EP3227289A1 - Bicyclic compounds as pest control agents - Google Patents

Bicyclic compounds as pest control agents

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Publication number
EP3227289A1
EP3227289A1 EP15801850.7A EP15801850A EP3227289A1 EP 3227289 A1 EP3227289 A1 EP 3227289A1 EP 15801850 A EP15801850 A EP 15801850A EP 3227289 A1 EP3227289 A1 EP 3227289A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
spp
radical
optionally substituted
alkoxy
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Withdrawn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
EP15801850.7A
Other languages
German (de)
French (fr)
Inventor
Peter Jeschke
Alexander ARLT
Silvia Cerezo-Galvez
Arnd Voerste
Martin FÜSSLEIN
Reiner Fischer
Thomas Bretschneider
Kerstin Ilg
Olga Malsam
Peter Lösel
Ulrich Görgens
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP3227289A1 publication Critical patent/EP3227289A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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.
  • bicyclic compounds have become known which possess insecticidal properties (WO 2015/038503 Al).
  • WO 2010/078408 Al the presentation and pharmaceutical use of Raf kinase inhibitors and in WO 2013/259064 AI the synthesis of anti-HTV agents and their use for the treatment of HIV infections is described which u. a. contain an N-substituted 2H-pyrazolo [3,4-] pyridin-1-yl fragment.
  • WO 2010/056999 describes the preparation of parasiticides containing an N-substituted 2H-pyrazolo [3,4-] pyridin-1-yl fragment.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides from various aspects.
  • 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 2 f is a radical from the series haloalkyl, carboxyl and amino, wherein
  • G 2 is hydrogen or a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, alkoxycarbonylalkyl, 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 (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl,
  • X 1 is a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy and haloalkoxy,
  • X 2 is oxygen, sulfur, NR 5 or NOH
  • L is oxygen or sulfur
  • R is NR 18 R 19 or an 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 or 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, if appropriate 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 10 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, 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 .
  • 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, 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
  • 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 other 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 series hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and
  • 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 may contain one or more further heteroatoms selected from the group 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 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 group consisting of sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen, each optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group,
  • 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 alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl , Alkylsulfinylalkyl, 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 series alkyl, optionally substituted by halogen, carbamoyl, thiocarbamoyl or cyano substituted cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, Alkylthioalkyloxy, Alkylsulfinylalkyloxy, Alkylsulfonylalkyloxy, haloalkylthioalkyl, Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl, alky
  • 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 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 series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, is hydrogen or alkyl and
  • R 26 is a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl.
  • the compounds of the formula (I) have good activity as pesticides, for example against arthropods and in particular insects, and, moreover, are generally very well tolerated by crops, in particular, and / or via favorable toxicological and / or favorable environmental factors Features.
  • A is a radical from the series (A-a), (A-b) and (A-f)
  • T oxygen or a pair of electrons
  • R 2 c is a radical of the formula
  • R 2 d is a radical of the formula
  • R is where the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I), or
  • R 2 e is a radical from the series (F-1), (F-8), (F-10) and (F-11)
  • R 2 f is a radical from the series Ci-C6-haloalkyl, carboxyl and amino, wherein
  • G 2 is hydrogen or a radical from the group halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno-C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkyl, C 1 -C 6 -cycloalkyl -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -
  • X represents oxygen or sulfur
  • X1 represents a radical from the series consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl , CI-COE haloalkyl, C3-C6-cycloalkyl, CI-C ⁇ - alkoxy and Ci-C6-haloalkoxy
  • X 2 is oxygen, sulfur, NR 5 or NOH
  • R 3 is hydrogen or C 1 -C 6 -alkyl
  • 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 group of hydrogen, Ci-C4 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, 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 6 -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, 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 Ci-C6-haloalkylsulfonyl substituted C1 -C6- alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl, each optionally substituted by halogen, Ci-COE-alkyl, Ci Coe-haloalkyl, Ci -C6-alkoxy or Ci-C6-haloalkoxy-substituted C3-C6
  • 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
  • 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-Cö-alkyl, heteroaryl-Ci-C6-alkyl or NR'R ", wherein R 'and R" independently of one another from a number of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl, or
  • 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
  • Form alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkoxy-substituted 5 to 7-membered ring which has one or two heteroatoms selected from the group consisting of sulfur, oxygen (oxygen atoms may not be directly adjacent) and nitrogen and / or at least one and preferably a 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 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 selected from the group consisting of hydrogen, in each case optionally 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 -al
  • R 17 is a radical from the series in each case optionally substituted by halogen, Ci-C6-alkoxy, CI-C ⁇ -haloalkoxy, Ci-Cö-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, CI-C ⁇ -haloalkylsulfinyl, Ci C6-alkylsulfonyl or Ci-C6-haloalkylsulfonyl-substituted CI-C ⁇ - alkyl, Ci-C6-alkoxy, C2-C6-alkenyl and C2-C6 alkynyl, each optionally substituted by halogen, Ci-COE-alkyl, Ci-C6 Haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C
  • R 8 and R 17 in the radical (C-8) and in the radical (F-8) can also be used together with the NC (X) group to which they are attached, a saturated or unsaturated and optionally halogen, CI-C Form alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkoxy-substituted 5 to 7-membered ring which contains 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 may be taken together with the NC (X) group to which they are attached, for a residue from the series
  • R 18 is a radical from the group of hydrogen, hydroxy, optionally mono- or polysubstituted by halogen or monosubstituted or disubstituted by cyano substituted C ⁇ - 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, heterocycly
  • R 19 represents hydrogen, an alkali metal or alkaline earth metal ion or an optionally monosubstituted to monosubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or an optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted radical from the series 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 4 -alkyl, C 1 -C 4 -alkyl-S (0) -C 1 -C 4 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 4 -alkyl,
  • Y 3 is a radical from the series consisting of hydrogen, halogen, cyano, 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 and NR 20 R 21 , is a radical from the series O, S, SO and SO2, a radical from the series Ci-C6-alkyl, optionally substituted by halogen, carbamoyl, thiocarbamoyl or cyano substituted C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci -C 6 -alkoxy, C 1 -C -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkyls
  • E-48 E-49 E-50 E-51 stands for a radical from the series hydrogen, halogen, cyano, nitro, amino, hydroxy, Ci-C6-alkyl, Ci-Ce-haloalkyl, cyano-Ci-C 6 alkyl, C 2 -C 6 alkenyl, C C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -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
  • Halogenalkenylcarbonyl, Ci-C 6 alkoxy-C 6 alkyl, Ci-C 6 alkoxycarbonyl, Ci-COE-alkylsulfonyl, and Ci-C is 6 -Halogengenalkylsulfonyl, a radical from the group of hydrogen, Ci-alkyl COE , 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,
  • A is a radical from the series (A-a), (A-b) and (A-f)
  • 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 -haloalkyl,
  • B 2 is a radical from the series consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 1 -haloalkyl,
  • T oxygen or a pair of electrons
  • R is where the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I), or
  • R f is a radical from the series Ci-Cö-haloalkyl, carboxyl and amino, wherein
  • G is hydrogen or a radical from the series halogen, nitro, amino, cyano, C 1 -C -alkylamino, halogeno-C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl 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, 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
  • X 1 is 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, C 1 -C 4 -alkoxy and C4 haloalkoxy stands,
  • X 2 is oxygen, sulfur, NR 5 or NOH, n is 2,
  • C O
  • C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 6 -cycloalkyl, optionally substituted once or twice by oxygen (leads to C O)
  • C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 8 -cycloalkenyl, optionally substituted once or twice by oxygen (leads to C O)
  • R 4 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 6 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,
  • R 5 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 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-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 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkyl, 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-C 1 -C 4 -alkyl, arylcyclo C 4 alkyl or hetaryl C 1 -C 4 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, 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 is a radical from the group in each case optionally substituted by halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkoxy 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 by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkyl Alkoxy
  • 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-C6-alkoxy, Ci-C6-haloalkoxy-substituted 5- to 7-membered ring forming one or two heteroatoms selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably can contain exactly one carbonyl group, in particular R 8 and R 9 together with the NS (0) n group to which they are attached may be a member of the series
  • R 15 is a radical selected from the group each optionally substituted by methyl C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each optionally substituted by methyl, halogen, cyano or carbamoyl-substituted C 3 -C 6 -cycloalkyl, C3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl and C 3 -C 6 -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 contain nitrogen and / or at least one carbonyl group,
  • R 17 is a radical from the series in each case optionally substituted by halogen, C 1 -C -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl-substituted C 1 -C 4 - alkyl, C2-C4 alkenyl and C2-C4 alkynyl, each optionally substituted by halogen, C1-C4 alkyl, Ci- C4-haloalkyl , C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy-substituted C 3 -C 6 -cycl
  • Ci-Ci-alkyl is hydrogen or Ci-Ci-alkyl and R Zb is hydrogen, C 1 -C 4 -alkyl, 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 , Ci-C4-alkoxy-Ci-C 2 alkyl, Ci-C4-alkylthio-Ci-C 2 alkyl, Ci-C4-alkylsulfinyl-Ci-C 2 - alkyl, Ci-C4 alkylsulfonyl Ci-C 2 -alkyl or cyano-Ci-C 4 -alkyl.
  • Preferred Range (3) Very particular preference is given to compounds of the formula (I) in which, for a radical from the series (A-a), (A-b) and (A-f)
  • 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 oxygen or a pair of electrons
  • R 2 d is 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 f is a radical from the series Ci-C6-haloalkyl, carboxyl and amino, wherein
  • G 2 is hydrogen or a radical selected from halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl-Ci- -C 4 alkyl, halo-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-C4-alkyl, bis (Ci-C4-alkoxy) -C-C4-alkyl, bis (halo-Ci-C4-alkoxy) -C-C 4 alkyl, Ci-C4
  • G 2 is a C-radical (C-1) or (C-9)
  • X 1 is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
  • X 2 is oxygen, sulfur, NR 5 or NOH, n is 2,
  • R is NR 18 R 19 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) - C 1 -C 2 -alkyl, C 1 -C 2 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, for R 18 -CO-C 1 -C 2 -alkyl, for NR 18 R 19 -CO-Ci- C 2 -alkyl, for optionally mono- or disubstit
  • R 3 is C 1 -C 4 -alkyl
  • R 4 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 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkoxycarbonyl, Ci- C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, 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 , C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, 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 -
  • 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, 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 optional
  • R is a radical from the group in each case optionally substituted by halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkoxy 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 by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkyl Alkoxy
  • 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-C6-alkoxy, Ci-C6-haloalkoxy-substituted 5- to 7-membered ring forming one or two heteroatoms selected from the group 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 17 is a radical from the series in each case optionally substituted by halogen, C 1 -C -alkoxy, C 1 -C 4 -halogenoalkoxy, 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 -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 -haloalkyl, C 4 -alkoxy, C 1 -C 4 -haloalkoxy
  • Y is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
  • R 18 is a radical selected from the group consisting of hydrogen and hydroxy, in each case optionally mono-, di-, tri-, tetra- or trisubstituted by fluorine, chlorine or mono- or disubstituted cyano-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S-Ci-C 2 alkyl, Ci-C 4 alkyl-S (0) -C-C 2 alkyl, Ci- C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkyl, He
  • R 19 is hydrogen, an alkali or alkaline earth metal ion, for an optionally mono- to quadruple by Ci-C 4 alkyl substituted ammonium ion or for each optionally single, double, triple, quadruple or five times by fluorine, chlorine or mono- or disubstituted by cyano substituted 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) -C-C 2 alkyl, and Ci-C 4 alkyl-S (0) 2 -C-C 2 - alkyl,
  • R 22 when R 2 is the radical c) is a radical from the series Ci-C6-alkyl, optionally substituted by cyano C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C4-haloalkoxy , Ci-Ce-alkoxy-Ci-Ce-alkyloxy, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, C1-C4 alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfinyl, Ci-C 4 haloalkylsulfonyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C 4 -Alkylsulfmyl-Ci-C4-alkyl, Ci-C 4 alkylsulfonyl-Ci-C4
  • R 23 when R 2 is the radical c) is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C -alkynyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl- alkyl, C 2 -C alkenylthio-Ci-C alkyl, cyano, Ci-C4-alkyl, Ci-C 4 -alkoxy-Ci-C 4 alkyl, when R 2 is the radical d) is a radical from the series Ci-C i-alkyl, optionally substituted by cyano C3-C6-cycloalkyl, Ci-C i -haloalkyl, Ci-C 4 -alkylthio-Ci-C 4 alkyl, Ci- C4 -Alkylsulfmyl-Ci-C4-alkyl, Ci-C 4
  • a preferred group of compounds of the formula (I) are those in which
  • A is a radical from the series (A-a), (A-b) and (A-f)
  • 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 is an electron pair
  • R is a radical selected from C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C -alkylsulfonyl and di (C 1 -C 4 -alkyl) -aminosulfonyl and R 23 is hydrogen or C 1 -C 6 -alkyl.
  • the combination of which forms the preferred range (1) unless otherwise specified
  • 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 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 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,
  • 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,
  • 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, for example, arylalkyl selected from the group consisting of phenyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents phenyl,
  • Hetaryl (synonymous with heteroaryl, also as part of a larger unit, such as hetarylalkyl) selected from 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 the series azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, Thiethanyl, thiolanyl, thianyl, tetrahydrofuryl, piperazinyl, morpholinyl.
  • Cation for an alkali metal ion from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or a
  • Heterocyclyl for oxetanyl, thiethanyl, tetrahydrofuryl and morpholinyl Aryl for phenyl, hetaryl (equivalent to heteroaryl, also as part of a larger moiety, 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, in each case also in combination with heteroatoms, for example in alkoxy, may be straight-chain or branched as far as possible.
  • 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
  • (Aa) is oxygen, the remainder is a pyridine-N-oxide derivative of the formula in front.
  • the representation of the formal charges (+ on the nitrogen and - on the oxygen) was omitted here.
  • 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)). 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)).
  • a preferred embodiment of the invention relates to compounds of the formula (I) in which A represents the radical of the formula (A-a)
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A represents the radical of the formula (Ab)
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A represents the radical of the F
  • 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 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 (IN) 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-A)
  • the invention relates to compounds of the formula (I-B)
  • the invention relates to compounds of the formula (IC)
  • the invention relates to compounds of the formula (ID)
  • the invention relates to compounds of the formula (IE)
  • the invention relates to compounds of the formula (IF)
  • the invention relates to compounds of the formula (IG)
  • the invention relates to compounds of the formula (IH)
  • 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 (II)
  • the invention relates to compounds of the formula (I-M)
  • the invention relates to compounds of the formula (I-N)
  • the compounds of the formula (I) according to the invention and their acid addition salts and metal salt complexes have good activity, in particular for controlling animal pests, which include arthropods and in particular insects.
  • the compounds of formula (I) may also be optionally substituted as stereoisomers, i.e., depending on the nature of the substituents. as geometric and / or as optical isomers or mixtures of isomers are present in different compositions. 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.
  • animal pests which include arthropods and in particular insects.
  • the optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention.
  • Suitable salts of the compounds of general formula (I) may be conventional non-toxic salts, i. H. 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
  • Azomethine derivatives or so-called "Schiff bases” of amino-substituted heterocycles have various applications (for example, form metal complexes or are biologically active) and can be synthesized by conventional methods (see also V. Shama, et al, Internal J. Univ Bio Science 2013, 2, 241-57 and literature cited therein.)
  • A 5-fluoropyridin-3-yl
  • G 1 CF
  • T electron pair
  • A 5-fluoropyridin-3-yl
  • T electron pair
  • A 5-fluoropyridin-3-yl
  • T electron pair
  • A2 5-fluoropyridin-3-yl
  • T electron pair
  • B 2 H
  • Ac WO 2012/151567 Al
  • the compounds of the formula (A-3) can be obtained by the synthesis method known in step 1 of the said preparation process or according to the principle known, cf. for example, the preparation of 4-methyl-N - [(3-nitro-4-pyridinyl) methylene] -benzamine (Baumgarten, H.E., et al., J. Amer. Chem. Soc., 77, 2438-2440, 1955).
  • the compounds of the formula (I) can be obtained in accordance with step 2 of the stated preparation process by means of a reductive cyclization of the 4-imino-5-nitropyridines of the formula (A-3), for example in accordance with the Candogan indazole synthesis in the presence of triethyl phosphite ( See JIG Candogan et al., J.Chem.Soc., 1965, 4831; NE Genung et al., Org. Lett. 16, 3114-3117, 2014, and Synthesis of Azaindazoles: WO 2008/147822 A1 and WO 2010/056999). ,
  • reaction conditions of the reductive cyclization according to Candogan et al. or corresponding alternative reaction conditions are used, such as the transition metal-catalyzed reductive cyclization of imino-nitroaromatics and the thermal transition metal-catalyzed cyclization of 2-azido-imines (see NE Genung et al., Org. Lett., 2014, 16 , 3114-3117 and references cited therein).
  • R represents a radical (B1), (B-2), (B-10), (B-29) or (B-30)
  • R represents a radical (B1), (B-2), (B-10), (B-29) or (B-30)
  • R represents a radical (B1), (B-2), (B-10), (B-29) or (B-30)
  • R represents a radical (B1), (B-2), (B-10), (B-29) or (B-30)
  • copper (I) iodide and basic reaction auxiliaries such as iraft -N, N'-dimethylcyclohexane-l, 2-diamine and potassium carbonate
  • 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.
  • the compounds of the formula (Ia) can first be converted by means of methods known from the literature into compounds of the formula (Ie) which are then subsequently reacted with halogen-activated heterocycles according to Reaction Scheme III according to Method C (see T. Ishiyama et al, J. Org. Chem., 1995, 60, 7508-7510, WO 2010/151601).
  • R 2 is a radical (B-21) or (B-23)
  • R 2 is a radical (B-21) or (B-23)
  • suitable coupling catalysts preferably in the presence of suitable coupling catalysts , basic reaction auxiliaries, and in a suitable solvent or diluent.
  • 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.
  • Suitable coupling catalysts are palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) or tetrakis (triphenylphosphine) palladium.
  • Suitable basic reaction auxiliaries for carrying out the processes according to Reaction Scheme III are preferably carbonates of sodium or potassium.
  • nitriles such as acetonitrile, benzonitrile, in particular acetonitrile, or ethers such as diethyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, in particular 1, 2-dimethoxyethane used in combination with water.
  • Compounds of the formula (I) in which R 2 is a radical from the series (Cl) to (C-9) or CX-NR 22 R 23 may be prepared, for example, from compounds of the formula (I) in which R 2 is a carboxyl group, after appropriate activation (ie LG is an optionally generated in situ nucleofuge leaving group) can be prepared by known methods.
  • Suitable condensing agents for activating the carboxylic acids of the formula (Ib) are all condensing agents customarily used for such amidation reactions.
  • acid halide formers such as phosgene, phosgene derivatives such as carbonyldiimidazole (CDI), 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-l, 2-dihydroquinoline (EEDQ), tripheny
  • Suitable reaction auxiliaries are basic reaction auxiliaries for carrying out the processes according to Reaction Scheme IV.
  • Examples include the hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium, further basic compounds such as amidine bases or guanidine bases such as 7-methyl-l, 5,7-triaza-bicyclo (4.4.0 ) dec-5-ene (MTBD); Diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) octane (DABCO), 1,8-diazabicyclo (5.4.0) undecene (DBU), cyclohexyltetrabutyl-guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), ⁇ , ⁇ , ⁇ , ⁇ -tetramethyl-l, 8-naphthalenediamine, pentamethylpiperidine, tertiary amines such as triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributyl
  • reaction auxiliaries for carrying out the processes according to Reaction Scheme IV it is possible to use all suitable acid binders, for example amines, in particular tertiary amines, and also alkali metal and alkaline earth metal compounds.
  • suitable acid binders for example amines, in particular tertiary amines, and also alkali metal and alkaline earth metal compounds.
  • tertiary amines such as N-propyldiisopropylamine or N-ethyldiisopropylamine (DIEA; Hünig's base).
  • 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 -Methylformanilid, N-methylpyrrolidone, hexamethylphosphoric triamide) and dimethyl sulfoxide or water or mixture
  • Amides for example N, N-dimethylformamide, are preferably used as solvent.
  • Compounds of the formula (I) in which R 2 is a radical from the series (D-1) to (D-3) can be prepared, for example, from compounds of the formula (I) in which R 2 is halogen from the series bromine and iodine, are prepared by methods known in principle.
  • Suitable coupling catalysts are palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) or tetrakis (triphenylphosphine) palladium.
  • Suitable basic reaction auxiliaries for carrying out the processes according to Reaction Scheme III are preferably carbonates of sodium or potassium.
  • nitriles such as acetonitrile, benzonitrile, in particular acetonitrile, or ethers such as diethyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, in particular 1, 2-dimethoxyethane used in combination with water.
  • ethers such as diethyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, in particular 1, 2-dimethoxyethane used in combination with water.
  • Compounds of the formula (I) in which W is SO (sulfoxides) or SO 2 (sulfones) can be prepared by oxidation by methods known from the literature from compounds of the formula (I) in which W is S (thioethers), for example by an oxidizing agent in a suitable solution. Diluent.
  • an oxidizing agent for example, dilute nitric acid, hydrogen peroxide, Oxone ® and peroxycarboxylic acids such as WEFA-chloroperbenzoic own.
  • solvents or diluents are inert organic solvent, typically acetonitrile, halogenated solvents such as dichloromethane, chloroform or dichloroethane, as well as water and alcohols such as methanol for reaction with Oxone ® suitable.
  • 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 (TB HP), 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).
  • TB HP tert-butyl hydrogen peroxid
  • LG Leaving group, z. B. halogen
  • compounds of the formula (I-f) can be obtained by Curtius degradation, as described, for example, in Houben-Weyl, Methoden der Organischen Chemie, Volume XI / 1 (Georg Thieme Verlag Stuttgart), page 865.
  • the compounds of the formula (I-b) can react, for example, with diphenylphosphoryl azide (DPPA) in the presence of tert-butanol directly to compounds of the formula (I-f).
  • DPPA diphenylphosphoryl azide
  • the compounds of the formulas (Ig) 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 (Ih) 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.
  • the tert-butylcarbamate protecting group for example, mixtures of mineral acids such as hydrochloric, hydrobromic, nitric, sulfuric, phosphoric or organic acids such as benzoic, formic, acetic, trifluoroacetic, methanesulfonic, benzenesulfonic or toluenesulfonic in a suitable diluent such as water and / or an organic solvent such as tetrahydrofuran, dioxane, dichloromethane, chloroform, ethyl acetate, ethanol or methanol.
  • a suitable diluent such as water and / or an organic solvent
  • tetrahydrofuran dioxane
  • dichloromethane chloroform
  • 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 formula (I) are suitable with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, to improve crop yields Quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and mollusks, used in agriculture, horticulture, livestock, aquaculture, forests, gardens and recreational facilities, in the protection of stored products and materials, and occur in the hygiene sector. 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
  • Nephotettix spp. Eg Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, 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, Perkinsiella spp., Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon
  • 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 Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., eg Cimex adjunetus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops, Tri
  • Cydia spp. Eg Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Egg dana saccharina, Ephestia spp., eg, Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., eg Euproctis chrysorrhoea , Euxoa spp., Felt
  • Stomopteryx subsecivella Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., Eg Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata; Pests from the strain of Mollusca, in particular from the class of bivalvia, for example Dreissena spp .; and from the class of Gastropoda eg Arion spp., eg Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., eg Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .
  • Animal and human parasites from the strains of Platyhelminthes and Nematoda eg Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, eg Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp. Ascaridia spp., Baylisascaris spp., Brugia spp., E.g.
  • Trichinella spiralis Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., eg Trichuris trichuria, Uncinaria spp., Wuchereria spp., eg Wuchereria bancrofti;
  • 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 ornata
  • Hemicycliophora spp. Heterodera spp., Eg Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmanieila spp., Hoplolaimus spp., Longidorus spp., Eg Longidorus africanus, Meloidogyne spp., Eg Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita , Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., Eg Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., Eg Pra
  • the order of coccidia can be determined, e.g. Eimeria spp. fight.
  • 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.
  • Formulations The present invention furthermore relates to formulations and use forms prepared therefrom as pesticides, such as, for example, pesticides.
  • 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 vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-demanding agents such.
  • 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 Specifications, 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.
  • the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • 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.
  • 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.
  • 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, chloroethylenes 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 such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such as cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as methanol, ethanol, Isopropanol, 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 dimethyl sulfoxide and water.
  • aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride
  • 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 alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydroly
  • auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, such as iron oxide, titanium oxide, Ferrocyanblau and organic Dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
  • dyes such as inorganic pigments, such as iron oxide, titanium oxide, Ferrocyanblau and organic Dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
  • 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.
  • 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.
  • additional auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • 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.
  • Suitable penetration promoters in the present context are 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 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. 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.
  • 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.
  • 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,
  • 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.
  • nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. 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, eg spinetoram and spinosad.
  • Chloride channel activators such as avermectins / milbemycins, eg, 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.
  • Anti-skinning agents especially in dipterans, i.e., two-toed, 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).
  • 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.
  • 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
  • Fungicides 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).
  • All of the listed five-component mixed partners of classes (1) to (15) can optionally form salts with corresponding bases or acids, provided that suitable functional groups are present.
  • tautomeric forms are also included for the listed ficcidial mixed partners 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- (2,4,6-trifluoro ⁇ henyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, (4.14) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4, 6-trifluorophenyl) -pyridazine.
  • 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, (1.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl ⁇ 3-methyl-l - [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamate.
  • 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.
  • compounds which may act as decouplers for example (14.01) binapacryl, (14.02) dinocap, (14.03) ferimzone, (14.04) fluazinam, (14.05) meptyldinocap.
  • 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
  • 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: 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 TM Insecticide, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen
  • 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 to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Peppers and chillies, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (eg cabbage), peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears , Citrus fruits and grapes).
  • cereals wheat, rice, triticale, barley, rye, oats
  • corn soybeans
  • potatoes sugar beets
  • sugarcane tomatoes
  • Peppers and chillies cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (eg cabbage), peas and other vegetables, cotton, tobacco,
  • 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.
  • Plants are to be understood as meaning all stages of development of the plants, for example seeds, cuttings and young (immature) plants through to mature plants.
  • 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 (harvested plants or plant parts) as well as vegetative and generative propagation material, for example 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) takes place directly or by acting on their environment, habitat or storage space according to the conventional treatment methods, for example by dipping, spraying, vaporizing, atomizing, spreading, brushing, injecting and propagating material, in particular in seeds, further by single or multi-layer wrapping.
  • 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 varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering 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 drought or to bottoms salt, 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 harvested 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, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes ), with particular emphasis on corn, soy, wheat, rice, potato, cotton, sugarcane, 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, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched 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. This may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i.
  • the compounds of formula (I) are incorporated in solid form (e.g., in the form of granules) at the plant site. In water rice crops, this may also be by metered addition of the compound of formula (I) in a solid form (e.g., as granules) into a flooded paddy field.
  • Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to 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 the protection of the seed and the germinating plant, which will increase the additional application of pesticides during storage make the sowing or after emergence of the plants redundant or at least significantly reduce. 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.
  • 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.
  • 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.
  • the individual substances may be contained in different layers on the seed.
  • 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. 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 formula (I) acts systemically is that the treatment of the seed not only the seed itself, but also the resulting Protects 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. 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.
  • 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. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • 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.
  • These formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents 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 trimethylene glycols. Stryrylphenolpolyglykolether 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.
  • 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.
  • Preferably mentioned are 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 maize, rice, rapeseed, peas, beans, cotton , Sunflower, soy and beet 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 procedure for pickling is to place the seed in a mixer in discontinuous or continuous operation, in each case the desired amount Mordant formulations added either as such or after prior dilution with water and mixed until uniform distribution of the formulation on 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.
