116 (0,5); 3,133 (16,0); 2,502 (1,0); 2,498 (1,8); 2,493 (2,5); 2,489 (1,8); 2,484 (0,9); 0,000 (0,8) 250 mg (1.0 mmol) of 2- (pyridin-3-yl) -1,3-benzothiazole-6-carboxylic acid were converted into the acid chloride at boiling temperature by means of a significant excess of thionyl chloride. Excess thionyl chloride was removed in vacuo and the residue was added under argon with 20 ml of dichloromethane. Then, 99 mg (1.0 mmol) of 2,2,2-trifluoroethylamine and 202 mg (2 mmol) of triethylamine were added, and the reaction was stirred at room temperature overnight. It was then evaporated and the residue was purified by chromatography using MPLC (mobile phase cyclohexane / acetone). 330.0 mg (95% pure, 95.3% of theory) of the title compound (32) were obtained. 1 H NMR (399.9 MHz, d 6 -DMSO): δ = 9.290 (0.6); 9,289 (0.6); 9.285 (0.6); 9.086 (0.3); 8,780 (0.5); 8.776 (0.5); 8.768 (0.5); 8.764 (0.5); 8,703 (0.8); 8,700 (0.8); 8.478 (0.3); 8.473 (0.4); 8.468 (0.3); 8.458 (0.3); 8.453 (0.4); 8.452 (0.4); 8.448 (0.3); 8,192 (0.6); 8,171 (0.8); 8.077 (0.6); 8,072 (0.6); 8.055 (0.4); 8,051 (0.4); 7.637 (0.4); 7.635 (0.3); 7.625 (0.4); 7.623 (0.3); 7.617 (0.3); 7.615 (0.3); 7.605 (0.3); 7.603 (0.3); 4.156 (0.5); 4.140 (0.5); 4,132 (0.5); 4.116 (0.5); 3.133 (16.0); 2,502 (1.0); 2,498 (1.8); 2,493 (2.5); 2.489 (1.8); 2.484 (0.9); 0,000 (0.8)
2-(Pyridin-3-yl)-N-(pyridin-2-ylmethyl)-l,3-benzothiazol-6-carboxamid (33) 2- (pyridin-3-yl) -N- (pyridin-2-ylmethyl) -1,3-benzothiazole-6-carboxamide (33)
250 mg (1 mmol) 2-(Pyridin-3-yl)-l,3-benzothiazol-6-carbonsäure wurden in der Siedehitze mittels eines deutlichen Überschusses Thionylchlorid in das Säurechlorid überführt. Überschüssiges Thionylchlorid wurde im Vakuum entfernt und der Rückstand unter Argon mit 20 ml Dichlormethan versetzt. Anschließend wurden 108 mg (1 mmol) 2-Picolylamin und 202 mg (2 mmol) Triethylamin zugegeben und der Ansatz wurde bei Raumtemperatur über Nacht gerührt. Anschließend wurde eingedampft und der Rückstand chromatographisch mittels MPLC gereinigt (Fließmittel Cyclohexan/Aceton). Man erhielt 290,0 mg (97 % Reinheit, 83,3 % d. Th.) der Titelverbindung (33). 250 mg (1 mmol) of 2- (pyridin-3-yl) -1,3-benzothiazole-6-carboxylic acid were converted into the acid chloride at boiling temperature by means of a significant excess of thionyl chloride. Excess thionyl chloride was removed in vacuo and the residue was added under argon with 20 ml of dichloromethane. Then, 108 mg (1 mmol) of 2-picolylamine and 202 mg (2 mmol) of triethylamine were added, and the reaction was stirred at room temperature overnight. It was then evaporated and the residue was purified by chromatography using MPLC (mobile phase cyclohexane / acetone). 290.0 mg (97% purity, 83.3% of theory) of the title compound (33) were obtained.
1H-NMR(399,9 MHz, d6-DMSO): δ = 9,291 (3,4); 9,289 (3,5); 9,285 (3,6); 9,283 (3,3); 9,085 (0,9); 9,071 (1,5); 9,057 (0,9); 8,777 (2,9); 8,773 (3,1); 8,765 (3,1); 8,761 (3,0); 8,723 (4,6); 8,720 (4,6); 8,653 (0,2); 8,642 (0,2); 8,530 (2,2); 8,528 (2,4); 8,526 (2,3); 8,520 (2,4); 8,518 (2,5); 8,475 (4,9); 8,471 (5,9); 8,466 (4,1); 8,461 (4,0); 8,456 (4,1); 8,451 (2,9); 8,450 (2,7); 8,446 (2,1); 8,182 (3,1); 8,161 (5,7); 8,115 (3,8); 8,111 (3,7); 8,094 (2,1); 8,089 (2,1); 8,009 (0,2); 7,989 (0,3); 7,863 (0,2); 7,792 (0,2); 7,787 (0,2); 7,777 (1,5); 7,772 (1,7); 7,757 (2,9); 7,753 (2,9); 7,738 (2,0); 7,733 (2,4); 7,731 (2,6); 7,727 (2,4); 7,712 (4,4); 7,707 (4,4); 7,693 (2,7); 7,688 (2,6); 7,651 (0,2); 7,634 (2,2); 7,632 (2,1); 7,622 (2,2); 7,620 (2,1); 7,614 (2,2); 7,613 (2,1); 7,602 (2,1); 7,600 (2,0); 7,469 (0,2); 7,466 (0,2); 7,457 (0,2); 7,454 (0,2); 7,450 (0,3); 7,447 (0,3); 7,438 (0,4); 7,407 (5,9); 7,387 (5,2); 7,324 (0,2); 7,275 (1,8); 7,263 (1,8); 7,261 (1,8); 7,257 (1,8); 7,244 (1,6); 7,220 (0,3); 7,203 (2,7); 7,190 (2,8); 7,185 (2,7); 7,172 (2,3); 4,941 (0,7); 4,938 (0,6); 4,649 (6,6); 4,635 (6,5); 4,581 (0,2); 3,892 (0,3); 3,859 (0,4); 3,811 (16,0); 3,400 (0,3); 3,383 (0,3); 3,374 (0,3); 3,368 (0,3); 3,321 (0,3); 3,264 (0,6); 3,188 (1,0); 3,019 (4,2); 2,737 (0,5); 2,671 (0,4); 2,667 (0,4); 2,662 (0,4); 2,657 (0,4); 2,626 (0,3); 2,580 (0,3); 2,571 (0,3); 2,561 (0,3); 2,531 (1,2); 2,502 (7,0); 2,498 (13,3); 2,493 (17,9); 2,488 (12,6); 2,484 (6,2); 1,977 (0,6); 1,940 (0,2); 1,928 (0,2); 1,264 (0,2); 1,241 (0,5); 1,179 (0,3); 1,161 (0,3); 0,008 (0,3); 0,000 (4,7) N-[2-(Methylsulfanyl)ethyl]-2-(pyridin-3-yl)-l,3-benzothiazol-6-carboxamid (69) 1 H NMR (399.9 MHz, d 6 -DMSO): δ = 9.291 (3.4); 9,289 (3,5); 9.285 (3.6); 9.283 (3.3); 9.085 (0.9); 9.071 (1.5); 9.057 (0.9); 8,777 (2.9); 8,773 (3,1); 8,765 (3.1); 8,761 (3.0); 8,723 (4,6); 8,720 (4,6); 8.653 (0.2); 8.642 (0.2); 8.530 (2.2); 8.528 (2.4); 8.526 (2.3); 8.520 (2.4); 8.518 (2.5); 8.475 (4.9); 8,471 (5.9); 8,466 (4,1); 8.461 (4.0); 8,456 (4,1); 8.451 (2.9); 8,450 (2.7); 8.446 (2.1); 8,182 (3,1); 8,161 (5,7); 8,115 (3,8); 8,111 (3,7); 8.094 (2.1); 8,089 (2.1); 8.009 (0.2); 7.989 (0.3); 7.863 (0.2); 7,792 (0.2); 7.787 (0.2); 7,777 (1.5); 7,772 (1.7); 7,757 (2.9); 7,753 (2.9); 7,738 (2.0); 7.733 (2.4); 7,731 (2.6); 7,727 (2,4); 7,712 (4.4); 7,707 (4.4); 7,693 (2.7); 7,688 (2.6); 7.651 (0.2); 7.634 (2.2); 7,632 (2,1); 7.622 (2.2); 7,620 (2,1); 7.614 (2.2); 7.613 (2.1); 7.602 (2.1); 7,600 (2.0); 7.469 (0.2); 7.466 (0.2); 7.457 (0.2); 7.454 (0.2); 7,450 (0.3); 7.447 (0.3); 7.438 (0.4); 7,407 (5.9); 7,387 (5.2); 7,324 (0.2); 7.275 (1.8); 7.263 (1.8); 7.261 (1.8); 7.257 (1.8); 7.244 (1.6); 7.220 (0.3); 7,203 (2,7); 7,190 (2.8); 7.185 (2.7); 7,172 (2,3); 4,941 (0.7); 4,938 (0.6); 4,649 (6.6); 4,635 (6.5); 4,581 (0.2); 3,892 (0.3); 3.859 (0.4); 3,811 (16.0); 3,400 (0.3); 3.383 (0.3); 3,374 (0.3); 3,368 (0.3); 3,321 (0.3); 3,264 (0.6); 3.188 (1.0); 3,019 (4.2); 2,737 (0.5); 2,671 (0.4); 2,667 (0.4); 2,662 (0.4); 2,657 (0.4); 2,626 (0.3); 2,580 (0.3); 2,571 (0.3); 2.561 (0.3); 2.531 (1.2); 2,502 (7.0); 2,498 (13.3); 2,493 (17.9); 2,488 (12,6); 2,484 (6.2); 1,977 (0.6); 1,940 (0.2); 1.928 (0.2); 1,264 (0.2); 1,241 (0.5); 1.179 (0.3); 1.161 (0.3); 0.008 (0.3); 0,000 (4,7) N- [2- (methylsulfanyl) ethyl] -2- (pyridin-3-yl) -1,3-benzothiazole-6-carboxamide (69)
Zu einer Lösung von 200 mg (0,78 mmol, angenommene Reinheit 100%) 2-(Pyridin-3-yl)-l,3- benzothiazol-6-carbonsäure (I-k-1) in 6 ml Dioxan wurden 3 Moläquivalente (eq.) Propylphosphonicanhydrid (T3P) sowie 5 Moläquivalente (eq.) Triethylamin gegeben. Anschließend wurden 85,4 mg (0,94 mmol, 1,2 eq.) 2-(Methylsulfanyl)ethanamin zugesetzt. Der Ansatz wurde für 16 Stunden bei 50 °C gerührt und anschließend im Vakuum eingedampft. Die Aufreinigung erfolgte chromatographisch mittels MPLC. Man erhielt 47,1 mg (99% Reinheit, 18,2% d. Th.) der Titelverbindung (69). 1H-NMR(400,0 MHz, de-DMSO): δ = 9,311(1,1); 8,791(1,7); 8,673(2,3); 8,670(2,4); 8,503(1,0). 8,483(1,0); 8,195(1,7); 8,173(2,2); 8,044(1,3); 8,040(1,3); 8,022(1,0); 8,018(1,0); 7,662(0,8); 7,650(0,8). 7,643(0,8); 7,631(0,7); 3,902(4,4); 3,534(0,8); 3,518(1,6); 3,500(1,6); 3,485(0,9); 3,337(125,1). 2,711(1,7); 2,693(2,5); 2,676(1,9); 2,525(1,4); 2,508(61,7); 2,503(86,2); 2,499(65,5); 2,334(0,4). 2,330(0,5); 2,326(0,4); 2,123(16,0); 0,000(3,7) N-[2-(Methylsulfonyl)ethyl]-2-(pyridin-3-yl)-l,3-benzothiazol-6-carboxamid (71) To a solution of 200 mg (0.78 mmol, assumed purity 100%) of 2- (pyridin-3-yl) -1,3-benzothiazole-6-carboxylic acid (Ik-1) in 6 ml of dioxane was added 3 molar equivalents (eq .) Propylphosphonicanhydrid (T3P) and 5 molar equivalents (eq.) Of triethylamine. Then, 85.4 mg (0.94 mmol, 1.2 eq.) Of 2- (methylsulfanyl) ethanamine was added. The batch was stirred for 16 hours at 50 ° C and then evaporated in vacuo. The purification was carried out by chromatography using MPLC. 47.1 mg (99% purity, 18.2% of theory) of the title compound (69) were obtained. 1 H NMR (400.0 MHz, de-DMSO): δ = 9.311 (1.1); 8.791 (1.7); 8,673 (2.3); 8,670 (2.4); 8,503 (1.0). 8,483 (1.0); 8,195 (1.7); 8,173 (2.2); 8.044 (1.3); 8,040 (1.3); 8,022 (1.0); 8,018 (1.0); 7,662 (0.8); 7,650 (0.8). 7.643 (0.8); 7,631 (0.7); 3,902 (4.4); 3,534 (0.8); 3,518 (1.6); 3,500 (1.6); 3,485 (0.9); 3.337 (125.1). 2,711 (1.7); 2,693 (2.5); 2,676 (1.9); 2,525 (1.4); 2,508 (61.7); 2,503 (86.2); 2,499 (65.5); 2,334 (0.4). 2,330 (0.5); 2,326 (0.4); 2,123 (16.0); 0.000 (3.7) N - [2- (methylsulfonyl) ethyl] -2- (pyridin-3-yl) -1,3-benzothiazole-6-carboxamide (71)
Zu einer Lösung von 200 mg (0,78 mmol, angenommene Reinheit 100%) 2-(Pyridin-3-yl)-l,3- benzothiazol-6-carbonsäure (I-k-1) in 6 ml Dioxan wurden 3 Moläquivalente (eq.) Propylphosphonicanhydrid (T3P) sowie 5 Moläquivalente (eq.) Triethylamin gegeben. Anschließend wurden 115,78 mg (0,94 mmol, 1,2 eq.) 2-(Methylsulfonyl)ethanamin zugesetzt. Der Ansatz wurde für 16 Stunden bei 50 °C gerührt und anschließend im Vakuum eingedampft. Die Aufreinigung erfolgte chromatographisch mittels MPLC. Man erhielt 57,7 mg (94,7%> Reinheit, 19,4% d. Th.) der Titelverbindung (71). 1H-NMR(400,0 MHz, de-DMSO): δ = 9,310(1,5); 8,925(0,8); 8,912(1,6); 8,899(0,8); 8,789(1,2); 8,669(3,6); 8,505(1,5); 8,485(1,5); 8,206(2,5); 8,185(3,2); 8,036(1,8); 8,032(2,0); 8,010(1,6); 7,664(1,1); 7,652(1,1); 7,645(1,1); 7,633(1,0); 3,901(12,1); 3,757(1,1); 3,741(2,6); 3,726(2,7); 3,709(1,4); 3,437(8,0); 3,419(14,7); 3,372(744,9); 3,170(1,6); 3,117(0,6); 3,063(16,0); 2,673(1,7); 2,508(210,9); 2,504(294,2); 2,500(232,0); 2,331(1,8); 1,491(0,5); 1,336(0,4); 1,297(0,3); 1,250(0,4); 1,234(0,7); 0,969(0,9); 0,954(1,1); 0,867(0,6); 0,849(1,1); 0,832(0,6); 0,000(6,2) To a solution of 200 mg (0.78 mmol, assumed purity 100%) of 2- (pyridin-3-yl) -1,3-benzothiazole-6-carboxylic acid (Ik-1) in 6 ml of dioxane was added 3 molar equivalents (eq .) Propylphosphonicanhydrid (T3P) and 5 molar equivalents (eq.) Of triethylamine. Subsequently, 115.78 mg (0.94 mmol, 1.2 eq.) Of 2- (methylsulfonyl) ethanamine was added. The batch was stirred for 16 hours at 50 ° C and then evaporated in vacuo. The purification was carried out by chromatography using MPLC. 57.7 mg (94.7% pure, 19.4% of theory) of the title compound (71) were obtained. 1 H NMR (400.0 MHz, de-DMSO): δ = 9.310 (1.5); 8,925 (0.8); 8.912 (1.6); 8,899 (0.8); 8,789 (1.2); 8,669 (3.6); 8,505 (1.5); 8,485 (1.5); 8,206 (2.5); 8.185 (3.2); 8,036 (1.8); 8,032 (2.0); 8.010 (1.6); 7.664 (1.1); 7,652 (1.1); 7,645 (1.1); 7,633 (1.0); 3,901 (12.1); 3,757 (1.1); 3,741 (2.6); 3,726 (2.7); 3,709 (1.4); 3,437 (8.0); 3,419 (14.7); 3.372 (744.9); 3,170 (1.6); 3,117 (0.6); 3,063 (16.0); 2,673 (1.7); 2,508 (210.9); 2.504 (294.2); 2,500 (232.0); 2.331 (1.8); 1.491 (0.5); 1.336 (0.4); 1,297 (0.3); 1,250 (0.4); 1,234 (0.7); 0.969 (0.9); 0.954 (1.1); 0.867 (0.6); 0.849 (1.1); 0.832 (0.6); 0.000 (6.2)
2-(5-Fluorpyridin-3-yl)-N-{3-[(trifluormethyl)sulfanyl]phenyl}-l,3-benzothiazol-6-carboxamid (74) 2- (5-Fluoropyridin-3-yl) - N - {3 - [(trifluoromethyl) sulfanyl] phenyl} -1,3-benzothiazole-6-carboxamide (74)
Zu einer Lösung von 200 mg (0,73 mmol, angenommene Reinheit 100%) 2-(5-Fluorpyridin-3-yl)-l,3- benzothiazol-6-carbonsäure (I-k-2) (hergestellt analog der Synthese zur Verbindung (I-k-1), ausgehend von 3-(Chlorcarbonyl)-5-fluorpyridiniumchlorid in Methode A, Schritt 1) in 6 ml Dioxan wurden 3 Moläquivalente (eq.) Propylphosphonicanhydrid (T3P) sowie 5 Moläquivalente (eq.) Triethylamin gegeben. Anschließend wurden 169,2 mg (0,88 mmol, 1,2 eq.) 3-[(Trifluormethyl)sulfanyl]anilin zugesetzt. Der Ansatz wurde für 16 Stunden bei 50 °C gerührt und anschließend im Vakuum eingedampft. Die Aufreinigung erfolgte chromatographisch mittels MPLC. Man erhielt 10,8 mg (99,3% Reinheit, 3,3%> d. Th.) der Titelverbindung (74). To a solution of 200 mg (0.73 mmol, assumed purity 100%) 2- (5-fluoropyridin-3-yl) -1,3-benzothiazole-6-carboxylic acid (Ik-2) (prepared analogously to the synthesis of the compound (Ik-1), starting from 3- (chlorocarbonyl) -5-fluoropyridinium chloride in method A, step 1) in 6 ml of dioxane were added 3 molar equivalents (eq.) Propylphosphonicanhydrid (T3P) and 5 molar equivalents (eq.) Of triethylamine. Subsequently, 169.2 mg (0.88 mmol, 1.2 eq.) Of 3 - [(trifluoromethyl) sulfanyl] aniline was added. The batch was stirred for 16 hours at 50 ° C and then evaporated in vacuo. The purification was carried out by chromatography using MPLC. 10.8 mg (99.3% purity, 3.3% of theory) of the title compound (74) were obtained.
1H-NMR(601,6 MHz, de-DMSO): δ = 10,720(6,1); 9,217(5,6); 9,215(8,8); 8,863(10,1); 8,860(10,0); 8,839(9,2); 8,835(9,3); 8,470(3,0); 8,467(3,7); 8,466(3,7); 8,463(2,9); 8,455(3,2); 8,451(3,9); 8,450(3,5); 8,447(2,9); 8,282(16,0); 8,268(9,9); 8,173(6,8); 8,170(6,5); 8,159(5,4); 8,156(5,4); 8,041(4,3); 8,039(4,0); 8,029(4,0); 8,027(4,4); 8,025(4,5); 8,024(3,8); 7,578(4,4); 7,565(8,8); 7,552(5,6); 7,481(5,3); 7,468(4,0); 5,756(0,9); 3,351(0,5); 3,323(315,1); 3,174(0,5); 3,165(0,5); 2,617(1,0); 2,614(1,3); 2,611(1,0); 2,523(2,5); 2,520(3,2); 2,517(3,6); 2,508(74,4); 2,505(151,5); 2,502(200,8); 2,499(148,7); 2,496(72,2); 2,389(1,0); 2,386(1,3); 2,383(0,9); 1,352(1,5); 1,231(2,2); 0,852(0,5); 0,000(5,7) 2-(5-Fluorpyridin-3-yl)-N-{3-[(trifluormethyl)sulfinyl]phenyl}-l,3-benzothiazol-6-carboxamid (75) 1 H NMR (601.6 MHz, de-DMSO): δ = 10.720 (6.1); 9,217 (5.6); 9,215 (8.8); 8.863 (10.1); 8,860 (10.0); 8,839 (9.2); 8,835 (9.3); 8,470 (3.0); 8,467 (3.7); 8,466 (3.7); 8.463 (2.9); 8.455 (3.2); 8.451 (3.9); 8,450 (3.5); 8,447 (2.9); 8.282 (16.0); 8.268 (9.9); 8,173 (6.8); 8,170 (6.5); 8.159 (5.4); 8,156 (5.4); 8.041 (4.3); 8,039 (4.0); 8,029 (4.0); 8,027 (4.4); 8,025 (4.5); 8.024 (3.8); 7,578 (4.4); 7,565 (8.8); 7,552 (5.6); 7,481 (5.3); 7,468 (4.0); 5,756 (0.9); 3,351 (0.5); 3.323 (315.1); 3,174 (0.5); 3,165 (0.5); 2,617 (1.0); 2,614 (1.3); 2,611 (1.0); 2,523 (2.5); 2,520 (3.2); 2,517 (3.6); 2,508 (74.4); 2.505 (151.5); 2.502 (200.8); 2.499 (148.7); 2,496 (72.2); 2,389 (1.0); 2,386 (1.3); 2,383 (0.9); 1,352 (1.5); 1,231 (2.2); 0.852 (0.5); 0.000 (5.7) 2- (5-fluoropyridin-3-yl) -N- {3 - [(trifluoromethyl) sulfinyl] phenyl} -1,3-benzothiazole-6-carboxamide (75)
Zu einer Lösung von 300 mg (0,67 mmol) 2-(5-Fluorpyridin-3-yl)-N- {3- [(trifluormethyl)sulfanyl]phenyl} -l,3-benzothiazol-6-carboxamid (74) in 10 ml Dichlormethan wurden 2 Moläquivalente (222,5 mg, 1,3 mmol) meta-Chlorperbenzoesäure bei 0 °C zugesetzt. Die Reaktionsmischung wurde noch für 16 Stunden bei 20 °C gerührt und anschließend im Vakuum eingedampft. Die Aufreinigung erfolgte chromatographisch mittels MPLC. Man erhielt 7,9 mg (94% Reinheit, 2,4% d. Th.) der Titelverbindung (75). To a solution of 300 mg (0.67 mmol) 2- (5-fluoropyridin-3-yl) -N- {3- [(trifluoromethyl) sulfanyl] phenyl} -1,3-benzothiazole-6-carboxamide (74) in 10 ml of dichloromethane, 2 molar equivalents (222.5 mg, 1.3 mmol) of meta-chloroperbenzoic acid were added at 0 ° C. The reaction mixture was stirred for 16 hours at 20 ° C and then evaporated in vacuo. The purification was carried out by chromatography using MPLC. This gave 7.9 mg (94% purity, 2.4% of theory) of the title compound (75).
1H-NMR(601,6 MHz, d6-DMSO): δ = 10,878(15,2); 9,218(13,9); 9,188(0,6); 8,886(16,0); 8,884(15,6).1 H NMR (601.6 MHz, d 6 -DMSO): δ = 10.878 (15.2); 9,218 (13.9); 9.188 (0.6); 8,886 (16.0); 8.884 (15.6).
8,841(14,1); 8,837(14,1); 8,825(0,8); 8,820(0,7); 8,724(0,8); 8,722(0,9); 8,474(5,0); 8,471(6,4). 8,470(6,5); 8,461(13,9); 8,459(13,6); 8,456(8,5); 8,451(4,5); 8,290(11,8); 8,276(15,9); 8,193(10,7).8,841 (14.1); 8,837 (14.1); 8,825 (0.8); 8,820 (0.7); 8,724 (0.8); 8.722 (0.9); 8.474 (5.0); 8,471 (6.4). 8,470 (6.5); 8.461 (13.9); 8.459 (13.6); 8.456 (8.5); 8.451 (4.5); 8,290 (11.8); 8.276 (15.9); 8,193 (10.7).
8,190(10,4); 8,178(11,5); 8,176(14,8); 8,162(6,9); 8,160(6,9); 8,085(0,5); 8,082(0,5); 8,071(0,4).8,190 (10.4); 8.178 (11.5); 8,176 (14.8); 8.162 (6.9); 8,160 (6.9); 8,085 (0.5); 8,082 (0.5); 8,071 (0.4).
8,068(0,4); 7,745(6,9); 7,732(14,0); 7,719(8,3); 7,627(8,2); 7,614(6,4); 7,494(0,3); 7,482(0,7).8,068 (0.4); 7,745 (6.9); 7,732 (14.0); 7,719 (8.3); 7.627 (8.2); 7,614 (6.4); 7,494 (0.3); 7,482 (0.7).
5,756(2,4); 3,322(541,8); 3,173(1,1); 3,165(1,1); 2,617(2,8); 2,614(3,8); 2,611(2,8); 2,541(1,2).5,756 (2.4); 3.322 (541.8); 3,173 (1.1); 3,165 (1.1); 2,617 (2.8); 2,614 (3.8); 2,611 (2.8); 2,541 (1.2).
2,523(7,5); 2,520(9,5); 2,517(10,4); 2,508(219,2); 2,505(439,2); 2,502(581,7); 2,499(428,1). 2,496(208,9); 2,389(2,5); 2,386(3,4); 2,383(2,5); 1,904(1,9); 1,233(1,6); 0,853(0,3); 0,005(0,6).2,523 (7.5); 2,520 (9.5); 2,517 (10.4); 2,508 (219.2); 2.505 (439.2); 2.502 (581.7); 2.499 (428.1). 2.496 (208.9); 2,389 (2.5); 2,386 (3.4); 2,383 (2.5); 1,904 (1.9); 1,233 (1.6); 0.853 (0.3); 0.005 (0.6).
0,000(15,5); -0,006(0,6) 0,000 (15.5); -0.006 (0.6)
Synthese von Verbindungen der Formel (I) nach Methode H Synthesis of compounds of the formula (I) by Method H
2-(Pyridin-3-yl)-l,3-benzothiazol-6-amin (I-s-1) 2- (pyridin-3-yl) -l, 3-benzothiazol-6-amine (I-s-1)
Zu einer gerührten Lösung von 9,0 g (35 mmol) 6-Nitro-2-(pyridin-3-yl)-l,3-benzothiazol (I-r-1) (hergestellt analog der Synthese zur Verbindung (I-a-2), im Unterschied ausgehend von 2-Brom-4- nitroanilin in Methode A, Schritt 1) in 350 ml THF wurden bei 30 °C unter Stickstoff 1,8 g Pd/C (10 wt%>) gegeben. Die Mischung wurde bei 50 °C unter Wasserstoff (50 psi) für 48 Stunden gerührt. Anschließend wurde die Reaktionsmischung filtriert und das Filtrat im Vakuum eingedampft. Man erhielt 6,1 g 2-(Pyridin-3-yl)-l,3-benzothiazol-6-amin (I-s-1) als Rohprodukt, das ohne weitere Aufreinigung weiter zu Amiden umgesetzt wurde. Hierfür wurde eine Reinheit von 100% angenommen. To a stirred solution of 9.0 g (35 mmol) of 6-nitro-2- (pyridin-3-yl) -1,3-benzothiazole (Ir-1) (prepared analogously to the synthesis of the compound (Ia-2), in contrast, starting from 2-bromo-4-nitroaniline in Method A, step 1) in 350 ml of THF at 30 ° C under nitrogen, 1.8 g Pd / C (10 wt%>). The mixture was stirred at 50 ° C under hydrogen (50 psi) for 48 hours. Then the reaction mixture was filtered and the filtrate evaporated in vacuo. This gave 6.1 g of 2- (pyridin-3-yl) -1,3-benzothiazol-6-amine (Is-1) as a crude product, which was reacted further without further purification to amides. For this purpose, a purity of 100% was assumed.
LC-MS: m/z 228 [M+H+] 2-(5-Fluorpyridin-3-yl)-l,3-benzothiazol-6-amin (I-s-2) LC-MS: m / z 228 [M + H + ] 2- (5-fluoropyridin-3-yl) -1,3-benzothiazol-6-amine (Is-2)
Die Herstellung erfolgte in Analogie zur Synthese von (I-s-1), im Unterschied ausgehend von 3- (Chlorcarbonyl)-5-fluorpyridiniumchlorid in Methode A, Schritt 1. The preparation was carried out in analogy to the synthesis of (I-s-1), in contrast starting from 3- (chlorocarbonyl) -5-fluoropyridinium chloride in method A, step 1.
LC-MS: m/z 246 [M+H+] N-Methyl-N-[2-(pyridin-3-yl)-l,3-benzothiazol-6-yl]propanamid (76) LC-MS: m / z 246 [M + H + ] N -methyl-N- [2- (pyridin-3-yl) -l, 3-benzothiazol-6-yl] -propanamide (76)
Schritt 1: N-[2-(Pyridin-3-yl)-l,3-benzothiazol-6-yl]propanamid Step 1: N- [2- (Pyridin-3-yl) -1,3-benzothiazol-6-yl] propanamide
Zu einer Mischung von 300 mg (1,31 mmol, angenommene Reinheit 100%) 2-(Pyridin-3-yl)-l,3- benzothiazol-6-amin (I-s-1) und 398 mg (3,93 mmol) Triethylamin in 5 ml Dichlormethan wurden 121,6 mg (1,31 mmol) Propanoylchlorid gegeben. Der Ansatz wurde für 16 Stunden bei 30 °C gerührt und anschließend im Vakuum eingedampft. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittelgradient Petrolether/Ethylacetat). Man erhielt 300 mg N-[2-(Pyridin-3-yl)-l,3-benzothiazol- 6-yl]propanamid, das direkt weiter umgesetzt wurden. Hierfür wurde eine Reinheit von 100%) angenommen. To a mixture of 300 mg (1.31 mmol, assumed purity 100%) of 2- (pyridin-3-yl) -l, 3-benzothiazol-6-amine (Is-1) and 398 mg (3.93 mmol) Triethylamine in 5 ml of dichloromethane was added 121.6 mg (1.31 mmol) of propanoyl chloride. The batch was stirred for 16 hours at 30 ° C and then evaporated in vacuo. The purification was carried out by chromatography using MPLC (eluant gradient petroleum ether / ethyl acetate). 300 mg of N- [2- (pyridin-3-yl) -1,3-benzothiazol-6-yl] propanamide were obtained, which were reacted further directly. For this a purity of 100%) was assumed.
Schritt 2: N-Methyl-N-[2-(pyridin-3-yl)-l,3-benzothiazol-6-yl]propanamid (76) Step 2: N-Methyl-N- [2- (pyridin-3-yl) -l, 3-benzothiazol-6-yl] -propanamide (76)
172 mg (0,605 mmol, angenommene Reinheit 100%) N-[2-(Pyridin-3-yl)-l,3-benzothiazol-6- yl]propanamid aus Schritt 1 wurden in 5 ml THF gelöst und auf 0 °C abgekühlt. Anschließend wurden 24,2 mg (0,605 mmol) Natriumhydrid (60%ige Suspension in Paraffin) bei 0 °C zugesetzt. Die Mischung wurde bei dieser Temperatur noch 30 Minuten gerührt und dann 85,9 mg (0,605 mmol) Methyliodid zugegeben. Der Ansatz wurde bei 30 °C noch 16 Stunden gerührt und dann bei 0 °C mit 1 ml wässriger Ammoniumchloridlösung versetzt. Nach Eindampfen der Mischung im Vakuum wurde der Rückstand chromatographisch mittels präparativer HPLC gereinigt. Man erhielt 12 mg (97,3% Reinheit, 6,5%o d. Th.) der Titelverbindung (76). 1H-NMR(400,0 MHz, de-DMSO): δ = 10,209(0,4); 9,289(2,9); 8,787(2,0); 8,777(2,0); 8,586(0,4);172 mg (0.605 mmol, assumed purity 100%) of N- [2- (pyridin-3-yl) -l, 3-benzothiazol-6-yl] propanamide from step 1 were dissolved in 5 ml THF and cooled to 0 ° C , Subsequently, 24.2 mg (0.605 mmol) of sodium hydride (60% suspension in paraffin) was added at 0 ° C. The mixture was stirred at this temperature for a further 30 minutes and then 85.9 mg (0.605 mmol) of methyl iodide were added. The mixture was stirred at 30 ° C for 16 hours and then treated at 0 ° C with 1 ml of aqueous ammonium chloride solution. After evaporation of the mixture in vacuo, the residue was purified by chromatography on preparative HPLC. 12 mg (97.3% purity, 6.5% of theory) of the title compound (76) were obtained. 1 H NMR (400.0 MHz, de-DMSO): δ = 10.209 (0.4); 9.289 (2.9); 8,787 (2.0); 8.777 (2.0); 8,586 (0.4);
8,581(0,4); 8,485(1,7); 8,480(2,5); 8,475(1,8); 8,465(1,9); 8,460(2,6); 8,455(1,7); 8,223(3,0); 8,163(3,3);8,581 (0.4); 8,485 (1.7); 8,480 (2.5); 8,475 (1.8); 8,465 (1.9); 8,460 (2.6); 8.455 (1.7); 8,223 (3.0); 8.163 (3.3);
8,141(3,5); 8,040(0,5); 8,018(0,6); 7,655(2,0); 7,644(2,1); 7,636(2,1); 7,623(2,2); 7,606(0,5); 7,601(0,3);8,141 (3.5); 8,040 (0.5); 8,018 (0.6); 7.655 (2.0); 7.644 (2.1); 7,636 (2.1); 7,623 (2.2); 7,606 (0.5); 7,601 (0.3);
7,551(2,5); 7,546(2,5); 7,530(2,3); 7,525(2,3); 3,902(16,0); 3,510(0,6); 3,343(457,5); 3,247(7,7);7,551 (2.5); 7,546 (2.5); 7,530 (2.3); 7,525 (2.3); 3,902 (16.0); 3,510 (0.6); 3.343 (457.5); 3,247 (7.7);
3,173(0,7); 3,167(0,7); 2,682(0,5); 2,678(1,0); 2,673(1,3); 2,668(1,0); 2,664(0,5); 2,526(3,4); 2,513(76,7); 2,508(162,9); 2,504(229,3); 2,499(170,8); 2,495(81,3); 2,398(0,7); 2,379(0,7); 2,340(0,5);3,173 (0.7); 3,167 (0.7); 2,682 (0.5); 2,678 (1.0); 2,673 (1.3); 2,668 (1.0); 2,664 (0.5); 2,526 (3.4); 2,513 (76.7); 2,508 (162.9); 2.504 (229.3); 2.499 (170.8); 2,495 (81.3); 2,398 (0.7); 2,379 (0.7); 2,340 (0.5);
2,335(0,9); 2,331(1,3); 2,326(0,9); 2,100(0,9); 1,259(0,4); 1,234(0,5); 1,139(0,8); 1,120(1,6); 1,101(0,7);2,335 (0.9); 2.331 (1.3); 2,326 (0.9); 2,100 (0.9); 1,259 (0.4); 1,234 (0.5); 1,139 (0.8); 1,120 (1.6); 1,101 (0.7);
0,963(3,2); 0,944(5,7); 0,926(2,9); 0,000(7,6) 0.963 (3.2); 0.944 (5.7); 0.926 (2.9); 0.000 (7.6)
N-[2-(5-Fluorpyridin-3-yl)-l,3-benzothiazol-6-yl]-N-methyl-3-[(trifluormethyl)sulfanyl]-benzamid (85) N- [2- (5-fluoropyridin-3-yl) -1,3-benzothiazol-6-yl] -N-methyl-3 - [(trifluoromethyl) sulfanyl] benzamide (85)
Schritt 1: N-[2-(5-Fluorpyridin-3-yl)-l,3-benzothiazol-6-yl]-3-[(trifluormethyl)sulfanyl]-benzamid Step 1: N- [2- (5-Fluoropyridin-3-yl) -1,3-benzothiazol-6-yl] -3 - [(trifluoromethyl) sulfanyl] benzamide
Zu einer Mischung von 500 mg (2,04 mmol) 2-(5-Fluorpyridin-3-yl)-l,3-benzothiazol-6-amin (I-s-2) (hergestellt analog der Synthese zur Verbindung (I-s-1), ausgehend von 3-(Chlorcarbonyl)-5- fluorpyridiniumchlorid in Methode A, Schritt 1) und 543 mg (2,45 mmol) Triethylamin in Dichlormethan wurden 747 mg (6,12 mmol) DMAP und 586 mg (3,06 mmol) EDCI gegeben. Der Ansatz wurde für 16 Stunden bei 30 °C gerührt und anschließend im Vakuum eingedampft. Die Reinigung erfolgte chromatographisch mittels MPLC (Fließmittelgradient Petrolether/Ethylacetat). Man erhielt 500 mg N-[2-(5-Fluo^yridin-3-yl)-l,3-benzothiazol-6-yl]-3-[(trifluormethyl)sulfanyl]-benzamid, das direkt weiter umgesetzt wurden. Hierfür wurde eine Reinheit von 100% angenommen. To a mixture of 500 mg (2.04 mmol) of 2- (5-fluoropyridin-3-yl) -1,3-benzothiazol-6-amine (Is-2) (prepared analogously to the synthesis of the compound (Is-1) starting from 3- (chlorocarbonyl) -5- fluoropyridinium chloride in Method A, step 1) and 543 mg (2.45 mmol) of triethylamine in dichloromethane were added 747 mg (6.12 mmol) of DMAP and 586 mg (3.06 mmol) EDCI. The batch was stirred for 16 hours at 30 ° C and then evaporated in vacuo. The purification was carried out by chromatography using MPLC (eluant gradient petroleum ether / ethyl acetate). 500 mg of N- [2- (5-fluoro-3-yl-yl) -l, 3-benzothiazol-6-yl] -3 - [(trifluoromethyl) -sulfanyl] -benzamide were obtained, which were reacted further directly. For this purpose, a purity of 100% was assumed.
