WO2018054711A1 - Pyridine compounds for controlling phytopathogenic harmful fungi - Google Patents

Pyridine compounds for controlling phytopathogenic harmful fungi Download PDF

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WO2018054711A1
WO2018054711A1 PCT/EP2017/072765 EP2017072765W WO2018054711A1 WO 2018054711 A1 WO2018054711 A1 WO 2018054711A1 EP 2017072765 W EP2017072765 W EP 2017072765W WO 2018054711 A1 WO2018054711 A1 WO 2018054711A1
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alkyl
compounds
halogen
alkoxy
cycloalkyl
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PCT/EP2017/072765
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French (fr)
Inventor
Bernd Mueller
Erica CAMBEIS
Jan Klaas Lohmann
Ana Escribano Cuesta
Antje Wolf
Marcus Fehr
Nadine RIEDIGER
Christian Winter
Wassilios Grammenos
Violeta TERTERYAN-SEISER
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/42—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 condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Definitions

  • the present invention relates to pyridine compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the use and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound.
  • the invention also relates to processes for preparing these compounds, intermediates, processes for preparing such intermediates, and to compositions comprising at least one compound I.
  • the fungicidal activity of the known fungi- cidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic harmful fungi.
  • the present invention relates to the com ounds of formula I
  • R 1 is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 - alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the het- eroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
  • R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents R x1 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
  • R 1 wherein the acyclic moieties of R 1 are unsubstituted or substituted by groups R 1a which independently of one another are selected from:
  • R 1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 - halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R 11a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogen- alkoxy;
  • R 1 wherein the carbocyclic, heteroaryl and aryl moieties of R 1 are unsubstituted or substituted by groups R 1b which independently of one another are selected from:
  • R 1b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio;
  • R 2 is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 - alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
  • R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents R x1 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
  • R 2 wherein the acyclic moieties of R 2 are unsubstituted or substituted by groups R 2a which independently of one another are selected from:
  • R 2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 - halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted or substituted by substituents R 22a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogen- alkoxy;
  • R 2b which independently of one another are selected from: R 2b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl,
  • R 3 is in each case independently selected from CH 3 , CH 2 F, CHF 2 and CF 3 ;
  • R 4 wherein the acyclic moieties of R 4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 4a , which independently of one another are selected from:
  • R x is as defined above;
  • n 0, 1 , 2 or
  • R 3 , R 4 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N , O and S, wherein the heteroatom N may carry one substituent selected from Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl and S0 2 Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from CN , Ci-C 4 -al- kyl, halogen, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or S0 2 , and wherein the carbocycle or heterocycle is unsubstituted or
  • R 5 is H
  • R 6 is H
  • A is selected from below group:
  • Y is H
  • o 0, 1 , 2 or 3;
  • R 78a halogen, OH , CN , Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 - halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or substituted by R 78aa selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
  • R 78 wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R 78 are unsubstituted or substituted by R 78b which independently of one another are selected from:
  • R 78b halogen, OH , CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio;
  • R x is as defined above;
  • R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6- alkynyl, C 2 -C6-halogenalkynyl, C 3 -C6-cycloalkyl, and C 3 -C6-halogencycloalkyl; wherein the acyclic moieties of R 9 are unsubstituted or substituted by groups R 9a which independently of one another are selected from:
  • R 9a halogen, OH , CN , d-Ce-alkoxy, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R 91a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
  • groups R 9b which independently of one another are selected from:
  • R 9b halogen, OH , CN , C C 4 -alkyl, C C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
  • R 10 is in each case independently selected from the substituents as defined for R 9 , wherein the possible substituents for R 10 are R 10a and R 10b , respectively, which correspond to R 9a and R 9b , respectively;
  • R 11 is in each case independently selected from halogen, OH, CN, NO2, SH, NH 2 , NH(Ci-C4- alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , d-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 - alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;
  • R x is as defined above;
  • R 11 wherein the acyclic moieties of R 11 are unsubstituted or substituted with identical or different groups R 11a which independently of one another are selected from:
  • R 11a halogen, OH, CN, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio;
  • R 11b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; with the provisio that f A is phenyl,
  • R 1 is H
  • R 4 can not be unsubstituted Ci-C6-alkyl
  • R 10 can not be H
  • the reaction is performed at a temperature from -40°C to 200°C, in particular from -10°C to 120°C, more specifically from 0°C to 100°C, even more specifically from room or ambient temperature (about 23°C) to 80°C.
  • Nitriles of type II I are either commercially available or can be prepared by a skilled person from the corresponding halides following literature precedures (see, for example Journal of Organic Chemistry, 76(2), 665-668; 201 1 ; Angewandte Chemie, International Edition, 52(38), 10035- 10039; 2013; WO2004/013094).
  • Alcohols of type I I can be prepared as described below. A skilled person will realize that compounds of type l llb can be reacted with organometallic reagents, preferably alkyl Grignard or al- kyl-Lithium reagents, in ethereal solvents, preferably THF at low temperatures and under inert conditions to furnish compounds of type I I.
  • organometallic reagents preferably alkyl Grignard or al- kyl-Lithium reagents
  • alcohols of type I I can be prepared from epoxydes I l ia and compounds VI (see below):
  • the metallation reaction may preferably be carried out using Lithium-organic compounds, such as for example n-butyl lithium, sec-butyl lithium or tert-butyl lithium to result in an exchange of halogen by lithium. Also suitable is the reaction with magnesium resulting in the formation of the respective Grignard reagents. A further possibility is the use of other Grignard reagents such as isopropyl-magnesium-bromide instead of Mg.
  • a typical preparation of compounds of type l llb can be achieved by reacting compounds of type IV with organometallic reagents, preferably alkyl Grignard or alkyl-Lithium reagents, in ethereal solvents, preferably THF at low temperatures and under inert conditions to furnish compounds of type III as previously reported (see for example WO2012051036; WO201 1042918).
  • organometallic reagents preferably alkyl Grignard or alkyl-Lithium reagents
  • an organic solvent preferably THF or dichloromethane.
  • the reaction is performed in a range between 0 °C and ambient temperature in the presence of an organic base, preferably N(C2Hs)3 or pyridine (see e.g. US 20130324506; Tetrahedron: Asymmetry, 17(4), 508-51 1 ; 2006).
  • an activating reagent preferably a carbodiimide
  • an activating reagent preferably a carbodiimide
  • compounds of type V can be prepared from the corresponding aryl halides of type VI (Hal is halogen, preferably Br or I). As described (Tetrahedron, 68(9), 21 13-2120; 2012; Chemical Communications (Cambridge, United Kingdom), 49(60). 6767-6769; 2013), aryl halides will react with compounds of type VII in the presence of a transition metal catalyst, preferably a cop- per(l) salt, in an organic solvent, preferably DMF or DMSO, at elevated temperatures. Typically a base, preferably potassium phosphate, is added.
  • compounds of type II can be prepared as follows.
  • a known or commercially available compound of type VIII can be reacted with an organometallic reagent of type IX, preferably a Grignard or an organolithium reagent, readily prepared by a skilled person.
  • the reaction is performed in a temperature range from -78 °C to room temperature under inert conditions in an ethereal solvent.
  • Alternatively compounds I can be prepared via intramolecular reaction of amide X when A is an electron-rich carbon- or heterocycle.
  • the intramolecular cyclization will take place in the presence of a dehydrating agent in an organic solvent (WO 2008143263, Synthetic Communications 2007, 37, 1331 -1338.).
  • a dehydrating agent in an organic solvent
  • POCI 3 phosphoryl chloride
  • POCI3/P2O5, H3PO4/P2O5, SnCU or BF3 are used as dehydrating agent.
  • suitable solvents are hydrocarbons, prefera- bly benzene, toluene or acetonitrile.
  • halogenated solvents can be used, for example dichloromethane, chloroform or chlorobenzene.
  • the reaction is performed at temperature from - 40°c to 200 °C, in particular from -10°C to 120°C, more specifically from 0°C to 100°C, even more specifically from room temperature to 100°C.
  • an activating agent preferably a carbodiimide or acid chloride
  • compounds of type XII can be synthesized from the correspond nitriles.
  • nitriles will react with or- ganometallic agents, preferably Grignard or Lithium reagent, in ethereal solvents, preferably THF at low temperature and under inert conditions to furnish compounds of type XII.
  • the synthesis of compounds of type XII can take place in two steps or one pot.
  • the N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroper- benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(1 1 ), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981 ) or ox- one (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001 ).
  • the oxidation may lead to pure mono- N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
  • the intermediate compounds of formula X are novel. Consequently, one aspect of the present invention relates to compounds of formula X:
  • the intermediate compounds of formula X are novel. Consequently, one aspect of the present invention relates to compounds of formula X:
  • the compounds of formula X have fungicidal activity and the details below referring to the pounds I also apply to compounds X.
  • C n -C m indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
  • halogen refers to fluorine, chlorine, bromine and iodine.
  • Ci-C6-alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dime- thylpropyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethyl- butyl, 2,2-dimethylbutyl, 2,3-dimethylbut
  • C2-C4-alkyl refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propoyl), butyl, 1 -methylpropyl (sec- butyl), 2-methylpropyl (iso-butyl), 1 ,1-dimethylethyl (tert.-butyl).
  • CrC 6 -halogenalkyl refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • Examples are "Ci-C2-halogenalkyl” groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlor- ofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoro- ethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-
  • Ci-C6-hydroxyalkyl refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by OH groups.
  • CrC4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above).
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C6-alkoxy group (as defined above).
  • C2-C6-alkenyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position.
  • Examples are “C2-C4-alkenyl” groups, such as ethenyl, 1 -propenyl, 2-propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl.
  • C2-C6-alkynyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond.
  • Examples are “C2-C4-al- kynyl” groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but-
  • Ci-C6-alkoxy refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group.
  • Examples are “C1-C4- alkoxy” groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1 -methyhprop- oxy, 2-methylpropoxy or 1 ,1-dimethylethoxy.
  • Ci-C6-halogenalkoxy refers to a Ci-C6-alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • Examples are "Ci-C4-halogenalkoxy” groups, such as OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro- ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, OC2F5, 2-fluoropropoxy,
  • C2-C6-alkenyloxy refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are “C2-C4-alkenyloxy” groups.
  • C2-C6-alkynyloxy refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are “C2-C4-alkynyloxy” groups.
  • C3-C6-cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbo- cycle is a "C3-Cio-cycloalkyl".
  • C3-C6-cycloalkenyl refers to a monocyclic partially unsaturated 3-, 4- 5- or 6-mem- bered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cy- clopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four- , five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C3-Cio-cycloal- kenyl".
  • C3-C8-cycloalkyl-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).
  • Ci-Ce-alkylthio refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the term “Ci- C6-halogenalkylthio” as used herein refers to straight-chain or branched halogenalkyi group hav- ing 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the halogenalkyi group.
  • the number of valence of carbon is 4, that of nitrogen is 3.
  • saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten- membered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and S.
  • saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten- membered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and
  • a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azet- idine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine; and
  • a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O, N and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isox- azolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazoli- dinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazoli- dinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imi
  • a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroaze- pinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahy- dro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1-,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[
  • substituted refers to substitued with 1 , 2, 3 or up to the maximum possible number of substituents.
  • 5-or 6-membered heteroaryl or “5-or 6-membered heteroaromatic” refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example,
  • a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan- 2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl
  • a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyri- dazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • Agriculturally acceptable salts of the inventive compounds encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of said compounds.
  • Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammo- nium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfox
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting such inventive compound with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the inventive compounds can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.
  • the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure di- astereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or dia- stereomers and their mixtures are subject matter of the present invention.
  • R 1 is in each case independently selected from hydrogen, halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
  • heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
  • R x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R x1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
  • R 1 wherein the acyclic moieties of R 1 are unsubstituted or substituted with identical or different groups R 1a which independently of one another are selected from:
  • R 1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, C1-C4- halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
  • R 1 wherein the carbocyclic, heteroaryl and aryl moieties of R 1 are unsubstituted or substituted with identical or different groups R 1b which independently of one another are selected from:
  • R 1b halogen, OH, CN, C C 4 -alkyl, C C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
  • R 1 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R 1 that may be present in the ring.
  • R 1 is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
  • R 1 is hydrogen
  • R 1 is halogen, in particular Br, F or CI, more specifically F or CI.
  • R 1 is F
  • R 1 is CI
  • R 1 is Br.
  • R 1 is OH
  • R 1 is CN
  • R 1 is NO2.
  • R 1 is SH.
  • R 1 is NH 2 , NH(CrC4-alkyl), N(CrC4-alkyl) 2 or NH-S02-R X , wherein R x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R x1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy.
  • R 1 is Ci-C6-alkyl, in particular Ci-C4-alkyl,
  • R 1 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI 2 , CH 2 CI, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
  • R 1 is C 2 -C6-alkynyl or C 2 -C6-halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as C ⁇ CH, C ⁇ CCI, C ⁇ CF. CH 2 C ⁇ CH, CH 2 C ⁇ CCI, or CH 2 C ⁇ CF.
  • R 1 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C 2 -alkoxy such as OCH 3 or OCH 2 CH 3 .
  • R 1 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C 2 -halogenalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCI 3 , OCHCI 2 or OCH 2 CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 1 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
  • R 1 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R 1b as defined and preferably herein.
  • R 1 is C3-C6-halogencycloalkyl.
  • R 1 is fully or partially halogenated cyclopropyl.
  • R 1 is unsubstituted aryl or aryl that is substituted by one, two, three or four R 1b , as defined herein.
  • R 1 is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R 1b , as defined herein.
  • R 1 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R 1 is 5- or 6-membered heteroaryl that is substituted by one, two or three R 1b , as defined herein.
  • R 1 is in each case independently selected from hydrogen, halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C6-alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R 1 are not further substituted or carry one, two, three, four or five identical or different groups R 1a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R 1 are not further substituted or carry one, two, three, four or five identical or different groups R 1b as defined below.
  • R 1 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and CrC 4 -halogenalkoxy.
  • R 1a are the possible substituents for the acyclic moieties of R 1 .
  • R 1a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 11a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci- C 4 -halogenalkoxy, in particular selected from halogen, Ci-C 2 -alkyl, Ci-C 2 -halogenalkyl, Ci-C 2 - alkoxy and Ci-C 2 -halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
  • halogen such as F, CI and Br.
  • R 1a is independently selected from halogen, OH, CN, Ci-C 2 -alkoxy, C 3 - C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C 2 -halogenalkoxy. Specifically, R 1a is
  • R 1a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
  • R 1a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C 2 -halogenalkoxy. Specifically, R 1a is
  • R 1b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R 1 .
  • R 1b according to the invention is independently selected from halogen, OH, CN, Ci-C 4 -alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
  • R 1b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-hal- ogenalkoxy.
  • R 1b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1-F 2 -cyclopropyl, 1 ,1-Cl2-cyclopropyl and halogenmethoxy.
  • R 1b is independently selected from halogen, C-i- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy.
  • R 1b is independently selected from halogen, CN, OH, CH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F 2 -cyclopropyl, 1 ,1 -C - cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF 2 , OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F 2 -cyclopropyl, 1 ,1 -C - cyclopropyl, OCHF 2 and OCF 3 .
  • R x in the substituent NH-S02-R X is in each case independently selected from Ci-C4-alkyl, C1-C4- halogenalkyl, unsubstituted aryl and aryl that is substituted by one, two, three, four or five substituents R x1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
  • R x is in each case independently selected from Ci-C4-alkyl, halogen, OH, CN and phenyl that is substituted by one, two or three R x1 independently selected from Ci-C2-alkyl, more specifically R x is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted by one CH3., more specifically S02-R x is the tosyl group ("Ts").
  • R 1 Particularly preferred embodiments of R 1 according to the invention are in Table P1 below, wherein each line of lines P1 -1 to P1-16 corresponds to one particular embodiment of the inven- tion. Thereby, for every R 1 that is present in the inventive compounds, these specific
  • Ts stands for the tosylgroup S02-(p-CH3)phenyl.
  • R 2 is in each case independently selected from hydrogen, halogen, OH, CN, NO2, SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
  • heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
  • R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R x2 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
  • R 2 wherein the acyclic moieties of R 2 are unsubstituted or substituted with identical or different groups R 2a which independently of one another are selected from:
  • R 2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C 4 -halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 22a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 - halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
  • R 2 wherein the carbocyclic, heteroaryl and aryl moieties of R 2 are unsubstituted or substituted with identical or different groups R 2b which independently of one another are selected from:
  • R 2b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalky, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
  • R 2 is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH 3 , F or CI most preferred H, F or CI.
  • R 2 is halogen, in particular Br, F or CI, more specifically F or CI.
  • R 2 is F
  • R 2 is CI
  • R 2 is Br
  • R 2 is hydrogen
  • R 2 is OH
  • R 2 is CN
  • R 2 is N0 2 .
  • R 2 is SH.
  • R 2 is NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 or NH-S0 2 -R x , wherein R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R x2 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy, or Ci-C 4 -halogenalkoxy.
  • R 2 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH 3 or CH 2 CH 3 .
  • R 2 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI2, CH2CI, CF3CH2, CCI3CH2 or CF 2 CHF 2 .
  • R 2 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as C ⁇ CH, C ⁇ CCI, C ⁇ CF. CH 2 C ⁇ CH, CH 2 C ⁇ CCI, or CH 2 C ⁇ CF.
  • R 2 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
  • R 2 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCI3, OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 2 is C3-C6-cycloalkyl, in particular cyclopropyl.
  • R 2 is C3-C6-cycloalkyl, for example cyclopropyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R 2b as de- fined and preferably herein.
  • R 2 is C3-C6-halogencycloalkyl.
  • R 2 is fully or partially halogenated cyclopropyl.
  • R 2 is unsubstituted aryl or aryl that is substituted by one, two, three or four R 2b , as defined herein.
  • R 2 is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R 2b , as defined herein.
  • R 2 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R 2 is 5- or 6-membered heteroaryl that is substituted by one, two or three R 2b , as defined herein.
  • R 2 is in each case independently selected from hydrogen, halogen, OH, CN, N0 2 , SH, NH 2 , NH(C C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R 2 are not further substituted or carry one, two, three, four or five identical or different groups R 2a as defined below and wherein the cycloalkyl moieties of R 2 are not further substituted or carry one, two, three, four or five identical or different groups R 2b as defined below.
  • R 2 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
  • R 2a are the possible substituents for the acyclic moieties of R 2 .
  • R 2a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
  • R 2a is independently selected from halogen, OH, CN, C1-C2- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy.
  • R 2a is independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
  • R 2a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
  • R 2a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R 2a is
  • R 2b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R 2 .
  • R 2b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C4-halogen- alkoxy.
  • R 2b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy.
  • R 2b is independently selected from F, CI, OH, CN, CH 3 , OCH 3 , cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and halogenmethoxy.
  • R 2b is independently selected from halogen, C-i- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy.
  • R 2b is independently selected from halogen, OH, CH3, OCH3, CN, CHF2, OCHF2, OCF3, OCH3 cyclopropyl, 1 -F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1-F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-CI 2 -cyclopropyl, OCHF 2 and OCF 3 .
  • R 2 according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-16 corresponds to one particular embodiment of the invention. Thereby, for every R 2 that is present in the inventive compounds, these specific
  • Ts in the table stands for the tosylgroup S02-(p-CH 3 )phenyl.
  • R 3 is in each case independently selected from CH3, CH2F, CHF2 and CF3.
  • R 3 is CH3.
  • R 3 is CH 2 F.
  • R 3 is CHF 2 .
  • R 3 is CF3.
  • R 4 wherein the carbo-, heterocyclic, heteroaryl and aryl moieties of R 4 are independently unsubstituted or substituted with identical or different groups R 4b , which independently of one another are selected from:
  • n 0, 1 , 2.
  • carbo-, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen,
  • R 4 wherein the carbo-, heterocyclic, heteroaryl and aryl moieties of R 4 are independently unsubsti- tuted or substituted with identical or different groups R 4b , which independently of one another are selected from:
  • n 0, 1 , 2.
  • R 4 is selected from Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted by substituents R 4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
  • R 4 is selected from Ci-C6-halogenalkyl, phenyl-Ch , halogenphenyl-Chb, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted by substituents R 4b as defined below.
  • R 4 is selected from Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted bysubstituents R 4b as defined below. According to one embodiment thereof, the carbo- and heterocycle is unsubstituted.
  • R 4 is selected from substituted Ci-C6-hal- ogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted bysubstituents R 4b as de- fined below.
  • R 4 is selected from C2-C6-alkenyl, C2-C6-halo- genalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- C6-alkylaryl, six-membered heteroaryl or aryl which is unsubstituted or substituted by halogen or Ci-C6-halogenalkyl, and wherein the acyclic moieties of R 4 are unsubstituted or substituted with identical or different groups R 4a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R 4b as defined below.
  • R 4 is selected from CN, C2-C6-alkenyl, C2-C6- halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R 4 are unsubstituted or substituted with identical or different groups R 4a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R 4b as defined below.
  • R 4 is CN
  • R 4 is Ci-C6-alkylthio, such as SCH3, SC2H5, Sn-propyl, Si-propyl, Sn-butyl, Si-butyl, Stert-butyl, Sn-pentyl, Si-pentyl, CH2SCH3 or
  • R 4 is Ci-C6-halogenalkylthio, such as SCF 3 , According to still another embodiment of formula I, R 4 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
  • R 4 is Ci-C6-alkyl such as CH3. According to still another embodiment of formula I, R 4 is Ci-C6-alkyl such as C2H5. According to still another embodiment of formula I, R 4 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted by at least one group R 4a , which independently of one another are selected from:
  • N(C( 0)Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkylthio, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 - alkoxy, Ci-C 4 -halogenalkoxy, and S(0)n-Ci-C6-alkyl.
  • R 4 is CH3 is substituted by at least one group R 4a , which independently of one another are selected from:
  • N(C( 0)Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , C C 6 -alkylthio, Ci-C 4 -alkyl, C C 4 -halogenalkyl, Ci-C 4 - alkoxy, Ci-C 4 -halogenalkoxy, and S(0)n-Ci-C6-alkyl.
  • R 4 is C 2 Hs is substituted by at least one group R 4a , which independently of one another are selected from:
  • N(C( 0)Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkylthio, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, C1-C4- alkoxy, Ci-C 4 -halogenalkoxy, and S(0)n-Ci-C6-alkyl.
  • R 4 is CH 2 CN.
  • R 4 is CH 2 OH.
  • R 4 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, more specifically Ci-C 2 -halogenalkyl, such as CF3, CCI3, FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
  • R 4 is C 2 -C6-alkynyl or C 2 -C6-halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as C CH, C C-CI, CH 2 - C ⁇ CH, CH 2 -C ⁇ CCI or CH 2 - C ⁇ C-CH 3 .
  • R 4 is C 2 -C6-cycloalkynyl in particular C 2 -C 4 - cycloalkynyl, such as C C-cPr.
  • R 4 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C 2 -alkoxy such as OCH3, CH 2 CH3 or CH 2 OCH3.
  • R 4 is Ci-C6-alkyl-Ci-C6-alkoxy, in particular Ci-C 4 -alkyl-Ci-C 4 -alkoxy, more specifically Ci-C 2 -alkyl-Ci-C 2 -alkoxy, such as
  • R 4 is Ci-C6-halogenalkoxy, in particular Ci-C 4 -halogenalkoxy, more specifically Ci-C 2 -halogenalkoxy such as OCF3, OCHF 2 , OCH 2 F, OCCI3, OCHCI 2 or OCH 2 CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 4 is Ci-C6-alkyl-Ci-C6-halogenalkoxy, in particular Ci-C 4 -alkyl-Ci-C 4 -halogenalkoxy, more specifically Ci-C 2 -alkyl-Ci-C 2 -halogenalkoxy such as CH 2 OCF 3 , CH 2 OCHF 2 , CH 2 OCH 2 F, CH 2 OCCI 3 , CH 2 OCHCI 2 or CH 2 OCH 2 CI, in particular CH 2 OCF 3 , CH 2 OCHF 2 , CH 2 OCCI 3 or CH 2 OCHCI 2 .
  • R 4 is Ci-C6-alkyl-NH(Ci-C 4 -alkyl) or Ci- C6-alkyl-N(Ci-C 4 -alkyl) 2 , wherein alkyl is CH 3 , C 2 H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
  • R 4 is Ci-C6-alkyl-S(0) n -CrC 6 -alkyl, wherein alkyl is CH 3 , C 2 H 5 , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1 , 2 or 3.
  • R 4 is Ci-C6-alkyl-S(0) n -Ci-C6- halogenalkyl, wherein halogenalkyl is CF 3 or CHF 2 and n is 1 , 2 or 3.
  • R 4 is Ci-C6-alkyl-S(0) n -aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R 4b which independently of one another are selected from halogen, Ci-C 2 -alkyl, Ci-C 2 -alkoxy, Ci-C 2 -halogenalkyl, Ci-C 2 -halogenalkoxy and S(0) n -Ci-C6-alkyl, in particular F, CI, Br, CH 3 , OCH 3 , CF 3 , CHF 2 , OCHF 2 , OCF 3 .
  • R 4 is unsubstituted phenyl.
  • R 4 is phenyl, that is substituted by one, two or three, in par- ticular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
  • R 4 is Ci-C6-alkyl-NH-S0 2 -R x wherein R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R x2 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, CrC 4 -halogenalkyl, Ci-C 4 -alkoxy, or CrC 4 -halogenalkoxy, such as CH 2 NHS0 2 CF 3 or
  • R 4 is selected from Ci-C6-alkyl which is substituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or sub- stituted by substituents R 4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
  • R 4 is selected from Ci-C6-alkyl, especially CH 2 which is substituted by a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I, it is substituted by R 4b . According to one embodiment, R 4 is selected from Ci-C6-alkyl, especially Chb which is substituted by a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I , it is substituted by R 4b .
  • R 4 is selected from Ci-C6-alkyl, especially with R optionally substituted CH 2 which is substituted by a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I , it is substituted by R 4b .
  • R 4 is selected from Ci-C6-alkyl, especially Chb which is substi- tuted by a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I , it is substituted by R 4b .
  • R 4 is Ci-C6-alkyl, especially Chb substituted by a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in par- ticular 1 heteroatom, from the group consisting of N, O and S, as ring members.
  • the heterocycle contains one O as heteroatom.
  • the formed heterocycle is oxetane.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • it is substituted by R 4b .
  • R 4 is Ci-C6-alkyl, especially Chb substituted by a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members.
  • the heterocycle contains one O as heteroatom.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • it is substituted by R 4b .
  • R 4 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4b it is substituted by R 4b .
  • said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O.
  • the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • it is substituted by R 4b .
  • R 4 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted by substituents R 4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
  • R 4 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R 4b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
  • R 4 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R 4b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
  • R 4 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-mem- bered, wherein the carbocycle is unsubstituted or substituted by substituents R 4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
  • R 4 is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I, it is substituted by R 4b .
  • R 4 is a 3-membered saturated carbocycle, which is
  • R 4 is a 3-membered saturated carbocycle, which is substituted by halogen, more specifically by F, such as C3H3F2.
  • R 4 is a 3-membered saturated carbocycle, which is substituted by halogen. More specifically by CI, such as C3H3CI2.
  • R 4 is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I, it is substituted by R 4b .
  • R 4 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I, it is substituted by R 4b .
  • R 4 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I, it is substituted by R 4b .
  • R 4 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R 4b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
  • R 4 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-mem- bered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R 4b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
  • the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
  • R 4 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members.
  • the heterocycle contains one O as heteroatom.
  • the formed heterocycle is oxetane.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I, it is substituted by R 4b .
  • R 4 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members.
  • the heterocycle contains one O as heteroatom.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • it is substituted by R 4 .
  • R 4 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4b it is substituted by R 4b .
  • said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O.
  • the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • it is substituted by R 4b .
  • R 4 is phenyl-Ci-C6-alkyl, such as phenyl- CH 2 , wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R 4b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) n -Ci-C6-alkyl, in particular from CN, F, CI, Br, CH 3 , OCH 3 , CF 3 , CHF 2 , OCHF 2 , OCF 3 and S(0) 2 CH 3 .
  • R 4 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R 4b which independently of one another are selected from from CN, halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) n -Ci-C6-alkyl, in particular from CN, F, CI, Br, CH 3 , OCH 3 , CF 3 , CHF 2 , OCHF 2 , OCF 3 .
  • R 4 is unsubstituted phenyl.
  • R 4 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
  • R 4 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-4-yl, iso
  • R 4 is a 6-membered heteroaryl, such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • R 4 Particularly preferred embodiments of R 4 according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-129 corresponds to one particular embodiment of the invention, wherein P4-1 to P4-129 are also in any combination with one another a preferred embodiment of the present invention.
  • the connection point to the carbon atom, to which R 4 is bound is marked with "#" in the drawings.
  • R 3 , R 4 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, wherein the heteroatom N may carry one substituent selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from CN, Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or SO2, and wherein the carbocycle or heterocycle is unsubstituted or carries one, two
  • R 3 and R 4 form a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I, it is substituted by R 4b . According to one embodiment, R 3 and R 4 form a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b . According to still another embodiment of formula I, it is substituted by R 4b .
  • R 3 and R 4 form a 5-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4b it is substituted by R 4b .
  • R 3 and R 4 form a 6-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4b it is substituted by R 4b .
  • R 3 and R 4 form a 7-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4b it is substituted by R 4b .
  • R 3 and R 4 form a 3-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4b it is substituted by R 4b .
  • R 3 and R 4 form a 4-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4b it is substituted by R 4b .
  • R 3 and R 4 form a 5-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4b it is substituted by R 4b .
  • R 3 and R 4 form a 6-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4b it is substituted by R 4b .