  • the term 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 are of low toxicity to warm-blooded animals are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. 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 pets 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.
  • 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., Ornithodorus 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., Ornithodorus spp., Otobius spp.
  • Ixodidae such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp
  • Parasitic protozoa include: Mastigophora (Flagellata), such as Trypanosomatidae, for example Trypanosoma b. brucei, Tb gambiense, Tb 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.
  • Mastigophora Flagellata
  • Trypanosomatidae for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense
  • T. congolense T. cruzi
  • T. evansi T. equinum
  • T. lewisi T. per
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
  • Apicomplexa 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.
  • Eimeridae for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, 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. sitesdai E. suis, E. tenella, E.
  • 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.
  • 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. 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., Collyricum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus 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., Songyloides spp .; from the order Rhabditida, for example: S.
  • rongylus 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., O
  • 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 an antiectica, in particular an arthropodicide such as an insecticide or acaricide
  • an arthropodicide such as an insecticide or acaricide
  • 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).
  • vectors and their transmitted diseases or pathogens are: 1) mosquitoes - anopheles: malaria, filariasis;
  • 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, e.g. 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, e.g. 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 the formula (I) are present as ready-to-use pesticides, ie they can be applied to the appropriate material can be applied. As further insecticides or as fungicides in particular the above-mentioned in question.
  • 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, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins.
  • 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 NMR spectra were determined with an Avance 400 broker equipped with a 60 ⁇ volume flowhead probe. In individual cases, the NMR spectra were measured with a broker Avance II 600.
  • reaction mixture was stirred for 10 minutes at room temperature and then treated with 1.2 equivalents of the amine component. After about 16 hours of stirring at room temperature, the reaction mixture was concentrated in vacuo and the remaining residue purified by preparative chromatography (HPLC).
  • Emulsifier alkylaryl polyglycol ether
  • 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.
  • 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 which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. 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.
  • Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
  • the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed.

Abstract

The invention relates to novel bicyclic compounds of formula (I), to agents containing said compounds, and to the use thereof for controlling animal pests.

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. Kürzlich sind bicyclische Verbindungen bekannt geworden, die Insektizide Eigenschaften besitzen (WO 2015/038503 AI). 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. Recently, bicyclic compounds have become known which possess insecticidal properties (WO 2015/038503 Al).
In WO 2010/078408 AI ist die Darstellung und pharmazeutische Verwendung von Raf Kinase Inhibitoren und in WO 2013/259064 AI ist die Synthese von anti-HTV Agenzien und deren Verwendung zur Behandlung von HIV Infektionen beschrieben, die u. a. ein N-substituiertes 2H- Pyrazolo[3,4-£]pyridin-l-yl-Fragment enthalten. In WO 2010/056999 ist die Darstellung von Parasitiziden beschrieben, die ein N-substituiertes 2H-Pyrazolo[3,4-£]pyridin-l-yl-Fragment enthalten. In WO 2010/078408 Al the presentation and pharmaceutical use of Raf kinase inhibitors and in WO 2013/259064 AI the synthesis of anti-HTV agents and their use for the treatment of HIV infections is described which u. a. contain an N-substituted 2H-pyrazolo [3,4-] pyridin-1-yl fragment. WO 2010/056999 describes the preparation of parasiticides containing an N-substituted 2H-pyrazolo [3,4-] pyridin-1-yl fragment.
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 with 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-a) bis (A-f) A for an A residue from the series (Aa) to (Af)
(A-a) (A-a)
steht, worin die gestrichelte Linie die Bindung zum Stickstoffatom des Bicyclus der Formel (I) bedeutet und wherein the dashed line represents the bond to the nitrogen 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,
R2 a) für einen B-Rest aus der Reihe (B-l) bis (B-36) R 2 a) for a B radical from the series (B1) to (B-36)
(B-l)  (B-l)
(B-2) (B-3) (B-4) (B-2) (B-3) (B-4)
(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) (B1) (B-12)
(B-13) (B-14) (B-15) (B-16) (B-13) (B-14) (B-15) (B-16)
7) (B-18) (B-19) (B-20) 7) (B-18) (B-19) (B-20)
(B-21) (B-22) (B-23) (B-24) (B-21) (B-22) (B-23) (B-24)
(B-25) (B-26) (B-27) (B-28) (B-25) (B-26) (B-27) (B-28)
(B-29)  (B-29)
(B-30) (B-31) (B-32)  (B-30) (B-31) (B-32)
(B-33) (B-34) (B-35) (B-36) (B-33) (B-34) (B-35) (B-36)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) markiert, oder R2 b) für einen D-Rest aus der Reihe (D- 1 ) bis (D-3) in which the dashed line marks the bond to the carbon atom of the bicyclic compound of the formula (I), or R 2 b) represents 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) markiert, oder c) für einen Rest der Formel  (D-1) (D-2) (D-3), wherein the dotted line marks 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) markiert, oder d) für einen Rest der Formel wherein the dashed line marks the bond to the carbon atom of the bicycle of the formula (I), or d) a radical of the formula
X X
R22 R22
23 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) markiert, oder für einen F-Rest aus der Reihe (F-l) bis (F-l 1) 23, in which the dashed line marks the bond to the carbon atom of the bicyclic compound of the formula (I), or for an F radical from the series (Fl) to (Fl 1)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) markiert, oder wherein the dashed line marks the bond to the carbon atom of the bicycle of formula (I), or
R2 f) für einen Rest aus der Reihe Halogenalkyl, Carboxyl und Amino steht, worin R 2 f) is a radical from the series haloalkyl, carboxyl and amino, wherein
G2 für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, Alkyl, Halogenalkyl, Alkoxycarbonylalkyl, 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, Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl,G 2 is hydrogen or a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, alkoxycarbonylalkyl, 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 (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl,
Alkoxy(alkylsulfinyl)alkyl, Alkoxy(alkylsulfonyl)alkyl, Bis(alkylsulfanyl)alkyl, Bis(halogenalkylsulfanyl)alkyl, Bis(hydroxyalkylsulfanyl)alkyl, Alkoxycarbonyl,Alkoxy (alkylsulfinyl) 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, Alkylsulfmyl, 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 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) Alkoxycarbonylalkyl, alpha-hydroxyimino-alkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio, alkylsulfmyl, alkylsulfonyl, 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 themselves may in turn 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, imidazolyl, 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 themselves are substituted again may be halogen and alkyl), or a C-residue from the series (Cl) to (C-9)
<C > R8 (C"ß) (0)n (C"7) (O)n X (C"8) Y N. " <C> R 8 (C "ß (0) n (C)" 7) (O) n X (C "8) Y N."
I I  I i
R8 R8 R 8 R 8
(0)n (0) n
steht, worin die gestrichelte Linie die Bindung zu den Resten (B-l) bis (B-36) bedeutet, für Sauerstoff oder Schwefel steht, X1 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy und Halogenalkoxy steht, wherein the dashed line denotes the bond to the radicals (B1) to (B-36), represents oxygen or sulfur, X 1 is a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, 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 an 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, 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,
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 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 oder 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 or 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, 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, if appropriate 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 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,
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, 12 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
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, 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 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, 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-gliedrigenR 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 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, Ring which may contain one or more other 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 undR 16 is a radical from the series hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and
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 und R 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, Cycloalkenyl 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, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R and R 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 containing one or more further heteroatoms from the series sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and may contain 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 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,
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, 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 may contain one or more further heteroatoms selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
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 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 group consisting of sulfur, oxygen (where oxygen atoms are not allowed to 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 Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, 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 alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl , Alkylsulfinylalkyl, 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 Alkyl, gegebenenfalls durch Halogen, Carbamoyl, Thiocarbamoyl oder Cyano substituiertes Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyloxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkylthioalkyloxy, Alkylsulfinylalkyloxy, Alkylsulfonylalkyloxy, Halogenalkylthioalkyl, Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl, Alkylthioalkenyl, Alkylsulfinylalkenyl, Alkylsulfonylalkenyl, Alkenylthioalkyl, Alkenylsulfinylalkyl, Alkenylsulfonylalkyl, Alkylcarbonylalkyl, Halogenalkylcarbonylalkyl, Alkoxyalkyl, Halogenalkoxyalkyl, Alkoxycarbonylalkyl, Halogenalkoxycarbonylalkyl, Alkylaminosulfonyl, Dialkylaminosulfonyl steht, oder, im Fall R2 = d), auch für gegebenenfalls substituiertes Aryl oder für einen E-Rest aus der Reihe E-1 bis E-51 R 22 is a radical from the series alkyl, optionally substituted by halogen, carbamoyl, thiocarbamoyl or cyano substituted cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, Alkylthioalkyloxy, Alkylsulfinylalkyloxy, Alkylsulfonylalkyloxy, haloalkylthioalkyl, Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl, alkylthioalkenyl, Alkylsulfinylalkenyl, alkylsulfonylalkenyl, Alkenylthioalkyl, Alkenylsulfinylalkyl, Alkenylsulfonylalkyl, alkylcarbonylalkyl, Halogenalkylcarbonylalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxycarbonylalkyl, Halogenalkoxycarbonylalkyl, alkylaminosulfonyl, dialkylaminosulfonyl group, or, in the case of R 2 = d) also for optionally substituted aryl or for an E-radical from the series E-1 to E-51
E-8 E-9 E-10 E-1 1  E-8 E-9 E-10 E-1 1
E-16 E-17 E-16 E-17
E-35 E-36 E-35 E-36
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 Halogengenalkylsulfonyl steht, R 23 für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylthioalkyl, Alkenylthioalkyl, Cyanoalkyl, Alkoxyalkyl 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, R 23 is a radical from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl 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, für Wasserstoff oder Alkyl steht und  R is hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, is hydrogen or alkyl and
R 26 für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy- alkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl und Cyanoalkyl steht. R 26 is a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl.
Weiterhin wurde gefunden, dass die Verbindungen der Formel (I) 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. Furthermore, it has been found that the compounds of the formula (I) have good activity as pesticides, for example against arthropods and in particular insects, and, moreover, are generally very well tolerated by crops, in particular, and / or via favorable toxicological and / or favorable environmental factors Features.
Vorzugsbereich (1): Bevorzugt sind Verbindungen der Formel (I), in welchen Preferred range (1): Preference is given to compounds of the formula (I) in which
A für einen Rest aus der Reihe (A-a), (A-b) und (A-f) A is a radical from the series (A-a), (A-b) and (A-f)
(A-a) (A-a)
(A-b) (A-f) steht, worin die gestrichelte Linie die Bindung zum Stickstoffatom des Bicyclus der Formel (I) bedeutet, und G1 für N oder C-B1 steht, für einen Rest aus der Reihe Wasserstoff, Halogen, G-C6-Alkyl und Ci-C4-Halogenalkyl steht, für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C6-Alkyl und Ci-C4-Halogenalkyl steht, (Ab) (Af), wherein the dotted line represents the bond to the nitrogen atom of the bicyclic of formula (I), and G 1 represents N or CB 1 , a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl, is a radical from the series 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,
) für einen B-Rest aus der Reihe (B-1 ) bis (B-36) ) for a B residue from the series (B-1) to (B-36)
(B-1)  (B-1)
(B-2) (B-3) (B-4) (B-2) (B-3) (B-4)
(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-13) (B-14) (B-15) (B- 16)  (B-13) (B-14) (B-15) (B-16)
(B-17) (B-18) (B-19) (B-20) (B-17) (B-18) (B-19) (B-20)
(B-21) (B-22) (B-23) (B-24) (B-21) (B-22) (B-23) (B-24)
(B-25) (B-26) (B-27) (B-28) (B-25) (B-26) (B-27) (B-28)
(B-29)  (B-29)
(B-30) (B-31) (B-32)  (B-30) (B-31) (B-32)
(B-33) (B-34) (B-35) (B-36) (B-33) (B-34) (B-35) (B-36)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R b) für einen D-Rest aus der Reihe (D- 1 ) bis (D-3)  in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I), or R b) denotes 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 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
X X
INI ^ R22 INI ^ R22
I ?Q I ? Q
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
R2 e) für einen Rest aus der Reihe (F- 1 ), (F-8), (F- 10) und (F-11) R 2 e) is a radical from the series (F-1), (F-8), (F-10) and (F-11)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
R2 f) für einen Rest aus der Reihe Ci-C6-Halogenalkyl, Carboxyl und Amino steht, worin R 2 f) is a radical from the series Ci-C6-haloalkyl, carboxyl and amino, wherein
G2 für Wasserstoff oder für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, C1-C4- Alkylamino, Halogen-Ci-C4-alkylamino, Ci-C4-Dialkylamino, Ci-C4-Alkyl, Halogen-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl-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 C1-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, C1-C4- 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, 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 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, C1-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 G 2 is hydrogen or a radical from the group halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno-C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkyl, C 1 -C 6 -cycloalkyl -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) -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 (halo- Ci-C4-alkylsulfanyl) -C-C 4 alkyl, bis (hydroxy-Ci-C4-alkylsulfanyl) -C-C 4 alkyl, C 1 -C4- alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci- C 4 alkyl, a // the JAA-hydroxyimino-Ci-C4 - alkoxycarbonyl-Ci-C 4 alkyl, alpha-Ci-Ca-alkoxy imino-Ci-C4-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, 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 may itself 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 in turn has a substituent may be halogenated by halogen, cyano, nitro, C 1 -C 4 -alkyl and halogeno-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, halo-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy , halo-Ci-C4-alkoxy, Ci-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-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 themselves in turn may be substituted by halogen and C 1 -C 4 alkyl), or
G2 für einen C-Rest aus der Reihe (C- 1 ) und (C-6) bis (C-9) G 2 for a C radical from the series (C-1) and (C-6) to (C-9)
steht, worin die gestrichelte Linie die Bindung zu den Resten (B-l) bis (B-36) bedeutet, X für Sauerstoff oder Schwefel steht, X1 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Ci-Cö-Alkyl, CI-CÖ- Halogenalkyl, C3-C6-Cycloalkyl, CI-CÖ- Alkoxy und Ci-C6-Halogenalkoxy steht, X2 für Sauerstoff, Schwefel, NR5 oder NOH steht, in which the dashed line denotes the bond to the radicals (B1) to (B-36), X represents oxygen or sulfur, X1 represents a radical from the series consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl , CI-COE haloalkyl, C3-C6-cycloalkyl, CI-C Ö - alkoxy and Ci-C6-haloalkoxy, X 2 is oxygen, sulfur, NR 5 or NOH,
V-Z für R24CH-CHR25 oder R24C=CR25 steht, n für 1 oder 2 steht, 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 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-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- 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 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-C 1 -C 4 -alkyl, for R 18 -CO-C 1 -C 4 -alkyl, for NR 18 R 19 -CO-C 1 -C 4 -alkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = 0) Ci-C 4 alkyl, C 3 -C 8 cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted C3-C6-cycloalkyl, optionally mono- or disubstituted through oxygen ( to C = 0) Ci-C4 alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted C3-C8-cycloalkenyl, mono- or disubstituted (with oxygen optionally leads to C = 0) Ci-C4 alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted C3-C6 cycloalkyl-Ci-C4-alkyl, mono- or di-optionally substituted by Oxygen (leads to C = 0 ), Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted C3-C6-cycloalkenyl-Ci-C4-alkyl, (optionally substituted once or twice by oxygen leads to C = 0) Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl substituted heterocyclyl, optionally monosubstituted or disubstituted (with oxygen leads to C = 0) , C1-C4 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, Ci-C4-haloalkyl, C3-C6-cycloalkyl, Ci-C 4 alkoxy or Ci-C4-haloalkoxy, phenyl-Ci-C4-alkyl, hetaryl and hetaryl-Ci-C4- alkyl,
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-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, 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,
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 5 is a radical from the group of hydrogen, Ci-C4 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, 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-C4-alkyl, Cyano-Ci-C i-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 6 -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, 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, 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 Ci-C6-haloalkylsulfonyl substituted C1 -C6- alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl, each optionally substituted by halogen, Ci-COE-alkyl, Ci Coe-haloalkyl, Ci -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-Cö-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, oder 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-Cö-alkyl, heteroaryl-Ci-C6-alkyl or NR'R ", wherein R 'and R" independently of one another from a number of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3 -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-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-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 Form alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkoxy-substituted 5 to 7-membered ring which has one or two heteroatoms selected from the group consisting of sulfur, oxygen (oxygen atoms may not be directly adjacent) and nitrogen and / or at least one and preferably a 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), 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-C i-Alkylthio, Ci-C i-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C i-Halogenalkylsulfonyl, Ci-C i-Alkylamino, Di-(Ci-C i-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 denotes the bond to the C (X) group), a radical from the row in each case optionally substituted by methyl, cyano, carbamoyl, substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkyl Alkinyl, in each case optionally substituted by methyl, trifluoromethyl, halogen, cyano or carbamoyl, substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl and C3-C6-cycloalkenyl, 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 by Ci-C i-alkyl, C1-C4-haloalkyl, Ci-C i-alkoxy, Ci-C i -haloalkoxy, Ci-C i-alkylthio, Ci-C i -haloalkylthio, Ci-C4-haloalkylsulfinyl, Ci-C i -haloalkylsulphonyl, Ci-C i-alkylamino, di- (Ci-C i-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 i-C4-alkoxycarbonyl or Ci-C4-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, R16 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-C6-Alkyl, CI-CÖ- 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, 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 selected from the group consisting of hydrogen, in each case optionally 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 of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each optionally substituted by halogen, cyano, nitro, Ci-C6-alkyl, CI-CÖ-haloalkyl, C3-C6-cycl Oalkyl, 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-C 1 -C 2 -alkyl and heteroaryl-C 1 -C 2 -alkyl and an optionally 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, C 1 -C 6 -haloalkylsulfonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkylcarbonyl-substituted amino group,
R17 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, C3-C6-Cycloalkyl-Ci-C6-alkyl und 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 oder N-2-Oxo-l -methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-Cö-Alkyl, Ci-C6-Halogenalkyl, C3-C6- Cycloalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Ci-Cö-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-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-Cö-alkyl, Heteroaryl-Ci-C6-alkyl oder für 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, R 17 is a radical from the series in each case optionally substituted by halogen, Ci-C6-alkoxy, CI-CÖ-haloalkoxy, Ci-Cö-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, CI-CÖ-haloalkylsulfinyl, Ci C6-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, Ci-C6-alkoxy or Ci-C6-haloalkoxy substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl and C3-C6-cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl , N-thiomorpholinyl, N-thiomorpholinyl-l-oxide, N-thiomorpholinyl-l, l-dioxide, N-piperazinyl, Nl-methylpiperazinyl or N-2-oxo-l -methylpiperazinyl, each optionally substituted by halogen, cyano (also in Alkyl moiety), 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 -alkyl 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 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, Ci-C6 alkylcarbonyl, Ci-C 6 - Alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-Ci-Cö-alkyl, heteroaryl-Ci-C6-alkyl or NR 'R ", wherein R' and R" are each independently a radical selected from the group 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,
R8 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 17 in the radical (C-8) and in the radical (F-8) can also be used together with the NC (X) group to which they are attached, a saturated or unsaturated and optionally halogen, CI-C Form alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkoxy-substituted 5 to 7-membered ring which contains 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 may be taken together with the NC (X) group to which they are attached, for a residue from the series
stehen (worin der Pfeil jeweils die Bindung zum S-Atom im Rest (C-8) und im Rest (F-8) markiert), (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)),
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 group of hydrogen, hydroxy, optionally mono- or polysubstituted by halogen or monosubstituted or disubstituted by cyano substituted 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-C 4 alkoxy, C 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 C1-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, R 19 represents hydrogen, an alkali metal or alkaline earth metal ion or an optionally monosubstituted to monosubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or an optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted radical from the series 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 4 -alkyl, C 1 -C 4 -alkyl-S (0) -C 1 -C 4 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 4 -alkyl,
Y3 für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Ci-Cö-Alkyl, Ci-Cö-Halogenalkyl, C3- Ce-Cycloalkyl, Ci-Ce-Alkoxy, Ci-Ce-Halogenalkoxy und NR20R21 steht, für einen Rest aus der Reihe O, S, SO und SO2 steht, für einen Rest aus der Reihe Ci-C6-Alkyl, gegebenenfalls durch Halogen, Carbamoyl, Thiocarbamoyl oder Cyano substituiertes C3-C6-Cycloalkyl, Ci-C6-Halogenalkyl, Ci-C6-Alkoxy, Ci-C i-Halogenalkoxy, Ci-Ce-Alkoxy-Ci-Ce-alkyloxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci- C4-Alkylsulfonyl, Ci-C4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, C1-C4-Y 3 is a radical from the series consisting of hydrogen, halogen, cyano, 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 and NR 20 R 21 , is a radical from the series O, S, SO and SO2, a radical from the series Ci-C6-alkyl, optionally substituted by halogen, carbamoyl, thiocarbamoyl or cyano substituted C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci -C 6 -alkoxy, C 1 -C -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C4 haloalkylsulfinyl, C1-C4
Halogenalkylsulfonyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Ci-C4-Alkylsulfmyl-Ci-C4-alkyl, C1-C4- Alkylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyloxy, Ci-C4-Alkylsulfmyl-Ci-C4-alkyloxy, C 1-C4- Alkylsulfonyl-C i-C4-alkyloxy, C i-C4-Halogenalkylthio-C i-C4-alkyl, C 1 -C4-Haloalkylsulfonyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C 4 -Alkylsulfmyl-Ci-C 4 alkyl, C 1 -C4- alkylsulphonyl-Ci-C4-alkyl, Ci-C4-alkylthio-Ci -C 4 -alkyloxy, C 1 -C 4 -alkylsulfinyl-C 1 -C 4 -alkyloxy, C 1 -C 4 -alkylsulfonyl-C 1 -C 4 -alkyloxy, C 1 -C 4 -haloalkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy
Halogenalkylsulfinyl-Ci-C4-alkyl, Ci-C4-Halogenalkylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-C2- C4-alkenyl, Ci-C4-Alkylsulfmyl-C2-C4-alkenyl, Ci-C4-Alkylsulfonyl-C2-C4-alkenyl, C2-C4- Alkenylthio-Ci-C4-alkyl, C2-C4-Alkenylsulfmyl-Ci-C4-alkyl, C2-C4-Alkenylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl-Ci-C4-alkyl, Ci-C4-Halogenalkylcarbonyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci- C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, C1-C4- Halogenalkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylaminosulfonyl, Di-(Ci-C4-alkyl)-aminosulfonyl steht, im Fall R2 = d), auch für gegebenenfalls durch Halogen, Cyano, Nitro, Amino, Hydroxy, Ci-C6-Alkyl, CI-CÖ- Halogenalkyl, C2-Ce-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl, C3-Ce-Alkenyloxy, C3-C6- Alkinyloxy, Ci-C6-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C6-Alkoxycarbonyloxy, Ci-C6-Alkylamino, C3-C6-Alkenylamino, C3-C6-Alkinylamino, C3-C6-Cycloalkylamino, Ci-Cö-Alkylthio, C1-C4- Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Cs-Ce-Alkenylthio, Cs-Ce-Alkinylthio, Cs-Ce-Cycloalkylthio, Ci-C4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, CI-CÖ- Alkylcarbonyl, Aminocarbonyl, Ci-C6-Alkylaminocarbonyl, Di-(Ci-C6-alkyl)-aminocarbonyl, Ci- C6-Alkylcarbonylamino, Ci-C6-Alkylamino oder Ci-C6-Dialkylamino substituiertes Aryl steht oder für einen E-Rest aus der Reihe E-l bis E-51 Haloalkylsulfinyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfonyl-Ci-C4-alkyl, Ci-C4-alkylthio-C2-C4-alkenyl, Ci-C 4 -Alkylsulfmyl-C 2 -C 4 alkenyl, Ci- C 4 alkylsulfonyl-C 2 -C 4 alkenyl, C 2 -C 4 - alkenylthio-Ci-C 4 alkyl, C 2 -C 4 -Alkenylsulfmyl-Ci-C 4 alkyl, C 2 -C 4 alkenylsulfonyl -C-C 4 alkyl, Ci-C4-alkylcarbonyl-Ci-C4-alkyl, Ci-C4-haloalkylcarbonyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci- C 4 alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl, C 1 -C 4 - haloalkoxycarbonyl-Ci-C4-alkyl, Ci-C4-alkylaminosulfonyl, Di (Ci-C 4 -alkyl) -aminosulfonyl, in the case R 2 = d), also represents optionally by halogen, cyano, nitro, amino, hydroxy, Ci-C6-alkyl, CI-CÖ-haloalkyl, C 2 -Ce-alkenyl, C 2 -C 6 -alkynyl, Cs-Ce-cycloalkyl, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 6 -alkoxycarbonyloxy, C6-alkylamino, C3-C6-alkenylamino, C3-C6-alkynylamino, C3-C6-cycloalkylamino, C1-C6-alkylthio, C1-C4-alkylsulfmy 1, C 1 -C 4 -alkylsulfonyl, C 1 -C 6 -alkenylthio, C 1 -C 6 -alkynylthio, C 1 -C 6 -cycloalkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 6 -alkylcarbonyl, Aminocarbonyl, Ci-C6-alkylaminocarbonyl, di- (Ci-C6-alkyl) -aminocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylamino or Ci-C6-dialkylamino substituted aryl or for an E-radical from the series El to E-51
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-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, für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy, Ci-C6-Alkyl, Ci-Ce-Halogenalkyl, Cyano-Ci-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, C3-C6- Cycloalkyl-Ci-C6-alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C3-C6-Alkenyloxy, C3-C6- Alkinyloxy, C3-C6-Cycloalkyloxy, Ci-Cö-Alkylcarbonyloxy, C2-C6-Alkenylcarbonyloxy, C2-C6- Alkinylcarbonyloxy, C3-C6-Cycloalkylcarbonyloxy, Ci-C6-Alkoxycarbonyloxy, C1-C6- 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-C6-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, 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-E-48 E-49 E-50 E-51 stands for a radical from the series hydrogen, halogen, cyano, nitro, amino, hydroxy, Ci-C6-alkyl, Ci-Ce-haloalkyl, cyano-Ci-C 6 alkyl, C 2 -C 6 alkenyl, C C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -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, C 1 -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 -alkenylthio, C 3 -C 6 -alkynylthio, C 3 -C 6 -cycloalkylthio , Ci-Ce-alkylsulfinyl, Ci-C6 alkylsulfonyl, Ci-C 6 - alkylcarbonyl, Ci-C 6 alkoxyimino-Ci-C6 alkyl, Ci-C 6 alkoxycarbonyl, aminocarbonyl, CI-C Ö - alkylaminocarbonyl , di (Ci-C 6 alkyl) aminocarbonyl, aminothiocarbonyl, Cl-C Ö - alkylaminosulfonyl, Ci-C6-alkylsulfonylamino, Ci-C6-alkylcarbonylamino, CI-alkylthio COE carbonylamino, in each case optionally substituted by a radical from the series halogen, cyano, nitro, amino, hydroxy, Ci-Cö-alkyl or Ci-Cö-haloalkyl-substituted phenyl, phenoxy, pyridinyl and pyridinyloxy, is a radical from the series hydrogen, Ci -Cö-alkyl, C3-C6 cycloalkyl, Ci-COE-haloalkyl, C 3 -C 6 alkenyl, C 2 -C 6 alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, cyano-Ci- C 6 alkyl, C 6 - alkylcarbonyl, C2-C6 alkenylcarbonyl, Ci-C6 haloalkylcarbonyl, C2-C 6 -
Halogenalkenylcarbonyl, Ci-C6-Alkoxy-Ci-C6-alkyl, Ci-C6-Alkoxycarbonyl, Ci-Cö-Alkylsulfonyl und Ci-C6-Halogengenalkylsulfonyl steht, 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, 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, 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, für Wasserstoff oder Ci-C4-Alkyl steht und 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- Alkylthio-Ci-C2-alkyl, Ci-C4-Alkylsulfmyl-Ci-C2-alkyl, Ci-C4-Alkylsulfonyl-Ci-C2-alkyl und Cyano-Ci-C4-alkyl steht. Halogenalkenylcarbonyl, Ci-C 6 alkoxy-C 6 alkyl, Ci-C 6 alkoxycarbonyl, Ci-COE-alkylsulfonyl, and Ci-C is 6 -Halogengenalkylsulfonyl, a radical from the group of hydrogen, Ci-alkyl COE , 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, Is hydrogen or each 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, is hydrogen or is in each case 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, represents hydrogen or Ci-C 4 alkyl and a radical from the group of hydrogen, Ci-C 4 alkyl, Ci-C4 haloalkyl, C2-C 4 -A lkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 2 alkyl, C 1 -C4- Alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfmyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl and cyano-C 1 -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 Rest aus der Reihe (A-a), (A-b) und (A-f) A is a radical from the series (A-a), (A-b) and (A-f)
T  T
(A-a)  (A-a)
(A-b) (A-f) steht, worin die gestrichelte Linie die Bindung zum Stickstoffatom des Bicyclus der Formel (I) bedeutet,  (A-b) (A-f), wherein the dotted line represents the bond to the nitrogen 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, B 1 is a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C -haloalkyl,
B2 für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-Cö-Alkyl und Ci-C/i-Halogenalkyl steht, B 2 is a radical from the series consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 1 -haloalkyl,
T für Sauerstoff oder ein Elektronenpaar steht, T is oxygen or a pair of electrons,
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-3) (B-4) (B-2) (B-3) (B-4)
(B-5) (B-6) (B-7) (B-8) (B-5) (B-6) (B-7) (B-8)
(B-9) (B-10) (B-ll) (B-12) (B-9) (B-10) (B-II) (B-12)
(B-21) (B-22) (B-23) (B-24) (B-21) (B-22) (B-23) (B-24)
(B-28)  (B-28)
(B-25) (B-26) (B-27)  (B-25) (B-26) (B-27)
(B-31)  (B-31)
(B-32) (B-33) (B-34)  (B-32) (B-33) (B-34)
(B-35) (B-36) (B-35) (B-36)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R b) für einen Rest aus der Reihe (D-1) bis (D-3) in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I), or R b) represents a 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