Schritt 2: N-[2-(5-Fluorpyridin-3-yl)-l,3-benzothiazol-6-yl]-N-methyl-3-[(trifluormethyl)- sulfanyl]-benzamid (85) Step 2: N- [2- (5-Fluoropyridin-3-yl) -l, 3-benzothiazol-6-yl] -N-methyl-3 - [(trifluoromethyl) -sulfanyl] -benzamide (85)
272 mg (0,605 mmol) N-[2-(5-Fluorpyridin-3-yl)-l,3-benzothiazol-6-yl]-3-[(trifluormethyl)- sulfanyljbenzamid (Beispiel 85, Schritt 1) wurden in 5 ml THF gelöst und auf 0 °C abgekühlt. Anschließend wurden 24,2 mg (0,605 mmol) Natriumhydrid (60%ige Suspension in Paraffin) bei 0 °C zugesetzt. Die Mischung wurde bei dieser Temperatur noch 30 Minuten gerührt und dann 85,9 mg (0,605 mmol) Methyliodid zugegeben. Der Ansatz wurde bei 30 °C noch 16 Stunden gerührt und dann bei 0 °C mit 1 ml wässriger Ammoniumchloridlösung versetzt. Nach Eindampfen der Mischung im Vakuum wurde der Rückstand chromatographisch mittels präparativer HPLC gereinigt. Man erhielt 92,2 mg (97,4% Reinheit, 32,0% d. Th.) der Titelverbindung (85). 272 mg (0.605 mmol) of N- [2- (5-fluoropyridin-3-yl) -l, 3-benzothiazol-6-yl] -3 - [(trifluoromethyl) sulfanyl] benzamide (Example 85, Step 1) were prepared in 5 dissolved in THF and cooled to 0 ° C. Subsequently, 24.2 mg (0.605 mmol) of sodium hydride (60% suspension in paraffin) was added at 0 ° C. The mixture was stirred at this temperature for a further 30 minutes and then 85.9 mg (0.605 mmol) of methyl iodide were added. The mixture was stirred at 30 ° C for 16 hours and then treated at 0 ° C with 1 ml of aqueous ammonium chloride solution. After evaporation of the mixture in vacuo, the residue was purified by chromatography on preparative HPLC. 92.2 mg (97.4% purity, 32.0% of theory) of the title compound (85) were obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 9,117(2,8); 9,113(4,5); 9,109(3,3); 8,787(4,0); 8,781(4,4); 8,373(1,4); 8,366(1,9); 8,361(1,7); 8,349(1,7); 8,345(1,9); 8,338(1,6); 8,128(3,5); 8,123(3,9); 8,004(3,1); 7,983(3,5); 7,604(2,1); 7,585(4,6); 7,575(5,7); 7,469(1,9); 7,464(2,2); 7,447(2,4); 7,442(3,6); 7,422(2,5); 7,403(1,2); 3,902(16,0); 3,473(20,2); 3,330(581,9); 3,169(0,8); 2,676(1,1); 2,671(1,5); 2,667(1,3); 2,511(104,1); 2,507(192,5); 2,502(260,0); 2,498(220,1); 2,493(137,4); 2,333(1,1); 2,329(1,5); 2,324(1,2); 1,258(0,4); 1,235(0,4); -0,001(10,7) 1 H NMR (400.0 MHz, de-DMSO): δ = 9.117 (2.8); 9.113 (4.5); 9,109 (3.3); 8,787 (4.0); 8.781 (4.4); 8.373 (1.4); 8,366 (1.9); 8,361 (1.7); 8,349 (1.7); 8.345 (1.9); 8,338 (1.6); 8.128 (3.5); 8.123 (3.9); 8,004 (3.1); 7,983 (3.5); 7,604 (2.1); 7,585 (4.6); 7,575 (5.7); 7.469 (1.9); 7,464 (2.2); 7,447 (2.4); 7.442 (3.6); 7,422 (2.5); 7,403 (1.2); 3,902 (16.0); 3,473 (20.2); 3.330 (581.9); 3,169 (0.8); 2,676 (1.1); 2,671 (1.5); 2,667 (1.3); 2,511 (104.1); 2.507 (192.5); 2.502 (260.0); 2.498 (220.1); 2,493 (137.4); 2,333 (1.1); 2,329 (1.5); 2,324 (1.2); 1,258 (0.4); 1,235 (0.4); -0.001 (10.7)
N-[2-(5-Fluorpyridin-3-yl)-l,3-benzothiazol-6-yl]-3-[(trifluormethyl)sulfinyl]benzamid (87) N- [2- (5-fluoropyridin-3-yl) -1,3-benzothiazol-6-yl] -3 - [(trifluoromethyl) sulfinyl] benzamide (87)
Zu einer Lösung von 400 mg (0,86 mmol) N-[2-(5-Fluorpyridin-3-yl)-l,3-benzothiazol-6-yl]-3- [(trifluormethyl)sulfanyl]-benzamid (Beispiel 85, Schritt 1) in 5 ml Dichlormethan wurden 2 Moläquivalente (296,8 mg, 1,72 mmol) meta-Chlorperbenzoesäure bei 0 °C zugesetzt. Die Reaktionsmischung wurde noch für 16 Stunden bei 25 °C gerührt und anschließend im Vakuum eingedampft. Die Reinigung erfolgte chromatographisch mittels präparativer HPLC. Man erhielt 16 mg (99,9% Reinheit, 39,9% d. Th.) der Titelverbindung (87). To a solution of 400 mg (0.86 mmol) of N- [2- (5-fluoropyridin-3-yl) -1,3-benzothiazol-6-yl] -3- [(trifluoromethyl) sulfanyl] benzamide (Example 85, Step 1) in 5 ml of dichloromethane was added 2 molar equivalents (296.8 mg, 1.72 mmol) of meta-chloroperbenzoic acid at 0 ° C. The reaction mixture was stirred for 16 hours at 25 ° C and then evaporated in vacuo. The purification was carried out by chromatography using preparative HPLC. 16 mg (99.9% purity, 39.9% of theory) of the title compound (87) were obtained.
1H-NMR(400,0 MHz, de-DMSO): δ = 10,872(5,4); 9,144(5,1); 8,790(4,5); 8,784(4,7); 8,742(4,7); 8,737(4,9); 8,480(4,4); 8,400(2,5); 8,392(2,1); 8,385(3,5); 8,381(4,2); 8,368(1,8); 8,364(2,1); 8,357(1,6); 8,155(4,7); 8,145(2,3); 8,133(6,0); 7,949(2,7); 7,929(4,7); 7,910(2,2); 7,900(3,0); 7,895(2,9); 7,878(2,5); 7,873(2,6); 3,902(16,0); 3,508(0,5); 3,347(608,9); 3,344(633,8); 3,176(1,4); 3,163(1,4); 2,677(1,2); 2,673(1,6); 2,668(1,2); 2,543(1,4); 2,526(4,5); 2,512(97,0); 2,508(204,5); 2,503(286,3); 2,499(216,7); 2,495(106,2); 2,335(1,2); 2,330(1,6); 2,326(1,2); 1,249(0,3); 1,235(0,5); 0,008(0,3); 0,000(9,6) 1 H NMR (400.0 MHz, de-DMSO): δ = 10.872 (5.4); 9.144 (5.1); 8,790 (4.5); 8.784 (4.7); 8,742 (4.7); 8,737 (4.9); 8,480 (4.4); 8,400 (2.5); 8,392 (2.1); 8,385 (3.5); 8,381 (4.2); 8,368 (1.8); 8,364 (2.1); 8,357 (1.6); 8.155 (4.7); 8.145 (2.3); 8,133 (6.0); 7,949 (2.7); 7.929 (4.7); 7.910 (2.2); 7,900 (3.0); 7.895 (2.9); 7,878 (2.5); 7,873 (2.6); 3,902 (16.0); 3,508 (0.5); 3.347 (608.9); 3,344 (633.8); 3,176 (1.4); 3,163 (1.4); 2,677 (1.2); 2,673 (1.6); 2,668 (1.2); 2,543 (1.4); 2,526 (4.5); 2,512 (97.0); 2,508 (204.5); 2.503 (286.3); 2.499 (216.7); 2.495 (106.2); 2,335 (1.2); 2,330 (1.6); 2,326 (1.2); 1,249 (0.3); 1,235 (0.5); 0.008 (0.3); 0.000 (9.6)
Weitere Verbindungen der Formel (I) und auch solche, die nicht unter die Formel (I) fallen, sind in der folgenden Tabelle aufgeführt. Auch die nicht unter die Formel (I) fallenden Verbindungen sind Gegenstand der Erfindung. Further compounds of the formula (I) and also those which do not fall under the formula (I) are listed in the following table. Also not falling under the formula (I) compounds are the subject of the invention.
Tabelle 1 Table 1
Verbindung en der Formel (I) Compounds of the formula (I)
Herstell¬Herstell¬
Beispiel-Nr. A 1 R2 Example no. A 1 R 2
methode Q R -214- method QR -214-
-215 - -215 -
-216- -216-
Herstell¬ Herstell¬
Beispiel-Nr. A Example no. A
methode Q R1 R2 method QR 1 R 2
F 43 s H F 43 s H
o \ o \
/ /
F 44 s H F 44 s H
E 45 s H E 45 s H
S S
E 46 s H  E 46 s H
\ 0\ 0
E 47 s H 0E 47 s H 0
00
E 48 s H E 48 s H
S S
E 49 s H  E 49 s H
E 50 s HE 50 s H
-221 - -221 -
Tabelle 2 Table 2
Analytische Daten zu den angegebenen Verbindungen Analytical data for the specified compounds
Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,306 (9,5); 9,301 (9,7); 8,781 (7,0); 8,778 (7,5); 8,769 (7,3); 8,766 (7,2); 8,541 (12,8); 8,537 (13,0); 8,502 (4,0); 8,497 (5,8); 8,492 (4,0); 8,482 (4,3); 8,477 (6,0); 8,472 (4,0); 8,318 (0,5); 8,197 (10,9); 8,175 (12,5); 7,910 (7,8); 7,905 (7,8); 7,888 (6,7); 7,884 (6,8); δ = 9.306 (9.5); 9,301 (9.7); 8,781 (7.0); 8,778 (7.5); 8,769 (7.3); 8,766 (7.2); 8,541 (12.8); 8,537 (13.0); 8,502 (4.0); 8.497 (5.8); 8.492 (4.0); 8,482 (4,3); 8.477 (6.0); 8.472 (4.0); 8.318 (0.5); 8,197 (10.9); 8,175 (12.5); 7.910 (7.8); 7.905 (7.8); 7,888 (6.7); 7,884 (6.8);
1 3,7 3,87 7,811 (13,7); 7,793 (15,2); 7,655 (5,5); 7,643 (5,4); 1 3.7 3.87 7.811 (13.7); 7,793 (15,2); 7.655 (5.5); 7,643 (5.4);
7,635 (5,3); 7,623 (5,2); 7,544 (7,6); 7,525 (16,0); 7,506 (9,8); 7,439 (5,6); 7,421 (8,0); 7,402 (2,8); 5,759 (1,2); 3,804 (0,9); 3,333 (260,8); 2,672 (1,7); 2,668 (1,3); 2,508 (196,0); 2,503 (254,4); 2,499 (191,5); 2,334 (1,2); 2,330 (1,6); 2,326 (1,2); 1,230 (0,6); 0,146 (0,6); 0,008 (4,7); 0,000 (138,6); -0,150 (0,6)  7,635 (5.3); 7.623 (5.2); 7,544 (7.6); 7,525 (16.0); 7.506 (9.8); 7.439 (5.6); 7,421 (8.0); 7,402 (2,8); 5,759 (1.2); 3,804 (0.9); 3.333 (260.8); 2,672 (1.7); 2,668 (1.3); 2,508 (196.0); 2,503 (254.4); 2,499 (191.5); 2.334 (1.2); 2,330 (1.6); 2,326 (1.2); 1,230 (0.6); 0.146 (0.6); 0.008 (4.7); 0,000 (138.6); -0.150 (0.6)
'H-NMR (400,0 MHz, de-DMSO):□  'H-NMR (400.0 MHz, de-DMSO): □
δ = 9,303 (2,3); 9,298 (2,3); 8,783 (1,7); 8,780 (1,8); 8,771 (1,8); 8,768 (1,8); 8,500 (1,0); 8,495 (1,4); 8,490 (1,0); 8,480 (1,1); 8,475 (1,5); 8,470 (1,0); 8,199 (3,2); δ = 9.303 (2.3); 9,298 (2,3); 8,783 (1.7); 8,780 (1.8); 8.771 (1.8); 8,768 (1.8); 8,500 (1.0); 8.495 (1.4); 8,490 (1.0); 8.480 (1.1); 8.475 (1.5); 8.470 (1.0); 8,199 (3.2);
2 4,08 4,24 8,195 (3,2); 8,169 (2,9); 8,148 (3,1); 7,657 (1,3); 7,645 2 4.08 4.24 8.195 (3.2); 8,169 (2,9); 8,148 (3,1); 7.657 (1.3); 7,645
(1,4); 7,637 (1,3); 7,625 (1,4); 7,564 (2,1); 7,560 (2,1); 7,543 (1,9); 7,539 (1,9); 7,366 (0,3); 7,356 (0,8); 7,346 (2,7); 7,336 (1,7); 7,324 (2,7); 7,313 (5,7); 7,308 (6,0); 3,333 (41,6); 2,509 (33,4); 2,504 (42,8); 2,500 (31,4); 2,289 (16,0); 0,008 (0,6); 0,000 (14,0); -0,008 (0,5) (1.4); 7.637 (1.3); 7.625 (1.4); 7,564 (2.1); 7,560 (2.1); 7,543 (1.9); 7,539 (1.9); 7.366 (0.3); 7.356 (0.8); 7,346 (2.7); 7.336 (1.7); 7,324 (2.7); 7,313 (5.7); 7,308 (6.0); 3,333 (41.6); 2,509 (33.4); 2,504 (42.8); 2,500 (31.4); 2,289 (16,0); 0.008 (0.6); 0.000 (14.0); -0.008 (0.5)
'H-NMR (400,0 MHz, de-DMSO): 'H-NMR (400.0 MHz, de-DMSO):
3 4,27 4,41 δ = 9,302 (2,8); 9,297 (2,9); 8,779 (2,0); 8,775 (2,3);  3 4.27 4.41 δ = 9.302 (2.8); 9,297 (2.9); 8,779 (2.0); 8.775 (2.3);
8,767 (2,2); 8,763 (2,3); 8,521 (3,7); 8,517 (4,0); 8,498 Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 8,767 (2,2); 8.763 (2.3); 8,521 (3.7); 8,517 (4.0); 8,498 Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
(1,2); 8,494 (1,7); 8,489 (1,3); 8,478 (1,3); 8,473 (1,8); 8,469 (1,3); 8,183 (3,3); 8,161 (3,8); 7,894 (2,3); 7,889 (2,4); 7,872 (2,0); 7,868 (2,1); 7,652 (1,6); 7,640 (1,7); 7,631 (2,4); 7,622 (4,1); 7,594 (1,6); 7,575 (1,9); 7,422 (1,7); 7,403 (3,2); 7,384 (1,7); 7,243 (2,0); 7,224 (1,6); 3,332 (108,8); 2,677 (0,5); 2,672 (0,6); 2,668 (0,5); 2,525 (1,6); 2,508 (71,1); 2,503 (95,3); 2,499 (72,6); 2,413 (16,0); 2,334 (0,4); 2,330 (0,6); 2,325 (0,5); 0,008 (1,7); 0,000 (53,6); -0,008 (2,5)  (1,2); 8.494 (1.7); 8.489 (1.3); 8.478 (1.3); 8.473 (1.8); 8.469 (1.3); 8,183 (3,3); 8,161 (3,8); 7.894 (2.3); 7,889 (2,4); 7,872 (2.0); 7,868 (2,1); 7.652 (1.6); 7.640 (1.7); 7.631 (2.4); 7,622 (4,1); 7,594 (1.6); 7,575 (1.9); 7.422 (1.7); 7,403 (3,2); 7,384 (1.7); 7.243 (2.0); 7.224 (1.6); 3,332 (108.8); 2,677 (0.5); 2,672 (0.6); 2,668 (0.5); 2,525 (1.6); 2,508 (71.1); 2,503 (95.3); 2,499 (72.6); 2,413 (16.0); 2.334 (0.4); 2,330 (0.6); 2.325 (0.5); 0.008 (1.7); 0,000 (53.6); -0.008 (2.5)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,293 (3,5); 8,774 (2,7); 8,763 (2,9); 8,501 (4,9); 8,488 (2,7); 8,467 (2,3); 8,170 (3,1); 8,149 (3,7); 7,881 (2,6); 7,879 (2,6); 7,859 (2,3); 7,858 (2,3); 7,705 (5,2); δ = 9,293 (3.5); 8,774 (2.7); 8,763 (2.9); 8,501 (4.9); 8,488 (2,7); 8.467 (2.3); 8,170 (3,1); 8.149 (3.7); 7.881 (2.6); 7.879 (2.6); 7.859 (2.3); 7.888 (2.3); 7,705 (5.2);
4 4,25 4,43 7,685 (6,0); 7,649 (2,1); 7,637 (2,3); 7,629 (2,6); 7,617 4 4.25 4.43 7.685 (6.0); 7,649 (2.1); 7.637 (2.3); 7.629 (2.6); 7,617
(2,3); 7,599 (0,6); 7,575 (0,4); 7,568 (0,4); 7,560 (0,4); 7,551 (0,4); 7,336 (5,4); 7,316 (5,1); 3,335 (56,3); 2,674 (0,4); 2,504 (58,4); 2,373 (16,0); 2,331 (0,5); 0,000 (11,2); -0,001 (11,2)  (2,3); 7,599 (0.6); 7,575 (0.4); 7,568 (0.4); 7,560 (0.4); 7,551 (0.4); 7,336 (5.4); 7,316 (5.1); 3,335 (56.3); 2,674 (0.4); 2,504 (58.4); 2.373 (16.0); 2.331 (0.5); 0.000 (11.2); -0.001 (11.2)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,313 (12,2); 9,307 (12,7); 8,788 (9,1); 8,784 (9,7); 8,776 (9,7); 8,772 (9,5); 8,510 (5,3); 8,505 (7,7); 8,500 (5,4); 8,490 (5,7); 8,485 (8,0); 8,480 (5,3); 8,420 (16,0); 8,318 (0,8); 8,215 (14,4); 8,194 (15,8); 7,776 (5,6); 7,772 (9,5); 7,768 (5,7); 7,755 (5,2); 7,751 (8,7); 7,747 δ = 9.313 (12.2); 9,307 (12,7); 8,788 (9.1); 8,784 (9.7); 8,776 (9.7); 8,772 (9.5); 8,510 (5.3); 8,505 (7.7); 8,500 (5.4); 8,490 (5.7); 8.485 (8.0); 8,480 (5.3); 8,420 (16.0); 8,318 (0.8); 8,215 (14.4); 8,194 (15,8); 7,776 (5.6); 7,772 (9.5); 7,768 (5.7); 7,755 (5.2); 7,751 (8.7); 7.747
(5.0) ; 7,680 (4,0); 7,676 (4,5); 7,660 (14,9); 7,648 (8,5);(5.0); 7,680 (4.0); 7.676 (4.5); 7,660 (14.9); 7,648 (8.5);
5 3,7 3,78 7,640 (11,5); 7,628 (7,1); 7,512 (1,7); 7,508 (1,8); 7,499 5 3.7 3.78 7.640 (11.5); 7,628 (7.1); 7,512 (1.7); 7.508 (1.8); 7,499
(2.1) ; 7,494 (4,4); 7,491 (4,5); 7,479 (4,5); 7,473 (5,5); 7,469 (3,6); 7,460 (3,3); 7,456 (3,0); 7,402 (6,5); 7,380 (11,9); 7,376 (8,6); 7,363 (11,2); 7,356 (5,4); 7,345 (4,8); 7,342 (4,1); 3,335 (446,1); 2,677 (1,6); 2,673 (2,1); 2,669 (1,6); 2,508 (246,6); 2,504 (317,7); 2,500 (239,6); 2,335 (1,6); 2,331 (2,1); 2,326 (1,7); 1,990 (1,1); 1,232 (0,6); 1,194 (0,4); 1,176 (0,6); 1,158 (0,3); 0,008 (0,5); 0,000 (12,2)  (2.1); 7,494 (4,4); 7,491 (4,5); 7,479 (4,5); 7,473 (5.5); 7.469 (3.6); 7,460 (3.3); 7.456 (3.0); 7,402 (6.5); 7,380 (11.9); 7,376 (8,6); 7,363 (11,2); 7,356 (5.4); 7,345 (4,8); 7,342 (4,1); 3,335 (446.1); 2,677 (1.6); 2,673 (2.1); 2,669 (1.6); 2,508 (246,6); 2,504 (317.7); 2,500 (239.6); 2.335 (1.6); 2.331 (2.1); 2,326 (1.7); 1,990 (1.1); 1,232 (0.6); 1,194 (0.4); 1.176 (0.6); 1.158 (0.3); 0.008 (0.5); 0,000 (12.2)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,311 (10,0); 9,306 (10,1); 8,790 (7,5); 8,786 (8,2); 8,778 (7,9); 8,774 (8,0); 8,510 (4,4); 8,506 (6,3); 8,501 (4,4); 8,490 (4,6); 8,486 (6,5); 8,481 (4,5); 8,318 (1,6); 8,299 (13,3); 8,295 (13,7); 8,200 (12,4); 8,178 (13,5); 7,989 (0,3); 7,985 (0,3); 7,661 (6,1); 7,651 (14,0); 7,647 (12,2); 7,640 (10,8); 7,635 (5,8); 7,630 (16,0); 7,626 (11,4); 7,616 (8,4); 7,606 (0,9); 7,596 (0,3); 7,550 (4,4); δ = 9.311 (10.0); 9,306 (10.1); 8,790 (7.5); 8,786 (8,2); 8,778 (7.9); 8,774 (8.0); 8,510 (4.4); 8.506 (6.3); 8,501 (4.4); 8,490 (4,6); 8,486 (6.5); 8,481 (4,5); 8.318 (1.6); 8,299 (13.3); 8.295 (13.7); 8,200 (12.4); 8,178 (13.5); 7.989 (0.3); 7.985 (0.3); 7,661 (6,1); 7.651 (14.0); 7,647 (12.2); 7.640 (10.8); 7.635 (5.8); 7,630 (16.0); 7.626 (11.4); 7.616 (8.4); 7.606 (0.9); 7,596 (0.3); 7,550 (4.4);
6 4,05 4,2 7,543 (4,9); 7,535 (4,7); 7,531 (5,9); 7,526 (9,9); 7,517 6 4.05 4.2 7.543 (4.9); 7,535 (4,7); 7,531 (5.9); 7,526 (9.9); 7,517
(1,1); 7,506 (2,0); 7,501 (3,6); 7,488 (9,2); 7,482 (12,9); 7,473 (12,7); 7,464 (8,8); 7,458 (5,7); 7,445 (1,8); 7,439 (1,3); 7,060 (0,5); 7,038 (0,4); 3,804 (1,9); 3,329 (753,6); 2,676 (4,4); 2,672 (5,9); 2,667 (4,5); 2,525 (14,8); 2,511 (338,3); 2,507 (679,2); 2,502 (892,6); 2,498 (662,1); 2,437 (0,5); 2,433 (0,5); 2,334 (4,1); 2,329 (5,7); 2,325 (4,3); 1,259 (0,4); 1,232 (1,4); 1,178 (0,3); 0,146 (2,3); 0,008 (17,7); 0,000 (523,5); -0,008 Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] (1,1); 7.506 (2.0); 7,501 (3.6); 7,488 (9,2); 7,482 (12,9); 7,473 (12,7); 7,464 (8,8); 7.458 (5.7); 7.455 (1.8); 7.439 (1.3); 7.060 (0.5); 7.038 (0.4); 3,804 (1.9); 3,329 (753.6); 2,676 (4.4); 2,672 (5.9); 2,667 (4,5); 2,525 (14.8); 2,511 (338,3); 2,507 (679.2); 2,502 (892.6); 2,498 (662.1); 2,437 (0.5); 2,433 (0.5); 2,334 (4,1); 2,329 (5.7); 2.325 (4.3); 1,259 (0.4); 1,232 (1.4); 1.178 (0.3); 0.146 (2.3); 0.008 (17.7); 0,000 (523.5); -0,008 Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
(20,7); -0,032 (0,5); -0,150 (2,4)  (20.7); -0.032 (0.5); -0.150 (2.4)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,311 (11,4); 9,306 (12,2); 8,785 (8,5); 8,781 (9,1); 8,773 (9,2); 8,769 (9,1); 8,604 (15,0); 8,600 (16,0); 8,507 (4,9); 8,503 (7,4); 8,498 (4,9); 8,487 (5,4); 8,483 (7,7); 8,478 (5,1); 8,319 (0,5); 8,201 (13,4); 8,179 (15,8); 7,942 (9,5); 7,938 (9,4); 7,921 (8,1); 7,916 (8,1); 7,880 (8,6); 7,876 (15,6); 7,872 (9,8); 7,791 (7,6); 7,772 δ = 9.311 (11.4); 9,306 (12.2); 8,785 (8.5); 8,781 (9.1); 8,773 (9,2); 8,769 (9.1); 8,604 (15.0); 8,600 (16.0); 8.507 (4.9); 8.503 (7.4); 8,498 (4.9); 8,487 (5.4); 8,483 (7,7); 8,478 (5.1); 8.319 (0.5); 8,201 (13.4); 8,179 (15,8); 7.942 (9.5); 7.938 (9.4); 7,921 (8,1); 7,916 (8,1); 7,880 (8.6); 7.876 (15.6); 7,872 (9.8); 7,791 (7.6); 7.772
7 4,32 4,49 (8.7) ; 7,656 (7,2); 7,645 (8,1); 7,636 (7,6); 7,625 (8,6); 7 4,32 4,49 (8.7); 7,656 (7.2); 7,645 (8.1); 7.636 (7.6); 7.625 (8.6);
7,617 (2,0); 7,599 (1,9); 7,570 (7,4); 7,551 (15,6); 7,531 7.617 (2.0); 7,599 (1.9); 7,570 (7.4); 7,551 (15.6); 7.531
(9.8) ; 7,492 (9,1); 7,490 (8,6); 7,474 (4,4); 7,472 (4,9); 7,470 (5,0); 5,759 (7,6); 3,333 (249,3); 2,677 (1,3); 2,673 (1,8); 2,669 (1,3); 2,526 (4,8); 2,508 (202,5); 2,504 (262,6); 2,500 (195,5); 2,335 (1,3); 2,331 (1,7); 2,327 (1,3); 1,228 (0,5); 0,146 (0,4); 0,008 (3,1); 0,000 (87,7); -0,008 (3,6); -0,149 (0,4) (9.8); 7,492 (9.1); 7,490 (8,6); 7,474 (4,4); 7,472 (4.9); 7,470 (5.0); 5,759 (7.6); 3,333 (249.3); 2,677 (1.3); 2,673 (1.8); 2,669 (1.3); 2,526 (4,8); 2,508 (202.5); 2,504 (262.6); 2,500 (195.5); 2.335 (1.3); 2.331 (1.7); 2,327 (1,3); 1,228 (0.5); 0.146 (0.4); 0.008 (3.1); 0.000 (87.7); -0.008 (3.6); -0.149 (0.4)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,307 (7,2); 9,303 (7,0); 8,783 (5,5); 8,779 (5,9); 8,771 (5,8); 8,767 (5,7); 8,565 (9,5); 8,560 (9,6); 8,505 (3,2); 8,500 (4,3); 8,495 (3,1); 8,485 (3,4); 8,480 (4,4); 8,475 (3,2); 8,318 (1,2); 8,201 (8,3); 8,179 (9,7); 7,913 (6,1); 7,908 (5,9); 7,891 (5,3); 7,886 (5,2); 7,854 (1,6); 7,847 (13,3); 7,842 (4,8); 7,830 (5,0); 7,826 (15,8); δ = 9.307 (7.2); 9,303 (7,0); 8,783 (5.5); 8,779 (5.9); 8,771 (5.8); 8,767 (5.7); 8,565 (9.5); 8,560 (9.6); 8,505 (3.2); 8,500 (4.3); 8,495 (3,1); 8.485 (3.4); 8,480 (4.4); 8.475 (3.2); 8.318 (1.2); 8,201 (8,3); 8,179 (9.7); 7,913 (6.1); 7.908 (5.9); 7,891 (5.3); 7,886 (5.2); 7,854 (1.6); 7,847 (13.3); 7,842 (4.8); 7,830 (5.0); 7,826 (15.8);
8 4,43 7,656 (4,1); 7,644 (4,1); 7,636 (4,1); 7,624 (3,9); 7,597 8,443,756 (4.1); 7,644 (4,1); 7,636 (4,1); 7.624 (3.9); 7,597
(2,0); 7,591 (16,0); 7,586 (5,2); 7,574 (4,5); 7,569 (13,4); 5,758 (1,8); 3,372 (0,5); 3,330 (596,7); 2,676 (2,9); 2,672 (3,9); 2,667 (2,9); 2,525 (9,8); 2,511 (230,6); 2,507 (465,7); 2,503 (611,7); 2,498 (450,9); 2,403 (0,4); 2,388 (0,3); 2,334 (2,9); 2,329 (4,0); 2,325 (3,0); 1,232 (1,1); 0,146 (1,5); 0,008 (11,8); 0,000 (367,4); -0,009 (14,4); -0,150 (1,7)  (2.0); 7,591 (16,0); 7,586 (5.2); 7,574 (4,5); 7,569 (13.4); 5,758 (1.8); 3,372 (0.5); 3,330 (596.7); 2,676 (2.9); 2,672 (3.9); 2,667 (2.9); 2,525 (9.8); 2,511 (230.6); 2,507 (465,7); 2,503 (611,7); 2,498 (450.9); 2.403 (0.4); 2.388 (0.3); 2,334 (2.9); 2,329 (4.0); 2.325 (3.0); 1,232 (1,1); 0.146 (1.5); 0.008 (11.8); 0,000 (367.4); -0.009 (14.4); -0.150 (1.7)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,304 (2,2); 8,782 (1,6); 8,773 (1,6); 8,503 (1,2); 8,499 (1,7); 8,494 (1,3); 8,483 (1,3); 8,478 (1,7); 8,474 δ = 9.304 (2.2); 8,782 (1.6); 8,773 (1.6); 8,503 (1,2); 8,499 (1.7); 8.494 (1.3); 8.483 (1.3); 8.478 (1.7); 8.474
(1.3) ; 8,213 (3,8); 8,209 (3,9); 8,176 (3,4); 8,155 (3,7); 8,137 (1,0); 7,659 (1,5); 7,646 (1,5); 7,639 (1,5); 7,627(1.3); 8.213 (3.8); 8,209 (3,9); 8,176 (3,4); 8,155 (3.7); 8.137 (1.0); 7.659 (1.5); 7.646 (1.5); 7.639 (1.5); 7.627
(1.4) ; 7,571 (2,4); 7,567 (2,4); 7,550 (2,3); 7,546 (2,3);(1.4); 7,571 (2,4); 7,567 (2,4); 7,550 (2.3); 7,546 (2,3);
9 5,22 5,24 7,468 (5,7); 7,261 (4,7); 3,992 (1,2); 3,966 (3,8); 3,940 9 5.22 5.24 7.468 (5.7); 7,261 (4,7); 3,992 (1.2); 3,966 (3.8); 3,940
(3,9); 3,914 (1,3); 3,331 (36,9); 2,677 (0,4); 2,672 (0,6); 2,668 (0,5); 2,526 (1,4); 2,512 (32,8); 2,508 (67,8); 2,503 (90,2); 2,499 (67,5); 2,495 (34,6); 2,413 (14,5); 2,334 (0,5); 2,330 (0,6); 2,326 (0,5); 2,252 (16,0); 1,232 (0,4); 0,146 (0,5); 0,008 (4,0); 0,000 (111,4); -0,009 (5,1); -0,150 (0,5)  (3.9); 3.914 (1.3); 3,331 (36.9); 2,677 (0.4); 2,672 (0.6); 2,668 (0.5); 2,526 (1.4); 2,512 (32,8); 2,508 (67.8); 2,503 (90.2); 2,499 (67.5); 2,495 (34.6); 2,413 (14.5); 2.334 (0.5); 2,330 (0.6); 2,326 (0.5); 2.252 (16.0); 1,232 (0.4); 0.146 (0.5); 0.008 (4.0); 0.000 (111.4); -0.009 (5.1); -0.150 (0.5)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,315 (3,1); 9,310 (3,1); 8,788 (2,3); 8,784 (2,5); 8,776 (2,4); 8,772 (2,6); 8,511 (1,3); 8,506 (1,8); 8,501 δ = 9.315 (3.1); 9,310 (3,1); 8.788 (2.3); 8.784 (2.5); 8.776 (2.4); 8.772 (2.6); 8,511 (1,3); 8.506 (1.8); 8.501
10 3,45 3,4 (1,4); 8,491 (1,4); 8,485 (1,9); 8,481 (1,4); 8,319 (0,5); 10 3.45 3.4 (1.4); 8.491 (1.4); 8.485 (1.9); 8.481 (1.4); 8.319 (0.5);
8,289 (4,1); 8,285 (4,1); 8,213 (3,5); 8,192 (3,8); 7,773 (6,6); 7,660 (1,7); 7,648 (1,7); 7,638 (3,1); 7,633 (2,7); 7,630 (2,1); 7,617 (2,3); 7,612 (2,3); 7,357 (4,7); 4,175 Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 8,289 (4,1); 8,285 (4,1); 8.213 (3.5); 8,192 (3,8); 7,773 (6.6); 7.606 (1.7); 7.648 (1.7); 7,638 (3,1); 7.633 (2.7); 7.630 (2.1); 7.617 (2.3); 7.612 (2.3); 7,357 (4,7); 4.175 Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
(0,8); 4,148 (2,4); 4,118 (2,4); 4,090 (0,9); 3,334 (14,9); 2,677 (0,5); 2,672 (0,6); 2,668 (0,5); 2,525 (1,9); 2,512 (38,3); 2,508 (76,3); 2,503 (100,2); 2,499 (75,0); 2,413 (15,1); 2,356 (16,0); 2,340 (0,6); 2,334 (0,7); 2,330 (0,8); 2,325 (0,6); 2,252 (0,5); 0,008 (2,5); 0,000 (63,7); -0,008 (3,2)  (0.8); 4.148 (2.4); 4.118 (2.4); 4,090 (0.9); 3,334 (14.9); 2,677 (0.5); 2,672 (0.6); 2,668 (0.5); 2,525 (1.9); 2,512 (38.3); 2,508 (76.3); 2,503 (100,2); 2,499 (75.0); 2,413 (15,1); 2.356 (16.0); 2,340 (0.6); 2.334 (0.7); 2,330 (0.8); 2.325 (0.6); 2.252 (0.5); 0.008 (2.5); 0.000 (63.7); -0.008 (3,2)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,320 (1,2); 8,787 (1,2); 8,507 (1,7); 8,487 (1,8); 8,440 (4,0); 8,218 (3,5); 8,197 (3,9); 7,820 (3,0); 7,800 (3,0); 7,784 (2,2); 7,763 (2,1); 7,662 (1,3); 7,650 (1,4); δ = 9.320 (1.2); 8,787 (1.2); 8.507 (1.7); 8.487 (1.8); 8.440 (4.0); 8.218 (3.5); 8,197 (3.9); 7,820 (3.0); 7,800 (3.0); 7.784 (2.2); 7,763 (2,1); 7.662 (1.3); 7,650 (1.4);
11 4,96 4,97 7,643 (1,5); 7,631 (1,4); 7,374 (2,7); 7,344 (2,6); 4,077 11 4.96 4.97 7.643 (1.5); 7,631 (1.4); 7,374 (2.7); 7,344 (2.6); 4,077
(1,3); 4,051 (4,0); 4,025 (4,1); 3,999 (1,4); 3,338 (12,1); 2,678 (0,4); 2,674 (0,5); 2,669 (0,4); 2,509 (57,7); 2,504 (74,0); 2,500 (55,5); 2,460 (16,0); 2,331 (0,5); 0,008 (1,5); 0,000 (35,8)  (1,3); 4,051 (4.0); 4.025 (4.1); 3,999 (1.4); 3,338 (12.1); 2,678 (0.4); 2,674 (0.5); 2,669 (0.4); 2,509 (57.7); 2,504 (74.0); 2,500 (55.5); 2,460 (16.0); 2.331 (0.5); 0.008 (1.5); 0,000 (35,8)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,323 (2,8); 9,322 (3,0); 9,318 (3,0); 9,316 (2,9); 8,793 (2,4); 8,789 (2,5); 8,781 (2,5); 8,777 (2,6); 8,521 (3,9); 8,519 (4,0); 8,515 (2,3); 8,509 (1,4); 8,499 (1,5); 8,494 (1,8); 8,493 (1,8); 8,489 (1,4); 8,318 (0,4); 8,259 (3,4); 8,238 (3,8); 8,097 (3,1); 8,077 (3,1); 7,851 (1,2); 7,847 (2,1); 7,843 (1,2); 7,830 (1,1); 7,826 (1,9); 7,822 (1,1); 7,664 (1,7); 7,662 (1,7); 7,652 (1,6); 7,650 (1,6); δ = 9.323 (2.8); 9,322 (3.0); 9,318 (3.0); 9.316 (2.9); 8.793 (2.4); 8,789 (2.5); 8,781 (2.5); 8.777 (2.6); 8,521 (3.9); 8,519 (4.0); 8.515 (2.3); 8.509 (1.4); 8,499 (1.5); 8.494 (1.8); 8.493 (1.8); 8.489 (1.4); 8.318 (0.4); 8,259 (3,4); 8.238 (3.8); 8,097 (3.1); 8.077 (3.1); 7.851 (1.2); 7,847 (2.1); 7,843 (1.2); 7.830 (1.1); 7,826 (1.9); 7.822 (1.1); 7.664 (1.7); 7.662 (1.7); 7.652 (1.6); 7,650 (1.6);
12 3,33 3,33 7,644 (1,6); 7,642 (1,6); 7,632 (1,6); 7,630 (1,6); 7,485 12 3.33 3.33 7.644 (1.6); 7.642 (1.6); 7.632 (1.6); 7,630 (1.6); 7,485