  • R 3 and R 4 form a 7-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4b .
  • R 4 is substituted by R 4 .
  • R 4a is in each case independently selected from C1-C6- alkylthio, Ci-C 6 -halogenalkylthio, S(0) n -Ci-C 6 -alkyl, S(0) n -aryl, such as SCH 3 , S0 2 CH 3 , S0 2 Ph.
  • R 4a is in each case independently selected from NH(CrC 4 -alkyl), N(C C 4 -alkyl) 2 , NH-S0 2 -R*, such as NH(CH 3 ), N(CH 3 ) 2 or NHS0 2 CH 3 , NHS0 2 CF 3 .
  • R 4a is in each case independently selected from C 3 -C6- cycloalkyl, C 3 -C6-halogencycloalkyl, such as cyclopropyl or fully or partially halogenated cyclo- propyl.
  • R 4a is in each case independently selected from C1-C6- alkoxy, Ci-C 6 -halogenalkoxy, such as OCF 3 , OCHF 2 , OCH 2 F, OCCI 3 , OCHCI 2 or OCH 2 CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 4a is in each case independently selected from aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH 3 , CHF 2 , OCH 3 , OCHFs, CN or S0 2 CH 3 .
  • R 4a is in each case independently selected from halogen, OH, CN, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl and heterocycle, wherein the heretocyclocycle is a satureated and contains one N as a ring member.
  • R 4a is in each case independently selected from halogen, OH, CN, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, phenyl and aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH 3 , CHF 2 , OCH 3 , OCHF 3 , CN or S0 2 CH 3 .
  • R 4a is in each case independently selected from halogen, phenyl and halogenphenyl, wherein the halogenphenyl is substituted by halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
  • R 4a is in each case independently selected from halogen, CN, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C 4 -halogenalkoxy, Ci- C6-alkylthio, Ci-C6-halogenalkylthio, phenyl, wherein the phenyl is substituted by halogen selected from the group consisting of F, CI and Br or by Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy.
  • R 4a is in each case independently selected from halogen and phenyl wherein the phenyl is substituted by hal- ogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
  • R 4b is in each case independently selected from halo- gen, OH, CN, SH, Ci-C 6 -alkyl, Ci-C 6 -halogenalkyl, CrC 6 -alkoxy, CrC 6 -halogenalkoxy, CrC 6 - alkylthio and S(0) n -Ci-C6-alkyl.
  • R 4b is in each case independently selected from halogen, Ci-C6-alkoxy, Ci-C6-halogenalkyl, Ci-C6-halogen- alkoxy and S(0) n -Ci-C6-alkyl.
  • R 4b is in each case independently selected from Ci-C6-alkyl, such as methyl and ethyl. According to one fur- ther particular embodiment, R 4b is in each case independently selected from halogen, such as F, CI and Br. According to one further particular embodiment, R 4b is in each case independently selected from Ci-C6-alkoxy, such as OCH 3 . According to one further particular embodiment, R 4b is in each case independently selected from Ci-C4-halogenalkoxy, such as OCHF 2 and OCF 3 . According to one further particular embodiment, R 4b is in each case independently selected from S(0) n -Ci-C 6 -alkyl. such as S0 2 CH 3 .
  • R 5 is H.
  • R 6 is H.
  • A is selected from below group:
  • A is a
  • A is a
  • A is a
  • Y is H.
  • halogen OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the het- eroaryl, phenyl and phenoxy group is unsubstituted or substituted by R 78aa selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
  • R 78 wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R 78 are unsubstituted or substituted by R 78b which independently of one another are selected from:
  • R 78b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio.
  • o is 1.
  • o is 2 or 3. According to one specific embodiment thereof, o is 2. According to still another embodiment of formula I, o is 3.
  • R 78 is selected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy.
  • R 78 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
  • R 78 is F.
  • R 78 is CI.
  • R 78 is Br.
  • R 78 is OH .
  • R 78 is CN.
  • R 78 is NO2.
  • R 78 is SH.
  • R 78 is NH2.
  • R 78 is , NH(Ci-C4-alkyl), in particular
  • R 78 is , N(Ci-C4-alkyl)2, in particular
  • R 78 is NH-S02-R X such as NH-SO2-CH3, NH-SO2-CH2-CH3, NH-SO2-CF3 or NH-SOz-Ts.
  • R 78 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH 3 . or C2H5, in particular CH 3 .
  • R 78 is CH 2 CH 3 .
  • R 78 is CrC6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH2, F 2 CH, CI2CH, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
  • R 78 is C 2 -C6-alkynyl or C 2 -C6-halogen- alkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2- C CH, C ⁇ CCI, CH 2 - C ⁇ CCI, or CCI2- C ⁇ CCI.
  • R 78 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH 3 or OCH2CH 3 .
  • R 78 is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF 3 , OCHF2, OCH2F, OCCIs, OCHCI2 or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 78 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH, OChbC CH.
  • R 78 is C 3 -C6-cycloalkyl, in particular cyclopro- pyl.
  • R 78 is C 3 -C6-halogencycloalkyl.
  • R 1 is fully or partially halogenated cyclopropyl.
  • R 78 is C3-C6-cycloalkyl, such as a 4-membered saturated carbo- cycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 78b .
  • it is substituted by
  • R 78 is C3-C6-cycloalkyl, such as a 5-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 78b .
  • it is substituted by
  • R 78 is a C3-C6-cycloalkyl, such as 6-membered saturated carbo- cycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 78b . According to still another embodiment of formula I, it is substituted by
  • R 78 is C3-C6-cycloalkenyl, in particular cyclo- propenyl.
  • R 78 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R 78b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
  • R 78 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R 78b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
  • the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
  • R 78 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members.
  • the heterocycle contains one O as heteroatom.
  • the formed heterocycle is oxetane.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 78b . According to still another embodiment of formula I, it is substituted by R 78b .
  • R 78 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members.
  • the heterocycle contains one O as heteroa- torn.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 78b .
  • it is substituted by R 78b.
  • R 78 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 78b .
  • it is substituted by R 78b .
  • said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O.
  • the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R 78b .
  • R 78 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R 78b which independently of one another are selected from halogen, OH, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br, CH3, OCH3, CHF2, CF 3 OCHF 2 , and OCF 3 .
  • R 78 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R78b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, CHF2, OCH3, OCHF2, CF3 and OCF3.
  • R 78 is unsubstituted phenyl.
  • R 78 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
  • R 78 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isox
  • R 78 is a 6-membered heteroaryl, such as pyr- idin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • R 78 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3- C6-alkynyloxy, C3-C6-cycloalkyl, three-, four-, five- or six-membered saturated or partially un- saturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the carbo- and heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R 78 are unsubstituted or substituted with identical or different groups R 78a as defined and preferably defined herein, and wherein the heterocyclic, alicyclic, phenyl and heteroaryl moieties of R 78 are unsubstituted or substituted with identical
  • R 78 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R 78 are unsubstituted or substituted with identical or different groups R 78a as defined and preferably defined herein, and wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R 78 are unsubstit
  • the acyclic and cyclic moieties of R 78 are unsubstituted, according to another embodiment, the acyclic moieties of R 78 substituted with identical or different groups R 78a as defined and preferably defined herein.
  • R 78 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3- C6-alkynyloxy and C3-C6-cycloalkyl, wherein the acyclic moieties of R 78 are unsubstituted or substituted with identical or different groups R 78a as defined and preferably defined herein, and wherein the cycloalkyl moieties of R 78 are unsubstituted or substituted with identical or different groups R 78b as defined and preferably defined herein.
  • R 78 is in each case independently selected from halogen, Ci-C6-alkyl and Ci-C6-alkoxy, wherein the acyclic moieties of R 78 are unsubstituted or substituted with identical or different groups R 78a defined and preferably defined herein.
  • R 78 is in each case independently selected from halogen, Ci-C6-alkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, wherein the acyclic moieties of R 78 are unsubstituted or substituted with identical or different groups R 78a defined and preferably defined herein.
  • the acyclic and cyclic moieties of R 78 are not further substituted, according to another embodiment, the acyclic moieties of R 78 carry one, two, three or four identical or different groups R 78a as defined and preferably defined herein.
  • R 78a are the possible substituents for the acyclic moieties of R 78 .
  • R 78a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogengenalkoxy, Ci-C6-alkylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R 78a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy.
  • R 78a is in each case independently selected from Ci- Ce-alkoxy, Ci-C 6 -halogenalkoxy, such as OCF 3 , OCHF 2 , OCH 2 F, OCCI 3 , OCHC or OCH 2 CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 78a is in each case independently selected from C3- C6-cycloalkyl, C 3 -C6-halogencycloalkyl, such as cyclopropyl or fully or partially halogenated cy- clopropyl.
  • R 78a is a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyra- zol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxa- zol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4- yl, thiazol-5-yl, isothiazol-3-yl,
  • R 78a is a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • R 78a is in each case independently selected from aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH3, CHF 2 , OCH3, OCHF3, CN or SO2CH3.
  • R 78a is independently selected from halogen, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy.
  • R 78a is independently selected from CN, F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl , 1 ,1 -F 2 -cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
  • R 78a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
  • R 78b are the possible substituents for the C3-C6-cycloalkyl, heterocyclyl, heteroaryl and phenyl moieties of R 78 .
  • R 78b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy and Ci-C6-alkylthio.
  • R 78b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy.
  • R 78b is independently selected from F, CI, CN, CH 3 , OCH 3 and halogenmethoxy.
  • Particularly preferred embodiments of the A ring, optionally substituted by (R 78 ) 0 , according to the invention are in Table P78 below, wherein each line of lines P78-1 to P78-40corresponds to one particular embodiment of the invention, wherein P78-1 to P78-40 are also in any combination with one another a preferred embodiment of the present invention.
  • the positions of the pheny marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I:
  • P78-13 r-ocFs P78-40 3 ' -CN R 9 is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H2, N H(Ci- C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , N H (C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkenyl) 2 , N H(C 2 -C 4 -alkynyl), N(C 2 -C 4 -al- kynyl) 2 , N H(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , N(C2-C 4 -alkyl)(C 2 -C 4 -alkenyl), N(C 2 -C 4 -al- kyl)(C 2 -C 4 -alkynyl), N(C2-C 4 -
  • heteroaryl contains one, two or three heteroatoms selected from N , O and S;
  • R x is as defined above;
  • R Y is CrC 6 -alkyl, CrC 6 -halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl;
  • R 9 wherein the acyclic moieties of R 9 are unsubstituted or substituted by groups R 9a which independently of one another are selected from:
  • R 9a halogen, OH , CN , Ci-Ce-alkoxy, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, Ci- C 4 -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is un- substituted or substituted by substituents R 91 a selected from the group consisting of halogen, OH , Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halo- genalkoxy;
  • R 9b which independently of one another are selected from: R 9b halogen, OH , CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cyclo- alkyl, C 3 -C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio;
  • R 9 is selected from the group consisting of H , halogen, CN , Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C 3 -C6-cycloalkyl, C 3 -C6-halogency- cloalkyl, and OR Y .
  • R 9 is H .
  • R 9 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
  • R 9 is F.
  • R 9 is CI.
  • R 9 is Br.
  • R 9 is OH .
  • R 9 is CN .
  • R 9 is NO2. According to still another embodiment of formula I, R 9 is SH.
  • R 9 is NH2.
  • R 9 is , NH(Ci-C4-alkyl), in particular NH(CH3), NH(C 2 H 5 ).
  • R 9 is , N(Ci-C4-alkyl)2, in particular NH(CH3)2, NH(C 2 H 5 ) 2 .
  • R 9 is , NH(C3-C6-cycloalkyl), in particular NH(C 3 H 7 ), NH(C 4 H 9 ).
  • R 9 is , N(C3-C6-cycloalkyl)2, in particular N(C 3 H 7 ) 2 , N(C 4 H 9 ) 2 .
  • R 9 is N(Ci-C4-alkyl)(C2-C4-alkynyl), in particular N(CH 3 )(C ⁇ CH), N(CH 3 )(CH 2 C ⁇ CH), N(C 2 H 5 )(C ⁇ CH), N(C 2 H 5 )(CH 2 C ⁇ CH).
  • R 9 is N(CrC4-alkyl)(C 3 -C6-cycloalkyl), in particular N(CH 3 )(C 3 H 7 ), N(CH3)(C 4 H 9 ), N(C 2 H5)(C 3 H 7 ), N(CH 3 )(C 4 H 9 ).
  • R 9 is N(C2-C4-alkynyl)(C 3 -C6-cycloalkyl), in particular N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ), N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ).
  • R 9 is NH-S02-R X such as NH-SO2-CH3, NH-SO2-CH2-CH3, NH-SO2-CF3, NH-SO2-TS.
  • R 9 is S(0)n-C2-C6-alkenyl such as
  • R 9 is Ci-C6-alkyl, in particular Ci-C 4 -alkyl, such as CH3. or C 2 H5, in particular CH3 or CH 2 CH3.
  • R 9 is Ci-C6-halogenalkyl, in particular Ci-C 4 - halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
  • R 9 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, Ch C CH, C CCI,
  • R 9 is OR Y wherein R Y is Ci-C6-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl.
  • R 9 is OR Y , wherein R Y is Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically Ci-C2-alkoxy. R 9 is such as OCH3 or OCH2CH3.
  • R 9 is OR Y , wherein R Y is Ci-C6-halogen- alkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl.
  • R 9 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 9 is OR Y wherein R Y C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl.
  • R 9 is OR Y , wherein R Y C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl.
  • R 9 is such as OC ⁇ CH, OC ⁇ CCI, OCH 2 C ⁇ CCI, or OCCI 2 C ⁇ CCI.
  • R 9 is OR Y , wherein R Y is C3-C6-cycloalkyl, in particular cyclopropyl.
  • R 9 is OR Y wherein R Y is C3-C6-halogencyclo- alkyl.
  • R 1 is fully or partially halogenated cyclopropyl.
  • R 9 is is OR Y , wherein R Y C3-C6-cycloalkenyl, in particular cyclopropenyl.
  • R 9 is C3-C6-cycloalkyl, in particular cyclopropyl.
  • R 9 is C3-C6-halogencycloalkyl.
  • R 9b is fully or partially halogenated cyclopropyl, such as 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F 2 -cyclopropyl, 1 , 1 -Cl2-cyclopropyl .
  • R 9 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R 9b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R 9 is unsubstituted phenyl.
  • R 9 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
  • R 9 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-4-yl, iso
  • R 9 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • R 9 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R 9 are unsubstituted or substituted with iden- tical or different groups R 9a as defined and preferably defined herein, and wherein the carbocy-rod, phenyl and heteroaryl moieties of R 9 are unsubstituted or substituted with identical or different groups R 9b as defined and preferably defined herein.
  • R 9 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R 9 are unsubstituted or substituted with identical or different groups R 9a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R 9 are unsubstituted or substituted with identical or different groups R 9b as defined and preferably defined herein.
  • R 9a are the possible substituents for the acyclic moieties of R 9 .
  • R 9a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R 91a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.
  • R 9a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy.
  • R 9a is independently selected from F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1 -F2- cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
  • R 9a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
  • R 9b are the possible substituents for the cycloalkyi, heteroaryl and phenyl moieties of R 9 .
  • R 9b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
  • R 9b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy.
  • R 9b is independently selected from F, CI, CN , CH3, OCH3 and halogenmethoxy.
  • R 9 Particularly preferred embodiments of R 9 according to the invention are in Table P13 below, wherein each line of lines P13-1 to P3-43 corresponds to one particular embodiment of the invention, wherein P13-1 to P3-43 are also in any combination with one another a preferred embodiment of the present invention.
  • the connection point to the carbon atom, to which R 9 is bound is marked with "#" in the drawings.
  • R 10 is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H 2 , N H(Ci- C 4 -alkyl), N(CrC 4 -alkyl) 2 , N H (C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkenyl) 2 , N H(C 2 -C 4 -alkynyl), N(C 2 -C 4 -al- kynyl) 2 , N H(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , N(C 2 -C 4 -alkyl)(C 2 -C 4 -alkenyl), N(C 2 -C 4 -al- kyl)(C 2 -C 4 -alkynyl), N(C 2 -C 4 -alkynyl)(C 2 -C 4
  • heteroaryl contains one, two or three heteroatoms selected from N , O and S;
  • R x is as defined above;
  • R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6- alkynyl, C 2 -C6-halogenalkynyl, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl;
  • R 10 wherein the acyclic moieties of R 10 are unsubstituted or substituted by groups R 10a which independently of one another are selected from:
  • R 10a halogen, OH , CN , Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C C 4 -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R 101 a selected from the group consisting of halogen, OH , Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halo- genalkoxy;
  • groups R 10b which independently of one another are selected from:
  • R 10b halogen, OH , CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, C C 4 -halogenalkyl, C 3 -C 6 -cyclo- alkyl, C 3 -C6-halogencycloalkyl, CrC 4 -halogenalkoxy and Ci-C6-alkylthio.
  • R 10 is in each case independently selected from halogen, OH , CN , N0 2 , SH , N H 2 , N H(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , N H(C 2 -C 4 -alkenyl), N(C 2 -C 4 - alkenyl) 2 , N H(C 2 -C 4 -alkynyl), N(C 2 -C 4 -alkynyl) 2 , N H(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , N(C 2 -C 4 -alkyl)(C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkyl)(C 2 -C 4 -alkynyl), N(C 2 -C 4 -alkyl)(C 3 -C 3 -C 3 -
  • R x is as defined above;
  • R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6- alkynyl, C 2 -C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl;
  • R 10 wherein the acyclic moieties of R 10 are unsubstituted or substituted by groups R 10a which independently of one another are selected from:
  • R 10a halogen, OH, CN, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, Ci-
  • groups R 10b which independently of one another are selected from:
  • R 10b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cyclo- alkyl, C 3 -C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
  • R 10 is secected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C 2 - C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6-alkynyl, C 2 -C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-hal ogenalkoxy and OR Y .
  • R 10 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
  • R 10 is F.
  • R 10 is CI.
  • R 10 is Br.
  • R 10 is OH.
  • R 10 is CN.
  • R 10 is N0 2 .
  • R 10 is SH.
  • R 10 is NH 2 .
  • R 10 is , NH(C
  • R 10 is , N(Ci-
  • R 10 is , N(C 2 -C4--alkenyl) 2 , in particular
  • R 10 is , NH(C 2 -C4-alkynyl), in particular NH(C ⁇ CH), NH(CH 2 C ⁇ CH).
  • R 10 is , NH(C 3 -C6-cycloalkyl), in particular NH(C 3 H 7 ), NH(C 4 H 9 ).
  • R 10 is , N(C 3 -C6-cycloalkyl) 2 , in particular N(C 3 H 7 ) 2 , N(C 4 H 9 ) 2 .
  • R 10 is N(Ci-C4-alkyl)(C 2 -C4-alkynyl), in particular N(CH 3 )(C ⁇ CH), N(CH 3 )(CH 2 C ⁇ CH), N(C 2 H 5 )(C ⁇ CH), N(C 2 H 5 )(CH 2 C ⁇ CH).
  • R 10 is N(Ci-C4-alkyl)(C 3 -C6-cycloalkyl), in particular N(CH 3 )(C 3 H 7 ), N(CH 3 )(C 4 H 9 ), N(C 2 H 5 )(C 3 H 7 ), N(CH 3 )(C 4 H 9 ).
  • R 10 is N(C 2 -C4-alkynyl)(C 3 -C6-cycloalkyl), in particular N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ), N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ).
  • R 10 is NH-S0 2 -R x such as NH-S0 2 - CH 3 , NH-S0 2 -CH 2 -CH 3 , NH-S0 2 -CF 3 , NH-S0 2 -Ts.
  • R 10 is S(0)n-C 2 -C6-alkenyl such as
  • R 10 is Ci-C6-alkyl, in particular Ci-C 4 -alkyl, such as CH3. or C 2 H5, in particular CH3 or CH 2 CH3.
  • R 10 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
  • R 10 is C 2 -C6-alkynyl or C 2 -C6-halogen- alkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as C CH, CH 2 C CH, C CCI, CH 2 C ⁇ CCI, or CCI 2 C ⁇ CCI.
  • R 10 is OR Y wherein R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6-al kynyl, C 2 -C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl.
  • R 10 is OR Y , wherein R Y is Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically Ci-C2-alkoxy.
  • R 10 is such as OCH3 or OCH2CH3.
  • R 10 is OR Y , wherein R Y is Ci-C6-halo- genalkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl.
  • R 10 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI2.
  • R 10 is OR Y , wherein R Y C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl.
  • R 10 is OR Y , wherein R Y C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl.
  • R 10 is such as OC ⁇ CH, OC ⁇ CCI, OCH 2 C ⁇ CCI, or OCCI 2 C ⁇ CCI
  • R 10 is OR Y wherein R Y is C3-C6-cycloalkyl, in particular cyclopropyl.
  • R 10 is OR Y , wherein R Y is C3-C6-halogency- cloalkyl.
  • R 1 is fully or partially halogenated cyclopropyl.
  • R 10 is is OR Y , wherein R Y C3-C6-cycloalkenyl, in particular cyclopropenyl.
  • R 10 is C3-C6-cycloalkyl, in particular cyclopropyl.
  • R 10 is C3-C6-halogencycloalkyl.
  • R 10b is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl
  • R 10 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R 10b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF 3 and OCF 3 .
  • R 10 is unsubstituted phenyl.
  • R 10 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
  • R 10 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isoxa
  • R 9 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • R 10 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy,C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R 10 are unsubstituted or substituted with identical or different groups R 10a as defined and preferably defined herein, and wherein the carbocy-rod, phenyl and heteroaryl moieties of R 10 are unsubstituted or substituted with identical or dif- ferent groups R 10b as defined and preferably defined herein.
  • R 10 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R 10 are unsubstituted or substituted with iden- tical or different groups R 10a as defined and preferably defined herein, and wherein the cycloal- kyl moieties of R 10 are unsubstituted or substituted with identical or different groups R 10b as defined and preferably defined herein.
  • R 10a are the possible substituents for the acyclic moieties of R 9 .
  • R 10a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R 91a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.
  • R 10a is independently selected from halogen, Ci-C6-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R 10a is
  • R 10a is independently halogen, in particular selected from F, CI, Br and I , more specifically F, CI and Br.
  • R 10b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R 10 .
  • R 10b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
  • R 10b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy.
  • R 10b is independently selected from F, CI, CN, CH 3 , OCH 3 and halogenmethoxy.
  • R 10 Particularly preferred embodiments of R 10 according to the invention are in Table P14 below, wherein each line of lines P14-1 to P14-43 corresponds to one particular embodiment of the in- vention, wherein P14-1 to P14-43 are also in any combination with one another a preferred embodiment of the present invention.
  • the connection point to the carbon atom, to which R 10 is bound is marked with "#" in the drawings.
  • R N is the substituent of the heteroatom N that is contained in the heterocycle formed by R 9 and R 10 in some of the inventive compounds.
  • R N is selected from Ci-C4-alkyl, Ci-C4-halogen- alkyl and SC>2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from Ci-C4-alkyl.
  • R N is in each case independently selected from Ci-C2-alkyl, Ci-C2-halogenalkyl and SC>2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl substituents.
  • R N is in each case independently selected from Ci-C2-alkyl, more particularly methyl. In one particular embodiment, R N is in each case independently selected from S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl.
  • R 9 and R 10 together with the carbon atoms to which they are bound form a saturated or partially unsaturated five-, six-or seven -membered carbo- and heterocycle that is unsubstituted or substituted.
  • R 9 and R 10 form a 3-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 9 and R 10 form a 4-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 9 and R 10 form a 5-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 9 and R 10 form a 6-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 9 and R 10 form a 7-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 9 and R 10 form a 3-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 9 and R 10 form a 4-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 9 and R 10 form a 5-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • it is substituted by R 11 .
  • R 9 and R 10 form a 6-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 9 and R 10 form a 7-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 9 and R 10 form a 5-membered saturated heteroaryl.
  • the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 9 and R 10 form a 6-membered heteroaryl.
  • the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 11 .
  • R 11 it is substituted by R 11 .
  • R 11 is in each case independently selected from halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - alkynyl, Ci-C6-alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
  • R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R x11 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
  • R 11 wherein the acyclic moieties of R 11 are unsubstituted or substituted with identical or different groups R 11a which independently of one another are selected from:
  • R 11a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci-C 4 -halo- genalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 111a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkoxy, CN, C3-C6-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci-C 4 -alkylthio;
  • R 11 wherein the carbocyclic, heterocyclic, heteroaryl and aryl of R 11 are unsubstituted or substituted with identical or different groups R 11b which independently of one another are selected from:
  • R 11b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
  • m is 1 .
  • m is 2 or 3. According to one specific embodiment thereof, m is 2. According to still another embodiment of formula I, m is 3.
  • R 11 is halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci- Ce-alkoxy or , C C 6 -halogenalkoxy, in particular CH 3 , Et, CHF 2 , OCH 3 , OCHF 2 , OCF 3 , F, CI, more specifically H, CH 3 , F or CI most preferred F or CI.
  • R 11 is halogen, in particular Br, F or CI, more specifically F or CI.
  • R 11 is OH.
  • R 11 is CN
  • R 11 is Nhb, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-R X , wherein R x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R x11 independently selected from Ci-C4-al- kyl.
  • R 11 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH 3 .
  • R 11 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI2 or CH 2 CI.
  • R 11 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as C ⁇ CH, CH 2 C ⁇ CH, C ⁇ C-CI, C ⁇ C- CH 3 , CH 2 C ⁇ CH, CH 2 C ⁇ CCI or CH 2 C ⁇ C-CH 3 .
  • R 11 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH 3 or OCH2CH 3 .
  • R 11 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCI 3 , OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 11 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
  • R 11 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R 11b as defined and preferably herein.
  • R 11 is C3-C6-halogencycloalkyl.
  • R 11 is fully or partially halogenated cyclopropyl.
  • R 11 is unsubstituted aryl or aryl that is substituted by one, two, three or four R 11b , as defined herein.
  • R 11 is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R 11 b , as defined herein.
  • R 11 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R 11 is 5- or 6-membered heteroaryl that is substituted by one, two or three R 11b , as defined herein.
  • R 11 is in each case independently selected from halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R 11 are not further substituted or carry one, two, three, four or five identical or different groups R 11a as defined below and wherein the carbocyclic, heterocyclic and heteroaryl moieties of R 11 are not further substituted or carry one, two, three, four or five identical or different groups R 11 b as defined below.
  • R 11 is independently selected from halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy.
  • R 11a are the possible substituents for the acyclic moieties of R 11 .
  • R 11a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 111a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, CrC 4 -halogenalkyl, CrC 4 -alkoxy, Ci-C 4 - halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -alkylthio.
  • R 11a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 111a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci- C 4 -halogenalkoxy, in particular selected from halogen, Ci-C 2 -alkyl, Ci-C 2 -halogenalkyl, Ci-C 2 - alkoxy, Ci-C 2 -halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
  • halogen such as F, CI and Br.
  • R 11a is independently selected from halogen, OH, CN, Ci-C 2 -alkoxy, C 3 - C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C 2 -halogenalkoxy. Specifically, R 11a is
  • R 11a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
  • R 11a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C 2 -halogenalkoxy. Specifically, R 11a is
  • R 11b are the possible substituents for the carbocyclic, heterocyclic and heteroaryl moieties of R 11 .
  • R 11 b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
  • R 11 b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalky and Ci-C2-hal- ogenalkoxy.
  • R 11 b is independently selected from F, CI, OH, CN, CH 3 , OCH 3 , cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 , 1 -F2-cyclopropyl, 1 , 1 -Cl2-cyclopropyl and halogenmethoxy.
  • R 11 b is independently selected from Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogen- alkoxy.
  • R 11 b is independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F- cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from OH, CH 3 , OCH 3 , cyclopropyl, 1 -F-cyclopropyl, 1 - Cl-cyclopropyl, 1 , 1 -F 2 -cyclopropyl, 1 , 1 -Cl2-cyclopropyl cyclopropyl and OCHF 2 .
  • Particular embodiments of the compounds I are the following compounds: 1-1.A, 1-1 .B, 1-1.C, I- 1.D, 1-1 . E, 1-1. F, 1-1 .G, 1-1.1; I-2.A, 1-2. B, I-2.C, 1-2. D, I-2.E, 1-2. F, I-2.G, 1-2.1; I-3.A, I-3.B, I-3.C, I- 3.D, 1-3. E, I-3.F, I-3.G, 1-3.1; I-4.A, 1-4. B, I-4.C, 1-4. D, I-4.E, 1-4. F, I-4.G, 1-4.1.
  • the substituents R 4 , R 9 and R 10 are independently as defined in claim 1 or preferably defined bel
  • Particular embodiments of the compounds I are the following compounds: 1-1.A, 1-1. B, 1-1. C, I- 1.D, 1-1 . E, 1-1 . F, 1-1. G, 1-1.1; I-2.A, I-2.B, I-2.C, I-2.D, I-2.E, I-2.F, I-2.G, 1-2.1; I-3.A, I-3.B, I-3.C, I- 3.D, I-3.E, I-3.F, I-3.G, 1-3.1; I-4.A, I-4.B, I-4.C, I-4.D, I-4.E, I-4.F, I-4.G, 1-4.1.
  • Tables 1-1 to 1 -8 that are compiled in the Tables 1-1 to 1 -8, Tables 2-1 to 2-8, Tables 3-1 to 3-8, Tables 4-1 to 4-8, Tables 5-1 to 5-8, Tables 6-1 to 6-8, Tables 7-1 to 7-8, Tables 8-1 to 8-8, Tables 9-1 to 9-8.
  • Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
  • Table 1-1 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R 9 is CH 3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -1.A-1 to 1-1 .A.1 -1.A-287, compounds I-2.A.1-
  • Table 1-2 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -2.A-1 to 1-1 .A.1 -2.A-287, compounds I-2.A.1-
  • Table 1-4 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R 9 is Br and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1 -4.A-1 to 1-1 .A.1-4.A-287, compounds I-2.A.1 -4.A-1 to I- 2.A.1-4.A-287, compounds I-3.A.1-4.A-1 to I-3.A.1 -4.A-287 compounds I-4.A.1-4.A-1 to I-4.A.1 - 4.A-287).
  • Table 1-5 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -5.A-1 to 1-1 .A.1 -5.A-287, compounds I-2.A.1- 5.A-1 to I-2.A.1 -5.A-287, compounds I-3.A.1-5.A-1 to I-3.A.1 -5.A-287 compounds I-4.A.1-5.A-1 to I-4.A.1-5.A-287).
  • Table 1-6 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1-6.A-1 to I-1.A.1 -6.A-287, compounds I- 2.A.1-6.A-1 to I-2.A.1-6.A-287, compounds I-3.A.1-6.A-1 to I-3.A.1-6.A-287 compounds I-4.A.1- 6.A-1 to I-4.A.1 -6.A-287).
  • Table 1-7 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R 9 is H and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1 -7.A-1 to 1-1 .A.1-7.A-287, compounds I-2.A.1 -7.A-1 to I- 2.A.1-7.A-287, compounds I-3.A.1-7.A-1 to I-3.A.1 -7.A-287 compounds I-4.A.1-7.A-1 to I-4.A.1 - 7.A-287).
  • Table 1-8 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R 9 is CF3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -8.A-1 to 1-1 .A.1 -8.A-287, compounds I-2.A.1- 8.A-1 to I-2.A.1 -8.A-287, compounds I-3.A.1-8.A-1 to I-3.A.1 -8.A-287 compounds I-4.A.1-8.A-1 to I-4.A.1-8.A-287).
  • Table 2-1 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R 9 is CH 3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-1.A-1 to 1-1 .B.2-1.A-287, compounds I-2.B.2- 1.A-1 to I-2.B.2-1.A-287, compounds I-3. B.2-1.A-1 to I-3.B.2-1 .A-287 compounds I-4. B.2-1.A-1 to I-4. B.2-1. A-287).
  • Table 2-2 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-2.A-1 to 1-1 .B.2-2.A-287, compounds I-2.B.2- 2.A-1 to I-2.B.2-2.A-287, compounds I-3.B.2-2.A-1 to I-3.B.2-2.A-287 compounds I-4.B.2-2.A-1 to I-4.B.2-2.A-287).
  • Table 2-3 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R 9 is C ⁇ CH and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-3.A-1 to 1-1 .B.2-3.A-287, compounds I-2.B.2- 3.A-1 to I-2.B.2-3.A-287, compounds I-3.B.2-3.A-1 to I-3.B.2-3.A-287 compounds I-4.B.2-3.A-1 to I-4.B.2-3.A-287).
  • Table 2-4 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R 9 is Br and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-4.A-1 to 1-1 .B.2-4.A-287, compounds I-2.B.2-4.A-1 to I- 2.B.2-4.A-287, compounds I-3.B.2-4.A-1 to I-3.B.2-4.A-287 compounds I-4.B.2-4.A-1 to I-4.B.2- 4.A-287).
  • Table 2-5 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-5.A-1 to 1-1 .B.2-5.A-287, compounds I-2.B.2- 5.A-1 to I-2.B.2-5.A-287, compounds I-3.B.2-5.A-1 to I-3.B.2-5.A-287 compounds I-4.B.2-5.A-1 to I-4.B.2-5.A-287).
  • Table 2-6 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-6.A-1 to 1-1.B.2-6.A-287, compounds I- 2.B.2-6.A-1 to I-2.B.2-6.A-287, compounds I-3.B.2-6.A-1 to I-3.B.2-6.A-287 compounds I-4.B.2- 6.A-1 to I-4.B.2-6.A-287).
  • Table 2-7 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R 9 is H and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-7.A-1 to I-1 .B.2-7.A-287, compounds I-2.B.2-7.A-1 to I- 2.B.2-7.A-287, compounds I-3.B.2-7.A-1 to I-3.B.2-7.A-287 compounds I-4.B.2-7.A-1 to I-4.B.2- 7.A-287).
  • Table 2-8 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R 9 is CF3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-8.A-1 to 1-1 .B.2-8.A-287, compounds I-2.B.2- 8.A-1 to I-2.B.2-8.A-287, compounds I-3.B.2-8.A-1 to I-3.B.2-8.A-287 compounds I-4.B.2-8.A-1 to I-4.B.2-8.A-287).
  • Table 3-1 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R 9 is CH 3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-1 .A-1 to 1-1.C.3-1.A-287, compounds I-2.C.3-
  • Table 3-2 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-2.A-1 to 1-1.C.3-2.A-287, compounds I-2.C.3-
  • Table 3-3 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R 9 is C ⁇ CH and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-3.A-1 to 1-1.C.3-3.A-287, compounds I-2.C.3- 3.A-1 to I-2.C.3-3.A-287, compounds I-3.C.3-3.A-1 to I-3.C.3-3.A-287 compounds I-4.C.3-3.A-1 to I-4.C.3-3.A-287).
  • Table 3-4 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R 9 is Br and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-4.A-1 to I-1.C.3-4.A-287, compounds I-2.C.3-4.A-1 to I- 2.C.3-4.A-287, compounds I-3.C.3-4.A-1 to I-3.C.3-4.A-287 compounds I-4.C.3-4.A-1 to I-4.C.3- 4.A-287).
  • Table 3-5 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-5.A-1 to 1-1.C.3-5.A-287, compounds I-2.C.3- 5.A-1 to I-2.C.3-5.A-287, compounds I-3.C.3-5.A-1 to I-3.C.3-5.A-287 compounds I-4.C.3-5.A-1 to I-4.C.3-5.A-287).
  • Table 3-6 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-6.A-1 to 1-1.C.3-6.A-287, compounds I- 2.C.3-6.A-1 to I-2.C.3-6.A-287, compounds I-3.C.3-6.A-1 to I-3.C.3-6.A-287 compounds I-4.C.3-
  • Table 3-7 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R 9 is H and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-7.A-1 to I-1.C.3-7.A-287, compounds I-2.C.3-7.A-1 to I- 2.C.3-7.A-287, compounds I-3.C.3-7.A-1 to I-3.C.3-7.A-287 compounds I-4.C.3-7.A-1 to I-4.C.3-
  • Table 3-8 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R 9 is CF3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-8.A-1 to 1-1.C.3-8.A-287, compounds I-2.C.3- 8.A-1 to I-2.C.3-8.A-287, compounds I-3.C.3-8.A-1 to I-3.C.3-8.A-287 compounds I-4.C.3-8.A-1 to I-4.C.3-8.A-287).
  • Table 4-1 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R 9 is CH 3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-1 .A-1 to 1-1.D.4-1.A-287, compounds I-2.D.4-
  • Table 4-2 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-2.A-1 to 1-1.D.4-2.A-287, compounds I-2.D.4-
  • Table 4-3 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R 9 is C ⁇ CH and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-3.A-1 to 1-1.D.4-3.A-287, compounds I-2.D.4- 3.A-1 to I-2.D.4-3.A-287, compounds I-3.D.4-3.A-1 to I-3.D.4-3.A-287 compounds I-4.D.4-3.A-1 to I-4.D.4-3.A-287).
  • Table 4-4 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R 9 is Br and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-4.A-1 to I-1.D.4-4.A-287, compounds I-2.D.4-4.A-1 to I- 2.D.4-4.A-287, compounds I-3.D.4-4.A-1 to I-3.D.4-4.A-287 compounds I-4.D.4-4.A-1 to I-4.D.4- 4.A-287).
  • Table 4-5 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-5.A-1 to 1-1.D.4-5.A-287, compounds I-2.D.4- 5.A-1 to I-2.D.4-5.A-287, compounds I-3.D.4-5.A-1 to I-3.D.4-5.A-287 compounds I-4.D.4-5.A-1 to I-4.D.4-5.A-287).
  • Table 4-6 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-6.A-1 to 1-1.D.4-6.A-287, compounds I- 2.D.4-6.A-1 to I-2.D.4-6.A-287, compounds I-3.D.4-6.A-1 to I-3.D.4-6.A-287 compounds I-4.D.4-
  • Table 4-7 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R 9 is H and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-7.A-1 to I-1.D.4-7.A-287, compounds I-2.D.4-7.A-1 to I- 2.D.4-7.A-287, compounds I-3.D.4-7.A-1 to I-3.D.4-7.A-287 compounds I-4.D.4-7.A-1 to I-4.D.4-
  • Table 4-8 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R 9 is CF3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-8.A-1 to 1-1.D.4-8.A-287, compounds I-2.D.4- 8.A-1 to I-2.D.4-8.A-287, compounds I-3.D.4-8.A-1 to I-3.D.4-8.A-287 compounds I-4.D.4-8.A-1 to I-4.D.4-8.A-287).
  • Table 5-1 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R 9 is CH 3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-1.A-1 to 1-1 .E.5-1.A-287, compounds I-2.E.5-
  • Table 5-2 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-2.A-1 to 1-1 .E.5-2.A-287, compounds I-2.E.5-
  • Table 5-3 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R 9 is C ⁇ CH and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-3.A-1 to 1-1 .E.5-3.A-287, compounds I-2.E.5- 3.A-1 to I-2.E.5-3.A-287, compounds I-3.E.5-3.A-1 to I-3.E.5-3.A-287 compounds I-4.E.5-3.A-1 to I-4.E.5-3.A-287).
  • Table 5-4 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R 9 is Br and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-4.A-1 to 1-1 .E.5-4.A-287, compounds I-2.E.5-4.A-1 to I- 2.E.5-4.A-287, compounds I-3.E.5-4.A-1 to I-3.E.5-4.A-287 compounds I-4.E.5-4.A-1 to I-4.E.5- 4.A-287).
  • Table 5-5 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-5.A-1 to 1-1 .E.5-5.A-287, compounds I-2.E.5- 5.A-1 to I-2.E.5-5.A-287, compounds I-3.E.5-5.A-1 to I-3.E.5-5.A-287 compounds I-4.E.5-5.A-1 to I-4.E.5-5.A-287).
  • Table 5-6 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-6.A-1 to 1-1.E.5-6.A-287, compounds I- 2.E.5-6.A-1 to I-2.E.5-6.A-287, compounds I-3.E.5-6.A-1 to I-3.E.5-6.A-287 compounds I-4.E.5-
  • Table 5-7 Compounds of the formula 1-1. E, I-2.E, I-3.E, I-4.E in which R 9 is H and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-7.A-1 to 1-1 .E.5-7.A-287, compounds I-2.E.5-7.A-1 to I- 2.E.5-7.A-287, compounds I-3.E.5-7.A-1 to I-3.E.5-7.A-287 compounds I-4.E.5-7.A-1 to I-4.E.5-
  • Table 5-8 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R 9 is CF3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-8.A-1 to 1-1 .E.5-8.A-287, compounds I-2.E.5- 8.A-1 to I-2.E.5-8.A-287, compounds I-3.E.5-8.A-1 to I-3.E.5-8.A-287 compounds I-4.E.5-8.A-1 to I-4.E.5-8.A-287).
  • Table 6-1 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R 9 is CH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1 .F.1-1.A-1 to I-1.F.1-1.A-287, compounds I-2.F.1-1 .A-1 to I- 2.F.1 -1 .A-287, compounds I-3.F.1-1.A-1 to I-3.F.1-1 .A-287 compounds I-4.F.1 -1 .A-1 to I-4.F.1 - 1.A-287).
  • Table 6-2 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-2.A-1 to 1-1 .F.1 -2.A-287, compounds I-2.F.1 - 2.A-1 to I-2.F.1-2.A-287, compounds I-3.F.1 -2.A-1 to I-3.F.1 -2.A-287 compounds I-4.F.1-2.A-1 to I-4.F.1 -2.A-287).
  • Table 6-3 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R 9 is C ⁇ CH and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-3.A-1 to 1-1 .F.1 -3.A-287, compounds I-2.F.1 - 3.A-1 to I-2.F.1-3.A-287, compounds I-3.F.1 -3.A-1 to I-3.F.1 -3.A-287 compounds I-4.F.1-3.A-1 to I-4.F.1 -3.A-287).
  • Table 6-4 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R 9 is Br and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .F.1-4.A-1 to I-1.F.1-4.A-287, compounds I-2.F.1-4.A-1 to I- 2.F.1 -4.A-287, compounds I-3.F.1-4.A-1 to I-3.F.1-4.A-287 compounds I-4.F.1 -4.A-1 to I-4.F.1 - 4.A-287).
  • Table 6-5 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-5.A-1 to 1-1 .F.1 -5.A-287, compounds I-2.F.1 - 5.A-1 to I-2.F.1-5.A-287, compounds I-3.F.1 -5.A-1 to I-3.F.1 -5.A-287 compounds I-4.F.1-5.A-1 to I-4.F.1 -5.A-287).
  • Table 6-6 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.F.1-6.A-1 to 1-1.F.1-6.A-287, compounds I- 2.F.1 -6.A-1 to I-2.F.1 -6.A-287, compounds I-3.F.1-6.A-1 to I-3.F.1-6.A-287 compounds I-4.F.1 - 6.A-1 to I-4.F.1-6.A-287).
  • Table 6-7 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R 9 is H and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-7.A-1 to I-1.F.1-7.A-287, compounds I-2.F.1 -7.A-1 to I-2.F.1 - 7.A-287, compounds I-3.F.1 -7.A-1 to I-3.F.1 -7.A-287 compounds I-4.F.1-7.A-1 to I-4.F.1-7.A- 287).
  • Table 6-8 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R 9 is CF3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .F.1-8.A-1 to I-1.F.1-8.A-287, compounds I-2.F.1-8.A-1 to I- 2.F.1 -8.A-287, compounds I-3.F.1-8.A-1 to I-3.F.1-8.A-287 compounds I-4.F.1 -8.A-1 to I-4.F.1 - 8.A-287).
  • Table 7-1 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R 9 is CH 3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-1.A-1 to 1-1 .G.7-1.A-287, compounds I-2.G.7-
  • Table 7-2 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-2.A-1 to 1-1 .G.7-2.A-287, compounds I-2.G.7-
  • Table 7-4 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R 9 is Br and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .G.7-4.A-1 to I-1.G.7-4.A-287, compounds I-2.G.7-4.A-1 to I- 2.G.7-4.A-287, compounds I-3.G.7-4.A-1 to I-3.G.7-4.A-287 compounds I-4.G.7-4.A-1 to I-
  • Table 7-5 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-5.A-1 to 1-1 .G.7-5.A-287, compounds I-2.G.7-
  • Table 7-6 Compounds of the formula 1-1. G, I-2.G, I-3.G, I-4.G in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .G.7-6.A-1 to 1-1.G.7-6.A-287, compounds I- 2.G.7-6.A-1 to I-2.G.7-6.A-287, compounds I-3.G.7-6.A-1 to I-3.G.7-6.A-287 compounds I- 4.G.7-6.A-1 to I-4.G.7-6.A-287).
  • Table 7-7 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R 9 is H and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .G.7-7.A-1 to I-1.G.7-7.A-287, compounds I-2.G.7-7.A-1 to I- 2.G.7-7.A-287, compounds I-3.G.7-7.A-1 to I-3.G.7-7.A-287 compounds I-4.G.7-7.A-1 to I- 4.G.7-7.A-287).
  • Table 7-8 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R 9 is CF3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-8.A-1 to 1-1 .G.7-8.A-287, compounds I-2.G.7- 8.A-1 to I-2.G.7-8.A-287, compounds I-3.G.7-8.A-1 to I-3.G.7-8.A-287 compounds I-4.G.7-8.A-1 to I-4.G.7-8.A-287).
  • Table 8-1 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R 9 is CH 3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.H.8-1 .A-1 to 1-1.H.8-1.A-287, compounds I-2.H.8-
  • Table 8-2 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.H.8-2.A-1 to 1-1.H.8-2.A-287, compounds I-2.H.8-
  • Table 8-3 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R 9 is C ⁇ CH and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-3.A-1 to 1-1.H.8-3.A-287, compounds I-2.H.8-
  • Table 8-4 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R 9 is Br and the mean- ing for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-4.A-1 to I-1.H.8-4.A-287, compounds I-2.H.8-4.A-1 to I- 2.H.8-4.A-287, compounds I-3.H.8-4.A-1 to I-3.H.8-4.A-287 compounds I-4.H.8-4.A-1 to I-4.H.8-
  • Table 8-5 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-5.A-1 to 1-1.H.8-5.A-287, compounds I-2.H.8-
  • Table 8-6 Compounds of the formula 1-1. H, I-2.H, I-3.H, I-4.H in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-6.A-1 to 1-1.H.8-6.A-287, compounds I- 2.H.8-6.A-1 to I-2.H.8-6.A-287, compounds I-3.H.8-6.A-1 to I-3.H.8-6.A-287 compounds I-4.H.8-
  • Table 8-7 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R 9 is H and the mean- ing for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-7.A-1 to I-1.H.8-7.A-287, compounds I-2.H.8-7.A-1 to I- 2.H.8-7.A-287, compounds I-3.H.8-7.A-1 to I-3.H.8-7.A-287 compounds I-4.H.8-7.A-1 to I-4.H.8-
  • Table 8-8 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R 9 is CF3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-8.A-1 to 1-1.H.8-8.A-287, compounds I-2.H.8-
  • Table 9-1 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R 9 is CH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.1.9-1 .A-1 to 1-1.1.9-1 .A-287, compounds 1-2.1.9-1 .A-1 to I-2.I.9- 1.A-287, compounds 1-3.1.9-1. A-1 to 1-3.1.9-1 .A-287 compounds 1-4.1.9-1.A-1 to 1-4.1.9-1 .A-287).
  • Table 9-2 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .1.9-2.A-1 to 1-1.1.9-2.A-287, compounds I-2.I.9-2.A-1 to I- 2.I.9-2.A-287, compounds I-3.I.9-2.A-1 to I -3.1.9-2. A-287 compounds I-4.I.9-2.A-1 to I-4.I.9-2.A- 287).
  • Table 9-3 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R 9 is C ⁇ CH and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .1.9-3.A-1 to 1-1.1.9-3.A-287, compounds I-2.I.9-3.A-1 to I- 2.I.9-3.A-287, compounds I-3.I.9-3.A-1 to I-3.I.9-3.A-287 compounds I-4.I.9-3.A-1 to I-4.I.9-3.A- 287).
  • Table 9-4 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R 9 is Br and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.I.9-4.A-1 to I-1.I.9-4.A-287, compounds I-2.I.9-4.A-1 to I-2.I.9- 4.A-287, compounds I-3.I.9-4.A-1 to I-3.I.9-4.A-287 compounds I-4.I.9-4.A-1 to I-4.I.9-4.A-287).
  • Table 9-5 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .1.9-5.A-1 to I-1.I.9-5.A-287, compounds I-2.I.9-5.A-1 to I- 2.I.9-5.A-287, compounds I-3.I.9-5.A-1 to I-3.I.9-5.A-287 compounds I-4.I.9-5.A-1 to I-4.I.9-5.A- 287).
  • Table 9-6 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.1.9-6.A-1 to 1-1 .1.9-6.A-287, compounds I-2.I.9-6.A-1 to I-2.I.9-6.A-287, compounds I-3.I.9-6.A-1 to I-3.I.9-6.A-287 compounds I-4.I.9-6.A-1 to I-4.I.9- 6.A-287).
  • Table 9-7 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R 9 is H and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.I.9-7.A-1 to I-1.I.9-7.A-287, compounds I-2.I.9-7.A-1 to I-2.I.9-
  • compounds I-3.I.9-8.A-1 to I-3.I.9-8.A-287 compounds I-4.I.9-8.A-1 to I-4.I.9-8.A-287).
  • Particular embodiments of the compounds I are the following compounds: X-1.A, X-1.B, X-1 .C, X-1 .D, X-1.E, X-1 .F, X-1.G, X-1.1; X-2.A, X-2.B, X-2.C, X-2.D, X-2.E, X-2.F, X-2.G, X-2.I; X-3.A, X-3.B, X-3.C, X-3.D, X-3.E, X-3.F, X-3.G, X-3.I; X-4.A, X-4.B, X-4.C, X-4.D, X-4.E, X-4.F, X-4.G, X-4.I
  • Particular embodiments of the compounds I are the following compounds: X-1 .A, X-1 .B, X-1.C, X-1 .D, X-1.E, X-1.F, X-1.G, X-1.1; X-2.A, X-2.B, X-2.C, X-2.D, X-2.E, X-2.F, X-2.G, X-2.1; X-3.A, X-3.B, X-3.C, X-3.D, X-3.E, X-3.F, X-3.G, X-3.1; X-4.A, X-4.B, X-4.C, X-4.D, X-4.E, X-4.F, X-4.G, X-4.1.
  • Tables 1 -1 to 1-8 that are compiled in the Tables 1 -1 to 1-8, Tables 2-1 to 2-8, Tables 3-1 to 3-8, Tables 4-1 to 4-8, Tables 5-1 to 5-8, Tables 6-1 to 6-8, Tables 7-1 to 7-8, Tables 8-1 to 8-8, Tables 9-1 to 9- 8.
  • Tables 1 -1 to 1-8 that are compiled in the Tables 1 -1 to 1-8, Tables 2-1 to 2-8, Tables 3-1 to 3-8, Tables 4-1 to 4-8, Tables 5-1 to 5-8, Tables 6-1 to 6-8, Tables 7-1 to 7-8, Tables 8-1 to 8-8, Tables 9-1 to 9- 8.
  • Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
  • Table 1-1 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R 9 is CH 3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-1.A-1 to X-1.A.1 -1 .A-287, compounds X-2.A.1 -
  • Table 1-2 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R 9 is CHF 2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-2.A-1 to X-1.A.1 -2.A-287, compounds X-2.A.1 -
  • Table 1-4 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R 9 is Br and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-4.A-1 to X-1.A.1 -4.A-287, compounds X-2.A.1-
  • Table 1-5 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R 9 is OCH3 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-5.A-1 to X-1.A.1-5.A-287, compounds X-2.A.1-
  • Table 1-6 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R 9 is cyclopropyl and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-6.A-1 to X-1.A.1-6.A-287, compounds X- 2.A.1-6.A-1 to X-2.A.1-6.A-287, compounds X-3.A.1-6.A-1 to X-3.A.1-6.A-287 compounds X- 4.A.1-6.A-1 to X-4.A.1-6.A-287).
  • Table 1-7 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R 9 is H and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-7.A-1 to X-1.A.1 -7.A-287, compounds X-2.A.1-

Abstract

The present invention relates to compounds of formula I wherein the variables are defined as given in the description and claims. The invention further relates to uses and composition for compounds of formula I.

Description

PYRIDINE COMPOUNDS FOR CONTROLLING PHYTOPATHOGENIC HARMFUL
FUNGI
Description
The present invention relates to pyridine compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the use and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound. The invention also relates to processes for preparing these compounds, intermediates, processes for preparing such intermediates, and to compositions comprising at least one compound I.
In many cases, in particular at low application rates, the fungicidal activity of the known fungi- cidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic harmful fungi.
Surprisingly, this object is achieved by the use of the inventive pyridine compounds of formula I having favorable fungicidal activity against phytopathogenic fungi.
Accordingly, the present invention relates to the com ounds of formula I
Figure imgf000002_0001
wherein
R1 is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the het- eroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 are unsubstituted or substituted by groups R1a which independently of one another are selected from:
R1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or substituted by groups R1b which independently of one another are selected from:
R1b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R2 is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R2 are unsubstituted or substituted by groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted or substituted by substituents R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or
substituted by groups R2b which independently of one another are selected from: R2b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl,
C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R3 is in each case independently selected from CH3, CH2F, CHF2 and CF3;
R4 is independently selected from CN, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogen- alkynyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-halogenalkoxy, CH(=0),
C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R' and R" are independently selected from H, Ci-C4- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(CrC4-alkyl), N(C C4-alkyl)2, NH-S02-Rx, d-C6-alkyl, C C6-halogenalkyl, C2- C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci- C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or
wherein the acyclic moieties of R4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R4a, which independently of one another are selected from:
R a halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4- alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6- alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)0(Ci-C6-alkyl), C(=0) N H(Ci-C6-alkyl), C(=0)N(C C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N , O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , CN , N02, SH , N H2, N H(CrC4-al- kyl), N(CrC4-alkyl)2, N H(C(=0)C C4-alkyl), N(C(=0)C C4-alkyl)2, N H-S02-Rx, Ci- C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl; and wherein Rx, R' and R" are as defined above wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R4 are independently unsubstituted or substituted with identical or different groups R4b, which independently of one another are selected from:
R b halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4- alkyl), N(C(=0)d-C4-alkyl)2, N H-S02-Rx, C C4-alkyl, C C4-alkoxy, C C4-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, CrC4-halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , C1-C4- alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
and wherein Rx is as defined above;
n is 0, 1 , 2 or
R3, R4 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N , O and S, wherein the heteroatom N may carry one substituent selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from CN , Ci-C4-al- kyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or S02, and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R34 independently selected from halogen, OH , CN , N02, SH , N H2, CrC6-alkyl, Ci-C6-halogen- alkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C4- alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R34a selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and
R5 is H;
R6 is H;
A is selected from below group:
Figure imgf000005_0001
wherein, the positions of the rings marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I.; wherein
Y is H;
o is 0, 1 , 2 or 3; and
R78 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(C C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-R*, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N , O and S; wherein Rx , R' and R" are as defined above; and wherein the acyclic moieties of R78 are unsubstituted or substituted by R78a which independently of one another are selected from:
R78a halogen, OH , CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or substituted by R78aa selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubstituted or substituted by R78b which independently of one another are selected from:
R78b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio;
is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H2, N H(Ci- C4-alkyl), N(Ci-C4-alkyl)2, N H (C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4-alkynyl)2, N H(C3-C6-cycloalkyl), N (C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4- alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4- alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n- aryl, Ci-C6-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)N H (C Ce-alkyl), CH(=S), C(=S)C C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- Ce-cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3- C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S; wherein
Rx is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, and C3-C6-halogencycloalkyl; wherein the acyclic moieties of R9 are unsubstituted or substituted by groups R9a which independently of one another are selected from:
R9a halogen, OH , CN , d-Ce-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R9 are unsubstituted or
substituted by groups R9b which independently of one another are selected from:
R9b halogen, OH , CN , C C4-alkyl, C C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio; R10 is in each case independently selected from the substituents as defined for R9, wherein the possible substituents for R10 are R10a and R10b , respectively, which correspond to R9a and R9b, respectively;
R9, R10 together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or het- eroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted by substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R11)m, wherein m is 0, 1 , 2, 3 or 4;
R11 is in each case independently selected from halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, d-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;
wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein
Rx is as defined above;
wherein the acyclic moieties of R11 are unsubstituted or substituted with identical or different groups R11a which independently of one another are selected from:
R11a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R11 unsubstituted or substituted with identical or different groups R11b which independently of one another are selected from:
R11b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; with the provisio that f A is phenyl,
R1 is H; and
R4 can not be unsubstituted Ci-C6-alkyl; and
R10 can not be H
and the N-oxides and the agriculturally acceptable salts thereof.
Compounds of formula I can be accessed e.g. starting from alcohols of type II with nitriles of type III in the presence of an acid in an organic solvent (see for example US 2008/0275242 or WO2005/070917). Preferably, sulfuric acid or a sulfonic acid, in particular triflic acid, are used as acid. Most suitable solvents are hydrocarbons, preferably benzene or dichloromethane. In the following schemes, the optionally substituted phenyl or heteroaryl formed by W together with the partially substituted pyridine ring to which it is attached is sketched by a semicircle named "A":
Figure imgf000008_0001
Depending on the nature of the starting materials, the reaction is performed at a temperature from -40°C to 200°C, in particular from -10°C to 120°C, more specifically from 0°C to 100°C, even more specifically from room or ambient temperature (about 23°C) to 80°C.
Nitriles of type II I are either commercially available or can be prepared by a skilled person from the corresponding halides following literature precedures (see, for example Journal of Organic Chemistry, 76(2), 665-668; 201 1 ; Angewandte Chemie, International Edition, 52(38), 10035- 10039; 2013; WO2004/013094).
Alcohols of type I I can be prepared as described below. A skilled person will realize that compounds of type l llb can be reacted with organometallic reagents, preferably alkyl Grignard or al- kyl-Lithium reagents, in ethereal solvents, preferably THF at low temperatures and under inert conditions to furnish compounds of type I I.
Figure imgf000008_0002
lllb
Alternatively, alcohols of type I I can be prepared from epoxydes I l ia and compounds VI (see below):
"metallation"
Figure imgf000008_0003
The metallation reaction may preferably be carried out using Lithium-organic compounds, such as for example n-butyl lithium, sec-butyl lithium or tert-butyl lithium to result in an exchange of halogen by lithium. Also suitable is the reaction with magnesium resulting in the formation of the respective Grignard reagents. A further possibility is the use of other Grignard reagents such as isopropyl-magnesium-bromide instead of Mg.
A typical preparation of compounds of type l llb can be achieved by reacting compounds of type IV with organometallic reagents, preferably alkyl Grignard or alkyl-Lithium reagents, in ethereal solvents, preferably THF at low temperatures and under inert conditions to furnish compounds of type III as previously reported (see for example WO2012051036; WO201 1042918).