X X
N ^ R22 N ^ R22
I ?Q  I? Q
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
R2 e) für einen F-Rest aus der Reihe (F-l), (F-8) und (F-10) R 2 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 R f) für einen Rest aus der Reihe Ci-Cö-Halogenalkyl, Carboxyl und Amino steht, worin wherein the dashed line represents the bond to the carbon atom in the formula (I), or R f) is a radical from the series Ci-Cö-haloalkyl, carboxyl and amino, wherein
G für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Ci-C i-Alkylamino, Halogen-Ci-C4-Alkylamino, Ci-C4-Dialkylamino, Ci-C4-Alkyl, Ci-C4-Alkoxycarbonyl-Ci-C4- alkyl, Halogen-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- 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, 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, Dihydrooxadiazmyl, Dihydrodioxazmyl, Dihydrooxazolyl, Dihydrooxazmyl und Pyrazolmonyl (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 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, C1-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-Cyclo-Ci-C4-alkyl) 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-G is hydrogen or a radical from the series halogen, nitro, amino, cyano, C 1 -C -alkylamino, halogeno-C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl 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, 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) -Ci-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) -Ci-C 4 alkyl, Ci-C4-alkoxycarbonyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl, C (X 2) NR 3 R 4, NR 6 R 7, C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, Oxathialyloxide, oxathiolanyloxide, oxathialpanyloxide, oxathiocanyloxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazmyl, dihydrodioxazmyl, dihydrooxazolyl, dihydrooxazmyl and pyrazolmonyl (which in turn may themselves be substituted by C 1 -C 4 -alkyl, halogeno-ci 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 halogeno-C 1 -C 4 -alkyl C 4 alkyl), the heteroaryl pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn substituted itself Ci-C may be substituted by halogen, nitro, C 1 -C4- alkyl, halo-Ci-C 4 alkyl, alkoxy 4 alkoxy, halogen-Ci-C 4, C 4 -alkoxy-Ci-C 4 alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl and C 3 -C 6- cyclo-C 1 -C 4 -alkyl) 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
C4-Alkyl), oder C 4 alkyl), or
G für einen C-Rest aus der Reihe (C- 1 ), (C-6) und (C-9) G for a C radical from the series (C-1), (C-6) and (C-9)
steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, X für Sauerstoff steht, wherein the dashed line indicates the bond to the B radicals, X stands for oxygen,
X1 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-C4-Alkoxy und Ci-C4-Halogenalkoxy steht, X 1 is 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, C 1 -C 4 -alkoxy and C4 haloalkoxy stands,
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 zuR 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-C2 Alkyl, for optionally single or double by oxygen (leads to
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-C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 6 -cycloalkyl, optionally substituted once or twice by oxygen (leads to C = O) ), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 8 -cycloalkenyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 C 4 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 6 -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-C 1 -C 4 -alkyl, 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 C 1 -C 4 -haloalkyl-substituted C 3 -C 6 - Cycloalkenyl-Ci-C4-alkyl, optionally substituted once or twice by oxygen (leads to C = 0), Ci-C4-alkyl, C 3 -C6-cycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkyl-substituted heterocyclyl , optionally single or double by oxygen (leads to 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, C1-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 Ci-C4-Alkyl steht, 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 by halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkyl 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, R 3 is C 1 -C 4 - Alkyl stands,
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 steht, R 4 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 6 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,
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-R 5 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 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl,
C4-Alkoxycarbonyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyl steht, C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R6 für Wasserstoff oder C1-C4- Alkyl steht, R7 für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl, Halogen-Ci-C t-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 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 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkyl, 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-C 1 -C 4 -alkyl, arylcyclo C 4 alkyl or hetaryl C 1 -C 4 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, 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, 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,
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- 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 is a radical from the group in each case optionally substituted by halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkoxy 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 by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkyl 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 consisting of sulfur, oxygen ( where oxygen atoms are not allowed to be immediately adjacent) and nitrogen can 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-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-C i-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, 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 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 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 -C4- 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 -C4- alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl Ci-C i-alkyl and heteroaryl-Ci-C i-alkyl or NR'R ", wherein R 'and R" are independently a radical from the series hydrogen and Ci-C i-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-C6-alkoxy, Ci-C6-haloalkoxy-substituted 5- to 7-membered ring forming one or two heteroatoms selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably can contain exactly one carbonyl group, in particular R 8 and R 9 together with the NS (0) n group to which they are attached may be a member of the series
stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert), (in which the arrow in each case marks the bond to the C (X) group),
R15 für einen Rest aus der Reihe jeweils gegebenenfalls durch Methyl substituiertes CI-CÖ- Alkyl, C2-C6- Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Methyl, Halogen, Cyano oder Carbamoyl substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-Ci-C2-alkyl und C3-C6- Cycloalkenyl steht, R 15 is a radical selected from the group each optionally substituted by methyl C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each optionally substituted by methyl, halogen, cyano or carbamoyl-substituted C 3 -C 6 -cycloalkyl, C3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl and C 3 -C 6 -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, 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,
R17 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, 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, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-l -oxid, N-Thiomorpholinyl-l , l -dioxid, N-Piperazinyl, N-l-Methylpiperazinyl oder N-2-Oxo-l -methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C i-Alkyl, Ci-C i-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, C1-C4- Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkylcarbonylamino, C1-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, C1-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 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-C2-alkyl, 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 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 S02 steht, wenn R2 für den Rest c) steht, für einen Rest aus der Reihe Ci-C6-Alkyl, gegebenenfalls durch Halogen, Carbamoyl, Thiocarbamoyl oder Cyano substituiertes C3-C6-Cycloalkyl, CI-CÖ- Halogenalkyl, Ci-C6-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C6-Alkoxy-Ci-C6-alkyloxy, C1-C4- Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylthio, C1-C4- Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Ci-C4-Alkylthio-Ci-C4-alkyl, C1-C4- Alkylsulfmyl-Ci-C4-alkyl, Ci-C4-Alkylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyloxy, Ci- C4-Alkylsulfinyl-Ci-C4-alkyloxy, Ci-C4-Alkylsulfonyl-Ci-C4-alkyloxy, Ci-C4-Halogenalkylthio- Ci-C4-alkyl, Ci-C4-Halogenalkylsulfinyl-Ci-C4-alkyl, Ci-C4-Halogenalkylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-C2-C4-alkenyl, Ci-C4-Alkylsulfinyl-C2-C4-alkenyl, Ci-C4-Alkylsulfonyl-C2-C4- alkenyl, C2-C4-Alkenylthio-Ci-C4-alkyl, C2-C4-Alkenylsulfmyl-Ci-C4-alkyl, C2-C4- Alkenylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl-Ci-C4-alkyl, Ci-C4-Halogenalkylcarbonyl-Ci- C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl- Ci-C4-alkyl, Ci-C4-Halogenalkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Alkylaminosulfonyl, Di-(Ci-C4- alkyl)-aminosulfonyl steht, wenn R2 für den Rest c) steht, für einen Rest aus der Reihe Wasserstoff, Ci-Cö-Alkyl, C2-C4- Alkenyl, C2-C4-Alkinyl, Ci-C4-Alkylthio-Ci-C4-alkyl, C2-C4-Alkenylthio-Ci-C4-alkyl, Cyano-Ci- C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl steht, wenn R2 für den Rest d) oder e) steht, 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-C4alkyl steht, oder, im Fall R2 = d), auch für gegebenenfalls durch Halogen, Cyano, Nitro, Amino, Hydroxy, Ci-Cö-Alkyl, C1-C6- Halogenalkyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-C4-Halogenalkoxy, Ci-Ce- Alkoxycarbonyloxy, Ci-C6-Alkylamino, Ci-Cö-Alkylthio, Ci-C4-Halogenalkylthio, C1-C4- Alkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-Cö-Alkylcarbonyl, Aminocarbonyl, CI-CÖ- Alkylaminocarbonyl, Di-(Ci-C6-alkyl)-aminocarbonyl, Ci-C6-Alkylcarbonylamino substituiertes Phenyl oder für einen E-Rest aus der Reihe R 17 is a radical from the series in each case optionally substituted by halogen, C 1 -C -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl-substituted C 1 -C 4 - alkyl, C2-C4 alkenyl and C2-C4 alkynyl, each optionally substituted by halogen, C1-C4 alkyl, Ci- C4-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, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl , N-thiomorpholinyl, N-thiomorpholinyl-l-oxide, N-thiomorpholinyl-l, l-dioxide, N-piperazinyl, Nl-methylpiperazinyl or N-2-oxo-l-methylpiperazinyl, in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C -alkyl, C 1 -C -haloalkyl, C 3 -C 6 -cycloalkyl, ci 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, ci 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 -haloalkoxy-C 1 -C 4 -alkyl alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkylcarbonyl, C1-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 hydrogen and Ci-C4-alkyl, a radical from the Hydrogen, hydroxy, in each case optionally mono- or polysubstituted by halogen or once or twice durc h cyano substituted Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S-Ci-C 3 alkyl, Ci-C 4 - Alkyl-S (O) -Ci-C 3 -alkyl, C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 3 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -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-C4-alkyl, Ci-C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, cyclopropyl, fluoro, chloro, bromo or cyano, substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl, for hydrogen; Alkali or alkaline earth metal ion or for an optionally mono- to quadruple by Ci-C4-alkyl-substituted ammonium ion or for each optionally mono- or polysubstituted by halogen or mono- or cyano-double-substituted radical from the series Ci-C 4 alkyl, Ci-C 4- alkoxy, Ci-C 4 -alkoxy-Ci-C 2 -alkyl , Ci-C 4 -alkyl-S-Ci-C 2 - alkyl, Ci-C 4 alkyl-S (0) -C-C 2 alkyl, and Ci-C 4 alkyl-S (0) 2 -C C 2 alkyl is a radical selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and Ci-C4-haloalkoxy is a radical from the series S, SO and S0 2 , when R 2 is the radical c), a radical from the series Ci-C6-alkyl, optionally substituted by halogen, carbamoyl, thiocarbamoyl or cyano substituted C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylthio, C1-C4 haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkylthio-Ci-C4-alkyl, C1-C 4 - Alkylsulfmyl-Ci- C 4 -alkyl, C 1 -C 4 -alkylsulfonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyloxy, C 1 -C 4 -alkylsulfinyl-C 1 -C 4 -alkyloxy, C 1 -C 4 -alkylsulfonyl -C 1 -C 4 -alkyloxy, C 1 -C 4 -haloalkylthio-C 1 -C 4 -alkyl, C 4 haloalkylsulfinyl-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkylsulfonyl-C 1 -C 4 -alkyl, Ci-C 4 alkylthio-C 2 -C 4 alkenyl, C 4 alkylsulfinyl-C 2 -C 4 alkenyl, Ci-C 4 alkylsulfonyl-C 2 -C 4 - alkenyl, C 2 -C 4 alkenylthio-Ci-C 4 alkyl, C 2 -C 4 -Alkenylsulfmyl-Ci-C 4 alkyl, C 2 -C 4 - alkenylsulfonyl-Ci-C4-alkyl, Ci-C4-alkylcarbonyl-Ci-C 4 alkyl, Ci-C4-haloalkylcarbonyl Ci-C 4 alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4- alkoxycarbonyl Ci-C 4 alkyl, Ci-C4-haloalkoxycarbonyl-Ci-C4-alkyl, Ci-C4-alkylaminosulfonyl, di (Ci-C 4 - alkyl) aminosulfonyl, when R is 2 for the rest c), represents a radical from the group of hydrogen, Ci-COE-alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4-alkylthio-Ci-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, when R 2 is the radical d) or e), is a radical from the group of hydrogen, Ci-COE-alkyl, C 2 - C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C 6 - Alkoxy, C 2 -C 6 - alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyloxy, Ci-C4-alkylthio-Ci-C4-alkyl, C2-C4-alkenylthio-Ci-C4-alkyl, cyano-Ci-C 4 - alkyl, Ci-C4-alkoxy-Ci-C4-alkyl is, or, in the case of R 2 = d), and is optionally substituted by halogen, cyano, nitro, amino, hydroxy, Ci-COE-alkyl, C1-C6 haloalkyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, Ci-C4-haloalkoxy, Ci-Ce alkoxycarbonyloxy, Ci-C6-alkylamino, Ci-COE-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C 4 alkylsulfonyl, Ci-COE-alkylcarbonyl, aminocarbonyl, CI-C Ö - alkylaminocarbonyl, di- (Ci-C6-alkyl) aminocarbonyl, Ci-C6-alkylcarbonylamino-substituted phenyl, or represents a radical from e- the series
für Wasserstoff oder Ci-Ci-Alkyl steht und RZb für Wasserstoff, Ci-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl- Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C2-alkyl, Ci-C4-Alkylthio-Ci-C2-alkyl, Ci-C4-Alkylsulfinyl-Ci-C2- alkyl, Ci-C4-Alkylsulfonyl-Ci-C2-alkyl oder Cyano-Ci-C4-alkyl steht. is hydrogen or Ci-Ci-alkyl and R Zb is hydrogen, C 1 -C 4 -alkyl, 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 , Ci-C4-alkoxy-Ci-C 2 alkyl, Ci-C4-alkylthio-Ci-C 2 alkyl, Ci-C4-alkylsulfinyl-Ci-C 2 - alkyl, Ci-C4 alkylsulfonyl Ci-C 2 -alkyl or cyano-Ci-C 4 -alkyl.
Vorzugsbereich (3): Ganz besonders bevorzugt sind Verbindungen der Formel (I), in welchen für einen Rest aus der Reihe (A-a), (A-b) und (A-f) Preferred Range (3): Very particular preference is given to compounds of the formula (I) in which, for a radical from the series (A-a), (A-b) and (A-f)
(A-a)  (A-a)
(A-b) (A-f) steht, worin die gestrichelte Linie die Bindung zum Stickstoffatom des Bicyclus der Formel (I) bedeutet,  (A-b) (A-f), wherein the dotted line represents the bond to the nitrogen 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, B 1 is a radical selected from the group consisting of hydrogen and fluorine, B 2 is hydrogen,
T für Sauerstoff oder ein Elektronenpaar steht, T is oxygen or a pair of electrons,
R für einen B-Rest aus der Reihe R for a B-residue from the series
(B-l) (B-l)
B-2) (B-3) (B-4) B-2) (B-3) (B-4)
(B-5) (B-9) (B-10) (B-l l) (B-5) (B-9) (B-10) (Bl l)
(B-12)  (B-12)
(B-21) (B-23) (B-25)  (B-21) (B-23) (B-25)
(B-27) (B-28) (B-31) (B-27) (B-28) (B-31)
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 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 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 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder R 2 d) is a radical of the formula 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-l), (F-8) und (F-10) R 2 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 wherein the dashed line represents the bond to the carbon atom in the formula (I), or
R2 f) für einen Rest aus der Reihe Ci-C6-Halogenalkyl, Carboxyl und Amino steht, worin R 2 f) is a radical from the series Ci-C6-haloalkyl, carboxyl and amino, wherein
G2 für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Ci-C4-Alkylamino, Halogen Ci-C4-Alkylamino, Ci-C4-Dialkylamino, C1-C4- Alkyl, Ci-C4-Alkoxycarbonyl-Ci-C4- alkyl, Halogen-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- 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 und Ci-C4-Alkylsulfonyl steht, oder G 2 is hydrogen or a radical selected from halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogeno C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl-Ci- -C 4 alkyl, halo-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-C4-alkyl, bis (Ci-C4-alkoxy) -C-C4-alkyl, bis (halo-Ci-C4-alkoxy) -C-C 4 alkyl, Ci-C4-alkoxy (Ci-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) 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) -Ci C4-alkyl, Ci-C 4 alkoxycarbonyl, Ci-C 4 alkoxycarbonyl-Ci-C 4 alkyl, C (X 2) NR 3 R 4, NR 6 R 7, C 4 alkylthio, C -Alkylsulfmyl -C 4 and C-C is 4 alkylsulfonyl, or
G2 für einen C-Rest (C- 1 ) oder (C-9) G 2 is a C-radical (C-1) or (C-9)
steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet, X für Sauerstoff steht, wherein the dashed line indicates the bond to the B radicals, X stands for oxygen,
XI 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,
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 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-R is NR 18 R 19 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) - C 1 -C 2 -alkyl, C 1 -C 2 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, for R 18 -CO-C 1 -C 2 -alkyl, for NR 18 R 19 -CO-Ci- C 2 -alkyl, for optionally mono- or disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -
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,Alkoxy or Ci-C 2 -haloalkyl or by an oxygen atom (leads to C = 0) substituted C3-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- to disubstituted by Ci-C 2 alkyl, Ci-C 2 -alkoxy or Ci- C 2 -haloalkyl substituted C3-C6 cycloalkyl-Ci-C 2 alkyl, optionally mono- or disubstituted 2 alkyl, Ci-C 2 alkoxy or C 2 -halogenoalkyl-substituted C3-C6-cycloalkenyl-Ci-C 2 alkyl by C, optionally substituted once or twice by Ci-C 2 alkyl, C 1 -C 2 - alkoxy or Ci-C 2 -haloalkyl substituted heterocyclyl, optionally optionally mono- or disubstituted by Ci-C 2 alkyl, Ci-C 2 alkoxy or Ci-C 2 haloalkyl substituted heterocyclyl Ci-C 2 alkyl or in each case 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-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 steht, R 3 is C 1 -C 4 -alkyl, R 4 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 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkoxycarbonyl, Ci- C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, 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, Ci-C4-Alkylthio-Ci-C4-alkyl steht, für Wasserstoff oder Ci-C4-Alkyl steht, R7 für einen Rest aus der Reihe Wasserstoff, Ci-C i-Alkyl, Halogen-Ci-C t-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 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 , C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, 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 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkyl, 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-C 1 -C 4 -alkyl, arylcyclo C 4 alkyl or hetaryl C 1 -C 4 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, gegebenenfalls durch Halogen, Ci-Cö-Alkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkyl und Cyano substituiertes C3-C6- Cycloalkylcarbonyl, 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, 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 optionally substituted by C 1 -C 6 -alkyl or aryl-C 1 -C 6 -alkyl,
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- 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 is a radical from the group in each case optionally substituted by halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkoxy 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 by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkyl 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 consisting of sulfur, oxygen ( where oxygen atoms are not allowed to be immediately adjacent) and nitrogen can 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-C i-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, 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 C 4 alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl Ci-C i-alkyl and heteroaryl-Ci-C i-alkyl or NR'R ", wherein R 'and R" are independently of one another a radical from the series of hydrogen and Ci-C i-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-C6-alkoxy, Ci-C6-haloalkoxy-substituted 5- to 7-membered ring forming one or two heteroatoms selected from the group 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), (in which the arrow in each case marks the bond to the C (X) group),
R17 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, 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, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-l -oxid, N-Thiomorpholinyl-l , l -dioxid, N-Piperazinyl, N-l -Methylpiperazinyl oder N-2-Oxo-l -methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Halogenalkylthio, C1-C4- Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkylcarbonylamino, C1-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, C1-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 C1-C4- Alkyl stehen, W für einen Rest aus der Reihe S, SO und SO2 steht, R 17 is a radical from the series in each case optionally substituted by halogen, C 1 -C -alkoxy, C 1 -C 4 -halogenoalkoxy, 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 -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 -haloalkyl, 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, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-l-oxide, N-thiomorpholinyl-l, l-dioxide, N-piperazinyl, Nl-methylpiperazinyl or 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 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 C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl sulfo nyl, 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 -alkyl haloalkoxy-Ci-C4-alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl-Ci-C4-alkyl, Ci-C 4 alkylcarbonyl, C 1 -C4- 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 stand, W is a radical from the series S, SO and SO2,
Y für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy und Trifluormethoxy steht, Y is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
R18 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, R 18 is a radical selected from the group consisting of hydrogen and hydroxy, in each case optionally mono-, di-, tri-, tetra- or trisubstituted by fluorine, chlorine or mono- or disubstituted cyano-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S-Ci-C 2 alkyl, Ci-C 4 alkyl-S (0) -C-C 2 alkyl, Ci- C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, C 1 -C 4 -alkylcarbonyl, 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 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,
R19 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, R 19 is hydrogen, an alkali or alkaline earth metal ion, for an optionally mono- to quadruple by Ci-C 4 alkyl substituted ammonium ion or for each optionally single, double, triple, quadruple or five times by fluorine, chlorine or mono- or disubstituted by cyano substituted 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) -C-C 2 alkyl, and Ci-C 4 alkyl-S (0) 2 -C-C 2 - alkyl,
R22 wenn R2 für den Rest c) steht für einen Rest aus der Reihe Ci-C6-Alkyl, gegebenenfalls durch Cyano substituiertes C3-C6-Cycloalkyl, Ci-C6-Halogenalkyl, Ci-C6-Alkoxy, C1-C4- Halogenalkoxy, Ci-Ce-Alkoxy-Ci-Ce-alkyloxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, C1-C4- Alkylsulfonyl, Ci-C4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Ci-C4-Alkylsulfmyl-Ci-C4-alkyl, Ci-C4-Alkylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-Ci-C4-alkyloxy, Ci-C4-Alkylsulfmyl-Ci-C4-alkyloxy, Ci-C4-Alkylsulfonyl-Ci- C4-alkyloxy, Ci-C4-Halogenalkylthio-Ci-C4-alkyl, Ci-C4-Halogenalkylsulfinyl-Ci-C4-alkyl, Ci- C4-Halogenalkylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylthio-C2-C4-alkenyl, Ci-C4-Alkylsulfinyl-C2-C4- alkenyl, Ci-C4-Alkylsulfonyl-C2-C4-alkenyl, C2-C4-Alkenylthio-Ci-C4-alkyl, C2-C4- Alkenylsulfmyl-Ci-C4-alkyl, C2-C4-Alkenylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl-Ci-C4- alkyl, Ci-C4-Halogenalkylcarbonyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4- Halogenalkoxy-Ci-C4-alkyl, Ci-C4-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Halogenalkoxycarbonyl- Ci-C4-alkyl, Ci-C4-Alkylaminosulfonyl, Di-(Ci-C4-alkyl)-aminosulfonyl steht, R 22 when R 2 is the radical c) is a radical from the series Ci-C6-alkyl, optionally substituted by cyano C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C4-haloalkoxy , Ci-Ce-alkoxy-Ci-Ce-alkyloxy, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, C1-C4 alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfinyl, Ci-C 4 haloalkylsulfonyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C 4 -Alkylsulfmyl-Ci-C4-alkyl, Ci-C 4 alkylsulfonyl-Ci-C4-alkyl, Ci-C4- alkylthio-Ci-C4-alkyloxy, alkyloxy Ci-C 4 -Alkylsulfmyl-C 4, C 4 alkylsulfonyl-Ci- C4-alkyloxy, Ci-C4-haloalkylthio-C 4 - alkyl, Ci-C4-haloalkylsulfinyl-Ci-C4-alkyl, Ci- C4-haloalkylsulfonyl-Ci-C4-alkyl, Ci-C 4 alkylthio-C 2 -C 4 -alkenyl, C 4 - alkylsulfinyl-C 2 -C 4 - alkenyl, Ci-C 4 alkylsulfonyl-C 2 -C 4 alkenyl, C 2 -C 4 alkenylthio-Ci-C 4 alkyl, C 2 -C 4 - Alkenylsulfmyl-Ci- C 4 alkyl, C 2 -C 4 alkenylsulfonyl-Ci-C4-alkyl, Ci-C4-alkylcarbonyl-Ci-C 4 - alkyl , Ci-C4-haloalkylcarbonyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 4 alkyl, C 1 -C 4 - haloalkoxy-Ci-C4-alkyl, Ci-C 4 alkoxycarbonyl -C-C 4 alkyl, Ci-C 4 -Halogenalkoxycarbonyl- Ci-C4 alkyl, Ci-C4-alkylaminosulfonyl, di (Ci-C 4 alkyl) aminosulfonyl group,
R23 wenn R2 für den Rest c) steht für einen Rest aus der Reihe Wasserstoff, Ci-C6-Alkyl, C2-C4- Alkenyl, C2-C -Alkinyl, Ci-C -Alkylthio-Ci-C -alkyl, C2-C -Alkenylthio-Ci-C -alkyl, Cyano- Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl steht, wenn R2 für den Rest d) steht für einen Rest aus der Reihe Ci-C i-Alkyl, gegebenenfalls durch Cyano substituiertes C3-C6-Cycloalkyl, Ci-C i-Halogenalkyl, Ci-C4-Alkylthio-Ci-C4-alkyl, Ci- C4-Alkylsulfmyl-Ci-C4-alkyl, Ci-C4-Alkylsulfonyl-Ci-C4-alkyl, Ci-C4-Halogenalkylthio-Ci-C4- alkyl, Ci-C4-Halogenalkylsulfinyl-Ci-C4-alkyl, Ci-C4-Halogenalkylsulfonyl-Ci-C4-alkyl, C1-C4- Alkylthio-C2-C4-alkenyl, Ci-C4-Alkylsulfinyl-C2-C4-alkenyl, Ci-C4-Alkylsulfonyl-C2-C4- alkenyl, C2-C4-Alkenylthio-Ci-C4-alkyl, C2-C4-Alkenylsulfmyl-Ci-C4-alkyl, C2-C4- Alkenylsulfonyl-Ci-C4-alkyl, Ci-C4-Alkylcarbonyl-Ci-C4-alkyl, Ci-C4-Halogenalkylcarbonyl- Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl, C1-C4- Alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-Halogenalkoxycarbonyl-Ci-C4-alkyl, C1-C4- Alkylaminosulfonyl, Di-(Ci-C4-alkyl)-aminosulfonyl steht, wenn R2 für den Rest d) oder e) steht 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-C4alkyl steht, und im Fall R2 = d) auch für gegebenenfalls durch Halogen, Cyano, Nitro, Amino, Hydroxy, Ci-Cö-Alkyl, C1-C6- Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, Ci-C6-Alkoxy, Ci-C6- Halogenalkoxy, C3-C6-Alkenyloxy, C3-C6-Alkinyloxy, Ci-C6-Alkoxycarbonyloxy, CI-CÖ- Alkylamino, C3-C6-Alkenylamino, C3-C6-Alkinylamino, C3-C6-Cycloalkylamino, CI-CÖ- Alkylthio, Ci-C6-Halogenalkylthio, C3-C6-Alkenylthio, C3-C6-Alkinylthio, C3-C6- Cycloalkylthio, Ci-Ce-Alkylsulfmyl, Ci-Ce-Alkylsulfonyl, Ci-Ce-Alkylcarbonyl, Aminocarbonyl, Ci-C6-Alkylaminocarbonyl, Di-(Ci-C6-alkyl)-aminocarbonyl, CI-CÖ- Alkylcarbonylamino substituiertes Phenyl oder für einen der folgenden E-Reste R 23 when R 2 is the radical c) is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C -alkynyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl- alkyl, C 2 -C alkenylthio-Ci-C alkyl, cyano, Ci-C4-alkyl, Ci-C 4 -alkoxy-Ci-C 4 alkyl, when R 2 is the radical d) is a radical from the series Ci-C i-alkyl, optionally substituted by cyano C3-C6-cycloalkyl, Ci-C i -haloalkyl, Ci-C 4 -alkylthio-Ci-C 4 alkyl, Ci- C4 -Alkylsulfmyl-Ci-C4-alkyl, Ci-C 4 alkylsulfonyl-Ci-C4-alkyl, Ci-C4-haloalkylthio-C 4 - alkyl, Ci-C 4 - haloalkylsulfinyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfonyl-Ci-C 4 alkyl, C 1 -C 4 - alkylthio-C 2 -C 4 alkenyl, C 4 alkylsulfinyl-C 2 C 4 alkenyl, Ci-C4-alkylsulfonyl-C2-C 4 - alkenyl, C 2 -C 4 alkenylthio-Ci-C 4 alkyl, C 2 -C 4 -Alkenylsulfmyl-Ci-C 4 alkyl, C 2 - C 4 - alkenylsulfonyl-Ci-C4-alkyl, Ci-C4-alkylcarbonyl-Ci-C4-alkyl, Ci-C 4 -Halogenalkylcarbonyl- Ci-C4 alkyl, Ci-C 4 -alkoxy-C 4 alkyl, Ci-C4-haloalkoxy-Ci-C 4 alkyl, C 1 -C4- alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-haloalkoxycarbonyl-Ci-C 4 alkyl, C 1 -C 4 -alkylaminosulfonyl, di- (C 1 -C 4 -alkyl) -aminosulfonyl, when R 2 is the radical d) or e) is a radical from the R eIHE hydrogen, Ci-COE-alkyl, C 2 - C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, 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, Ci-C 4 alkyl is alkoxy-Ci-C 4, and in the case of R 2 = d) and optionally substituted by halogen, cyano, nitro, amino, hydroxy, Ci-COE-alkyl, C1-C6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Ci-C 6 alkoxy, Ci-C6 - haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, 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 -alkenylthio, C 3 - C 6 -alkynylthio, C 3 -C 6 -cycloalkylthio, C 1 -C -alkylsulfmyl, C 1 -C 6 -alkylsulfonyl, C 1 -C -alkylcarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di (C 1 -C 6 -alkyl) aminocarbonyl, CI- C Ö - alkylcarbonylamino substituted phenyl or one of the following the E-radicals
für einen Rest aus der Reihe Wasserstoff, Methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, Propenyl, Propargyl, Cyclopropyl, Cyclopropylmethyl, Methoxymethyl, Methylthioethyl, Methylsulfinylethyl, Methylsulfonylethyl und Cyanomethyl steht. Vorzugsbereich (4): Eine hevorgehobene Gruppe von Verbindungen der Formel (I) sind solche, in welchen is a radical selected from the group consisting of hydrogen, methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl, propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl, methylthioethyl, methylsulfinylethyl, methylsulfonylethyl and cyanomethyl. Preferred Range (4): A preferred group of compounds of the formula (I) are those in which
A für einen Rest aus der Reihe (A-a), (A-b) und (A-f) A is a radical from the series (A-a), (A-b) and (A-f)
(A-a)  (A-a)
(A-b) (A-f) steht, worin die gestrichelte Linie die Bindung zum Stickstoffatom des Bicyclus der Formel (I) bedeutet,  (A-b) (A-f), wherein the dotted line represents the bond to the nitrogen 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, B 1 is a radical selected from the group consisting of hydrogen and fluorine, B 2 is hydrogen,
T für ein Elektronenpaar steht, c) für den Rest der Formel T is an electron pair, c) the rest of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, für Sauerstoff steht, für Ci-C4-Alkyl steht, in which the dashed line represents the bond to the carbon atom of the bicyclic compound of the formula (I), is oxygen, is C 1 -C 4 -alkyl,
R für einen Rest aus der Reihe Ci-Cö-Alkyl, C3-C6-Cycloalkyl, Ci-C6-Halogenalkyl, Ci-C6-Alkoxy, Ci-C i-Alkylsulfonyl und Di-(Ci-C4-alkyl)-aminosulfonyl steht und R23 für Wasserstoff oder Ci-C6-Alkyl steht. R is a radical selected from C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C -alkylsulfonyl and di (C 1 -C 4 -alkyl) -aminosulfonyl and R 23 is hydrogen or C 1 -C 6 -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. In den bevorzugten Definitionen, deren Kombination den Vorzugsbereich (1) bildet, ist, sofern nichts anderes angegeben ist, 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 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, 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 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, Benzisofuryl, 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, 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 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, benzisofuryl, 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 Erdalkaliion ausgewählt aus der Reihe Beryllium, Magnesium, Calcium, Strontium, Barium, bevorzugt aus der Reihe Magnesium, Calcium, Cation for an alkali ion selected from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or an 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, Aryl (also as part of a larger unit, such as, for example, arylalkyl) selected from the group consisting of phenyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents 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, Heterocyclyl ausgewählt aus der Reihe Azetidinyl, Azolidinyl, Azinanyl, Oxetanyl, Oxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl, Thianyl, Tetrahydrofuryl, Piperazinyl, Morpholinyl. Hetaryl (synonymous with heteroaryl, also as part of a larger unit, such as hetarylalkyl) selected from 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 the series 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 Cation for an alkali metal ion from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or a
Erdalkaliion aus der Reihe Beryllium, Magnesium, Calcium, Strontium, Barium, bevorzugt aus der Reihe Magnesium, Calcium, Beryllium, magnesium, calcium, strontium, barium alkaline earth metal, preferably magnesium, calcium,
Heterocyclyl für Oxetanyl, Thiethanyl, Tetrahydrofuryl und Morpholinyl. Aryl für 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. Heterocyclyl for oxetanyl, thiethanyl, tetrahydrofuryl and morpholinyl. Aryl for phenyl, hetaryl (equivalent to heteroaryl, also as part of a larger moiety, 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. 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. 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. Halogen for fluorine, chlorine, bromine and iodine, preferably again fluorine, chlorine and bromine. Halo-substituted radicals, for example 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. Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl, in each case also in combination with heteroatoms, for example in alkoxy, may be straight-chain or branched as far as possible.