(2.4) ; 7,456 (2,3); 5,758 (16,0); 4,273 (0,6); 4,267 (0,5); 4,255 (0,4); 4,246 (1,8); 4,239 (1,7); 4,219 (1,8); 4,211 (1,9); 4,202 (0,4); 4,192 (0,6); 4,184 (0,7); 3,330 (79,8); 2,676 (0,7); 2,672 (0,9); 2,668 (0,7); 2,525 (2,3); 2,521 (2.4); 7.456 (2.3); 5,758 (16.0); 4,273 (0.6); 4,267 (0.5); 4.255 (0.4); 4.246 (1.8); 4,239 (1.7); 4,219 (1.8); 4,211 (1.9); 4,202 (0.4); 4.192 (0.6); 4.184 (0.7); 3,330 (79.8); 2,676 (0.7); 2,672 (0.9); 2,668 (0.7); 2.525 (2.3); 2,521
(3.5) ; 2,512 (51,9); 2,507 (107,9); 2,503 (143,1); 2,498 (104,6); 2,494 (51,7); 2,464 (14,8); 2,334 (0,7); 2,330 (0,9); 2,325 (0,7); 0,146 (1,0); 0,008 (7,7); 0,000 (228,8); -0,009 (10,1); -0,150 (1,0) (3.5); 2,512 (51.9); 2,507 (107.9); 2,503 (143.1); 2,498 (104.6); 2,494 (51.7); 2,464 (14.8); 2.334 (0.7); 2,330 (0.9); 2.325 (0.7); 0.146 (1.0); 0.008 (7.7); 0.000 (228.8); -0.009 (10.1); -0.150 (1.0)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,172 (12,8); 9,167 (13,0); 8,690 (8,5); 8,687 (9,6); 8,678 (9,1); 8,675 (9,5); 8,352 (4,8); 8,348 (7,8); 8,343 (5,3); 8,332 (5,2); 8,328 (8,3); 8,323 (5,4); 7,846 (15,0); 7,824 (16,0); 7,584 (7,6); 7,572 (7,5); 7,564 (7,4); 7,552 δ = 9.172 (12.8); 9.167 (13.0); 8,690 (8.5); 8,687 (9.6); 8,678 (9.1); 8,675 (9.5); 8,352 (4,8); 8,348 (7.8); 8,343 (5.3); 8,332 (5.2); 8,328 (8,3); 8,323 (5.4); 7,846 (15.0); 7,824 (16.0); 7,584 (7.6); 7,572 (7.5); 7,564 (7.4); 7,552
(7.1) ; 7,421 (13,7); 7,415 (14,5); 7,357 (0,3); 7,342(7.1); 7,421 (13,7); 7,415 (14.5); 7.357 (0.3); 7,342
13 2,36 2,47 (0,4); 7,033 (8,2); 7,028 (8,2); 7,011 (7,8); 7,005 (7,9); 13 2.36 2.47 (0.4); 7,033 (8.2); 7.028 (8.2); 7,011 (7.8); 7.005 (7.9);
6,745 (4,0); 6,728 (8,6); 6,710 (4,1); 5,759 (1,8); 4,097 6,745 (4.0); 6,728 (8.6); 6,710 (4,1); 5,759 (1.8); 4,097
(2.2) ; 4,073 (7,1); 4,056 (7,7); 4,049 (8,2); 4,032 (7,2); 4,007 (2,4); 3,332 (97,6); 2,673 (1,2); 2,669 (1,0); 2,508 (144,1); 2,504 (188,9); 2,499 (144,6); 2,330 (1,2); 2,326 (1,0); 0,146 (1,5); 0,007 (11,7); 0,000 (282,0); -0,008 (17,0); -0,150 (1,5) (2.2); 4,073 (7.1); 4.056 (7.7); 4,049 (8.2); 4.032 (7.2); 4,007 (2,4); 3,332 (97.6); 2,673 (1.2); 2,669 (1.0); 2,508 (144.1); 2,504 (188.9); 2,499 (144.6); 2,330 (1.2); 2,326 (1.0); 0.146 (1.5); 0.007 (11.7); 0,000 (282,0); -0.008 (17.0); -0.150 (1.5)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,144 (10,8); 9,140 (11,2); 8,665 (8,6); 8,661 (9,1); δ = 9.144 (10.8); 9.140 (11.2); 8,665 (8.6); 8,661 (9.1);
14 2,5 2,94 8,653 (9,2); 8,649 (9,1); 8,321 (5,0); 8,317 (7,1); 8,311 14 2.5 2.94 8.653 (9.2); 8,649 (9.1); 8,321 (5.0); 8,317 (7.1); 8,311
(4,9); 8,301 (5,4); 8,296 (7,0); 8,291 (5,1); 7,776 (14,5); 7,754 (15,5); 7,567 (6,5); 7,566 (6,2); 7,555 (6,4); 7,554 (6,2); 7,547 (6,4); 7,536 (6,1); 7,534 (5,8); 7,131 (13,4); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] (4.9); 8,301 (5.4); 8.296 (7.0); 8,291 (5.1); 7,776 (14.5); 7,754 (15.5); 7,567 (6.5); 7,566 (6.2); 7,555 (6.4); 7,554 (6.2); 7,547 (6.4); 7,536 (6.1); 7,534 (5.8); 7,131 (13.4); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
7,126 (14,3); 6,925 (8,4); 6,919 (8,0); 6,902 (8,0); 6,897 (7,8); 6,259 (3,9); 6,245 (7,8); 6,232 (4,0); 3,330 (200,6); 2,989 (11,1); 2,974 (16,0); 2,959 (11,4); 2,676 (1,5); 2,672 (2,1); 2,668 (1,6); 2,525 (5,3); 2,512 (116,1); 2,507 (232,1); 2,503 (304,1); 2,498 (223,9); 2,334 (1,5); 2,330 (2,0); 2,325 (1,5); 1,149 (0,4); 1,137 (0,9); 1,132 (1,2); 1,129 (1,2); 1,120 (2,3); 1,117 (2,6); 1,112 (2,5); 1,108 (2,2); 1,100 (4,3); 1,092 (2,2); 1,088 (2,7); 1,083 (2,7); 1,080 (2,6); 1,068 (1,4); 1,064 (1,1); 1,051 (0,5); 0,527 (3,8); 0,516 (11,8); 0,512 (12,6); 0,507 (5,7); 0,502 (5,9); 0,496 (12,2); 0,492 (11,8); 0,482 (4,6); 0,465 (0,5); 0,446 (0,4); 0,305 (0,4); 0,292 (0,4); 0,268 (4,4); 0,257 (13,6); 0,254 (14,2); 0,245 (12,9); 0,242 (14,2); 0,231 (3,7); 0,008 (1,4); 0,000 (41,9); -0,008 (1,8)  7,126 (14,3); 6.925 (8.4); 6,919 (8.0); 6.902 (8.0); 6.897 (7.8); 6.259 (3.9); 6.245 (7.8); 6.232 (4.0); 3,330 (200.6); 2,989 (11.1); 2,974 (16.0); 2,959 (11.4); 2,676 (1.5); 2,672 (2.1); 2,668 (1.6); 2,525 (5.3); 2,512 (116.1); 2,507 (232,1); 2,503 (304,1); 2,498 (223.9); 2.334 (1.5); 2,330 (2.0); 2.325 (1.5); 1,149 (0.4); 1.137 (0.9); 1,132 (1,2); 1.129 (1.2); 1,120 (2,3); 1,117 (2.6); 1,112 (2.5); 1,108 (2,2); 1,100 (4.3); 1,092 (2.2); 1.088 (2.7); 1,083 (2.7); 1,080 (2.6); 1.068 (1.4); 1.064 (1.1); 1.051 (0.5); 0.527 (3.8); 0.516 (11.8); 0.512 (12.6); 0.507 (5.7); 0.502 (5.9); 0.496 (12.2); 0.492 (11.8); 0.482 (4.6); 0.465 (0.5); 0.446 (0.4); 0.305 (0.4); 0.292 (0.4); 0.268 (4.4); 0.257 (13.6); 0.254 (14.2); 0.245 (12.9); 0.242 (14.2); 0.231 (3.7); 0.008 (1.4); 0.000 (41.9); -0.008 (1.8)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,203 (3,8); 8,711 (2,9); 8,701 (2,9); 8,387 (2,9); 8,382 (4,1); 8,377 (2,9); 8,367 (3,2); 8,362 (4,3); 8,357 (3,0); 7,947 (9,0); 7,924 (9,8); 7,641 (8,3); 7,635 (8,6); 7,600 (3,4); 7,588 (3,5); 7,580 (3,4); 7,568 (3,2); 7,296 δ = 9.203 (3.8); 8,711 (2.9); 8,701 (2.9); 8.387 (2.9); 8,382 (4,1); 8.377 (2.9); 8,367 (3,2); 8,362 (4,3); 8.357 (3.0); 7,947 (9.0); 7,924 (9.8); 7,641 (8.3); 7.635 (8.6); 7,600 (3,4); 7,588 (3.5); 7,580 (3,4); 7,568 (3,2); 7,296
15 2 2,14 (4,8); 7,290 (4,7); 7,273 (4,5); 7,267 (4,5); 3,794 (12,8); 15 2 2.14 (4.8); 7,290 (4,7); 7,273 (4,5); 7.267 (4.5); 3,794 (12.8);
3,782 (16,0); 3,770 (13,9); 3,382 (0,5); 3,348 (226,0); 3,246 (13,5); 3,234 (15,9); 3,222 (12,2); 2,676 (0,4); 2,528 (1,0); 2,515 (23,8); 2,511 (47,4); 2,506 (61,7); 2,502 (45,2); 2,498 (22,6); 2,333 (0,4); 0,000 (9,3); - 0,009 (0,4)  3,782 (16.0); 3,770 (13.9); 3,382 (0.5); 3,348 (226,0); 3,246 (13.5); 3,234 (15.9); 3,222 (12.2); 2,676 (0.4); 2,528 (1.0); 2,515 (23.8); 2,511 (47.4); 2,506 (61.7); 2,502 (45.2); 2,498 (22.6); 2.333 (0.4); 0.000 (9.3); - 0.009 (0.4)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,132 (9,1); 9,127 (9,0); 8,663 (6,8); 8,660 (7,4); 8,651 (7,3); 8,648 (7,4); 8,317 (1,1); 8,310 (3,8); 8,305 δ = 9.132 (9.1); 9.127 (9.0); 8,663 (6.8); 8,660 (7.4); 8,651 (7.3); 8,648 (7.4); 8.317 (1.1); 8,310 (3.8); 8.305
(5.5) ; 8,300 (4,0); 8,290 (4,2); 8,284 (5,9); 8,280 (4,1); 7,784 (11,6); 7,762 (12,4); 7,562 (5,4); 7,550 (5,3); 7,542 (5,3); 7,529 (5,0); 7,416 (8,9); 7,397 (15,7); 7,361(5.5); 8,300 (4.0); 8,290 (4,2); 8,284 (5.9); 8,280 (4,1); 7,784 (11,6); 7,762 (12.4); 7,562 (5.4); 7,550 (5.3); 7,542 (5.3); 7,529 (5.0); 7,416 (8,9); 7,397 (15,7); 7,361
16 2,91 3,12 (9,8); 7,343 (16,0); 7,323 (7,8); 7,263 (4,8); 7,245 (6,8); 16 2.91 3.12 (9.8); 7,343 (16.0); 7,323 (7,8); 7,263 (4,8); 7.245 (6.8);
7,227 (2,4); 7,130 (11,0); 7,125 (12,0); 6,946 (6,6); 6,940 (6,4); 6,923 (6,3); 6,918 (6,2); 6,813 (3,1); 6,798 7.227 (2.4); 7,130 (11.0); 7.125 (12.0); 6.946 (6.6); 6,940 (6.4); 6,923 (6.3); 6,918 (6.2); 6,813 (3,1); 6,798
(6.6) ; 6,783 (3,2); 4,370 (13,4); 4,356 (13,4); 3,330 (367,8); 2,676 (1,6); 2,671 (2,3); 2,667 (1,7); 2,525 (5,3); 2,507 (255,7); 2,502 (339,6); 2,498 (255,3); 2,334(6.6); 6,783 (3,2); 4,370 (13.4); 4,356 (13.4); 3,330 (367.8); 2,676 (1.6); 2,671 (2,3); 2,667 (1.7); 2,525 (5.3); 2,507 (255,7); 2,502 (339.6); 2,498 (255.3); 2,334
(1.7) ; 2,329 (2,3); 2,325 (1,8); 1,233 (0,8); 0,008 (1,4); 0,000 (45,2); -0,008 (2,1) (1.7); 2,329 (2,3); 2.325 (1.8); 1.233 (0.8); 0.008 (1.4); 0.000 (45.2); -0.008 (2.1)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,106 (6,3); 9,102 (6,4); 8,653 (4,8); 8,649 (5,1); 8,641 (5,1); 8,637 (5,1); 8,283 (2,7); 8,279 (3,8); 8,273 (2,8); 8,263 (2,9); 8,258 (4,0); 8,253 (2,8); 7,742 (7,8); 7,719 (8,3); 7,549 (3,6); 7,548 (3,6); 7,537 (3,6); 7,529 δ = 9.106 (6.3); 9,102 (6,4); 8,653 (4,8); 8,649 (5.1); 8,641 (5.1); 8,637 (5.1); 8,283 (2.7); 8,279 (3.8); 8,273 (2.8); 8.263 (2.9); 8.258 (4.0); 8,253 (2.8); 7,742 (7.8); 7,719 (8.3); 7,549 (3.6); 7,548 (3.6); 7,537 (3.6); 7,529
17 3,23 3,33 (3,6); 7,528 (3,5); 7,517 (3,4); 7,516 (3,4); 7,432 (7,7); 17 3.23 3.33 (3.6); 7,528 (3.5); 7,517 (3,4); 7,516 (3,4); 7,432 (7,7);
7,413 (10,7); 7,356 (0,4); 7,330 (6,2); 7,312 (11,0); 7,293 (6,0); 7,211 (3,6); 7,193 (5,3); 7,175 (2,0); 6,974 (7,0); 6,969 (8,1); 6,910 (4,6); 6,905 (4,0); 6,888 (4,3); 6,882 (3,9); 6,762 (4,4); 6,744 (4,4); 5,759 (0,7); 4,625 (0,6); 4,608 (2,3); 4,591 (3,6); 4,574 (2,3); 4,557 (0,6); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 7.413 (10.7); 7.356 (0.4); 7,330 (6.2); 7,312 (11.0); 7,293 (6.0); 7.211 (3.6); 7,193 (5,3); 7.175 (2.0); 6,974 (7.0); 6,969 (8,1); 6.910 (4.6); 6.905 (4.0); 6,888 (4,3); 6,882 (3.9); 6,762 (4.4); 6,744 (4.4); 5,759 (0.7); 4.625 (0.6); 4,608 (2,3); 4,591 (3.6); 4.574 (2.3); 4,557 (0.6); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
3,332 (41,4); 2,677 (0,4); 2,672 (0,6); 2,668 (0,5); 2,526 (1,4); 2,508 (70,0); 2,503 (91,6); 2,499 (68,3); 2,335 (0,5); 2,330 (0,6); 2,326 (0,5); 2,275 (1,1); 2,076 (2,7); 1,474 (16,0); 1,457 (16,0); 1,421 (0,5); 1,404 (0,5); 1,257 (0,4); 1,240 (0,5); 0,008 (0,5); 0,000 (13,5); - 0,008 (0,6)  3,332 (41.4); 2,677 (0.4); 2,672 (0.6); 2,668 (0.5); 2,526 (1.4); 2,508 (70.0); 2,503 (91.6); 2,499 (68.3); 2.335 (0.5); 2,330 (0.6); 2,326 (0.5); 2.275 (1.1); 2.076 (2.7); 1,474 (16.0); 1,457 (16.0); 1,421 (0.5); 1.404 (0.5); 1.257 (0.4); 1.240 (0.5); 0.008 (0.5); 0.000 (13.5); - 0.008 (0.6)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,177 (3,3); 9,172 (3,4); 8,692 (2,5); 8,683 (2,4); 8,680 (2,5); 8,354 (1,9); 8,339 (1,5); 8,334 (2,1); 7,902 (6,9); 7,879 (3,6); 7,586 (1,7); 7,573 (1,8); 7,566 (1,8); 7,554 (1,6); 7,411 (5,7); 7,341 (4,0); 7,336 (4,2); 7,181 δ = 9.177 (3.3); 9,172 (3,4); 8,692 (2.5); 8.683 (2.4); 8,680 (2.5); 8,354 (1.9); 8.399 (1.5); 8,334 (2,1); 7.902 (6.9); 7,879 (3.6); 7,586 (1.7); 7,573 (1.8); 7,566 (1.8); 7,554 (1.6); 7,411 (5.7); 7,341 (4.0); 7,336 (4,2); 7,181
18 4,45 4,51 (5,0); 7,115 (2,0); 7,110 (2,1); 7,093 (2,0); 7,088 (2,0); 18 4.45 4.51 (5.0); 7.115 (2.0); 7,110 (2,1); 7,093 (2.0); 7.088 (2.0);
4,056 (0,4); 4,038 (1,2); 4,020 (1,2); 4,002 (0,5); 3,880 4.056 (0.4); 4.038 (1.2); 4,020 (1.2); 4.002 (0.5); 3,880
(1.2) ; 3,854 (3,8); 3,828 (3,9); 3,802 (1,4); 3,332 (34,3); 2,673 (0,6); 2,504 (94,6); 2,350 (15,3); 2,180 (16,0); 1,990 (5,0); 1,231 (0,5); 1,193 (1,3); 1,176 (2,6); 1,158(1.2); 3,854 (3.8); 3.828 (3.9); 3.802 (1.4); 3,332 (34.3); 2,673 (0.6); 2,504 (94.6); 2,350 (15.3); 2,180 (16.0); 1,990 (5.0); 1.231 (0.5); 1.193 (1.3); 1.176 (2.6); 1,158
(1.3) ; 0,000 (2,6) (1.3); 0,000 (2,6)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,193 (3,1); 9,189 (3,2); 8,708 (2,3); 8,704 (2,5); 8,696 (2,5); 8,692 (2,5); 8,380 (1,3); 8,376 (1,8); 8,370 δ = 9.193 (3.1); 9,189 (3,2); 8,708 (2,3); 8,704 (2.5); 8.696 (2.5); 8,692 (2.5); 8,380 (1.3); 8.376 (1.8); 8,370
(1.3) ; 8,360 (1,5); 8,354 (2,0); 8,350 (1,4); 8,318 (1,0); 8,037 (4,3); 7,953 (3,5); 7,931 (3,9); 7,734 (6,2); 7,598 (1,7); 7,586 (1,7); 7,578 (1,7); 7,566 (1,7); 7,565 (1,6);(1.3); 8.360 (1.5); 8.354 (2.0); 8,350 (1.4); 8.318 (1.0); 8.037 (4.3); 7,953 (3.5); 7,931 (3.9); 7,734 (6.2); 7,598 (1.7); 7,586 (1.7); 7,578 (1.7); 7,566 (1.7); 7,565 (1.6);
19 3,07 7,516 (3,8); 7,510 (3,8); 7,238 (4,9); 7,218 (2,2); 7,213 19 3.07 7.516 (3.8); 7,510 (3.8); 7.238 (4.9); 7.218 (2.2); 7,213
(2,1); 7,196 (2,1); 7,190 (2,0); 4,108 (0,6); 4,099 (0,5); 4,081 (0,7); 4,071 (1,4); 4,056 (0,6); 4,044 (1,5); 4,030 (2.1); 7,196 (2,1); 7.190 (2.0); 4.108 (0.6); 4,099 (0.5); 4,081 (0.7); 4,071 (1.4); 4.056 (0.6); 4,044 (1.5); 4,030
(1.4) ; 4,017 (0,7); 4,002 (1,5); 3,993 (0,7); 3,975 (0,6); 3,966 (0,6); 3,331 (36,1); 3,308 (0,5); 2,672 (0,5); 2,508 (59,1); 2,503 (76,1); 2,499 (56,7); 2,350 (0,8); 2,334 (0,5); 2,330 (0,7); 2,325 (0,6); 2,308 (15,7); 2,282 (16,0); 2,180 (0,8); 0,000 (0,9) (1.4); 4.017 (0.7); 4.002 (1.5); 3,993 (0.7); 3.975 (0.6); 3.966 (0.6); 3,331 (36.1); 3.308 (0.5); 2,672 (0.5); 2,508 (59.1); 2,503 (76.1); 2,499 (56.7); 2,350 (0.8); 2.334 (0.5); 2,330 (0.7); 2.325 (0.6); 2.308 (15.7); 2,282 (16.0); 2,180 (0.8); 0,000 (0.9)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,197 (2,9); 9,193 (2,9); 9,191 (2,8); 8,711 (2,3); 8,707 (2,6); 8,699 (2,5); 8,695 (2,6); 8,382 (1,4); 8,376 (1,8); 8,372 (1,6); 8,362 (5,3); 8,352 (1,7); 7,947 (3,8); 7,925 (4,2); 7,599 (1,7); 7,597 (1,8); 7,587 (1,6); 7,585 (1,7); 7,579 (1,7); 7,577 (1,7); 7,565 (2,2); 7,560 (3,5); δ = 9.197 (2.9); 9.193 (2.9); 9,191 (2,8); 8.711 (2.3); 8,707 (2.6); 8,699 (2.5); 8.695 (2.6); 8,382 (1.4); 8.376 (1.8); 8.372 (1.6); 8,362 (5.3); 8.352 (1.7); 7,947 (3.8); 7.925 (4.2); 7,599 (1.7); 7,597 (1.8); 7,587 (1.6); 7,585 (1.7); 7,579 (1.7); 7,577 (1.7); 7,565 (2,2); 7,560 (3.5);
20 4,18 4,22 7,557 (3,6); 7,551 (3,3); 7,540 (2,9); 7,274 (2,6); 7,244 20 4,18 4,22 7,557 (3,6); 7,551 (3.3); 7,540 (2.9); 7.274 (2.6); 7,244
(2,7); 7,207 (2,0); 7,201 (1,9); 7,184 (1,9); 7,179 (1,9); 5,759 (2,4); 3,922 (1,2); 3,895 (3,9); 3,869 (4,1); 3,843 (1,4); 3,333 (29,2); 2,673 (0,4); 2,526 (0,9); 2,513 (20,8); 2,508 (43,4); 2,504 (57,9); 2,499 (42,1); 2,495 (20,4); 2,380 (16,0); 2,331 (0,4); 2,304 (0,6); 0,000 (0,4)  (2.7); 7,207 (2,0); 7,201 (1.9); 7.184 (1.9); 7.179 (1.9); 5,759 (2,4); 3.922 (1.2); 3,895 (3.9); 3,869 (4,1); 3,843 (1.4); 3,333 (29.2); 2,673 (0.4); 2,526 (0.9); 2,513 (20.8); 2,508 (43.4); 2,504 (57.9); 2,499 (42.1); 2,495 (20.4); 2,380 (16.0); 2,331 (0.4); 2.304 (0.6); 0,000 (0.4)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,212 (3,0); 9,208 (3,1); 8,721 (2,0); 8,718 (2,2); 8,709 (2,2); 8,706 (2,2); 8,598 (3,8); 8,400 (1,3); 8,396 δ = 9.212 (3.0); 9,208 (3,1); 8,721 (2.0); 8.718 (2.2); 8,709 (2.2); 8.706 (2.2); 8,598 (3.8); 8,400 (1.3); 8.396
21 2,85 2,9 (1,8); 8,390 (1,3); 8,380 (1,4); 8,375 (1,9); 8,370 (1,4); 21 2.85 2.9 (1.8); 8.390 (1.3); 8,380 (1.4); 8.375 (1.9); 8,370 (1.4);
7,998 (3,6); 7,976 (3,9); 7,849 (3,0); 7,829 (3,0); 7,706 (3,3); 7,701 (3,5); 7,608 (1,6); 7,596 (1,6); 7,589 (1,6); 7,577 (1,5); 7,351 (2,5); 7,321 (2,6); 7,307 (2,1); 7,301 Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 7,998 (3.6); 7.976 (3.9); 7,849 (3.0); 7.829 (3.0); 7,706 (3.3); 7.701 (3.5); 7.608 (1.6); 7,596 (1.6); 7,589 (1.6); 7,577 (1.5); 7.351 (2.5); 7,321 (2,6); 7,307 (2,1); 7,301 Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
(2,0); 7,284 (1 ,9); 7,279 (1 ,9); 5,755 (5,4); 4,159 (0,4); 4,149 (0,5); 4,132 (0,8); 4, 122 (1 ,7); 4, 107 (1 ,6); 4,095 (1 ,8); 4,080 (1 ,7); 4,069 (0,8); 4,053 (0,6); 4,043 (0,4); 3,338 (104,4); 3,31 1 (0,4); 2,673 (0,3); 2,509 (44,0); 2,504 (57,4); 2,500 (42,8); 2,334 (16,0); 1 ,990 (0,7); 1 ,176 (0,4); 0,008 (2,5); 0,000 (61 ,8); -0,008 (3,1) (2.0); 7,284 (1, 9); 7,279 (1, 9); 5,755 (5.4); 4.159 (0.4); 4,149 (0.5); 4,132 (0.8); 4, 122 (1, 7); 4, 107 (1, 6); 4.095 (1, 8); 4,080 (1, 7); 4.069 (0.8); 4,053 (0.6); 4,043 (0.4); 3,338 (104.4); 3.31 1 (0.4); 2,673 (0.3); 2,509 (44.0); 2,504 (57.4); 2,500 (42.8); 2,334 (16.0); 1, 990 (0.7); 1, 176 (0.4); 0.008 (2.5); 0,000 (61, 8); -0.008 (3,1)
'H-NMR (400,0 MHz, de-DMSO): 'H-NMR (400.0 MHz, de-DMSO):
δ = 9,303 (3,6); 9,299 (3,6); 8,785 (2,8); 8,781 (3,0); 8,773 (3,0); 8,769 (3,0); 8,501 (1 ,6); 8,497 (2,1); 8,491 (1 ,6); 8,481 (1 ,8); 8,475 (2,2); 8,471 (1 ,7); 8,187 (4,9); 8,183 (4,8); 8,160 (4,4); 8, 138 (8,4); 7,659 (2,0); 7,657 δ = 9.303 (3.6); 9,299 (3.6); 8,785 (2.8); 8,781 (3.0); 8,773 (3.0); 8.769 (3.0); 8,501 (1, 6); 8.497 (2.1); 8,491 (1,6); 8, 481 (1, 8); 8.475 (2.2); 8,471 (1, 7); 8,187 (4,9); 8,183 (4,8); 8,160 (4.4); 8, 138 (8.4); 7.659 (2.0); 7,657
(2.0) ; 7,647 (2,0); 7,645 (2,0); 7,639 (2,0); 7,637 (1 ,9); 7,627 (1 ,9); 7,625 (1 ,9); 7,574 (3,2); 7,569 (3,2); 7,553(2.0); 7.647 (2.0); 7.645 (2.0); 7.639 (2.0); 7,637 (1, 9); 7,627 (1, 9); 7.625 (1, 9); 7,574 (3.2); 7,569 (3,2); 7,553
(3.1) ; 7,548 (3,1); 7,474 (1 ,8); 7,457 (3,7); 7,454 (3,6);(3.1); 7,548 (3.1); 7,474 (1, 8); 7,457 (3,7); 7.454 (3.6);
22 4,32 4,44 7,435 (1 ,8); 7,430 (1 ,9); 7,418 (2, 1); 7,413 (2,4); 7,398 22 4.32 4.44 7.435 (1, 8); 7,430 (1, 9); 7,418 (2, 1); 7.413 (2.4); 7,398
(1 , 1); 7,394 (1 ,2); 7,339 (1 ,1); 7,335 (1 ,6); 7,320 (4,0); 7,316 (3,4); 7,307 (2,7); 7,304 (2,6); 7,290 (2,2); 7,287 (2,4); 7,271 (0,8); 7,268 (0,8); 5,759 (1 ,6); 3,335 (10,3); 2,915 (2,1); 2,897 (6,9); 2,878 (7,0); 2,860 (2,2); 2,673 (0,5); 2,668 (0,3); 2,526 (0,9); 2,513 (26,6); 2,508 (54,0); 2,504 (70,4); 2,499 (51 ,0); 2,495 (24,9); 2,335 (0,3); 2,330 (0,5); 2,326 (0,3); 2,077 (2, 1); 1 ,185 (7,6); 1 ,167 (16,0); 1 ,148 (7,3); 0,008 (2,2); 0,000 (64,3); - 0,009 (2,4)  (1, 1); 7,394 (1, 2); 7,339 (1, 1); 7,335 (1, 6); 7,320 (4.0); 7,316 (3,4); 7,307 (2.7); 7.304 (2.6); 7.290 (2.2); 7,287 (2,4); 7.271 (0.8); 7.268 (0.8); 5,759 (1,6); 3,335 (10.3); 2,915 (2.1); 2,897 (6.9); 2,878 (7.0); 2,860 (2.2); 2,673 (0.5); 2,668 (0.3); 2,526 (0.9); 2,513 (26.6); 2,508 (54.0); 2,504 (70.4); 2,499 (51, 0); 2,495 (24.9); 2.335 (0.3); 2.330 (0.5); 2,326 (0.3); 2,077 (2, 1); 1, 185 (7,6); 1, 167 (16.0); 1, 148 (7,3); 0.008 (2.2); 0,000 (64.3); - 0.009 (2.4)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,31 1 (4,7); 9,306 (4,9); 8,794 (3,4); 8,791 (3,6); 8,782 (3,6); 8,779 (3,6); 8,509 (1 ,9); 8,505 (2,8); 8,500 (2,0); 8,489 (2,2); 8,485 (2,9); 8,480 (2,0); 8,329 (6,1); 8,325 (6,4); 8,321 (3,7); 8,21 1 (5, 1); 8, 190 (5,5); 7,962 δ = 9.31 1 (4.7); 9,306 (4.9); 8,794 (3,4); 8,791 (3.6); 8,782 (3.6); 8,779 (3.6); 8,509 (1, 9); 8,505 (2.8); 8,500 (2.0); 8.489 (2.2); 8.485 (2.9); 8,480 (2.0); 8,329 (6,1); 8,325 (6.4); 8,321 (3,7); 8.21 1 (5, 1); 8, 190 (5.5); 7.962
(3.0) ; 7,959 (3,3); 7,943 (3,6); 7,940 (3,7); 7,775 (0,5); 7,743 (1 ,8); 7,727 (3,7); 7,724 (3,6); 7,708 (2,5); 7,705(3.0); 7,959 (3.3); 7,943 (3.6); 7,940 (3.7); 7,775 (0.5); 7,743 (1, 8); 7,727 (3.7); 7,724 (3.6); 7,708 (2.5); 7,705
23 2,25 2,24 (2,5); 7,694 (2,4); 7,691 (2,4); 7,676 (3,6); 7,672 (3,6); 23 2.25 2.24 (2.5); 7.694 (2.4); 7.691 (2.4); 7.676 (3.6); 7,672 (3.6);
7,664 (3,1); 7,653 (3,8); 7,643 (6, 1); 7,639 (4,3); 7,633 7,664 (3,1); 7,653 (3.8); 7,643 (6, 1); 7,639 (4,3); 7,633
(3.1) ; 7,622 (3,5); 7,618 (3,5); 7,509 (3,8); 7,507 (3,8); 7,491 (3,3); 7,488 (3,1); 7,271 (0,9); 7,253 (0,4); 3,335 (13,2); 3,313 (1 ,3); 2,718 (0,6); 2,700 (1 ,8); 2,681 (2,4); 2,673 (0,9); 2,666 (2,7); 2,647 (2,2); 2,629 (0,7); 2,509 (56,8); 2,504 (71 ,7); 2,500 (54,7); 2,341 (0,8); 2,323 (2,3); 2,305 (2,5); 2,289 (2,2); 2,271 (1 ,9); 2,253 (0,6); 0,866 (7,7); 0,848 (16,0); 0,829 (7,3); 0,000 (44,7)(3.1); 7.622 (3.5); 7.618 (3.5); 7,509 (3,8); 7.507 (3.8); 7,491 (3,3); 7,488 (3,1); 7.271 (0.9); 7.253 (0.4); 3,335 (13.2); 3,313 (1, 3); 2,718 (0.6); 2,700 (1, 8); 2,681 (2,4); 2,673 (0.9); 2,666 (2.7); 2,647 (2.2); 2,629 (0.7); 2,509 (56.8); 2,504 (71, 7); 2,500 (54.7); 2,341 (0.8); 2,323 (2,3); 2.305 (2.5); 2,289 (2,2); 2,271 (1, 9); 2.253 (0.6); 0.866 (7.7); 0.848 (16.0); 0.829 (7.3); 0,000 (44.7)
'H-NMR (400,0 MHz, de-DMSO): 'H-NMR (400.0 MHz, de-DMSO):
δ = 9,449 (15,4); 9,221 (1 1 ,4); 9,217 (1 1 ,7); 8,808 (14,9); 8,803 (15,0); 8,723 (8,7); 8,719 (9,3); 8,71 1 (9,2); 8,707 (9,3); 8,403 (4,9); 8,399 (7,0); 8,394 (5,1); 8,383 (5,4); 8,378 (7,2); 8,374 (5,2); 8,319 (0,5); 8,291 δ = 9.449 (15.4); 9,221 (1 1, 4); 9,217 (1 1, 7); 8,808 (14.9); 8,803 (15.0); 8,723 (8,7); 8,719 (9.3); 8.71 1 (9.2); 8,707 (9.3); 8,403 (4,9); 8,399 (7.0); 8,394 (5.1); 8,383 (5.4); 8,378 (7.2); 8.374 (5.2); 8.319 (0.5); 8,291
24 1 ,04 2,47 (0,3); 8,257 (6,7); 8,253 (7,3); 8,244 (7, 1); 8,240 (7,0); 24 1, 04 2.47 (0.3); 8,257 (6,7); 8,253 (7.3); 8,244 (7, 1); 8,240 (7.0);
7,997 (13,9); 7,975 (16,0); 7,651 (10, 1); 7,646 (1 1 ,3); 7,629 (13,5); 7,624 (13,5); 7,612 (8,7); 7,605 (6,1); 7,602 (7,2); 7,594 (6,5); 7,582 (6, 1); 7,580 (5,9); 6,931 (1 1 ,0); 6,910 (10,5); 6,838 (6,2); 6,824 (6,7); 6,821 (6,8); 6,808 (5,8); 5,759 (2,1); 3,335 (162,3); 2,678 Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 7.997 (13.9); 7,975 (16.0); 7.651 (10, 1); 7.646 (1, 3); 7,629 (13.5); 7,624 (13.5); 7,612 (8,7); 7,605 (6.1); 7.602 (7.2); 7,594 (6.5); 7,582 (6, 1); 7,580 (5.9); 6.931 (1 1, 0); 6.910 (10.5); 6,838 (6.2); 6,824 (6,7); 6,821 (6.8); 6,808 (5.8); 5,759 (2,1); 3,335 (162.3); 2,678 Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
(0,9); 2,673 (1,2); 2,669 (0,9); 2,526 (3,0); 2,513 (67,4); 2,509 (135,1); 2,504 (176,8); 2,500 (130,0); 2,335 (0,8); 2,331 (1,1); 2,326 (0,8); 1,352 (0,6); 1,225 (0,8); 0,146 (1,2); 0,008 (9,4); 0,000 (258,3); -0,008 (11,2); -0,025 (0,4); -0,029 (0,3); -0,060 (0,6); -0,150 (1,2)  (0.9); 2,673 (1.2); 2,669 (0.9); 2.526 (3.0); 2,513 (67.4); 2,509 (135.1); 2,504 (176,8); 2,500 (130.0); 2.335 (0.8); 2.331 (1.1); 2,326 (0.8); 1,352 (0.6); 1.225 (0.8); 0.146 (1.2); 0.008 (9.4); 0,000 (258.3); -0.008 (11.2); -0.025 (0.4); -0.029 (0.3); -0.060 (0.6); -0.150 (1.2)
'H-NMR (601,6 MHz, de-DMSO):  'H-NMR (601.6 MHz, de-DMSO):
δ = 9,954 (0,4); 9,302 (8,1); 8,784 (5,9); 8,777 (6,2); 8,560 (14,0); 8,557 (14,7); 8,492 (4,8); 8,489 (7,5); 8,486 (5,3); 8,479 (5,3); 8,476 (7,8); 8,473 (5,4); 8,404 (2,2); 8,325 (0,4); 8,243 (14,4); 8,228 (16,0); 7,907 δ = 9.954 (0.4); 9,302 (8,1); 8,784 (5.9); 8,777 (6.2); 8,560 (14.0); 8,557 (14.7); 8,492 (4,8); 8,489 (7.5); 8,486 (5,3); 8,479 (5,3); 8.476 (7.8); 8,473 (5.4); 8.404 (2.2); 8.325 (0.4); 8,243 (14.4); 8.228 (16.0); 7,907
25 1,64 (8,9); 7,904 (9,4); 7,893 (10,1); 7,889 (10,6); 7,843 25 1.64 (8.9); 7.904 (9.4); 7,893 (10.1); 7,889 (10.6); 7,843
(0,4); 7,651 (6,2); 7,643 (6,4); 7,638 (6,4); 7,629 (6,1); 7,202 (2,1); 5,765 (2,0); 3,352 (8,3); 2,894 (0,4); 2,735 (0,5); 2,620 (0,5); 2,523 (1,6); 2,511 (70,7); 2,508 (97,6); 2,505 (74,1); 2,391 (0,6); 0,097 (0,5); 0,005 (3,9); 0,000 (102,4); -0,099 (0,5)  (0.4); 7.651 (6.2); 7,643 (6.4); 7,638 (6.4); 7,629 (6,1); 7,202 (2,1); 5,765 (2.0); 3,352 (8.3); 2,894 (0.4); 2,735 (0.5); 2,620 (0.5); 2,523 (1.6); 2,511 (70,7); 2,508 (97.6); 2,505 (74.1); 2.391 (0.6); 0.097 (0.5); 0.005 (3.9); 0,000 (102.4); -0.099 (0.5)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,290 (9,6); 9,285 (9,7); 8,776 (7,1); 8,767 (7,0); 8,697 (13,9); 8,692 (14,2); 8,621 (14,1); 8,615 (14,3); 8,483 (4,6); 8,479 (6,9); 8,474 (4,5); 8,463 (4,8); 8,459 (7,1); 8,455 (4,4); 8,454 (4,4); 8,226 (11,0); 8,204 δ = 9.290 (9.6); 9.285 (9.7); 8,776 (7.1); 8,767 (7.0); 8,697 (13.9); 8,692 (14.2); 8,621 (14,1); 8,615 (14,3); 8,483 (4,6); 8,479 (6,9); 8,474 (4,5); 8,463 (4,8); 8,459 (7,1); 8,455 (4,4); 8,454 (4,4); 8.226 (11.0); 8,204
26 2,2 (16,0); 8,114 (9,4); 8,108 (9,0); 8,092 (6,4); 8,086 (6,3); 26 2.2 (16.0); 8,114 (9.4); 8,108 (9,0); 8.092 (6.4); 8,086 (6.3);
7,828 (13,9); 7,824 (14,2); 7,651 (6,4); 7,639 (6,3); 7,631 (6,3); 7,619 (5,9); 6,625 (8,7); 6,620 (13,4); 6,614 (8,4); 3,333 (72,3); 2,675 (0,6); 2,510 (73,4); 2,506 (92,7); 2,502 (68,6); 2,333 (0,6); 2,089 (0,7); 0,146 (0,5); 0,007 (5,7); 0,000 (110,4); -0,150 (0,6)  7,828 (13.9); 7,824 (14.2); 7.651 (6.4); 7,639 (6.3); 7,631 (6.3); 7,619 (5.9); 6.625 (8.7); 6,620 (13.4); 6,614 (8.4); 3,333 (72.3); 2,675 (0.6); 2,510 (73.4); 2,506 (92.7); 2,502 (68.6); 2.333 (0.6); 2.089 (0.7); 0.146 (0.5); 0.007 (5.7); 0,000 (110.4); -0.150 (0.6)
'H-NMR (601,6 MHz, de-DMSO):  'H-NMR (601.6 MHz, de-DMSO):
δ = 9,300 (16,0); 8,786 (5,1); 8,784 (5,3); 8,776 (13,9); 8,772 (8,9); 8,494 (2,7); 8,491 (4,1); 8,488 (2,7); 8,481 (3,0); 8,478 (4,2); 8,475 (2,7); 8,298 (12,3); 8,269 (7,6); 8,254 (9,6); 8,139 (5,4); 8,135 (5,2); 8,124 (4,5); 8,121 δ = 9,300 (16.0); 8,786 (5.1); 8,784 (5.3); 8,776 (13.9); 8,772 (8.9); 8.494 (2.7); 8,491 (4,1); 8,488 (2,7); 8.481 (3.0); 8,478 (4,2); 8.475 (2.7); 8,298 (12.3); 8.269 (7.6); 8,254 (9.6); 8,139 (5.4); 8.135 (5.2); 8.124 (4.5); 8,121