Figure imgf000009_0001
Compounds of type IV can be accessed by reacting a carbonyl compound of type V, preferably a carboxylic acid (X = OH) or an acid chloride (X = CI), with NH(OR')R", wherein R' and R" are selected from (Ci-C4)-alkyl, most preferably being methyl, in an organic solvent, preferably THF or dichloromethane. Typically the reaction is performed in a range between 0 °C and ambient temperature in the presence of an organic base, preferably N(C2Hs)3 or pyridine (see e.g. US 20130324506; Tetrahedron: Asymmetry, 17(4), 508-51 1 ; 2006). If X = OH, the addition of an activating reagent, preferably a carbodiimide, may be preferred (see for example ChemMedChem, 7(12), 2101 -21 12; 2012; 201 1038204; Journal of Organic Chemistry, 76( 1 ), 164-169; 201 1 ).
Figure imgf000009_0002
If required, compounds of type V can be prepared from the corresponding aryl halides of type VI (Hal is halogen, preferably Br or I). As described (Tetrahedron, 68(9), 21 13-2120; 2012; Chemical Communications (Cambridge, United Kingdom), 49(60). 6767-6769; 2013), aryl halides will react with compounds of type VII in the presence of a transition metal catalyst, preferably a cop- per(l) salt, in an organic solvent, preferably DMF or DMSO, at elevated temperatures. Typically a base, preferably potassium phosphate, is added.
Figure imgf000009_0003
If appropriate, compounds of type II can be prepared as follows. A known or commercially available compound of type VIII can be reacted with an organometallic reagent of type IX, preferably a Grignard or an organolithium reagent, readily prepared by a skilled person. Preferably, the reaction is performed in a temperature range from -78 °C to room temperature under inert conditions in an ethereal solvent.
Figure imgf000009_0004
Alternatively compounds I in which R5 stands for hydrogen can be accessed by reacting a ni- trile III with an olefin ll# under acidic conditions as described elsewhere (US 7632783, B2, page 60, method A).
Figure imgf000010_0001
I
Alternatively compounds I can be prepared via intramolecular reaction of amide X when A is an electron-rich carbon- or heterocycle. The intramolecular cyclization will take place in the presence of a dehydrating agent in an organic solvent (WO 2008143263, Synthetic Communications 2007, 37, 1331 -1338.). Preferably, phosphoryl chloride (POCI3), POCI3/P2O5, H3PO4/P2O5, SnCU or BF3 are used as dehydrating agent. Most suitable solvents are hydrocarbons, prefera- bly benzene, toluene or acetonitrile. Alternatively halogenated solvents can be used, for example dichloromethane, chloroform or chlorobenzene.
Figure imgf000010_0002
Depending on the nature of starting materials, the reaction is performed at temperature from - 40°c to 200 °C, in particular from -10°C to 120°C, more specifically from 0°C to 100°C, even more specifically from room temperature to 100°C.
Amides of type X can accessed by reacting a carbonyl of type XI, preferably a carboxylic acid (X = OH) or an acid chloride (X = CI), with an amines of type XII in an organic solvent, preferably THF or dichloromethane. Typically the reaction is performed in a range between 0°C and room temperature in the presence of an organic base, preferably N(C2Hs)3 or pyridine (see e.g. WO 8303968). If X = OH, the addition of an activating agent, preferably a carbodiimide or acid chloride, may be preferred (see e.g Bioorganic & Medicinal Chemistry, 2010, 18, 3088-31 15).
Figure imgf000010_0003
If required, compounds of type XII can be synthesized from the correspond nitriles. As de- scribed Synlett. 2007, 4 652-654 or Tetrahedron 2012, 68, 2696-2703, nitriles will react with or- ganometallic agents, preferably Grignard or Lithium reagent, in ethereal solvents, preferably THF at low temperature and under inert conditions to furnish compounds of type XII. The synthesis of compounds of type XII can take place in two steps or one pot.
The N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroper- benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(1 1 ), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981 ) or ox- one (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001 ). The oxidation may lead to pure mono- N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
In the following, the intermediate compounds are further described. A skilled person will readily understand that the preferences for the substituents, also in particular the ones given in the ta- bles below for the respective substituents, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.
The intermediate compounds of formula X are novel. Consequently, one aspect of the present invention relates to compounds of formula X: The intermediate compounds of formula X are novel. Consequently, one aspect of the present invention relates to compounds of formula X:
Figure imgf000011_0001
The compounds of formula X have fungicidal activity and the details below referring to the pounds I also apply to compounds X.
Particular embodiments of the compounds X are the following compounds
Figure imgf000012_0001
Xk
If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.
In the definitions of the variables given above, collective terms are used which are generally representative for the substituents in question. The term "Cn-Cm" indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
The term "halogen" refers to fluorine, chlorine, bromine and iodine.
The term "Ci-C6-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dime- thylpropyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethyl- butyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-tri- methylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl and 1 -ethyl-2-methylpropyl. Likewise, the term "C2-C4-alkyl" refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propoyl), butyl, 1 -methylpropyl (sec- butyl), 2-methylpropyl (iso-butyl), 1 ,1-dimethylethyl (tert.-butyl).
The term "CrC6-halogenalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are "Ci-C2-halogenalkyl" groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlor- ofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoro- ethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-
2.2- difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.
The term "Ci-C6-hydroxyalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by OH groups.
The term "CrC4-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above). Likewise, the term "Ci-C6-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C6-alkoxy group (as defined above).
The term "C2-C6-alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position. Examples are "C2-C4-alkenyl" groups, such as ethenyl, 1 -propenyl, 2-propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl.
The term "C2-C6-alkynyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond. Examples are "C2-C4-al- kynyl" groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but-
3- ynyl, 1 -methyl-prop-2-ynyl.
The term "Ci-C6-alkoxy" refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group. Examples are "C1-C4- alkoxy" groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1 -methyhprop- oxy, 2-methylpropoxy or 1 ,1-dimethylethoxy.
The term "Ci-C6-halogenalkoxy" refers to a Ci-C6-alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are "Ci-C4-halogenalkoxy" groups, such as OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro- ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,
2.3- difluoro-"propoxy, 2 chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -fluo- romethyl-2-fluoroethoxy, 1 -chloromethyl-2-chloroethoxy, 1 -bromomethyl-2-bromoethoxy,
4- fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
The term "C2-C6-alkenyloxy" refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are "C2-C4-alkenyloxy" groups.
The term "C2-C6-alkynyloxy" refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are "C2-C4-alkynyloxy" groups.
The term "C3-C6-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbo- cycle is a "C3-Cio-cycloalkyl".
The term "C3-C6-cycloalkenyl" refers to a monocyclic partially unsaturated 3-, 4- 5- or 6-mem- bered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cy- clopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four- , five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C3-Cio-cycloal- kenyl".
The term "C3-C8-cycloalkyl-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).
The term "Ci-Ce-alkylthio" as used herein refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the term "Ci- C6-halogenalkylthio" as used herein refers to straight-chain or branched halogenalkyi group hav- ing 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the halogenalkyi group.
The term "C(=0)-Ci-C6-alkyl" refers to a radical which is attached through the carbon atom of the group C(=0) as indicated by the number valence of the carbon atom. The number of valence of carbon is 4, that of nitrogen is 3. Likewise the following terms are to be construed: NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, C(=0)-NH(Ci-C6- alkyl), C(=0)-N(Ci-C6-alkyl)2.
The term "saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten- membered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S" is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and S. For example:
a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azet- idine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine; and
a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O, N and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isox- azolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazoli- dinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazoli- dinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,
1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5- yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin- 3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxa- zolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5- yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4- yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyra- zol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropy- razol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydro- pyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihy- dropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihy- drooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihy- drooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidi- nyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tet- rahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hex- ahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4- hexahydrotriazin-3-yl and also the corresponding -ylidene radicals; and
a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroaze- pinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahy- dro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1-,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]oxepin-2-, -3-,-4-,-5- ,-6- or-7-yl, hexahydroazepin-1 -,-2-,-3- or-4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl, tetra- and hexahydro-1 ,4-oxa- zepinyl, tetra- and hexahydro-1 ,3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the corresponding -ylidene radicals.
The term "substituted" refers to substitued with 1 , 2, 3 or up to the maximum possible number of substituents.
The term "5-or 6-membered heteroaryl" or "5-or 6-membered heteroaromatic" refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example,
a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan- 2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl; or
a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyri- dazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
Agriculturally acceptable salts of the inventive compounds encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of said compounds. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammo- nium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting such inventive compound with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid. The inventive compounds can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.
Depending on the substitution pattern, the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure di- astereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or dia- stereomers and their mixtures are subject matter of the present invention.
In the following, particular embodiments of the inventive compounds are described. Therein, specific meanings of the respective substituents are further detained, wherein the meanings are in each case on their own but also in any combination with one another, particular embodiments of the present invention.
Furthermore, in respect of the variables, generally, the embodiments of the compounds I also apply to the intermediates.
R1 according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 are unsubstituted or substituted with identical or different groups R1a which independently of one another are selected from:
R1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, C1-C4- halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or substituted with identical or different groups R1b which independently of one another are selected from:
R1b halogen, OH, CN, C C4-alkyl, C C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio. For every R1 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R1 that may be present in the ring.
According to one embodiment of formula I, R1 is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
According to another embodiment of formula I, R1 is hydrogen.
According to still another embodiment of formula I, R1 is halogen, in particular Br, F or CI, more specifically F or CI.
According to another embodiment of formula I, R1 is F
According to another embodiment of formula I, R1 is CI
According to another embodiment of formula I, R1 is Br.
According to still another embodiment of formula I, R1 is OH.
According to still another embodiment of formula I, R1 is CN.
According to still another embodiment of formula I, R1 is NO2.
According to still another embodiment of formula I, R1 is SH.
According to still another embodiment of formula I R1 is NH2, NH(CrC4-alkyl), N(CrC4-alkyl)2 or NH-S02-RX, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy.
According to still another embodiment of formula I, R1 is Ci-C6-alkyl, in particular Ci-C4-alkyl,
Figure imgf000017_0001
According to still another embodiment of formula I, R1 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2, CH2CI, CF3CH2, CCI3CH2 or CF2CHF2.
According to still another embodiment of formula I, R1 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, C(CH3)=CH2, CH=CCI2, CH=CF2, CCI=CCI2, CF=CF2, CH=CH2, CH2CH=CCI2, CH2CH=CF2, CH2CCI=CCI2, CH2CF=CF2, CCI2CH=CCI2, CF2CH=CF2, CCI2CCI=CCI2, or CF2CF=CF2.
According to still another embodiment of formula I, R1 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡CCI, C≡CF. CH2C≡CH, CH2C≡CCI, or CH2C≡CF.
According to still another embodiment of formula I, R1 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I, R1 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to still another embodiment of formula I R1 is C3-C6-cycloalkyl, in particular cyclopro- pyl. According to still another embodiment of formula I, R1 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R1b as defined and preferably herein.
According to still another embodiment of formula I, R1 is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R1 is unsubstituted aryl or aryl that is substituted by one, two, three or four R1b, as defined herein. In particular, R1 is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R1b, as defined herein.
According to still another embodiment of formula I, R1 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R1 is 5- or 6-membered heteroaryl that is substituted by one, two or three R1b, as defined herein.
According to still another embodiment of formula l,R1 is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R1 are not further substituted or carry one, two, three, four or five identical or different groups R1a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R1 are not further substituted or carry one, two, three, four or five identical or different groups R1b as defined below.
According to still another embodiment of formula I, R1 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and CrC4-halogenalkoxy.
R1a are the possible substituents for the acyclic moieties of R1.
R1a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, Ci-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br. In to one embodiment R1a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R1a is
independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R1a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I, R1a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R1a is
independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
R1b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R1.
R1b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R1b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-hal- ogenalkoxy. Specifically, R1b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and halogenmethoxy.
According to still another embodiment thereof R1b is independently selected from halogen, C-i- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R1b is independently selected from halogen, CN, OH, CH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1 -C - cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1 -C - cyclopropyl, OCHF2 and OCF3.
Rx in the substituent NH-S02-RX is in each case independently selected from Ci-C4-alkyl, C1-C4- halogenalkyl, unsubstituted aryl and aryl that is substituted by one, two, three, four or five substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy. In particular, Rx is in each case independently selected from Ci-C4-alkyl, halogen, OH, CN and phenyl that is substituted by one, two or three Rx1 independently selected from Ci-C2-alkyl, more specifically Rx is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted by one CH3., more specifically S02-Rx is the tosyl group ("Ts").
Particularly preferred embodiments of R1 according to the invention are in Table P1 below, wherein each line of lines P1 -1 to P1-16 corresponds to one particular embodiment of the inven- tion. Thereby, for every R1 that is present in the inventive compounds, these specific
embodiments and preferences apply independently of the meaning of any other R1 that may be present in the ring:
Table P1 :
"Ts" in the table stands for the tosylgroup S02-(p-CH3)phenyl.
Figure imgf000019_0001
Figure imgf000019_0002
30 R2 according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R2 are unsubstituted or substituted with identical or different groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4- halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or substituted with identical or different groups R2b which independently of one another are selected from:
R2b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalky, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
For every R2 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of the other R2 that may be present in the ring.
According to one embodiment of formula I, R2 is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
According to another of formula I, R2 is halogen, in particular Br, F or CI, more specifically F or CI.
According to another embodiment of formula I, R2 is F
According to another embodiment of formula I, R2 is CI
According to another embodiment of formula I, R2 is Br.
According to still another embodiment of formula I, R2 is hydrogen
According to still another embodiment of formula I, R2 is OH.
According to still another embodiment of formula I, R2 is CN.
According to still another embodiment of formula I, R2 is N02.
According to still another embodiment of formula I, R2 is SH.
In a further specific embodiment R2 is NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-Rx, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy. According to still another embodiment of formula I, R2 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3 or CH2CH3.
According to still another embodiment of formula I, R2 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2, CH2CI, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment, R2 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, CH=CCI2, CH=CF2, CCI=CCI2, CF=CF2, CH=CH2, CH2CH=CCI2, CH2CH=CF2, CH2CCI=CCI2, CH2CF=CF2, CCI2CH=CCI2, CF2CH=CF2, CCI2CCI=CCI2, or CF2CF=CF2.
According to still a further embodiment, R2 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡CCI, C≡CF. CH2C≡CH, CH2C≡CCI, or CH2C≡CF.
According to still another embodiment of formula I, R2 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I, R2 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
In a further specific embodiment R2 is C3-C6-cycloalkyl, in particular cyclopropyl.
In a further specific embodiment, R2 is C3-C6-cycloalkyl, for example cyclopropyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R2b as de- fined and preferably herein.
According to still another embodiment of formula I, R2 is C3-C6-halogencycloalkyl. In a special embodiment R2 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R2 is unsubstituted aryl or aryl that is substituted by one, two, three or four R2b, as defined herein. In particular, R2 is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R2b, as defined herein.
According to still another embodiment of formula I, R2 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R2 is 5- or 6-membered heteroaryl that is substituted by one, two or three R2b, as defined herein.
According to still another embodiment of formula I, R2 is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(C C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R2 are not further substituted or carry one, two, three, four or five identical or different groups R2a as defined below and wherein the cycloalkyl moieties of R2 are not further substituted or carry one, two, three, four or five identical or different groups R2b as defined below. According to still another embodiment of formula I, R2 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
R2a are the possible substituents for the acyclic moieties of R2. R2a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
According to one embodiment R2a is independently selected from halogen, OH, CN, C1-C2- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R2a is independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R2a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I, R2a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R2a is
independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
R2b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R2.
R2b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R2b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R2b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and halogenmethoxy.
According to still another embodiment thereof R2b is independently selected from halogen, C-i- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R2b is independently selected from halogen, OH, CH3, OCH3, CN, CHF2, OCHF2, OCF3, OCH3 cyclopropyl, 1 -F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1-F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-CI2-cyclopropyl, OCHF2 and OCF3.
Particularly preferred embodiments of R2 according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-16 corresponds to one particular embodiment of the invention. Thereby, for every R2 that is present in the inventive compounds, these specific
embodiments and preferences apply independently of the meaning of any other R2 that may be present in the ring:
Table P2:
"Ts" in the table stands for the tosylgroup S02-(p-CH3)phenyl.
Figure imgf000023_0001
R3 is in each case independently selected from CH3, CH2F, CHF2 and CF3.
According to one embodiment R3 is CH3.
According to another embodiment R3 is CH2F.
According to still another embodiment R3 is CHF2.
According to another embodiment R3 is CF3.
R4 is independently selected from CN, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C6-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci- C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-halogenalkoxy, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R' and R" are independently selected from H, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are inde- pendently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, N02, SH, NH2, NH(CrC4-alkyl), N(C C4-alkyl)2, NH-S02-Rx, d-C6-alkyl, C C6-halo- genalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or wherein the acyclic moieties of R4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R4a, which independently of one another are selected from:
R a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, C C6-alkoxy, C C4-halogenalkoxy, C C6-alkylthio, C C6-halo- genalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)C C6-alkyl, C(=0)0(C C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocy- cle contains independently one, two, three or four heteroatoms selected from N, O and S;
wherein the carbo-, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4- alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halo- genalkoxy, and S(0)n-Ci-C6-alkyl; and wherein Rx, R' and R" are as defined above;
wherein the carbo-, heterocyclic, heteroaryl and aryl moieties of R4 are independently unsubstituted or substituted with identical or different groups R4b, which independently of one another are selected from:
R4b halogen, OH, CN, N02, SH, NH2, NH(C C4-alkyl), N(C C4-alkyl)2, NH(C(=0)C C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, d-C4-alkyl, Ci-C4-alkoxy, C C4-halogenalkyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-a lkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein Rx is as defined above;
n is 0, 1 , 2.
R4 is independently selected from CN, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C6-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci- C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-halogenalkoxy, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R' and R" are independently selected from H, CrC4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are inde- pendently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halo- genalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or wherein the acyclic moieties of R4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R4a, which independently of one another are selected from: R a halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halo- genalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)N H(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N , O and S;
wherein the carbo-, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen,
OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4- alkyl)2, N H-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halo- genalkoxy, and S(0)n-Ci-C6-alkyl; and wherein Rx, R' and R" are as defined above;
wherein the carbo-, heterocyclic, heteroaryl and aryl moieties of R4 are independently unsubsti- tuted or substituted with identical or different groups R4b, which independently of one another are selected from:
R b halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-a lkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein Rx is as defined above;
n is 0, 1 , 2.
According to one embodiment of formula I, R4 is selected from R4 is in each case independently selected from CN , Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl, CH(=0), C(=0)Ci-C6-alkyl,
C(=0)0(Ci-C6-alkyl), CR'=NOR", C3-C6-halogencycloalkyl, a saturated three-, four-, five-, six-, membered carbo- or heterocycle, a five- or six-membered heteroaryl or aryl; and Ci-C6-alkyl substituted by CN , C C6-alkoxy, d-C4-halogenalkoxy, C C6-alkylthio, S(0)n-CrC6-alkyl, N H- S02-Rx, N(CrC6-alkyl)2, CH(=0), C(=0)C C6-alkyl, C(=0)0(C C6-alkyl), a saturated three-, four-, five-, six-, membered carbo- or heterocycle, aryl; wherein Rx, R' and R" are defined below; and wherein the acyclic moieties of R4 are unsubstituted or substituted with identical or different groups R4a as defined below and wherein wherein the carbo-, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R4b as defined below.
According to one embodiment of formula I, R4 is selected from R4 is in each case independently selected from C2-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2- Ce-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl, CH(=0), C(=0)C2-C6-alkyl, C(=0)0(C2- C6-alkyl), CR'=NOR" , C3-C6-halogencycloalkyl, a saturated three-, four-, five-, six-, membered carbo- or heterocycle, a five- or six-membered heteroaryl or aryl; and Ci-C6-alkyl substituted by CN , d-Ce-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, S(0)n-Ci-C6-alkyl, N H-S02-Rx, N(Ci-C6- alkyl)2, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), a saturated three-, four-, five-, six-, membered carbo- or heterocycle, aryl; wherein Rx, R' and R" are defined below; and wherein the acyclic moieties of R4 are unsubstituted or substituted with identical or different groups R4a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R4b as defined below.
According to still another embodiment of formula I, R4 is selected from Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted by substituents R4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted. In a particular embodiment, R4 is selected from Ci-C6-halogenalkyl, phenyl-Ch , halogenphenyl-Chb, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted by substituents R4b as defined below.
According to still another embodiment of formula I, R4 is selected from Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted bysubstituents R4b as defined below. According to one embodiment thereof, the carbo- and heterocycle is unsubstituted. In a particular embodiment, R4 is selected from substituted Ci-C6-hal- ogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted bysubstituents R4b as de- fined below.
According to another embodiment of formula I, R4 is selected from C2-C6-alkenyl, C2-C6-halo- genalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- C6-alkylaryl, six-membered heteroaryl or aryl which is unsubstituted or substituted by halogen or Ci-C6-halogenalkyl, and wherein the acyclic moieties of R4 are unsubstituted or substituted with identical or different groups R4a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R4b as defined below.
According to still another embodiment of formula I, R4 is selected from CN, C2-C6-alkenyl, C2-C6- halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R4 are unsubstituted or substituted with identical or different groups R4a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R4b as defined below.
According to still another embodiment of formula I, R4 is CN.
According to still another embodiment of formula I, R4 is Ci-C6-alkylthio, such as SCH3, SC2H5, Sn-propyl, Si-propyl, Sn-butyl, Si-butyl, Stert-butyl, Sn-pentyl, Si-pentyl, CH2SCH3 or
Figure imgf000026_0001
According to still another embodiment of formula I, R4 is Ci-C6-halogenalkylthio, such as SCF3, According to still another embodiment of formula I, R4 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I, R4 is Ci-C6-alkyl such as CH3. According to still another embodiment of formula I, R4 is Ci-C6-alkyl such as C2H5. According to still another embodiment of formula I, R4 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted by at least one group R4a, which independently of one another are selected from:
R4a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, C C6-alkoxy, C C4-halogenalkoxy, Ci-C6-alkylthio, C C6- halogenalkylthio, S(0)n-CrC6-alkyl, S(0)n-aryl, CH(=0), C(=0)C C6-alkyl, C(=0)0(C C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR" a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubsti- tuted or carry one, two, three, four or five substituents selected from the group consisting of hal- ogen, OH, CN, N02, SH, NH2, NH(C C4-alkyl), N(C C4-alkyl)2, NH(C(=0)C C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4- alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl.
According to still another embodiment of formula I, R4 is CH3 is substituted by at least one group R4a, which independently of one another are selected from:
R4a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6- halogenalkylthio, S(0)n-CrC6-alkyl, S(0)n-aryl, CH(=0), C(=0)C C6-alkyl, C(=0)0(C C6-alkyl), C(=0)NH(CrC6-alkyl), C(=0)N(C C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubsti- tuted or carry one, two, three, four or five substituents selected from the group consisting of hal- ogen, OH, CN, N02, SH, NH2, NH(C C4-alkyl), N(C C4-alkyl)2, NH(C(=0)d-C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, C C6-alkylthio, Ci-C4-alkyl, C C4-halogenalkyl, Ci-C4- alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl.
According to still another embodiment of formula I, R4 is C2Hs is substituted by at least one group R4a, which independently of one another are selected from:
R4a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6- halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(CrC6-alkyl), C(=0)N(C C6-alkyl)2, CR'=NOR"a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubsti- tuted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl.
According to still another embodiment of formula I, R4 is CH2CN.
According to still another embodiment of formula I, R4 is CH2OH.
According to still another embodiment of formula I, R4 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, more specifically Ci-C2-halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2.
According to still a further embodiment of formula I, R4 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2, CH2CH=CH2 or C(CH3)C=CH2.
According to a further specific embodiment of formula I, R4 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CF=CF2, CCI=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2,
CH2CH=CCI2, CH2CF=CF2, CH2CCI=CCI2, CF2CF=CF2 or CCI2CCI=CCI2.
According to still a further embodiment of formula I, R4 is C2-C6-cycloalkenyl, in particular C2-C4- cycloalkenyl, such as CH=CH2-cPr.
According to still a further embodiment of formula I, R4 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, C C-CI,
Figure imgf000028_0001
CH2- C≡CH, CH2-C≡CCI or CH2- C≡C-CH3.
According to still a further embodiment of formula I, R4 is C2-C6-cycloalkynyl in particular C2-C4- cycloalkynyl, such as C C-cPr.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3, CH2CH3 or CH2OCH3.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl-Ci-C6-alkoxy, in particular Ci-C4-alkyl-Ci-C4-alkoxy, more specifically Ci-C2-alkyl-Ci-C2-alkoxy, such as
Figure imgf000028_0002
According to a further specific embodiment of formula I, R4 is C2-C6-alkenyloxy, in particular C2- C4-alkenyloxy, more specifically Ci-C2-alkenyloxy such as OCH=CH2, OCH2CH=CH2
OC(CH3)CH=CH2, CH2OCH=CH2, or CH2OCH2CH=CH2.
According to a further specific embodiment of formula I, R4 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH, OCH2C=CH or CH2OC=CH
According to a further specific embodiment of formula I, R4 is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl-Ci-C6-halogenalkoxy, in particular Ci-C4-alkyl-Ci-C4-halogenalkoxy, more specifically Ci-C2-alkyl-Ci-C2-halogenalkoxy such as CH2OCF3, CH2OCHF2, CH2OCH2F, CH2OCCI3, CH2OCHCI2 or CH2OCH2CI, in particular CH2OCF3, CH2OCHF2, CH2OCCI3 or CH2OCHCI2. According to a further specific embodiment of formula I, R4 is CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl) or C(=0)N(Ci-C6-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R4 is Ci-C4-alkyl-CH(=0), Ci-C4-alkyl- C(=0)Ci-C6-alkyl, Ci-C4-alkyl-C(=0)0(Ci-C6-alkyl), Ci-C4-alkyl-C(=0)NH(Ci-C6-alkyl) or Ci-C4- alkyl-C(=0)N(Ci-C6-alkyl)2, especially CH2CH(=0), CH2C(=0)CrC6-alkyl, CH2C(=0)0(C C6- alkyl), CH2C(=0)NH(C C6-alkyl) or CH2C(=0)N(CrC6-alkyl)2 wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R4 is CR'=NOR" such as
C(CH3)=NOCH3, C(CH3)=NOCH2CH3 or C(CH3)=NOCF3.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl-NH(Ci-C4-alkyl) or Ci- C6-alkyl-N(Ci-C4-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl-S(0)n-CrC6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1 , 2 or 3.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl-S(0)n-Ci-C6- halogenalkyl, wherein halogenalkyl is CF3 or CHF2 and n is 1 , 2 or 3.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl-S(0)n-aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R4b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0)n-Ci-C6-alkyl, in particular F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R4 is unsubstituted phenyl. According to another embodiment, R4 is phenyl, that is substituted by one, two or three, in par- ticular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl-NH-S02-Rx wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx2 independently selected from Ci-C4-alkyl, halogen, OH, CN, CrC4-halogenalkyl, Ci-C4-alkoxy, or CrC4-halogenalkoxy, such as CH2NHS02CF3 or
CH2NHS02CH3.
According to still another embodiment of formula I, R4 is selected from Ci-C6-alkyl which is substituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or sub- stituted by substituents R4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
According to one embodiment, R4 is selected from Ci-C6-alkyl, especially CH2 which is substituted by a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b. According to one embodiment, R4 is selected from Ci-C6-alkyl, especially Chb which is substituted by a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to one embodiment, R4 is selected from Ci-C6-alkyl, especially with R optionally substituted CH2 which is substituted by a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to one embodiment, R4 is selected from Ci-C6-alkyl, especially Chb which is substi- tuted by a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially Chb substituted by a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in par- ticular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially Chb substituted by a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially Chb substituted by a 5-membered saturated heterocycle which contains one N as ring member and optionally one or two groups Ch are replaced by C(=0).
According to still another embodiment of formula I , R4 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted by substituents R4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted. According to still another embodiment of formula I, R4 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R4b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
According to still a further embodiment, R4 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R4b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
According to still another embodiment of formula I, R4 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-mem- bered, wherein the carbocycle is unsubstituted or substituted by substituents R4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
According to one embodiment, R4 is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R4 is a 3-membered saturated carbocycle, which is
unsubstituted such as cyclopropyl
According to one embodiment, R4 is a 3-membered saturated carbocycle, which is substituted by halogen, more specifically by F, such as C3H3F2.
According to one embodiment, R4 is a 3-membered saturated carbocycle, which is substituted by halogen. More specifically by CI, such as C3H3CI2.
According to one embodiment, R4 is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R4 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R4 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to still another embodiment of formula I, R4 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R4b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, R4 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-mem- bered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R4b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, in the embodiments of R4 described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
According to one embodiment, R4 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to still another embodiment of formula I, R4 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4 .
According to still another embodiment of formula I, R4 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to still another embodiment of formula I, R4 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R4b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0)n-Ci-C6-alkyl, in particular from CN, F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3 and S(0)2CH3.
According to still another embodiment of formula I, R4 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R4b which independently of one another are selected from from CN, halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0)n-Ci-C6-alkyl, in particular from CN, F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R4 is unsubstituted phenyl. According to another embodiment, R4 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI. According to still another embodiment of formula I, R4 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R4 is a 6-membered heteroaryl, such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
Particularly preferred embodiments of R4 according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-129 corresponds to one particular embodiment of the invention, wherein P4-1 to P4-129 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R4 is bound is marked with "#" in the drawings.
Figure imgf000033_0002
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000037_0001
According to still another embodiment of formula I, R3, R4 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, wherein the heteroatom N may carry one substituent selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from CN, Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or SO2, and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R34 independently selected from halogen, OH, CN, N02, SH, NH2, d-Ce-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci- C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R34a selected from the group consisting of CN, halogen, OH , Ci-C4-alkyl, Ci-C4-halo- genalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S).