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. in front.
Wenn T im Rest A der Formel (A-a) When T in the radical A of the formula (A-a)
(A-a) für Sauerstoff steht, liegt der Rest als Pyridin-N-Oxid-derivat der Formel vor. Auf die Darstellung der Formalladungen (+ am Stickstoff und - am Sauerstoff) wurde hier verzichtet. (Aa) is oxygen, the remainder is a pyridine-N-oxide derivative of the formula 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)). Erfindungsgemäß besonders bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (2)). 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)). 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)). Erfindungsgemäß insbesonders bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als hervorgehoben aufgeführten Bedeutungen vorliegt (VorzugsbereichVery particular preference according to the invention is given to compounds of the formula (I) in which a combination of the meanings listed above as being very particularly preferred is present (preferred range (3)). Particular preference according to the invention is given to compounds of the formula (I) in which a combination of the meanings listed above as highlighted is present (preferred range
(4))· (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 (A-a)
(A-a) steht.  (A-a) stands.
Eine weiter bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für den Rest der Formel (A-b) A further preferred embodiment of the invention relates to compounds of the formula (I) in which A represents the radical of the formula (Ab)
(A-b) (From)
steht. Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für den Rest der F stands. A further preferred embodiment of the invention relates to compounds of the formula (I) in which A represents the radical of the F
(A-f) (A-f)
steht. Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für Pyridin-3-yl steht. stands. 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. A further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyrimidin-5-yl.
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 pyridazin-4-yl.
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 die unter a) aufgeführten Bedeutungen hat. 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 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).
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. A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 has the meanings listed under d).
Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 die unter e) aufgeführten Bedeutungen hat. 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 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).
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 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-N) 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 (IN) 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 Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-A) In a preferred embodiment, the invention relates to compounds of the formula (I-A)
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-B) In a further preferred embodiment, the invention relates to compounds 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 (IC)
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 (IE)
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 (IF)
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 (IG)
R 23 R8 R 23 R8
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 (IH)
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-L) 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-M) In a further preferred embodiment, the invention relates to compounds of the formula (I-M)
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 den Formeln (I-A) bis (I-N) haben die Variablen G2, R, R3, R8, R22, R23 W, X1, Y2 und n die weiter oben genannten Bedeutungen. In the formulas (IA) to (IN), the variables G 2 , R, R 3 , R 8 , R 22 , R 23 W, X 1 , Y 2 and n have the meanings mentioned above.
Die erfindungsgemäßen 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) according to the invention and their acid addition salts and metal salt complexes have good activity, in particular for controlling animal pests, which include arthropods and in particular insects.
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. The compounds of formula (I) may also be optionally substituted as stereoisomers, i.e., depending on the nature of the substituents. as geometric and / or as optical isomers or mixtures of isomers are present in different compositions. 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. Vorzugsweise werden jedoch die optisch aktiven, stereoisomeren Formen der Verbindungen der Formel (I) und deren Salze erfindungsgemäß verwendet. 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. Preferably, however, the optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention.
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. Suitable salts of the compounds of general formula (I) may be conventional non-toxic salts, i. H. 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.
Weiter wurde gefunden, dass sich die Verbindungen der Formel (I) nach den im Folgenden beschriebenen Verfahren herstellen lassen. It has furthermore been found that the compounds of the formula (I) can be prepared by the processes described below.
Verbindungen der Formel (I), in denen der Heterocyclus A für gegegebenenfalls mit einem Rest B2 substituiertes Pyrimdin-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 Reaktions Schema I in zwei Schritten hergestellt werden. Reaktionsschema I Compounds of the formula (I) in which the heterocycle A is pyrimdin-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) can be prepared, for example, according to the reaction scheme I be made in two steps. Reaction scheme I
bzw. (A-4)  or (A-4)
Im Reaktionsschema I haben A und R2, sofern nichts anderes angegeben ist, die oben genannten Bedeutungen. Beispielsweise können die 2-substituierten 5-Nitro-4-pyridincarboxaldehyde der Formel (A-1) mit den entsprechenden 3-aminosubstituierten Heterocyclen der Formel (A-2) in Gegenwart von sauren Reaktionshilfsmitteln in einem ersten Reaktionsschritt zu Verbindungen der Formel (A-3) umgesetzt werden, die dann in einem zweiten Reaktionsschritt in Gegenwart eines geeigneten Phosphor(III)- reagenz, beispielsweise Triethylphosphit, reduktiv unter Bildung der Verbindungen (A-4) cyclisiert werden. In Reaction Scheme I, A and R 2 , unless otherwise indicated, have the meanings given above. For example, the 2-substituted 5-nitro-4-pyridinecarboxaldehydes of the formula (A-1) with the corresponding 3-amino-substituted heterocycles of the formula (A-2) in the presence of acid reaction auxiliaries in a first reaction step to compounds of formula (A- 3), which are then reacted in a second reaction step in the presence of a suitable phosphorus (III) - reagent, for example triethyl phosphite, are reductively cyclized to form the compounds (A-4).
Wird bei dem erfindungsgemäßen Verfahren zur Herstellung der Verbindungen der Formel (I) als Verbindung der Formel (A-l) der 4-Formyl-5-nitro-2-pyridinecarbonsäure-methylester (R2 = COOCH3) and als Verbindung der Formel (A-2) 3-Pyridinamin (A = Pyridin-3-yl) eingesetzt, so entsteht zunächst der 4-[(l.Zi)-2-(Dimetliylammo)ethenyl]-5-nitro-2-pyridinecarbonsäuremethylester (A = 3-Pyridin-3-yl, R2 = COOCH3) als sogenannte„Schiff Base ". Nachfolgende Reduktion und Cyclisierung führt dann zur 5-substituierten 2-(Pyridin-3-yl)-2H-pyrazolo[3,4-c]pyridin-5-carbonsäure (A-4, A = Pyridin-3-yl, R2 = COOCH3), das als Startkomponente für die Verbindungen der Formel (I) verwendet werden kann (vgl. Herstellungsbeispiele). Is in the process of the invention for preparing the compounds of formula (I) as the compound of formula (Al) of 4-formyl-5-nitro-2-pyridinecarboxylic acid methyl ester (R 2 = COOCH3) and as the compound of formula (A-2 ) 3-pyridinamine (A = pyridin-3-yl) is used, the first is the 4 - [(l.Zi) -2- (Dimetliylammo) ethenyl] -5-nitro-2-pyridinecarbonsäuremethylester (A = 3-pyridine 3-yl, R 2 = COOCH 3) as so-called "Schiff base." Subsequent reduction and cyclization then leads to the 5-substituted-2- (pyridin-3-yl) -2H-pyrazolo [3,4-c] pyridine-5 carboxylic acid (A-4, A = pyridin-3-yl, R 2 = COOCH 3), which can be used as a starting component for the compounds of formula (I) (see Preparation Examples).
Azomethinderivate oder sogenannte „Schiff Basen " von aminosybstituierten Heterocyclen haben verschiedenartige Anwendungen (bilden z. B. Metallkomplexe bzw. sind biologisch aktiv) und können nach üblichen Verfahren, (vgl. auch V. Shama, et al, Intern. J. Univ. Pharm. Bio Science 2013, 2, 241- 57 und darin zitierte Literatur) erhalten werden. Die Verbindungen der Formel (A-l) sind teilweise bekannt und kommerziell erhältlich (z. B. für R2 = Br, 2-Brom-5-nitro-isonicotinaldehyd / Anichem Product List) bzw. können nach im Prinzip bekannten Herstellungsverfahren (für R2 = Cl; 2-Chlor-5-nitro-4-pyridincarboxaldehyd, WO 2010/026121 AI ; R2 = NH2; 2-Amino-5-nitro-4-pyridincarboxaldehyd, M. Andaloussi et al., Tetrahedron Lett. 48, 8392- 8395, 2007) erhalten werden. Beispelsweise läßt sich der 4-Formyl-5-nitro-2-pyridinecarbonsäure-methylester (R2 = COOCH3) aus 4- Methyl-5-nitro-2-pyridincarbonsäuremethylester via NN-Dimethylformamid-O, O-dimethylacetal Reaktion und anschließender Natriumperiodat-Oxidation gemäss Reaktionsschema II synthetisieren (vgl. Herstellungsbeispiele, Synthese von Zwischen-produkten). Azomethine derivatives or so-called "Schiff bases" of amino-substituted heterocycles have various applications (for example, form metal complexes or are biologically active) and can be synthesized by conventional methods (see also V. Shama, et al, Internal J. Univ Bio Science 2013, 2, 241-57 and literature cited therein.) The compounds of the formula (A1) are known in some cases and are commercially available (for example for R 2 = Br, 2-bromo-5-nitro-). isonicotinaldehyde / Anichem Product List) or can be prepared by methods known in principle (for R 2 = Cl; 2-chloro-5-nitro-4-pyridinecarboxaldehyde, WO 2010/026121 Al; R 2 = NH 2 ; 2-amino-5-one nitro-4-pyridinecarboxaldehyde, M. Andaloussi et al., Tetrahedron Lett., 48, 8392-8395, 2007.) For example, the methyl 4-formyl-5-nitro-2-pyridinecarboxylate (R 2 = COOCH 3) can be obtained. from 4-methyl-5-nitro-2-pyridincarbonsäuremethylester via NN-dimethylformamide O, O-dimethylacetal reaction and then he synthesize sodium periodate oxidation according to Reaction Scheme II (cf. Preparation Examples, Synthesis of Intermediates).
Reaktionsschema II Reaction scheme II
Die Verbindungen der Formel (A-2) sind teilweise bekannt und kommerziell erhältlich bzw. können nach im Prinzip bekannten Herstellungsverfahren erhalten werden, vgl. beispielsweise für A = 5-Fluor- pyridin-3-yl (A-a; B2 = H, G1 = C-F; T = Elektronenpaar) (WO 2011/ 123751 A2); Pyrazin-2-yl (A-b; B2 = H) (WO 2012/ 151567 AI); Pyridazin-4-yl (A-c; B2 = H) (WO 2011/038572 AI); Thiazol-5-yl (A- d; B2 = H) (JP 4600 6049 B4); Isothiazol-4-yl (A-e; B2 = H) (US 2839529) oder 1 -Methyl- lH-pyrazol- 4-yl (A-f; B2 = Η, R3 = CH3). The compounds of the formula (A-2) are known in some cases and are commercially available or can be obtained by production processes known in principle, cf. for example, for A = 5-fluoropyridin-3-yl (Aa; B 2 = H, G 1 = CF; T = electron pair) (WO 2011/123751 A2); Pyrazine-2-yl (Ab; B 2 = H) (WO 2012/151567 Al); Pyridazin-4-yl (Ac; B 2 = H) (WO 2011/038572 Al); Thiazole-5-yl (A d; B 2 = H) (JP 4600 6049 B4); Isothiazol-4-yl (Ae; B 2 = H) (US 2839529) or 1-methyl-1H-pyrazol-4-yl (Af; B 2 = Η, R 3 = CH 3 ).
Die Verbindungen der Formel (A-3) können nach dem im Schritt 1 des genannten Herstellungsverfahrens oder nach im Prinzip bekannten Synthesemethoden erhalten werden, vgl. beispielsweise die Herstellung des 4-Methyl-N-[(3-nitro-4-pyridinyl)methylen]-benzamins (H. E. Baumgarten et al, J. Amer. Chem. Soc. 77, 2438-2440, 1955). The compounds of the formula (A-3) can be obtained by the synthesis method known in step 1 of the said preparation process or according to the principle known, cf. for example, the preparation of 4-methyl-N - [(3-nitro-4-pyridinyl) methylene] -benzamine (Baumgarten, H.E., et al., J. Amer. Chem. Soc., 77, 2438-2440, 1955).
Schliesslich lassen sich die Verbindungen der Formel (I) gemäß Schritt 2 des genannten Herstellungsverfahrens mittels einer reduktiven Cyclisierung der 4-Imino-5-nitro-pyridine der Formel (A-3), beispielsweise gemäß der Candogan Indazolsynthese in Gegenwart von Triethylphosphit, erhalten (vgl. J. I. G. Candogan et al., J. Chem. Soc. 1965, 4831 ; N. E. Genung et al, Org. Lett. 16, 3114-3117, 2014 sowie Synthese von Azaindazolen: WO 2008/147822 AI und WO 2010/056999). Finally, the compounds of the formula (I) can be obtained in accordance with step 2 of the stated preparation process by means of a reductive cyclization of the 4-imino-5-nitropyridines of the formula (A-3), for example in accordance with the Candogan indazole synthesis in the presence of triethyl phosphite ( See JIG Candogan et al., J.Chem.Soc., 1965, 4831; NE Genung et al., Org. Lett. 16, 3114-3117, 2014, and Synthesis of Azaindazoles: WO 2008/147822 A1 and WO 2010/056999). ,
Alternativ können auch variierte Reaktionsbedingungen der reduktiven Cyclisierung nach Candogan et al. genutzt werden oder entsprechende alternative Reaktionsbedingungen Verwendung finden, wie beispielsweise die Übergangsmetall-katalysierte reduktive Cyclisierung von Imino-nitroaromaten und die termische Übergangsmetall-katalysierte Cyclisierung von 2-Azido-iminen (vgl. N. E. Genung et al., Org. Lett. 2014, 16, 3114-3117 und darin zitierte Literatur). Alternatively, varied reaction conditions of the reductive cyclization according to Candogan et al. or corresponding alternative reaction conditions are used, such as the transition metal-catalyzed reductive cyclization of imino-nitroaromatics and the thermal transition metal-catalyzed cyclization of 2-azido-imines (see NE Genung et al., Org. Lett., 2014, 16 , 3114-3117 and references cited therein).
In Gegenwart des Phosphor(III)-reagenz erfolgt zunächst die Reduktion der Nitrogruppe in dem Substrat (A-3) unter Ausbildung einer Nitrosogruppe (vgl. N. E. Genung et al., Org. Lett. 2014, 16, 3114-3117), aus der anschließend ein Nitren oder ein Nitren-ähnliches Intermediat gebildet wird, das anschließend intramolekular eine Cyclisierung bewirkt. Neben Triethylphosphit können auch Tricyclohexylphosphin, Tri-(n-butyl)-phosphin oder Tri-(tert-butyl)-phosphin (M.-A. Armour et al., J. Chem. Soc., Perkin Trans. 2 1975, 1185-1189; N. E. Genung et al., Org. Lett. 2014, 16, 31 14-3117) als alternative Phosphor(III)-reagenzien eingesetzt werden können. In the presence of the phosphorus (III) reagent, the reduction of the nitro group in the substrate (A-3) first takes place to form a nitroso group (see NE Genung et al., Org. Lett. 2014, 16, 3114-3117) then a nitrene or a nitrene-like intermediate is formed, which then causes an intramolecular cyclization. In addition to triethyl phosphite, tricyclohexylphosphine, tri (n-butyl) phosphine or tri (tert-butyl) phosphine (M.A. Armor et al., J. Chem. Soc., Perkin Trans. 2 1975, 1185 -1189; NE Genung et al., Org. Lett. 2014, 16, 31 14-3117) can be used as alternative phosphorus (III) reagents.
Verbindungen der Formel (I), in denen R2 für einen Rest aus der Reihe (B-1) bis (B-36) steht, können beispielsweise aus Verbindungen der Formel (I), in denen R2 für Halogen aus der Reihe Brom und lod steht, nach bekannten Methoden (Methode A: vgl. J. C. Antilla et al., J. Org. Chem., 2004, 69, 5578- 5587 und Methode B: vgl. H. Dong et al., Org. Lett., 2011, 13, 2726 - 2729; Ch. O. Ndubaku et al., J. Med. Chem., 2013, 56, 4597 - 4610; T. Furuya et al, J. Am. Chem. Soc, 2010, 132, 3793-3807) hergestellt werden. Verbindungen der Formel (I), in denen R2 für Halogen, beispielsweise Brom oder lod, steht, können gemäß dem Reaktionsschema I aus den entsprechenden 2-halogenierten 6-Formyl-5-nitro-pyridinen (A- 1) erhalten werden. Beispielsweise können die Verbindungen der Formel (I), in denen R2 für einen Rest (B-2), (B-21) oder (B-23) steht, gemäß Reaktionsschema III erhalten werden. Compounds of the formula (I) in which R 2 is a radical from the series (B-1) to (B-36) can be prepared, for example, from compounds of the formula (I) in which R 2 is halogen from the series bromine and iodine, according to known methods (Method A: see JC Antilla et al., J. Org. Chem., 2004, 69, 5578-5587 and Method B: see H. Dong et al., Org. , 2011, 13, 2726-2729; Ch.O. Ndubaku et al., J. Med. Chem., 2013, 56, 4597-4610; T. Furuya et al., J. Am. Chem. Soc., 2010, 132 , 3793-3807). 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 the corresponding 2-halogenated 6-formyl-5-nitro-pyridines (A-1). For example, the compounds of the formula (I) wherein R 2 is a radical (B-2), (B-21) or (B-23) can be obtained according to Reaction Scheme III.
Reaktionsschema III Reaction scheme III
Im Reaktionsschema III besitzen die Verbindung (I-e) und (B-21), in denen G die weiter oben genannte Bedeutung hat, eine gegebenenfalls in-situ erzeugte nucleofuge Abgangsgruppe LG ( "Leaving Group "). In Reaction Scheme III, the compounds (I-e) and (B-21) in which G has the above-mentioned meaning have a nucleofuge leaving group LG ("Leaving Group") which may be generated in situ.
Verbindungen der Formel (I), in denen R für einen Rest (B-l), (B-2), (B-10), (B-29) oder (B-30) steht, können nach der literaturbekannten Methode A bevorzugt in Gegenwart von Kupfer(I)-iodid und basischen Reaktionshilfsmitteln, wie beispielsweise iraft -N,N'-Dimethylcyclohexan-l,2-diamin und Kaliumcarbonat, in einem geeigneten Lösungs- oder Verdünnungsmittel hergestellt werden. Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe. Bevorzugt werden aromatische Kohlenwasserstoffe wie beispielsweise Toluol eingesetzt. Compounds of the formula (I) in which R represents a radical (B1), (B-2), (B-10), (B-29) or (B-30) can preferably be prepared by the method A known from the literature Presence of copper (I) iodide and basic reaction auxiliaries, such as iraft -N, N'-dimethylcyclohexane-l, 2-diamine and potassium carbonate, are prepared in a suitable solvent or diluent. 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.
Die Herstellung von Verbindungen der Formel (I), in denen R für einen Rest (B-3) bis (B-9), (B-l 1) bis (B-28) und (B-31) bis (B-33) steht, kann in Anlehnung an die im Reaktionsschema III gezeigten Methoden B und C erfolgen. Beispielsweise können die Verbindungen (B-3) bis (B-9), (B-11) bis (B-28) und (B-31) bis (B-33) mit einer geeignetenAbgangsgruppe (LG = B(OH)2) oder (Hetero)arylboronsäureester (LG = B(OR)2) mit den entsprechenden Verbindungen der Formel (I-a) nach bekannten Methoden (vgl. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58, 9633-9695; Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004) in Gegenwart geeigneter Katalysatoren aus der Reihe der Übergangsmetallsalze zu Verbindungen der Formel (I-B-3) bis (I-B-9), (I-B-l 1) bis (I- B-28) und (I-B-31) bis (I-B-33) umgesetzt werden. The preparation of compounds of the formula (I) in which R is a radical (B-3) to (B-9), (B1) to (B-28) and (B-31) to (B-33) can be carried out in accordance with the methods B and C shown in Reaction Scheme III. For example, the compounds (B-3) to (B-9), (B-11) to (B-28) and (B-31) to (B-33) may be exemplified by a suitable leaving group (LG = B (OH) 2 ) or (hetero) arylboronic acid ester (LG = B (OR) 2) with the corresponding compounds of the formula (Ia) by known methods (compare Chem. Rev. 1995, 95, 2457-2483, Tetrahedron 2002, 58, 9633-9695 Metal-Catalyzed Cross-Coupling Reactions (eds .: A. de Meijere, F. Diederich), 2 nd ed., Wiley-VCH, Weinheim, 2004) in the presence of suitable transition metal salts catalysts to give compounds of formula (IB -3) to (IB-9), (IB11) to (I-B-28) and (IB-31) to (IB-33).