27 3,42 (4,3); 7,760 (0,4); 7,652 (3,8); 7,644 (3,7); 7,639 (3,8); 27, 3.42 (4.3); 7,760 (0.4); 7,652 (3.8); 7,644 (3.7); 7,639 (3.8);
7,631 (3,7); 3,346 (50,8); 2,996 (0,4); 2,618 (0,5); 2,524 (0,9); 2,509 (64,3); 2,507 (87,0); 2,504 (63,4); 2,391 (0,5); 2,089 (0,6); 1,946 (0,4); 1,223 (0,4); 1,148 (0,4); 1,088 (0,7); 1,066 (0,3); 1,038 (0,5); 0,005 (2,5); 0,000 (69,0); -0,006 (2,7); -0,100 (0,3)  7,631 (3.7); 3.346 (50.8); 2.996 (0.4); 2,618 (0.5); 2,524 (0.9); 2,509 (64.3); 2,507 (87.0); 2,504 (63.4); 2.391 (0.5); 2.089 (0.6); 1,946 (0.4); 1,223 (0.4); 1,148 (0.4); 1.088 (0.7); 1.066 (0.3); 1.038 (0.5); 0.005 (2.5); 0.000 (69.0); -0.006 (2.7); -0.100 (0.3)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,305 (3,2); 8,837 (11,4); 8,777 (16,0); 8,771 (15,8); 8,490 (6,4); 8,470 (6,7); 8,319 (0,4); 8,273 (11,0); 8,251 (14,5); 8,126 (8,6); 8,120 (8,7); 8,103 (6,5); 8,098 (6,6); 7,976 (0,6); 7,656 (4,1); 7,644 (4,6); δ = 9.305 (3.2); 8,837 (11,4); 8,777 (16.0); 8,771 (15,8); 8,490 (6.4); 8,470 (6,7); 8,319 (0.4); 8,273 (11.0); 8,251 (14.5); 8,126 (8,6); 8,120 (8,7); 8,103 (6.5); 8,098 (6.6); 7.976 (0.6); 7,656 (4,1); 7,644 (4.6);
28 3,46 7,637 (4,5); 7,625 (3,8); 7,121 (12,0); 7,115 (12,1); 28 3.46 7.637 (4.5); 7.625 (3.8); 7,121 (12,0); 7,115 (12,1);
6,709 (0,6); 3,333 (43,9); 2,676 (0,6); 2,511 (70,7); 2,507 (90,6); 2,503 (70,5); 2,334 (0,5); 1,223 (0,7); 1,144 (0,7); 1,100 (0,4); 1,089 (0,9); 1,039 (0,6); 0,866 (0,3); 0,841 (0,4); 0,824 (0,3); 0,146 (0,5); 0,000 (99,6); -0,150 (0,5)  6,709 (0.6); 3,333 (43.9); 2,676 (0.6); 2,511 (70,7); 2,507 (90.6); 2,503 (70.5); 2.334 (0.5); 1,223 (0.7); 1,144 (0.7); 1,100 (0.4); 1.089 (0.9); 1.039 (0.6); 0.866 (0.3); 0.841 (0.4); 0.824 (0.3); 0.146 (0.5); 0,000 (99.6); -0.150 (0.5)
29 4,05 'H-NMR (400,0 MHz, de-DMSO): Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 29 4,05 'H-NMR (400.0 MHz, de-DMSO): Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
δ = 9,306 (6,1); 8,885 (8,6); 8,881 (8,3); 8,878 (8,9); 8,790 (4,6); 8,777 (16,0); 8,772 (13,8); 8,502 (3,7); 8,497 (5,3); 8,492 (3,9); 8,482 (4,0); 8,477 (5,5); 8,472 (3,9); 8,318 (0,5); 8,286 (10,3); 8,264 (13,5); 8,128 (7,9); 8,122 (7,8); 8,105 (6,1); 8,100 (6,2); 7,706 (0,3); 7,659 (4,5); 7,647 (4,6); 7,639 (4,6); 7,627 (4,3); 7,144 (10,2); 7,137 (10,3); 7,004 (0,4); 6,998 (0,4); 3,328 (63,0); 2,679 (0,6); 2,674 (0,8); 2,670 (0,6); 2,528 (2,2); 2,514 (43,3); 2,510 (87,9); 2,505 (117,8); 2,501 (88,8); 2,497 (45,6); 2,337 (0,5); 2,332 (0,7); 2,328 (0,6); 0,146 (0,8); 0,008 (6,5); 0,000 (164,1); -0,008 (8,1); -0,026 (0,4); -0,150 (0,8)  δ = 9.306 (6.1); 8.885 (8.6); 8,881 (8,3); 8,878 (8.9); 8,790 (4,6); 8,777 (16.0); 8,772 (13.8); 8,502 (3.7); 8.497 (5.3); 8,492 (3.9); 8,482 (4.0); 8.477 (5.5); 8,472 (3.9); 8.318 (0.5); 8,286 (10.3); 8,264 (13.5); 8,128 (7.9); 8,122 (7,8); 8,105 (6,1); 8,100 (6.2); 7.706 (0.3); 7,659 (4,5); 7,647 (4,6); 7,639 (4,6); 7,627 (4,3); 7,144 (10,2); 7.137 (10.3); 7.004 (0.4); 6,998 (0.4); 3,328 (63.0); 2,679 (0.6); 2,674 (0.8); 2,670 (0.6); 2.528 (2.2); 2,514 (43,3); 2,510 (87.9); 2,505 (117.8); 2,501 (88,8); 2,497 (45.6); 2.377 (0.5); 2.332 (0.7); 2.328 (0.6); 0.146 (0.8); 0.008 (6.5); 0,000 (164,1); -0.008 (8.1); -0.026 (0.4); -0.150 (0.8)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,316 (0,6); 8,931 (2,0); 8,823 (3,0); 8,792 (0,7); 8,755 (3,7); 8,749 (3,8); 8,499 (1,7); 8,479 (1,7); 8,318 (0,7); 8,277 (2,2); 8,255 (4,1); 8,210 (2,0); 8,206 (2,0); 8,188 (1,0); 8,184 (1,1); 7,662 (0,9); 7,650 (1,1); 7,643 δ = 9.316 (0.6); 8,931 (2.0); 8.823 (3.0); 8,792 (0.7); 8,755 (3.7); 8,749 (3.8); 8,499 (1.7); 8.479 (1.7); 8.318 (0.7); 8.277 (2.2); 8,255 (4,1); 8.210 (2.0); 8.206 (2.0); 8.188 (1.0); 8.184 (1.1); 7.662 (0.9); 7.650 (1.1); 7.643
30 2 (1,1); 7,631 (0,9); 7,512 (1,0); 7,501 (1,6); 7,490 (0,9); 30 2 (1,1); 7,631 (0.9); 7,512 (1.0); 7,501 (1.6); 7,490 (0.9);
7,265 (3,8); 7,259 (4,0); 4,553 (2,6); 3,328 (28,5); 3,304 (0,4); 3,177 (0,5); 3,164 (0,5); 2,673 (0,4); 2,509 (50,4); 2,504 (66,9); 2,500 (51,8); 2,482 (5,0); 2,331 (0,4); 2,327 (0,3); 2,119 (7,4); 2,087 (0,4); 1,229 (0,5); 1,142 (16,0); 1,053 (0,9); 0,146 (0,4); 0,008 (2,9); 0,000 (73,9); -0,149 (0,4)  7.265 (3.8); 7.259 (4.0); 4,553 (2.6); 3,328 (28.5); 3.304 (0.4); 3.177 (0.5); 3.164 (0.5); 2,673 (0.4); 2,509 (50.4); 2,504 (66.9); 2,500 (51.8); 2,482 (5.0); 2,331 (0.4); 2,327 (0.3); 2,119 (7,4); 2,087 (0.4); 1,229 (0.5); 1,142 (16.0); 1,053 (0.9); 0.146 (0.4); 0.008 (2.9); 0,000 (73.9); -0.149 (0.4)
'H-NMR (400,0 MHz, de-DMSO):  'H-NMR (400.0 MHz, de-DMSO):
δ = 9,399 (16,0); 9,307 (7,2); 9,303 (7,7); 8,789 (5,7); 8,777 (5,9); 8,756 (8,6); 8,751 (9,3); 8,563 (1,5); 8,500 δ = 9.399 (16.0); 9,307 (7.2); 9,303 (7,7); 8,789 (5.7); 8,777 (5.9); 8,756 (8,6); 8,751 (9.3); 8.563 (1.5); 8,500
31 1,63 (4,6); 8,480 (4,8); 8,314 (14,3); 8,298 (7,3); 8,276 (8,7); 31 1.63 (4.6); 8,480 (4.8); 8,314 (14,3); 8,298 (7.3); 8,276 (8,7);
8,114 (5,2); 8,108 (5,5); 8,091 (4,3); 8,086 (4,5); 7,982 (1,4); 7,661 (3,9); 7,649 (4,2); 7,641 (4,3); 7,629 (3,9); 3,325 (105,2); 2,673 (1,2); 2,503 (173,0); 2,330 (1,1); 0,146 (0,7); 0,000 (124,7); -0,150 (0,7)  8.114 (5.2); 8,108 (5.5); 8,091 (4.3); 8,086 (4,5); 7,982 (1.4); 7,661 (3.9); 7,649 (4.2); 7,641 (4.3); 7,629 (3.9); 3,325 (105.2); 2,673 (1.2); 2,503 (173,0); 2.330 (1.1); 0.146 (0.7); 0.000 (124.7); -0.150 (0.7)
'H-NMR (399,9 MHz, de-DMSO):  'H-NMR (399.9 MHz, de-DMSO):
δ = 9,290 (0,6); 9,289 (0,6); 9,285 (0,6); 9,086 (0,3); 8,780 (0,5); 8,776 (0,5); 8,768 (0,5); 8,764 (0,5); 8,703 (0,8); 8,700 (0,8); 8,478 (0,3); 8,473 (0,4); 8,468 (0,3); 8,458 (0,3); 8,453 (0,4); 8,452 (0,4); 8,448 (0,3); 8,192 δ = 9.290 (0.6); 9,289 (0.6); 9.285 (0.6); 9.086 (0.3); 8,780 (0.5); 8.776 (0.5); 8.768 (0.5); 8.764 (0.5); 8,703 (0.8); 8,700 (0.8); 8.478 (0.3); 8.473 (0.4); 8.468 (0.3); 8.458 (0.3); 8.453 (0.4); 8.452 (0.4); 8.448 (0.3); 8,192
32 1,96 (0,6); 8,171 (0,8); 8,077 (0,6); 8,072 (0,6); 8,055 (0,4); 32 1.96 (0.6); 8,171 (0.8); 8.077 (0.6); 8,072 (0.6); 8.055 (0.4);
8,051 (0,4); 7,637 (0,4); 7,635 (0,3); 7,625 (0,4); 7,623 (0,3); 7,617 (0,3); 7,615 (0,3); 7,605 (0,3); 7,603 (0,3); 4,156 (0,5); 4,140 (0,5); 4,132 (0,5); 4,116 (0,5); 3,133 (16,0); 2,502 (1,0); 2,498 (1,8); 2,493 (2,5); 2,489 (1,8); 2,484 (0,9); 0,000 (0,8)  8,051 (0.4); 7.637 (0.4); 7.635 (0.3); 7.625 (0.4); 7.623 (0.3); 7.617 (0.3); 7.615 (0.3); 7.605 (0.3); 7.603 (0.3); 4.156 (0.5); 4.140 (0.5); 4,132 (0.5); 4.116 (0.5); 3.133 (16.0); 2,502 (1.0); 2,498 (1.8); 2,493 (2.5); 2.489 (1.8); 2.484 (0.9); 0,000 (0.8)
'H-NMR (399,9 MHz, de-DMSO):  'H-NMR (399.9 MHz, de-DMSO):
δ = 9,291 (3,4); 9,289 (3,5); 9,285 (3,6); 9,283 (3,3); 9,085 (0,9); 9,071 (1,5); 9,057 (0,9); 8,777 (2,9); 8,773 δ = 9.291 (3.4); 9,289 (3,5); 9.285 (3.6); 9.283 (3.3); 9.085 (0.9); 9.071 (1.5); 9.057 (0.9); 8,777 (2.9); 8,773
33 1,15 (3,1); 8,765 (3,1); 8,761 (3,0); 8,723 (4,6); 8,720 (4,6); 33 1.15 (3.1); 8,765 (3.1); 8,761 (3.0); 8,723 (4,6); 8,720 (4,6);
8,653 (0,2); 8,642 (0,2); 8,530 (2,2); 8,528 (2,4); 8,526 (2,3); 8,520 (2,4); 8,518 (2,5); 8,475 (4,9); 8,471 (5,9); 8,466 (4,1); 8,461 (4,0); 8,456 (4,1); 8,451 (2,9); 8,450 (2,7); 8,446 (2,1); 8,182 (3,1); 8,161 (5,7); 8,115 (3,8); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 8.653 (0.2); 8.642 (0.2); 8.530 (2.2); 8.528 (2.4); 8.526 (2.3); 8.520 (2.4); 8.518 (2.5); 8.475 (4.9); 8,471 (5.9); 8,466 (4,1); 8.461 (4.0); 8,456 (4,1); 8.451 (2.9); 8,450 (2.7); 8.446 (2.1); 8,182 (3,1); 8,161 (5,7); 8,115 (3,8); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
8,111 (3,7); 8,094 (2,1); 8,089 (2,1); 8,009 (0,2); 7,989 (0,3); 7,863 (0,2); 7,792 (0,2); 7,787 (0,2); 7,777 (1,5); 7,772 (1,7); 7,757 (2,9); 7,753 (2,9); 7,738 (2,0); 7,733 (2,4); 7,731 (2,6); 7,727 (2,4); 7,712 (4,4); 7,707 (4,4); 7,693 (2,7); 7,688 (2,6); 7,651 (0,2); 7,634 (2,2); 7,632 (2,1); 7,622 (2,2); 7,620 (2,1); 7,614 (2,2); 7,613 (2,1); 7,602 (2,1); 7,600 (2,0); 7,469 (0,2); 7,466 (0,2); 7,457 (0,2); 7,454 (0,2); 7,450 (0,3); 7,447 (0,3); 7,438 (0,4); 7,407 (5,9); 7,387 (5,2); 7,324 (0,2); 7,275 (1,8); 7,263 (1,8); 7,261 (1,8); 7,257 (1,8); 7,244 (1,6); 7,220 (0,3); 7,203 (2,7); 7,190 (2,8); 7,185 (2,7); 7,172 (2,3); 4,941 (0,7); 4,938 (0,6); 4,649 (6,6); 4,635 (6,5); 4,581 (0,2); 3,892 (0,3); 3,859 (0,4); 3,811 (16,0); 3,400 (0,3); 3,383 (0,3); 3,374 (0,3); 3,368 (0,3); 3,321 (0,3); 3,264 (0,6); 3,188 (1,0); 3,019 (4,2); 2,737 (0,5); 2,671 (0,4); 2,667 (0,4); 2,662 (0,4); 2,657 (0,4); 2,626 (0,3); 2,580 (0,3); 2,571 (0,3); 2,561 (0,3); 2,531 (1,2); 2,502 (7,0); 2,498 (13,3); 2,493 (17,9); 2,488 (12,6); 2,484 (6,2); 1,977 (0,6); 1,940 (0,2); 1,928 (0,2); 1,264 (0,2); 1,241 (0,5); 1,179 (0,3); 1,161 (0,3); 0,008 (0,3); 0,000 (4,7) 8,111 (3,7); 8.094 (2.1); 8,089 (2.1); 8.009 (0.2); 7.989 (0.3); 7.863 (0.2); 7,792 (0.2); 7.787 (0.2); 7,777 (1.5); 7,772 (1.7); 7,757 (2.9); 7,753 (2.9); 7,738 (2.0); 7.733 (2.4); 7,731 (2.6); 7,727 (2,4); 7,712 (4.4); 7,707 (4.4); 7,693 (2.7); 7,688 (2.6); 7.651 (0.2); 7.634 (2.2); 7,632 (2,1); 7.622 (2.2); 7,620 (2,1); 7.614 (2.2); 7.613 (2.1); 7.602 (2.1); 7,600 (2.0); 7.469 (0.2); 7.466 (0.2); 7.457 (0.2); 7.454 (0.2); 7,450 (0.3); 7.447 (0.3); 7.438 (0.4); 7,407 (5.9); 7,387 (5.2); 7,324 (0.2); 7.275 (1.8); 7.263 (1.8); 7.261 (1.8); 7.257 (1.8); 7.244 (1.6); 7.220 (0.3); 7,203 (2,7); 7,190 (2.8); 7.185 (2.7); 7,172 (2,3); 4,941 (0.7); 4,938 (0.6); 4,649 (6.6); 4,635 (6.5); 4,581 (0.2); 3,892 (0.3); 3.859 (0.4); 3,811 (16.0); 3,400 (0.3); 3.383 (0.3); 3,374 (0.3); 3,368 (0.3); 3,321 (0.3); 3,264 (0.6); 3.188 (1.0); 3,019 (4.2); 2,737 (0.5); 2,671 (0.4); 2,667 (0.4); 2,662 (0.4); 2,657 (0.4); 2,626 (0.3); 2,580 (0.3); 2,571 (0.3); 2.561 (0.3); 2.531 (1.2); 2,502 (7.0); 2,498 (13.3); 2,493 (17.9); 2,488 (12,6); 2,484 (6.2); 1,977 (0.6); 1,940 (0.2); 1.928 (0.2); 1,264 (0.2); 1,241 (0.5); 1.179 (0.3); 1.161 (0.3); 0.008 (0.3); 0,000 (4,7)
34 4,69 4,74 'Η-ΝΜΚ^ΟΟ,Ο MHZ, de-DMSO): 34 4,69 4,74 'Η-ΝΜΚ ^ ΟΟ, Ο MHZ, de-DMSO):
δ = 9,308(3,1); 9,304(3,2); 8,779(2,4);  δ = 9.308 (3.1); 9.304 (3.2); 8,779 (2.4);
8,767(2,4); 8,567(4,9); 8,563(5,0) 8,504(1,5) 8,767 (2.4); 8,567 (4.9); 8.563 (5.0) 8.504 (1.5)
8,499(2,2); 8,494(1,6); 8,484(1,7) 8,478(2,3)8,499 (2.2); 8,494 (1.6); 8.484 (1.7) 8.478 (2.3)
8,474(1,7); 8,189(4,2); 8,168(4,9) 7,912(2,9)8.474 (1.7); 8,189 (4.2); 8.168 (4.9) 7.912 (2.9)
7,908(3,0); 7,891(2,5); 7,886(2,7) 7,684(5,0)7.908 (3.0); 7,891 (2.5); 7,886 (2,7) 7,684 (5,0)
7,680(3,2); 7,654(2,0); 7,642(2,1) 7,634(2,0)7,680 (3.2); 7,654 (2.0); 7.642 (2.1) 7.634 (2.0)
7,622(2,0); 7,604(2,1); 7,584(2,8) 7,530(0,4)7,622 (2.0); 7,604 (2.1); 7,584 (2,8) 7,530 (0,4)
7,480(2,3); 7,460(4,6); 7,441(2,6) 7,406(0,3)7,480 (2.3); 7,460 (4.6); 7.441 (2.6) 7.406 (0.3)
7,361(2,8); 7,342(2,0); 3,333(15,5); 3,123(2,4)7,361 (2.8); 7,342 (2.0); 3.333 (15.5); 3.123 (2.4)
3,105(7,7); 3,087(8,0); 3,068(3,1); 3,050(0,6)3,105 (7.7); 3.087 (8.0); 3,068 (3.1); 3,050 (0.6)
2,673(0,5); 2,669(0,4); 2,526(1,3); 2,508(57,7) 2,504(76,3); 2,499(57,4); 2,331(0,5); 2,326(0,4) 1,307(7,8); 1,289(16,0); 1,271(7,6); 1,264(1,6) 1,245(0,6); 0,008(1,6); 0,000(43,0); -0,008(2,1)2,673 (0.5); 2,669 (0.4); 2,526 (1.3); 2.508 (57.7) 2.504 (76.3); 2,499 (57.4); 2.331 (0.5); 2.326 (0.4) 1.307 (7.8); 1,289 (16.0); 1,271 (7.6); 1.264 (1.6) 1.245 (0.6); 0.008 (1.6); 0,000 (43.0); -0.008 (2.1)
35 2,26 2,32 'Η-ΝΜΚ^ΟΟ,Ο MHZ, de-DMSO): 35 2.26 2.32 'Η-ΝΜΚ ^ ΟΟ, Ο MHZ, de-DMSO):
δ = 9,316(4,5); 9,311(4,5); 8,787(3,1); 8,784(3,4) δ = 9.316 (4.5); 9,311 (4.5); 8,787 (3.1); 8.784 (3.4)
8,775(3,2); 8,772(3,3); 8,641(6,1); 8,637(6,2)8,775 (3.2); 8.772 (3.3); 8,641 (6.1); 8.637 (6.2)
8,512(1,8); 8,507(2,8); 8,503(1,9); 8,492(2,0)8,512 (1.8); 8.507 (2.8); 8,503 (1.9); 8.492 (2.0)
8,487(3,0); 8,483(1,9); 8,319(0,3); 8,228(5,1)8,487 (3.0); 8,483 (1.9); 8,319 (0.3); 8,228 (5.1)
8,207(6,0); 8,160(1,7); 8,025(6,1); 7,977(5,2)8,207 (6.0); 8,160 (1.7); 8,025 (6.1); 7.977 (5.2)
7,973(4,0); 7,963(3,6); 7,956(3,7); 7,951(3,2)7,973 (4.0); 7,963 (3.6); 7,956 (3.7); 7,951 (3.2)
7,750(2,0); 7,731(5,0); 7,712(3,7); 7,692(4,8)7,750 (2.0); 7,731 (5.0); 7,712 (3.7); 7,692 (4.8)
7,673(2,1); 7,659(2,7); 7,646(2,6); 7,639(2,6)7,673 (2.1); 7.659 (2.7); 7,646 (2.6); 7,639 (2.6)
7,627(2,5); 5,759(0,5); 3,334(19,2); 3,177(0,6)7.627 (2.5); 5,759 (0.5); 3,334 (19.2); 3,177 (0.6)
3,158(1,8); 3,140(2,2); 3,125(2,5); 3,106(2,3)3,158 (1.8); 3,140 (2.2); 3.125 (2.5); 3,106 (2.3)
3,088(0,7); 2,920(0,6); 2,902(2,2); 2,883(2,6)3,088 (0.7); 2,920 (0.6); 2,902 (2.2); 2,883 (2.6)
2,868(2,1); 2,849(1,8); 2,831(0,5); 2,673(1,0)2,868 (2.1); 2,849 (1.8); 2,831 (0.5); 2,673 (1.0)
2,508(119,1); 2,504(153,4); 2,500(117,1); 2,331(1,0)2,508 (119.1); 2.504 (153.4); 2,500 (117.1); 2.331 (1.0)
1,101(7,5); 1,083(16,0); 1,064(7,3); 0,007(2,1) 0,000(54,2); -0,007(2,8) Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 1,101 (7.5); 1.083 (16.0); 1.064 (7.3); 0.007 (2.1) 0.000 (54.2); -0.007 (2.8) Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
36 2,05 2,03 ^-NMR^OO.O MHZ, de-DMSO):  36 2.05 2.03 ^ -NMR ^ OO.O MHZ, de-DMSO):
= 9,278(2 ,2); 9,274(2,1); 9,272(2,1); 8,767(1,7) = 9,278 (2, 2); 9.274 (2.1); 9,272 (2.1); 8,767 (1.7)
,763(1,8) 8,755(1,8) 8,751(1,8) 8,589(2,8), 763 (1.8) 8.755 (1.8) 8.751 (1.8) 8.589 (2.8)
,586(2,8) 8,472(1,0) 8,468(1,2) 8,466(1,2), 586 (2.8) 8.472 (1.0) 8.468 (1.2) 8.466 (1.2)
,462(1,0) 8,452(1,1) 8,448(1,2) 8,446(1,3), 462 (1.0) 8.452 (1.1) 8.448 (1.2) 8.446 (1.3)
,442(1,0) 8,119(1,9) 8,097(3,2) 8,036(2,3), 442 (1.0) 8.119 (1.9) 8.097 (3.2) 8.036 (2.3)
,032(2,2) 8,015(1,4) 8,011(1,4) 7,794(3,0), 032 (2.2) 8.015 (1.4) 8.011 (1.4) 7.794 (3.0)
,788(3,0) 7,641(1,1) 7,640(1,2) 7,629(1,1), 788 (3.0) 7.641 (1.1) 7.640 (1.2) 7.629 (1.1)
,628(1,2) 7,621(1,1); 7,620(1,1) 7,609(1,1), 628 (1.2) 7.621 (1.1); 7.620 (1.1) 7.609 (1.1)
,608(1,1); 6,833(3,7); 6,827(3,7); 3,923(16,0), 608 (1.1); 6,833 (3.7); 6,827 (3.7); 3.923 (16.0)
,322(22,6) 2,526(0,5); 2,521(0,7); 2,512(11,0), 322 (22.6) 2.526 (0.5); 2,521 (0.7); 2.512 (11.0)
,508(23,5) 2,503(33,0): 2,499(24,5); 2,494(11,6), 508 (23.5) 2.503 (33.0): 2.499 (24.5); 2,494 (11.6)
,990(0,4); 1,071(1,9); 0,000(7,7) , 990 (0.4); 1,071 (1.9); 0.000 (7.7)
37 2,03 2,17 1H-NMR(400,0 MHz, de-DMSO): 37 2.03 2.17 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,278(2,7); 9,275(2,9); 8,764(1,7); 8,761(2,1) δ = 9.278 (2.7); 9,275 (2.9); 8.764 (1.7); 8.761 (2.1)
8,752(1,9) 8,749(2,2); 8,470(1,0); 8,466(1,5) 8,462(1,3) 8,450(1,1); 8,446(1,6); 8,442(1,4) 8,215(3,9) 8,124(2,7); 8,103(2,9); 7,698(5,4) 7,636(2,5) 7,631(2,6); 7,629(2,5); 7,619(1,7) 7,615(2,1) 7,610(2,9); 3,819(15,4); 3,325(88,4)8.752 (1.9) 8.749 (2.2); 8,470 (1.0); 8.466 (1.5) 8.462 (1.3) 8.450 (1.1); 8.446 (1.6); 8.442 (1.4) 8.215 (3.9) 8.124 (2.7); 8,103 (2.9); 7.698 (5.4) 7.636 (2.5) 7.631 (2.6); 7,629 (2.5); 7.619 (1.7) 7.615 (2.1) 7.610 (2.9); 3,819 (15.4); 3.325 (88.4)
2,507(36,2); 2,503(49,0); 2,500(43,1); 2,451(16,0) 0,000(33,7); -0,003(21,8) 2,507 (36.2); 2,503 (49.0); 2,500 (43.1); 2,451 (16.0) 0.000 (33.7); -0.003 (21.8)
38 2,4 2,54 1H-NMR(400,0 MHz, de-DMSO): 38 2.4 2.54 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,276(1 ,9); 9,270(1,8); 8,762(1,4); 8,758(1,5) 8,750(1,4) 8,746(1,5) 8,468(0,8); 8,463(1,1) 8,458(0,9) 8,447(3,0) 8,443(3,5); 8,438(1,1) 8,403(3,6) 8,103(2,1) 8,081(2,9); 8,078(4,0) 7,844(1,5) 7,839(1,5) 7,822(1,3); 7,818(1,3) 7,639(1,0) 7,637(1,1) 7,627(1,2); 7,625(1,3) 7,617(1,1) 7,607(1,0); 7,605(1,0); 5,755(0,4) 5,308(7,6) 3,318(43,5); 2,671(0,4); 2,525(0,9) 2,520(1,4); 2,511(23,1); 2,507(49,4); 2,502(66,9) 2,498(48,5) 2,493(23,2); 2,329(0,4); 2,190(16,0) 0,000(8,8)  δ = 9.276 (1, 9); 9,270 (1.8); 8.762 (1.4); 8.758 (1.5) 8.750 (1.4) 8.746 (1.5) 8.468 (0.8); 8.463 (1.1) 8.458 (0.9) 8.447 (3.0) 8.443 (3.5); 8.438 (1.1) 8.403 (3.6) 8.103 (2.1) 8.081 (2.9); 8.078 (4.0) 7.844 (1.5) 7.839 (1.5) 7.822 (1.3); 7.818 (1.3) 7.639 (1.0) 7.637 (1.1) 7.627 (1.2); 7.625 (1.3) 7.617 (1.1) 7.607 (1.0); 7,605 (1.0); 5.755 (0.4) 5.308 (7.6) 3.318 (43.5); 2,671 (0.4); 2.525 (0.9) 2.520 (1.4); 2,511 (23.1); 2,507 (49.4); 2.502 (66.9) 2.498 (48.5) 2.493 (23.2); 2,329 (0.4); 2,190 (16.0) 0.000 (8.8)
39 1,32 1,51 1H-NMR(400,0 MHz, de-DMSO): 39 1.32 1.51 1 H-NMR (400.0 MHz, de-DMSO):
= 9,278(2 :,2); 9,273(2,1); 8,763(1,6); 8,760(1,6) ,751(1,7) 8,748(1,6) 8,490(0,3) 8,480(2,8) ,476(2,9) 8,470(1,1) 8,465(1,3) 8,460(0,9) ,450(1,1) 8,445(1,4) 8,440(1,0) 8,421(0,4) ,335(4,3) 8,250(0,4) 8,218(4,5) 8,114(2,4) ,105(0,4) 8,093(2,9) 7,865(1,8) 7,861(1,7) ,844(1,5) 7,840(1,5) 7,639(1,2) 7,627(1,3) ,619(1,2) 7,608(1,2) 5,803(0,5) 5,569(2,0) ,536(2,6) 5,348(2,7); 5,315(2,1) 3,322(7,5) ,078(1,1); 2,672(0,3); 2,595(16,0); 2,525(0,7) ,512(19,6) 2,507(41,7); 2,503(56,5); 2,498(41,0) ,494(19,7) 0,146(0,4); 0 ,008(2,9); 0, 000(82,7); ■ ,009(2,9);■0,150(0,4) = 9,278 (2:, 2); 9.273 (2.1); 8.763 (1.6); 8.760 (1.6), 751 (1.7) 8.748 (1.6) 8.490 (0.3) 8.480 (2.8), 476 (2.9) 8.470 (1.1) 8.465 (1.3) 8.460 (0.9), 450 (1.1) 8.445 (1.4) 8.440 (1.0) 8.421 (0.4), 335 (4.3) 8.250 (0.4) 8.218 (4.5) 8.114 (2.4), 105 (0.4) 8.093 (2.9) 7.865 (1.8) 7.861 (1.7), 844 (1.5) 7.840 (1.5) 7.639 (1.2) 7.627 (1.3), 619 (1.2) 7.608 (1.2) 5.803 (0.5) 5.559 (2.0), 536 (2.6) 5.348 (2.7); 5.315 (2.1) 3.322 (7.5), 078 (1.1); 2,672 (0.3); 2,595 (16.0); 2.525 (0.7), 512 (19.6) 2.507 (41.7); 2,503 (56.5); 2,498 (41.0), 494 (19.7) 0.146 (0.4); 0, 008 (2.9); 0, 000 (82.7); ■ , 009 (2.9); ■ 0.150 (0.4)
40 1,41 1,49 1H-NMR(400,0 MHz, de-DMSO): 40 1.41 1.49 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,317(10,0); 9,313(9,7); 8,799(6,8); 8,795(7,0); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] δ = 9.317 (10.0); 9.313 (9.7); 8.799 (6.8); 8.795 (7.0); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
8,787(7,3); 8,602(16,0); 8,598(15,3); 8,516(5,3) 8,787 (7.3); 8,602 (16.0); 8,598 (15.3); 8,516 (5.3)
8,512(6,8); 8,507(4,7); 8,496(5,7); 8,492(7,0)8,512 (6.8); 8.507 (4.7); 8,496 (5.7); 8.492 (7.0)
8,487(4,9); 8,248(12,9); 8,227(14,8); 7,901(10,7)8,487 (4.9); 8,248 (12.9); 8,227 (14.8); 7.901 (10.7)
7,897(9,7); 7,880(9,6); 7,876(9,1); 7,665(6,1)7,897 (9.7); 7,880 (9.6); 7,876 (9.1); 7.665 (6.1)
7,652(6,0); 7,645(6,0); 7,633(5,8); 5,757(0,8)7,652 (6.0); 7,645 (6.0); 7,633 (5.8); 5,757 (0.8)
3,616(0,5); 3,548(0,6); 3,444(93,9); 3,374(96,7)3,616 (0.5); 3,548 (0.6); 3,444 (93.9); 3,374 (96.7)
3,319(208,6) 3,288(0,5); 3,266(0,5); 3,194(0,5)3.329 (208.6) 3.288 (0.5); 3,266 (0.5); 3,194 (0.5)
2,672(2,0); 2,667(1,4); 2,511(116,8); 2,507(232,1)2,672 (2.0); 2,667 (1.4); 2,511 (116.8); 2.507 (232.1)
2,502(309,3) 2,498(228,0); 2,493(107,3); 2,333(1,5)2.502 (309.3) 2.498 (228.0); 2,493 (107.3); 2.333 (1.5)
2,329(1,8); 2,325(1,2); 1,989(0,7); 1,337(0,3)2,329 (1.8); 2,325 (1.2); 1,989 (0.7); 1.337 (0.3)
1,298(1,1); 1,259(1,6); 1,250(0,9); 1,233(3,2)1.298 (1.1); 1,259 (1.6); 1,250 (0.9); 1.233 (3.2)
1,175(0,6); 0,853(0,5); 0,834(0,4); 0,146(1,2)1.175 (0.6); 0.853 (0.5); 0.834 (0.4); 0.146 (1.2)
0,008(11,3); 0,000(269,6); -0,009(9,7); -0,150(1,1)0.008 (11.3); 0.000 (269.6); -0.009 (9.7); -0.150 (1.1)
41 1,66 1,8 1H-NMR(400,0 MHz, de-DMSO): 41 1.66 1.8 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,317(4 ,3); 9,312(4,7); 8,798(2,9); 8,795(3,4) δ = 9.317 (4, 3); 9,312 (4.7); 8,798 (2.9); 8.795 (3.4)
8,786(3,0) 8,783(3,3); 8,605(5,3) 8,602(5,8)8.786 (3.0) 8.783 (3.3); 8.605 (5.3) 8.602 (5.8)
8,516(1,5) 8,511(2,5); 8,507(1,9) 8,496(1,7)8.516 (1.5) 8.511 (2.5); 8,507 (1,9) 8,496 (1,7)
8,491(2,6) 8,487(1,9); 8,247(4,4) 8,226(5,0)8.491 (2.6) 8.487 (1.9); 8.247 (4.4) 8.226 (5.0)
7,911(3,1) 7,907(3,5); 7,890(2,7) 7,886(3,1)7.911 (3.1) 7.907 (3.5); 7,890 (2,7) 7,886 (3,1)
7,663(2,3) 7,651(2,4); 7,644(2,6) 7,631(2,5)7.663 (2.3) 7.651 (2.4); 7.644 (2.6) 7.631 (2.5)
7,617(0,5) 7,599(0,6); 7,576(0,4) 7,568(0,5)7.617 (0.5) 7.599 (0.6); 7,576 (0,4) 7,568 (0,5)
7,558(0,4) 7,549(0,4); 5,758(2,4) 3,859(2,2)7,558 (0.4) 7.549 (0.4); 5.758 (2.4) 3.859 (2.2)
3,841(7,0); 3,823(7,1); 3,805(2,3); 3,378(32,2)3,841 (7.0); 3,823 (7.1); 3.805 (2.3); 3,378 (32.2)
3,321(46,9) 3,158(0,4); 2,673(0,4); 2,508(55,1)3.321 (46.9) 3.158 (0.4); 2,673 (0.4); 2.508 (55.1)
2,504(73,1) 2,499(54,5); 2,330(0,4); 1,307(7,5)2,504 (73.1) 2,499 (54.5); 2,330 (0.4); 1.307 (7.5)
1,289(16,0) 1,271(7,4); 0,000(1,4) 1.289 (16.0) 1.271 (7.4); 0.000 (1.4)
42 2,08 2,14 1H-NMR(400,0 MHz, de-DMSO): 42 2.08 2.14 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,325(2,1); 8,803(1,7); 8,796(1,7); 8,631(6,5) δ = 9.325 (2.1); 8.803 (1.7); 8,796 (1.7); 8.631 (6.5)
8,627(6,7) 8,522(1,8) 8,518(2,6) 8,513(1,8) 8,502(1,9) 8,498(2,8) 8,493(1,8) 8,271(5,5) 8,250(6,3) 7,918(3,7) 7,914(3,6) 7,896(3,3) 7,892(3,3) 7,668(2,1) 7,656(2,2) 7,648(2,3) 7,636(2,1) 5,756(0,7); 4,780(1,7) 4,757(5,5) 4,734(5,8). 4,712(2,0); 3,404(35,0); 3,325(60,0) 2,673(0,4). 2,526(0,9); 2,509(51,2); 2,504(67,6) 2,500(49,0); 2,332(0,4); 2,076(16,0); 1,160(0,8)8.627 (6.7) 8.522 (1.8) 8.518 (2.6) 8.513 (1.8) 8.502 (1.9) 8.498 (2.8) 8.493 (1.8) 8.271 (5.5) 8.250 ( 6.3) 7.918 (3.7) 7.914 (3.6) 7.896 (3.3) 7.892 (3.3) 7.668 (2.1) 7.656 (2.2) 7.648 (2.3) 7.636 (2, 1) 5,756 (0.7); 4,780 (1.7) 4,757 (5.5) 4,734 (5.8). 4,712 (2.0); 3,404 (35.0); 3,325 (60.0) 2,673 (0.4). 2,526 (0.9); 2,509 (51.2); 2,504 (67.6) 2,500 (49.0); 2,332 (0.4); 2,076 (16.0); 1.160 (0.8)
1,071(0,5); 0,000(6,6) 1,071 (0.5); 0.000 (6.6)
43 1,34 1,51 I 'Η-ΝΜΪ^όΟΟ,Ι MHz, de-DMSO):  43 1.34 1.51 I'Η-ΝΜΪ ^ όΟΟ, Ι MHz, de-DMSO):
δ = 9,350(1,6); 9,349(1,7); 9,346(1,7); 9,345(1,6) δ = 9.350 (1.6); 9.349 (1.7); 9,346 (1.7); 9,345 (1.6)
8,810(1,5); 8,807(1,6) 8,802(1,6) 8,799(1,6)8,810 (1.5); 8,807 (1.6) 8,802 (1.6) 8,799 (1.6)
8,653(2,3); 8,652(2,4) 8,650(2,4) 8,649(2,2)8.653 (2.3); 8.652 (2.4) 8.650 (2.4) 8.649 (2.2)
8,622(3,8); 8,539(1,0) 8,536(1,2) 8,535(1,1)8.622 (3.8); 8.539 (1.0) 8.536 (1.2) 8.535 (1.1)
8,533(1,0); 8,526(1,0) 8,523(1,2) 8,522(1,2)8,533 (1.0); 8.526 (1.0) 8.523 (1.2) 8.522 (1.2)
8,519(1,0); 8,358(4,8) 8,182(2,2) 8,181(2,1)8,519 (1.0); 8,358 (4,8) 8,182 (2,2) 8,181 (2,1)
8,168(2,6); 8,167(2,5) 8,034(2,3) 8,031(2,6)8,168 (2.6); 8.167 (2.5) 8.034 (2.3) 8.031 (2.6)
8,026(5,2); 8,020(2,3) 8,017(2,0) 7,683(1,1)8.026 (5.2); 8.020 (2.3) 8.017 (2.0) 7.683 (1.1)
7,682(1,1); 7,675(1,1); 7,674(1,1) 7,670(1,1)7,682 (1.1); 7,675 (1.1); 7.674 (1.1) 7.670 (1.1)
7,669(1,1); 7,662(1,1); 7,661(1,1); 3,651(16,0)7.669 (1.1); 7,662 (1.1); 7,661 (1.1); 3.651 (16.0)
3,483(55,0); 3,468(0,6); 2,923(3,1); 2,919(6,6)3,483 (55.0); 3,468 (0.6); 2,923 (3.1); 2,919 (6.6)
2,916(9,5); 2,913(6,7); 2,910(3,2); 2,752(3,6)2,916 (9.5); 2,913 (6.7); 2,910 (3.2); 2,752 (3.6)
2,749(7,4); 2,745(10,8); 2,742(7,5); 2,739(3,8) Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 2,749 (7.4); 2,745 (10.8); 2,742 (7.5); 2,739 (3.8) Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
1,155(1,0); 0,000(4,0)  1,155 (1.0); 0.000 (4.0)
44 1,63 1,72 I 1H-NMR(400,0 MHz, de-DMSO): 44 1.63 1.72 I 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,285(6,1); 9,281(6,2); 8,771(4,2); 8,767(4,7) δ = 9.285 (6.1); 9,281 (6.2); 8,771 (4.2); 8,767 (4.7)
8,759(4,5); 8,755(4,6); 8,480(2,5); 8,476(3,6)8.759 (4.5); 8,755 (4.6); 8,480 (2.5); 8,476 (3.6)
8,470(2,6); 8,460(2,8); 8,455(3,7); 8,450(2,7)8,470 (2.6); 8,460 (2.8); 8.455 (3.7); 8,450 (2.7)
8,402(8,1); 8,398(8,6); 8,187(16,0); 8,130(7,1)8,402 (8.1); 8.398 (8.6); 8,187 (16.0); 8,130 (7.1)