According to one embodiment, R3 and R4 form a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b. According to one embodiment, R3 and R4 form a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R3 and R4 form a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R3 and R4 form a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R3 and R4 form a 7-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R3 and R4 form a 3-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R3 and R4 form a 4-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R3 and R4 form a 5-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R3 and R4 form a 6-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R3 and R4 form a 7-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4.
Particularly preferred embodiments of combinations of R3 and R4 according to the invention are in Table P34 below, wherein each line of lines P34-1 to P34-535 corresponds to one particular embodiment of the invention, wherein P34-1 to P34-535 are also in any combination with one another a preferred embodiment of the present invention. The carbon atom, to which R3 and R4 are bound is marked with * in the drawings. "Ts" in the drawings stands for the tosylgroup SO2- (p-CH3)phenyl.
Table P34
No. R3 R4 No. R3 R4
P34-1 CHs CFs P34-3 CHs CH2CI
P34-2 CHs CH2F P34-4 CHs CHF2
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
No. R3 R4 No. R3 R4
P34-136 CH2F CH2CCI3 P34-162 CH2F #
P34-137 CH2F CF2CHF2
P34-138 CH2F CH2OCH3 P34-163 CH2F
P34-139 CH2F CH2OCH2F CI ff
P34-140 CH2F CH2OCHF2 P34-164 CH2F
P34-141 CH2F CH2OCF3
P34-142 CH2F CH2OCF2CHF2 P34-165 CH2F
P34-143 CH2F CH2NHMe
P34-144 CH2F CH2SMe P34-166 CH2F
P34-145 CH2F CH2SOMe
P34-146 CH2F CH2S02Me P34-167 CH2F
P34-147 CH2F CH2NMe2
P34-148 CH2F CH2NS02CF3 P34-168 CH2F
P34-149 CH2F CH2NS02CH3
P34-150 CH2F CN
P34-169 CH2F 0
P34-151 CH2F CH2CN
P34-152 CH2F CHO
P34-153 CH2F COMe P34-170 CH2F 0
P34-154 CH2F C02Me
P34-155 CH2F CH2CHO 0
P34-156 CH2F CH2COMe P34-171 CH2F
P34-157 CH2F CH2C02Me
# O—
P34-158 CH2F
P34-172 CH2F
P34-159 CH2F # o-cF3
P34-173 CH2F
P34-160 CH2F
#
P34-161 CH2F
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
No. R3 R4 No. R3 R4
P34-265 CHF2 CH2CCI3 P34-291 CHF2 #
P34-266 CHF2 CF2CHF2
P34-267 CHF2 CH2OCH3 P34-292 CHF2
P34-268 F CI ff
CHF2 CH2OCH2
P34-269 CHF2 CH2OCHF2 P34-293 CHF2
P34-270 CHF2 CH2OCF3
P34-271 CHF2 CH2OCF2CHF2 P34-294 CHF2
P34-272 CHF2 CH2NHMe
P34-273 CHF2 CH2SMe P34-295 CHF2
P34-274 CHF2 CH2SOMe
P34-275 CHF2 CH2S02Me P34-296 CHF2
P34-276 CHF2 CH2NMe2
P34-277 CHF2 CH2NS02CF3 P34-297 CHF2
P34-278 CHF2 CH2NS02CH3
P34-279 CHF2 CN
P34-298 CHF2 0
P34-280 CHF2 CH2CN
P34-281 CHF2 CHO
P34-282 CHF2 COMe P34-299 CHF2 0
P34-283 CHF2 C02Me
P34-284 CHF2 CH2CHO 0
P34-285 CHF2 CH2COMe P34-300 CHF2
P34-286 CHF2 CH2C02Me
# O—
P34-287 CHF2
P34-301 CHF2
P34-288 CHF2 # o-cF3
P34-302 CHF2
P34-289 CHF2
#
P34-290 CHF2
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
R4a are the possible substituents for the the acyclic moieties of R4 and the R4a are in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(C C4-alkyl), N(C C4-alkyl)2, NH(C(=0)CrC4-alkyl), N(C(=0)C C4-alkyl)2, NH-S02-R*, C C6-alkoxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6- alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), CR'=NOR", heterocarbocycle, aryl and phenoxy, wherein the aryl and phenyl groups are independently unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4- alkoxy, Ci-C4-halogenalkoxy and S(0)n-Ci-C6-alkyl, wherein in each case one or two CH2 groups of the heterocycle may be replaced by a group independently selected from C(=0) or C(=S), and wherein the heterocycle contain independently one, two, three or four heteroatoms selected from N, O or S;
According to one preferred embodiment, R4a is in each case independently selected from halogen, OH, CN, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl) and CR'=NOR". According to one preferred embodiment, R4a is in each case independently selected from OH, CN, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl) such as CN, CHO, C(0)0(CH3) ,C02NH(CH3) or C02N(CH3)2.
According to one preferred embodiment, R4a is in each case independently selected from C1-C6- alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, such as SCH3, S02CH3, S02Ph.
According to one preferred embodiment, R4a is in each case independently selected from NH(CrC4-alkyl), N(C C4-alkyl)2, NH-S02-R*, such as NH(CH3), N(CH3)2 or NHS02CH3, NHS02CF3.
According to one preferred embodiment, R4a is in each case independently selected from C3-C6- cycloalkyl, C3-C6-halogencycloalkyl, such as cyclopropyl or fully or partially halogenated cyclo- propyl.
According to one preferred embodiment, R4a is in each case independently selected from C1-C6- alkoxy, Ci-C6-halogenalkoxy, such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to one preferred embodiment, R4a is in each case independently selected from heter- ocarbocycle, wherein the heretocyclocycle is a satureated, two CH2 groups are replaced by C(=0) and contains one N as a ring member.
According to one preferred embodiment, R4a is in each case independently selected from aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH3, CHF2, OCH3, OCHFs, CN or S02CH3.
According to one preferred embodiment, R4a is in each case independently selected from halogen, OH, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and heterocycle, wherein the heretocyclocycle is a satureated and contains one N as a ring member.
According to one preferred embodiment, R4a is in each case independently selected from halo- gen, OH, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and heterocycle, wherein the heretocyclocycle is a satureated, one CH2 group is replaced by C(=0) and contains one N as a ring member.
According to one preferred embodiment, R4a is in each case independently selected from halogen, OH, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and heterocycle, wherein the heretocy- clocycle is a satureated, two CH2 groups are replaced by C(=0) and contains one N as a ring member.
According to one preferred embodiment, R4a is in each case independently selected from halogen, OH, CN, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, phenyl and aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH3, CHF2, OCH3, OCHF3, CN or S02CH3. According to one further preferred embodiment, R4a is in each case independently selected from halogen, phenyl and halogenphenyl, wherein the halogenphenyl is substituted by halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
According to one further preferred embodiment, R4a is in each case independently selected from halogen, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci- C6-alkylthio, Ci-C6-halogenalkylthio, phenyl, wherein the phenyl is substituted by halogen selected from the group consisting of F, CI and Br or by Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy. According to one further preferred embodiment, R4a is in each case independently selected from halogen and phenyl wherein the phenyl is substituted by hal- ogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
R4b are the possible substituents for the carbocycle, heterocycle, heteroaryl and aryl moieties and are independently selected from halogen, OH, CN, N02, SH, NH2, NH(C C4-alkyl), N(C C4- alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-R*, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phe- noxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.
According to one preferred embodiment, R4b is in each case independently selected from halo- gen, OH, CN, SH, Ci-C6-alkyl, Ci-C6-halogenalkyl, CrC6-alkoxy, CrC6-halogenalkoxy, CrC6- alkylthio and S(0)n-Ci-C6-alkyl. According to one further preferred embodiment, R4b is in each case independently selected from halogen, Ci-C6-alkoxy, Ci-C6-halogenalkyl, Ci-C6-halogen- alkoxy and S(0)n-Ci-C6-alkyl. According to one further particular embodiment, R4b is in each case independently selected from Ci-C6-alkyl, such as methyl and ethyl. According to one fur- ther particular embodiment, R4b is in each case independently selected from halogen, such as F, CI and Br. According to one further particular embodiment, R4b is in each case independently selected from Ci-C6-alkoxy, such as OCH3. According to one further particular embodiment, R4b is in each case independently selected from Ci-C4-halogenalkoxy, such as OCHF2 and OCF3. According to one further particular embodiment, R4b is in each case independently selected from S(0)n-Ci-C6-alkyl. such as S02CH3.
R5 is H.
R6 is H.
A is selected from below group:
Figure imgf000057_0001
Figure imgf000058_0001
wherein, the positions of the rings marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I.
According to one preferred embodiment, A is
Figure imgf000058_0002
According to one preferred embodiment, A is
Figure imgf000058_0003
According to one preferred embodiment, A is
Figure imgf000058_0004
Y is H.
R78 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N, O and S and wherein the acyclic moieties of R78 are unsubstituted or substituted by R78a which independently of one another are selected from:
halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the het- eroaryl, phenyl and phenoxy group is unsubstituted or substituted by R78aa selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubstituted or substituted by R78b which independently of one another are selected from:
R78b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio.
According to still another embodiment of formula l,o is 0.
According to still another embodiment of formula I , o is 1.
According to still another embodiment of formula I , o is 2 or 3. According to one specific embodiment thereof, o is 2. According to still another embodiment of formula I, o is 3.
For every R78 that is present in the compounds of formula I , the following embodiments and preferences apply independently of the meaning of any other R78 that may be present in the ring. Furthermore, the particular embodiments and preferences given herein for R78 apply inde- pendently for each of o=1 , o=2 and o=3.
According to one embodiment of formula I , R78 is selected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy.
According to one embodiment of formula I , R78 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
According to still another embodiment of formula I , R78 is F.
According to still another embodiment of formula I , R78 is CI.
According to still another embodiment of formula I , R78 is Br.
According to still another embodiment of formula I , R78 is OH .
According to still another embodiment of formula I , R78 is CN.
According to still another embodiment of formula I , R78 is NO2.
According to still another embodiment of formula I , R78 is SH.
According to still another embodiment of formula I , R78 is NH2.
According to still another embodiment of formula I , R78 is , NH(Ci-C4-alkyl), in particular
NH(CH3), NH(C2H5).
According to still another embodiment of formula I , R78 is , N(Ci-C4-alkyl)2, in particular
NH(CH3)2, NH(C: According to still another embodiment of formula I, R78 is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH3), NH(C(=0)(C2H5).
According to still another embodiment of formula I, R78 is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH3)2, N(C(=0)(C2H5)2.
According to a further specific embodiment of formula I, R78 is NH-S02-RX such as NH-SO2-CH3, NH-SO2-CH2-CH3, NH-SO2-CF3 or NH-SOz-Ts.
According to a further specific embodiment of formula I, R78 is CH(=0), C(=0)CrC6-alkyl, C(=0)0(Ci-C6-alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n- butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R78 is CR'=NOR" such as
C(CH3)=NOCH3, C(CH3)=NOCH2CH3 or C(CH3)=NOCF3.
According to still another embodiment of formula I, R78 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3.
According to still another embodiment of formula I, R78 is CH2CH3.
According to still another embodiment of formula I, R78 is CrC6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment of formula I, R78 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2 or CH2 CH=CH2
According to a further specific embodiment of formula I, R78 is C2-C6-halogenalkenyl, in particu- lar C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2. CH2CF=CF2, CH2CCI=CCI2. CF2CF=CF2 or CCI2CCI=CCI2.
According to still a further embodiment of formula I, R78 is C2-C6-alkynyl or C2-C6-halogen- alkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2- C CH, C≡CCI, CH2- C≡CCI, or CCI2- C≡CCI.
According to a further specific embodiment of formula I, R78 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to a further specific embodiment of formula I, R78 is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCIs, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, R78 is C2-C6-alkenyloxy, in particular C2- C4-alkenyloxy, more specifically Ci-C2-alkenyloxy such as OCH=CH2, OCH2CH=CH2.
According to a further specific embodiment of formula I, R78 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH, OChbC CH.
According to still another embodiment of formula I R78 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I, R78 is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl. According to one embodiment, R78 is C3-C6-cycloalkyl, such as a 4-membered saturated carbo- cycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by
R78b
According to one embodiment, R78 is C3-C6-cycloalkyl, such as a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by
R78b.
According to one embodiment, R78 is a C3-C6-cycloalkyl, such as 6-membered saturated carbo- cycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by
R78b
According to still another embodiment of formula I R78 is C3-C6-cycloalkenyl, in particular cyclo- propenyl.
According to still another embodiment of formula I R78 is S(0)n-Ci-C6-alkyl such as SCH3, S(=0) CH3, S(0)2CH3.
According to still another embodiment of formula I, R78 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R78b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, R78 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R78b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, in the embodiments of R78 described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
According to one embodiment, R78 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by R78b.
According to still another embodiment of formula I, R78 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroa- torn. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by R78b.
According to still another embodiment of formula I, R78 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by R78b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by R78b. According to still another embodiment of formula I, R78 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R78b which independently of one another are selected from halogen, OH, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br, CH3, OCH3, CHF2, CF3 OCHF2, and OCF3.
According to still another embodiment of formula I, R78 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R78b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, CHF2, OCH3, OCHF2, CF3 and OCF3. According to one embodiment, R78 is unsubstituted phenyl. According to another embodiment, R78 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to still another embodiment of formula I, R78 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R78 is a 6-membered heteroaryl, such as pyr- idin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to still another embodiment of formula I, R78 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3- C6-alkynyloxy, C3-C6-cycloalkyl, three-, four-, five- or six-membered saturated or partially un- saturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the carbo- and heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a as defined and preferably defined herein, and wherein the heterocyclic, alicyclic, phenyl and heteroaryl moieties of R78 are unsubstituted or substituted with identical or different groups R78b as defined and preferably defined herein.
According to still another embodiment of formula I, R78 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a as defined and preferably defined herein, and wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubstituted or substituted with identical or different groups R78b as defined and preferably defined herein. Accordingto one specific embodiment, the acyclic and cyclic moieties of R78 are unsubstituted, according to another embodiment, the acyclic moieties of R78 substituted with identical or different groups R78a as defined and preferably defined herein.
According to still another embodiment of formula I , R78 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3- C6-alkynyloxy and C3-C6-cycloalkyl, wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a as defined and preferably defined herein, and wherein the cycloalkyl moieties of R78 are unsubstituted or substituted with identical or different groups R78b as defined and preferably defined herein.
According to still another embodiment of formula I , R78 is in each case independently selected from halogen, Ci-C6-alkyl and Ci-C6-alkoxy, wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a defined and preferably defined herein. According to still another embodiment of formula I , R78 is in each case independently selected from halogen, Ci-C6-alkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a defined and preferably defined herein. According to one specific embodiment, the acyclic and cyclic moieties of R78 are not further substituted, according to another embodiment, the acyclic moieties of R78 carry one, two, three or four identical or different groups R78a as defined and preferably defined herein.
R78a are the possible substituents for the acyclic moieties of R78. R78a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogengenalkoxy, Ci-C6-alkylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R78a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy.
According to one preferred embodiment, R78a is in each case independently selected from Ci- Ce-alkoxy, Ci-C6-halogenalkoxy, such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to one preferred embodiment, R78a is in each case independently selected from C3- C6-cycloalkyl, C3-C6-halogencycloalkyl, such as cyclopropyl or fully or partially halogenated cy- clopropyl.
According to still another embodiment of formula I , R78a is a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyra- zol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxa- zol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4- yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1-yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R78a is a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to one preferred embodiment, R78a is in each case independently selected from aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH3, CHF2, OCH3, OCHF3, CN or SO2CH3.
According to one embodiment R78a is independently selected from halogen, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R78a is independently selected from CN, F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl , 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I, R78a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
R78b are the possible substituents for the C3-C6-cycloalkyl, heterocyclyl, heteroaryl and phenyl moieties of R78. R78b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment thereof R78b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R78b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
Particularly preferred embodiments of the A ring, optionally substituted by (R78)0, according to the invention are in Table P78 below, wherein each line of lines P78-1 to P78-40corresponds to one particular embodiment of the invention, wherein P78-1 to P78-40 are also in any combination with one another a preferred embodiment of the present invention. Thereby, the positions of the pheny marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I:
Figure imgf000064_0001
wherein A is selected from below group
Figure imgf000065_0001
Table P78: No. (R78)o
No. (R78)o P78-27 2'-CN
P78-1 o = 0 P78-28 3'-F
P78-2 r-F P78-29 3 -CI
P78-3 r-ci P78-30 3'-Br
P78-4 r-Br P78-31 3'-CH3
P78-5 r-CH3 P78-32 3 -C2H5
P78-6 1 -C2H5 P78-33 3'-CH2F
P78-7 1 -CH2F P78-34 3'-CHF2
P78-8 1 -CHF2 P78-35 3'-CF3
P78-9 r-CFs P78-36 3'-OCH3
P78-10 1 -OCH3 P78-37 3'-OCH2F
P78-11 1 -OCH2F P78-38 3'-OCHF2
P78-12 1 -OCHF2 P78-39 3'-OCF3
Figure imgf000065_0002
P78-13 r-ocFs P78-40 3'-CN R9 is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H2, N H(Ci- C4-alkyl), N(Ci-C4-alkyl)2, N H (C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4-al- kynyl)2, N H(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-al- kyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4- alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl), N H(C(=0)Ci-C4-alkyl),
N(C(=0)CrC4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CrC6-cycloalkylthio, S(0)n-C2- Ce-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)CrC6-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6- alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)N H(Ci-C6-alkyl), CH(=S) , C(=S)Ci-C6-alkyl, C(=S)C2-C6- alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S;
wherein
Rx is as defined above;
RY is CrC6-alkyl, CrC6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl;
wherein the acyclic moieties of R9 are unsubstituted or substituted by groups R9a which independently of one another are selected from:
R9a halogen, OH , CN , Ci-Ce-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is un- substituted or substituted by substituents R91 a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;
wherein the carbocycle, heteroaryl and aryl moieties of R9 are unsubstituted or
substituted by groups R9b which independently of one another are selected from: R9b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cyclo- alkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
According to one embodiment of formula I , R9 is selected from the group consisting of H , halogen, CN , Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogency- cloalkyl, and ORY.
According to one embodiment of formula I , R9 is H .
According to still another embodiment of formula I , R9 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
According to still another embodiment of formula I , R9 is F.
According to still another embodiment of formula I , R9 is CI.
According to still another embodiment of formula I , R9 is Br.
According to still another embodiment of formula I , R9 is OH .
According to still another embodiment of formula I , R9 is CN .
According to still another embodiment of formula I , R9 is NO2. According to still another embodiment of formula I, R9 is SH.
According to still another embodiment of formula I, R9 is NH2.
According to still another embodiment of formula I, R9 is , NH(Ci-C4-alkyl), in particular NH(CH3), NH(C2H5).
According to still another embodiment of formula I, R9 is , N(Ci-C4-alkyl)2, in particular NH(CH3)2, NH(C2H5)2.
According to still another embodiment of formula I, R9 is , NH(C2-C4-alkenyl), in particular NH(CH=CH2), NH(CH2CH=CH2).
According to still another embodiment of formula I, R9 is , N(C2-C4--alkenyl)2, in particular N(CH=CH2)2, N(CH2CH=CH2)2.
According to still another embodiment of formula I, R9 is , NH(C2-C4-alkynyl), in particular NH(C= CH), NH(CH2C≡CH).
According to still another embodiment of formula I, R9 is , N(C2-C4-alkynyl)2, in particular N(C= CH)2, N(CH2C≡CH)2.
According to still another embodiment of formula I, R9 is , NH(C3-C6-cycloalkyl), in particular NH(C3H7), NH(C4H9).
According to still another embodiment of formula I, R9 is , N(C3-C6-cycloalkyl)2, in particular N(C3H7)2, N(C4H9)2.
According to still another embodiment of formula I, R9 is N(Ci-C4-alkyl)(C2-C4-alkenyl), in particular N(CH3)(CH=CH2), N(CH3)(CH2CH=CH2), N(C2H5)(CH=CH2), N(C2H5)(CH2CH=CH2).
According to still another embodiment of formula I, R9 is N(Ci-C4-alkyl)(C2-C4-alkynyl), in particular N(CH3)(C≡CH), N(CH3)(CH2C≡CH), N(C2H5)(C≡CH), N(C2H5)(CH2C≡CH).
According to still another embodiment of formula I, R9 is N(CrC4-alkyl)(C3-C6-cycloalkyl), in particular N(CH3)(C3H7), N(CH3)(C4H9), N(C2H5)(C3H7), N(CH3)(C4H9).
According to still another embodiment of formula I, R9 is N(C2-C4-alkenyl)(C2-C4-alkynyl), in particular N(CH=CH2)(C≡CH), N(CH2CH=CH2)(CH2C≡CH), N(CH=CH2)(C≡CH),
N(CH2CH=CH2)(CH2C≡CH).
According to still another embodiment of formula I, R9 is N(C2-C4-alkenyl)(C3-C6-cycloalkyl), in particular N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9), N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9). According to still another embodiment of formula I, R9 is N(C2-C4-alkynyl)(C3-C6-cycloalkyl), in particular N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9), N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9).
According to still another embodiment of formula I, R9 is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH3), NH(C(=0)(C2H5).
According to still another embodiment of formula I, R9 is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH3)2, N(C(=0)(C2H5)2.
According to a further specific embodiment of formula I, R9 is NH-S02-RX such as NH-SO2-CH3, NH-SO2-CH2-CH3, NH-SO2-CF3, NH-SO2-TS. According to still another embodiment of formula I , R9 is S(0)n-Ci-C6-alkyl such as SCH3, S(=0) CH3, S(0)2CH3.
According to still another embodiment of formula I , R9 is S(0)n-aryl such as S-phenyl, S(=0) phenyl, S(0)2phenyl.
According to still another embodiment of formula I , R9 is S(0)n-C2-C6-alkenyl such as
SCH=CH2, S(=0)CH=CH2, S(0)2CH=CH2, SCH2CH=CH2, S(=0)CH2CH=CH2,
S(0)2CH2CH=CH2 .
According to still another embodiment of formula I , R9 is S(0)n-C2-C6-alkynyl such as SC CH, S(=0)C≡CH, S(0)2C≡CH, SCH2C≡CH, S(=0)CH2C≡CH, S(0)2CH2C≡CH.
According to a further specific embodiment of formula I , R9 is CH(=0).
According to a further specific embodiment of formula I , R9 is C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6- alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I , R9 is C(=0)C2-C6-alkenyl, C(=0)0(C2- Ce-alkenyl) or C(=0)NH(C2-C6-alkenyl), wherein alkenyl is CH=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I , R9 is C(=0)C2-C6-alkynyl, C(=0)0(C2- Ce-alkynyl) or C(=0)NH(C2-C6-alkynyl), wherein alkynyl is C≡CH, CH2C≡CH.
According to a further specific embodiment of formula I , R9 is C(=0)C3-C6-cycloalkyl,
C(=0)0(C3-C6-cycloalkyl) or C(=0)NH(C3-C6-cycloalkyl), wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).
According to a further specific embodiment of formula I , R9 is CH(=S).
According to a further specific embodiment of formula I , R9 is C(=S)Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I , R9 is C(=S)C2-C6-alkenyl, wherein alkenyl is CH=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I , R9 is C(=S)C2-C6-alkynyl, wherein alkynyl is C≡CH, CH2C≡CH.
According to a further specific embodiment of formula I , R9 is C(=S)C3-C6-cycloalkyl, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C H9).
According to a further specific embodiment of formula I , R9 is C(=S)NHCrC6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I , R9 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.
According to still another embodiment of formula I , R9 is Ci-C6-halogenalkyl, in particular Ci-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment of formula I , R9 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I , R9 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.
According to still a further embodiment of formula I , R9 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, Ch C CH, C CCI,
CH2C≡CCI, or CCI2C≡CCI.
According to a further specific embodiment of formula I , R9 is ORY wherein RY is Ci-C6-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl.
According to a further specific embodiment of formula I , R9 is ORY, wherein RY is Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically Ci-C2-alkoxy. R9 is such as OCH3 or OCH2CH3.
According to a further specific embodiment of formula I , R9 is ORY, wherein RY is Ci-C6-halogen- alkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl. R9 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2. According to a further specific embodiment of formula I , R9 is ORY wherein RY C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl. R9 is such as OCH=CH2,
OCH2CH=CH2.
According to a further specific embodiment of formula I , R9 is ORY, wherein RY C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl. R9 is such as OC≡CH, OC≡CCI, OCH2C≡CCI, or OCCI2C≡CCI.
According to still another embodiment of formula I R9 is ORY, wherein RY is C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I , R9 is ORY wherein RY is C3-C6-halogencyclo- alkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I , R9 is is ORY, wherein RY C3-C6-cycloalkenyl, in particular cyclopropenyl.
According to still another embodiment of formula I , R9 is C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I , R9 is C3-C6-halogencycloalkyl. In a special embodiment R9b is fully or partially halogenated cyclopropyl, such as 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 , 1 -Cl2-cyclopropyl .
According to still another embodiment of formula I , R9 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R9b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R9 is unsubstituted phenyl. According to another embodiment, R9 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI. According to still another embodiment of formula I, R9 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R9 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to still another embodiment of formula I, R9 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R9 are unsubstituted or substituted with iden- tical or different groups R9a as defined and preferably defined herein, and wherein the carbocy- clic, phenyl and heteroaryl moieties of R9 are unsubstituted or substituted with identical or different groups R9b as defined and preferably defined herein.
According to still another embodiment of formula I, R9 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl,, wherein the acyclic moieties of R9 are unsubstituted or substituted with identical or different groups R9a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R9 are unsubstituted or substituted with identical or different groups R9b as defined and preferably defined herein.
R9a are the possible substituents for the acyclic moieties of R9.
According to one embodiment R9a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.
According to one embodiment R9a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R9a is independently selected from F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1 -F2- cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I, R9a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
R9b are the possible substituents for the cycloalkyi, heteroaryl and phenyl moieties of R9. R9b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
According to one embodiment thereof R9b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R9b is independently selected from F, CI, CN , CH3, OCH3 and halogenmethoxy.
Particularly preferred embodiments of R9 according to the invention are in Table P13 below, wherein each line of lines P13-1 to P3-43 corresponds to one particular embodiment of the invention, wherein P13-1 to P3-43 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R9 is bound is marked with "#" in the drawings. Table P13:
Figure imgf000071_0002
Figure imgf000071_0001
Figure imgf000072_0001
R10 is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H2, N H(Ci- C4-alkyl), N(CrC4-alkyl)2, N H (C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4-al- kynyl)2, N H(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-al- kyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4- alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl), N H(C(=0)Ci-C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, Ci-Ce-cycloalkylthio, S(0)n-C2- Ce-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6- alkynyl, C(=0)C3-C6-cyclpalkyl, C(=0)N H(Ci-C6-alkyl), CH(=S) , C(=S)Ci-C6-alkyl, C(=S)C2-C6- alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cyclpalkyl, C(=S)N H(CrC6-alkyl), CrC6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S;
wherein
Rx is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl;
wherein the acyclic moieties of R10 are unsubstituted or substituted by groups R10a which independently of one another are selected from:
R10a halogen, OH , CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R101 a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R10 are unsubstituted or
substituted by groups R10b which independently of one another are selected from:
R10b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, C C4-halogenalkyl, C3-C6-cyclo- alkyl, C3-C6-halogencycloalkyl, CrC4-halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment of formula I, R10 is in each case independently selected from halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C2-C4-alkenyl), N(C2-C4- alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4-alkynyl)2, N H(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-alkyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cy- cloalkyl), N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, Ci-Ce-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)C C6-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cyclpalkyl, C(=0)N H(C C6-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cyclpalkyl, C(=S)NH(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroa- toms selected from N, O and S; wherein
Rx is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl;
wherein the acyclic moieties of R10 are unsubstituted or substituted by groups R10a which independently of one another are selected from:
R10a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-
C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R101a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;
wherein the cycloalkyl, heteroaryl and aryl moieties of R10 are unsubstituted or
substituted by groups R10b which independently of one another are selected from:
R10b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cyclo- alkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R10 is secected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2- C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-hal ogenalkoxy and ORY.
According to still another embodiment of formula I, R10 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
According to still another embodiment of formula I , R10 is F.
According to still another embodiment of formula I , R10 is CI.
According to still another embodiment of formula I , R10 is Br.
According to still another embodiment of formula I , R10 is OH.
According to still another embodiment of formula I , R10 is CN.
According to still another embodiment of formula I , R10 is N02.
According to still another embodiment of formula I , R10 is SH.
According to still another embodiment of formula I , R10 is NH2.
According to still another embodiment of formula I , R10 is , NH(C
NH(CH3), NH(C2H5).
According to still another embodiment of formula I , R10 is , N(Ci-
NH(CH3)2, NH(C2H5)2.
According to still another embodiment of formula , NH(C2-C4-alkenyl), in particular NH(CH=CH2), NH(CH2CH=CH2).
According to still another embodiment of formula I, R10 is , N(C2-C4--alkenyl)2, in particular
N(CH=CH2)2, N(CH2CH=CH2)2.
According to still another embodiment of formula I, R10 is , NH(C2-C4-alkynyl), in particular NH(C ≡CH), NH(CH2C≡CH).
According to still another embodiment of formula I, R10 is , N(C2-C4-alkynyl)2, in particular N(C= CH)2, N(CH2C≡CH)2.
According to still another embodiment of formula I, R10 is , NH(C3-C6-cycloalkyl), in particular NH(C3H7), NH(C4H9).
According to still another embodiment of formula I, R10 is , N(C3-C6-cycloalkyl)2, in particular N(C3H7)2, N(C4H9)2.