Die Verbindungen (B-3) bis (B-9), (B-11) bis (B-l 3) und (B-21) bis (B-33) mit einer geeigneten Abgangsgruppe (LG = B(OH)2 oder (Hetero)arylboronsäureester, LG = B(OR)2) sind teilweise bekannt bzw. können nach allgemein bekannten Methoden hergestellt werden: z. B. 1 -(Methyl- lH-pyrazol-4-yl)- boronsäure [(B-3), LG = B(OH)2, G2 = Wasserstoff, WO 2009/155527], 2-Phenyl-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-oxazol [(B-6), LG = B(OCMe2)2, G2 = Phenyl, WO 2010/094755]; Thiazol-2-yl-boronsäure [(B-7), LG = B(OH)2, G2 = Wasserstoff, US 6310095 Bl]; 5-Phenyl- 1,2,4- thiadiazol-3-yl-boronsäure [(B-13), LG = B(OH)2, G2 = Phenyl, DE 19710614 AI], Pyridin-3-yl- boronsäure [(B-21) vs (B-22), LG = B(OH)2, G2 = Wasserstoff, WO 2013/186089]; l,3,5-Triazin-2-yl- boronsäure [(B-28), LG = B(OH)2, G2 = Wasserstoff, KR 2011/079401]. Compounds (B-3) to (B-9), (B-11) to (Bl 3) and (B-21) to (B-33) having a suitable leaving group (LG = B (OH) 2 or ( Hetero) arylboronic acid esters, LG = B (OR) 2) are known in some cases or can be prepared by generally known methods: for. B. 1 - (methyl-1H-pyrazol-4-yl) boronic acid [(B-3), LG = B (OH) 2 , G 2 = hydrogen, WO 2009/155527], 2-phenyl-4- ( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -oxazole [(B-6), LG = B (OCMe 2 ) 2 , G 2 = phenyl, WO 2010/094755] ; Thiazol-2-ylboronic acid [(B-7), LG = B (OH) 2 , G 2 = hydrogen, US 6310095 Bl]; 5-phenyl-1,2,4-thiadiazol-3-ylboronic acid [(B-13), LG = B (OH) 2 , G 2 = phenyl, DE 19710614 Al], pyridin-3-ylboronic acid [ (B-21) vs (B-22), LG = B (OH) 2 , G 2 = hydrogen, WO 2013/186089]; l, 3,5-triazin-2-ylboronic acid [(B-28), LG = B (OH) 2 , G 2 = hydrogen, KR 2011/079401].
Alternativ können die Verbindungen der Formel (I-a) zunächst mittels literaturbekannten Methoden in Verbindungen der Formel (I-e) überführt werden, die dann anschließend mit Halogen-aktivierten Heterocyclen gemäß Reaktionsschema III nach Methode C (vgl. T. Ishiyama et al, J. Org. Chem., 1995, 60, 7508 - 7510; WO 2010/151601) weiterreagieren. Halogen-aktivierte Verbindungen (B-3) bis (B-9), (B-l 1) bis (B-13) und (B-21) bis (B-33) sind teilweise bekannt bzw. können nach allgemein bekannten Methoden hergestellt werden: z. B. 3-Brom-4,5- dihydro-1 -phenyl- lH-pyrazol [(B-18), LG = Br, G2 = Phenyl, J. Elguero et al., Bull. Soc. Chim. France 1996, 5, 1683-1686]. Alternatively, the compounds of the formula (Ia) can first be converted by means of methods known from the literature into compounds of the formula (Ie) which are then subsequently reacted with halogen-activated heterocycles according to Reaction Scheme III according to Method C (see T. Ishiyama et al, J. Org. Chem., 1995, 60, 7508-7510, WO 2010/151601). Halogen-activated compounds (B-3) to (B-9), (B1) to (B-13) and (B-21) to (B-33) are partly known or can be prepared by generally known methods : z. 3-bromo-4,5-dihydro-1-phenyl-1H-pyrazole [(B-18), LG = Br, G 2 = phenyl, J. Elguero et al., Bull. Soc. Chim. France 1996, 5, 1683-1686].
Die Herstellung von Verbindungen der Formel (I), in denen R2 für einen Rest (B-21) oder (B-23) steht, können in Anlehnung an die im Reaktionsschema III gezeigten literaturbekannten Methoden B und C bevorzugt in Gegenwart von geeignete Kupplungskatalysatoren, basischen Reaktionshilfsmitteln, und in einem geeigneten Lösungs- oder Verdünnungsmittel durchgeführt werden. Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe. Bevorzugt werden aromatische Kohlenwasserstoffe wie beispielsweise Toluol eingesetzt. The preparation of compounds of the formula (I) in which R 2 is a radical (B-21) or (B-23) can, based on the methods B and C shown in Reaction Scheme III, preferably in the presence of suitable coupling catalysts , basic reaction auxiliaries, and in a suitable solvent or diluent. 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.
Die Herstellung von Verbindungen der Formel (I), in denen R für einen Rest (B-3) bis (B-9), (B-l 1) bis (B-28) und (B-31) bis (B-33) steht, können in Anlehnung an die im Reaktionsschema III gezeigten Methoden B und C bevorzugt in Gegenwart von geeigneten Kupplungskatalysatoren, basischen Reaktionshilfs-mitteln, und in einem geeigneten Lösungs- oder Verdünnungsmittel durchgeführt werden. The preparation of compounds of the formula (I) in which R is a radical (B-3) to (B-9), (B1) to (B-28) and (B-31) to (B-33) Based on the methods shown in Reaction Scheme III, B and C can preferably be carried out in the presence of suitable coupling catalysts, basic reaction auxiliaries, and in a suitable solvent or diluent.
Als Kupplungskatalysatoren kommen beispielsweise bevorzugt Palladium Katalysatoren wie [1,1 '-Bis (diphenylphosphino)ferrocen]dichlorpalladium (II) oder Tetrakis(triphenylphosphin)palladium in Betracht. Als geeignete basische Reaktionshilfsmittel zur Durchführung der Verfahren gemäss Reaktionsschema III finden bevorzugt Carbonate des Natriums oder Kaliums Verwendung. Examples of suitable coupling catalysts are palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) or tetrakis (triphenylphosphine) palladium. Suitable basic reaction auxiliaries for carrying out the processes according to Reaction Scheme III are preferably carbonates of sodium or potassium.
Bevorzugt werden Nitrile wie Acetonitril, Benzonitril, insbesondere Acetonitril, oder Ether wie Diethylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan, insbesondere 1 ,2-Dimethoxyethan in Kombination mit Wasser eingesetzt. Verbindungen der Formel (I), in denen R2 für einen Rest aus der Reihe (C-l) bis (C-9) oder für CX- NR22R23 steht, können beispielsweise aus Verbindungen der Formel (I), in denen R2 für eine Carboxylgruppe steht, nach geeigneter Aktivierung (d.h. LG steht für eine gegebenenfalls in-situ erzeugte nucleofuge Abgangsgruppe) mittels bekannter Methoden hergestellt werden. Preference is given to nitriles such as acetonitrile, benzonitrile, in particular acetonitrile, or ethers such as diethyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, in particular 1, 2-dimethoxyethane used in combination with water. Compounds of the formula (I) in which R 2 is a radical from the series (Cl) to (C-9) or CX-NR 22 R 23 may be prepared, for example, from compounds of the formula (I) in which R 2 is a carboxyl group, after appropriate activation (ie LG is an optionally generated in situ nucleofuge leaving group) can be prepared by known methods.
Beispielsweise können die Verbindungen der Formel (I), in denen R2 für einen Rest (C-l) oder für CX- NR22R23 steht, gemäß Reaktionsschema IV erhalten werden (vgl. auch Herstellungsbeispiele für (I-C-l): A = 5-Fluor-pyridin-3-yl; R8 = H, R9 = N(CH3)2, n = 2 in Beispiel 10; (I-d): A = Pyridin-3-yl; R22, R23 = CH3 in Beispiel 7). For example, the compounds of the formula (I) in which R 2 is a radical (Cl) or CX-NR 22 R 23 can be obtained according to Reaction Scheme IV (see also Preparation Examples for (ICl): A = 5-fluoro -pyridin-3-yl; R 8 = H, R 9 = N (CH 3 ) 2 , n = 2 in Example 10; (Id): A = pyridin-3-yl; R 22 , R 23 = CH 3 in Example 7).
Reaktionsschema IV Reaction scheme IV
LG = Leaving group, z. B. Halogen, O-CO-R (R = Aryl, Alkyl) (|-d)  LG = Leaving group, z. Halogen, O-CO-R (R = aryl, alkyl) (| -d)
A/-lmidazol-1-yl, etc.  A / -imidazol-1-yl, etc.
Verbindungen der Formel (I), in denen R für Carboxyl steht, können gemäß Reaktionsschema I aus entsprechenden 4-Formyl-5-nitro-2-pyridinecarbonsäure-methylestern (A-l ; R2 = COOR) erhalten werden. Die nach-folgende Esterspaltung nach üblichen Methoden führt dann zu den Verbindungen der Formel (I-b). Compounds of the formula (I) in which R is carboxyl can be obtained in accordance with Reaction Scheme I from corresponding methyl 4-formyl-5-nitro-2-pyridinecarboxylates (Al; R 2 = COOR). The subsequent ester cleavage by conventional methods then leads to the compounds of formula (Ib).
Als Kondensationsmittel zur Aktivierung der Carbonsäuren der Formel (I-b) kommen alle üblicherweise für derartige Amidierungsreaktionen verwendbaren Kondensationsmittel infrage. Beispielhaft genannt seien Säurehalogenidbildner wie Phosgen, Phosgenderivate wie Carbonyl-diimidazol (CDI), 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(dimethyl- amino)phosphonium-hexafluorphosphat (BOP), Bis(2-oxo-3-oxazolidinyl)phosphoniumsäurechlorid (BOP-Cl), N,NN',N'-Bis(tetramethylen)cloruronium-tetrafluorborat, 0-( H-Benzotriazol- 1 -yl)- NNN'.N -tetramethyluronium-hexafluorphosphat (HBTU), 0-(7H-Benzotriazol- 1 -yl)-N,NN',N - bis(tetramethylen)uronium-hexafluorphosphat, 0-( H-Benzotriazol- 1 -yl)-N,NN',N -tetramethyluro- nium-tetrafluorborat (TBTU), 0-( H-Benzotriazol-l-yl)-N,N,N',N -bis(tetramethylen)uronium- tetrafluorborat, 0-(7-Azabenzotriazol- 1 -yl)-N,NN',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. Suitable condensing agents for activating the carboxylic acids of the formula (Ib) are all condensing agents customarily used for such amidation reactions. Examples which may be mentioned are acid halide formers such as phosgene, phosgene derivatives such as carbonyldiimidazole (CDI), 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-l, 2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyrrolidinophosphonium hexafluorophosphate (BROP), 0- (H-benzotriazol-1-yloxy) tris (dimethylamino ) phosphonium hexafluorophosphate (BOP), bis (2-oxo-3-oxazolidinyl) phosphoniumsäurechlorid (BOP-Cl), N, NN ', N' -bis (tetramethylene) cloruronium tetrafluoroborate, 0- (H-benzotriazole- 1 - yl) - NNN '.N -tetramethyluronium hexafluorophosphate (HBTU), 0- (7H-benzotriazole-1-yl) -N, NN', N - uronium hexafluorophosphate bis (tetramethylene), 0- (1 H-benzotriazole -yl) -N, NN ' , N-tetramethyluronium tetrafluoroborate (TBTU), 0- (H-benzotriazol-1-yl) -N, N, N ' , N-bis (tetramethylene) uronium tetrafluoroborate, 0 - (7-Azabenzotriazol-1-yl) -N, NN ' , N tetramethyluronium hexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt) and 4- (4,6-dimethoxy-l, 3,5-triazin-2-yl) -4-methylmorpholinium salt (DMT.MM), mostly available as chloride. These reagents may be used separately or optionally in combination.
Zur gezielten Aktivierung der Verbindungen mit der Formel (I-b) können aber auch gemischte Anhydride (LG = COOR) verwendet werden, die zur Darstellung von Verbindungen der Formel (I-C-l) und (I-d) führen (vgl. G. W. Anderson et al. J. Am. Chem. Soc. 1967, 89, 5012-5017). Bei diesem Verfahren können verschiedene Chlorameisensäureester zum Einsatz kommen, wie z.B. Chlorameisensäureisobutylester (LG = COOR mit R = wo-Butyl) und Chlorameisensäure-isopropylester (LG = COOR mit R = z o-Propyl). Ebenfalls können dafür Diethylacetylchlorid, Trimethylacetylchlorid und ähnliche Verbindungen verwendet werden. Die nachfolgende Reaktion der aktivierten Verbindungen der Formel (I-c) mit den jeweiligen Aminkomponenten nach Reaktionsschema IV wird gegebenenfalls in Gegenwart eines geeigneten Reaktionshilfstoffes und in Gegenwart eines geeigneten Lösungs- oder Verdünnungsmittels durchgeführt. For targeted activation of the compounds of the formula (Ib), it is also possible to use mixed anhydrides (LG = COOR) which lead to the preparation of compounds of the formula (ICl) and (Id) (see GW Anderson et al., J. Am Chem. Soc. 1967, 89, 5012-5017). Various chloroformates may be used in this process, e.g. Isobutyl chloroformate (LG = COOR with R = ω-butyl) and isopropyl chloroformate (LG = COOR with R = z o-propyl). Also, diethylacetyl chloride, trimethylacetyl chloride and the like can be used therefor. The subsequent reaction of the activated compounds of the formula (I-c) with the respective amine components according to Reaction Scheme IV is optionally carried out in the presence of a suitable reaction auxiliary and in the presence of a suitable solvent or diluent.
Als geeignete Reaktionshilfsstoffe finden basische Reaktionshilfsmittel zur Durchführung der Verfahren gemäss Reaktionsschema IV Verwendung. Suitable reaction auxiliaries are basic reaction auxiliaries for carrying out the processes according to Reaction Scheme IV.
Beispielhaft seien erwähnt die Hydroxide, Hydride, Oxide und Carbonate des Lithiums, Natriums, Kaliums, Magnesiums, Calciums und Bariums, ferner weitere basische Verbindungen wie Amidinbasen oder Guanidinbasen wie 7-Methyl-l,5,7-triaza-bicyclo(4.4.0)dec-5-en (MTBD); Diazabicyclo(4.3.0)nonen (DBN), Diazabicyclo(2.2.2)octan (DABCO), 1,8-Diazabicyclo(5.4.0)undecen (DBU), Cyclohexyltetrabutyl-guanidin (CyTBG), Cyclohexyltetramethylguanidin (CyTMG), Ν,Ν,Ν,Ν- Tetramethyl-l,8-naphthalindiamin, Pentamethylpiperidin, tertiäre Amine wie Triethylamin, Trimethylamin, Tribenzylamin, Triisopropylamin, Tributylamin, Tricyclohexylamin, Triamylamin, Trihexylamin, NN-Dimethylanilin, NN-Dimethyl-toluidin, NN-Dimethyl-p-aminopyridin, N-Methyl- pyrrolidin, N-Methyl-piperidin, N-Methyl-imidazol, N-Methyl-pyrazol, N-Methyl-morpholin, N-Methyl- hexamethylendiamin, Pyridin, 4-Pyrrolidinopyridin, 4-Dimethylamino-pyridin, Chinolin, α-Picolin, ß- Picolin, Isochinolin, Pyrimidin, Acridin, NNN',N'-Tetramethylendiamin, NN',N'-Tetraethylendiamin, Chinoxalin, N-Propyl-diisopropylamin, N-Ethyl-diisopropylamin (Hünig's Base), NN'-Dimethyl- cyclohexylamin, 2,6-Lutidin, 2,4-Lutidin oder Triethyldiamin. Examples include the hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium, further basic compounds such as amidine bases or guanidine bases such as 7-methyl-l, 5,7-triaza-bicyclo (4.4.0 ) dec-5-ene (MTBD); Diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) octane (DABCO), 1,8-diazabicyclo (5.4.0) undecene (DBU), cyclohexyltetrabutyl-guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), Ν , Ν, Ν, Ν-tetramethyl-l, 8-naphthalenediamine, pentamethylpiperidine, tertiary amines such as triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, triamylamine, trihexylamine, N, N-dimethylaniline, N, N-dimethyl-toluidine, N, N-dimethyl p-aminopyridine, N-methylpyrrolidine, N-methyl-piperidine, N-methyl-imidazole, N-methyl-pyrazole, N-methyl-morpholine, N-methyl-hexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylamino pyridine, quinoline, α-picoline, β-picoline, isoquinoline, pyrimidine, acridine, NNN ', N'-tetramethylenediamine, NN', N'-tetraethylenediamine, quinoxaline, N-propyl-diisopropylamine, N-ethyl-diisopropylamine (Hünig's Base ), N, N'-dimethylcyclohexylamine, 2,6-lutidine, 2,4-lutidine or triethyldiamine.
Als basische Reaktionshilfsmittel zur Durchführung der Verfahren gemäss Reaktionsschema IV können alle geeigneten Säurebindemittel eingesetzt werden, beispielsweise Amine, insbesondere tertiäre Amine, sowie Alkali- und Erdalkaliverbindungen. As basic reaction auxiliaries for carrying out the processes according to Reaction Scheme IV it is possible to use all suitable acid binders, for example amines, in particular tertiary amines, and also alkali metal and alkaline earth metal compounds.
Zur Herstellung von Verbindungen der Formel (I-C-l) oder (I-d) werden vorzugsweise tertiäre Amine wie N-Propyl-diisopropylamin oder N-Ethyl-diisopropylamin (DIEA; Hünig's Base) eingesetzt. Als geeignete 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, Tetrahydrof ran, 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. For the preparation of compounds of the formula (ICl) or (Id) it is preferred to use tertiary amines, such as N-propyldiisopropylamine or N-ethyldiisopropylamine (DIEA; Hünig's base). 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 -Methylformanilid, N-methylpyrrolidone, hexamethylphosphoric triamide) and dimethyl sulfoxide or water or mixtures of said solvents.
Bevorzugt werden Amide, beispielsweise NN-Dimethylformamid, als Lösungsmittel eingesetzt. Verbindungen der Formel (I), in denen R2 für einen Rest aus der Reihe (D-1) bis (D-3) steht, können beispielsweise aus Verbindungen der Formel (I), in denen R2 für Halogen aus der Reihe Brom und lod steht, nach im Prinzip bekannten Methoden hergestellt werden. Amides, for example N, N-dimethylformamide, are preferably used as solvent. Compounds of the formula (I) in which R 2 is a radical from the series (D-1) to (D-3) can be prepared, for example, from compounds of the formula (I) in which R 2 is halogen from the series bromine and iodine, are prepared by methods known in principle.
Beispielsweise können die Verbindungen der Formel (I), in denen R2 für einen Rest aus der Reihe (D-1) bis (D-3) steht, gemäß dem Reaktionsschema V nach literaturbekannten Methoden (vgl. US2013/0267493; T. Furuya et al., J. Am. Chem. Soc., 2010, 132, 3793-3807) erhalten werden. For example, the compounds of the formula (I) in which R 2 is a radical from the series (D-1) to (D-3), according to Reaction Scheme V according to literature methods (see US2013 / 0267493, T. Furuya Chem. Soc., 2010, 132, 3793-3807).
Reaktionsschema V Reaction scheme V
Im Reaktionsschema V besitzen die Verbindungen (D-2), in denen W für S, SO oder SO2 steht, eine gegebenenfalls in-situ erzeugte nucleofuge Abgangsgruppe LG. In Reaction Scheme V, the compounds (D-2) in which W is S, SO or SO 2 have an optionally in-situ generated nucleofugic leaving group LG.
Beispielsweise können die Verbindungen (D-1) bis (D-3) mit einer geeignetenAbgangsgruppe (LG = B(OH)2 oder (Hetero)arylboronsäureester, LG = B(OR)2) mit den entsprechenden Verbindungen der Formel (I-a) nach bekannten Methoden (vgl. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58, 9633-9695; Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004) in Gegenwart geeigneter Katalysatoren aus der Reihe der Übergangsmetallsalze zu Verbindungen der Formeln (I-D-l) bis (I-D-3) umgesetzt werden. For example, compounds (D-1) to (D-3) having a suitable leaving group (LG = B (OH) 2 or (hetero) arylboronic acid ester, LG = B (OR) 2 ) may be reacted with the corresponding compounds of formula (Ia) Chem. Rev. 1995, 95, 2457-2483, Tetrahedron 2002, 58, 9633-9695, Metal-Catalyzed Cross-Coupling Reactions (Ed .: A. de Meijere, F. Diederich), 2 nd ed ., Wiley-VCH, Weinheim, 2004) in the presence of suitable catalysts from the series of transition metal salts to compounds of the formulas (IDl) to (ID-3).
Die Herstellung von Verbindungen der Formel (I), in denen R2 für einen Rest (D-l) bis (D-3) steht, können in Anlehnung an Reaktionsschema V bevorzugt in Gegenwart von geeigneten Kupplungskatalysatoren, basischen Reaktionshilfsmitteln, und in einem geeigneten Lösungs- oder Verdünnungsmittel durchgeführt werden. The preparation of compounds of the formula (I) in which R 2 is a radical (D1) to (D-3) can be carried out in the presence of suitable coupling catalysts, basic reaction auxiliaries and in a suitable solvent, in accordance with Reaction Scheme V. or diluents.
Als Kupplungskatalysatoren kommen beispielsweise bevorzugt Palladium Katalysatoren wie [1,1 '-Bis (diphenylphosphino)ferrocen]dichlorpalladium (II) oder Tetrakis(triphenylphosphin) palladium in Betracht. Als geeignete basische Reaktionshilfsmittel zur Durchführung der Verfahren gemäss Reaktionsschema III finden bevorzugt Carbonate des Natriums oder Kaliums Verwendung. Examples of suitable coupling catalysts are palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) or tetrakis (triphenylphosphine) palladium. Suitable basic reaction auxiliaries for carrying out the processes according to Reaction Scheme III are preferably carbonates of sodium or potassium.
Bevorzugt werden Nitrile wie Acetonitril, Benzonitril, insbesondere Acetonitril, oder Ether wie Diethylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan, insbesondere 1 ,2-Dimethoxyethan in Kombination mit Wasser eingesetzt. Die anschließende Oxidation des Schwefels in den Verbindungen der Formel (I-D-2) in denen W für Schwefel steht, führt zu Verbindungen der Formel (I-D-2) in denen W für SO oder SO2 steht (vgl. Reaktionsschema V) Preference is given to nitriles such as acetonitrile, benzonitrile, in particular acetonitrile, or ethers such as diethyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, in particular 1, 2-dimethoxyethane used in combination with water. The subsequent oxidation of the sulfur in the compounds of formula (ID-2) in which W is sulfur leads to compounds of formula (ID-2) in which W is SO or SO 2 (see Reaction Scheme V)
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 Lösungsbzw. 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®. Compounds of the formula (I) in which W is SO (sulfoxides) or SO 2 (sulfones) can be prepared by oxidation by methods known from the literature from compounds of the formula (I) in which W is S (thioethers), for example by an oxidizing agent in a suitable solution. Diluent. As an oxidizing agent, for example, dilute nitric acid, hydrogen peroxide, Oxone ® and peroxycarboxylic acids such as WEFA-chloroperbenzoic own. As solvents or diluents are inert organic solvent, typically acetonitrile, halogenated solvents such as dichloromethane, chloroform or dichloroethane, as well as water and alcohols such as methanol for reaction with Oxone ® suitable.
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 (TB HP), 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 (TB HP), 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).
Verbindungen der Formel (I), in denen R für -NR -CX-R steht, können beispielsweise aus Verbindungen der Formel (I), in denen R2 für -NHR23 steht, mittels N-Acylierungsreaktion unter Verwendung von aktivierten Verbindungen der Formel LG-CX-R22, worin LG für eine gegebenenfalls in-situ erzeugte nucleofuge Abgangsgruppe steht, erhalten werden. Compounds of formula (I) in which R is -NR -CX-R can be prepared, for example, from compounds of formula (I) in which R 2 is -NHR 23 by N-acylation reaction using activated compounds of formula LG-CX-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 Reaktionsschema VI 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 VI by known methods.
Reaktionsschema VI Reaction scheme VI
LG = Leaving group, z. B. Halogen  LG = Leaving group, z. B. halogen
DPPA = Diphenylphosphorylazid  DPPA = diphenylphosphoryl azide
Beispielsweise können Verbindungen der Formel (I-f) mittels Curtius Abbau, wie beispielsweise in Houben-Weyl, Methoden der Organischen Chemie, Band XI/1 (Georg Thieme Verlag Stuttgart), S. 865 beschrieben, erhalten werden. For example, compounds of the formula (I-f) can be obtained by Curtius degradation, as described, for example, in Houben-Weyl, Methoden der Organischen Chemie, Volume XI / 1 (Georg Thieme Verlag Stuttgart), page 865.
Hierbei können die Verbindungen der Formel (I-b) beispielweise mit Diphenylphosphorylazid (DPPA) in Gegenwart von tert-Butanol direkt zu Verbindungen der Formel (I-f) reagieren. Here, the compounds of the formula (I-b) can react, for example, with diphenylphosphoryl azide (DPPA) in the presence of tert-butanol directly to compounds of the formula (I-f).
Aus den Verbindungen der Formel (I-f) lassen sich die Verbindungen der Formeln (I-g) 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. Die Verbindungen der Formel (I-h) können mittels N-Deblockierung (d.h. Abspaltung der Boc-Gruppe) in einem ersten Reaktionsschritt und nachfolgender N-Acylierung in einem zweiten Reaktionsschritt hergestellt werden. From the compounds of the formula (If), the compounds of the formulas (Ig) 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 (Ih) 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.
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. 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 protecting group (Boc group), for example, mixtures of mineral acids such as hydrochloric, hydrobromic, nitric, sulfuric, phosphoric or organic acids such as benzoic, formic, acetic, trifluoroacetic, methanesulfonic, benzenesulfonic or toluenesulfonic 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.
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 Stereoisomere als auch beliebige Gemische dieser Isomere. Verfahren und Verwendungen 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. 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. 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.
Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. 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 formula (I) are suitable with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, to improve crop yields Quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and mollusks, used in agriculture, horticulture, livestock, aquaculture, forests, gardens and recreational facilities, in the protection of stored products and materials, and occur in the hygiene sector. 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 coffeae, 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, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., z.B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; aus der Ordnung der Coleoptera z.B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, 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., Epicaerus 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, Listronotus (= Hyperodes) spp., 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., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z.B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., z.B. Oulema melanopus, Oulema oryzae, 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, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Sinoxylon perforans, 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 Dermaptera z.B. Anisolabis maritime, Forficula auricularia, Labidura riparia; 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., Euleia heraclei, 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, Platyparea poeciloptera, 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, Toxotrypana curvicauda; 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., Aleurocanthus 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, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, 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 chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., z.B. Dysaphis apiifolia, Dysaphis plantagmea, 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., Fiorinia spp., Furcaspis oceanica, 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, Lopholeucaspis japonica, 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, Neomaskellia spp., Nephotettix spp., z.B. Nephotettix cinetieeps,, Nephotettix nigropictus, Nettigoniclla spectra, 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, Perkinsiella spp., 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., Pulvinaria 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 rufiabdominale, Saissetia spp., z.B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella fureifera, 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. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z.B. Cimex adjunetus, 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, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z.B. Lygocoris pabulmus, Lygus spp., z.B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., z.B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, 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., Camponotus spp., Dolichovespula spp., Diprion spp., z.B. Diprion similis, Hoplocampa spp., z.B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., z.B. Vespa crabro, Wasmannia auropunctata, 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., Kalotermes spp., Microtermes obesi, Nasutitermes spp., 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., Autographa spp., Barathra brassicae, Blastodacna atra, 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, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, 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., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., z.B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima 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, Lampides spp., Laphygma spp., Laspeyresia molesta, 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. Lyman ria 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., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., z.B. Ostrinia nubilalis, 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., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., 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, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., z.B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., 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; 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.; Tier- und Humanparasiten aus den Stämmen der Platyhelminthes und Nematoda, z.B. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, z.B. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., z. B. Brugia malayi, Brugia timori, Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., z. B. Dictyocaulus filaria, Diphyllobothrium spp., z. B. Diphyllobothrium latum, Dipylidium spp., Dirofilaria spp., Dracunculus spp., z. B. Dracunculus medinensis, Echinococcus spp., z.B. Echinococcus granulosus, Echinococcus multilocularis, Echinostoma spp., Enterobius spp., z.B. Enterobius vermicularis, Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp., z.B. Hymenolepis nana, Hyostrongylus spp., Litomosoides spp., Loa spp., z.B. Loa Loa, Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, z.B. Onchocerca volvulus, 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., z.B. Strongyloides fuelleborni, Strongyloides stercoralis, Strongylus spp., Syngamus spp., Taenia spp., z.B. Taenia saginata, Taenia solium, Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., z.B. Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., z.B. Trichuris trichuria, Uncinaria spp., Wuchereria spp., z.B. Wuchereria bancrofti; 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 coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangi ferus, 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, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., eg Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of the Coleoptera eg Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, 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 spp., 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., Epicaerus 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, Listronotus (= Hyperodes) spp., Lixus spp., Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., Eg Melanotus longulus or egonensis, Meligethes aeneus, Melolontha spp., eg Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., eg Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., eg Oulema melanopus, Oulema oryzae, 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, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp., eg Sitophilus granarius, Sitophilus linearis, Si tophilus 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 Dermaptera eg Anisolabis maritime, Forficula auricularia, Labidura riparia; 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 s pp., eg, Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, 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, Platyparea poeciloptera, 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 s mplex, Toxotrypana curvicauda; 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., Aleurocanthus 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 brassi cae, Cacopsylla spp., eg Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chrysophis juglandicola, Chrysomphalus aonidum, 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 chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., Eg Dysaphis apiifolia, Dysaphis plantagmea, 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., Fiorinia spp., Furcaspis oceanica, 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, Lopholeucaspis japonica, 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, Neomaskellia spp., Nephotettix spp., Eg Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, 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, Perkinsiella spp., 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., Pulvinaria spp., Pyrilla spp., Quadraspidiotu ssp., eg Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., eg Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., eg Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella fureifera, 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 Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., eg Cimex adjunetus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eg Eushtistus heros, Euschistus servus, Eustistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocoris varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., Eg Lygocoris pabulmus, Lygus spp., Eg Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria , Miridae, Monaionion atratum, Nezara spp., Eg Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Eg Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera eg Acromyrmex spp., Athalia spp., eg Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., eg Diprion similis, Hoplocampa spp., eg Hoplocampa cookei, Hoplocampa testudinea, Lasius Spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., eg Vespa crabro, Wasmannia auropunctata, 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., Kalotermes spp., Microtermes obesi, Nasutitermes spp., 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., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Eg Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodixis chalcites, 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., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Egg dana saccharina, Ephestia spp., eg, Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., eg Euproctis chrysorrhoea , Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., Eg Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Eg Helicoverpa armigera, Helicoverpa zea, Heliothis spp., Eg Heliothis virescens, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., Eg Leucoptera coffeella, Lithocolletis spp., Eg Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Eg Lobesia botrana, Loxagrotis albicosta, Lymantria spp., Eg Lyman ria dispar, Lyonsetia spp., Eg Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., Eg Ostrinia nubilalis, 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 bipunctif he, Scirpophaga spp., eg Scirpophaga innotata, Scotia segetum, Sesamia spp., eg Sesamia inferens, Sparganothis spp., Spodoptera spp., eg Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp. Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., 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, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., eg Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp , Hercinothrips femoralis, Kakothrips spp., 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; Pests from the strain of Mollusca, in particular from the class of bivalvia, for example Dreissena spp .; and from the class of Gastropoda eg Arion spp., eg Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., eg Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp . Animal and human parasites from the strains of Platyhelminthes and Nematoda, eg Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, eg Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp. Ascaridia spp., Baylisascaris spp., Brugia spp., E.g. Brugia malayi, Brugia timori, Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., E.g. B. Dictyocaulus filaria, Diphyllobothrium spp., Z. Diphyllobothrium latum, Dipylidium spp., Dirofilaria spp., Dracunculus spp., E.g. B. Dracunculus medinensis, Echinococcus spp., Eg Echinococcus granulosus, Echinococcus multilocularis, Echinostoma spp., Enterobius spp., Eg Enterobius vermicularis, Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp , Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Eg Hymenolepis nana, Hyostrongylus spp., Litomosoides spp., Loa spp., Eg Loa Loa, Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, eg, Onchocerca volvulus, 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., Stephanus spp., Strongyloi eg Sp., Strongyloides fuelleborni, Strongyloides stercoralis, Strongylus spp., Syngamus spp., Taenia spp., eg Taenia saginata, Taenia solium, Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp. eg Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., eg Trichuris trichuria, Uncinaria spp., Wuchereria spp., eg Wuchereria bancrofti;
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 ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., z.B. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., z.B. Ditylenchus dipsaci, Dolichodorus 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, Hirschmanieila spp., 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., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., z.B. Paratrichodorus minor, Paratylenchus spp., 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. 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 ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., Eg Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., Eg Ditylenchus dipsaci, Dolichodorus 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, Hirschmanieila spp., Hoplolaimus spp., Longidorus spp., Eg Longidorus africanus, Meloidogyne spp., Eg Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita , Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., Eg Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., Eg Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., eg Radopholus citrophilus, 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.
Weiterhin lässt sich aus dem Unterreich der Protozoa die Ordnung der Coccidia z.B. Eimeria spp. bekämpfen. Furthermore, from the sub-kingdom of protozoa, the order of coccidia can be determined, e.g. Eimeria spp. 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 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. Formulations The present invention furthermore relates to formulations and use forms prepared therefrom as pesticides, such as, for example, pesticides. 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. For example, vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g. organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-demanding agents such. Dioctylsulfosuccinate or hydroxypropyl-guar polymers and / or humectants, e.g. Glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
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 Specifications, 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. 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. 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 Specifications, 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. 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. 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 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, chloroethylenes 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. In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such as cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as methanol, ethanol, Isopropanol, 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 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 alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, 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 auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, such as iron oxide, titanium oxide, Ferrocyanblau and organic Dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
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. 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.
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. 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.
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. 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 Betracht, 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. Suitable penetration promoters in the present context are 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 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. 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 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.
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. 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. 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. 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. 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 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.
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. 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,(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 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. Ethofenofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamates, trimethacarb, XMC and xylylcarb or organophosphates, e.g. 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. (3) Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker, wie beispielsweise Pyrethroide, z.B. 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, Momfluorothrin, 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. (2) GABA-controlled chloride channel antagonists, such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil. (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 isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, Flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, 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, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
(5) Nikotinerge Acetylcholin-Rezeptor (nAChR) allosterische Aktivatoren, wie beispiel Spinosine, z.B. Spinetoram und Spinosad. (6) Chlorid-Kanal-Aktivatoren, wie beispielsweise Avermectine/Milbemycine, z.B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (5) nicotinergic acetylcholine receptor (nAChR) allosteric activators, such as spinosines, eg spinetoram and spinosad. (6) Chloride channel activators, such as avermectins / milbemycins, eg, 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) Anti-skinning agents (especially in dipterans, i.e., two-toed), 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). (22) Spannungsabhängige Natriumkanal-Blocker, z.B. Indoxacarb oder Metaflumizone. (21) complex I electron transport inhibitors, for example, 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.
(23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z.B. Spirodiclofen, Spiromesifen und Spirotetramat. (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. (25) Komplex-II-Elektronentransportinhibitoren, wie beispielsweise Cyenopyrafen und Cyflumetofen. (24) complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide. (25) Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
(28) Ryanodinrezeptor-Effektoren, wie beispielsweise Diamide, z.B. Chlorantraniliprole, Cyantraniliprole und Flubendiamide. (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- (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-in-l -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 ausWO2003 / 106457), 2-chloro-N- [2- {1 - [(2E) -3- (4-chlorophenyl) prop-2-en-1-yl] piperidin-4-yl} -4- (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 US Pat WO2009 / 049851), 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1,8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from WO2009 / 049851), 4- (But-2-yn-1-yloxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004 / 099160), 4- (But-2-in-1 - yloxy) -6- (3-chlorophenyl) pyrimidine (known from WO2003 / 076415), PF1364 (CAS Reg. No. 1204776-60-2), methyl 2- [2 - ({[3-bromo-l-] (3-chloropyridin-2-yl) -1H-pyrazol-5-ylcarbonyl} amino) -5-chloro-3-methylbenzoyl] -2-methylhydrazinecarboxylate (known from
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 ausWO2005 / 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-chloropyridine-2-ol) yl) -lH-pyrazole-5-carboxamide (known from CN102057925), 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-dichloro-1-yl-yl) -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] pyridine-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 [l, 2-a] pyrimidin-l-ium-2-olate (known from
WO2009/099929), l-[(6-Chlo^yridin-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-methylphenyl] - 1 -(3 -chlorpyridin-2-yl)-3 -(fluormethoxy)- 1 H-pyrazol-5- 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-Dichlo^henyl)-5-(trifluormethyl)-4H soxazol-3-yl]-N-[(Z)-methoxyimino- methyl]-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 aus WO2012/000896), N-[3- (Benzylcarbamoyl)-4-chlorphenyl] - 1 -methyl-3-(pentafluorethyl)-4-(trifluormethyl)- 1 H-pyrazol-5- carboxamid bekannt aus WO2010/051926). WO2009 / 099929), l - [(6-chloro-3-yl-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidine-l-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-methylphenyl] -1- (3-chloropyridin-2-yl) -3- (fluoromethoxy) -1H pyrazole-5-carboxamide (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-ene 1-yl] carbonate (known from CN 102060818), 4- [5- (3,5-dichloro-1-yl-yl) -5- (trifluoromethyl) -4H-soxazol-3-yl] -N - [(Z) -methoxyimino - methyl] -2-methylbenzamide (known from WO2007 / 026965), 3E) -3- [1- (6-chloro-3-pyridyl) methyl] -2-pyridylidene] -1,3,1-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-chlorophenyl] -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5-carboxamide known from WO2010 / 051926).
Fungizide Die hier mit ihrem "common name" spezifizierten Wirkstoffe sind bekannt, beispielsweise beschrieben im "Pesticide Manual" oder im Internet (beispielsweise: http://www.alanwood.net/pesticides). Fungicides 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 füngiziden 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 of the listed five-component mixed partners of classes (1) to (15) can optionally form salts with corresponding bases or acids, provided that suitable functional groups are present. In addition, tautomeric forms are also included for the listed ficcidial mixed partners 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)- 2-(2,4-difluorphenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol-5-ylthiocyanat, (1.68) 5-(Allylsulfanyl)- 1 - {[3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} -lH-l,2,4-triazol, (1.69) 2-[l-(2,4- Dichlo^henyl)-5-hydroxy-2,6,6 rimethylheptan-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-difluo 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) Prochlorazole, (1.40) Propiconazole, (1.41) Prothioconazole, ( 1.42) 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) - 1 H-imidazole-5-carboxylic acid ~ Tnethylester, (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-difluorophenyl) oxiran-2-yl] methyl} -1 H -1,2,4-triazol-5-yl thiocyanate, (1.68) 5- (allylsulfanyl) -1 - {[3- (2-chlorophenyl ) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-l, 2,4-triazole, (1.69) 2- [1- (2,4-dichloro-1-yl-yl) -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-difluo
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- 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} -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-chlo^henyl)-2-(2,4-difluo^henyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol, (1.75) 5- (Allylsulfanyl)-l- {[rel(2R,3R)-3-(2-chlo^henyl)^ 2-yl] methyl} -LH-l, 2,4-triazol-5-yl-thiocyanate, (1.73) 1- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-) difluorophenyl) oxiran-2-yl] methyl} -1H-l, 2,4-triazol-5-yl thiocyanate, (1-74) 5- (allylsulfanyl) -1- [¢ [(2R, 3S) -3- ( 2-chloro-1-yl) -2- (2,4-difluoro-1-yl) -oxiran-2-yl] -methyl} -1H-l, 2,4-triazole, (1.75) 5- (allylsulfanyl) -l- [ rel (2R, 3R) -3- (2-chlo ^ henyl) ^
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-triazole, (1.76) 2 - [(2S, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H -l, 2,4-triazole-3-thione, (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- Dichlo^henyl)-5-hydroxy-2,6,6 rimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.80) 2- [(2S,4S,5R) -(2,4-Dichlo^henyl)-5-hydroxy-2,6,6 rimethylheptan-4-yl]-2,4-dihydro-3H ,2,4 ri4-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) - 1- (2,4-Dichloro-1-yl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.80 ) 2- [(2S, 4S, 5R) - (2,4-Dichloro-1-yl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H, 2.4 ri
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)-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-triazol-3-thion, (1.84) 2-[4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (1.85) 2-[4-(4-5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.84) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-l, 2,4-triazol-1-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-dichlor- phenoxy)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)-4-[(lS)-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] -l - (1H-l, 2,4-triazol-1-yl) butan-2-ol, (1.88) 2- [2-chloro-4- (2,4-dichloro) phenoxy) phenyl] -1- (1H-l, 2,4-triazol-1-yl) propan-2-ol, (1.89) (2R) -2- (1-chlorocyclopropyl) -4 - [(IR) - 2,2-dichlorocyclopropyl] -1- (1H-l, 2,4-triazol-1-yl) butan-2-ol, (1.90) (2R) -2- (1-chlorocyclopropyl) -4 - [(lS ) -
2.2- dichlorcyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (1.91) (2S)-2-( 1 -Chlorcyclopropyl)-4- [(lS)-2,2-dichlorcyclopropyl]-l-(lH-l,2,4-triazol-l-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) (l S,2R,5R)-5-(4- Chlorbenzyl)-2-(chlormethyl)-2-methyl- 1 -(1 H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol, (1.94)2,2-dichlorocyclopropyl] - 1 - (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.91) (2S) -2- (1-chlorocyclopropyl) -4- [(IS) -2,2-dichlorocyclopropyl] -1- (1H-l, 2,4-triazol-1-yl) butan-2-ol, (1.92) (2S) -2- (1-chlorocyclopropyl) -4 - [( lR) -2,2-dichlorocyclopropyl] -1- (1H-l, 2,4-triazol-1-yl) butan-2-ol, (1.93) (1S, 2R, 5R) -5- (4 Chlorobenzyl) -2- (chloromethyl) -2-methyl-1 - (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.94)
(lR,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-mem^^ (LR, 2S, 5S) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-mem ^^
(1.95) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl- 1 -( 1 H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol.  (1.95) 5- (4-Chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-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^ 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, 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-1,40
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- lH-pyrazol-4-carboxamid, (2.32) 3-methyl-1H-pyrazole-4-carboxamide, (2.31) N - [(1R, 4S) -9- (dichloromethylene) -1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.32) 3-
(Difluormethyl)- 1 -methyl-N-( 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 H-pyrazol-4-carboxamid, (2.33) 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-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4- 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-(Difluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.33) 1.3 , 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-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.36) 1-methyl-3 - (trifluoromethyl ) -N- [(3S) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.37) 3- (difluoromethyl ) - 1-methyl-N- [(3S) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.38) 3 (Difluoromethyl) -1-methyl-N - [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.39) 1, 3,5-trimethyl-N - [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.40) l , 3,5-trimethyl-N - [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.41) Benodanil, (2.42) 2-Chloro-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)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.46) N-(2',4'-Dichlorbiphenyl-2-yl)-3 - (difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.47) 3 -(Difluormethyl)- l-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)- l-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-trichlor- phenyl)propan-2-yl]-lH-pyrazol-4-carboxamid, (2.68) 3-(Difluormethyl)-N-(7-fluor-l,l,3-trimethyl- 2,3 -dihydro- 1 H-inden-4-yl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.69) 3 -(Difluormethyl)-N- [(3R)-7- fluor- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 -methyl- 1 H-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. 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 ] -LH-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 -l - in 1 -yl) biphenyl-2-yl] -1-H-pyrazole-4-carboxamide, (2.50) 5-fluoro-1,3-dimethyl-N- [4 '- (prop-1-in - 1 - yl) biphenyl-2-yl] -1H-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-l, 3-dimethyl-lH-pyrazol-4-carbo xamide, (2.56) 2-chloro-N- (4'-ethynyl-biphenyl-2-yl) nicotinamide, (2.57) 2-chloro-N- [4 '- (3,3-dimethylbut-1-yn-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-yl-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-yn-1-yl) biphenyl-2-yl] nicotinamide, (2.64) l, 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) -l, l, 3-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, 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) Dimoxystrobin, (3.08) Enoxastrobin, (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-fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methyl_,acetamid, (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- methylacetamid, (3.27) Fenaminostrobin, (3.28) 5-Methoxy-2-methyl-4-(2- {[( {(lE)-l-[3- (trifluormethyl)phenyl]ethyliden}amino)oxy]methyl}p (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-(4-3) 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) dimoxystrobin, (3.08) enoxastrobin , (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 -fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methyl_ , acetamide, (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- [({[(1 E) - 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- {[({(L (e) -l- [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} p (3.29) (2E) -2- {2 - [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyacrylic 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-
Chlorphenyl)-lH-pyrazol-3-yl]oxy} -2-(methoxyimino)-N,3-dimethylpent-3-enamid. Chlorophenyl) -1H-pyrazol-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-(2,4,6 rifluo^henyl)[l,2,4]triazolo[l,5-a]pyrimidin, (4.14) 3- Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin. 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- (2,4,6-trifluoro ^ henyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, (4.14) 3-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)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-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l- yl)chinolin, (7.09) Oxytetracyclin, (7.10) Streptomycin. 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. 11) Inhibitoren der Melaninbiosynthese, zum Beispiel (11.01) Carpropamid, (11.02) Diclocymet, (1 1.03) Fenoxanil, (11.04) Phthalid, (11.05) Pyroquilon, (1 1.06) Tricyclazol, (11.07) 2,2,2-Trifluorethyl {3-methyl-l-[(4-methylbenzoyl)amino]butan-2-yl}carbamat. 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) inhibitors of melanin biosynthesis, for example (11.01) carpropamide, (11.02) diclocymet, (1.03) fenoxanil, (11.04) phthalide, (11.05) pyroquilone, (1.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl {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. 14) Verbindungen, die als Entkoppler wirken können, zum Beispiel (14.01) Binapacryl, (14.02) Dinocap, (14.03) Ferimzon, (14.04) Fluazinam, (14.05) Meptyldinocap. 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) 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-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluormethyl)-lH-pyrazol-l- yl]ethanon, (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)-lH-pyrazol-l-yl]-l-(4- {4-[(5S)-5-phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3 hm^^ 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-fluorben- zyl)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-dichlornicotmamid, (15.080) N-[l -(5-Brom-3-chlorpyridin-2-yl)ethyl]-2-fluor-4-iodnicotinamid, (15.081) N- {(E)-[(Cyclopropyl- methoxy)imino] [6-(difluormethoxy)-2,3-difluorphenyl]methyl} -2-phenylacetamid, (15.082) N- {(Z)- [(Cyclopropylmethoxy)imino][6-(difluormethoxy)-2,3-difluo^henyl]methyl}-2-phenylacetami (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-(l- {[5-methyl-3-(trifluormethyl)-lH-pyrazol-l- yl] acetyl} piperidin-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)- 1 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-[( {[(1 -Methyl-1 H-tetrazol-5-yl)(phenyl)methylen]amino} oxy)me- thyl]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_,pyridin-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) Nickeldimethyldithiocarbamate, (15,035) Nitrothal isopropyl, (15,036) Oxamocarb, (15,037 ) Oxyfenthiine, (15.038) pentachlorophenol and salts, (15.039) phenothrin, (15.040) phosphorous acid and others n Salts, (15,041) propamocarb-fosetylate, (15,042) propanosine sodium, (15,043) pyrimorph, (15,044) pyrrole nitrite, (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) 1- (4- {4 - [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-l, 2-oxazol-3-yl] -l, 3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -lH- pyrazol-1-yl] ethanone, (15.053) 1- (4- {4 - [(5S) -5- (2,6-difluorophenyl) -4,5-dihydro-l, 2-oxazol-3-yl] -l, 3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (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-lH, 5H- [l, 4] dithiino [2,3-c: 5,6-c '] dipyrrolo, 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-l, 2-oxazol-3-yl] -l, 3-thiazol-2-yl} piperidin-1-yl) ethanone, (15.060) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazole -l-yl] -l- (4- {4 - [(5S) -5-phenyl-4,5-dihydro-1,2-oxazol-3-yl] -l, 3 hm ^^ yl} piperidine l -yl) ethanone, (15.061) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- {4- [4- (5-phenyl-4,5-dihydroxy) -4- l, 2-oxazol-3-yl) -1,3-thiazol-2-yl] piperidin-1-yl} ethanone, (15.062) 2-butoxy-6-iodo-3-propyl-4H-chromen-4- on, (15,063) 2-Chloro-5- [2-chloro-1- (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-l, 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] pyrimidine -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 Ethyl phenylacrylate, (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-dichloronotomamide, (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) -1H-pyrazol-1-yl] acetyl} piperidin-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) -1-H-pyrazol-1-yl] -acetyl} -piperidin-4-yl) -N- [ (1R) -l, 2,3,4-tetrahydronaphthalen-1-yl] -1,3-thiazole-4-carboxamide, (15,086) N -methyl-2- (1 - {[5-methyl-3 ( trifluoromethyl) -1 H -pyrazol-1-yl] acetyl} piperidin-4-yl) -N- [(1S) -1, 2,3, 4-tetrahydronaphthalene-1-yl] -1,3-thiazole-4 -carboxamide, (15.087) {6 - [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) -methylene] amino} oxy) -methyl] -pyridin-2-yl} , carbamoylpentene lester, (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 _ , pyridin-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)chinazolm, (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)chmolm, (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-methylim (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 -fluoropyrimidine-2 (1H) -one), (15,097) 3,4,5- Trihydroxybenzoic acid propyl ester, (15.098) [3- (4-Chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-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) -1,2-oxazol-4-yl] (pyridin-3-yl) -methanol, (15.101) 2- Fluoro-6- (trifluoromethyl) -N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -benzamide, (15.102) 2- (6-benzylpyridin-2-yl) quinazole m , (15.103) 2- [6- (3-Fluoro-4-methoxyphenyl) -5-methylpyridin-2-yl] quinazoline, (15.104) 3- (4,4-difluoro-3,3-dimethyl-3,4 (dihydroisoquinoline-1-yl) chmolm, (15.105) abscisic acid, (15.106) N '- [5-bromo-6- (2,3-dihydro-1H-inden-2-yloxy) -2-methyl-pyridin-3-yl ] -N-ethyl-N-methylimidoformamide, (15.107) N '- {5-bromo-6- [1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N -methylimidoformamide, (15.108) N '- {5-bromo-6 - [(1R) -1- (3,5-difluoroethylenedioxy] -2-methylpyridin-3-yl} -N-ethyl-N- methylim
(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- 1 -methyl- 1 H-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- 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- 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-carboxamid, (15.126) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4- carboxamid, (15.127) N-Cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-N-[5-methyl-2- (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) -1-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- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.116) N- (5-chloro-2-isopropylbenzyl) - N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.117) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) 5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (1 5.118) N-Cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -1-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-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 ) -l-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-carboxamide, (15.126) N- [5-chloro-2- (trifluoromethyl) benzyl] -N -cyclopropyl-3- (difluorme ethyl) -5-fluoro-1-methyl-1H-pyrazole-4-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)-! -methyl- lH-pyrazol-4-carbothioamid, (15.132) N'-(2,5-Dimethyl-4-phenoxyphenyl)- N-ethyl-N-methylimidoformamid, (15.133) Ν'- {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-methylchinolm-3-yl)oxy]-6-fluorphenyl}propan-2-ol, (15.138) 4-(2- Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-l,3-dimethyl-lH-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-lH-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- lH-pyrazol-5-amin, (15.148) 4-(2-Brom-4-fluorphenyl)-N-(2,6-difluorphenyl)-l,3-dimethyl-lH- 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-methylimido- formamid, (15.156) N'-(2,5-Dimethyl-4- {[3-(l ,l,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(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4- {5-[2-(prop-2-in-l-yloxy)phenyl]-4,5-dihydro-l,2- oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.161) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l- yl]-l-[4-(4- {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, (15.162) 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 -yljethanon, (15.163) 2- {3-[2-(l- {[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazoM 4,5-dihydro-l,2-oxazol-5-yl}phenylmethansulfonat, (15.164) 2- {3-[2-(l- {[3,5-Bis(difluormethyl)-lH- pyrazol-l-yl]_,acetyl}piperidm-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorphenyl- methansulfonat, (15.165) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4- {(5S)-5-[2-(prop-2-in-l- yloxy)phenyl]-4,5-dihydro-l ,2-oxazol-3-yl} -1 ,3-thiazol-2-yl)piperidin-l -yljethanon, (15.166) 2-[3,5- Bis(difluormethyl)- 1 H-pyrazol- 1 -yl] - 1 - [4-(4- {(5R)-5 - [2-(prop-2-in- 1 -yloxy)phenyl] -4,5-dihydro- 1,2- oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.167) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l- yl]-l-[4-(4- {(5S)-5-[2-fluor-6-(prop-2-in-l-yloxy)pte (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) -! -methyl-lH-pyrazole-4-carbothioamide, (15.132) N '- (2,5-dimethyl-4-phenoxyphenyl) - N-ethyl-N-methylimidoformamide, (15,133) Ν '- {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-pyrazol-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-2-methylquinolm-3-yl) oxy] -6-fluorophenyl} propane 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-pyrazol-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) -l , 3-dimethyl-1H-pyrazole-5-amine, (15.142) N- (2-bromo-6-fluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazole 5-amine, (15,143) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -l, 3-dimeth yl-1H-pyrazol-5-amine, (15.144) 4- (2-bromo-4-fluorophenyl) -N- (2-bromo-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-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, (15.1 54) 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-methylimidoformamide, (15.156) N '- (2,5-dimethyl-4- {3-l, l, 2, 2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.157) N '- (2,5-dimethyl-4- {[3- (2,2,2-trifluoroethoxy) phenyl] sul - fanyl} 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 (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {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, (15.161) 2- [3,5-bis (difluoromethyl) -lH- pyrazol-1-yl] -1- [4- (4- {5- [2-fluoro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazole 3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (1 5.162) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1 - [4- (4- {5- [2-chloro-6- (prop-2-in-1 - yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidine-1-yl-ylanone, (15.163) 2- {3- [2- ( 1- {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazoM 4,5-dihydro-1,2-oxazol-5-yl } phenylmethanesulfonate, (15.164) 2- {3- [2- (1 - {[3,5-Bis (difluoromethyl) -1H-pyrazol-1-yl] _, acetyl} piperidm-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-pyrazole 1-yl] -1- [4- (4- {(5S) -5- [2- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazole-3 -yl} -1, 3-thiazol-2-yl) piperidine-1-yl-ylanone, (15.166) 2- [3,5- Bis (difluoromethyl) -1 H -pyrazol-1-yl] -1- [4- (4-{(5R) -5 - [2- (prop-2-yn-1-ynyloxy) phenyl] -4.5 -dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.167) 2- [3,5-bis (difluoromethyl) -1H-pyrazole -l-yl] -l- [4- (4- {(5S) -5- [2-fluoro-6- (prop-2-yn-1-yloxy) pte
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- 1 -yloxy)phenyl]-4,5-dihydro-l ,2-oxazol-3-yl} -1 ,3-thiazol-2-yl)piperidin-l -yl]ethanon, (15.170) 2-[3,5- Bis(difluormethyl)- 1 H-pyrazol- 1 -yl] - 1 - [4-(4- {(5R)-5 - [2-chlor-6-(prop-2-in- 1 -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(difluormethyl)-l H-pyrazol- l-yl]acetyl}piperidm^ 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) piperidine-1 - yl] ethanone, (15.169) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {(5S) -5- [2-chloro-6 - (prop-2-yn-1-ynyloxy) phenyl] -4,5-dihydro-l, 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone (15.170) 2- [3,5-bis (difluoromethyl) -1 H -pyrazol-1-yl] -1- [4- (4-{(5R) -5 - [2-chloro-6 (propyl) 2-in-1-ylxy) phenyl] -4,5-dihydro-l, 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.171) 2 - {(5S) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidine
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- 1 ,2-oxazol-5-yl}phenylmethansulfonat, (15.173) 2- {(5S)-3-[2-(l- {[3,5-Bis(difluormethy^ 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-1,2-oxazol-5-yl-phenylmethanesulphonate, (15.173) 2- {(5S) -3- [2- (1 - {[3 , 5-bis (difluormethy ^
dihydro-1 ,2-oxazol-5-yl} -3-chlorphenylmethansulfonat, (15.174) 2- {(5R)-3-[2-(l - {[3,5- Bis(difluormethyl)-l H-pyrazol- l-yl]acetyl}piperidm^ dihydro-1,2-oxazol-5-yl} -3-chlorophenyl methanesulfonate, (15.174) 2- {(5R) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazole - l-yl] acetyl} piperidm ^
yl} -3-chlorphenylmethansulfonat. yl} -3-chlorophenylmethanesulfonate.