8,109(8,1); 7,805(5,1); 7,801(5,1); 7,784(4,6)8,109 (8.1); 7,805 (5.1); 7,801 (5.1); 7,784 (4.6)
7,780(4,7); 7,644(3,4); 7,631(3,4); 7,624(3,5)7,780 (4.7); 7.644 (3.4); 7,631 (3.4); 7.624 (3.5)
7,612(3,3); 7,598(0,4); 3,458(0,4); 3,430(46,4)7.612 (3.3); 7.598 (0.4); 3,458 (0.4); 3,430 (46.4)
3,392(0,4); 3,327(344,1); 3,283(47,8); 3,251(0,3)3,392 (0.4); 3.327 (344.1); 3,283 (47.8); 3,251 (0.3)
2,676(0,6); 2,672(0,9); 2,668(0,7); 2,525(2,1) 2,512(47,9); 2,507(101,7); 2,503(143,0); 2,498(109,0)2,676 (0.6); 2,672 (0.9); 2,668 (0.7); 2.525 (2.1) 2.512 (47.9); 2.507 (101.7); 2.503 (143.0); 2.498 (109.0)
2,494(54,2); 2,334(0,6); 2,329(0,9); 2,325(0,6) 0,008(1,2); 0,000(38,3); -0,009(1,4) 2,494 (54.2); 2,334 (0.6); 2,329 (0.9); 2.325 (0.6) 0.008 (1.2); 0,000 (38.3); -0.009 (1.4)
45 2,62 2,71 1H-NMR(400,0 MHz, de-DMSO): 45 2.62 2.71 1 H-NMR (400.0 MHz, de-DMSO):
= 9,279(3 ,0); 9,275(3,1); 9,273(2,9); 8,772(2,3) ,768(2,5) 8,760(2,5) ; 8,756(2,5) 8,618(4,0) ,613(4,1) 8,475(1,3) ; 8,471(1,8) 8,465(1,4) ,455(1,5) 8,451(1,8) ; 8,449(1,9) 8,445(1,4) ,375(4,7) 8,195(3,4) ; 8,173(4,5) 8,046(2,8) ,041(2,7) 8,024(2,1) ; 8,018(2,1) 7,647(1,8) ,645(1,8) 7,636(6,9);; 7,627(1,8) 7,625(1,7) ,615(1,6) 7,613(1,6); 3,319(102,4); 2,676(0,5) ,671(0,7); 2,667(0,5); 2,525(1,6); 2,520(2,5) ,511(38,4) 2,507(80,5); 2,502(107,8); 2,498(78,1) ,493(37,7) 2,334(0,5); 2,329(0,6); 2,324(0,5) ,136(16,0) 0,146(0,4); 0,008(3,1); 0,000(96,8); ■ ,009(3,6); 0,150(0,4) = 9,279 (3, 0); 9,275 (3.1); 9.273 (2.9); 8.772 (2.3), 768 (2.5) 8.760 (2.5); 8.756 (2.5) 8.618 (4.0), 613 (4.1) 8.475 (1.3); 8.471 (1.8) 8.465 (1.4), 455 (1.5) 8.451 (1.8); 8.449 (1.9) 8.445 (1.4), 375 (4.7) 8.195 (3.4); 8.173 (4.5) 8.046 (2.8), 041 (2.7) 8.024 (2.1); 8.018 (2.1) 7.647 (1.8), 645 (1.8) 7.636 (6.9); 7.627 (1.8) 7.625 (1.7), 615 (1.6) 7.613 (1.6); 3.319 (102.4); 2,676 (0.5), 671 (0.7); 2,667 (0.5); 2,525 (1.6); 2.520 (2.5), 511 (38.4) 2.507 (80.5); 2.502 (107.8); 2.498 (78.1), 493 (37.7) 2.334 (0.5); 2,329 (0.6); 2.324 (0.5), 136 (16.0) 0.146 (0.4); 0.008 (3.1); 0,000 (96.8); ■ , 009 (3,6); 0.150 (0.4)
46 1,35 1,49 1H-NMR(400, 0 MHz, de-DMSO): 46 1.35 1.49 1 H-NMR (400, 0 MHz, de-DMSO):
δ = 9,257(1,5) 9,253(1,5); 8,772(5,7); 8,759(1,1) δ = 9,257 (1.5) 9,253 (1.5); 8.772 (5.7); 8.759 (1.1)
8,756(1,1); 8,453(0,9); 8,449(1,1) 8,443(0,9)8,756 (1.1); 8,453 (0.9); 8.449 (1.1) 8.443 (0.9)
8,433(1,0); 8,428(1,2); 8,423(0,9) 8,167(2,6)8.433 (1.0); 8,428 (1.2); 8.423 (0.9) 8.167 (2.6)
8,163(2,6); 8,095(2,6); 8,074(2,7) 7,635(1,0)8.163 (2.6); 8,095 (2.6); 8.074 (2.7) 7.635 (1.0)
7,633(1,0); 7,623(1,0); 7,621(1,0) 7,615(1,0)7,633 (1.0); 7,623 (1.0); 7.621 (1.0) 7.615 (1.0)
7,613(1,0); 7,603(1,0); 7,601(0,9) 7,460(1,8)7,613 (1.0); 7,603 (1.0); 7.601 (0.9) 7.460 (1.8)
7,455(1,7); 7,438(1,7); 7,434(1,6); 3,631(16,0)7.455 (1.7); 7,438 (1.7); 7,434 (1.6); 3.631 (16.0)
3,330(3,7); 2,515(5,9); 2,511(12,0); 2,506(15,9) 2,502(11,5); 2,497(5,6); 0,000(4,1) 3,330 (3.7); 2,515 (5.9); 2,511 (12.0); 2.506 (15.9) 2.502 (11.5); 2,497 (5.6); 0.000 (4.1)
47 1,52 1,63 1H-NMR(400,0 MHz, de-DMSO): 47 1.52 1.63 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,286(1,4); 9,282(1,5); 8,780(1,0); 8,777(1,0) δ = 9.286 (1.4); 9,282 (1.5); 8,780 (1.0); 8.777 (1.0)
8,768(1,1) 8,765(1,0); 8,485(0,8); 8,480(1,1) 8,475(0,9) 8,465(0,9); 8,459(1,2); 8,455(0,9) 8,252(2,7) 8,247(2,7); 8,216(2,5); 8,194(2,7) 7,649(1,0) 7,635(2,4); 7,630(2,6); 7,616(1,1) 7,613(1,8) 7,608(1,7); 5,753(0,5); 3,331(17,5) 3,269(0,5). 3,094(16,0); 3,026(15,0); 2,564(0,5) 2,526(0,6); 2,513(12,2); 2,508(25,1); 2,504(33,3)8.768 (1.1) 8.765 (1.0); 8,485 (0.8); 8.480 (1.1) 8.475 (0.9) 8.465 (0.9); 8.459 (1.2); 8.455 (0.9) 8.252 (2.7) 8.247 (2.7); 8,216 (2.5); 8.194 (2.7) 7.649 (1.0) 7.635 (2.4); 7,630 (2.6); 7.616 (1.1) 7.613 (1.8) 7.608 (1.7); 5,753 (0.5); 3.331 (17.5) 3.269 (0.5). 3,094 (16.0); 3,026 (15.0); 2.564 (0.5) 2.526 (0.6); 2,513 (12.2); 2,508 (25.1); 2,504 (33.3)
2,499(24,3); 2,495(11,9); 0,000(6,1) 2,499 (24.3); 2,495 (11.9); 0.000 (6.1)
48 1,66 1,81 1H-NMR(400,0 MHz, de-DMSO): 48 1.66 1.81 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,266(0,4); 8,767(0,4); 8,661(1,9); 8,658(2,9); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] δ = 9.266 (0.4); 8,767 (0.4); 8.661 (1.9); 8.658 (2.9); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
8,655(2,1); 8,446(1,0); 8,426(1,0); 8,168(4,0); 8,164(6,6); 7,638(0,7); 7,627(0,7); 7,618(0,7); 7,607(0,6); 3,322(19,4); 3,319(18,0); 3,239(15,8); 2,525(0,5); 2,512(13,3); 2,508(28,2); 2,503(38,1); 2,498(27,5); 2,494(13,2); 2,319(16,0); 0,008(1,2); 8.655 (2.1); 8.446 (1.0); 8,426 (1.0); 8,168 (4.0); 8,164 (6.6); 7.638 (0.7); 7.627 (0.7); 7,618 (0.7); 7,607 (0.6); 3,322 (19.4); 3,319 (18.0); 3,239 (15.8); 2,525 (0.5); 2,512 (13.3); 2,508 (28.2); 2,503 (38.1); 2,498 (27.5); 2,494 (13.2); 2,319 (16.0); 0.008 (1.2);
0,000(39,7); -0,009(1,3) 0,000 (39.7); -0.009 (1.3)
49 1,41 1,58 1H-NMR(400,0 MHz, de-DMSO): 49 1.41 1.58 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,257(1 ,5); 9,252(1,5); 8,770(1,0) 8,766(1,1) 8,758(1,1) 8,754(1,1). 8,455(0,8) 8,450(1,0) 8,445(0,8) 8,435(0,9). 8,429(1,1) 8,425(0,8). 8,125(2,4) 8,120(2,4). 8,089(2,3) 8,068(2,4). 7,636(0,9) 7,634(0,9). 7,624(0,9) 7,622(0,9). 7,616(0,9) 7,614(0,9) 7,604(0,9) 7,602(0,8). 7,446(1,6) 7,441(1,5); 7,425(1,5) 7,420(1,5). 5,755(1,5). 3,518(16,0); 3,320(45,9); 2,675(0,4). 2,671(0,5); 2,666(0,4); 2,524(1,3); 2,511(30,6) 2,506(64,7) 2,502(87,3); 2,497(62,6); 2,493(29,8). 2,417(15,7) 2,333(0,4); 2,329(0,5); 2,324(0,4). 0,000(9,6);■0,008(0,4)  δ = 9,257 (1, 5); 9,252 (1.5); 8.770 (1.0) 8.766 (1.1) 8.758 (1.1) 8.754 (1.1). 8.455 (0.8) 8.450 (1.0) 8.445 (0.8) 8.435 (0.9). 8.429 (1.1) 8.425 (0.8). 8.125 (2.4) 8.120 (2.4). 8.089 (2.3) 8.068 (2.4). 7.636 (0.9) 7.634 (0.9). 7.624 (0.9) 7.622 (0.9). 7.616 (0.9) 7.614 (0.9) 7.604 (0.9) 7.602 (0.8). 7.446 (1.6) 7.441 (1.5); 7.425 (1.5) 7.420 (1.5). 5,755 (1.5). 3,518 (16.0); 3,320 (45.9); 2,675 (0.4). 2,671 (0.5); 2,666 (0.4); 2,524 (1.3); 2.511 (30.6) 2.506 (64.7) 2.502 (87.3); 2,497 (62.6); 2,493 (29.8). 2.417 (15.7) 2.333 (0.4); 2,329 (0.5); 2,324 (0.4). 0,000 (9.6); ■ 0.008 (0.4)
50 2,09 2,21 I 1H-NMR(400,0 MHz, de-DMSO): 50 2.09 2.21 I 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,260(1,6); 9,255(1,6); 8,761(1,1); 8,757(1,2). δ = 9.260 (1.6); 9,255 (1.6); 8.761 (1.1); 8.757 (1.2).
8,749(1,1); 8,745(1,1); 8,599(2,0); 8,596(1,9).8.749 (1.1); 8,745 (1.1); 8,599 (2.0); 8.596 (1.9).
8,451(0,7); 8,447(1,0); 8,442(0,7); 8,431(0,8).8.451 (0.7); 8,447 (1.0); 8.442 (0.7); 8,431 (0.8).
8,426(1,1); 8,422(0,7); 8,313(0,6); 8,194(0,4).8,426 (1.1); 8,422 (0.7); 8,313 (0.6); 8.194 (0.4).
8,182(0,5); 8,160(3,3); 8,155(2,7); 8,150(2,4).8,182 (0.5); 8,160 (3.3); 8.155 (2.7); 8,150 (2.4).
8,132(0,4); 8,127(0,5); 7,636(1,2); 7,624(0,9).8,132 (0.4); 8,127 (0.5); 7,636 (1.2); 7,624 (0.9).
7,617(1,0); 7,606(0,9); 4,086(16,0); 3,315(99,7)7,617 (1.0); 7,606 (0.9); 4,086 (16.0); 3.315 (99.7)
3,135(14,1); 3,092(2,0); 3,052(0,5); 3,024(1,9).3.135 (14.1); 3,092 (2.0); 3,052 (0.5); 3.024 (1.9).
2,679(0,5); 2,675(1,0); 2,670(1,3); 2,666(1,0).2,679 (0.5); 2,675 (1.0); 2,670 (1.3); 2.666 (1.0).
2,661(0,4); 2,524(2,9); 2,519(4,4); 2,510(76,7).2,661 (0.4); 2,524 (2.9); 2,519 (4.4); 2.510 (76.7).
2,506(164,5); 2,501(222,7); 2,497(159,4); 2,492(75,6).2.506 (164.5); 2.501 (222.7); 2.497 (159.4); 2.492 (75.6).
2,333(0,9); 2,328(1,3); 2,324(0,9); 2,319(0,5). 0,008(1,6); 0,000(54,6); -0,009(1,9) 2,333 (0.9); 2,328 (1.3); 2,324 (0.9); 2,319 (0.5). 0.008 (1.6); 0,000 (54.6); -0.009 (1.9)
51 2,43 2,56 1H-NMR(400, 0 MHz, de-DMSO): 51 2.43 2.56 1 H-NMR (400, 0 MHz, de-DMSO):
δ = 9,263(1,6) 9,258(1,6); 8,763(1,0); 8,760(1,2); 8,751(1,1) 8,748(1,1) 8,664(2,1) 8,661(2,0); 8,659(2,0) 8,455(0,7) 8,449(1,0) 8,445(0,8); 8,435(0,8) 8,429(1,1) 8,425(0,8) 8,199(0,4); 8,176(3,7) 8,174(3,5) 8,169(2,5) 8,147(0,4); 7,637(1,0); 7,625(0,9); 7,617(0,9) 7,605(0,9); 3,318(22,8); 3,216(13,3); 2,676(16,0); 2,525(0,8); 2,511(17,6); 2,507(36,8); 2,502(49,6); 2,498(35,9); 2,493(17,4); 0 ,000(3,3)  δ = 9.263 (1.6) 9.258 (1.6); 8.763 (1.0); 8,760 (1.2); 8.751 (1.1) 8.748 (1.1) 8.664 (2.1) 8.661 (2.0); 8.659 (2.0) 8.455 (0.7) 8.449 (1.0) 8.445 (0.8); 8.435 (0.8) 8.429 (1.1) 8.425 (0.8) 8.199 (0.4); 8.176 (3.7) 8.174 (3.5) 8.169 (2.5) 8.147 (0.4); 7,637 (1.0); 7,625 (0.9); 7.617 (0.9) 7.605 (0.9); 3,318 (22.8); 3,216 (13.3); 2,676 (16.0); 2,525 (0.8); 2,511 (17.6); 2,507 (36.8); 2,502 (49.6); 2,498 (35.9); 2,493 (17.4); 0, 000 (3,3)
52 2,84 2,97 1H-NMR(400,0 MHz, de-DMSO): 52 2.84 2.97 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,269(1,7); 9,264(1,7); 8,767(1,2); 8,763(1,3); δ = 9.269 (1.7); 9,264 (1.7); 8,767 (1.2); 8.763 (1.3);
8,755(1,3) 8,751(1,3) 8,672(2,4) 8,667(2,3); 8,462(0,8) 8,458(1,1) 8,452(0,9) 8,442(0,9); 8,437(1,1) 8,432(0,8) 8,208(1,1) 8,186(3,4); 8,169(2,3) 8,164(2,1) 8,147(0,7) 8,142(0,7); 7,643(1,0) 7,630(1,0); 7,623(0,9) 7,611(0,9); 5,753(2,1). 3,330(89,9); 3,325(76,7); 3,257(1,2); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 8.755 (1.3) 8.751 (1.3) 8.672 (2.4) 8.667 (2.3); 8.462 (0.8) 8.458 (1.1) 8.452 (0.9) 8.442 (0.9); 8.437 (1.1) 8.432 (0.8) 8.208 (1.1) 8.186 (3.4); 8.169 (2.3) 8.164 (2.1) 8.147 (0.7) 8.142 (0.7); 7.643 (1.0) 7.630 (1.0); 7.623 (0.9) 7.611 (0.9); 5,753 (2.1). 3,330 (89.9); 3,325 (76.7); 3.257 (1.2); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
3,239(3,7); 3,219(16,0); 3,202(1,3); 2,676(0,6); 3,239 (3.7); 3,219 (16.0); 3,202 (1.3); 2,676 (0.6);
2,671(0,8); 2,667(0,5); 2,524(2,1); 2,511(47,4);2,671 (0.8); 2,667 (0.5); 2,524 (2.1); 2,511 (47.4);
2,507(99,4); 2,502(133,0); 2,498(94,5); 2,493(44,0);2,507 (99.4); 2.502 (133.0); 2,498 (94.5); 2,493 (44.0);
2,333(0,6); 2,329(0,7); 2,324(0,6); 1,435(4,1);2,333 (0.6); 2.329 (0.7); 2,324 (0.6); 1.435 (4.1);
1,417(8,7); 1,399(4,0); 0,146(0,7); 0,008(6,1); 0,000(169,2); -0,009(5,9); -0,150(0,8) 1,417 (8.7); 1,399 (4.0); 0.146 (0.7); 0.008 (6.1); 0.000 (169.2); -0.009 (5.9); -0.150 (0.8)
53 2,8 2,88 1H-NMR(400,0 MHz, dö-DMSO): 53 2.8 2.88 1 H-NMR (400.0 MHz, dö-DMSO):
δ = 9,264(1,3); 8,765(1,0); 8,754(1,0); 8,605(2,7); δ = 9.264 (1.3); 8,765 (1.0); 8,754 (1.0); 8,605 (2.7);
8,600(2,8); 8,457(0,8); 8,453(1,2); 8,448(0,9);8,600 (2.8); 8.457 (0.8); 8,453 (1.2); 8.448 (0.9);
8,437(0,9); 8,432(1,3); 8,428(0,9); 8,197(1,8);8,437 (0.9); 8,432 (1.3); 8,428 (0.9); 8.197 (1.8);
8,175(3,7); 8,138(2,3); 8,132(2,2); 8,115(1,1);8.175 (3.7); 8,138 (2.3); 8,132 (2.2); 8,115 (1.1);
8,110(1,1); 7,641(1,1); 7,629(1,1); 7,621(1,0);8.110 (1.1); 7,641 (1.1); 7,629 (1.1); 7.621 (1.0);
7,610(1,0); 5,755(1,4); 5,220(1,1); 5,198(3,5);7,610 (1.0); 5,755 (1.4); 5,220 (1.1); 5,198 (3.5);
5,177(3,7); 5,155(1,3); 3,331(86,6); 3,178(16,0);5,177 (3.7); 5,155 (1.3); 3,331 (86.6); 3,178 (16.0);
2,676(0,4); 2,671(0,5); 2,666(0,4); 2,525(1,3);2,676 (0.4); 2,671 (0.5); 2,666 (0.4); 2,525 (1.3);
2,511(33,0); 2,507(69,5); 2,502(93,0); 2,498(66,5);2,511 (33.0); 2,507 (69.5); 2,502 (93.0); 2,498 (66.5);
2,493(31,5); 2,333(0,4); 2,329(0,5); 2,324(0,4); 0,000(9,1) 2,493 (31.5); 2,333 (0.4); 2,329 (0.5); 2,324 (0.4); 0.000 (9.1)
54 2,84 2,91 1H-NMR(400,0 MHz, dö-DMSO): 54 2.84 2.91 1 H-NMR (400.0 MHz, d0-DMSO):
δ = 9,271(9,0); 9,267(8,8); 8,770(6,4); 8,766(7,1); δ = 9.271 (9.0); 9,267 (8.8); 8,770 (6.4); 8.766 (7.1);
8,758(6,9); 8,754(7,0); 8,692(12,4); 8,687(12,3);8.758 (6.9); 8,754 (7.0); 8.692 (12.4); 8,687 (12.3);
8,465(4,1); 8,461(5,2); 8,460(5,1); 8,455(4,2);8,465 (4.1); 8.461 (5.2); 8,460 (5.1); 8.455 (4.2);
8,445(4,5); 8,440(5,8); 8,435(4,3); 8,314(0,7);8,445 (4.5); 8,440 (5.8); 8.435 (4.3); 8.314 (0.7);
8,219(7,2); 8,197(16,0); 8,165(10,8); 8,160(10,2);8.219 (7.2); 8.197 (16.0); 8,165 (10.8); 8,160 (10.2);
8,143(5,0); 8,137(5,1); 7,644(4,7); 7,642(5,0);8,143 (5.0); 8.137 (5.1); 7.644 (4.7); 7,642 (5.0);
7,632(4,7); 7,630(4,9); 7,624(4,7); 7,622(4,9);7,632 (4.7); 7,630 (4.9); 7,624 (4.7); 7,622 (4.9);
7,612(4,5); 7,610(4,8); 5,755(5,4); 4,276(3,6);7.612 (4.5); 7,610 (4.8); 5,755 (5.4); 4,276 (3.6);
4,251(11,6); 4,225(12,2); 4,200(4,2); 4,011(0,4);4,251 (11.6); 4,225 (12.2); 4,200 (4.2); 4,011 (0.4);
3,986(0,4); 3,465(0,3); 3,318(165,1); 3,289(69,5);3,986 (0.4); 3.465 (0.3); 3.318 (165.1); 3,289 (69.5);
3,240(0,7); 3,231(0,7); 3,133(2,1); 3,109(0,4);3,240 (0.7); 3,231 (0.7); 3,133 (2.1); 3,109 (0.4);
2,681(0,5); 2,676(1,2); 2,671(1,6); 2,667(1,2);2,681 (0.5); 2,676 (1.2); 2,671 (1.6); 2,667 (1.2);
2,525(3,6); 2,520(5,5); 2,511(93,2); 2,507(201,2); 2,502(273,5); 2,498(197,0); 2,493(93,6); 2,338(0,5);2,525 (3.6); 2,520 (5.5); 2,511 (93.2); 2.507 (201.2); 2.502 (273.5); 2.498 (197.0); 2,493 (93.6); 2,338 (0.5);
2,334(1,1); 2,329(1,6); 2,325(1,2); 2,320(0,6); 1,989(0,9); 1,176(0,5); 0,000(4,5) 2,334 (1.1); 2,329 (1.6); 2,325 (1.2); 2,320 (0.6); 1,989 (0.9); 1,176 (0.5); 0,000 (4.5)
55 2,23 2,36 1H-NMR(400,0 MHz, de-DMSO): 55 2.23 2.36 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,266(1,8); 9,260(1,8); 8,765(1,3); 8,762(1,4); δ = 9.266 (1.8); 9,260 (1.8); 8,765 (1.3); 8.762 (1.4);
8,753(1,3); 8,750(1,4); 8,667(2,1); 8,664(2,1);8,753 (1.3); 8,750 (1.4); 8,667 (2.1); 8.664 (2.1);
8,460(0,7); 8,455(1,0); 8,450(0,7); 8,440(0,8);8,460 (0.7); 8.455 (1.0); 8,450 (0.7); 8,440 (0.8);
8,435(1,1); 8,430(0,8); 8,201(0,7); 8,179(3,2);8.435 (1.1); 8,430 (0.8); 8,201 (0.7); 8,179 (3.2);
8,170(2,3); 8,165(2,2); 8,147(0,5); 8,142(0,5);8,170 (2.3); 8,165 (2.2); 8.147 (0.5); 8,142 (0.5);
7,638(1,0); 7,627(0,9); 7,619(0,9); 7,606(0,9);7.638 (1.0); 7.627 (0.9); 7,619 (0.9); 7,606 (0.9);
3,823(7,1); 3,316(45,8); 2,671(0,4); 2,525(0,9);3,823 (7.1); 3,316 (45.8); 2,671 (0.4); 2,525 (0.9);
2,511(22,0); 2,507(46,4); 2,502(62,5); 2,498(44,8); 2,493(21,2); 2,329(0,4); 2,126(16,0); 0,000(1,1) Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z]2,511 (22.0); 2,507 (46.4); 2,502 (62.5); 2,498 (44.8); 2,493 (21.2); 2,329 (0.4); 2,126 (16.0); 0.000 (1.1) Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
56 1,79 1,84 1H-NMR(400,0 MHz, de-DMSO): 56 1.79 1.84 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,302(2,2); 9,297(2,2); 8,791(1,6); 8,787(1,7); 8,779(1,7); 8,775(1,6); 8,502(0,9); 8,497(1,3); 8,492(0,9); 8,482(1,0); 8,477(1,3); 8,472(0,9); 8,373(2,8); 8,368(2,8); 8,222(2,6); 8,200(2,9); 7,809(6,0); 7,718(1,8); 7,712(1,7); 7,696(1,6); 7,690(1,6); 7,659(1,2); 7,647(1,2); 7,640(1,1); 7,628(1,1); 3,316(69,3); 3,246(16,0); 2,675(0,5); 2,671(0,6); 2,666(0,5); 2,510(40,9); 2,506(79,3); 2,502(102,5); 2,497(74,0); 2,333(0,5); 2,328(0,6); 2,324(0,4); 0,008(2,6); 0,000(49,1); -0,008(1,9) δ = 9.302 (2.2); 9,297 (2.2); 8.791 (1.6); 8,787 (1.7); 8,779 (1.7); 8,775 (1.6); 8,502 (0.9); 8,497 (1.3); 8.492 (0.9); 8,482 (1.0); 8,477 (1.3); 8,472 (0.9); 8.373 (2.8); 8,368 (2.8); 8.222 (2.6); 8,200 (2.9); 7,809 (6.0); 7,718 (1.8); 7,712 (1.7); 7,696 (1.6); 7,690 (1.6); 7.659 (1.2); 7.647 (1.2); 7,640 (1.1); 7.628 (1.1); 3,316 (69.3); 3,246 (16.0); 2,675 (0.5); 2,671 (0.6); 2,666 (0.5); 2,510 (40.9); 2,506 (79.3); 2.502 (102.5); 2,497 (74.0); 2,333 (0.5); 2,328 (0.6); 2,324 (0.4); 0.008 (2.6); 0,000 (49.1); -0.008 (1.9)
57 1,22 1H-NMR(400,0 MHz, de-DMSO): 57 1.22 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,300(4,4); 8,790(3,2); 8,780(3,2); 8,655(7,2); 8,625(2,3); 8,614(2,3); 8,499(3,0); 8,479(3,2); 8,181(5,4); 8,160(7,1); 8,030(4,1); 8,026(4,2); 8,008(3,2); 8,004(3,3); 7,659(2,5); 7,647(2,6); 7,639(2,6); 7,627(2,4); 3,902(15,3); 3,790(0,8); 3,705(0,4); 3,364(226,3); 3,170(1,1); 2,846(16,0); 2,835(15,9); 2,673(1,4); 2,508(160,5); 2,504(220,4); 2,499(168,9); 2,331(1,2); 1,490(0,6); 1,234(0,4); 0,956(0,6); 0,942(0,9); 0,929(0,4); 0,000(5,0)  δ = 9.300 (4.4); 8,790 (3.2); 8,780 (3.2); 8.655 (7.2); 8.625 (2.3); 8.614 (2.3); 8,499 (3.0); 8.479 (3.2); 8,181 (5.4); 8,160 (7.1); 8,030 (4.1); 8.026 (4.2); 8,008 (3.2); 8,004 (3.3); 7.659 (2.5); 7.647 (2.6); 7,639 (2.6); 7.627 (2.4); 3,902 (15.3); 3,790 (0.8); 3,705 (0.4); 3.364 (226.3); 3,170 (1.1); 2,846 (16.0); 2,835 (15.9); 2,673 (1.4); 2,508 (160.5); 2.504 (220.4); 2.499 (168.9); 2.331 (1.2); 1,490 (0.6); 1,234 (0.4); 0.956 (0.6); 0.942 (0.9); 0.929 (0.4); 0.000 (5.0)
58 1,67 1H-NMR(400,0 MHz, de-DMSO): 58 1.67 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,187(3,6); 9,183(6,3); 8,824(5,7); 8,817(5,9); 8,679(6,3); 8,675(6,5); 8,636(2,1); 8,624(2,0); 8,441(2,1); 8,437(2,3); 8,435(2,7); 8,430(2,0); 8,418(2,1); 8,413(2,5); 8,411(2,6); 8,407(2,0); 8,198(5,7); 8,177(7,4); 8,042(4,3); 8,038(4,4); 8,021(3,4); 8,016(3,5); 3,902(11,1); 3,508(0,4); 3,344(379,2); 3,174(0,6); 3,165(0,6); 2,847(16,0); 2,836(16,0); 2,677(0,9); 2,673(1,3); 2,668(0,9); 2,663(0,5); 2,526(3,1); 2,513(69,7); 2,508(149,1); 2,503(210,5); 2,499(156,6); 2,495(74,0); 2,335(0,8); 2,330(1,2); 2,326(0,8); 1,233(0,3); 0,000(7,5)  δ = 9.187 (3.6); 9.183 (6.3); 8.824 (5.7); 8.817 (5.9); 8,679 (6.3); 8,675 (6.5); 8,636 (2.1); 8.624 (2.0); 8,441 (2.1); 8,437 (2.3); 8.435 (2.7); 8,430 (2.0); 8,418 (2.1); 8.413 (2.5); 8,411 (2.6); 8,407 (2.0); 8,198 (5.7); 8,177 (7.4); 8,042 (4.3); 8,038 (4.4); 8,021 (3.4); 8.016 (3.5); 3,902 (11.1); 3,508 (0.4); 3,344 (379.2); 3,174 (0.6); 3,165 (0.6); 2,847 (16.0); 2,836 (16.0); 2,677 (0.9); 2,673 (1.3); 2,668 (0.9); 2,663 (0.5); 2,526 (3.1); 2,513 (69.7); 2,508 (149.1); 2.503 (210.5); 2.499 (156.6); 2,495 (74.0); 2,335 (0.8); 2,330 (1.2); 2,326 (0.8); 1,233 (0.3); 0.000 (7.5)
59 1,42 1H-NMR(400,0 MHz, de-DMSO): 59 1.42 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,296(5,7); 8,789(3,9); 8,778(4,0); 8,498(2,9); 8,493(4,2); 8,489(3,1); 8,478(3,3); 8,473(4,6); 8,469(3,2); 8,300(9,9); 8,297(10,6); 8,159(9,2); 8,138(10,0); 7,658(3,6); 7,646(3,7); 7,639(3,6); 7,626(3,5); 7,613(6,8); 7,609(6,8); 7,592(6,3); 7,588(6,5); 3,902(16,0); 3,509(0,4); 3,347(670,5); 3,344(680,6); 3,169(0,6); 3,035(7,7); 2,971(7,9); 2,677(1,4); 2,673(1,8); 2,668(1,4); 2,526(4,8); 2,513(102,9); 2,508(216,1); 2,504(302,3); 2,499(224,6); 2,495(106,7); 2,335(1,2); 2,331(1,7); 2,326(1,2); 0,000(10,9)  δ = 9.296 (5.7); 8,789 (3.9); 8,778 (4.0); 8,498 (2.9); 8,493 (4.2); 8,489 (3.1); 8.478 (3.3); 8.473 (4.6); 8.469 (3.2); 8,300 (9.9); 8,297 (10.6); 8.159 (9.2); 8,138 (10.0); 7,658 (3.6); 7,646 (3.7); 7,639 (3.6); 7,626 (3.5); 7,613 (6.8); 7,609 (6.8); 7,592 (6.3); 7,588 (6.5); 3,902 (16.0); 3,509 (0.4); 3.347 (670.5); 3,344 (680.6); 3,169 (0.6); 3,035 (7.7); 2,971 (7.9); 2,677 (1.4); 2,673 (1.8); 2,668 (1.4); 2,526 (4.8); 2.513 (102.9); 2,508 (216.1); 2.504 (302.3); 2.499 (224.6); 2.495 (106.7); 2,335 (1.2); 2.331 (1.7); 2,326 (1.2); 0.000 (10.9)
60 1,9 1H-NMR(400,0 MHz, de-DMSO): 60 1.9 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,179(10,2); 8,820(9,1); 8,814(9,5); 8,437(3,2); 8,431(4,2); 8,426(3,2); 8,414(3,3); 8,407(4,1); 8,402(3,2); 8,327(11,1); 8,323(11,2); 8,313(0,4); 8,176(10,3); 8,155(11,1); 7,629(7,2); 7,625(7,3); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] δ = 9.179 (10.2); 8,820 (9.1); 8,814 (9.5); 8,437 (3.2); 8,431 (4.2); 8,426 (3.2); 8,414 (3.3); 8,407 (4.1); 8,402 (3.2); 8,327 (11.1); 8.323 (11.2); 8,313 (0.4); 8,176 (10.3); 8.155 (11.1); 7,629 (7.2); 7,625 (7.3); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
7,608(6,7); 7,604(7,0); 3,902(16,0); 3,335(556,1) 3,175(0,6); 3,163(0,6); 3,037(8,7); 2,967(8,9) 2,676(1,3); 2,672(1,9); 2,667(1,4); 2,525(4,9) 2,512(107,2); 2,507(227,2); 2,503(319,9); 2,498(239,7) 2,494(115,3); 2,334(1,3); 2,330(1,8); 2,325(1,3) 1,234(0,4); 0,008(0,4); 0,000(11,0); -0,008(0,4) 7,608 (6.7); 7,604 (7.0); 3,902 (16.0); 3.355 (556.1) 3.175 (0.6); 3,163 (0.6); 3,037 (8.7); 2.967 (8.9) 2.676 (1.3); 2,672 (1.9); 2,667 (1.4); 2.525 (4.9) 2.512 (107.2); 2.507 (227.2); 2.503 (319.9); 2,498 (239.7) 2,494 (115.3); 2,334 (1.3); 2,330 (1.8); 2.325 (1.3) 1.234 (0.4); 0.008 (0.4); 0,000 (11.0); -0.008 (0.4)
61 1,71 1H-NMR(400,0 MHz, de-DMSO): 61 1.71 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,298(4,8); 8,791(3,4); 8,780(3,4); 8,496(2,7) δ = 9,298 (4,8); 8.791 (3.4); 8,780 (3.4); 8,496 (2.7)
8,491(4,0); 8,487(2,9); 8,476(3,0); 8,471(4,2)8,491 (4.0); 8,487 (2.9); 8,476 (3.0); 8,471 (4.2)
8,467(2,8); 8,313(0,4); 8,276(3,1); 8,159(7,8)8,467 (2.8); 8,313 (0.4); 8.276 (3.1); 8.159 (7.8)
8,138(8,4); 7,658(3,2); 7,646(3,3); 7,638(3,2)8,138 (8.4); 7,658 (3.2); 7,646 (3.3); 7.638 (3.2)
7,626(3,0); 7,572(1,8); 3,902(16,0); 3,507(1,4)7,626 (3.0); 7,572 (1.8); 3,902 (16.0); 3,507 (1.4)
3,436(0,6); 3,334(499,5); 3,268(1,6); 3,176(0,8)3,436 (0.6); 3.334 (499.5); 3,268 (1.6); 3.176 (0.8)
3,164(0,8); 2,989(3,6); 2,944(3,0); 2,677(1,2)3,164 (0.8); 2,989 (3.6); 2,944 (3.0); 2,677 (1.2)
2,672(1,7); 2,668(1,3); 2,550(0,5); 2,525(4,5) 2,512(100,1); 2,508(211,4); 2,503(297,6); 2,499(223,2)2,672 (1.7); 2,668 (1.3); 2,550 (0.5); 2.525 (4.5) 2.512 (100.1); 2,508 (211.4); 2.503 (297.6); 2.499 (223.2)
2,494(107,3); 2,334(1,2); 2,330(1,7); 2,325(1,2)2.494 (107.3); 2,334 (1.2); 2,330 (1.7); 2.325 (1.2)
1,248(0,3); 1,234(0,6); 1,164(2,1); 1,100(2,5) 0,000(8,0) 1,248 (0.3); 1,234 (0.6); 1,164 (2.1); 1,100 (2.5) 0.000 (8.0)
62 2,2 1H-NMR(400,0 MHz, de-DMSO): 62 2.2 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,177(8,8); 8,820(8,1); 8,813(8,5); 8,435(2,6) δ = 9.177 (8.8); 8,820 (8.1); 8,813 (8.5); 8,435 (2.6)
8,429(3,5) 8,424(2,6); 8,412(2,8); 8,406(3,5) 8,400(2,6) 8,304(2,9); 8,176(7,8); 8,155(8,4) 7,587(1,8) 3,902(16,0); 3,509(1,3); 3,439(0,5) 3,331(326, 1); 3,255(1,5); 3,168(0,5); 2,993(3,5) 2,940(2,9) 2,677(1,3); 2,672(1,7); 2,667(1,3) 2,658(0,3) 2,525(4,2); 2,512(101,2); 2,507(214,6) 2,503(301, 5); 2,498(224,0); 2,494(106,6); 2,334(1,2) 2,330(1,7) 2,325(1,3); 1,250(0,4); 1,234(0,5) 1,169(2,1); 1,096(2,4); 0,008(0,5); 0,000(13,3); ■ 0,009(0,4) 8.429 (3.5) 8.424 (2.6); 8.412 (2.8); 8.406 (3.5) 8.400 (2.6) 8.304 (2.9); 8,176 (7.8); 8.155 (8.4), 7.587 (1.8) 3.902 (16.0); 3,509 (1.3); 3,439 (0.5) 3.331 (326.1); 3,255 (1.5); 3,168 (0.5); 2,993 (3.5) 2.940 (2.9) 2.677 (1.3); 2,672 (1.7); 2.667 (1.3) 2.658 (0.3) 2.525 (4.2); 2.512 (101.2); 2.507 (214.6) 2.503 (301, 5); 2.498 (224.0); 2.494 (106.6); 2.334 (1.2) 2.330 (1.7) 2.325 (1.3); 1,250 (0.4); 1.234 (0.5) 1.169 (2.1); 1,096 (2.4); 0.008 (0.5); 0,000 (13.3); ■ 0.009 (0.4)
63 2,02 1H-NMR(400,0 MHz, de-DMSO): 63 2.02 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,319(2 :,7); 9,292(1,4); 9,277(2,5) 9,262(1,2) 8,803(1,9) 8,794(1,9) 8,746(6,0) 8,742(6,1) 8,513(2,5) 8,492(2,6) 8,223(4,6) 8,201(6,2) 8,086(3,6) 8,082(3,6) 8,065(2,7) 8,060(2,7) 7,667(1,9) 7,655(1,9) 7,647(2,0) 7,635(1,7) 4,198(0,8) 4,174(2,4); 4,158(2,5) 4,150(2,6) 4,134(2,3) 4,126(1,1); 4,110(0,8); 3,902(16,0) 3,509(0,4) 3,338(167,0); 3,174(0,4); 2,677(1,0) 2,672(1,3); 2,667(1,0); 2,663(0,5); 2,525(3,6) 2,512(77,6) 2,507(164,1); 2,503(230,3); 2,498(170,6) 2,494(80,3) 2,334(0,9); 2,330(1,3); 2,325(0,9) 2,320(0,4); 1,234(0,3); 0,008(0,4); 0, 000(11,5); ■ 0,009(0,4) δ = 9.319 (2 :, 7); 9,292 (1.4); 9.277 (2.5) 9.262 (1.2) 8.803 (1.9) 8.794 (1.9) 8.746 (6.0) 8.742 (6.1) 8.513 (2.5) 8.492 (2.6) 8.223 ( 4,6) 8,201 (6,2) 8,086 (3,6) 8,082 (3,6) 8,065 (2,7) 8,060 (2,7) 7,667 (1,9) 7,655 (1,9) 7,647 (2, 0) 7.635 (1.7) 4.198 (0.8) 4.174 (2.4); 4.158 (2.5) 4,150 (2,6) 4,134 (2,3) 4,126 (1,1); 4,110 (0.8); 3.902 (16.0) 3.509 (0.4) 3.338 (167.0); 3,174 (0.4); 2,677 (1.0) 2,672 (1.3); 2,667 (1.0); 2,663 (0.5); 2.525 (3.6) 2.512 (77.6) 2.507 (164.1); 2.503 (230.3); 2.498 (170.6) 2.494 (80.3) 2.334 (0.9); 2,330 (1.3); 2.325 (0.9) 2.320 (0.4); 1,234 (0.3); 0.008 (0.4); 0, 000 (11.5); ■ 0.009 (0.4)