According to still another embodiment of formula I, R10 is N(Ci-C4-alkyl)(C2-C4-alkenyl), in particular N(CH3)(CH=CH2), N(CH3)(CH2CH=CH2), N(C2H5)(CH=CH2), N(C2H5)(CH2CH=CH2).
According to still another embodiment of formula I, R10 is N(Ci-C4-alkyl)(C2-C4-alkynyl), in particular N(CH3)(C≡CH), N(CH3)(CH2C≡CH), N(C2H5)(C≡CH), N(C2H5)(CH2C≡CH).
According to still another embodiment of formula I, R10 is N(Ci-C4-alkyl)(C3-C6-cycloalkyl), in particular N(CH3)(C3H7), N(CH3)(C4H9), N(C2H5)(C3H7), N(CH3)(C4H9).
According to still another embodiment of formula I, R10 is N(C2-C4-alkenyl)(C2-C4-alkynyl), in particular N(CH=CH2)(C≡CH), N(CH2CH=CH2)(CH2C≡CH), N(CH=CH2)(C≡CH),
N(CH2CH=CH2)(CH2C≡CH).
According to still another embodiment of formula I, R10 is N(C2-C4-alkenyl)(C3-C6-cycloalkyl), in particular N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9), N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9).
According to still another embodiment of formula I, R10 is N(C2-C4-alkynyl)(C3-C6-cycloalkyl), in particular N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9), N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9).
According to still another embodiment of formula I, R10 is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH3), NH(C(=0)(C2H5).
According to still another embodiment of formula I, R10 is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH3)2, N(C(=0)(C2H5)2.
According to a further specific embodiment of formula I, R10 is NH-S02-Rx such as NH-S02- CH3, NH-S02-CH2-CH3, NH-S02-CF3, NH-S02-Ts.
According to still another embodiment of formula I, R10 is S(0)n-Ci-C6-alkyl such as SCH3, S(=0) CH3, S(0)2CH3.
According to still another embodiment of formula I, R10 is S(0)n-aryl such as S-phenyl, S(=0) phenyl, S(0)2phenyl.
According to still another embodiment of formula I, R10 is S(0)n-C2-C6-alkenyl such as
SCH=CH2, S(=0)CH=CH2, S(0)2CH=CH2, SCH2CH=CH2, S(=0)CH2CH=CH2,
S(0)2CH2CH=CH2 . According to still another embodiment of formula I, R10 is S(0)n-C2-C6-alkynyl such as SC CH, S(=0)C≡CH, S(0)2C≡CH, SCH2C≡CH, S(=0)CH2C≡CH, S(0)2CH2C≡CH.
According to a further specific embodiment of formula I, R10 is CH(=0).
According to a further specific embodiment of formula I, R10 is C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6- alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R10 is C(=0)C2-C6-alkenyl, C(=0)0(C2- Ce-alkenyl) or C(=0)NH(C2-C6-alkenyl), wherein alkenyl is CH=CH2, C(CH3)=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R10 is C(=0)C2-C6-alkynyl, C(=0)0(C2- Ce-alkynyl) or C(=0)NH(C2-C6-alkynyl), wherein alkynyl is C≡CH, CH2C≡CH,
According to a further specific embodiment of formula I, R10 is C(=0)C3-C6-cycloalkyl,
C(=0)0(C3-C6-cycloalkyl) or C(=0)NH(C3-C6-cycloalkyl), wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).
According to a further specific embodiment of formula I, R10 is CH(=S).
According to a further specific embodiment of formula I, R10 is C(=S)CrC6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R10 is C(=S)C2-C6-alkenyl, wherein alkenyl is CH=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R10 is C(=S)C2-C6-alkynyl, wherein al- kynyl is C≡CH, CH2C≡CH.
According to a further specific embodiment of formula I, R10 is C(=S)C3-C6-cycloalkyl, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).
According to a further specific embodiment of formula I, R10 is C(=S)NHCrC6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I, R10 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.
According to still another embodiment of formula I, R10 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment of formula I, R10 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2.
According to a further specific embodiment of formula I, R10 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.
According to still a further embodiment of formula I, R10 is C2-C6-alkynyl or C2-C6-halogen- alkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2 C CH, C CCI, CH2C≡CCI, or CCI2C≡CCI.
According to a further specific embodiment of formula I, R10 is ORY wherein RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-al kynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl.
According to a further specific embodiment of formula I, R10 is ORY, wherein RY is Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically Ci-C2-alkoxy. R10 is such as OCH3 or OCH2CH3.
According to a further specific embodiment of formula I, R10 is ORY, wherein RY is Ci-C6-halo- genalkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl. R10 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, R10 is ORY, wherein RY C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl. R10 is such as OCH=CH2,
OCH2CH=CH2.
According to a further specific embodiment of formula I, R10 is ORY, wherein RY C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl. R10 is such as OC≡CH, OC≡CCI, OCH2C≡CCI, or OCCI2C≡CCI According to still another embodiment of formula I R10 is ORY wherein RY is C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I, R10 is ORY, wherein RY is C3-C6-halogency- cloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R10 is is ORY, wherein RY C3-C6-cycloalkenyl, in particular cyclopropenyl.
According to still another embodiment of formula I, R10 is C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I, R10 is C3-C6-halogencycloalkyl. In a special embodiment R10b is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl
According to still another embodiment of formula I, R10 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R10b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R10 is unsubstituted phenyl. According to another embodiment, R10 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to still another embodiment of formula I, R10 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl. According to still another embodiment of formula I , R9 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to still another embodiment of formula I , R10 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy,C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R10 are unsubstituted or substituted with identical or different groups R10a as defined and preferably defined herein, and wherein the carbocy- clic, phenyl and heteroaryl moieties of R10 are unsubstituted or substituted with identical or dif- ferent groups R10b as defined and preferably defined herein.
According to still another embodiment of formula I , R10 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R10 are unsubstituted or substituted with iden- tical or different groups R10a as defined and preferably defined herein, and wherein the cycloal- kyl moieties of R10 are unsubstituted or substituted with identical or different groups R10b as defined and preferably defined herein.
R10a are the possible substituents for the acyclic moieties of R9.
According to one embodiment R10a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.
According to one embodiment R10a is independently selected from halogen, Ci-C6-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R10a is
independently selected from F, CI, Br, I , Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1-CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I , R10a is independently halogen, in particular selected from F, CI, Br and I , more specifically F, CI and Br.
R10b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R10. R10b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
According to one embodiment thereof R10b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R10b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
Particularly preferred embodiments of R10 according to the invention are in Table P14 below, wherein each line of lines P14-1 to P14-43 corresponds to one particular embodiment of the in- vention, wherein P14-1 to P14-43 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R10 is bound is marked with "#" in the drawings.
Table P14:
Figure imgf000078_0001
Figure imgf000078_0002
According to still another embodiment of formula I, R9, R10 together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaro- matic ring; wherein the heterocyclic or heteroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci- C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted by substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R11)m wherein m is 0, 1 , 2, 3 or 4;
RN is the substituent of the heteroatom N that is contained in the heterocycle formed by R9 and R10 in some of the inventive compounds. RN is selected from Ci-C4-alkyl, Ci-C4-halogen- alkyl and SC>2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from Ci-C4-alkyl. In one preferred embodiment, RN is in each case independently selected from Ci-C2-alkyl, Ci-C2-halogenalkyl and SC>2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl substituents. In one particular embod- iment, RN is in each case independently selected from Ci-C2-alkyl, more particularly methyl. In one particular embodiment, RN is in each case independently selected from S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl.
According to still another embodiment of formula I, R9 and R10 together with the carbon atoms to which they are bound form a saturated or partially unsaturated five-, six-or seven -membered carbo- and heterocycle that is unsubstituted or substituted.
According to one embodiment, R9 and R10 form a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 7-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 3-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 4-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11. According to one embodiment, R9 and R10 form a 5-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 6-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 7-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 5-membered saturated heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 6-membered heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
R11 according to the invention is in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-C6-alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx11 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R11 are unsubstituted or substituted with identical or different groups R11a which independently of one another are selected from:
R11a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci-C4-halo- genalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl of R11 are unsubstituted or substituted with identical or different groups R11b which independently of one another are selected from:
R11b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
For every R11 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R11 that may be present in the ring.
According to one embodiment of formula I, wherein m is 0, 1 , 2, 3 or 4. According to still another embodiment of formula l,m is 0.
According to still another embodiment of formula I, m is 1 .
According to still another embodiment of formula I, m is 2 or 3. According to one specific embodiment thereof, m is 2. According to still another embodiment of formula I, m is 3.
According to one embodiment of formula I, R11 is halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci- Ce-alkoxy or , C C6-halogenalkoxy, in particular CH3, Et, CHF2, OCH3, OCHF2, OCF3, F, CI, more specifically H, CH3, F or CI most preferred F or CI.
According to still another embodiment of formula I, R11 is halogen, in particular Br, F or CI, more specifically F or CI.
According to still another embodiment of formula I, R11 is OH.
According to still another embodiment of formula I, R11 is CN.
According to still another embodiment of formula I R11 is Nhb, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-RX, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx11 independently selected from Ci-C4-al- kyl.
According to still another embodiment of formula I, R11 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3.
According to still another embodiment of formula I, R11 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2 or CH2CI.
According to still another embodiment of formula I, R11 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, C(CH3)=CH2,
CH2CH=CH2, CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CF=CF2, CCI=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CH2CF=CF2, CH2CCI=CCI2, CF2CF=CF2 or
CCI2CCI=CCI2.
According to still another embodiment of formula I, R11 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, CH2C≡CH, C≡C-CI, C≡C- CH3, CH2C≡CH, CH2C≡CCI or CH2C≡C-CH3.
According to still another embodiment of formula I, R11 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I, R11 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to still another embodiment of formula I R11 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I, R11 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R11b as defined and preferably herein.
According to still another embodiment of formula I, R11 is C3-C6-halogencycloalkyl. In a special embodiment R11 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R11 is unsubstituted aryl or aryl that is substituted by one, two, three or four R11b, as defined herein. In particular, R11 is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R11 b, as defined herein.
According to still another embodiment of formula I, R11 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R11 is 5- or 6-membered heteroaryl that is substituted by one, two or three R11b, as defined herein.
According to still another embodiment of formula I, R11 is in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R11 are not further substituted or carry one, two, three, four or five identical or different groups R11a as defined below and wherein the carbocyclic, heterocyclic and heteroaryl moieties of R11 are not further substituted or carry one, two, three, four or five identical or different groups R11 b as defined below.
According to still another embodiment of formula I, R11 is independently selected from halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
R11a are the possible substituents for the acyclic moieties of R11.
R11a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, CrC4-halogenalkyl, CrC4-alkoxy, Ci-C4- halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio.
R11a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, Ci-C2- alkoxy, Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
In to one embodiment R11a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R11a is
independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-CI2-cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R11a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I, R11a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R11a is
independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
R11b are the possible substituents for the carbocyclic, heterocyclic and heteroaryl moieties of R11.
R11 b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R11 b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-hal- ogenalkoxy. Specifically, R11 b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 , 1 -F2-cyclopropyl, 1 , 1 -Cl2-cyclopropyl and halogenmethoxy.
According to still another embodiment thereof R11 b is independently selected from Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogen- alkoxy. Specifically, R11 b is independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F- cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 - Cl-cyclopropyl, 1 , 1 -F2-cyclopropyl, 1 , 1 -Cl2-cyclopropyl cyclopropyl and OCHF2.
Particularly preferred embodiments of combinations of R9 and R10 according to the invention are in Table P35 below, wherein each line of lines P35-1 to P35-305 corresponds to one particular embodiment of the invention, wherein P35-1 to P35-305 are also in any combination with one another a preferred embodiment of the present invention. The carbon atom, to which R9 bound is marked with * in the drawings and the carbon atom, to which R10 is bound is marked with # in the drawings. cPr stands for cyclopropyl.
Table P35:
Figure imgf000083_0001
line R9 R10 line R9 R10
P35-25 F CHF2 P35-55 Br Br
P35-26 F CFs P35-56 Br CHs
P35-27 F OCHs P35-57 Br CH2CH3
P35-28 F OChbF P35-58 Br CH2F
P35-29 F OCHF2 P35-59 Br CHF2
P35-30 F OCFs P35-60 Br CFs
P35-31 F cPr P35-61 Br OCHs
P35-32 F C≡CH P35-62 Br OCH2F
P35-33 F CN P35-63 Br OCHF2
P35-34 F S-CHs P35-64 Br OCFs
P35-35 CI H P35-65 Br cPr
P35-36 CI F P35-66 Br C≡CH
P35-37 CI CI P35-67 Br CN
P35-38 CI Br P35-68 Br S-CHs
P35-39 CI CHs P35-69 CHs H
P35-40 CI CH2CH3 P35-70 CHs F
P35-41 CI CH2F P35-71 CHs CI
P35-42 CI CHF2 P35-72 CHs Br
P35-43 CI CFs P35-73 CHs CHs
P35-44 CI OCHs P35-74 CHs CH2CH3
P35-45 CI OCH2F P35-75 CHs CH2F
P35-46 CI OCHF2 P35-76 CHs CHF2
P35-47 CI OCFs P35-77 CHs CFs
P35-48 CI cPr P35-78 CHs OCHs
P35-49 CI C≡CH P35-79 CHs OCH2F
P35-50 CI CN P35-80 CHs OCHF2
P35-51 CI S-CHs P35-81 CHs OCFs
P35-52 Br H P35-82 CHs cPr
P35-53 Br F P35-83 CHs C≡CH
P35-54 Br CI P35-84 CHs CN line R9 R10 line R9 R10
P35-85 CHs S-CH3 P35-1 15 CH2F OCF3
P35-86 CH2CH3 H P35-1 16 CH2F cPr
P35-87 CH2CH3 F P35-1 17 CH2F C≡CH
P35-88 CH2CH3 CI P35-1 18 CH2F CN
P35-89 CH2CH3 Br P35-1 19 CH2F S-CH3
P35-90 CH2CH3 CH3 P35-120 CHF2 H
P35-91 CH2CH3 CH2CH3 P35-121 CHF2 F
P35-92 CH2CH3 CH2F P35-122 CHF2 CI
P35-93 CH2CH3 CHF2 P35-123 CHF2 Br
P35-94 CH2CH3 CF3 P35-124 CHF2 CH3
P35-95 CH2CH3 OCH3 P35-125 CHF2 CH2CH3
P35-96 CH2CH3 OCH2F P35-126 CHF2 CH2F
P35-97 CH2CH3 OCHF2 P35-127 CHF2 CHF2
P35-98 CH2CH3 OCF3 P35-128 CHF2 CF3
P35-99 CH2CH3 cPr P35-129 CHF2 OCH3
P35-100 CH2CH3 C≡CH P35-130 CHF2 OCH2F
P35-101 CH2CH3 CN P35-131 CHF2 OCHF2
P35-102 CH2CH3 S-CH3 P35-132 CHF2 OCF3
P35-103 CH2F H P35-133 CHF2 cPr
P35-104 CH2F F P35-134 CHF2 C≡CH
P35-105 CH2F CI P35-135 CHF2 CN
P35-106 CH2F Br P35-136 CHF2 S-CH3
P35-107 CH2F CH3 P35-137 CF3 H
P35-108 CH2F CH2CH3 P35-138 CF3 F
P35-109 CH2F CH2F P35-139 CF3 CI
P35-1 10 CH2F CHF2 P35-140 CF3 Br
P35-1 1 1 CH2F CF3 P35-141 CF3 CH3
P35-1 12 CH2F OCH3 P35-142 CF3 CH2CH3
P35-1 13 CH2F OCH2F P35-143 CF3 CH2F
P35-1 14 CH2F OCHF2 P35-144 CF3 CHF2 line R9 R10 line R9 R10
P35-145 CFs CFs P35-175 OCH2F CHs
P35-146 CFs OCHs P35-176 OCH2F CH2CH3
P35-147 CFs OCH2F P35-177 OCH2F CH2F
P35-148 CFs OCHF2 P35-178 OCH2F CHF2
P35-149 CFs OCFs P35-179 OCH2F CFs
P35-150 CFs cPr P35-180 OCH2F OCHs
P35-151 CFs C≡CH P35-181 OCH2F OCH2F
P35-152 CFs CN P35-182 OCH2F OCHF2
P35-153 CFs S-CHs P35-183 OCH2F OCFs
P35-154 OCHs H P35-184 OCH2F cPr
P35-155 OCHs F P35-185 OCH2F C≡CH
P35-156 OCHs CI P35-186 OCH2F CN
P35-157 OCHs Br P35-187 OCH2F S-CHs
P35-158 OCHs CHs P35-188 OCHF2 H
P35-159 OCHs CH2CH3 P35-189 OCHF2 F
P35-160 OCHs CH2F P35-190 OCHF2 CI
P35-161 OCHs CHF2 P35-191 OCHF2 Br
P35-162 OCHs CFs P35-192 OCHF2 CHs
P35-163 OCHs OCHs P35-193 OCHF2 CH2CH3
P35-164 OCHs OCH2F P35-194 OCHF2 CH2F
P35-165 OCHs OCHF2 P35-195 OCHF2 CHF2
P35-166 OCHs OCFs P35-196 OCHF2 CF3
P35-167 OCHs cPr P35-197 OCHF2 OCHs
P35-168 OCHs C≡CH P35-198 OCHF2 OCH2F
P35-169 OCHs CN P35-199 OCHF2 OCHF2
P35-170 OCHs S-CHs P35-200 OCHF2 OCFs
P35-171 OCH2F H P35-201 OCHF2 cPr
P35-172 OCH2F F P35-202 OCHF2 C≡CH
P35-173 OCH2F CI P35-203 OCHF2 CN
P35-174 OCH2F Br P35-204 OCHF2 S-CHs line R9 R10 line R9 R10
P35-205 OCFs H P35-235 cPr cPr
P35-206 OCFs F P35-236 cPr C≡CH
P35-207 OCFs CI P35-237 cPr CN
P35-208 OCFs Br P35-238 cPr S-CHs
P35-209 OCFs CHs P35-239 C≡CH H
P35-210 OCFs CH2CH3 P35-240 C≡CH F
P35-21 1 OCFs CH2F P35-241 C≡CH CI
P35-212 OCFs CHF2 P35-242 C≡CH Br
P35-213 OCFs CFs P35-243 C≡CH CHs
P35-214 OCFs OCHs P35-244 C≡CH CH2CH3
P35-215 OCFs OCH2F P35-245 C≡CH CH2F
P35-216 OCFs OCHF2 P35-246 C≡CH CHF2
P35-217 OCFs OCFs P35-247 C≡CH CFs
P35-218 OCFs cPr P35-248 C≡CH OCHs
P35-219 OCFs C≡CH P35-249 C≡CH OCH2F
P35-220 OCFs CN P35-250 C≡CH OCH F2
P35-221 OCFs S-CHs P35-251 C≡CH OCFs
P35-222 cPr H P35-252 C≡CH cPr
P35-223 cPr F P35-253 C≡CH C≡CH
P35-224 cPr CI P35-254 C≡CH CN
P35-225 cPr Br P35-255 C≡CH S-CHs
P35-226 cPr CHs P35-256 CN H
P35-227 cPr CH2CH3 P35-257 CN F
P35-228 cPr CH2F P35-258 CN CI
P35-229 cPr CHF2 P35-259 CN Br
P35-230 cPr CFs P35-260 CN CHs
P35-231 cPr OCHs P35-261 CN CH2CH3
P35-232 cPr OCH2F P35-262 CN CH2F
P35-233 cPr OCHF2 P35-263 CN CHF2
P35-234 cPr OCFs P35-264 CN CFs
Figure imgf000088_0001
Figure imgf000089_0001
Particular embodiments of the compounds I are the following compounds: 1-1.A, 1-1 .B, 1-1.C, I- 1.D, 1-1 . E, 1-1. F, 1-1 .G, 1-1.1; I-2.A, 1-2. B, I-2.C, 1-2. D, I-2.E, 1-2. F, I-2.G, 1-2.1; I-3.A, I-3.B, I-3.C, I- 3.D, 1-3. E, I-3.F, I-3.G, 1-3.1; I-4.A, 1-4. B, I-4.C, 1-4. D, I-4.E, 1-4. F, I-4.G, 1-4.1. In these formulae, the substituents R4, R9 and R10 are independently as defined in claim 1 or preferably defined bel
Figure imgf000089_0002
1-1.1
1-1. G 1-1. H
Figure imgf000090_0001
-2. G 1-2. H
Figure imgf000091_0001
-3. G 1-3. H
Figure imgf000092_0001
Figure imgf000092_0002
Figure imgf000092_0003
I-4.G I-4.H
Particular embodiments of the compounds I are the following compounds: 1-1.A, 1-1. B, 1-1. C, I- 1.D, 1-1 . E, 1-1 . F, 1-1. G, 1-1.1; I-2.A, I-2.B, I-2.C, I-2.D, I-2.E, I-2.F, I-2.G, 1-2.1; I-3.A, I-3.B, I-3.C, I- 3.D, I-3.E, I-3.F, I-3.G, 1-3.1; I-4.A, I-4.B, I-4.C, I-4.D, I-4.E, I-4.F, I-4.G, 1-4.1. that are compiled in the Tables 1-1 to 1 -8, Tables 2-1 to 2-8, Tables 3-1 to 3-8, Tables 4-1 to 4-8, Tables 5-1 to 5-8, Tables 6-1 to 6-8, Tables 7-1 to 7-8, Tables 8-1 to 8-8, Tables 9-1 to 9-8. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
Table 1-1 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -1.A-1 to 1-1 .A.1 -1.A-287, compounds I-2.A.1-
1. A-1 to I-2.A.1 -1.A-287, compounds I-3.A.1-1.A-1 to I-3.A.1 -1 .A-287 compounds I-4.A.1-1.A-1 to I-4.A.1-1. A-287).
Table 1-2 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -2.A-1 to 1-1 .A.1 -2.A-287, compounds I-2.A.1-
2. A-1 to I-2.A.1 -2.A-287, compounds I-3.A.1-2.A-1 to I-3.A.1 -2.A-287 compounds I-4.A.1-2.A-1 to I-4.A.1-2.A-287). Table 1-3 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -3.A-1 to 1-1 .A.1 -3.A-287, compounds I-2.A.1- 3.A-1 to I-2.A.1 -3.A-287, compounds I-3.A.1-3.A-1 to I-3.A.1 -3.A-287 compounds I-4.A.1-3.A-1 to I-4.A.1-3.A-287).
Table 1-4 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1 -4.A-1 to 1-1 .A.1-4.A-287, compounds I-2.A.1 -4.A-1 to I- 2.A.1-4.A-287, compounds I-3.A.1-4.A-1 to I-3.A.1 -4.A-287 compounds I-4.A.1-4.A-1 to I-4.A.1 - 4.A-287).
Table 1-5 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -5.A-1 to 1-1 .A.1 -5.A-287, compounds I-2.A.1- 5.A-1 to I-2.A.1 -5.A-287, compounds I-3.A.1-5.A-1 to I-3.A.1 -5.A-287 compounds I-4.A.1-5.A-1 to I-4.A.1-5.A-287).
Table 1-6 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1-6.A-1 to I-1.A.1 -6.A-287, compounds I- 2.A.1-6.A-1 to I-2.A.1-6.A-287, compounds I-3.A.1-6.A-1 to I-3.A.1-6.A-287 compounds I-4.A.1- 6.A-1 to I-4.A.1 -6.A-287).
Table 1-7 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1 -7.A-1 to 1-1 .A.1-7.A-287, compounds I-2.A.1 -7.A-1 to I- 2.A.1-7.A-287, compounds I-3.A.1-7.A-1 to I-3.A.1 -7.A-287 compounds I-4.A.1-7.A-1 to I-4.A.1 - 7.A-287).
Table 1-8 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -8.A-1 to 1-1 .A.1 -8.A-287, compounds I-2.A.1- 8.A-1 to I-2.A.1 -8.A-287, compounds I-3.A.1-8.A-1 to I-3.A.1 -8.A-287 compounds I-4.A.1-8.A-1 to I-4.A.1-8.A-287).
Table 2-1 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-1.A-1 to 1-1 .B.2-1.A-287, compounds I-2.B.2- 1.A-1 to I-2.B.2-1.A-287, compounds I-3. B.2-1.A-1 to I-3.B.2-1 .A-287 compounds I-4. B.2-1.A-1 to I-4. B.2-1. A-287).
Table 2-2 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-2.A-1 to 1-1 .B.2-2.A-287, compounds I-2.B.2- 2.A-1 to I-2.B.2-2.A-287, compounds I-3.B.2-2.A-1 to I-3.B.2-2.A-287 compounds I-4.B.2-2.A-1 to I-4.B.2-2.A-287). Table 2-3 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-3.A-1 to 1-1 .B.2-3.A-287, compounds I-2.B.2- 3.A-1 to I-2.B.2-3.A-287, compounds I-3.B.2-3.A-1 to I-3.B.2-3.A-287 compounds I-4.B.2-3.A-1 to I-4.B.2-3.A-287).
Table 2-4 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-4.A-1 to 1-1 .B.2-4.A-287, compounds I-2.B.2-4.A-1 to I- 2.B.2-4.A-287, compounds I-3.B.2-4.A-1 to I-3.B.2-4.A-287 compounds I-4.B.2-4.A-1 to I-4.B.2- 4.A-287).
Table 2-5 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-5.A-1 to 1-1 .B.2-5.A-287, compounds I-2.B.2- 5.A-1 to I-2.B.2-5.A-287, compounds I-3.B.2-5.A-1 to I-3.B.2-5.A-287 compounds I-4.B.2-5.A-1 to I-4.B.2-5.A-287).
Table 2-6 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-6.A-1 to 1-1.B.2-6.A-287, compounds I- 2.B.2-6.A-1 to I-2.B.2-6.A-287, compounds I-3.B.2-6.A-1 to I-3.B.2-6.A-287 compounds I-4.B.2- 6.A-1 to I-4.B.2-6.A-287).
Table 2-7 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-7.A-1 to I-1 .B.2-7.A-287, compounds I-2.B.2-7.A-1 to I- 2.B.2-7.A-287, compounds I-3.B.2-7.A-1 to I-3.B.2-7.A-287 compounds I-4.B.2-7.A-1 to I-4.B.2- 7.A-287).
Table 2-8 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-8.A-1 to 1-1 .B.2-8.A-287, compounds I-2.B.2- 8.A-1 to I-2.B.2-8.A-287, compounds I-3.B.2-8.A-1 to I-3.B.2-8.A-287 compounds I-4.B.2-8.A-1 to I-4.B.2-8.A-287).
Table 3-1 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-1 .A-1 to 1-1.C.3-1.A-287, compounds I-2.C.3-
1. A-1 to I-2.C.3-1. A-287, compounds I-3.C.3-1.A-1 to I-3.C.3-1.A-287 compounds I-4.C.3-1.A-1 to I-4. C.3-1 .A-287).
Table 3-2 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-2.A-1 to 1-1.C.3-2.A-287, compounds I-2.C.3-
2. A-1 to I-2.C.3-2.A-287, compounds I-3.C.3-2.A-1 to I-3.C.3-2.A-287 compounds I-4.C.3-2.A-1 to I-4.C.3-2.A-287).
Table 3-3 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-3.A-1 to 1-1.C.3-3.A-287, compounds I-2.C.3- 3.A-1 to I-2.C.3-3.A-287, compounds I-3.C.3-3.A-1 to I-3.C.3-3.A-287 compounds I-4.C.3-3.A-1 to I-4.C.3-3.A-287).
Table 3-4 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-4.A-1 to I-1.C.3-4.A-287, compounds I-2.C.3-4.A-1 to I- 2.C.3-4.A-287, compounds I-3.C.3-4.A-1 to I-3.C.3-4.A-287 compounds I-4.C.3-4.A-1 to I-4.C.3- 4.A-287).
Table 3-5 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-5.A-1 to 1-1.C.3-5.A-287, compounds I-2.C.3- 5.A-1 to I-2.C.3-5.A-287, compounds I-3.C.3-5.A-1 to I-3.C.3-5.A-287 compounds I-4.C.3-5.A-1 to I-4.C.3-5.A-287).
Table 3-6 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-6.A-1 to 1-1.C.3-6.A-287, compounds I- 2.C.3-6.A-1 to I-2.C.3-6.A-287, compounds I-3.C.3-6.A-1 to I-3.C.3-6.A-287 compounds I-4.C.3-
6. A-1 to I-4.C.3-6.A-287).
Table 3-7 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-7.A-1 to I-1.C.3-7.A-287, compounds I-2.C.3-7.A-1 to I- 2.C.3-7.A-287, compounds I-3.C.3-7.A-1 to I-3.C.3-7.A-287 compounds I-4.C.3-7.A-1 to I-4.C.3-
7. A-287).
Table 3-8 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-8.A-1 to 1-1.C.3-8.A-287, compounds I-2.C.3- 8.A-1 to I-2.C.3-8.A-287, compounds I-3.C.3-8.A-1 to I-3.C.3-8.A-287 compounds I-4.C.3-8.A-1 to I-4.C.3-8.A-287).
Table 4-1 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-1 .A-1 to 1-1.D.4-1.A-287, compounds I-2.D.4-
1. A-1 to I-2.D.4-1. A-287, compounds I-3.D.4-1.A-1 to I-3.D.4-1.A-287 compounds I-4.D.4-1.A-1 to I-4. D.4-1 .A-287).
Table 4-2 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-2.A-1 to 1-1.D.4-2.A-287, compounds I-2.D.4-
2. A-1 to I-2.D.4-2.A-287, compounds I-3.D.4-2.A-1 to I-3.D.4-2.A-287 compounds I-4.D.4-2.A-1 to I-4.D.4-2.A-287).
Table 4-3 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-3.A-1 to 1-1.D.4-3.A-287, compounds I-2.D.4- 3.A-1 to I-2.D.4-3.A-287, compounds I-3.D.4-3.A-1 to I-3.D.4-3.A-287 compounds I-4.D.4-3.A-1 to I-4.D.4-3.A-287).