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 fumosorosea), 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: Examples of viruses that can be used or used as biological pesticides are:
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. 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.
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: 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: 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. 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, 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, Paprika und Chili, Gurken, Melonen, Karotten, Wassermelonen, Zwiebel, Salat, Spinat, Lauch, Bohnen, Brassica oleracea (z.B. Kohl), Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrasfrüchten 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 Pflanzen sollen alle Entwicklungsstadien der Pflanzen verstanden werden, beispielsweise Samen, Stecklinge sowie junge (unreife) Pflanzen bis hin zu reifen Pflanzen. 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 (geerntete Pflanzen oder Pflanzenteile) 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. Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Peppers and chillies, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (eg cabbage), peas and other vegetables, cotton, tobacco, oilseed rape, as well as 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. Plants are to be understood as meaning all stages of development of the plants, for example seeds, cuttings and young (immature) plants through to mature plants. 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 (harvested plants or plant parts) as well as vegetative and generative propagation material, for example 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, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. The treatment according to the invention of the plants and plant parts with the compounds of the formula (I) takes place directly or by acting on their environment, habitat or storage space according to the conventional treatment methods, for example by dipping, spraying, vaporizing, atomizing, spreading, brushing, injecting and propagating material, in particular in seeds, further by single or multi-layer wrapping.
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 (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische 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 Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. 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 varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering 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 drought or to bottoms salt, 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 harvested 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, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes ), with particular emphasis on corn, soy, wheat, rice, potato, cotton, sugarcane, 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. A preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched 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 may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i. the compounds of formula (I) are incorporated in solid form (e.g., in the form of granules) at the plant site. In water rice crops, this may also be by metered addition of the compound of formula (I) in a solid form (e.g., as granules) into a flooded paddy field.
Saatgutbehandlung 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. Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to 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 the protection of the seed and the germinating plant, which will increase the additional application of pesticides during storage make the sowing or after emergence of the plants redundant or at least significantly reduce. 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. 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.
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. 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. 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. 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.
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. One of the advantages that occurs when one of the compounds of formula (I) acts systemically is that the treatment of the seed not only the seed itself, but also the resulting Protects 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. Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt 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. 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. 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.
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. 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.
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. 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. 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. 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. These formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents 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 trimethylene glycols. Stryrylphenolpolyglykolether 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 ernndungsgemäß 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. 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. 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.
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. 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.
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). 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 Zu- bereitungen 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. 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. 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 maize, rice, rapeseed, peas, beans, cotton , Sunflower, soy and beet 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. 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. In detail, the procedure for pickling is to place the seed in a mixer in discontinuous or continuous operation, in each case the desired amount Mordant formulations added either as such or after prior dilution with water and mixed until uniform distribution of the formulation on 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 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. Animal health 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 veterinary field, the compounds of formula (I) which are of low toxicity to warm-blooded animals are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. 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 pets 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. 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. By using the compounds of formula (I) for the control of animal parasites disease, deaths and reductions in performance (in meat, milk, wool, hides, eggs, honey and the like) should be reduced or prevented, so that a more economical and easier animal husbandry allows and a better well-being of the animals is achievable. 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., Rhodnius 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., Rhodnius 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., Ornithodorus 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., Ornithodorus 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: 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; Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba histolytica, Hartmanellidae, zum Beispiel Acanthamoeba sp., Harmanella sp.; Parasitic protozoa include: Mastigophora (Flagellata), such as Trypanosomatidae, for example Trypanosoma b. brucei, Tb gambiense, Tb 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) such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example 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, 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. 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. 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., Especially C. parvum; such 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., Collyricum 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., S rongyloides spp.; aus der Ordnung Rhabditida zum Beispiel: S rongylus 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., Songyloides spp .; from the order Rhabditida, for example: S. rongylus 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. Thus, one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
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. 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.
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. 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 an antiectica, 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. 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).
Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: 1) Mücken - Anopheles: Malaria, Filariose; Examples of vectors and their transmitted diseases or pathogens are: 1) mosquitoes - 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; - Aedes: yellow fever, dengue fever, filariasis, other viral diseases;
- Simulien: Übertragung von Würmern insbesondere Onchocerca volvulus; - Simulia: transmission of worms, in particular Onchocerca volvulus;
2) Läuse: Hautinfektionen, Fleckfieber (epidemic typhus); 3) Flöhe: Pest, endemisches Fleckfieber; 4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 2) lice: skin infections, typhus (epidemic typhus); 3) Fleas: plague, endemic typhus fever; 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, e.g. 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 the formula (I) are present as ready-to-use pesticides, ie they can be applied to the appropriate material can be applied. 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, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins. 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. 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 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). 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). [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 from 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).
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. 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.
Allgemeine Synthese von 5-substituierten 2-(Hetaryl)-2H-pyrazolo[3,4-c]pyridinen der Formel (I); Beispiele 1 bis 38: General Synthesis of 5-Substituted 2- (Hetaryl) -2H-pyrazolo [3,4-c] pyridines of Formula (I); Examples 1 to 38:
Schritt 1: Step 1:
Synthese von Verbindungen der Formel (A-3) (R2 CO-OCH3) Synthesis of Compounds of Formula (A-3) (R 2 CO-OCH 3)
Zu einer Lösung von 28,3 mmol 2-substituiertem 5-Nitro-4-pyridincarboxaldehyd der Formel (A-l) in 200 mL Toluol wurden 1 Äquivalent einer heterocyclischen Aminoverbindung (A-2), 0,12 Äquivalent (3,4 mmol) /jara-Toluolsulfonsäure (PTSA) und 6 g 4A Molsieb gegeben. Anschließend wurde das Reaktionsgemisch 16 Stunden bei 110 °C gerührt. Das Reaktionsgemisch wurde filtriert und das Filtrat ergab nach dem Einengen die Rohprodukte (A-3), die ohne weitere Reinigung weiter umgesetzt wurden. To a solution of 28.3 mmol 2-substituted-5-nitro-4-pyridinecarboxaldehyde of formula (Al) in 200 mL toluene was added 1 equivalent of a heterocyclic amino compound (A-2), 0.12 equivalent (3.4 mmol) / jara toluenesulfonic acid (PTSA) and 6 g of 4A molecular sieve. Subsequently, the reaction mixture was stirred at 110 ° C for 16 hours. The reaction mixture was filtered and the filtrate gave after concentration the crude products (A-3), which were reacted further without further purification.
Schritt 2 step 2
Synthese von 5-substituierten 2-(Hetaryl)-2H-pyrazolo[3,4-c]pyridinen der Formel (I) Synthesis of 5-substituted 2- (hetaryl) -2H-pyrazolo [3,4-c] pyridines of the formula (I)
1 Äquivalent der Verbindungen der Formel (A-3) wurde in 30 mL Triethylphosphit gelöst und anschließend das Reaktionsgemisch ca. 16 Stunden bei 140 °C gerührt. Nach dem Einengen des Reaktionsgemisches im Vakuum wurde der verbleibende Rückstand mittels Säulenchromatographie gereinigt. 1 equivalent of the compounds of the formula (A-3) was dissolved in 30 ml of triethyl phosphite and then the reaction mixture was stirred at 140 ° C. for about 16 hours. After concentration of the reaction mixture in vacuo, the remaining residue was purified by column chromatography.
Allgemeine Synthese von 5-substituierten 2-(Hetaryl)-2H-pyrazolo[3,4-c]pyridin-5-carbonsäuren der Formel (I, R2 = COOH) General Synthesis of 5-substituted 2- (hetaryl) -2H-pyrazolo [3,4-c] pyridine-5-carboxylic acids of the formula (I, R 2 = COOH)
1 Äquivalent einer Verbindungen der Formel (I; R2 = COOCH3) wurde in einem Gemisch aus 100 ml Wasser und 100 ml Tetrahydrofuran gelöst und mit 3 Äquivalenten Lithiumhydoxid- monohydrat versezt. Anschließend wurde das Reaktionsgemisch ca. 16 Stunden bei 25 °C gerührt. Danach wurde das Tetrahydrofuran im Vakuum entfernt und die wässrige Phase mit IM Salzsäure auf den pH- Wert = 2 eingestellt. Nach Extraktion mit 100 mL Essigsäureethylester wurde die organische Phase über Natriumsulfat getrocknet, filtriert und im Vakuum eingeengt. Das verbleibende Rohprodukt wurde ohne weitere Aufarbeitung für den nächsten Reaktionsschritt eingesetzt. a) 2-(lH-7-Azabenzotriazol-l-yl)-l,l,3,3-tetramethyl-uronium-hexafluorophosphate- methanaminium (HATU)-Kupplungsmethode: 1 equivalent of a compound of the formula (I; R 2 = COOCH 3) was dissolved in a mixture of 100 ml of water and 100 ml of tetrahydrofuran and impregnated with 3 equivalents of lithium hydroxide monohydrate. Subsequently, the reaction mixture was stirred for about 16 hours at 25 ° C. Thereafter, the tetrahydrofuran was removed in vacuo and the aqueous phase adjusted to pH = 2 with 1M hydrochloric acid. After extraction with 100 ml of ethyl acetate, the organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The remaining crude product was used without further workup for the next reaction step. a) 2- (1H-7-Azabenzotriazol-1-yl) -l, l, 3,3-tetramethyl-uronium-hexafluorophosphate-methanaminium (HATU) Coupling Method:
1,0 Äquivalent 5-substituierte 2-(Hetaryl)-2H-pyrazolo[3,4-c]pyridin-5-carbonsäure wurde in 3 ml NN- Dimethylformaldehyd gelöst und mit 2,4 Äquivalenten (1,2 mmol) HATU und 6,0 Äquivalenten NN- Diisopropylethylamin versetzt. Danach wurde das Reaktionsgemisch 10 Minuten bei Raumtemperatur gerührt und anschließend mit 1,2 Äquivalenten der Sulfonamidkomponente versetzt. Nach ca. 16- stündigem Rühren bei Raumtemperatur wurde das Reaktionsgemisch im Vakuum eingeengt und der verbleibende Rückstands mittels präparativer Chromatographie (HPLC) gereinigt. b) 2-(lH-7-Azabenzotriazol-l-yl)-l,l,3,3-tetramethyl-uronium-hexafluorophosphate- methanaminium (HATU)-Kupplungsmethode: 1,0 Äquivalent 5-substituierte 2-(Hetaryl)-2H-pyrazolo[3,4-c]pyridin-5-carbonsäure wurde in 3 ml NN- Dimethylformaldehyd gelöst und mit 2,4 Äquivalenten (1,2 mmol) HATU und 2,4 Äquivalenten NN- Diisopropylethylamin versetzt. Danach wurde das Reaktionsgemisch 10 Minuten bei Raumtemperatur gerührt und anschließend mit 1,2 Äquivalenten der Aminkomponente versetzt. Nach ca. 16-stündigem Rühren bei Raumtemperatur wurde das Reaktionsgemisch im Vakuum eingeengt und der verbleibende Rückstands mittels präparativer Chromatographie (HPLC) gereinigt. 1.0 equivalent of 5-substituted 2- (hetaryl) -2H-pyrazolo [3,4-c] pyridine-5-carboxylic acid was dissolved in 3 ml of N, N-dimethylformaldehyde and treated with 2.4 equivalents (1.2 mmol) of HATU and 6.0 equivalents of N, N-diisopropylethylamine were added. Thereafter, the reaction mixture was stirred for 10 minutes at room temperature, followed by addition of 1.2 equivalents of the sulfonamide component. After about 16 hours of stirring at room temperature, the reaction mixture was concentrated in vacuo and the remaining residue purified by preparative chromatography (HPLC). b) 2- (1H-7-Azabenzotriazol-1-yl) -l, 1,3,3-tetramethyl-uronium-hexafluorophosphate-methanaminium (HATU) Coupling Method: 1.0 equivalent of 5-substituted 2- (hetaryl) -2H-pyrazolo [3,4-c] pyridine-5-carboxylic acid was dissolved in 3 ml of N, N-dimethylformaldehyde and treated with 2.4 equivalents (1.2 mmol) of HATU and 2.4 equivalents of N, N-diisopropylethylamine were added. Thereafter, the reaction mixture was stirred for 10 minutes at room temperature and then treated with 1.2 equivalents of the amine component. After about 16 hours of stirring at room temperature, the reaction mixture was concentrated in vacuo and the remaining residue purified by preparative chromatography (HPLC).
Synthese von Zwischenprodukten Synthesis of intermediates
4-|( l/; )-2 DinH'thylamiru))ethenyl)-5-nitro-2-pyridinecarbonsäurernethy  4- | (l /;) -2 DinH'thylamiru)) ethenyl) -5-nitro-2-pyridinecarboxylic acid methyl
Zu einer Lösung aus 65 g (0,33 mol) 5-Methyl-6-nitro-3-pyridincarbonsäuremethylester (Y. Morisawa et al., J. Med. Chem. 21, 194-199, 1978) in 415 mL NN-Dimethylformamid wurden 86.4 g, (0.73 mmol) NN-Dimethylformamid-0, 0-dimethylacetal gegeben. Danach wurde das Reaktionsgemisch 6 Stunden bei 90 °C gerührt. Anschließend wurde das Lösungsmittel im Vakuum entfernt und der verbleibende Rückstand wurde mittels Säulenchromatographie gereinigt. Man erhielt 56 g (Ausbeute 66,7 % d. Theorie) 4-[(l Z^-2-(Dimethylamino)ethenyl]-5-nitro-2-pyridincarbonsäuremethylester. To a solution of 65 g (0.33 mol) of methyl 5-methyl-6-nitro-3-pyridinecarboxylate (Y. Morisawa et al., J.Med.Chem. 21, 194-199, 1978) in 415 ml of NN- Dimethylformamide was charged with 86.4 g (0.73 mmol) of N, N-dimethylformamide 0, 0-dimethylacetal. Thereafter, the reaction mixture was stirred at 90 ° C for 6 hours. Subsequently, the solvent was removed in vacuo and the remaining residue was purified by column chromatography. This gave 56 g (yield 66.7% of theory) of methyl 4 - [(1-Z, -2- (dimethylamino) ethenyl] -5-nitro-2-pyridinecarboxylate.
4-Formyl-5-nitro-2-pyridinecarbonsäuremethyIester 4-formyl-5-nitro-2-pyridinecarbonsäuremethyIester
Zu einer Lösung von 56 g (0.22 mol) 4- [(1 £)-2-(Dimethylamino)ethenyl] -5-nitro-2- pyridincarbonsäuremethylester in 550 mL Wasser und 550 ml Tetrahydrofuran wurden 142 g (41.98 mmol) Natriumperiodat gegeben. Danach wurde das Reaktionsgemisch 16 Stunden bei 25 °C gerührt. Anschließend wurde das Reaktionsgemisch mit 700 mL Essigsäureethylester verdünnt und danach mit gesättigter wässriger Natriumhydrogencarbonat-Lösung und Salzlösung gewaschen. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und im Vakuum eingeengt. Der verbleibende Rückstand wurde mittels Säulenchromatographie gereinigt. Man erhielt 45 g (Ausbeute 97,3 % d. Theorie) 4-Fonnyl-5-nitro-2-pyridincarbonsäuremetliylester als braunen Feststoff. To a solution of 56 g (0.22 mol) of 4- [(1 L) -2- (dimethylamino) -ethenyl] -5-nitro-2-pyridinecarboxylic acid methyl ester in 550 mL of water and 550 mL of tetrahydrofuran was added 142 g (41.98 mmol) of sodium periodate , Thereafter, the reaction mixture was stirred at 25 ° C for 16 hours. Subsequently, the reaction mixture was diluted with 700 ml of ethyl acetate and then washed with saturated aqueous sodium bicarbonate solution and brine. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. Of the remaining residue was purified by column chromatography. This gave 45 g (yield 97.3% of theory) of 4-formyl-5-nitro-2-pyridinecarboxylic acid methyl ester as a brown solid.
Tabelle 1  Table 1
Verbindungen der Formel Compounds of the formula
*) kristallisiert mit 1 x HCOOH *) crystallizes with 1 x HCOOH
Tabelle 2 Table 2
Analytische Daten zu den Verbindung Analytical data on the compound
Bsp.-Nr. Retentionszeit [min] Ή-NMR [δ (ppm)] bzw. LC-MS [m/z] Expl Retention time [min] Ή-NMR [δ (ppm)] or LC-MS [m / z]
1 2,922 1H-NMR(400,0 MHz, dö-DMSO): δ = 1,65 (t, 3H, 1 2.922 1 H-NMR (400.0 MHz, dö-DMSO): δ = 1.65 (t, 3H,
CH3); 3,85 (m, 2H, CH2); 8,57; 8,78; 8,90; 8,96; 9,44; 9,58 (6H, =CH, Aryl/ Hetaryl). CH 3 ); 3.85 (m, 2H, CH 2 ); 8.57; 8.78; 8.90; 8.96; 9.44; 9.58 (6H, = CH, aryl / hetaryl).
LC-MS = 319.1 (M+l) [ohne HCOOH] Bsp.-Nr. Retentionszeit [min] Ή-NMR [δ (ppm)] bzw. LC-MS [m/z]LC-MS = 319.1 (M + 1) [without HCOOH] Expl Retention time [min] Ή-NMR [δ (ppm)] or LC-MS [m / z]
2 2,553 1H-NMR(400,0 MHz, dö-DMSO): δ = 1,24 (d, 6H, 2 2.553 1 H-NMR (400.0 MHz, dö-DMSO): δ = 1.24 (d, 6H,
2xCH3); 4,17 (m, 1H, CH); 8,43; 8,51 ; 8,77; 8,88; 9,39; 9,56 (6H, =CH, Aryl/Hetaryl). 2xCH 3 ); 4.17 (m, 1H, CH); 8.43; 8.51; 8.77; 8.88; 9.39; 9.56 (6H, = CH, aryl / hetaryl).
LC-MS = 283,2 (M+l); [ohne HCOOH]  LC-MS = 283.2 (M + 1); [without HCOOH]
3 2,843 1H-NMR(400,0 MHz, de-DMSO): δ = 3,78; 6,20 (2m, 3 2,843 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.78; 6,20 (2m,
3H, CH2CHF2); 8,51 ; 8,61 ; 8,80; 9,31 ; 9,40; 9.57 (6H, =CH, Aryl/Hetaryl); 9,05 (br., 1H, NH).  3H, CH 2 CHF 2); 8.51; 8.61; 8.80; 9,31; 9.40; 9.57 (6H, = CH, aryl / hetaryl); 9.05 (br., 1H, NH).
LC-MS = 322,1 (M+l); [ohne HCOOH]  LC-MS = 322.1 (M + 1); [without HCOOH]
4 2,141 1H-NMR(400,0 MHz, de-DMSO): δ = 1,15-1,26 (t+ m, 4 2.141 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.15-1.26 (t + m,
5H, CH2CH3); 8,43; 9,37; 9,57; 9,60 (4H, =CH, Aryl/Hetaryl); 8,80 (br., 1H, NH).  5H, CH 2 CH 3); 8.43; 9.37; 9.57; 9.60 (4H, = CH, aryl / hetaryl); 8.80 (br., 1H, NH).
LC-MS = 269,1 (M+l) [ohne HCOOH]  LC-MS = 269.1 (M + 1) [without HCOOH]
5 2,474 1H-NMR(400,0 MHz, de-DMSO): δ = 3,76; 6,20 (2m, 5 2.474 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.76; 6,20 (2m,
3H, CH2CHF2); 8,48; 8,56; 8,77; 8,89; 9,42; 9.57 (6H, =CH, Aryl/Hetaryl); 9,05 (br., 1H, NH).  3H, CH 2 CHF 2); 8.48; 8.56; 8.77; 8.89; 9.42; 9.57 (6H, = CH, aryl / hetaryl); 9.05 (br., 1H, NH).
LC-MS = 305.1 (M+l) [ohne HCOOH]  LC-MS = 305.1 (M + 1) [without HCOOH]
6 2,339 1H-NMR(400,0 MHz, CDCI3): δ = 1,66 (t, 3H, CH3); 6 2.339 1 H-NMR (400.0 MHz, CDCl 3): δ = 1.66 (t, 3H, CH 3 );
3,84 (m, 2H, CH2); 8,55; 9,37; 9,43; 9,60 (4H, =CH, Aryl/ Hetaryl); 8,96 (br., 1H, NH). 3.84 (m, 2H, CH 2 ); 8.55; 9.37; 9.43; 9.60 (4H, = CH, aryl / hetaryl); 8.96 (br., 1H, NH).
LC-MS = 319,0 (M+l) [ohne HCOOH]  LC-MS = 319.0 (M + 1) [without HCOOH]
7 1,889 1H-NMR(400,0 MHz, de-DMSO): δ = 3,01 ; 3,04 (2s, 7 1.889 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.01; 3.04 (2s,
6H, 2xCH3); 7,72; 8,01 ; 8,57; 8,75; 9,34; 9.38; 9,41 (7H, =CH, Aryl/ Hetaryl). 6H, 2xCH 3 ); 7.72; 8.01; 8.57; 8.75; 9.34; 9:38; 9.41 (7H, = CH, aryl / hetaryl).
LC-MS = 268,0 (M+l) [ohne HCOOH]  LC-MS = 268.0 (M + 1) [without HCOOH]
8 2,237 1H-NMR(400,0 MHz, de-DMSO): δ = 3,42 (s, 3H, CH3; 8 2.237 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.42 (s, 3H, CH 3;
8,65; 8,82; 9,33; 9,43; 9,64 (5H, =CH, Aryl/ Hetaryl). 8.65; 8.82; 9.33; 9.43; 9.64 (5H, = CH, aryl / hetaryl).
LC-MS = 335,9 (M+l) [ohne HCOOH] LC-MS = 335.9 (M + 1) [without HCOOH]
9 3,125 1H-NMR(400,0 MHz, de-DMSO): δ = 1,16 (t, 3H, 9 3.125 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.16 (t, 3H,
CH3); 3,37 (m, 2H, CH2); 3,95 (s, 3H, CH3); 3,57 (2s 6H, 2xCH3); 8,17; 8,41 ; 8,54; 9,11 ; 9.23 (5H, =CH, Aryl/ Hetaryl). CH 3 ); 3.37 (m, 2H, CH 2 ); 3.95 (s, 3H, CH 3); 3.57 (2s 6H, 2xCH 3 ); 8.17; 8.41; 8.54; 9.11; 9.23 (5H, = CH, aryl / hetaryl).
LC-MS = 271,1 (M+l) [ohne HCOOH]  LC-MS = 271.1 (M + 1) [without HCOOH]
10 2,575 1H-NMR(400,0 MHz, de-DMSO): δ = 2,93 (s, 6H, 10 2.575 1 H-NMR (400.0 MHz, de-DMSO): δ = 2.93 (s, 6H,
2xCH3); 8,62; 8,65; 8,82; 9,32; 9,42; 9.64 (6H, =CH, Aryl/ Hetaryl). 2xCH 3 ); 8.62; 8.65; 8.82; 9.32; 9.42; 9.64 (6H, = CH, aryl / hetaryl).
LC-MS = 365,1 (M+l) [ohne HCOOH]  LC-MS = 365.1 (M + 1) [without HCOOH]
11 2,138 1H-NMR(400,0 MHz, de-DMSO): δ = 3,32; 3,72 (2s 6H, 11 2.138 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.32; 3.72 (2s 6H,
2xCH3); 7,73; 8,10; 8,57; 9,46 (4H, =CH, Aryl/ Hetaryl).2xCH 3 ); 7.73; 8.10; 8.57; 9.46 (4H, = CH, aryl / hetaryl).
LC-MS = 284,1 (M+l); 283.28 (berechnet) LC-MS = 284.1 (M + 1); 283.28 (calculated)
12 2,409 1H-NMR(400,0 MHz, de-DMSO): δ = 1,16 (t 3H, CH3); 12 2.409 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.16 (t 3H, CH 3 );
3,37 (m, 2H, CH2); 8,45; 8,61; 8,80; 9,31; 9,36; 9,55 (6H, =CH, Aryl/ Hetaryl).  3.37 (m, 2H, CH 2); 8.45; 8.61; 8.80; 9.31; 9.36; 9.55 (6H, = CH, aryl / hetaryl).
LC-MS = 286,0 (M+l) 285.27 (berechnet)  LC-MS = 286.0 (M + 1) 285.27 (calculated)
13 2,592 1H-NMR(400,0 MHz, de-DMSO): δ = 0,71 (m 4H, 13 2.592 1 H-NMR (400.0 MHz, de-DMSO): δ = 0.71 (m 4H,
CH2CH2); 8,51 ; 8,77; 8,88; 9,37; 9,55; 9,58 (6H, =CH, Bsp.-Nr. Retentionszeit [min] Ή-NMR [δ (ppm)] bzw. LC-MS [m/z] CH2CH2); 8.51; 8.77; 8.88; 9.37; 9.55; 9.58 (6H, = CH, Expl Retention time [min] Ή-NMR [δ (ppm)] or LC-MS [m / z]
Aryl/ Hetaryl).  Aryl / hetaryl).
LC-MS = 281,0 (M+l) 280.28 (berechnet)  LC-MS = 281.0 (M + 1) 280.28 (calculated)
14 1,963 'H-NMR^OO^ MHZ, de-DMSO): δ = 2,86 (d, 3H,  14 1,963 'H NMR ^ OO ^ MHZ, de-DMSO): δ = 2.86 (d, 3H,
CH3); 8,50; 8,77; 8,88; 9,39; 9,56 (5H, =CH, Aryl/ Hetaryl). CH 3 ); 8.50; 8.77; 8.88; 9.39; 9.56 (5H, = CH, aryl / hetaryl).