64 2,51 1H-NMR(400,0 MHz, de-DMSO): 64 2.51 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,308(1,6); 9,293(3,3); 9,277(1,5); 9,200(4,0) δ = 9.308 (1.6); 9.293 (3.3); 9,277 (1.5); 9,200 (4.0)
9,196(6,8); 8,832(6,1); 8,825(6,3); 8,764(6,7)9,196 (6.8); 8,832 (6.1); 8,825 (6.3); 8.764 (6.7)
8,760(6,8); 8,659(0,4); 8,654(0,4); 8,620(0,4)8,760 (6.8); 8,659 (0.4); 8,654 (0.4); 8,620 (0.4)
8,615(0,4); 8,605(0,6); 8,456(2,2); 8,450(2,7)8,615 (0.4); 8,605 (0.6); 8.456 (2.2); 8,450 (2.7)
8,445(2,1); 8,433(2,2); 8,428(2,6); 8,427(2,6) Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 8,445 (2.1); 8.433 (2.2); 8,428 (2.6); 8,427 (2.6) Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
8,422(2,1) 8,240(5,8) 8,219(7,8) 8,148(0,5); 8,097(4,5) 8,093(4,3) 8,076(3,4) 8,071(3,4); 7,645(0,4) 7,641(0,5) 7,627(0,5) 7,602(0,4); 7,596(0,4) 4,200(1,0) 4,184(1,2) 4,176(3,2); 4,160(3,2) 4,151(3,4); 4,136(3,2) 4,127(1,3); 4,111(1,2); 3,902(16,0); 3,583(0,4); 3,508(0,7); 3,360(1004, ,1); 3,177(0,9) 3,164(0,9); 2,678(1,1); 2,674(1,5); 2,669(1,1); 2,665(0,5); 2,527(4,1); 2,514(87,9); 2,509(183,7); 2,505(255,8); 2,500(188,6); 2,496(88,4); 2,336(1,0); 2,332(1,4); 2,327(1,0); 0,000(4,8)  8.422 (2.1) 8.240 (5.8) 8.219 (7.8) 8.148 (0.5); 8.097 (4.5) 8.093 (4.3) 8.076 (3.4) 8.071 (3.4); 7.645 (0.4) 7.641 (0.5) 7.627 (0.5) 7.602 (0.4); 7.596 (0.4) 4,200 (1.0) 4.184 (1.2) 4.176 (3.2); 4.160 (3.2) 4.151 (3.4); 4.166 (3.2) 4.127 (1.3); 4,111 (1.2); 3,902 (16.0); 3,583 (0.4); 3,508 (0.7); 3,360 (1004,, 1); 3.177 (0.9) 3.164 (0.9); 2,678 (1.1); 2,674 (1.5); 2,669 (1.1); 2,665 (0.5); 2,527 (4.1); 2,514 (87.9); 2.509 (183.7); 2.505 (255.8); 2,500 (188.6); 2,496 (88.4); 2,336 (1.0); 2,332 (1.4); 2,327 (1.0); 0.000 (4.8)
65 1,64 1H-NMR(400,0 MHz, de-DMSO): 65 1.64 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,303(1,4); 8,794(1,0); 8,783(1,0); 8,499(1,1); δ = 9.303 (1.4); 8,794 (1.0); 8.783 (1.0); 8,499 (1.1);
8,485(3,3) 8,481(3,7) 8,169(2,6) 8,148(2,8);8.485 (3.3) 8.481 (3.7) 8.169 (2.6) 8.148 (2.8);
7,792(1,9) 7,788(1,9) 7,771(1,7) 7,766(1,7);7,792 (1.9) 7.788 (1.9) 7.771 (1.7) 7.766 (1.7);
7,661(0,9) 7,650(0,9) 7,642(0,9) 7,630(0,8);7.661 (0.9) 7.650 (0.9) 7.642 (0.9) 7.630 (0.8);
3,902(4,8) 3,583(16,0) 3,343(62,3) 3,317(22,5);3,902 (4.8) 3.583 (16.0) 3.343 (62.3) 3.317 (22.5);
2,676(0,4); 2,672(0,5); 2,668(0,4) 2,525(1,5);2,676 (0.4); 2,672 (0.5); 2.668 (0.4) 2.525 (1.5);
2,512(30,7) 2,507(64,3) 2,503(90,0); 2,498(66,7);2.512 (30.7) 2.507 (64.3) 2.503 (90.0); 2,498 (66.7);
2,494(31,5) 2,334(0,3) 2,330(0,5); 2,325(0,3);2.494 (31.5) 2.334 (0.3) 2.330 (0.5); 2,325 (0.3);
1,290(0,4); 0,000(4,0) 1,290 (0.4); 0.000 (4.0)
66 2,16 1H-NMR(400,0 MHz, de-DMSO): 66 2.16 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,183(3,3); 8,827(2,7); 8,820(2,9); 8,507(4,0); δ = 9.183 (3.3); 8,827 (2.7); 8,820 (2.9); 8.507 (4.0);
8,442(0,9); 8,436(1,4); 8,431(1,1); 8,418(1,0);8.442 (0.9); 8.436 (1.4); 8,431 (1.1); 8,418 (1.0);
8,412(1,4); 8,408(1,0); 8,186(2,9); 8,165(3,2);8.412 (1.4); 8.408 (1.0); 8,186 (2.9); 8,165 (3.2);
7,803(1,8); 7,800(2,1); 7,783(1,6); 7,779(1,9); 3,902(4,4); 3,582(16,0); 3,338(162,6); 3,331(226,7);7,803 (1.8); 7,800 (2.1); 7,783 (1.6); 7,779 (1.9); 3,902 (4.4); 3,582 (16.0); 3.338 (162.6); 3.331 (226.7);
3,318(20,4); 2,672(0,7); 2,503(111,3); 2,499(91,9); 2,330(0,6); 0,000(3,5) 3,318 (20.4); 2,672 (0.7); 2.503 (111.3); 2,499 (91.9); 2,330 (0.6); 0.000 (3.5)
67 1,91 1H-NMR(400,0 MHz, de-DMSO): 67 1.91 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,317(3,0); 9,019(1,7); 9,004(3,4); 8,988(1,6) δ = 9.317 (3.0); 9,019 (1.7); 9.004 (3.4); 8,988 (1.6)
8,799(2,2); 8,791(2,2); 8,732(7,4); 8,728(7,7).8.799 (2.2); 8.791 (2.2); 8.732 (7.4); 8,728 (7.7).
8,510(3,1); 8,490(3,2); 8,205(6,0); 8,183(8,4).8.510 (3.1); 8,490 (3.2); 8,205 (6.0); 8,183 (8.4).
8,083(4,8); 8,079(4,8); 8,062(3,5); 8,057(3,5).8,083 (4.8); 8.079 (4.8); 8.062 (3.5); 8,057 (3.5).
7,665(2,2); 7,653(2,2); 7,645(2,3); 7,633(1,9).7,665 (2.2); 7,653 (2.2); 7,645 (2.3); 7,633 (1.9).
3,902(15,5); 3,828(2,1); 3,813(2,1); 3,793(4,2).3,902 (15.5); 3,828 (2.1); 3,813 (2.1); 3.793 (4.2).
3,778(4,1); 3,758(2,2); 3,743(2,1); 3,557(0,4).3,778 (4.1); 3,758 (2.2); 3,743 (2.1); 3,557 (0.4).
3,553(0,4); 3,508(0,6); 3,339(258,1); 3,169(0,8).3,553 (0.4); 3,508 (0.6); 3,339 (258.1); 3,169 (0.8).
2,677(1,2); 2,672(1,7); 2,667(1,3); 2,525(4,3). 2,512(93,2); 2,507(200,3); 2,503(284,4); 2,498(213,3).2,677 (1.2); 2,672 (1.7); 2,667 (1.3); 2.525 (4.3). 2,512 (93.2); 2.507 (200.3); 2.503 (284.4); 2.498 (213.3).
2,494(102,0); 2,334(1,1); 2,330(1,5); 2,325(1,1)2.494 (102.0); 2,334 (1.1); 2,330 (1.5); 2.325 (1.1)
1,708(7,2); 1,661(16,0); 1,613(7,9); 1,233(0,4) 0,008(0,4); 0,000(12,3); -0,009(0,4) 1,708 (7.2); 1,661 (16.0); 1,613 (7.9); 1.233 (0.4) 0.008 (0.4); 0,000 (12.3); -0.009 (0.4)
68 2,39 1H-NMR(400,0 MHz, de-DMSO): 68 2.39 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,195(7,3); 9,032(1,7); 9,017(3,6); 9,001(1,7); δ = 9.195 (7.3); 9,032 (1.7); 9.017 (3.6); 9,001 (1.7);
8,829(6,7); 8,822(6,9); 8,751(7,0); 8,748(7,3);8.829 (6.7); 8,822 (6.9); 8.751 (7.0); 8.748 (7.3);
8,455(2,3); 8,448(3,1); 8,444(2,3); 8,431(2,4);8.455 (2.3); 8.448 (3.1); 8,444 (2.3); 8,431 (2.4);
8,425(2,9); 8,420(2,2); 8,222(6,1); 8,201(8,5);8,425 (2.9); 8,420 (2.2); 8.222 (6.1); 8,201 (8.5);
8,094(4,7); 8,090(4,7); 8,073(3,5); 8,068(3,6);8,094 (4.7); 8,090 (4.7); 8,073 (3.5); 8,068 (3.6);
3,902(16,0); 3,830(2,1); 3,814(2,0); 3,795(4,2);3,902 (16.0); 3,830 (2.1); 3,814 (2.0); 3,795 (4.2);
3,779(4,1); 3,760(2,2); 3,744(2,1); 3,549(0,4); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 3,779 (4.1); 3,760 (2.2); 3.744 (2.1); 3,549 (0.4); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
3,508(0,6); 3,348(819,5); 3,177(0,9); 3,163(0,9) 2,678(1,2); 2,673(1,6); 2,668(1,2); 2,526(4,4) 2,513(94,7); 2,508(199,6); 2,504(280,4); 2,499(209,9) 2,495(100,6); 2,335(1,1); 2,331(1,5); 2,326(1,1) 1,710(7,0); 1,662(15,4); 1,615(7,6); 1,234(0,3) 0,000(6,1)  3,508 (0.6); 3.348 (819.5); 3,177 (0.9); 3.163 (0.9) 2.678 (1.2); 2,673 (1.6); 2,668 (1.2); 2.526 (4.4) 2.513 (94.7); 2,508 (199.6); 2.504 (280.4); 2,499 (209.9) 2.495 (100.6); 2,335 (1.1); 2.331 (1.5); 2.326 (1.1) 1.710 (7.0); 1,662 (15.4); 1,615 (7.6); 1,234 (0,3) 0,000 (6,1)
69 1,83 1H-NMR(400,0 MHz, de-DMSO): 69 1.83 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,311(1,1); 8,791(1,7); 8,673(2,3); 8,670(2,4) δ = 9.31 (1.1); 8.791 (1.7); 8,673 (2.3); 8,670 (2.4)
8,503(1,0) 8,483(1,0); 8,195(1,7); 8,173(2,2) 8,044(1,3) 8,040(1,3); 8,022(1,0); 8,018(1,0) 7,662(0,8) 7,650(0,8); 7,643(0,8); 7,631(0,7) 3,902(4,4) 3,534(0,8); 3,518(1,6); 3,500(1,6) 3,485(0,9). 3,337(125,1); 2,711(1,7); 2,693(2,5) 2,676(1,9) 2,525(1,4); 2,508(61,7); 2,503(86,2) 2,499(65,5); 2,334(0,4); 2,330(0,5); 2,326(0,4)8.503 (1.0) 8.483 (1.0); 8,195 (1.7); 8.173 (2.2) 8.044 (1.3) 8.040 (1.3); 8,022 (1.0); 8.018 (1.0) 7.662 (0.8) 7.650 (0.8); 7.643 (0.8); 7.631 (0.7) 3.902 (4.4) 3.534 (0.8); 3,518 (1.6); 3,500 (1.6) 3.485 (0.9). 3.337 (125.1); 2,711 (1.7); 2.663 (2.5) 2.676 (1.9) 2.525 (1.4); 2,508 (61.7); 2.503 (86.2) 2.499 (65.5); 2,334 (0.4); 2,330 (0.5); 2.326 (0.4)
2,123(16,0); 0,000(3,7) 2,123 (16.0); 0.000 (3.7)
70 2,31 1H-NMR(400,0 MHz, de-DMSO): 70 2.31 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,188(2,4); 8,826(2,2); 8,820(2,4); 8,800(1,2) δ = 9.188 (2.4); 8.826 (2.2); 8,820 (2.4); 8,800 (1.2)
8,787(0,6); 8,694(2,3); 8,691(2,6) 8,446(0,7) 8,440(1,0); 8,436(0,7); 8,423(0,7) 8,417(1,0) 8,412(0,7); 8,212(2,0); 8,190(2,6) 8,056(1,5) 8,052(1,5); 8,035(1,1); 8,030(1,2) 3,902(4,7) 3,535(0,8); 3,519(1,7); 3,501(1,8) 3,485(0,9) 3,332(120,3); 3,176(0,5); 3,163(0,5); 2,711(1,8)8,787 (0.6); 8.694 (2.3); 8.691 (2.6) 8.466 (0.7) 8.440 (1.0); 8.436 (0.7); 8.423 (0.7) 8.417 (1.0) 8.412 (0.7); 8,212 (2.0); 8.190 (2.6) 8.056 (1.5) 8.052 (1.5); 8,035 (1.1); 8.030 (1.2) 3.902 (4.7) 3.535 (0.8); 3,519 (1.7); 3,501 (1.8) 3.485 (0.9) 3.332 (120.3); 3,176 (0.5); 3,163 (0.5); 2,711 (1.8)
2,693(2,8); 2,676(2,1); 2,507(63,8); 2,503(89,9) 2,498(69,3); 2,333(0,4); 2,329(0,5); 2,325(0,4) 2,122(16,0); 0,000(3,8) 2,693 (2.8); 2,676 (2.1); 2,507 (63.8); 2.503 (89.9) 2.498 (69.3); 2,333 (0.4); 2,329 (0.5); 2.325 (0.4) 2.122 (16.0); 0.000 (3.8)
71 1,19 1H-NMR(400,0 MHz, de-DMSO): 71, 1.19 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,310(1,5); 8,925(0,8); 8,912(1,6); 8,899(0,8) 8,789(1,2); 8,669(3,6); 8,505(1,5); 8,485(1,5) 8,206(2,5); 8,185(3,2); 8,036(1,8); 8,032(2,0) 8,010(1,6); 7,664(1,1); 7,652(1,1); 7,645(1,1) 7,633(1,0); 3,901(12,1); 3,757(1,1); 3,741(2,6) 3,726(2,7); 3,709(1,4); 3,437(8,0); 3,419(14,7) 3,372(744,9); 3,170(1,6); 3,117(0,6); 3,063(16,0) 2,673(1,7); 2,508(210,9); 2,504(294,2); 2,500(232,0) 2,331(1,8); 1,491(0,5); 1,336(0,4); 1,297(0,3) 1,250(0,4); 1,234(0,7); 0,969(0,9); 0,954(1,1) 0,867(0,6); 0,849(1,1); 0,832(0,6); 0,000(6,2)  δ = 9.310 (1.5); 8,925 (0.8); 8.912 (1.6); 8,899 (0.8) 8,789 (1.2); 8,669 (3.6); 8,505 (1.5); 8.485 (1.5) 8.206 (2.5); 8.185 (3.2); 8,036 (1.8); 8.032 (2.0) 8.010 (1.6); 7.664 (1.1); 7,652 (1.1); 7.645 (1.1) 7.633 (1.0); 3,901 (12.1); 3,757 (1.1); 3.741 (2.6) 3.726 (2.7); 3,709 (1.4); 3,437 (8.0); 3,419 (14.7) 3.372 (744.9); 3,170 (1.6); 3,117 (0.6); 3.063 (16.0) 2.673 (1.7); 2,508 (210.9); 2.504 (294.2); 2,500 (232,0) 2,331 (1.8); 1.491 (0.5); 1.336 (0.4); 1.297 (0.3) 1.250 (0.4); 1,234 (0.7); 0.969 (0.9); 0.954 (1.1) 0.867 (0.6); 0.849 (1.1); 0.832 (0.6); 0.000 (6.2)
72 1,54 'H-NMRCöOl.ö MHz, de-DMSO):  72 1.54 'H-NMRCöOl.ö MHz, de-DMSO):
= 9,189(3, ,1); 8,945(0,8); 8,936(1,7); 8,927(0,9) ,828(2,8) 8,823(2,9); 8,700(3,4) 8,698(3,4) ,444(1,0) 8,441(1,2); 8,440(1,2) 8,437(1,0) ,429(1,0) 8,426(1,3); 8,424(1,2) 8,421(1,0) ,220(2,7) 8,206(3,2); 8,045(2,1) 8,043(2,1) ,031(1,8) 8,028(1,9); 3,903(0,4) 3,749(1,0) ,738(2,5) 3,728(2,5); 3,717(1,2) 3,434(2,1) ,423(3,9). 3,412(1,9); 2 ,323(84,1); 3,065(16,0) ,617(0,4) 2,614(0,6); 2,611(0,4); 2,523(1,0) ,520(1,3). 2,517(1,4); 7 ,508(32,3); 2,505(66,1) ,502(88,4); 2,499(65,0); 2,496(31,6); 2,389(0,4) Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] = 9.189 (3,, 1); 8,945 (0.8); 8,936 (1.7); 8.927 (0.9), 828 (2.8), 8.823 (2.9); 8.700 (3.4) 8.698 (3.4), 444 (1.0) 8.441 (1.2); 8.440 (1.2) 8.437 (1.0), 429 (1.0) 8.426 (1.3); 8.424 (1.2) 8.421 (1.0), 220 (2.7) 8.206 (3.2); 8.045 (2.1) 8.043 (2.1), 031 (1.8) 8.028 (1.9); 3.903 (0.4) 3.749 (1.0), 738 (2.5) 3.728 (2.5); 3.717 (1.2) 3.434 (2.1), 423 (3.9). 3,412 (1.9); 2, 323 (84,1); 3.065 (16.0), 617 (0.4) 2.614 (0.6); 2,611 (0.4); 2.523 (1.0), 520 (1.3). 2,517 (1.4); 7, 508 (32,3); 2,505 (66.1), 502 (88.4); 2,499 (65.0); 2,496 (31.6); 2,389 (0.4) Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
2,386(0,6); 2,383(0,4); 0,000(2,3)  2,386 (0.6); 2,383 (0.4); 0.000 (2.3)
73 3,76 'H-NMRCöOl.ö MHz, de-DMSO):  73 3.76 'H-NMRCO10.10 MHz, de-DMSO):
δ = 10,709(12,1); 9,334(11,9); 9,331(11,8) 8,842(16,0); 8,839(15,6); 8,806(9,2); 8,804(9,4) 8,798(9,5); 8,796(9,4); 8,530(5,2); 8,527(6,9) 8,524(5,1); 8,517(5,6); 8,514(7,0); 8,513(7,1) 8,510(5,2); 8,285(13,5); 8,267(12,0); 8,253(15,7) 8,163(10,8); 8,160(10,3); 8,149(8,4); 8,146(8,5) 8,042(6,6); 8,041(6,2); 8,030(6,3); 8,029(6,9) 8,027(7,0); 8,025(5,9); 7,669(6,4); 7,668(6,2) 7,661(6,2); 7,660(6,2); 7,655(6,4); 7,654(6,1) 7,647(6,1); 7,646(5,9); 7,578(7,0); 7,565(13,9) 7,551(8,8); 7,481(8,2); 7,468(6,1); 3,322(653,6) 2,617(2,3); 2,614(3,0); 2,611(2,2); 2,523(5,6) 2,520(7,0); 2,517(7,4); 2,508(166,5); 2,505(342,4) 2,502(455,6); 2,499(335,2); 2,496(160,8); 2,389(2,1) 2,386(2,8); 2,383(2,0); 1,351(0,5); 1,231(1,5) 0,853(0,3); 0,000(11,8)  δ = 10.709 (12.1); 9.334 (11.9); 9,331 (11.8) 8,842 (16.0); 8,839 (15.6); 8,806 (9.2); 8,804 (9.4) 8,798 (9.5); 8,796 (9.4); 8,530 (5.2); 8.527 (6.9) 8.524 (5.1); 8,517 (5.6); 8,514 (7.0); 8.513 (7.1) 8.510 (5.2); 8,285 (13.5); 8,267 (12.0); 8.253 (15.7) 8.163 (10.8); 8,160 (10.3); 8,149 (8.4); 8.146 (8.5) 8.042 (6.6); 8.041 (6.2); 8,030 (6.3); 8.029 (6.9) 8.027 (7.0); 8,025 (5.9); 7.669 (6.4); 7.686 (6.2) 7.661 (6.2); 7,660 (6.2); 7.655 (6.4); 7.654 (6.1) 7.647 (6.1); 7,646 (5.9); 7,578 (7.0); 7,565 (13.9), 7,551 (8.8); 7,481 (8.2); 7,468 (6.1); 3.322 (653.6) 2.617 (2.3); 2,614 (3.0); 2,611 (2.2); 2.523 (5.6) 2.520 (7.0); 2,517 (7.4); 2,508 (166.5); 2,505 (342.4) 2.502 (455.6); 2.499 (335.2); 2.496 (160.8); 2.389 (2.1) 2.386 (2.8); 2,383 (2.0); 1,351 (0.5); 1.231 (1.5) 0.853 (0.3); 0.000 (11.8)
74 4,29 'H-NMRCöOl.ö MHz, de-DMSO):  74 4.29 'H-NMRCöOl.ö MHz, de-DMSO):
δ = 10,720(6,1); 9,217(5,6); 9,215(8,8) 8,863(10,1) 8,860(10,0); 8,839(9,2); 8,835(9,3); 8,470(3,0) δ = 10.720 (6.1); 9,217 (5.6); 9.215 (8.8) 8.863 (10.1) 8.860 (10.0); 8,839 (9.2); 8,835 (9.3); 8,470 (3.0)
,467(3,7) 8,466(3,7); 8,463(2,9); 8,455(3,2) ,451(3,9) 8,450(3,5); 8,447(2,9); 8,282(16,0) ,268(9,9) 8,173(6,8); 8,170(6,5); 8,159(5,4) ,156(5,4) 8,041(4,3); 8,039(4,0); 8,029(4,0) ,027(4,4) 8,025(4,5); 8,024(3,8); 7,578(4,4) ,565(8,8) 7,552(5,6); 7,481(5,3); 7,468(4,0) ,756(0,9). 3,351(0,5); 3,323(315,1); 3,174(0,5) ,165(0,5) 2,617(1,0); 2,614(1,3); 2,611(1,0) ,523(2,5) 2,520(3,2); 2,517(3,6); 2,508(74,4) ,505(151.5); 2,502(200,8); 2,499(148,7); 2,496(72,2) ,389(1,0) 2,386(1,3); 2,383(0,9); 1,352(1,5) ,231(2,2). 0,852(0,5); 0,000(5,7) , 467 (3.7) 8.466 (3.7); 8.463 (2.9); 8.455 (3.2), 451 (3.9) 8.450 (3.5); 8,447 (2.9); 8,282 (16.0), 268 (9.9), 8.173 (6.8); 8,170 (6.5); 8,159 (5.4), 156 (5.4) 8.041 (4.3); 8,039 (4.0); 8.029 (4.0), 027 (4.4) 8.025 (4.5); 8.024 (3.8); 7,578 (4.4), 565 (8.8), 7,552 (5.6); 7,481 (5.3); 7.468 (4.0), 756 (0.9). 3,351 (0.5); 3.323 (315.1); 3.174 (0.5), 165 (0.5) 2.617 (1.0); 2,614 (1.3); 2,611 (1.0), 523 (2.5) 2.520 (3.2); 2,517 (3.6); 2,508 (74,4), 505 (151.5); 2.502 (200.8); 2.499 (148.7); 2.496 (72.2), 389 (1.0) 2.386 (1.3); 2,383 (0.9); 1.352 (1.5), 231 (2.2). 0.852 (0.5); 0.000 (5.7)
75 3,26 'H-NMRCöOl.ö MHz, de-DMSO):  75 3.26 'H-NMRCöOl.ö MHz, de-DMSO):
δ = 10,878(15,2); 9,218(13,9); 9,188(0,6); 8,886(16,0) δ = 10.878 (15.2); 9,218 (13.9); 9.188 (0.6); 8.886 (16.0)
8,884(15,6); 8,841(14,1); 8,837(14,1); 8,825(0,8)8.884 (15.6); 8,841 (14.1); 8,837 (14.1); 8,825 (0.8)
8,820(0,7); 8,724(0,8); 8,722(0,9); 8,474(5,0)8,820 (0.7); 8,724 (0.8); 8.722 (0.9); 8.474 (5.0)
8,471(6,4); 8,470(6,5); 8,461(13,9); 8,459(13,6)8,471 (6.4); 8,470 (6.5); 8.461 (13.9); 8.459 (13.6)
8,456(8,5); 8,451(4,5); 8,290(11,8); 8,276(15,9)8.456 (8.5); 8.451 (4.5); 8,290 (11.8); 8.276 (15.9)
8,193(10,7); 8,190(10,4); 8,178(11,5); 8,176(14,8)8,193 (10.7); 8,190 (10.4); 8.178 (11.5); 8,176 (14.8)
8,162(6,9); 8,160(6,9); 8,085(0,5); 8,082(0,5)8.162 (6.9); 8,160 (6.9); 8,085 (0.5); 8,082 (0.5)
8,071(0,4); 8,068(0,4); 7,745(6,9); 7,732(14,0)8,071 (0.4); 8,068 (0.4); 7,745 (6.9); 7.732 (14.0)
7,719(8,3); 7,627(8,2); 7,614(6,4); 7,494(0,3)7,719 (8.3); 7.627 (8.2); 7,614 (6.4); 7,494 (0.3)
7,482(0,7); 5,756(2,4); 3,322(541,8); 3,173(1,1)7,482 (0.7); 5,756 (2.4); 3.322 (541.8); 3,173 (1.1)
3,165(1,1); 2,617(2,8); 2,614(3,8); 2,611(2,8)3,165 (1.1); 2,617 (2.8); 2,614 (3.8); 2,611 (2.8)
2,541(1,2); 2,523(7,5); 2,520(9,5); 2,517(10,4)2,541 (1.2); 2,523 (7.5); 2,520 (9.5); 2,517 (10.4)
2,508(219,2); 2,505(439,2); 2,502(581,7); 2,499(428,1) 2,496(208,9); 2,389(2,5); 2,386(3,4); 2,383(2,5) 1,904(1,9); 1,233(1,6); 0,853(0,3); 0,005(0,6) 0,000(15,5); -0,006(0,6) 2,508 (219.2); 2.505 (439.2); 2.502 (581.7); 2,499 (428.1) 2.496 (208.9); 2,389 (2.5); 2,386 (3.4); 2.383 (2.5) 1.904 (1.9); 1,233 (1.6); 0.853 (0.3); 0.005 (0.6) 0.000 (15.5); -0.006 (0.6)
76 1,84 1H-NMR(400,0 MHz, de-DMSO): Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 76 1.84 1 H-NMR (400.0 MHz, de-DMSO): Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
δ = 10,209(0,4); 9,289(2,9); 8,787(2,0); 8,777(2,0); 8,586(0,4); 8,581(0,4); 8,485(1,7); 8,480(2,5); 8,475(1,8); 8,465(1,9); 8,460(2,6); 8,455(1,7); 8,223(3,0); 8,163(3,3); 8,141(3,5); 8,040(0,5); 8,018(0,6); 7,655(2,0); 7,644(2,1); 7,636(2,1); 7,623(2,2); 7,606(0,5); 7,601(0,3); 7,551(2,5); 7,546(2,5); 7,530(2,3); 7,525(2,3); 3,902(16,0); 3,510(0,6); 3,343(457,5); 3,247(7,7); 3,173(0,7); 3,167(0,7); 2,682(0,5); 2,678(1,0); 2,673(1,3); 2,668(1,0); 2,664(0,5); 2,526(3,4); 2,513(76,7); 2,508(162,9); 2,504(229,3); 2,499(170,8); 2,495(81,3); 2,398(0,7); 2,379(0,7); 2,340(0,5); 2,335(0,9); 2,331(1,3); 2,326(0,9); 2,100(0,9); 1,259(0,4); 1,234(0,5); 1,139(0,8); 1,120(1,6); 1,101(0,7); 0,963(3,2); 0,944(5,7); 0,926(2,9); 0,000(7,6)  δ = 10.209 (0.4); 9.289 (2.9); 8,787 (2.0); 8.777 (2.0); 8,586 (0.4); 8,581 (0.4); 8,485 (1.7); 8,480 (2.5); 8,475 (1.8); 8,465 (1.9); 8,460 (2.6); 8.455 (1.7); 8,223 (3.0); 8.163 (3.3); 8,141 (3.5); 8,040 (0.5); 8,018 (0.6); 7.655 (2.0); 7.644 (2.1); 7,636 (2.1); 7,623 (2.2); 7,606 (0.5); 7,601 (0.3); 7,551 (2.5); 7,546 (2.5); 7,530 (2.3); 7,525 (2.3); 3,902 (16.0); 3,510 (0.6); 3.343 (457.5); 3,247 (7.7); 3,173 (0.7); 3,167 (0.7); 2,682 (0.5); 2,678 (1.0); 2,673 (1.3); 2,668 (1.0); 2,664 (0.5); 2,526 (3.4); 2,513 (76.7); 2,508 (162.9); 2.504 (229.3); 2.499 (170.8); 2,495 (81.3); 2,398 (0.7); 2,379 (0.7); 2,340 (0.5); 2,335 (0.9); 2.331 (1.3); 2,326 (0.9); 2,100 (0.9); 1,259 (0.4); 1,234 (0.5); 1,139 (0.8); 1,120 (1.6); 1,101 (0.7); 0.963 (3.2); 0.944 (5.7); 0.926 (2.9); 0.000 (7.6)
77 2,4 1H-NMR(400,0 MHz, de-DMSO): 77 2.4 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,167(9,1); 8,813(8,2); 8,807(8,4); 8,424(2,8); 8,418(3,7); 8,413(2,7); 8,400(2,8); 8,395(3,6); 8,389(2,6); 8,250(5,1); 8,178(5,5); 8,156(5,9); 7,571(4,1); 7,565(4,1); 7,549(3,9); 7,544(3,9); 3,902(16,0); 3,340(335,4); 3,335(434,4); 3,251(13,3); 3,194(0,4); 3,169(1,8); 2,677(1,2); 2,672(1,7); 2,668(1,2); 2,525(3,9); 2,512(99,1); 2,507(210,2); 2,503(296,0); 2,498(221,8); 2,494(107,0); 2,334(1,3); 2,330(1,7); 2,325(1,3); 2,111(1,5); 2,035(0,4); 1,258(0,4); 0,963(5,2); 0,945(9,8); 0,927(5,0); 0,000(9,9); -0,009(0,4)  δ = 9.167 (9.1); 8,813 (8.2); 8,807 (8.4); 8.424 (2.8); 8,418 (3.7); 8.413 (2.7); 8,400 (2.8); 8,395 (3.6); 8.389 (2.6); 8,250 (5.1); 8.178 (5.5); 8,156 (5.9); 7,571 (4.1); 7,565 (4.1); 7,549 (3.9); 7,544 (3.9); 3,902 (16.0); 3.340 (335.4); 3.335 (434.4); 3,251 (13.3); 3,194 (0.4); 3,169 (1.8); 2,677 (1.2); 2,672 (1.7); 2,668 (1.2); 2,525 (3.9); 2,512 (99.1); 2.507 (210.2); 2.503 (296.0); 2.498 (221.8); 2.494 (107.0); 2,334 (1.3); 2,330 (1.7); 2,325 (1.3); 2,111 (1.5); 2,035 (0.4); 1,258 (0.4); 0.963 (5.2); 0.945 (9.8); 0.927 (5.0); 0,000 (9.9); -0.009 (0.4)
78 2,08 1H-NMR(400,0 MHz, de-DMSO): 78 2.08 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,296(2,9); 8,791(2,0); 8,781(2,0); 8,489(1,9); 8,484(2,7); 8,480(1,9); 8,469(2,1); 8,464(2,9); 8,460(2,0); 8,244(2,2); 8,184(2,3); 8,163(2,4); 7,658(2,1); 7,646(2,2); 7,638(2,2); 7,626(2,0); 7,566(1,9); 7,547(1,8); 3,902(16,0); 3,335(306,6); 3,259(6,1); 3,170(1,1); 2,677(1,2); 2,672(1,6); 2,668(1,4); 2,656(2,1); 2,639(4,0); 2,621(2,4); 2,526(3,0); 2,521(4,7); 2,512(79,1); 2,508(169,6); 2,503(239,7); 2,499(178,2); 2,494(84,9); 2,367(1,3); 2,339(1,2); 2,335(1,6); 2,330(1,9); 2,326(1,5); 1,901(4,0); 1,236(0,4); 0,000(9,0)  δ = 9.296 (2.9); 8.791 (2.0); 8.781 (2.0); 8,489 (1.9); 8,484 (2.7); 8,480 (1.9); 8.469 (2.1); 8,464 (2.9); 8,460 (2.0); 8,244 (2.2); 8,184 (2.3); 8.163 (2.4); 7,658 (2.1); 7,646 (2.2); 7.638 (2.2); 7,626 (2.0); 7,566 (1.9); 7,547 (1.8); 3,902 (16.0); 3.335 (306.6); 3,259 (6.1); 3,170 (1.1); 2,677 (1.2); 2,672 (1.6); 2,668 (1.4); 2,656 (2.1); 2,639 (4.0); 2,621 (2.4); 2,526 (3.0); 2,521 (4.7); 2,512 (79.1); 2,508 (169.6); 2.503 (239.7); 2.499 (178.2); 2,494 (84.9); 2,367 (1.3); 2,339 (1.2); 2,335 (1.6); 2,330 (1.9); 2,326 (1.5); 1,901 (4.0); 1,236 (0.4); 0.000 (9.0)
79 2,64 1H-NMR(400,0 MHz, de-DMSO): 79 2.64 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,173(7,2); 8,818(5,9); 8,811(6,4); 8,429(2,1); 8,423(3,1); 8,418(2,3); 8,405(2,2); 8,399(3,1); 8,394(2,3); 8,312(0,4); 8,270(3,2); 8,200(3,1); 8,178(3,4); 7,584(2,7); 7,562(2,5); 3,902(16,0); 3,342(358,8); 3,337(473,3); 3,263(8,4); 3,169(1,0); 2,672(2,0); 2,668(1,8); 2,657(3,2); 2,639(5,4); 2,622(3,3); 2,526(3,5); 2,508(197,5); 2,503(281,5); 2,499(222,6); 2,371(1,7); 2,335(1,9); 2,330(2,2); 1,901(5,4); 1,235(0,4); 0,000(6,0)  δ = 9.173 (7.2); 8.818 (5.9); 8,811 (6.4); 8,429 (2.1); 8,423 (3.1); 8,418 (2.3); 8.405 (2.2); 8,399 (3.1); 8,394 (2.3); 8,312 (0.4); 8,270 (3.2); 8,200 (3.1); 8.178 (3.4); 7,584 (2.7); 7,562 (2.5); 3,902 (16.0); 3.342 (358.8); 3.337 (473.3); 3,263 (8.4); 3,169 (1.0); 2,672 (2.0); 2,668 (1.8); 2,657 (3.2); 2,639 (5.4); 2,622 (3.3); 2,526 (3.5); 2,508 (197.5); 2.503 (281.5); 2.499 (222.6); 2,371 (1.7); 2,335 (1.9); 2,330 (2.2); 1,901 (5.4); 1,235 (0.4); 0,000 (6.0)
80 1,22 'H-NMRCöOl.ö MHz, de-DMSO):  80, 1.22 'H NMR Coö1.10 MHz, de-DMSO):
δ = 10,494(2,6); 9,238(2,2); 9,237(2,3); 9,234(2,3); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] δ = 10.494 (2.6); 9,238 (2.2); 9,237 (2.3); 9.234 (2.3); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
9,233(2,2); 8,744(1,9) 8,742(2,0) 8,737(2,0) 9.233 (2.2); 8.744 (1.9) 8.742 (2.0) 8.737 (2.0)
8,734(2,0); 8,564(2,7) 8,561(2,7) 8,424(1,1)8,734 (2.0); 8.564 (2.7) 8.561 (2.7) 8.424 (1.1)
8,422(1,4); 8,421(1,4) 8,418(1,1) 8,411(1,2)8,422 (1.4); 8.421 (1.4) 8.418 (1.1) 8.411 (1.2)
8,408(1,4); 8,407(1,5) 8,405(1,1) 8,062(2,8)8.408 (1.4); 8.407 (1.5) 8.405 (1.1) 8.062 (2.8)
8,047(3,1); 7,629(1,7) 7,625(1,7) 7,621(1,5)8,047 (3.1); 7.629 (1.7) 7.625 (1.7) 7.621 (1.5)
7,619(1,5); 7,614(2,2) 7,613(2,2) 7,611(2,5)7,619 (1.5); 7.614 (2.2) 7.613 (2.2) 7.611 (2.5)
7,608(1,6); 7,606(1,4); 7,599(1,3) 7,598(1,3)7,608 (1.6); 7,606 (1.4); 7,599 (1.3) 7.598 (1.3)
3,485(1,9); 3,472(3,2); 3,459(2,1); 3,323(113,3)3,485 (1.9); 3,472 (3.2); 3,459 (2.1); 3.323 (113.3)
3,048(16,0); 2,898(2,4); 2,885(3,2); 2,872(2,2)3.048 (16.0); 2,898 (2.4); 2,885 (3.2); 2,872 (2.2)
2,614(0,5); 2,611(0,3); 2,541(0,8); 2,523(0,7)2,614 (0.5); 2,611 (0.3); 2,541 (0.8); 2,523 (0.7)
2,520(0,9); 2,517(0,9); 2,508(23,6); 2,505(49,5)2,520 (0.9); 2,517 (0.9); 2,508 (23.6); 2.505 (49.5)
2,502(66,6); 2,499(49,0): 2,496(23,4); 2,386(0,4)2,502 (66.6); 2,499 (49.0): 2.496 (23.4); 2,386 (0.4)
0,000(1,8) 0.000 (1.8)
81 1,7 'H-NMRCöOl.ö MHz, de-DMSO):  81.sup.17 'H NMRC.sub.10.OMEGA. MHz, de-DMSO):
δ = 10,520(2 ,2); 9,116(1,7); 9,113(2,8); 9,111(1,7) 8,773(3,0) 8,769(3,0); 8,586(2,6); 8,582(2,6) 8,356(1,0) 8,353(1,2); 8,351(1,1) 8,348(0,9) 8,340(1,0) 8,337(1,3); 8,336(1,1) 8,332(0,9) 8,080(2,8) 8,066(3,0); 7,643(1,7) 7,640(1,7) 7,629(1,6) 7,625(1,7); 3,485(1,9) 3,473(3,2) 3,460(2,1) 3,381(0,4); 3,365(0,6) 3,361(0,6) 3,337(448, 8): 3,316(1,3); 3,306(0,4) 3,048(16,0) 2,900(2,4) 2,888(3,2); 2,875(2,2) 2,618(0,4) 2,615(0,5) 2,612(0,4); 2,542(0,6) 2,524(0,8) 2,521(1,1) 2,518(1,1); 2,509(29,2); 2,506(61,0) 2,503(82,1) 2,500(59,6); 2,497(28,2); 2,390(0,4) 2,387(0,5); 2 ,384(0,4); 0,000(2,0)  δ = 10.520 (2, 2); 9,116 (1.7); 9.113 (2.8); 9.111 (1.7) 8.773 (3.0) 8.769 (3.0); 8,586 (2.6); 8.582 (2.6) 8.356 (1.0) 8.353 (1.2); 8.351 (1.1) 8.348 (0.9) 8.340 (1.0) 8.337 (1.3); 8.366 (1.1) 8.322 (0.9) 8.080 (2.8) 8.066 (3.0); 7.643 (1.7) 7.640 (1.7) 7.629 (1.6) 7.625 (1.7); 3.485 (1.9) 3.473 (3.2) 3.460 (2.1) 3.381 (0.4); 3.365 (0.6) 3.361 (0.6) 3.337 (448, 8): 3.316 (1.3); 3.306 (0.4) 3.048 (16.0) 2.900 (2.4) 2.888 (3.2); 2.875 (2.2) 2.618 (0.4) 2.615 (0.5) 2.612 (0.4); 2.542 (0.6) 2.524 (0.8) 2.521 (1.1) 2.518 (1.1); 2,509 (29.2); 2.506 (61.0) 2.503 (82.1) 2.500 (59.6); 2,497 (28.2); 2.390 (0.4) 2.387 (0.5); 2, 384 (0.4); 0.000 (2.0)