Table 4-4 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-4.A-1 to I-1.D.4-4.A-287, compounds I-2.D.4-4.A-1 to I- 2.D.4-4.A-287, compounds I-3.D.4-4.A-1 to I-3.D.4-4.A-287 compounds I-4.D.4-4.A-1 to I-4.D.4- 4.A-287).
Table 4-5 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-5.A-1 to 1-1.D.4-5.A-287, compounds I-2.D.4- 5.A-1 to I-2.D.4-5.A-287, compounds I-3.D.4-5.A-1 to I-3.D.4-5.A-287 compounds I-4.D.4-5.A-1 to I-4.D.4-5.A-287).
Table 4-6 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-6.A-1 to 1-1.D.4-6.A-287, compounds I- 2.D.4-6.A-1 to I-2.D.4-6.A-287, compounds I-3.D.4-6.A-1 to I-3.D.4-6.A-287 compounds I-4.D.4-
6. A-1 to I-4.D.4-6.A-287).
Table 4-7 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-7.A-1 to I-1.D.4-7.A-287, compounds I-2.D.4-7.A-1 to I- 2.D.4-7.A-287, compounds I-3.D.4-7.A-1 to I-3.D.4-7.A-287 compounds I-4.D.4-7.A-1 to I-4.D.4-
7. A-287).
Table 4-8 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-8.A-1 to 1-1.D.4-8.A-287, compounds I-2.D.4- 8.A-1 to I-2.D.4-8.A-287, compounds I-3.D.4-8.A-1 to I-3.D.4-8.A-287 compounds I-4.D.4-8.A-1 to I-4.D.4-8.A-287).
Table 5-1 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-1.A-1 to 1-1 .E.5-1.A-287, compounds I-2.E.5-
1. A-1 to I-2.E.5-1.A-287, compounds I-3. E.5-1. A-1 to I-3.E.5-1 .A-287 compounds I-4. E.5-1. A-1 to I-4. E.5-1. A-287).
Table 5-2 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-2.A-1 to 1-1 .E.5-2.A-287, compounds I-2.E.5-
2. A-1 to I-2.E.5-2.A-287, compounds I-3.E.5-2.A-1 to I-3.E.5-2.A-287 compounds I-4.E.5-2.A-1 to I-4.E.5-2.A-287).
Table 5-3 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-3.A-1 to 1-1 .E.5-3.A-287, compounds I-2.E.5- 3.A-1 to I-2.E.5-3.A-287, compounds I-3.E.5-3.A-1 to I-3.E.5-3.A-287 compounds I-4.E.5-3.A-1 to I-4.E.5-3.A-287).
Table 5-4 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-4.A-1 to 1-1 .E.5-4.A-287, compounds I-2.E.5-4.A-1 to I- 2.E.5-4.A-287, compounds I-3.E.5-4.A-1 to I-3.E.5-4.A-287 compounds I-4.E.5-4.A-1 to I-4.E.5- 4.A-287).
Table 5-5 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-5.A-1 to 1-1 .E.5-5.A-287, compounds I-2.E.5- 5.A-1 to I-2.E.5-5.A-287, compounds I-3.E.5-5.A-1 to I-3.E.5-5.A-287 compounds I-4.E.5-5.A-1 to I-4.E.5-5.A-287).
Table 5-6 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-6.A-1 to 1-1.E.5-6.A-287, compounds I- 2.E.5-6.A-1 to I-2.E.5-6.A-287, compounds I-3.E.5-6.A-1 to I-3.E.5-6.A-287 compounds I-4.E.5-
6. A-1 to I-4.E.5-6.A-287).
Table 5-7 Compounds of the formula 1-1. E, I-2.E, I-3.E, I-4.E in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-7.A-1 to 1-1 .E.5-7.A-287, compounds I-2.E.5-7.A-1 to I- 2.E.5-7.A-287, compounds I-3.E.5-7.A-1 to I-3.E.5-7.A-287 compounds I-4.E.5-7.A-1 to I-4.E.5-
7. A-287).
Table 5-8 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-8.A-1 to 1-1 .E.5-8.A-287, compounds I-2.E.5- 8.A-1 to I-2.E.5-8.A-287, compounds I-3.E.5-8.A-1 to I-3.E.5-8.A-287 compounds I-4.E.5-8.A-1 to I-4.E.5-8.A-287).
Table 6-1 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1 .F.1-1.A-1 to I-1.F.1-1.A-287, compounds I-2.F.1-1 .A-1 to I- 2.F.1 -1 .A-287, compounds I-3.F.1-1.A-1 to I-3.F.1-1 .A-287 compounds I-4.F.1 -1 .A-1 to I-4.F.1 - 1.A-287).
Table 6-2 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-2.A-1 to 1-1 .F.1 -2.A-287, compounds I-2.F.1 - 2.A-1 to I-2.F.1-2.A-287, compounds I-3.F.1 -2.A-1 to I-3.F.1 -2.A-287 compounds I-4.F.1-2.A-1 to I-4.F.1 -2.A-287). Table 6-3 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-3.A-1 to 1-1 .F.1 -3.A-287, compounds I-2.F.1 - 3.A-1 to I-2.F.1-3.A-287, compounds I-3.F.1 -3.A-1 to I-3.F.1 -3.A-287 compounds I-4.F.1-3.A-1 to I-4.F.1 -3.A-287).
Table 6-4 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .F.1-4.A-1 to I-1.F.1-4.A-287, compounds I-2.F.1-4.A-1 to I- 2.F.1 -4.A-287, compounds I-3.F.1-4.A-1 to I-3.F.1-4.A-287 compounds I-4.F.1 -4.A-1 to I-4.F.1 - 4.A-287).
Table 6-5 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-5.A-1 to 1-1 .F.1 -5.A-287, compounds I-2.F.1 - 5.A-1 to I-2.F.1-5.A-287, compounds I-3.F.1 -5.A-1 to I-3.F.1 -5.A-287 compounds I-4.F.1-5.A-1 to I-4.F.1 -5.A-287).
Table 6-6 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.F.1-6.A-1 to 1-1.F.1-6.A-287, compounds I- 2.F.1 -6.A-1 to I-2.F.1 -6.A-287, compounds I-3.F.1-6.A-1 to I-3.F.1-6.A-287 compounds I-4.F.1 - 6.A-1 to I-4.F.1-6.A-287).
Table 6-7 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-7.A-1 to I-1.F.1-7.A-287, compounds I-2.F.1 -7.A-1 to I-2.F.1 - 7.A-287, compounds I-3.F.1 -7.A-1 to I-3.F.1 -7.A-287 compounds I-4.F.1-7.A-1 to I-4.F.1-7.A- 287).
Table 6-8 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .F.1-8.A-1 to I-1.F.1-8.A-287, compounds I-2.F.1-8.A-1 to I- 2.F.1 -8.A-287, compounds I-3.F.1-8.A-1 to I-3.F.1-8.A-287 compounds I-4.F.1 -8.A-1 to I-4.F.1 - 8.A-287).
Table 7-1 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-1.A-1 to 1-1 .G.7-1.A-287, compounds I-2.G.7-
1. A-1 to I-2.G.7-1.A-287, compounds I-3.G.7-1.A-1 to I-3.G.7-1 .A-287 compounds I-4.G.7-1.A-1 to I-4. G.7-1.A-287).
Table 7-2 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-2.A-1 to 1-1 .G.7-2.A-287, compounds I-2.G.7-
2. A-1 to I-2.G.7-2.A-287, compounds I-3.G.7-2.A-1 to I-3.G.7-2.A-287 compounds I-4.G.7-2.A-1 to I-4.G.7-2.A-287).
Table 7-3 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-3.A-1 to 1-1 .G.7-3.A-287, compounds I-2.G.7-
3. A-1 to I-2.G.7-3.A-287, compounds I-3.G.7-3.A-1 to I-3.G.7-3.A-287 compounds I-4.G.7-3.A-1 to I-4.G.7-3.A-287).
Table 7-4 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .G.7-4.A-1 to I-1.G.7-4.A-287, compounds I-2.G.7-4.A-1 to I- 2.G.7-4.A-287, compounds I-3.G.7-4.A-1 to I-3.G.7-4.A-287 compounds I-4.G.7-4.A-1 to I-
4. G.7-4.A-287).
Table 7-5 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-5.A-1 to 1-1 .G.7-5.A-287, compounds I-2.G.7-
5. A-1 to I-2.G.7-5.A-287, compounds I-3.G.7-5.A-1 to I-3.G.7-5.A-287 compounds I-4.G.7-5.A-1 to I-4.G.7-5.A-287).
Table 7-6 Compounds of the formula 1-1. G, I-2.G, I-3.G, I-4.G in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .G.7-6.A-1 to 1-1.G.7-6.A-287, compounds I- 2.G.7-6.A-1 to I-2.G.7-6.A-287, compounds I-3.G.7-6.A-1 to I-3.G.7-6.A-287 compounds I- 4.G.7-6.A-1 to I-4.G.7-6.A-287).
Table 7-7 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .G.7-7.A-1 to I-1.G.7-7.A-287, compounds I-2.G.7-7.A-1 to I- 2.G.7-7.A-287, compounds I-3.G.7-7.A-1 to I-3.G.7-7.A-287 compounds I-4.G.7-7.A-1 to I- 4.G.7-7.A-287).
Table 7-8 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-8.A-1 to 1-1 .G.7-8.A-287, compounds I-2.G.7- 8.A-1 to I-2.G.7-8.A-287, compounds I-3.G.7-8.A-1 to I-3.G.7-8.A-287 compounds I-4.G.7-8.A-1 to I-4.G.7-8.A-287).
Table 8-1 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.H.8-1 .A-1 to 1-1.H.8-1.A-287, compounds I-2.H.8-
1. A-1 to I-2.H.8-1. A-287, compounds I-3.H.8-1.A-1 to I-3.H.8-1.A-287 compounds I-4.H.8-1.A-1 to I-4.H.8-1 .A-287).
Table 8-2 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.H.8-2.A-1 to 1-1.H.8-2.A-287, compounds I-2.H.8-
2. A-1 to I-2.H.8-2.A-287, compounds I-3.H.8-2.A-1 to I-3.H.8-2.A-287 compounds I-4.H.8-2.A-1 to I-4.H.8-2.A-287).
Table 8-3 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-3.A-1 to 1-1.H.8-3.A-287, compounds I-2.H.8-
3. A-1 to I-2.H.8-3.A-287, compounds I-3.H.8-3.A-1 to I-3.H.8-3.A-287 compounds I-4.H.8-3.A-1 to I-4.H.8-3.A-287).
Table 8-4 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is Br and the mean- ing for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-4.A-1 to I-1.H.8-4.A-287, compounds I-2.H.8-4.A-1 to I- 2.H.8-4.A-287, compounds I-3.H.8-4.A-1 to I-3.H.8-4.A-287 compounds I-4.H.8-4.A-1 to I-4.H.8-
4. A-287).
Table 8-5 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-5.A-1 to 1-1.H.8-5.A-287, compounds I-2.H.8-
5. A-1 to I-2.H.8-5.A-287, compounds I-3.H.8-5.A-1 to I-3.H.8-5.A-287 compounds I-4.H.8-5.A-1 to I-4.H.8-5.A-287).
Table 8-6 Compounds of the formula 1-1. H, I-2.H, I-3.H, I-4.H in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-6.A-1 to 1-1.H.8-6.A-287, compounds I- 2.H.8-6.A-1 to I-2.H.8-6.A-287, compounds I-3.H.8-6.A-1 to I-3.H.8-6.A-287 compounds I-4.H.8-
6. A-1 to I-4.H.8-6.A-287).
Table 8-7 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is H and the mean- ing for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-7.A-1 to I-1.H.8-7.A-287, compounds I-2.H.8-7.A-1 to I- 2.H.8-7.A-287, compounds I-3.H.8-7.A-1 to I-3.H.8-7.A-287 compounds I-4.H.8-7.A-1 to I-4.H.8-
7. A-287).
Table 8-8 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-8.A-1 to 1-1.H.8-8.A-287, compounds I-2.H.8-
8. A-1 to I-2.H.8-8.A-287, compounds I-3.H.8-8.A-1 to I-3.H.8-8.A-287 compounds I-4.H.8-8.A-1 to I-4.H.8-8.A-287).
Table 9-1 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.1.9-1 .A-1 to 1-1.1.9-1 .A-287, compounds 1-2.1.9-1 .A-1 to I-2.I.9- 1.A-287, compounds 1-3.1.9-1. A-1 to 1-3.1.9-1 .A-287 compounds 1-4.1.9-1.A-1 to 1-4.1.9-1 .A-287).
Table 9-2 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .1.9-2.A-1 to 1-1.1.9-2.A-287, compounds I-2.I.9-2.A-1 to I- 2.I.9-2.A-287, compounds I-3.I.9-2.A-1 to I -3.1.9-2. A-287 compounds I-4.I.9-2.A-1 to I-4.I.9-2.A- 287).
Table 9-3 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .1.9-3.A-1 to 1-1.1.9-3.A-287, compounds I-2.I.9-3.A-1 to I- 2.I.9-3.A-287, compounds I-3.I.9-3.A-1 to I-3.I.9-3.A-287 compounds I-4.I.9-3.A-1 to I-4.I.9-3.A- 287).
Table 9-4 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.I.9-4.A-1 to I-1.I.9-4.A-287, compounds I-2.I.9-4.A-1 to I-2.I.9- 4.A-287, compounds I-3.I.9-4.A-1 to I-3.I.9-4.A-287 compounds I-4.I.9-4.A-1 to I-4.I.9-4.A-287).
Table 9-5 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .1.9-5.A-1 to I-1.I.9-5.A-287, compounds I-2.I.9-5.A-1 to I- 2.I.9-5.A-287, compounds I-3.I.9-5.A-1 to I-3.I.9-5.A-287 compounds I-4.I.9-5.A-1 to I-4.I.9-5.A- 287).
Table 9-6 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.1.9-6.A-1 to 1-1 .1.9-6.A-287, compounds I-2.I.9-6.A-1 to I-2.I.9-6.A-287, compounds I-3.I.9-6.A-1 to I-3.I.9-6.A-287 compounds I-4.I.9-6.A-1 to I-4.I.9- 6.A-287).
Table 9-7 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is H and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.I.9-7.A-1 to I-1.I.9-7.A-287, compounds I-2.I.9-7.A-1 to I-2.I.9-
7. A-287, compounds I-3.I.9-7.A-1 to I-3.I.9-7.A-287 compounds I-4.I.9-7.A-1 to I-4.I.9-7.A-287). Table 9-8 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1.I.9-8.A-1 to I-1.I.9-8.A-287, compounds I-2.I.9-8.A-1 to I-2.I.9-
8. A-287, compounds I-3.I.9-8.A-1 to I-3.I.9-8.A-287 compounds I-4.I.9-8.A-1 to I-4.I.9-8.A-287). Particular embodiments of the compounds I are the following compounds: X-1.A, X-1.B, X-1 .C, X-1 .D, X-1.E, X-1 .F, X-1.G, X-1.1; X-2.A, X-2.B, X-2.C, X-2.D, X-2.E, X-2.F, X-2.G, X-2.I; X-3.A, X-3.B, X-3.C, X-3.D, X-3.E, X-3.F, X-3.G, X-3.I; X-4.A, X-4.B, X-4.C, X-4.D, X-4.E, X-4.F, X-4.G, X-4.I. In these formulae, the substituents R3, R4, R9 and R10 are independently as defined in claim 1 or preferably defined below:
Figure imgf000102_0001
X-1.G X-1.H
Figure imgf000103_0001
X-2.G X-2.H
Figure imgf000104_0001
X-3.1
X-3.G X-3.
Figure imgf000105_0001
Figure imgf000105_0002
Figure imgf000105_0003
X-4.G X-4.H
Particular embodiments of the compounds I are the following compounds: X-1 .A, X-1 .B, X-1.C, X-1 .D, X-1.E, X-1.F, X-1.G, X-1.1; X-2.A, X-2.B, X-2.C, X-2.D, X-2.E, X-2.F, X-2.G, X-2.1; X-3.A, X-3.B, X-3.C, X-3.D, X-3.E, X-3.F, X-3.G, X-3.1; X-4.A, X-4.B, X-4.C, X-4.D, X-4.E, X-4.F, X-4.G, X-4.1. that are compiled in the Tables 1 -1 to 1-8, Tables 2-1 to 2-8, Tables 3-1 to 3-8, Tables 4-1 to 4-8, Tables 5-1 to 5-8, Tables 6-1 to 6-8, Tables 7-1 to 7-8, Tables 8-1 to 8-8, Tables 9-1 to 9- 8. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
Table 1-1 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-1.A-1 to X-1.A.1 -1 .A-287, compounds X-2.A.1 -
1. A-1 to X-2.A.1 -1.A-287, compounds X-3.A.1-1 .A-1 to X-3. A.1-1. A-287 compounds X-4.A.1- 1.A-1 to X-4. A.1-1. A-287).
Table 1-2 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-2.A-1 to X-1.A.1 -2.A-287, compounds X-2.A.1 -
2. A-1 to X-2.A.1 -2.A-287, compounds X-3.A.1-2.A-1 to X-3.A.1-2.A-287 compounds X-4.A.1- 2.A-1 to X-4.A.1-2.A-287). Table 1-3 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-3.A-1 to X-1.A.1-3.A-287, compounds X-2.A.1-
3. A-1 to X-2.A.1-3.A-287, compounds X-3.A.1-3.A-1 to X-3.A.1-3.A-287 compounds X-4.A.1- 3.A-1 to X-4.A.1-3.A-287).
Table 1-4 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-4.A-1 to X-1.A.1 -4.A-287, compounds X-2.A.1-
4. A-1 to X-2.A.1-4.A-287, compounds X-3.A.1-4.A-1 to X-3.A.1-4.A-287 compounds X-4.A.1- 4.A-1 to X-4.A.1-4.A-287).
Table 1-5 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-5.A-1 to X-1.A.1-5.A-287, compounds X-2.A.1-
5. A-1 to X-2.A.1-5.A-287, compounds X-3.A.1-5.A-1 to X-3.A.1-5.A-287 compounds X-4.A.1- 5.A-1 to X-4.A.1-5.A-287).
Table 1-6 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R9 is cyclopropyl and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-6.A-1 to X-1.A.1-6.A-287, compounds X- 2.A.1-6.A-1 to X-2.A.1-6.A-287, compounds X-3.A.1-6.A-1 to X-3.A.1-6.A-287 compounds X- 4.A.1-6.A-1 to X-4.A.1-6.A-287).
Table 1-7 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-7.A-1 to X-1.A.1 -7.A-287, compounds X-2.A.1-
7. A-1 to X-2.A.1-7.A-287, compounds X-3.A.1-7.A-1 to X-3.A.1-7.A-287 compounds X-4.A.1- 7.A-1 to X-4.A.1-7.A-287).
Table 1-8 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-8.A-1 to X-1.A.1-8.A-287, compounds X-2.A.1-
8. A-1 to X-2.A.1-8.A-287, compounds X-3.A.1-8.A-1 to X-3.A.1-8.A-287 compounds X-4.A.1- 8.A-1 to X-4.A.1-8.A-287).
Table 2-1 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-1.A-1 to X-1.B.2-1.A-287, compounds X-2.B.2- 1.A-1 to X-2.B.2-1.A-287, compounds X-3. B.2-1.A-1 to X-3. B.2-1.A-287 compounds X-4.B.2-
1. A-1 to X-4. B.2-1. A-287).
Table 2-2 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-2.A-1 to X-1.B.2-2.A-287, compounds X-2.B.2- 2.A-1 to X-2.B.2-2.A-287, compounds X-3.B.2-2.A-1 to X-3.B.2-2.A-287 compounds X-4.B.2-
2. A-1 to X-4.B.2-2.A-287). Table 2-3 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-3.A-1 to X-1.B.2-3.A-287, compounds X-2.B.2-
3. A-1 to X-2.B.2-3.A-287, compounds X-3.B.2-3.A-1 to X-3.B.2-3.A-287 compounds X-4.B.2- 3.A-1 to X-4.B.2-3.A-287).
Table 2-4 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-4.A-1 to X-1.B.2-4.A-287, compounds X-2.B.2-
4. A-1 to X-2.B.2-4.A-287, compounds X-3.B.2-4.A-1 to X-3.B.2-4.A-287 compounds X-4.B.2- 4.A-1 to X-4.B.2-4.A-287).
Table 2-5 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-5.A-1 to X-1.B.2-5.A-287, compounds X-2.B.2-
5. A-1 to X-2.B.2-5.A-287, compounds X-3.B.2-5.A-1 to X-3.B.2-5.A-287 compounds X-4.B.2- 5.A-1 to X-4.B.2-5.A-287).
Table 2-6 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R9 is cyclopropyl and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-6.A-1 to X-1.B.2-6. A-287, compounds X- 2.B.2-6.A-1 to X-2.B.2-6.A-287, compounds X-3.B.2-6.A-1 to X-3.B.2-6.A-287 compounds X- 4.B.2-6.A-1 to X-4.B.2-6.A-287).
Table 2-7 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-7.A-1 to X-1.B.2-7.A-287, compounds X-2.B.2-
7. A-1 to X-2.B.2-7.A-287, compounds X-3.B.2-7.A-1 to X-3.B.2-7.A-287 compounds X-4.B.2- 7.A-1 to X-4.B.2-7.A-287).
Table 2-8 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-8.A-1 to X-1.B.2-8.A-287, compounds X-2.B.2-
8. A-1 to X-2.B.2-8.A-287, compounds X-3.B.2-8.A-1 to X-3.B.2-8.A-287 compounds X-4.B.2- 8.A-1 to X-4.B.2-8.A-287).
Table 3-1 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-1.A-1 to X-1.C.3-1.A-287, compounds X-2.C.3- 1.A-1 to X-2. C.3-1.A-287, compounds X-3. C.3-1.A-1 to X-3.C.3-1.A-287 compounds X-4.C.3-
1. A-1 to X-4. C.3-1.A-287).
Table 3-2 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-2.A-1 to X-1.C.3-2.A-287, compounds X-2.C.3-
2. A-1 to X-2.C.3-2.A-287, compounds X-3.C.3-2.A-1 to X-3.C.3-2.A-287 compounds X-4.C.3- 2. A-1 to X-4.C.3-2.A-287).
Table 3-3 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-3.A-1 to X-1.C.3-3.A-287, compounds X-2.C.3- 3.A-1 to X-2.C.3-3.A-287, compounds X-3.C.3-3.A-1 to X-3.C.3-3.A-287 compounds X-4.C.3-
3. A-1 to X-4.C.3-3.A-287).
Table 3-4 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-4.A-1 to X-1.C.3-4.A-287, compounds X-2.C.3- 4.A-1 to X-2.C.3-4.A-287, compounds X-3.C.3-4.A-1 to X-3.C.3-4.A-287 compounds X-4.C.3-
4. A-1 to X-4.C.3-4.A-287).
Table 3-5 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-5.A-1 to X-1.C.3-5.A-287, compounds X-2.C.3- 5.A-1 to X-2.C.3-5.A-287, compounds X-3.C.3-5.A-1 to X-3.C.3-5.A-287 compounds X-4.C.3-
5. A-1 to X-4.C.3-5.A-287).
Table 3-6 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is cyclopropyl and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-6.A-1 to X-1.C.3-6.A-287, compounds X- 2.C.3-6.A-1 to X-2.C.3-6.A-287, compounds X-3.C.3-6.A-1 to X-3.C.3-6.A-287 compounds X- 4.C.3-6.A-1 to X-4.C.3-6.A-287).
Table 3-7 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-7.A-1 to X-1.C.3-7.A-287, compounds X-2.C.3- 7.A-1 to X-2.C.3-7.A-287, compounds X-3.C.3-7.A-1 to X-3.C.3-7.A-287 compounds X-4.C.3-
7. A-1 to X-4.C.3-7.A-287).
Table 3-8 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-8.A-1 to X-1.C.3-8.A-287, compounds X-2.C.3- 8.A-1 to X-2.C.3-8.A-287, compounds X-3.C.3-8.A-1 to X-3.C.3-8.A-287 compounds X-4.C.3-
8. A-1 to X-4.C.3-8.A-287).
Table 4-1 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-1.A-1 to X-1.D.4-1.A-287, compounds X-2.D.4- 1.A-1 to X-2. D.4-1.A-287, compounds X-3. D.4-1.A-1 to X-3. D.4-1.A-287 compounds X-4.D.4-
1. A-1 to X-4. D.4-1.A-287).
Table 4-2 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-2.A-1 to X-1.D.4-2.A-287, compounds X-2.D.4-
2. A-1 to X-2.D.4-2.A-287, compounds X-3.D.4-2.A-1 to X-3.D.4-2.A-287 compounds X-4.D.4- 2. A-1 to X-4.D.4-2.A-287).
Table 4-3 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-3.A-1 to X-1.D.4-3.A-287, compounds X-2.D.4- 3.A-1 to X-2.D.4-3.A-287, compounds X-3.D.4-3.A-1 to X-3.D.4-3.A-287 compounds X-4.D.4-
3. A-1 to X-4.D.4-3.A-287).
Table 4-4 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-4.A-1 to X-1.D.4-4.A-287, compounds X-2.D.4- 4.A-1 to X-2.D.4-4.A-287, compounds X-3.D.4-4.A-1 to X-3.D.4-4.A-287 compounds X-4.D.4-
4. A-1 to X-4.D.4-4.A-287).
Table 4-5 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-5.A-1 to X-1.D.4-5.A-287, compounds X-2.D.4- 5.A-1 to X-2.D.4-5.A-287, compounds X-3.D.4-5.A-1 to X-3.D.4-5.A-287 compounds X-4.D.4-
5. A-1 to X-4.D.4-5.A-287).
Table 4-6 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is cyclopropyl and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-6.A-1 to X-1.D.4-6.A-287, compounds X- 2.D.4-6.A-1 to X-2.D.4-6.A-287, compounds X-3.D.4-6.A-1 to X-3.D.4-6.A-287 compounds X- 4.D.4-6.A-1 to X-4.D.4-6.A-287).
Table 4-7 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-7.A-1 to X-1.D.4-7.A-287, compounds X-2.D.4- 7.A-1 to X-2.D.4-7.A-287, compounds X-3.D.4-7.A-1 to X-3.D.4-7.A-287 compounds X-4.D.4-
7. A-1 to X-4.D.4-7.A-287).
Table 4-8 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-8.A-1 to X-1.D.4-8.A-287, compounds X-2.D.4- 8.A-1 to X-2.D.4-8.A-287, compounds X-3.D.4-8.A-1 to X-3.D.4-8.A-287 compounds X-4.D.4-
8. A-1 to X-4.D.4-8.A-287).
Table 5-1 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-1.A-1 to X-1.E.5-1.A-287, compounds X-2.E.5- 1.A-1 to X-2.E.5-1.A-287, compounds X-3.E.5-1.A-1 to X-3. E.5-1. A-287 compounds X-4.E.5-
1. A-1 to X-4. E.5-1. A-287).
Table 5-2 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-2.A-1 to X-1.E.5-2.A-287, compounds X-2.E.5-
2. A-1 to X-2.E.5-2.A-287, compounds X-3.E.5-2.A-1 to X-3.E.5-2.A-287 compounds X-4.E.5- 2. A-1 to X-4.E.5-2.A-287).
Table 5-3 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-3.A-1 to X-1.E.5-3.A-287, compounds X-2.E.5- 3.A-1 to X-2.E.5-3.A-287, compounds X-3.E.5-3.A-1 to X-3.E.5-3.A-287 compounds X-4.E.5-
3. A-1 to X-4.E.5-3.A-287).
Table 5-4 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-4.A-1 to X-1.E.5-4.A-287, compounds X-2.E.5- 4.A-1 to X-2.E.5-4.A-287, compounds X-3.E.5-4.A-1 to X-3.E.5-4.A-287 compounds X-4.E.5-
4. A-1 to X-4.E.5-4.A-287).
Table 5-5 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-5.A-1 to X-1.E.5-5.A-287, compounds X-2.E.5- 5.A-1 to X-2.E.5-5.A-287, compounds X-3.E.5-5.A-1 to X-3.E.5-5.A-287 compounds X-4.E.5-
5. A-1 to X-4.E.5-5.A-287).
Table 5-6 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R9 is cyclopropyl and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-6.A-1 to X-1.E.5-6.A-287, compounds X- 2.E.5-6.A-1 to X-2.E.5-6.A-287, compounds X-3.E.5-6.A-1 to X-3.E.5-6.A-287 compounds X- 4.E.5-6.A-1 to X-4.E.5-6.A-287).