LC-MS = 255.0 (M+l) 254.24 (berechnet)  LC-MS = 255.0 (M + 1) 254.24 (calculated)
15 2,044 1H-NMR(400,0 MHz, de-DMSO): δ = 3,03 (d, 6H, 15 2.044 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.03 (d, 6H,
2xCH3); 8,02; 8,77; 8,88; 9,37; 9,48; 9,56 (6H, =CH, Aryl/ Hetaryl).  2xCH3); 8.02; 8.77; 8.88; 9.37; 9.48; 9.56 (6H, = CH, aryl / hetaryl).
LC-MS = 269,1 (M+l) [ohne HCOOH]  LC-MS = 269.1 (M + 1) [without HCOOH]
16 1,960 1H-NMR(400,0 MHz, de-DMSO): δ = 1,18 (t, 3H, CH3); 1,960 16 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.18 (t, 3H, CH 3);
3,37 (m, 2H, CH2); 8,50; 8,77; 8,88; 9,39; 9,56; (5H, =CH, Aryl/ Hetaryl). 3.37 (m, 2H, CH 2 ); 8.50; 8.77; 8.88; 9.39; 9.56; (5H, = CH, aryl / hetaryl).
LC-MS = 269.0 (M+l) 268.27 (berechnet)  LC-MS = 269.0 (M + 1) 268.27 (calculated)
17 2,602 1H-NMR(400,0 MHz, de-DMSO): δ = 1,20 (d, 6H, 17 2.602 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.20 (d, 6H,
2xCH3); 4,16 (m, 1H, CH); 8,60; 8,63; 8,80; 9,31 ; 9,37; 9,56 (7H, =CH, Aryl/ Hetaryl). 2xCH 3 ); 4.16 (m, 1H, CH); 8.60; 8.63; 8.80; 9,31; 9.37; 9.56 (7H, = CH, aryl / hetaryl).
LC-MS = 300,0 (M+l); 299.30 (berechnet)  LC-MS = 300.0 (M + 1); 299.30 (calculated)
18 2,567 1H-NMR(400,0 MHz, de-DMSO): δ = 3,95; 2,92 (2s, 18 2.567 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.95; 2.92 (2s,
6H, 2xCH3); 8,20; 8,55; 8,58; 9,22; 9,28 (5H, =CH, Aryl/ Hetaryl). 6H, 2xCH 3 ); 8.20; 8.55; 8.58; 9.22; 9.28 (5H, = CH, aryl / hetaryl).
LC-MS = 350,1 (M+l) [ohne HCOOH]  LC-MS = 350.1 (M + 1) [without HCOOH]
19 2,521 1H-NMR(400,0 MHz, de-DMSO): δ = 2,87 (d, 3H, 19 2.521 1 H-NMR (400.0 MHz, de-DMSO): δ = 2.87 (d, 3H,
CH3); 8,45; 8,61 ; 8,80; 9,31 ; 9,36; 9,55 (6H, =CH, Aryl/ Hetaryl). CH 3 ); 8.45; 8.61; 8.80; 9,31; 9.36; 9.55 (6H, = CH, aryl / hetaryl).
LC-MS = 271,9 (M+); 271.24 (berechnet) LC-MS = 271.9 (M + ); 271.24 (calculated)
20 2,420 1H-NMR(400,0 MHz, de-DMSO): δ = 2,02 (d, 6H, 20 2.420 1 H-NMR (400.0 MHz, de-DMSO): δ = 2.02 (d, 6H,
2xCH3); 8,01 ; 8,61; 8,79; 9,31 ; 9,34; 9,48 (6H, =CH, Aryl/ Hetaryl). 2xCH 3 ); 8.01; 8.61; 8.79; 9,31; 9.34; 9.48 (6H, = CH, aryl / hetaryl).
LC-MS = 285,9 (M+); 285.2763 (berechnet) LC-MS = 285.9 (M + ); 285.2763 (calculated)
21 2,099 1H-NMR(400,0 MHz, de-DMSO): δ = 3,32; 3,72 (2s, 21 2.099 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.32; 3.72 (2s,
6H, 2xCH3); 8,10; 8,77; 8,88; 9,39; 9,50, 9,56 (6H, =CH, Aryl/ Hetaryl). 6H, 2xCH 3 ); 8.10; 8.77; 8.88; 9.39; 9.50, 9.56 (6H, = CH, aryl / hetaryl).
LC-MS = 285.1 (M+l) [ohne HCOOH]  LC-MS = 285.1 (M + 1) [without HCOOH]
22 1,834 1H-NMR(400,0 MHz, de-DMSO): δ = 3,31 ; 3,71 (2s, 22 1.834 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.31; 3.71 (2s,
6H, 2xCH3); 8,11 ; 9,36; 9,51; 9,60 (4H, =CH, Aryl/ Hetaryl). 6H, 2xCH 3 ); 8:11; 9.36; 9.51; 9.60 (4H, = CH, aryl / hetaryl).
LC-MS = 285,1 (M+l); 284.27 (berechnet)  LC-MS = 285.1 (M + 1); 284.27 (calculated)
23 2,104 1H-NMR(400,0 MHz, de-DMSO): δ = 2,99; 3,02 (2s, 23 2.104 1 H-NMR (400.0 MHz, de-DMSO): δ = 2.99; 3.02 (2s,
6H, 2xCH3); 7,94; 8,16; 8,54; 9,02; 9,29 (5H, =CH, Aryl/ Hetaryl). 6H, 2xCH 3 ); 7.94; 8.16; 8.54; 9.02; 9.29 (5H, = CH, aryl / hetaryl).
LC-MS = 285.1 (M+l) [ohne HCOOH]  LC-MS = 285.1 (M + 1) [without HCOOH]
24 2,251 1H-NMR(400,0 MHz, de-DMSO): δ = 3,40; 3,95 (2s, 24 2.251 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.40; 3.95 (2s,
6H, 2xCH3); 8,20; 8,59; 9,22; 9,29 (4H, =CH, Aryl/ Hetaryl). Bsp.-Nr. Retentionszeit [min] Ή-NMR [δ (ppm)] bzw. LC-MS [m/z] 6H, 2xCH 3 ); 8.20; 8.59; 9.22; 9.29 (4H, = CH, aryl / hetaryl). Expl Retention time [min] Ή-NMR [δ (ppm)] or LC-MS [m / z]
LC-MS = 321.1 (M+l) [ohne HCOOH]  LC-MS = 321.1 (M + 1) [without HCOOH]
25 2,376 1H-NMR(400,0 MHz, de-DMSO): δ = 1,64 (t, 3H, CH3); 2.376 25 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.64 (t, 3H, CH 3);
3,81 (m, 2H, CH2); 3,94 (s, 3H, CH3); 8,18; 8,46; 8,56; 9,14; 9,26 (5H, =CH, Aryl/ Hetaryl); 8,92 (br., 1H, NH). 3.81 (m, 2H, CH 2); 3.94 (s, 3H, CH3); 8.18; 8.46; 8.56; 9.14; 9.26 (5H, = CH, aryl / hetaryl); 8.92 (br., 1H, NH).
LC-MS = 321.0 (M+l); 320.29 (berechnet) LC-MS = 321.0 (M + 1); 320.29 (calculated)
26 2,112 1H-NMR(400,0 MHz, de-DMSO): δ = 3,71 ; (s, 3H, 26 2.122 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.71; (s, 3H,
CH3); 8,08; 8,61 ; 8,79; 9,31 ; 9,35; 9,49 (6H, =CH, Aryl/ Hetaryl). CH 3 ); 8.08; 8.61; 8.79; 9,31; 9.35; 9.49 (6H, = CH, aryl / hetaryl).
LC-MS = 302.0 (M+l); 301.27 (berechnet)  LC-MS = 302.0 (M + 1); 301.27 (calculated)
27 2,647 1H-NMR(400,0 MHz, de-DMSO): δ = 1,65 (t, 3H, CH3); 27 2.647 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.65 (t, 3H, CH 3 );
3,83 (m, 2H, CH2); 8,51 ; 8,60; 8,80; 9,31 ; 9,40; 9,58 (6H, =CH, Aryl/ Hetaryl); 8,96 (br, 1H, NH). 3.83 (m, 2H, CH 2 ); 8.51; 8.60; 8.80; 9,31; 9.40; 9.58 (6H, = CH, aryl / hetaryl); 8.96 (br, 1H, NH).
LC-MS = 336.0 (M+l); 335.28 (berechnet)  LC-MS = 336.0 (M + 1); 335.28 (calculated)
28 2,485 1H-NMR(400,0 MHz, de-DMSO): δ = 1,64 (s, 3H, CH3); 28 2.485 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.64 (s, 3H, CH 3 );
3,83 (m, 2H, CH2); 7,71 ; 8,51 ; 8,56; 8,74; 9,38; 9.53 (6H, =CH, Aryl/ Hetaryl); 8,95 (br., 1H, NH). 3.83 (m, 2H, CH 2 ); 7.71; 8.51; 8.56; 8.74; 9.38; 9.53 (6H, = CH, aryl / hetaryl); 8.95 (br., 1H, NH).
LC-MS = 318,1 (M+l) [ohne HCOOH]  LC-MS = 318.1 (M + 1) [without HCOOH]
29 1,888 1H-NMR(400,0 MHz, de-DMSO): δ = 0,71 (m, 4H, 29 1.888 1 H-NMR (400.0 MHz, de-DMSO): δ = 0.71 (m, 4H,
CH2CH2); 2,94 (m, 1H, CH); 7,71 ; 8,44; 8,55; 8,68; 8,74; 9,32; 9,37; 9,50 (7H, =CH, Aryl/ Hetaryl + NH). CH2CH2); 2.94 (m, 1H, CH); 7.71; 8.44; 8.55; 8.68; 8.74; 9.32; 9.37; 9.50 (7H, = CH, aryl / hetaryl + NH).
LC-MS = 280.0 (M+l); 279.29 (berechnet) LC-MS = 280.0 (M + 1); 279.29 (calculated)
30 2,040 1H-NMR(400,0 MHz, de-DMSO): δ = 2,86 (d, 3H, 30 2.040 1 H-NMR (400.0 MHz, de-DMSO): δ = 2.86 (d, 3H,
CH3); 7,71 ; 8,44; 8,54; 8,75; 9,35; 9,37; 9,50 (7H, =CH, Aryl/ Hetaryl). CH 3 ); 7.71; 8.44; 8.54; 8.75; 9.35; 9.37; 9.50 (7H, = CH, aryl / hetaryl).
LC-MS = 254.0 (M+l) [ohne HCOOH]  LC-MS = 254.0 (M + 1) [without HCOOH]
31 2,629 1H-NMR(400,0 MHz, de-DMSO): δ = 1,15 (t, 3H, 31 2.629 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.15 (t, 3H,
CH3); 3.36 (m, 2H, CH2); 7,71 ; 8,45; 8,56; 8,76; 8,80; 9,37; 9,51 (7H, =CH, Aryl/ Hetaryl). CH 3 ); 3.36 (m, 2H, CH2); 7.71; 8.45; 8.56; 8.76; 8.80; 9.37; 9.51 (7H, = CH, aryl / hetaryl).
LC-MS = 268.0 (M+l); 267.28 (berechnet)  LC-MS = 268.0 (M + 1); 267.28 (calculated)
32 2,133 1H-NMR(400,0 MHz, de-DMSO): δ = 3,30; 3,71 ; 3,94 32 2.133 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.30; 3.71; 3.94
(3s, 9H, 3xCH3); 8,03; 8,17; 8,55; 9,06; 9,22 (5H, =CH, Aryl/ Hetaryl).  (3s, 9H, 3xCH3); 8.03; 8.17; 8.55; 9.06; 9.22 (5H, = CH, aryl / hetaryl).
LC-MS = 287,1 (M+l) [ohne HCOOH]  LC-MS = 287.1 (M + 1) [without HCOOH]
33 2,182 1H-NMR(400,0 MHz, de-DMSO): δ = 1,24 (d, 6H, 33 2.182 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.24 (d, 6H,
2xCH3); 4,16 (m, 1H, CH); 8,17; 8,40; 8,54; 9,12; 9,22 (5H, =CH, Aryl/ Hetaryl). 2xCH 3 ); 4.16 (m, 1H, CH); 8.17; 8.40; 8.54; 9.12; 9.22 (5H, = CH, aryl / hetaryl).
34 2,167 1H-NMR(400,0 MHz, de-DMSO): δ = 3.75 (br, 2H, 34 2.167 1 H-NMR (400.0 MHz, de-DMSO): δ = 3.75 (br, 2H,
CH2); 6,17 (dt, 1H, CH); 8,17; 8,45; 8,55; 9,14; 9,25 (5H, =CH, Aryl/ Hetaryl); 9,02 (br., 1H, NH). CH 2 ); 6.17 (dt, 1H, CH); 8.17; 8.45; 8.55; 9.14; 9.25 (5H, = CH, aryl / hetaryl); 9.02 (br., 1H, NH).
LC-MS = 307.1 (M+l) [ohne HCOOH]  LC-MS = 307.1 (M + 1) [without HCOOH]
35 1,840 1H-NMR(400,0 MHz, de-DMSO): δ = 2,84 (d, 3H, 35 1.840 1 H-NMR (400.0 MHz, de-DMSO): δ = 2.84 (d, 3H,
CH3); 3,94 (s, 3H, CH3); 8,16; 8,40; 8,54; 9,11 ; 9,22 (5H, =CH, Aryl/ Hetaryl), 8,72 (1H, NH). CH 3 ); 3.94 (s, 3H, CH3); 8.16; 8.40; 8.54; 9.11; 9.22 (5H, = CH, aryl / hetaryl), 8.72 (1H, NH).
LC-MS = 257.0 (M+l) [ohne HCOOH] Bsp.-Nr. Retentionszeit [min] Ή-NMR [δ (ppm)] bzw. LC-MS [m/z] LC-MS = 257.0 (M + 1) [without HCOOH] Expl Retention time [min] Ή-NMR [δ (ppm)] or LC-MS [m / z]
36 3.085 MHZ, de-DMSO): δ = 3,76 (m, 2H, 36 3,085 MHZ, de-DMSO): δ = 3.76 (m, 2H,
CH2); 6,18 (dt, 1H, CH); 7,71 ; 8,50; 8,56; 8,75; 9,05; 9,38; 9,53 (7H, =CH, Aryl/ Hetaryl). CH 2 ); 6.18 (dt, 1H, CH); 7.71; 8.50; 8.56; 8.75; 9.05; 9.38; 9.53 (7H, = CH, aryl / hetaryl).
LC-MS = 304.1 (M+l); 303.26 (berechnet)  LC-MS = 304.1 (M + 1); 303.26 (calculated)
37 2,469 1H-NMR(400,0 MHz, de-DMSO): δ = 0,70 (m, 4H, 37 2,469 1 H-NMR (400.0 MHz, de-DMSO): δ = 0.70 (m, 4H,
CH2CH3); 2,92 (m, 1H, CH); 8,16; 8,40; 8,54; 9,11 ; 9,19 (5H, =CH, Aryl/ Hetaryl), 8,63 (1H, NH).  CH2CH3); 2.92 (m, 1H, CH); 8.16; 8.40; 8.54; 9.11; 9.19 (5H, = CH, aryl / hetaryl), 8.63 (1H, NH).
LC-MS = 283.1 (M+l) [ohne HCOOH]  LC-MS = 283.1 (M + 1) [without HCOOH]
38 2,792 1H-NMR(400,0 MHz, de-DMSO): δ = 1,21 ; 1,23 (2s, 38 2,792 1 H-NMR (400.0 MHz, de-DMSO): δ = 1.21; 1.23 (2s,
6H, 2xCH3); 4,15 (m, 1H, CH); 7,71 ; 8,44; 8,55; 8,74; 9,36; 9,38; 9,51 (7H, =CH, Aryl/ Hetaryl). 6H, 2xCH 3 ); 4.15 (m, 1H, CH); 7.71; 8.44; 8.55; 8.74; 9.36; 9.38; 9.51 (7H, = CH, aryl / hetaryl).
LC-MS = 282.1 (M+l); 281.31 (berechnet)  LC-MS = 282.1 (M + 1); 281.31 (calculated)
Biologische Beispiele Biological examples
Myzus persicae - Sprühtest 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. 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), die von allen Stadien der Grünen Pfirsichblattlaus {Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. 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 bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. After 6 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 500 g/ha: 1, 4, 6, 7, 8, 10. In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 500 g / ha: 1, 4, 6, 7, 8, 10th
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90 % bei einer Aufwandmenge von 500 g/ha: 3, 5, 11, 14, 15, 19, 20, 26, 28, 29, 30, 31, 36. Tetranychus urticae - Sprühtest, OP-resistent In this test, z. Example, the following compounds of the manufacturing examples effect of 90% at a rate of 500 g / ha: 3, 5, 11, 14, 15, 19, 20, 26, 28, 29, 30, 31, 36. Tetranychus urticae - spray test, op-resistant
Lösungsmittel GewichtsteileAceton Solvent parts by weight acetone
Gewichtsteile Dimethylformamid  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 which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water.
Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. 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 bedeutet 100 %, dass alle Spinnmilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden. After 6 days, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90 % bei einer Aufwandmenge von 500 g/ha: 3. In this test, z. For example, the following compounds of the Preparation Examples have an effect of 90% at a rate of 500 g / ha: 3.
Musca domestica-Test Musca domestica test
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
Gefäße, die einen Schwamm enthalten, der mit Zuckerlösung und der Wirkstoffzubereitung der gewünschten Konzentration behandelt wurde, werden mit 10 adulten Stubenfliegen (Musca domestica) besetzt. Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Fliegen abgetötet wurden; 0 % bedeutet, dass keine der Fliegen abgetötet wurde. After 2 days the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed.
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 100 ppm: 14, 15. In this test, e.g. the following compounds of the preparation examples an effect of 80% at an application rate of 100 ppm: 14, 15.

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-a) bis (A-f in which A is an A radical from the series (Aa) to (Af
(A-a)  (A-a)
steht, worin die gestrichelte Linie die Bindung zum Stickstoffatom des Bicyclus der Formel (I) bedeutet und wherein the dashed line represents the bond to the nitrogen 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,
R a) für einen B-Rest aus der Reihe (B-l) bis (B-36) WO 2016/087363 PCT/EP2015/078051 R a) for a B radical from the series (B1) to (B-36) WO 2016/087363 PCT / EP2015 / 078051
(Β-29) (Β-29)
(Β-30) (Β-31) (Β-32)  (Β-30) (Β-31) (Β-32)
(Β-33) (Β-34) (Β-35) (Β-36) (Β-33) (Β-34) (Β-35) (Β-36)
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) markiert, oder R b) für einen D-Rest aus der Reihe (D- 1 ) bis (D-3)  in which the dashed line marks the bond to the carbon atom of the bicyclic compound of the formula (I), or 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) markiert, oder c) für einen Rest der Formel  (D-1) (D-2) (D-3), wherein the dotted line marks 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 dem Formel (I) markiert, oder wherein the dashed line marks the bond to the carbon atom of the bicycle of formula (I), or
R2 d) für einen Rest der Formel X R 2 d) is a radical of the formula X
IM ^ R22 IM ^ R22
I ?Q I ? Q
R steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) markiert, oder e) für einen F-Rest aus der Reihe (F-l) bis (F-l 1)  R is in which the dashed line marks the bond to the carbon atom of the bicyclic compound of the formula (I), or e) for an F radical from the series (F-1) to (F-1)
R23 R8 R23 R8 23 R8 R 23 R 8 R 23 R 8 23 R 8
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) markiert, oder wherein the dashed line marks the bond to the carbon atom of the bicycle of formula (I), or
R f) für einen Rest aus der Reihe Halogenalkyl, Carboxyl und Amino steht, worin für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, Alkyl, Halogenalkyl, Alkoxycarbonylalkyl, 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, Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl,R f) is a radical from the group consisting of haloalkyl, carboxyl and amino, in which hydrogen or a radical selected from the group halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, alkoxycarbonylalkyl, 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 (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, 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) steht, worin die gestrichelte Linie die Bindung zu den Resten (B-l) bis (B-36) bedeutet, Alkoxycarbonylalkyl, alpha-hydroxyimino-alkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio, alkylsulfmyl, alkylsulfonyl, 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 themselves may in turn 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, imidazolyl, 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 themselves are substituted again may be halogen and alkyl), or a C-residue from the series (Cl) to (C-9) wherein the dashed line represents the bond to the radicals (B1) to (B-36),
X für Sauerstoff oder Schwefel steht, X is oxygen or sulfur,
XI für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy und Halogenalkoxy steht, X I is a radical from the series consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, 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 an 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 oder 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 or 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, 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, if appropriate 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, 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 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 selected from the group consisting of sulfur, oxygen (where oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group, 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,
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 R and R in the radicals (C-3) and (F-3) also together with the phosphorus atom to which they are bonded, a saturated or unsaturated and optionally substituted 5- to 7-membered
Ring bilden können, der ein oder zwei Heteroatome aus der Reihe Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Schwefel enthalten kann, Ring containing one or two heteroatoms selected from the group of oxygen (oxygen atoms may not be immediately adjacent) and 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, 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 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,
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 undR 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 contain) and nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and
Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht, 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 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,
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,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 which may contain one or more further heteroatoms from the sulfur,
Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann, Oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group,
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,R 18 is a radical from the series consisting of hydrogen, hydroxyl, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, in each case optionally substituted 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 Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl steht, Cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl in which the rings may contain at least one heteroatom selected from the group consisting of sulfur, oxygen (where oxygen atoms are not 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 or alkaline earth metal ion or an optionally mono- to quadruply C 1 -C 4 -alkyl-substituted ammonium ion or a respectively optionally Halogen or cyano-substituted radical alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, 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, W für einen Rest aus der Reihe O, S, SO und S02 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 is a radical from the series O, S, SO and SO 2 ,
R22 für einen Rest aus der Reihe Alkyl, gegebenenfalls durch Halogen, Carbamoyl, Thiocarbamoyl oder Cyano substituiertes Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyloxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkylthioalkyloxy, Alkylsulfinylalkyloxy, Alkylsulfonylalkyloxy, Halogenalkylthioalkyl, Halogenalkylsulfinylalkyl,R 22 is a radical from the series alkyl, optionally substituted by halogen, carbamoyl, thiocarbamoyl or cyano substituted cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylthioalkyloxy, Alkylsulfinylalkyloxy, alkylsulfonylalkyloxy, haloalkylthioalkyl, haloalkylsulfinylalkyl,
Halogenalkylsulfonylalkyl, Alkylthioalkenyl, Alkylsulfinylalkenyl, Alkylsulfonylalkenyl, Alkenylthioalkyl, Alkenylsulfinylalkyl, Alkenylsulfonylalkyl, Alkylcarbonylalkyl, Halogenalkylcarbonylalkyl, Alkoxyalkyl, Halogenalkoxyalkyl, Alkoxycarbonylalkyl, Halogenalkoxycarbonylalkyl, Alkylaminosulfonyl, Dialkylaminosulfonyl steht, oder, im Fall R2 = d), Haloalkylsulfonylalkyl, alkylthioalkenyl, alkylsulfinylalkenyl, alkylsulfonylalkenyl, alkenylthioalkyl, alkenylsulfinylalkyl, alkenylsulfonylalkyl, alkylcarbonylalkyl, haloalkylcarbonylalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxycarbonylalkyl, haloalkoxycarbonylalkyl, alkylaminosulfonyl, dialkylaminosulfonyl, or, in the case of R 2 = d),
R auch für gegebenenfalls substituiertes Aryl oder für einen E-Rest aus der Reihe E-l bis E-51 R also for optionally substituted aryl or for an E-radical from the series El to E-51
WO 2016/087363 PCT/EP2015/078051 WO 2016/087363 PCT / EP2015 / 078051
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-48 E-49 E-50 E-51 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-48 E-49 E-50 E-51 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 Halogengenalkylsulfonyl steht, für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylthioalkyl, Alkenylthioalkyl, Cyanoalkyl, Alkoxyalkyl steht 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, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl und Cyanoalkyl steht. 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 from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and halogenoalkylsulfonyl, a radical from the series consisting of hydrogen, Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl and represents hydrogen or a respectively 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 selected from hydrogen, alkyl, haloalkyl, alkenyl, alkynyl , Cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl.
Verbindungen der Formel (I) gemäß Anspruch 1 , in welchen Compounds of formula (I) according to claim 1, in which
A für einen Rest aus der Reihe (A-a), (A-b) und (A-f) (A-a) A for a residue from the series (Aa), (Ab) and (Af) (Aa)
(A-b) (A-f) steht, worin die gestrichelte Linie die Bindung zum Stickstoffatom des Bicyclus der Formel (I) bedeutet,  (A-b) (A-f), wherein the dotted line represents the bond to the nitrogen 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, B 1 is a radical selected from the group consisting of hydrogen and fluorine, B 2 is hydrogen,
T für ein Elektronenpaar steht, c) für den Rest der Formel T is an electron pair, c) the rest of the formula
steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
X für Sauerstoff steht, für Ci-C4-Alkyl steht, für einen Rest aus der Reihe Ci-Cö-Alkyl, C3-C6-Cycloalkyl, Ci-C6-Halogenalkyl, Ci-C6-Alkoxy, Ci-C i-Alkylsulfonyl und Di-(Ci-C4-alkyl)-aminosulfonyl steht und für Wasserstoff oder Ci-Cö-Alkyl steht. X is oxygen, C 1 -C 4 -alkyl, a radical selected from C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -alkylsulfonyl and di (Ci-C4-alkyl) -aminosulfonyl and is hydrogen or Ci-Cö-alkyl.
3. Verbindungen der Formel (I) gemäß Anspruch 1 oder 2, worin A für den Rest (A-b) steht. 3. Compounds of formula (I) according to claim 1 or 2, wherein A is the radical (Ab).
4. Verbindungen der Formel (I) gemäß Anspruch 1 oder 2, worin A für den Rest (A-f) steht. 4. Compounds of formula (I) according to claim 1 or 2, wherein A is the radical (A-f).
5. Verbindungen der Formel (I) gemäß Anspruch 1 oder 2, worin A für den Rest (A-a) steht. 5. Compounds of formula (I) according to claim 1 or 2, wherein A is the radical (A-a).
6. Mittel, gekennzeichnet durch einen Gehalt von mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 4 und üblichen Streckmitteln und/oder oberflächenaktiven Substanzen. 6. agent, characterized by a content of at least one compound of formula (I) according to any one of claims 1 to 4 and conventional extenders and / or surface-active substances.
7. Verwendung von Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 5 oder von Mitteln gemäß Anspruch 6 zur Bekämpfung von Schädlingen. 7. Use of compounds of the formula (I) according to one of claims 1 to 5 or of agents according to claim 6 for combating pests.
EP15801850.7A 2014-12-02 2015-11-30 Bicyclic compounds as pest control agents Withdrawn EP3227289A1 (en)

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TWI652014B (en) 2013-09-13 2019-03-01 美商艾佛艾姆希公司 Heterocyclic substituted bicycloazole insecticide
EP3268359B1 (en) 2015-03-12 2019-12-18 FMC Corporation Heterocycle-substituted bicyclic azole pesticides
KR102545036B1 (en) 2015-04-09 2023-06-20 에프엠씨 코포레이션 pyrazole insecticide
BR112019000569A2 (en) * 2016-07-12 2019-04-24 Bayer Cropscience Aktiengesellschaft bicyclic compounds as pesticides
MX2019003136A (en) * 2016-09-19 2019-07-18 Bayer Cropscience Ag Pyrazolo [1,5-a]pyridine derivatives and their use as pesticides.
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