82 1,49 1H-NMR(400,0 MHz, de-DMSO): 82 1.49 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,303(1,4); 8,796(1,0); 8,787(1,0); 8,497(0,8) δ = 9.303 (1.4); 8,796 (1.0); 8,787 (1.0); 8,497 (0.8)
8,492(1,2); 8,487(0,8) 8,477(0,9); 8,472(1,3)8.492 (1.2); 8.487 (0.8) 8.477 (0.9); 8,472 (1.3)
8,467(0,9); 8,299(1,3) 8,217(0,9); 8,196(1,0)8,467 (0.9); 8.299 (1.3) 8.217 (0.9); 8.196 (1.0)
7,663(1,0); 7,651(1,1) 7,643(1,2); 7,631(1,6)7,663 (1.0); 7.651 (1.1) 7.643 (1.2); 7,631 (1.6)
7,613(0,7); 3,902(16,0) 3,336(187,0); 3,259(4,7)7,613 (0.7); 3.902 (16.0) 3.336 (187.0); 3.259 (4.7)
3,227(0,8); 3,205(0,7) 3,185(0,7); 3,169(5,1)3,227 (0.8); 3.205 (0.7) 3.185 (0.7); 3,169 (5.1)
3,137(2,2); 3,116(1,3) 2,981(0,6); 2,954(0,5)3,137 (2.2); 3.161 (1.3) 2.981 (0.6); 2,954 (0.5)
2,930(0,4); 2,676(0,5); 2,672(0,7); 2,667(0,6)2,930 (0.4); 2,676 (0.5); 2,672 (0.7); 2.667 (0.6)
2,525(1,6); 2,520(2,5); 2,512(42,0); 2,507(91,5)2,525 (1.6); 2,520 (2.5); 2,512 (42.0); 2.507 (91.5)
2,503(130,2): 2,498(96,3); 2,494(45,1); 2,334(0,6)2.503 (130.2): 2.498 (96.3); 2,494 (45.1); 2,334 (0.6)
2,330(0,8); 2,325(0,6); 2,171(0,3); 2,147(0,6)2,330 (0.8); 2,325 (0.6); 2,171 (0.3); 2,147 (0.6)
2,124(0,7); 2,101(0,6); 0,000(2,9) 2,124 (0.7); 2,101 (0.6); 0.000 (2.9)
83 1,94 1H-NMR(400,0 MHz, de-DMSO): 83 1.94 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,179(2,0); 8,821(1,7); 8,815(1,8); 8,431(0,8) 8,409(0,8); 8,321(1,0); 8,233(0,7); 8,211(0,8) 7,650(0,6); 7,629(0,6); 3,901(16,0); 3,355(281,1) 3,261(3,9); 3,170(1,3); 3,138(1,8); 3,117(1,1) δ = 9.179 (2.0); 8,821 (1.7); 8.815 (1.8); 8.431 (0.8) 8.409 (0.8); 8,321 (1.0); 8,233 (0.7); 8,211 (0.8) 7,650 (0.6); 7,629 (0.6); 3,901 (16.0); 3.355 (281.1) 3.261 (3.9); 3,170 (1.3); 3,138 (1.8); 3.117 (1.1)
2,951(0,4); 2,925(0,4); 2,673(0,7); 2,508(81,8) 2,504(113,1); 2,499(91,0); 2,330(0,6); 2,147(0,5) 2,126(0,6); 2,103(0,5); 0,000(0,7) 2,951 (0.4); 2,925 (0.4); 2,673 (0.7); 2.508 (81.8) 2.504 (113.1); 2,499 (91.0); 2,330 (0.6); 2.147 (0.5) 2.126 (0.6); 2,103 (0.5); 0.000 (0.7)
84 3,24 1H-NMR(400,0 MHz, de-DMSO): 84 3.24 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,234(2,3); 8,765(1,6); 8,753(1,6); 8,436(1,3); 8,431(1,8); 8,426(1,4); 8,416(1,4); 8,410(2,0); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] δ = 9.234 (2.3); 8,765 (1.6); 8,753 (1.6); 8.436 (1.3); 8,431 (1.8); 8,426 (1.4); 8,416 (1.4); 8,410 (2.0); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
8,406(1,5); 8,105(3,3); 8,100(3,5); 7,992(3,4); 7,970(3,7); 7,630(1,5); 7,618(1,9); 7,610(3,1); 7,599(3,5); 7,588(2,7); 7,581(5,4); 7,454(2,0); 7,449(3,1); 7,427(3,9); 7,409(1,1); 3,907(16,0); 3,476(22,2); 3,368(747,9); 3,274(0,8); 3,175(1,8); 2,683(0,9); 2,679(1,2); 2,674(0,9); 2,532(3,1); 2,519(68,2); 2,514(145,0); 2,510(203,9); 2,505(151,2); 2,501(71,2); 2,341(0,8); 2,337(1,1); 2,332(0,8) 8,406 (1.5); 8,105 (3.3); 8,100 (3.5); 7,992 (3.4); 7,970 (3.7); 7,630 (1.5); 7,618 (1.9); 7,610 (3.1); 7,599 (3.5); 7,588 (2.7); 7,581 (5.4); 7,454 (2.0); 7,449 (3.1); 7,427 (3.9); 7,409 (1.1); 3,907 (16.0); 3,476 (22.2); 3.368 (747.9); 3,274 (0.8); 3.175 (1.8); 2,683 (0.9); 2,679 (1.2); 2,674 (0.9); 2,532 (3.1); 2,519 (68.2); 2.514 (145.0); 2,510 (203.9); 2.505 (151.2); 2,501 (71.2); 2,341 (0.8); 2,337 (1.1); 2.332 (0.8)
85 3,88 1H-NMR(400,0 MHz, de-DMSO): 85 3.88 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,117(2,8); 9,113(4,5); 9,109(3,3); 8,787(4,0); 8,781(4,4); 8,373(1,4); 8,366(1,9); 8,361(1,7); 8,349(1,7); 8,345(1,9); 8,338(1,6); 8,128(3,5); 8,123(3,9); 8,004(3,1); 7,983(3,5); 7,604(2,1); 7,585(4,6); 7,575(5,7); 7,469(1,9); 7,464(2,2); 7,447(2,4); 7,442(3,6); 7,422(2,5); 7,403(1,2); 3,902(16,0); 3,473(20,2); 3,330(581,9); 3,169(0,8); 2,676(1,1); 2,671(1,5); 2,667(1,3); 2,511(104,1); 2,507(192,5); 2,502(260,0); 2,498(220,1); 2,493(137,4); 2,333(1,1); 2,329(1,5); 2,324(1,2); 1,258(0,4); 1,235(0,4); -0,001(10,7)  δ = 9.117 (2.8); 9.113 (4.5); 9,109 (3.3); 8,787 (4.0); 8.781 (4.4); 8.373 (1.4); 8,366 (1.9); 8,361 (1.7); 8,349 (1.7); 8.345 (1.9); 8,338 (1.6); 8.128 (3.5); 8.123 (3.9); 8,004 (3.1); 7,983 (3.5); 7,604 (2.1); 7,585 (4.6); 7,575 (5.7); 7.469 (1.9); 7,464 (2.2); 7,447 (2.4); 7.442 (3.6); 7,422 (2.5); 7,403 (1.2); 3,902 (16.0); 3,473 (20.2); 3.330 (581.9); 3,169 (0.8); 2,676 (1.1); 2,671 (1.5); 2,667 (1.3); 2,511 (104.1); 2.507 (192.5); 2.502 (260.0); 2.498 (220.1); 2,493 (137.4); 2,333 (1.1); 2,329 (1.5); 2,324 (1.2); 1,258 (0.4); 1,235 (0.4); -0.001 (10.7)
86 2,63 'H-NMRCöOl.ö MHz, de-DMSO):  86 2.63 'H-NMRCöOl.ö MHz, de-DMSO):
δ = 10,790(4,7); 9,556(0,4); 8,800(9,3); 8,798(15,1); 8,795(9,5); 8,747(15,4); 8,744(15,3); 8,730(0,3); 8,481(0,4); 8,390(8,2); 8,388(8,1); 8,379(8,4); 8,378(8,4); 8,376(7,3); 8,329(14,7); 8,295(0,4); 8,289(0,4); 8,247(8,0); 8,234(8,2); 8,140(14,0); 8,125(16,0); 7,985(7,0); 7,969(11,5); 7,968(10,4); 7,955(7,6); 7,954(8,9); 7,953(9,2); 7,923(0,4); 7,885(9,4); 7,881(9,0); 7,870(8,8); 7,867(8,7); 7,767(8,1); 7,754(14,9); 7,742(7,1); 7,620(7,9); 7,609(9,0); 7,607(9,0); 7,596(7,3); 3,903(0,4); 3,324(873,2); 2,891(1,7); 2,731(1,3); 2,617(2,5); 2,614(3,4); 2,611(2,5); 2,541(12,9); 2,523(6,2); 2,520(7,8); 2,517(8,3); 2,508(189,3); 2,505(388,8); 2,502(518,7); 2,499(386,3); 2,496(188,4); 2,389(2,5); 2,386(3,4); 2,383(2,5); 1,586(0,8); 0,000(10,1) δ = 10.790 (4.7); 9,556 (0.4); 8,800 (9.3); 8,798 (15.1); 8.795 (9.5); 8,747 (15.4); 8.744 (15.3); 8,730 (0.3); 8.481 (0.4); 8,390 (8.2); 8,388 (8.1); 8,379 (8.4); 8,378 (8.4); 8,376 (7.3); 8.329 (14.7); 8,295 (0.4); 8,289 (0.4); 8.247 (8.0); 8,234 (8.2); 8,140 (14.0); 8,125 (16.0); 7,985 (7.0); 7,969 (11.5); 7,968 (10.4); 7,955 (7.6); 7,954 (8.9); 7.953 (9.2); 7,923 (0.4); 7,885 (9.4); 7,881 (9.0); 7,870 (8.8); 7,867 (8.7); 7,767 (8.1); 7,754 (14.9); 7,742 (7.1); 7,620 (7.9); 7,609 (9.0); 7,607 (9.0); 7,596 (7.3); 3,903 (0.4); 3.324 (873.2); 2,891 (1.7); 2,731 (1.3); 2,617 (2.5); 2,614 (3.4); 2,611 (2.5); 2,541 (12.9); 2,523 (6.2); 2,520 (7.8); 2,517 (8.3); 2,508 (189.3); 2.505 (388.8); 2.502 (518.7); 2.499 (386.3); 2.496 (188.4); 2,389 (2.5); 2,386 (3.4); 2,383 (2.5); 1.586 (0.8); 0.000 (10.1)
87 3,27 1H-NMR(400,0 MHz, de-DMSO): 87 3.27 1 H-NMR (400.0 MHz, de-DMSO):
δ = 10,872(5,4); 9,144(5,1); 8,790(4,5); 8,784(4,7); 8,742(4,7); 8,737(4,9); 8,480(4,4); 8,400(2,5); 8,392(2,1); 8,385(3,5); 8,381(4,2); 8,368(1,8); 8,364(2,1); 8,357(1,6); 8,155(4,7); 8,145(2,3); 8,133(6,0); 7,949(2,7); 7,929(4,7); 7,910(2,2); 7,900(3,0); 7,895(2,9); 7,878(2,5); 7,873(2,6); 3,902(16,0); 3,508(0,5); 3,347(608,9); 3,344(633,8); 3,176(1,4); 3,163(1,4); 2,677(1,2); 2,673(1,6); 2,668(1,2); 2,543(1,4); 2,526(4,5); 2,512(97,0); 2,508(204,5); 2,503(286,3); 2,499(216,7); 2,495(106,2); 2,335(1,2); 2,330(1,6); 2,326(1,2); 1,249(0,3); 1,235(0,5); 0,008(0,3); 0,000(9,6)  δ = 10.872 (5.4); 9.144 (5.1); 8,790 (4.5); 8.784 (4.7); 8,742 (4.7); 8,737 (4.9); 8,480 (4.4); 8,400 (2.5); 8,392 (2.1); 8,385 (3.5); 8,381 (4.2); 8,368 (1.8); 8,364 (2.1); 8,357 (1.6); 8.155 (4.7); 8.145 (2.3); 8,133 (6.0); 7,949 (2.7); 7.929 (4.7); 7.910 (2.2); 7,900 (3.0); 7.895 (2.9); 7,878 (2.5); 7,873 (2.6); 3,902 (16.0); 3,508 (0.5); 3.347 (608.9); 3,344 (633.8); 3,176 (1.4); 3,163 (1.4); 2,677 (1.2); 2,673 (1.6); 2,668 (1.2); 2,543 (1.4); 2,526 (4.5); 2,512 (97.0); 2,508 (204.5); 2.503 (286.3); 2.499 (216.7); 2.495 (106.2); 2,335 (1.2); 2,330 (1.6); 2,326 (1.2); 1,249 (0.3); 1,235 (0.5); 0.008 (0.3); 0.000 (9.6)
I-a-2 3,37 3,39 1H-NMR(400,0 MHz, de-DMSO): Ia-2 3.37 3.39 1 H-NMR (400.0 MHz, de-DMSO):
δ = 9,271(8,0); 9,267(8,2); 8,777(6,0); 8,774(6,4); Bsp.-Nr. logP[a] logP[b] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] δ = 9.271 (8.0); 9,267 (8.2); 8.777 (6.0); 8,774 (6.4); Expl logP [a] logP [b] 1H-NMR [σ (ppm)] or LC-MS [m / z]
8,765(6,4); 8,762(6,3); 8,657(10,6); 8,654(10,4); 8,470(3,5); 8,466(4,8); 8,460(3,5); 8,450(3,8); 8,445(5,0); 8,440(3,6); 7,915(3,5); 7,894(16,0); 7,884(11,4); 7,880(10,7); 7,863(2,4); 7,859(2,6); 7,639(4,4); 7,637(4,3); 7,627(4,4); 7,625(4,3); 7,619(4,4); 7,607(4,2); 7,605(4,0); 3,329(37,2); 2,893(0,3); 2,678(0,5); 2,673(0,6); 2,669(0,5); 2,527(1,4); 2,509(74,3); 2,504(98,2); 2,500(71,8); 2,335(0,5); 2,331(0,7); 2,327(0,5); 0,008(0,9); 0,000(26,8); -0,008(1,1)  8,765 (6.4); 8.762 (6.3); 8.657 (10.6); 8,654 (10.4); 8,470 (3.5); 8,466 (4.8); 8,460 (3.5); 8,450 (3.8); 8,445 (5.0); 8,440 (3.6); 7.915 (3.5); 7,894 (16.0); 7,884 (11.4); 7,880 (10.7); 7,863 (2.4); 7,859 (2.6); 7,639 (4.4); 7,637 (4.3); 7.627 (4.4); 7,625 (4.3); 7,619 (4.4); 7,607 (4.2); 7,605 (4.0); 3,329 (37.2); 2,893 (0.3); 2,678 (0.5); 2,673 (0.6); 2,669 (0.5); 2,527 (1.4); 2,509 (74.3); 2,504 (98.2); 2,500 (71.8); 2,335 (0.5); 2.331 (0.7); 2,327 (0.5); 0.008 (0.9); 0,000 (26.8); -0.008 (1.1)
I-h-1 4,03 4,14 ^-NMR^OO.O MHZ, de-DMSO):  I-h-1 4.03 4.14 ^ -NMR ^ OO.O MHZ, de-DMSO):
δ = 9,291(0,7); 9,286(0,8); 8,782(0,5); 8,778(0,5); 8,770(0,5); 8,766(0,5); 8,514(1,2); 8,487(0,4); 8,467(0,4); 8,114(0,8); 8,093(0,9); 7,930(1,2); 7,843(0,6); 7,823(0,5); 7,646(0,4); 7,634(0,4); 7,626(0,4); 7,614(0,4); 3,927(2,3); 3,325(10,2); 2,509(8,2); 2,504(10,7); 2,500(7,9); 1,342(15,3); 1,168(1,5); 1,160(16,0); 1,072(15,9)  δ = 9.291 (0.7); 9.286 (0.8); 8.782 (0.5); 8,778 (0.5); 8,770 (0.5); 8.766 (0.5); 8,514 (1.2); 8,487 (0.4); 8,467 (0.4); 8,114 (0.8); 8,093 (0.9); 7,930 (1.2); 7,843 (0.6); 7,823 (0.5); 7,646 (0.4); 7,634 (0.4); 7,626 (0.4); 7,614 (0.4); 3,927 (2.3); 3,325 (10.2); 2,509 (8.2); 2,504 (10.7); 2,500 (7.9); 1,342 (15.3); 1.168 (1.5); 1,160 (16.0); 1.072 (15.9)
Biologische Beispiele Biological examples
Boophilus microplus -Injektionstest Boophilus microplus injection test
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Lösungsmittel und verdünnt das Konzentrat mit Lösungsmittel auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.
1 μΐ der Wirkstofflösung wird in das Abdomen von 5 vollgesogenen, adulten, weiblichen Rinderzecken (Boophilus microplus) injiziert. Die Tiere werden in Schalen überführt und in einem klimatisierten Raum aufbewahrt. 1 μΐ of the drug solution is injected into the abdomen of 5 adult, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room.
Die Wirkungskontrolle erfolgt nach 7 Tagen auf Ablage fertiler Eier. Eier, deren Fertilität nicht äußerlich sichtbar ist, werden bis zum Larvenschlupf nach etwa 42 Tagen im Klimaschrank aufbewahrt. Eine Wirkung von 100 % bedeutet, dass keine der Zecken fertile Eier gelegt hat, 0% bedeutet, dass alle Eier fertil sind. The effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 20μg/Tier: 29 In this test, e.g. the following compounds of the preparation examples have an effect of 100% at an application rate of 20 μg / animal: 29
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 20μg/Tier: 28, 25 Myzus persicae - Sprühtest In this test, for example, the following compounds of the preparation examples show an effect of 80% at an application rate of 20 μg / animal: 28, 25 Myzus persicae - spray test
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Chinakohlblattscheiben {Brassica pekinensis), die von allen Stadien der Grünen Pfirsichblattlaus {Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid {Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeuten 100 %>, dass alle Blattläuse abgetötet wurden und 0 %>, dass keine Blattläuse abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 500g/ha: 2, 4, 7, 28, 32, 33, 39, 42, 47, 51 , 57, 58, 59, 60, 61, 62, 65, 66, 68, 71, 78, 79 After 6 days, the effect is determined in%. 100%> means that all aphids have been killed and 0%> that no aphids have been killed. In this test, z. Example, the following compounds of the manufacturing examples effect of 100% at a rate of 500g / ha: 2, 4, 7, 28, 32, 33, 39, 42, 47, 51, 57, 58, 59, 60, 61, 62nd , 65, 66, 68, 71, 78, 79
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 500g/ha: 3, 9, 10, 11, 12, 13, 18, 20, 25, 27, 29, 30, 34, 35, 37, 45, 46, 48, 49, 50, 56, 64, 67, 69, 70, 72, 82 In this test, z. Example, the following compounds of the preparation examples effect of 90% at a rate of 500g / ha: 3, 9, 10, 11, 12, 13, 18, 20, 25, 27, 29, 30, 34, 35, 37, 45 , 46, 48, 49, 50, 56, 64, 67, 69, 70, 72, 82
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 20g/ha: 80 In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 20g / ha: 80
Phaedon cochleariae - Sprühtest Phaedon cochleariae - spray test
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Emulsifier: alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
Chinakohlblattscheiben (Brassica pekinensis) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Larven des Meerrettichblattkäfers (Phaedon cochleariae) besetzt. Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeuten 100 %, dass alle Käferlarven abgetötet wurden und 0 %, dass keine Käferlarven abgetötet wurden. After 7 days, the effect is determined in%. 100% means that all beetle larvae were killed and 0% that no beetle larvae were killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83% bei einer Aufwandmenge von 500g/ha: 7, 8 In this test, z. Example, the following compounds of the preparation examples effect of 83% at a rate of 500g / ha: 7, 8
Tetranychus urticae - Sprühtest, OP-resistent Tetranychus urticae - spray test, op-resistant
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator : Alkylarylpolyglykolether Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeuten 100 %, dass alle Spinnmilben abgetötet wurden und 0 %, dass keine Spinnmilben abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 500g/ha: 2 After 6 days, the effect is determined in%. 100% means that all spider mites have been killed and 0% that no spider mites have been killed. In this test, z. For example, the following compounds of the preparation examples have an effect of 90% at an application rate of 500 g / ha: 2

Claims

Patentansprüche: claims:
1. Verbindungen der Formel (I) 1. Compounds of the formula (I)
in welcher A für einen A-Rest aus der Reihe (A-b) bis (A-f) in which A is an A radical from the series (Ab) to (Af)
(A-b) (A-c) (A-d) (A-e) (A-f) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet und für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyl steht, für Sauerstoff oder Schwefel steht, für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkoxy und Cyano steht, a) für einen B-Rest aus der Reihe  (Ab) (Ac) (Ad) (Ae) (Af), in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I) and a radical selected from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, Haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl, represents oxygen or sulfur, is a radical from the series hydrogen, alkyl, alkoxy and cyano, a) is a B radical from the series
(B-5) (B-6) (B-7) (B-8) (B-5) (B-6) ( B-7) (B-8)
(B-9) (B-10) (B-11) (B-12)  (B-9) (B-10) (B-11) (B-12)
(B-29) (B-30) (B-31) (B-32) (B-29) (B-30) (B-31) (B-32)
(B-33) (B-35) (B-36) (B-37) (B-33) (B-35) (B-36) (B-37)
(B-38) (B-39) (B-40) (B-41 ) (B-38) (B-39) (B-40) (B-41)
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder (B-42) (B-43) (B-44) (B-45), wherein the broken line represents the bond to the carbon atom of the bicycle of the formula (I), or
R b) für einen D-Rest aus der Reihe (D- 1 ) bis (D-3) R b) for a D radical from the series (D-1) to (D-3)
(D-1 ) (D-2) (D-3) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder c) für einen Rest der Formel  (D-1) (D-2) (D-3), wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or c) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R2 d) für einen Rest der Formel wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or R 2 d) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R e) für einen F-Rest aus der Reihe (F-1) bis (F-11)  in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I), or R e) represents an F radical from the series (F-1) to (F-11)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder  wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R f) für einen Rest der Formel 22 R f) is a radical of the formula 22
ΊΜ ' ΊΜ '
I  I
R steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder g) für gegebenenfalls substituiertes Phenyl steht, worin für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, Alkyl, Halogenalkyl, gegebenenfalls substituiertes und gegebenenfalls durch ein oder mehrere Heteroatome unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, halogeniertes Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Bis(alkoxy)alkyl, R is, in which the dashed line represents the bond to the carbon atom of the bicyclic compound of the formula (I), or g) represents optionally substituted phenyl in which hydrogen or a radical from the group halogen, nitro, amino, cyano, alkylamino, haloalkylamino, Dialkylamino, alkyl, haloalkyl, optionally substituted and optionally interrupted by one or more heteroatoms saturated or unsaturated cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, bis (alkoxy) alkyl,
Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl, Alkoxy(alkylsulfinyl)alkyl,Bis (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl, alkoxy (alkylsulfinyl) alkyl,
Alkoxy(alkylsulfonyl)alkyl, Bis(alkylsulfanyl)alkyl, Bis(halogenalkylsulfanyl)alkyl,Alkoxy (alkylsulfonyl) alkyl, bis (alkylsulfanyl) alkyl, bis (haloalkylsulfanyl) alkyl,
Bis(hydroxyalkylsulfanyl)alkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, alpha-Hydroxyimino- alkoxycarbonylalkyl, alpha-Alkoxyimino-alkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl,die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Alkyl, Halogenalkyl, Alkoxy und Alkoxyalkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Alkyl und Halogenalkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthio, Alkylthioalkyl und Cycloalkyl) und die Heteroarylalkylreste Triazolylalkyl, Pyridylalkyl, Pyrimidylalkyl und Oxadiazolylalkyl (welche selbst wiederum substituiert sein können durch Halogen und Alkyl) steht, oder für einen C-Rest aus der Reihe (C-l) bis (C-9) » Bis (hydroxyalkylsulfanyl) alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyiminoalkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, morpholinyl, Triazolinonyl, oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl , Dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may themselves be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which in turn may be substituted by halogen, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals pyridyl, pyridyl-N oxide, pyrimidyl, imi dazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may be substituted by halo, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio , Alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which in turn may themselves be substituted by halogen and alkyl), or represents a C radical from the series (Cl) to (C-9) »
X (C-9) X (C-9)
R8 steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, R 8 is where the dotted line represents the bond to the B residues,
X für Sauerstoff oder Schwefel steht,  X is oxygen or sulfur,
X1 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, X 1 is a radical selected from among hydrogen, halogen, cyano, nitro, alkyl, haloalkyl,
Cycloalkyl, Alkoxy und Halogenalkoxy steht,  Cycloalkyl, alkoxy and haloalkoxy,
X2 für Sauerstoff, Schwefel, NR5 oder NOH steht, X 2 is oxygen, sulfur, NR 5 or NOH,
L für Sauerstoff oder Schwefel steht, L is oxygen or sulfur,
V-Z für R24CH-CHR25 oder R24C=CR25 steht, n für 1 oder 2 steht, m für 1 , 2, 3 oder 4 steht, VZ is R 24 CH-CHR 25 or R 24 C = CR 25 , n is 1 or 2, m is 1, 2, 3 or 4,
R für NR18R19 oder für einen jeweils gegebenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkyl-S-alkyl, Alkyl-S(0)-alkyl, Alkyl-S(0)2-alkyl, R18-CO-alkyl, NR18R19-CO-alkyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkenylalkyl, Heterocyclyl, Heterocyclylalkyl, Phenyl, Phenylalkyl, Hetaryl und Hetarylalkyl steht, R is NR 18 R 19 or represents a respectively optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S (0) -alkyl, alkyl-S (0) 2 alkyl, R 18 -CO-alkyl, NR 18 R 19 is -CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl,
R3 für Wasserstoff oder Alkyl steht, R 3 is hydrogen or alkyl,
R4 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, R5 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder R 4 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl, R 5 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
R3 und R4 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, oder R 3 and R 4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, or
R3 und R5 gemeinsam mit den Stickstoffatomen, an die sie gebunden sind, einen Ring bilden, R6 für Wasserstoff oder Alkyl steht, R 3 and R 5 together with the nitrogen atoms to which they are attached form a ring, R 6 is hydrogen or alkyl,
R7 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder R 7 is a radical selected from hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, R 6 and R 7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
R8 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkoxy, Halogenalkoxy, Alkenyl, Alkoxyalkyl, jeweils gegebenenfalls durch Halogen substituiertes Alkylcarbonyl und Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonyl und gegebenenfalls durch Halogen, Alkyl, Alkoxy, Halogenalkyl und Cyano substituiertes Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch Alkyl oder Arylalkyl substituiertes Ammonium-Ion steht, R 8 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl and optionally by halogen, alkyl, alkoxy, haloalkyl and cyano is substituted cycloalkylcarbonyl, or represents a cation or an optionally substituted by alkyl or arylalkyl ammonium ion,
R9 für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 9 is a radical from the series in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
8 9 8 9
R und R in den Resten (C-l) und (F-l) auch zusammen mit der N-S(0)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R für Wasserstoff oder Alkyl steht, R and R in the radicals (Cl) and (Fl) may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the or a plurality of further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group, R is hydrogen or alkyl,
R8 und R10 in den Resten (C-2) und (F-2) auch gemeinsam mit den N- Atomen an die sie gebunden sind, für einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring stehen können, der mindestens ein weiteres Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R 8 and R 10 in the radicals (C-2) and (F-2) may also together with the N atoms to which they are bonded represent a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the at least one further heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
9 10 9 10
R und R in den Resten (C-2) und (F-2) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R and R in the radicals (C-2) and (F-2) may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
RU für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht, R U is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio stands,
12 12
R für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht,  R represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio .
11 12 11 12
R und R in den Resten (C-3) und (F-3) auch gemeinsam mit dem Phosphoratom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 5- bis 7-gliedrigen Ring bilden können, der ein oder zwei Heteroatome aus der Reihe Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Schwefel enthalten kann,  R and R in the radicals (C-3) and (F-3) may also together with the phosphorus atom to which they are attached form a saturated or unsaturated and optionally substituted 5- to 7-membered ring, one or two Heteroatoms from the series oxygen (oxygen atoms may not be immediately adjacent) and may contain sulfur,
13 13
R für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,  R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
14 14
R für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,  R is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R15 für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 15 is a radical from the series each optionally substituted alkyl, alkenyl and alkynyl, each optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be included, respectively substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R8 und R15 in den Resten (C-6) und (F-6) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel,R 8 and R 15 in the radicals (C-6) and (F-6) also together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring can form one or more other heteroatoms from the series sulfur,
Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, Oxygen (where oxygen atoms are not immediately adjacent) and may contain nitrogen and / or at least one carbonyl group, a radical selected from the group consisting of hydrogen, each optionally substituted alkyl, alkoxy, alkenyl and alkynyl, respectively optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in in which each of the rings is at least one heteroatom selected from the group consisting of sulfur, oxygen (where oxygen atoms are not immediately adjacent) and nitrogen, optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R" und R16 in den Resten (C-7) und (F-7) auch zusammen mit dem N-Atom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R8 und R17 in den Resten (C-8) und (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R18 für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkylcarbonyl, Alkoxycarbonyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl und Cycloalkenylalkyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Arylalkyl, Heteroaryl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R " and R 16 in the radicals (C-7) and (F-7) together with the N-atom to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or more other heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group, a radical from the series each optionally substituted alkyl, alkoxy, alkenyl and alkynyl, respectively optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl in which the rings may contain at least one heteroatom selected from sulfur, oxygen (where oxygen atoms are not immediately adjacent) and nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group R 8 and R 17 in the radicals (C-8) and (F-8) also together with the NC (X) group to which they are attached may form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or more further heteroatoms selected from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent ) and nitrogen and / or at least one carbonyl group, R 18 is a radical selected from hydrogen, hydroxy, each optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, each optionally substituted Cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the rings at least one Heteroatom from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group,
R19 für einen Rest aus der Reihe Wasserstoff, für ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch Ci-C i-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl und Alkylsulfonylalkyl steht, R 19 is a radical selected from the group consisting of hydrogen, an alkali metal or alkaline earth metal ion or an optionally monosubstituted to trisubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or an optionally halogen or cyano-substituted radical from the series consisting of alkyl, alkoxy, Alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl,
Y1 und Y2 unabhängig voneinander für C=0 oder S(0)2 stehen, Y 1 and Y 2 independently of one another represent C = 0 or S (O) 2,
Y3 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und NR20R21 steht, Y 3 is a radical from the group consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR 20 R 21 ,
W für einen Rest aus der Reihe O, S, SO und SO2 steht, W is a radical from the series O, S, SO and SO2,
R22 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkenyl, Halogenalkenyl, Alkinyl, Halogenalkinyl, Alkoxy, Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Alkoxyalkyl, gegebenenfalls durch Halogen substituiertes Bis(alkoxy)alkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfanylalkyl, gegebenenfalls durch Halogen substituiertes Alkylcarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfinylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfonylalkyl, Dialkylaminosulfanylalkyl, Dialkylaminosulfinylalkyl, Dialkylaminosulfonylalkyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkinyloxy, gegebenenfalls durch Halogen substituiertes Alkinyloxycarbonyl, Dialkylaminocarbonyl, N-Alkyl-N-Cycloalkylaminocarbonyl, Dialkylaminocarbonylalkyl, N-Alkyl-N-Cycloalkylaminocarbonylalkyl, Heterocyclyl- carbonylalkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkylalkyl, gegebenenfalls substituiertes Heterocyclyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclylalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist)Alkoxy oder Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Amino, Alkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Halogenalkyl, Alkoxy oder Halogenalkoxy substituiertes Arylalkyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetarylalkyl steht, oder für einen D-Rest aus der Reihe (D-l) bis (D-3) R 22 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis (alkoxy) alkyl, optionally halogen-substituted alkylsulfanylalkyl, alkylcarbonylalkyl optionally substituted by halogen, optionally alkyl substituted by halogen, alkylsulphonylalkyl optionally substituted by halogen, dialkylaminosulphanylalkyl, dialkylaminosulphinylalkyl, dialkylaminosulphonylalkyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-substituted alkoxycarbonylalkyl, optionally halogen-substituted alkynyloxy, optionally halogen-substituted alkynyloxycarbonyl, dialkylaminocarbonyl, N-alkyl-N-cycloalkylaminocarbonyl, dialkylaminocarbonylalkyl, N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonyl lalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, optionally substituted by halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkyl optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkylcarbonyl, optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, Cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, Hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, Alkylcarbonyl, alkoxycarbonyl or aminocarbonyl-substituted heterocyclylalkyl, optionally substituted by halogen, cyano, nitro, hydroxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted) alkoxy or haloalkoxy-substituted aryl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, Hydroxy, amino, alkyl, cycloalkyl (which is optionally substituted), haloalkyl, alkoxy or haloalkoxy-substituted arylalkyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy , Haloalkoxy, alkylth io, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl-substituted hetarylalkyl, or a D radical from the series (D1) to (D-3)
(D-1 ) (D-2) (D-3) für einen E-Rest aus der Reihe (E-l) bis (E-l 1) (D-1) (D-2) (D-3) for an E group from the series (El) to (El 1)
E-26 -265 - E-26 -265 -
E-37 E-38 E-39 E-40  E-37 E-38 E-39 E-40
E-44 E-45 E-46 E-47 E-44 E-45 E-46 E-47
E-48 E-49 E-50 E-51 steht, oder  E-48 E-49 E-50 E-51 stands, or
im Fall, dass R2 für einen der Reste unter d) steht in the case where R 2 is one of the radicals under d)
auch für einen E-Rest aus der Reihe E-12 bis E-17  also for an E-rest from the series E-12 to E-17
E-16 steht, für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy und jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylcarbonyloxy, Alkenylcarbonyloxy, Alkinylcarbonyloxy, Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Alkylsulfonyloxy, Alkylamino, Alkenylamino, Alkinylamino, Cycloalkylamino, Alkylthio, Halogenalkylthio, Alkenylthio, Alkinylthio, Cycloalkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylcarbonyl, Alkoxyiminoalkyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl,E-16 is a radical selected from among hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy , Alkylsulfonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Dialkylaminocarbonyl, Aminothiocarbonyl, Alkylaminosulfonyl, Alkylsulfonylamino, Alkylcarbonylamino, Alkenylcarbonylamino, Alkinylcarbonylamino, Cycloalkylcarbonylamino, Alkoxycarbonylamino, Alkylthiocarbonylamino, Bicycloalkyl, Aryl, Aryloxy, Heteroaryl und Heteroaryloxy steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl und Halogenalkyl, für einen Rest aus der Reihe Wasserstoff, Alkyl, Cycloalkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Cyanoalkyl, Alkylcarbonyl, Alkenylcarbonyl, Halogenalkylcarbonyl, Halogenalkenylcarbonyl, Alkoxyalkyl, Alkoxycarbonyl, Alkylsulfonyl und Halogenalkylsulfonyl steht, für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylthioalkyl, Alkenylthioalkyl, Cyanoalkyl und Alkoxyalkyl steht oder, im Fall, dass R2 für einen der Reste unter c) oder f) steht und R23 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, und für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht und für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht, für Wasserstoff oder Alkyl steht und Dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, wherein the substituents are independently selected from halo, cyano, nitro, hydroxy, amino, alkyl and haloalkyl, a radical selected from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl, a radical selected from the group consisting of hydrogen, Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl and alkoxyalkyl or, in the case where R 2 is one of the radicals under c) or f) and R 23 is taken together with the nitrogen to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, and represents hydrogen or an optionally substituted radical selected from alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and is hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, is hydrogen or alkyl and
R für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy-alkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl Cyanoalkyl steht, und Verbindungen der Formel (I), in welcher A für den A-Rest (A-a) R is a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, Haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cyanoalkyl, and compounds of the formula (I) in which A is the A radical (Aa)
T  T
(A-a) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet und  (A-a), wherein the dotted line represents the bond to the carbon atom of the bicyclic of the formula (I), and
G1 für N oder C-B1 steht, G 1 is N or CB 1 ,
B1 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyl steht, B 1 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
B2 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyl steht, B 2 is a radical from the series consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
T für Sauerstoff oder ein Elektronenpaar steht, T is oxygen or a pair of electrons,
Q für Sauerstoff oder Schwefel steht, Q stands for oxygen or sulfur,
R1 für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkoxy und Cyano steht, R 1 is a radical selected from the group consisting of hydrogen, alkyl, alkoxy and cyano,
R2 a) für einen der folgenden B-Reste R 2 a) for one of the following B radicals
(B-5) (B-6) (B-7) (B-8) (B-5) (B-6) (B-7) (B-8)
(B-9) (B-10) (B-l l) (B-12) -269 - (B-9) (B-10) (B1) (B-12) -269 -
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, Alkyl, Halogenalkyl, gegebenenfalls substituiertes und gegebenenfalls durch ein oder mehrere Heteroatome unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, halogeniertes Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Halogenalkylthioalkyl, in which the dashed line represents the bond to the carbon atom of the bicyclic compound of the formula (I) in which hydrogen or a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, optionally substituted and optionally saturated or unsaturated cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, haloalkylthioalkyl interrupted by one or more heteroatoms,
Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl Bis(alkoxy)alkyl, Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl, Alkoxy(alkylsulfinyl)alkyl, Alkoxy(alkylsulfonyl)alkyl,Haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, bis (alkoxy) alkyl, bis (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl, alkoxy (alkylsulfinyl) alkyl, alkoxy (alkylsulfonyl) alkyl,
Bis(alkylsulfanyl)alkyl, Bis(halogenalkylsulfanyl)alkyl, Bis(hydroxyalkylsulfanyl)alkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, alpha-Hydroxyimino-alkoxycarbonylalkyl, alpha- Alkoxyimino-alkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Alkyl, Halogenalkyl, Alkoxy und Alkoxyalkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Alkyl und Halogenalkyl), die Heteroarylreste Pyridyl, Pyridy-N-oxid, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthio, Alkylthioalkyl und Cycloalkyl) und die Heteroarylalkylreste Triazolylalkyl, Pyridylalkyl, Pyrimidylalkyl und Oxadiazolylalkyl (welche selbst wiederum substituiert sein können durch Halogen und Alkyl) steht, oder aa) für einen der folgenden B-Reste Bis (alkylsulfanyl) alkyl, bis (haloalkylsulfanyl) alkyl, bis (hydroxyalkylsulfanyl) alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyimino-alkoxycarbonylalkyl, alpha-alkoxyimino-alkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio , Alkylsulfmyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid , Oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which themselves may be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which in turn may itself be substituted by halogen, cyano, nitro, Alkyl and haloalkyl), di e heteroaryl radicals pyridyl, pyridyl-N-oxide, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may be substituted by halogen, nitro, alkyl , Haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which themselves may be substituted by halogen and alkyl), or aa) is one of the following B radicals
(B-3) (B-4) (B-3) (B-4)
(B-25) (B-26) (B-27) (B-25) (B-26) (B-27)
(B-31) (B-32)  (B-31) (B-32)
(B-35) (B-36) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, gegebenenfalls substituiertes und gegebenenfalls durch ein oder mehrere Heteroatome unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Cycloalkylalkyl, Halogenalkoxy, Alkoxyalkyl, halogeniertes Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Halogenalkylthioalkyl, Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl Bis(alkoxy)alkyl, Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl, (B-35) (B-36) in which the dashed line represents the bond to the carbon atom of the bicyclic compound of the formula (I) in which a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, optionally substituted and optionally interrupted by one or more heteroatoms saturated or unsaturated cycloalkyl, cycloalkylalkyl, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Halogenalkylthioalkyl, Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl bis (alkoxy) alkyl, bis (haloalkoxy) alkyl, alkoxy (alkylsulfanyl ) alkyl,
Alkoxy(alkylsulfinyl)alkyl, Alkoxy(alkylsulfonyl)alkyl, Bis(alkylsulfanyl)alkyl,Alkoxy (alkylsulfinyl) alkyl, alkoxy (alkylsulfonyl) alkyl, bis (alkylsulfanyl) alkyl,
Bis(halogenalkylsulfanyl)alkyl, Bis(hydroxyalkylsulfanyl)alkyl, Alkoxycarbonyl,Bis (haloalkylsulfanyl) alkyl, bis (hydroxyalkylsulfanyl) alkyl, alkoxycarbonyl,
Alkoxycarbonylalkyl, alpha-Hydroxyimino-alkoxycarbonylalkyl, alpha- Alkoxyimino- alkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Alkyl, Halogenalkyl, Alkoxy und Alkoxyalkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Alkyl und Halogenalkyl), die Heteroarylreste Imidazolyl, Pyrazolyl, Oxazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl,Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthio, Alkylthioalkyl und Cycloalkyl) und die Heteroarylalkylreste Triazolylalkyl, Pyridylalkyl, Pyrimidylalkyl und Oxadiazolylalkyl (welche selbst wiederum substituiert sein können durch Halogen und Alkyl) steht, oder wenn R für einen der unter a) oder aa) aufgeführten Reste steht, auch für einen C-Rest aus der Reihe Alkoxycarbonylalkyl, alpha-hydroxyimino-alkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio, alkylsulfmyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl , Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxide, Oxathiolanyloxide, Oxathiepanyloxide, Oxathiocanyloxide, Oxathianyldioxide, Oxathiolanyldioxide, Oxathiepanyldioxide, Oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which themselves may be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which in turn may be substituted by halo, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals imidazolyl, pyrazolyl, oxazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may be substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy , Alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which in turn may themselves be substituted by halogen and alkyl), or when R is one of the radicals listed under a) or aa), also for a C-residue from the series
steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, wherein the dashed line indicates the bond to the B radicals,
oder or
R2 c) für einen Rest der Formel R 2 c) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder d) für einen Rest der Formel wherein the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or d) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder  wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R e) für einen F-Rest aus der Reihe (F-2) bis (F-11) R e) for an F radical from the series (F-2) to (F-11)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder f) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, stands, wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or f) a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
X für Sauerstoff oder Schwefel steht, X is oxygen or sulfur,
X2 für Sauerstoff, Schwefel oder NOH steht, X 2 is oxygen, sulfur or NOH,
L für Sauerstoff oder Schwefel steht, V-Z für R24CH-CHR25 oder R24C=CR25 steht, n für 1 oder 2 steht, m für 1 , 2, 3 oder 4 steht, L is oxygen or sulfur, VZ is R 24 CH-CHR 25 or R 24 is C = CR 25 , n is 1 or 2, m is 1, 2, 3 or 4,
R3 für Wasserstoff oder Alkyl steht, R 3 is hydrogen or alkyl,
R4 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder R 4 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl, or
R3 und R4 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, R 3 and R 4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
R6 für Wasserstoff oder Alkyl steht, R7 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder R 6 is hydrogen or alkyl, R 7 is a radical selected from hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, Arylalkyl and hetarylalkyl, or
R6 und R7 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, R8 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkoxy, Halogenalkoxy, Alkenyl, Alkoxyalkyl, jeweils gegebenenfalls durch Halogen substituiertes Alkylcarbonyl und Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonyl und gegebenenfalls durch Halogen, Alkyl, Alkoxy, Halogenalkyl und Cyano substituiertes Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch Alkyl oder Arylalkyl substituiertes Ammonium-Ion steht, R 6 and R 7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, R 8 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl and optionally by halogen, alkyl, alkoxy, haloalkyl and cyano is substituted cycloalkylcarbonyl, or represents a cation or an optionally substituted by alkyl or arylalkyl ammonium ion,
R9 für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 9 is a radical from the series in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R10 für Wasserstoff oder Alkyl steht, R 10 is hydrogen or alkyl,
R8 und R10 in den Resten (C-2) und (F-2) auch gemeinsam mit den N- Atomen an die sie gebunden sind, für einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring stehen können, der mindestens ein weiteres Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R 8 and R 10 in the radicals (C-2) and (F-2) may also together with the N atoms to which they are bonded represent a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the at least one further heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
9 10 9 10
R und R in den Resten (C-2) und (F-2) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R and R in the radicals (C-2) and (F-2) may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
RU für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht, R U is an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio stands,
12 12
R für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht, 11 12 R represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio . 11 12
R und R in den Resten (C-3) und (F-3) auch gemeinsam mit dem Phosphoratom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 5- bis 7-gliedrigen Ring bilden können, der ein oder zwei Heteroatome aus der Reihe Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Schwefel enthalten kann, für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht, für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht, für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,  R and R in radicals (C-3) and (F-3) may also together with the phosphorus atom to which they are attached form a saturated or unsaturated and optionally substituted 5- to 7-membered ring, one or two Heteroatoms from the series oxygen (oxygen atoms may not be immediately adjacent) and may contain sulfur, represents an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, represents an optionally substituted radical from the series alkyl, Alkenyl, alkynyl, phenyl and phenylalkyl, a radical from the series each optionally substituted alkyl, alkenyl and alkynyl, each optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (where oxygen atoms not may be immediately adjacent) and contain nitrogen, each optionally subs substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R8 und R15 in den Resten (C-6) und (F-6) auch zusammen mit der N-S(0)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R 8 and R 15 in the radicals (C-6) and (F-6) also together with the NS (0) n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R16 für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 16 is a radical from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings are at least one heteroatom selected from the group consisting of sulfur, oxygen (oxygen atoms not being directly adjacent may each contain) and nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R8 und R16 in den Resten (C-7) und (F-7) auch zusammen mit dem N-Atom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, R 8 and R 16 in the radicals (C-7) and (F-7) together with the N-atom to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, which may contain one or more further heteroatoms from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R17 für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, R 17 is a radical from the series in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in in which each of the rings is at least one heteroatom selected from the group consisting of sulfur, oxygen (where oxygen atoms are not immediately adjacent) and nitrogen, optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R8 und R17 in den Resten (C-8) und (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, und im Fall, dass R2 für einen der unter f) aufgeführten Reste steht, R 8 and R 17 in the radicals (C-8) and (F-8) together with the NC (X) group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring can contain one or more further heteroatoms from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group, and in the case that R 2 is one of the radicals listed under f) .
R22 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkenyl, Halogenalkenyl, Alkinyl, Halogenalkinyl, Alkoxy, Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Alkoxyalkyl, gegebenenfalls durch Halogen substituiertes Bis(alkoxy)alkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfanylalkyl, gegebenenfalls durch Halogen substituiertes Alkylcarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfinylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfonylalkyl, Dialkylaminosulfanylalkyl, Dialkylaminosulfinylalkyl, Dialkylaminosulfonylalkyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkinyloxy, Dialkylaminocarbonylalkyl, N-Alkyl-N-Cycloalkylaminocarbonylalkyl, Heterocyclyl- carbonylalkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkylalkyl, gegebenenfalls substituiertes Heterocyclyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclylalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist)Alkoxy oder Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Amino, Alkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Halogenalkyl, Alkoxy oder Halogenalkoxy substituiertes Arylalkyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetarylalkyl steht, und im Fall, dass R2 für einen der unter c), d) oder f) aufgeführten Reste steht auch für einen D-Rest aus der Reihe (D-l) bis (D-3) R 22 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis (alkoxy) alkyl, optionally halogen-substituted alkylsulfanylalkyl, optionally substituted by halogen alkylsulfinylalkyl, optionally substituted by halogen alkylsulfinylalkyl, optionally substituted by halogen alkylsulfonylalkyl, dialkylaminosulfanylalkyl, dialkylaminosulfinylalkyl, dialkylaminosulfonylalkyl, optionally halogen substituted alkoxycarbonylalkyl, optionally halogen substituted alkynyloxy, dialkylaminocarbonylalkyl, N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonylalkyl, Alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, if appropriate by halogen, cyano, nitro, alkyl, cycloalkyl, Haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkyl, optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which optionally itself substituted by alkyl or halogen) substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio , Alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl substituted heterocyclylalkyl, optionally all aryl substituted by halogen, cyano, nitro, hydroxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted) alkoxy or haloalkoxy, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, Amino, alkyl, cycloalkyl (which is optionally substituted), haloalkyl, alkoxy or haloalkoxy-substituted arylalkyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy , Alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl substituted hetarylalkyl, and in the case where R 2 is one of the radicals listed under c), d) or f) also stands for a D radical from the series (D1) to (D-3)
(D-1 ) (D-2) (D-3) wonn  (D-1) (D-2) (D-3) wonn
R für NR R oder für einen jeweils gegebenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkyl-S-alkyl, Alkyl-S(0)-alkyl, Alkyl-S(0)2-alkyl, R18-CO-alkyl, NR18R19-CO-alkyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkenylalkyl, Heterocyclyl, Heterocyclylalkyl, Phenyl, Phenylalkyl, Hetaryl und Hetarylalkyl steht, für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy und Halogenalkoxy steht, einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Alkyl, Cycloalkyl, Halogenalkyl,R is NR R or an optionally substituted radical from the group alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S (0) -alkyl, alkyl-S (0) 2- alkyl, R 18 - CO-alkyl, NR 18 R 19 -CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl, is a radical from the series consisting of hydrogen, halogen, cyano, nitro, alkyl, Haloalkyl, cycloalkyl, alkoxy and haloalkoxy, a radical selected from the group consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl,
Alkoxy, Halogenalkoxy und NR20R21 steht, für einen Rest aus der Reihe S, SO und SO2 steht, Alkoxy, haloalkoxy and NR 20 R 21, is a radical from the series S, SO and SO 2,
R18 für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkylcarbonyl, Alkoxycarbonyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl und Cycloalkenylalkyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Arylalkyl, Heteroaryl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, für einen Rest aus der Reihe Wasserstoff, für ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch Ci-C i-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl und Alkylsulfonylalkyl steht, und im Fall, dass R2 für einen der unter f) aufgeführten Reste steht auch für einen E-Rest aus der Reihe (E-l) bis (E-l 1) R 18 is a radical selected from the group consisting of hydrogen, hydroxy, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the rings at least one Heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and may contain nitrogen, each optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group, a radical selected from the group hydrogen, for an alkali metal or in the case of an optionally monosubstituted to cis-C 1-4 -alkyl-substituted ammonium ion or an optionally halogen or cyano-substituted radical from the series consisting of alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl, and in the case where R 2 for one of the radicals listed under f) is also an E radical from the series (El) to (El 1)
und (E-l 8) bis (E-51) and (El 8) to (E-51)
E-22 E-23 E-24 E-25 E-22 E-23 E-24 E-25
E-27 E-28 E-29 E-30 E-27 E-28 E-29 E-30
E-32 E-33 E-34 E-32 E-33 E-34
E-35 E-36 E-35 E-36
E-37 E-38 E-39 E-40  E-37 E-38 E-39 E-40
E-44 E-45 E-46 E-47  E-44 E-45 E-46 E-47
E-48 E-49 E-50 E-51 steht,  E-48 E-49 E-50 E-51 stands,
R20 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy und jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylcarbonyloxy, Alkenylcarbonyloxy,R 20 is a radical selected from among hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy,
Alkinylcarbonyloxy, Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Alkylsulfonyloxy, Alkylamino, Alkenylamino, Alkinylamino, Cycloalkylamino, Alkylthio, Halogenalkylthio, Alkenylthio, Alkinylthio, Cycloalkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylcarbonyl, Alkoxyiminoalkyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Aminothiocarbonyl, Alkylaminosulfonyl, Alkylsulfonylamino,Alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulphonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino,
Alkylcarbonylamino, Alkenylcarbonylamino, Alkinylcarbonylamino, Cycloalkylcarbonylamino, Alkoxycarbonylamino, Alkylthiocarbonylamino, Bicycloalkyl, Aryl, Aryloxy, Heteroaryl und Heteroaryloxy steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl und Halogenalkyl, R für einen Rest aus der Reihe Wasserstoff, Alkyl, Cycloalkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Cyanoalkyl, Alkylcarbonyl, Alkenylcarbonyl, Halogenalkylcarbonyl, Halogenalkenylcarbonyl, Alkoxyalkyl, Alkoxycarbonyl, Alkylsulfonyl und Halogenalkylsulfonyl steht, für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylthioalkyl, Alkenylthioalkyl, Cyanoalkyl und Alkoxyalkyl steht oder, wenn für R2 für einen der unter f) aufgeführten Reste steht, und R23 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, und für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht und für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht, für Wasserstoff oder Alkyl steht und für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy-alkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl und Cyanoalkyl steht. Alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, wherein the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, alkyl and haloalkyl, R is a radical the series hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, Haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl, is a radical from the series hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl and alkoxyalkyl or, if R 2 stands for one of the radicals listed under f), and R 23 together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, and for hydrogen or each represents optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and is hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, is hydrogen or alkyl and a radical from the group of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalk ylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl.
Verbindungen der Formel (I) gemäß Anspruch 1 , in welchen für Compounds of formula (I) according to claim 1, in which
(A-a) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, G1 für C-B1 steht, - 2oi - (Aa), in which the dashed line represents the bond to the carbon atom of the bicyclic compound of the formula (I), G 1 is CB 1 , - 2oi -
B1 für Wasserstoff steht, B2 für Wasserstoff steht, T für ein Elektronenpaar steht, Q für Schwefel steht, R1 für Wasserstoff steht, B 1 is hydrogen, B 2 is hydrogen, T is an electron pair, Q is sulfur, R 1 is hydrogen,
R2 für einen B-Rest aus der Reihe R 2 for a B residue from the series
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R2 b) für (D-2) in which the dashed line denotes the bond to the carbon atom of the bicycle of the formula (I), or R 2 b) for (D-2)
(D-2) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder (D-2), wherein the dotted line represents the bond to the carbon atom of the bicycle of the formula (I), or
R2 c) für einen Rest der Formel R 2 c) is a radical of the formula
X X
,R  , R
1  1
R steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder f) für einen Rest der Formel R is where the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I), or f) for a radical of the formula
- / R22 - / R 22
I 9  I 9
R steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder g) für einen Rest der Formel steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, R is where the dotted line represents the bond to the carbon atom of the bicycle of formula (I), or g) is a radical of the formula in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
G2 für Wasserstoff oder einen Rest aus der Reihe Ci-C i-Alkyl, Halogen-Ci-C i-alkyl und Pyrimidyl steht, G 2 is hydrogen or a radical from the series Ci-C i-alkyl, halo-Ci-C i-alkyl and pyrimidyl,
G3 für einen Rest aus der Reihe Wasserstoff, Halogen und Ci-C/i-Alkyl steht, G 3 is a radical selected from the group consisting of hydrogen, halogen and C 1 -C 1 -alkyl,
X für Sauerstoff steht, X stands for oxygen,
XI für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Methyl und Ethyl steht, X I is a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl and ethyl,
R für gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor substituiertes Ci-C/i-Alkyl steht, R represents optionally mono-, di-, tri-, tetra- or quintuple C 1 -C -alkyl which is substituted by fluorine, chlorine,
W für einen Rest aus der Reihe S, SO und SO2 steht, W is a radical from the series S, SO and SO2,
Y3 für einen Rest aus der Reihe Wasserstoff, Methyl und Ethyl steht, Y 3 is a radical selected from the group consisting of hydrogen, methyl and ethyl,
R22 für einen Rest aus der Reihe Methyl, Ethyl, Isopropyl, n-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert- Butyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2,2-Difluor-n-propyl, Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Arylmethyl, Arylethyl und Pyridylmethyl, für (D-l) oder (D-2) R 22 is a radical selected from the group consisting of methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2, 2-difluoro-n-propyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, arylmethyl, arylethyl and pyridylmethyl, for (Dl) or (D-2)
(D-1 ) (D-2) steht,  (D-1) (D-2),
R23 für Wasserstoff oder Ci-C6-Alkyl steht, oder R 23 is hydrogen or C 1 -C 6 -alkyl, or
R22 und R23 auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für Morpholinyl stehen. 3. Verbindungen der Formel (I) gemäß Anspruch 1, woein A für den A-Re R 22 and R 23 together with the nitrogen atom to which they are attached represent morpholinyl. 3. Compounds of formula (I) according to claim 1, where A is the A-Re
(A-a) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,  (A-a), wherein the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I),
G1 für N oder C-B1 steht, G 1 is N or CB 1 ,
B1 für einen Rest aus der Reihe Wasserstoff und Fluor steht, B 1 is a radical from the series hydrogen and fluorine,
B2 für Wasserstoff steht, B 2 is hydrogen,
T für ein Elektronenpaar steht, T stands for a pair of electrons,
Q für Schwefel steht, Q stands for sulfur,
R1 für Wasserstoff steht, R 1 is hydrogen,
R2 a) für einen B-Rest aus der Reihe R 2 a) for a B residue from the series
(B-38) (B-39) (B-40) (B-41 ) (B-38) (B-39) (B-40) (B-41)
(B-42) (B-43) (B-44) (B-45) steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin (B-42) (B-43) (B-44) (B- 45), wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of the formula (I) wherein
G2 für Wasserstoff oder einen Rest aus der Reihe Ci-C i-Alkyl, Halogen-Ci-C i-alkyl, Ci-C i-Alkoxy, Halogen-Ci-C i-alkoxy, Ci-C4-Alkylthio-Ci-C4-alkyl, halogeniertes Ci-C4-Alkylthio-Ci-C4-alkyl, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylthio, Ci-C4-G 2 is hydrogen or a radical from the series Ci-C i-alkyl, halo-Ci-C i-alkyl, Ci-C i-alkoxy, halo-Ci-C i-alkoxy, Ci-C4-alkylthio-Ci C4-alkyl, halogenated Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C 4 -
Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl steht, oder Haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, or
R2 aa) für den B-Rest R 2 aa) for the B radical
(B-4)  (B-4)
steht, worin  stands in which
G2 für Ci-C4-Alkylthio-Ci-C4-alkyl oder halogeniertes Ci-C4-Alkylthio-Ci-C4-alkyl steht, oder R2 c) für einen Rest der Formel G 2 is C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or halogenated C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, or R 2 c) is a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder d) für einen Rest der Formel wherein the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or d) a radical of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder f) für einen Rest der Formel in which the dashed line represents the bond to the carbon atom of the bicycle of the formula (I), or f) a radical of the formula
22 22
- R  - R
ΊΜ' ΊΜ '
I 9  I 9
R steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,  R is where the dotted line represents the bond to the carbon atom of the bicyclic compound of the formula (I),
X für Sauerstoff steht, R22 für den D-Rest X is oxygen, R 22 is the D radical
(D-2) steht, worin  (D-2) in which
R für jeweils gegebenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituiertes Ci-C i-Alkyl steht, R is in each case monosubstituted, disubstituted, trisubstituted, trisubstituted or trisubstituted by fluorine, chlorine or C 1 -C -alkyl which is monosubstituted or cyano-substituted,
X1 für Wasserstoff, Methyl oder Fluor steht, X 1 is hydrogen, methyl or fluorine,
W für einen Rest aus der Reihe S, SO und SO2 steht, W is a radical from the series S, SO and SO2,
Y3 für Wasserstoff oder Methyl steht, R im Fall, dass R für f) steht, auch für einen Rest aus der Reihe Methyl, Ethyl, Isopropyl, n-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2,2-Difluor-n- propyl, Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Phenylmethyl, Phenylethyl und Pyridyl steht und R23 für einen Rest aus der Reihe Wasserstoff und Ci-Cö-Alkyl steht. Y 3 is hydrogen or methyl, R in the case that R is f), also a radical from the series methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2,2,2- Trifluoroethyl, 2,2-difluoroethyl, 2,2-difluoro-n-propyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, phenylmethyl, phenylethyl and pyridyl and R 23 is a radical from the series hydrogen and Ci-Cö-alkyl.
4. Mittel, gekennzeichnet durch einen Gehalt von mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3 und üblichen Streckmitteln und/oder oberflächenaktiven Substanzen. 4. agent, characterized by a content of at least one compound of formula (I) according to any one of claims 1 to 3 and conventional extenders and / or surface-active substances.
5. Verwendung von Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von Mitteln gemäß Anspruch 4 zur Bekämpfung von Schädlingen. 5. Use of compounds of the formula (I) according to one of claims 1 to 3 or of agents according to claim 4 for combating pests.
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JP6857614B2 (en) 2015-04-09 2021-04-14 エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ Bicyclic pyrazole pesticide
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CA1019748A (en) * 1972-06-02 1977-10-25 Venkatachala L. Narayanan Isothiocyanobenzoxazoles
US3985755A (en) * 1972-06-02 1976-10-12 E. R. Squibb & Sons, Inc. Pyridine containing isothiocyanobenzoxazoles
US3985885A (en) * 1975-09-19 1976-10-12 E. R. Squibb & Sons, Inc. Isothiocyanobenzothiazoles
PE20010830A1 (en) * 2000-01-28 2001-09-06 Syngenta Ltd DERIVATIVES OF AZOL INSECTICIDES OR FUNGICIDES AND COMPOSITIONS THAT INCLUDE THEM
TW201018678A (en) * 2006-01-27 2010-05-16 Astrazeneca Ab Novel heteroaryl substituted benzothiazoles
JP5369854B2 (en) * 2008-04-21 2013-12-18 住友化学株式会社 Harmful arthropod control composition and condensed heterocyclic compound
WO2013106254A1 (en) * 2012-01-11 2013-07-18 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
WO2014028931A2 (en) * 2012-08-17 2014-02-20 Brandeis University Compounds and methods for treating mammalian gastrointestinal microbial infections
TWI652014B (en) * 2013-09-13 2019-03-01 美商艾佛艾姆希公司 Heterocyclic substituted bicycloazole insecticide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
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