Table 5-7 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-7.A-1 to X-1.E.5-7.A-287, compounds X-2.E.5- 7.A-1 to X-2.E.5-7.A-287, compounds X-3.E.5-7.A-1 to X-3.E.5-7.A-287 compounds X-4.E.5-
7. A-1 to X-4.E.5-7.A-287).
Table 5-8 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-8.A-1 to X-1.E.5-8.A-287, compounds X-2.E.5- 8.A-1 to X-2.E.5-8.A-287, compounds X-3.E.5-8.A-1 to X-3.E.5-8.A-287 compounds X-4.E.5-
8. A-1 to X-4.E.5-8.A-287).
Table 6-1 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-1.A-1 to X-1.F.1-1.A-287, compounds X-2.F.1- 1.A-1 to X-2.F.1-1.A-287, compounds X-3.F.1-1.A-1 to X-3.F.1-1.A-287 compounds X-4.F.1-
1. A-1 to X-4.F.1-1.A-287).
Table 6-2 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-2.A-1 to X-1.F.1-2.A-287, compounds X-2.F.1-
2. A-1 to X-2.F.1-2.A-287, compounds X-3.F.1-2.A-1 to X-3.F.1-2.A-287 compounds X-4.F.1- 2. A-1 to X-4.F.1-2.A-287).
Table 6-3 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-3.A-1 to X-1.F.1-3.A-287, compounds X-2.F.1- 3.A-1 to X-2.F.1-3.A-287, compounds X-3.F.1-3.A-1 to X-3.F.1-3.A-287 compounds X-4.F.1-
3. A-1 to X-4.F.1-3.A-287).
Table 6-4 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-4.A-1 to X-1.F.1-4.A-287, compounds X-2.F.1- 4.A-1 to X-2.F.1-4.A-287, compounds X-3.F.1-4.A-1 to X-3.F.1-4.A-287 compounds X-4.F.1-
4. A-1 to X-4.F.1-4.A-287).
Table 6-5 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-5.A-1 to X-1.F.1-5.A-287, compounds X-2.F.1- 5.A-1 to X-2.F.1-5.A-287, compounds X-3.F.1-5.A-1 to X-3.F.1-5.A-287 compounds X-4.F.1-
5. A-1 to X-4.F.1-5.A-287).
Table 6-6 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is cyclopropyl and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-6.A-1 to X-1.F.1-6.A-287, compounds X- 2.F.1-6.A-1 to X-2.F.1-6.A-287, compounds X-3.F.1-6.A-1 to X-3.F.1-6.A-287 compounds X- 4.F.1-6.A-1 to X-4.F.1-6.A-287).
Table 6-7 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-7.A-1 to X-1.F.1-7.A-287, compounds X-2.F.1- 7.A-1 to X-2.F.1-7.A-287, compounds X-3.F.1-7.A-1 to X-3.F.1-7.A-287 compounds X-4.F.1-
7. A-1 to X-4.F.1-7.A-287).
Table 6-8 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-8.A-1 to X-1.F.1-8.A-287, compounds X-2.F.1- 8.A-1 to X-2.F.1-8.A-287, compounds X-3.F.1-8.A-1 to X-3.F.1-8.A-287 compounds X-4.F.1-
8. A-1 to X-4.F.1-8.A-287).
Table 7-1 Compounds of the formula X-1.G, X-2.G, X-3.G, X-4.G in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.G.7-1.A-1 to X-1.G.7-1.A-287, compounds X- 2.G.7-1.A-1 to X-2.G.7-1.A-287, compounds X-3.G.7-1.A-1 to X-3. G.7-1.A-287 compounds X- 4.G.7-1.A-1 to X-4.G.7-1.A-287).
Table 7-2 Compounds of the formula X-1.G, X-2.G, X-3.G, X-4.G in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.G.7-2.A-1 to X-1.G.7-2.A-287, compounds X- 2.G.7-2.A-1 to X-2.G.7-2.A-287, compounds X-3.G.7-2.A-1 to X-3.G.7-2.A-287 compounds X- 4.G.7-2.A-1 to X-4.G.7-2.A-287). Table 7-3 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.G.7-3.A-1 to X-1 .G.7-3.A-287, compounds X- 2.G.7-3.A-1 to X-2.G.7-3.A-287, compounds X-3.G.7-3.A-1 to X-3.G.7-3.A-287 compounds X- 4.G.7-3.A-1 to X-4.G.7-3.A-287).
Table 7-4 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-4.A-1 to X-1.G.7-4.A-287, compounds X- 2.G.7-4.A-1 to X-2.G.7-4.A-287, compounds X-3.G.7-4.A-1 to X-3.G.7-4.A-287 compounds X- 4.G.7-4.A-1 to X-4.G.7-4.A-287).
Table 7-5 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-5.A-1 to X-1.G.7-5.A-287, compounds X- 2.G.7-5.A-1 to X-2.G.7-5.A-287, compounds X-3.G.7-5.A-1 to X-3.G.7-5.A-287 compounds X- 4.G.7-5.A-1 to X-4.G.7-5.A-287).
Table 7-6 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-6.A-1 to X-1 .G.7-6.A-287, compounds X- 2.G.7-6.A-1 to X-2.G.7-6.A-287, compounds X-3.G.7-6.A-1 to X-3.G.7-6.A-287 compounds X- 4.G.7-6.A-1 to X-4.G.7-6.A-287).
Table 7-7 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-7.A-1 to X-1.G.7-7.A-287, compounds X- 2.G.7-7.A-1 to X-2.G.7-7.A-287, compounds X-3.G.7-7.A-1 to X-3.G.7-7.A-287 compounds X- 4.G.7-7.A-1 to X-4.G.7-7.A-287).
Table 7-8 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-8.A-1 to X-1.G.7-8.A-287, compounds X- 2.G.7-8.A-1 to X-2.G.7-8.A-287, compounds X-3.G.7-8.A-1 to X-3.G.7-8.A-287 compounds X- 4.G.7-8.A-1 to X-4.G.7-8.A-287).
Table 8-1 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-1.A-1 to X-1.H.8-1 .A-287, compounds X-2.H.8- 1.A-1 to X-2. H.8-1 .A-287, compounds X-3. H.8-1 .A-1 to X-3. H.8-1.A-287 compounds X-4.H.8- 1. A-1 to X-4. H.8-1 .A-287).
Table 8-2 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-2.A-1 to X-1.H.8-2.A-287, compounds X-2.H.8- 2.A-1 to X-2.H.8-2.A-287, compounds X-3.H.8-2.A-1 to X-3.H.8-2.A-287 compounds X-4.H.8- 2.A-1 to X-4.H.8-2.A-287).
Table 8-3 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-3.A-1 to X-1.H.8-3.A-287, compounds X-2.H.8- 3.A-1 to X-2.H.8-3.A-287, compounds X-3.H.8-3.A-1 to X-3.H.8-3.A-287 compounds X-4.H.8-
3. A-1 to X-4.H.8-3.A-287).
Table 8-4 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-4.A-1 to X-1.H.8-4.A-287, compounds X-2.H.8-
4. A-1 to X-2. H.8-4.A-287, compounds X-3.H.8-4.A-1 to X-3.H.8-4.A-287 compounds X-4.H.8-
4. A-1 to X-4. H.8-4.A-287).
Table 8-5 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-5.A-1 to X-1.H.8-5.A-287, compounds X-2.H.8-
5. A-1 to X-2.H.8-5.A-287, compounds X-3.H.8-5.A-1 to X-3.H.8-5.A-287 compounds X-4.H.8- 5.A-1 to X-4.H.8-5.A-287).
Table 8-6 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-6.A-1 to X-1.H.8-6.A-287, compounds X- 2.H.8-6.A-1 to X-2.H.8-6.A-287, compounds X-3.H.8-6.A-1 to X-3.H.8-6.A-287 compounds X- 4.H.8-6.A-1 to X-4.H.8-6.A-287).
Table 8-7 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-7.A-1 to X-1.H.8-7.A-287, compounds X-2.H.8- 7.A-1 to X-2. H.8-7.A-287, compounds X-3.H.8-7.A-1 to X-3.H.8-7.A-287 compounds X-4.H.8-
7. A-1 to X-4. H.8-7.A-287).
Table 8-8 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-8.A-1 to X-1.H.8-8.A-287, compounds X-2.H.8-
8. A-1 to X-2.H.8-8.A-287, compounds X-3.H.8-8.A-1 to X-3.H.8-8.A-287 compounds X-4.H.8- 8.A-1 to X-4.H.8-8.A-287).
Table 9-1 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.1 in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-1.A-1 to X-1 .1.9-1.A-287, compounds X-2.1.9-
1. A-1 to X-2.1.9-1.A-287, compounds X-3.1.9-1. A-1 to X-3.1.9-1 .A-287 compounds X-4.1.9-1. A-1 to X-4.1.9-1. A-287).
Table 9-2 Compounds of the formula X-1.1, X-2.1, X-3.1, X-4.1 in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-2.A-1 to X-1 .1.9-2.A-287, compounds X-2.1.9-
2. A-1 to X-2.I.9-2.A-287, compounds X-3.I.9-2.A-1 to X-3.I.9-2.A-287 compounds X-4.I.9-2.A-1 to X-4.l.9-2.A-287).
Table 9-3 Compounds of the formula X-1.1, X-2.1, X-3.1, X-4.1 in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-3.A-1 to X-1 .1.9-3.A-287, compounds X-2.1.9-
3. A-1 to X-2.I.9-3.A-287, compounds X-3.I.9-3.A-1 to X-3.I.9-3.A-287 compounds X-4.I.9-3.A-1 to X-4.I.9-3.A-287).
Table 9-4 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.I.9-4.A-1 to X-1 .1.9-4.A-287, compounds X-2.1.9-4.A-1 to X- 2.I.9-4.A-287, compounds X-3.I.9-4.A-1 to X-3.I.9-4.A-287 compounds X-4.I.9-4.A-1 to X-4.I.9-
4. A-287).
Table 9-5 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-5.A-1 to X-1 .1.9-5.A-287, compounds X-2.1.9-
5. A-1 to X-2.I.9-5.A-287, compounds X-3.I.9-5.A-1 to X-3.I.9-5.A-287 compounds X-4.I.9-5.A-1 to X-4.I.9-5.A-287).
Table 9-6 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.1.9-6.A-1 to X-1 .1.9-6.A-287, compounds X- 2.I.9-6.A-1 to X-2.I.9-6.A-287, compounds X-3.I.9-6.A-1 to X-3.I.9-6.A-287 compounds X-4.I.9-
6. A-1 to X-4.l.9-6.A-287).
Table 9-7 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.I.9-7.A-1 to X-1 .1.9-7.A-287, compounds X-2.1.9-7.A-1 to X- 2.I.9-7.A-287, compounds X-3.I.9-7.A-1 to X-3.I.9-7.A-287 compounds X-4.I.9-7.A-1 to X-4.I.9-
7. A-287).
Table 9-8 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-8.A-1 to X-1 .1.9-8.A-287, compounds X-2.1.9-
8. A-1 to X-2.I.9-8.A-287, compounds X-3.I.9-8.A-1 to X-3.I.9-8.A-287 compounds X-4.I.9-8.A-1 to X-4.I.9-8.A-287).
Table A
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Figure imgf000121_0001
Figure imgf000122_0001
The compounds I and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
The compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.
Preferably, compounds I and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring. Preferably, treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygen- ase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from an- other class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola,
BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cul- tivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nema- todes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdyster- oid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278,
WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coelop- tera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the Cry1 Ab toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme phosphinothri- cin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the Cry1 Ac toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Pro- tecta®, Bt1 1 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis- related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada).
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); A/ternar/a spp. (Alternaria leaf spot) on vegetables, rape (A. brassico/a or brassi- cae), sugar beets (A tenuis), fruits, rice, soybeans, potatoes (e. g. A. so/an/ or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. (anthracnose) on wheat and A. horde/ on barley; Bipolar/s and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydisj or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokin- iana) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis
(powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana. grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. bet/cola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. soro- kiniana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glo- merella) spp. (anthracnose) on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthrac- nose stalk rot), soft fruits, potatoes (e. g. C. coccodes. black dot), beans (e. g. C. lindemuthi- anum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cy- cloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. lirio- dendri, teleomorph: Neonectria liriodendri. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D.
phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyr- enophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis. tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formiti- poria (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeo- acremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Ery- siphe spp. (powdery mildew) on sugar beets {E. betae), vegetables (e. g. E. pis/), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. gra- minearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. so/ani( sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibber- ella spp. on cereals (e. g. G. zeae) and rice (e. g. G fujikuroi. Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G gossypiion cotton; Grainstaining complex on rice; G 'uignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp . (syn. Drechslera, teleomorph: Cochiioboius) on corn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseo/ή (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco {P. tabacina) and soybeans (e. g. P. manshurica);
Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Phy- soderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P.
megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad- leaved trees (e. g. P. ramorum. sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mil- dew) on vines and P. halstedii 'on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets {P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapes/a yal- lundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubens/s on cucurbits or P. hum/// on hop; Pseudopezicula tracheiphila (red fire disease or .rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. horde/' (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus sto/on/fer (b\ack mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Saro- cladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. ro/fs/ior S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum
(Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tucker!) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Lepto- sphaeria [syn. Phaeosphaer/a] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. trit/c/ (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis. corn smut) and sugar cane; Venturis spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.
The compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials. The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola pp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coni- ophora pp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Ser- pu/a spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp. , Trichoderma spp. , Alternaria spp. , Paecilomyces spp. and Zygomycetes such as Mucorspp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms. According to the present invention, the term "stored products" is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably "stored products" is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
The compounds I and compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.
The term "plant health" is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.
The compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
The compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting.
The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
The compounds I, their N-oxides and salts can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), cap- sules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal articles (e. g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e. g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and am- photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, es- ters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolygluco- sides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e. g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e. g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e. g. alizarin-, azo- and phthalogencyanine colorants).
Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a compound I and 5-15 wt% wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a compound I and 1-10 wt% dispersant (e. g. polyvinyl pyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a compound I and 5-10 wt% emulsifiers (e. g. calcium dodecylbenzenesul- fonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a compound I and 1 -10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e. g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1- 2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a compound I are ground in a rotor-stator mill with addition of 1 -5 wt% disper- sants (e. g. sodium lignosulfonate), 1 -3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1 -5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
ix) Microemulsion (ME)
5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid di- methyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and ar- ylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocya- nate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e. g. hexameth- ylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 - 10 wt%. The wt% relate to the total CS composition.
xi) Dustable powders (DP, DS)
1 -10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.
xii) Granules (GR, FG)
0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed.
xiii) Ultra-low volume liquids (UL)
1 -50 wt% of a compound I are dissolved in organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%.
The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% col-
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treat- ment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1 .
A pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant path- ogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term "pesticide" includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that re- duce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemi- cal composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the composition according to the in- vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal compo- sition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.
The following list of pesticides II (e. g. pesticidally-active substances and biopesticides), in conjunction with which the compounds I can be used, is intended to illustrate the possible combina- tions but does not limit them:
A) Respiration inhibitors
Inhibitors of complex III at Q0 site: azoxystrobin (A.1 .1 ), coumethoxystrobin (A.1.2), coumoxystrobin (A.1 .3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), man- destrobin (A.1 .10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1 .12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1 .17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-meth- oxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1 .19), triclopyricarb/chlorodincarb (A.1 .20), famoxadone (A.1 .21 ), fenamidone (A.1.21 ), methyl-/V-[2-[(1 ,4-dimethyl-5-phenyl- pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), 1-[2-[[1 -(4-chlorophenyl)py- razol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1 .25), ( 2 )-5-[1 -(2,4-di- chlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino- y3-dimethyl-pent-v3-enamide (A.1.34), (Zi2£)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-m
(A.1 .35), pyriminostrobin (A.1.36), bifujunzhi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxy- methylen)phenyl)-3-methoxy-acrylic acid methylester (A.1.38);
- inhibitors of complex III at Q, site: cyazofamid (A.2.1 ), amisulbrom (A.2.2),
[(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-di- oxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2, 3), fenpicoxamid (A.2.4);
- inhibitors of complex II: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), ox- ycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyra- ziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 ), inpyrfluxam (A.3.22), /V-[(22)-2-[3-chloro-5-(2-cyclopropylethynyl)-2-pyridyl]-2-isopropoxyimino-ethyl]-3- (difluoromethyl)-1 -methyl-pyrazole-4-carboxamide (A.3.23), fluindapyr (A.3.28), methyl (E)-2- [2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), isoflu- cypram (A.3.31 ), 2-(difluoromethyl)-N-(1 ,1 ,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1 ,1 ,3-trimethylindan-4-yl]pyridine-3-carboxamide
(A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1 ,1 -dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1 ,1 -dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carbox- amide (A.3.39);
- other respiration inhibitors: diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), di- nobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone
(A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); silthiofam (A.4.12);
B) Sterol biosynthesis inhibitors (SBI fungicides)
- C14 demethylase inhibitors: triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromucona- zole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1 .6), dinicona- zole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1 .9), fluquinconazole (B.1.10), flusi- lazole (B.1 .1 1 ), flutriafol (B.1 .12), hexaconazole (B.1 .13), imibenconazole (B.1.14), ipcona- zole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1 .19), paclobu- trazole (B.1 .20), penconazole (B.1.21 ), propiconazole (B.1 .22), prothioconazole (B.1 .23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1 .26), triadimefon (B.1 .27), triadimenol (B.1.28), triticonazole (B.1 .29), uniconazole (B.1 .30), 2-(2,4-difluorophenyl)-1 ,1 - difluoro-3-(tetrazol-1 -yl)-1 -[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31 ), 2-(2,4-difluorophenyl)-1 ,1-difluoro-3-(tetrazol-1-yl)-1 -[5-[4-(trifluoromethoxy)phenyl]-2- pyridyl]propan-2-ol (B.1.32), ipfentrifluconazole (B.1 .37), mefentrifluconazole (B.1.38), 2- (chloromethyl)-2-methyl-5-(p-tolylmethyl)-1 -(1 ,2,4-triazol-1 -ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1 .44), pefurazoate (B.1.45), prochloraz (B.1 .46), triflumizol (B.1.47); pyrimidines, pyridines and piperazines: fenarimol (B.1 .49), pyrifenox (B.1.50), triforine (B.1.51 ), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)met nol (B.1.52);
- Delta 14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spi- roxamine (B.2.8);
- Inhibitors of 3-keto reductase: fenhexamid (B.3.1 );
- Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1 );
C) Nucleic acid synthesis inhibitors
- phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiralaxyl (C.1 .3), metalaxyl (C.1 .4), metalaxyl-M (C.1 .5), ofurace (C.1 .6), oxadixyl (C.1 .7);
- other nucleic acid synthesis inhibitors: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
D) Inhibitors of cell division and cytoskeleton
- tubulin inhibitors: benomyl (D.1 .1 ), carbendazim (D.1 .2), fuberidazole (D1.3), thiabendazole (D.1 .4), thiophanate-methyl (D.1 .5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyri- dazine (D.1 .6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1 .7), N-eth- yl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1 .9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- N-(2-fluoroethyl)butanamide (D.1 .10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroeth- yl)-2-methoxy-acetamide (D.1 .1 1 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanam- ide (D.1 .12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1 .16);
- other cell division inhibitors: diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);
E) Inhibitors of amino acid and protein synthesis
- methionine synthesis inhibitors: cyprodinil (E.1 .1 ), mepanipyrim (E.1.2), pyrimethanil (E.1.3);
- protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hydro- chloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
F) Signal transduction inhibitors
- MAP / histidine kinase inhibitors: fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1 .3), vinclozolin (F.1 .4), fludioxonil (F.1 .5);
- G protein inhibitors: quinoxyfen (F.2.1 );
G) Lipid and membrane synthesis inhibitors - Phospholipid biosynthesis inhibitors: edifenphos (G.1.1 ), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);
- lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
- phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);
- compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 );
- inhibitors of oxysterol binding protein: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1 -{[3,5-bis(difluorome- thyl-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1 -{[3, 5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperi- din-4-yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl- pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-pi- peridyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.5), 4-[1 -[2-[3-(difluoromethyl)-5-(trifluoro- methyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.6), 4-[1- [2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N- tetralin-1 -yl-pyridine-2-carboxamide (G.5.8), 4-[1 -[2-[5-(difluoromethyl)-3-(trifluoromethyl)py- razol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1 -[2-[3,5- bis(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin- 1 -yl-pyridine-2-carboxamide (G.5.1 1 );
H) Inhibitors with Multi Site Action
- inorganic active substances: Bordeaux mixture (H.1 .1 ), copper (H.1 .2), copper acetate
(H.1 .3), copper hydroxide (H.1 .4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1 .7);
- thio- and dithiocarbamates: ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam
(H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
- organochlorine compounds: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 );
- guanidines and others: guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3),
guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10);
I) Cell wall synthesis inhibitors
- inhibitors of glucan synthesis: validamycin (1.1 .1 ), polyoxin B (1.1.2);
- melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (I.2.3), dicy- clomet (I.2.4), fenoxanil (I.2.5); J) Plant defence inducers
- acibenzolar-S-methyl (J.1 .1 ), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadi- one-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1 .7), phosphorous acid and its salts (J.1 .8), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-di- methoxyphenyl)thiadiazole-5-carboxamide (J.1 .10);
K) Unknown mode of action
- bronopol (K.1.1 ), chinomethionat (K.1 .2), cyflufenamid (K.1 .3), cymoxanil (K.1 .4), dazomet (K.1.5), debacarb (K.1.6), diclocymet (K.1.7), diclomezine (K.1 .8), difenzoquat (K.1 .9), difen- zoquat-methylsulfate (K.1 .10), diphenylamin (K.1.1 1 ), fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover (K.1.14), flusulfamide (K.1 .15), flutianil (K.1.16), harpin (K.1 .17), metha- sulfocarb (K.1 .18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21 ), oxin- copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24), tecloftalam (K.1 .25), triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-eth- yl-N-methyl formamidine (K.1 .28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1 ,2,4-thiadiazol-5-yl]- oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2- yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N'-[5-bromo-6-[1 -(3,5-diflu- orophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1 .31 ), N'-[5-bromo- 6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl- N-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol- 5-yl]-2-prop-2-ynyloxy-acetamide (K.1 .36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin- 3-yl]-pyridine (pyrisoxazole) (K.1 .37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]- pyridine (K.1.38), 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1 .40), picarbutrazox (K.1.41 ), pentyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carba- mate (K.1 .42), but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxyme- thyl]-2-pyridyl]carbamate (K.1 .43), 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phe- nyl]propan-2-ol (K.1.44), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol (K.1.45), quinofumelin (K.1.47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1 ,4-benzoxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1 .50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-me- thyl-2-pyridyl]quinazoline (K.1.51 ), 3-[(3,4-dichloroisothiazol-5-yl)methoxy]-1 ,2-benzothiazole 1 ,1 -dioxide (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine (K.1.53), pyrifenamine (K.1 .54);
M) Growth regulators
abscisic acid (M.1.1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dime- thipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gib- berellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadi- one-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;
N) Herbicides from classes N.1 to N.15
N.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium, butroxydim, clethodim,
clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop- methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop- butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P- methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepra- loxydim, tralkoxydim, 4-(4'-chloro-4-cyclo-,propyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy- 2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopro- pyl[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337- 45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-py- ran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tet- ramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cy- clopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-3,6-dihy- dro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-bi- phenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1 ); 5-(acet- yloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-
3- one (CAS 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihy- dro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51 -1 );
4- (2',4'-dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-
5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS
1312340-83-2); 4-(2',4'-dichloro-4-ethyh[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-
5- 0X0-2 H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
N.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethamet- sulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfu- ron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosul- furon-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfu- ron, triflusulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imaza- mox, imazapic, imazapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, di- closulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam; bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, py- rithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]- benzoic acid-1-methyhethyl ester (CAS 420138-41 -6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- ny oxyJphenylJ-'methylJamirioJ-berizoic acid propyl ester (CAS 420138-40-5), N-(4-bromo- phenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01 -8); flu- carbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thien- carbazone, thiencarbazone-methyl; triafamone;
N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine; ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, pro- pazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, sidu- ron, tebuthiuron, thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham- ethyl, bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, pro- panil; diquat, diquat-dibromide, paraquat, paraquat-dichloride, paraquat-dimetilsulfate;
N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, ben- carbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlor- methoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pen- tyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrim- idin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6), N-ethyl-3-(2,6-dichloro-4-tri- fluoro-methylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide (CAS 452098-92-9), N tetrahy- drofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyhphenoxy)-5-methyl-1 H- pyrazole-1-carboxamide (CAS 452099-05-7), N tetrahydro-"furfuryl-3-(2-chloro-6-fluoro-4- trifluoro-,methylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7- fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-
[1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihy- dro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 13001 18-96-0),
1 - methyl-6-trifluoro-,methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-ben- zo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), methyl (E)-4-[2-chloro- 5-[4-chloro-5-(difluoromethoxy)-1 H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-
2- enoate (CAS 948893-00-3), 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazol-4-yl]- 1 -methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS 212754-02-4);
N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,
norflurazon, picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl)_,pyrimi- dine (CAS 180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintri- one, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltri- one, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon; N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate-potas- sium, glyphosate-trimesium (sulfosate);
N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;
N.8 DHP synthase inhibitors: asulam;
N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendi- methalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;
N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethena- mid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, prop- isochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napro- pamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
Figure imgf000141_0001
II.9
II .8 N.1 1 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1 -cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS
175899-01-1 );
N.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;
N.13 Auxinic herbicides: 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as amino- pyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quin- merac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, 4-amino- 3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661 -72-9);
N.14 Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-so- dium;
N.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydra- zide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, me- thyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tridiphane;
O) Insecticides from classes 0.1 to 0.29
0.1 Acetylcholine esterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, bu- tocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; acephate, aza- methiphos, azinphos-ethyl, azinphosmethyl, 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 O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosa- lone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, pro- thiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;
0.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole;
0.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, del- tamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and trans- fluthrin; DDT, methoxychlor;
0.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam;
4,5-dihydro-AAnitro-1-(2-oxiranylmethyl)-1 A/-imidazol-2-amine, (2£)-1-[(6-chloropyridin-3-yl)me- thylJ-AAnitro^-pentylidenehydrazinecarboximidamide; 1-[(6-chloropyridin-3-yl)methyl]-7-me- thyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; nicotine; sulfoxaflor, f I u py rad if u ron e, trif I u mezopy ri m ;
0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetoram;
0.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbe- mectin;
0.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;
0.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;
0.9
Chordotonal organ TRPV channel modulators: pymetrozine, pyrifluquinazon; flonicamid;
O.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin; etoxazole;
0.1 1 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus sphaeri- cus and the insecticdal proteins they produce: Bacillus thuringiensis subsp. israelensis, Ba- cillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp.
kurstaki, Bacillus thuringiensis subsp. tenebrionis, the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 ;
0.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;
0.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfluramid;
0.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium; 0.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron, chlorfluazuron, diflubenzuron, flu- cycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;
0.16 Inhibitors of the chitin biosynthesis type 1 : buprofezin;
0.17 Moulting disruptors: cyromazine;
0.18 Ecdyson receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide;
0.19 Octopamin receptor agonists: amitraz;
O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl,
fluacrypyrim, bifenazate;
0.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, fenpyroximate, pyrim- idifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;
0.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyano- phenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecar- boxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)- amino]phenyl]methylene]-hydrazinecarboxamide;
0.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen, spiromesifen, spirotetramat, spi- ropidion;
0.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium
phosphide, phosphine, zinc phosphide, cyanide;
0.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen;
0.26 Ryanodine receptor-modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cycla- niliprole, tetraniliprole; (R)-3-chloro-N1 -{2-methyl-4-[1 ,2,2,2 -tetrafluoro-l-(trifluoromethyl)- ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro-N1-{2-methyl-4- [1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)- phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]- carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; N-[4,6-dichloro-2-[(diethyl- lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole- 3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl- lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluorometh- yl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carba- moyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-di- bromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluo- romethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-meth- ylphenyl]-3-bromo-1 -(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloro- 2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1 -methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole- 5-carboxamide; 3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyri- dyl)-1 H-pyrazole-5-carboxamide; N-[4-chloro-2-[[(1 ,1 -dimethylethyl)amino]carbonyl]-6-meth- ylphenyl]-1 -(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; cyhalodi- amide;
7: Chordotonal organ Modulators - undefined target site: flonicamid;
8. insecticidal active compounds of unknown or uncertain mode of action: afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chinome- thionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-1 1 -en- 10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2- one, 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, Bacillus
Figure imgf000145_0001
flupyrimin,fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(tri- fluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; fluxametamide; 5- [3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; 3-(benzoylmethyla- mino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phe- nyl]-2-fluoro-benzamide; 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide; N-[3-[[[2-iodo-4-[1 ,2,2,2-tetra- fluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl- benzamide; N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluorome- thyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide; 4-fluoro-N-[2- fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phe- nyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 , 2,2,2- tetrafluoro-1-(trifluoromethyl)ethyl]-6(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-me- thyl-benzamide; 2-chloro-N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(tri- fluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide; 4-cyano-N-[2-cyano-5- [[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2- methyl-benzamide; 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4- [1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide; N-[5-[[2-chloro- 6-cyano-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phe- nyl]-4-cyano-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1 -(tri- fluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; N-[5- [[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2- cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4- [1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-ben- zamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluorome- thyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2- tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-ben- zamide; 2-(1 ,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridi- nyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimi- dine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-methylsulfonyl- 6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-ethyl-N-[4-methyl-2-(3-pyridyl)thiazol- 5-yl]-3-methylthio-propanamide; N-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; N,2-dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-[4- chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide; N-[4-chloro-2- (3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide; N-[4-chloro-2-(3-pyridyl)thia- zol-5-yl]-N-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3- methylthio-propanamide; 1 -[(6-chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy- 7-methyl-8-nitro-imidazo[1 ,2-a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; 1 -(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole- 4-carboxamide; N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4- carboxamide; 1 -[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-car- boxamide; 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1- [1-(1 -cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; N-me- thyl-1-(2-fluoro-1 -methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4- difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4-difluo- rocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, N-(1-methylethyl)-2-(3- pyridinyl)-2H-indazole-4-carboxamide; N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carbox- amide; N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-(2,2,2-tri- fluoroethyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H- indazole-5-carboxamide; methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecar- boxylate; N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; N- (2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; 2-(3-pyridinyl )-N-(2-pyrimidi- nylmethyl )-2H-indazole-5-carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H- indazole-5-carboxamidetyclopyrazoflor; N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-
3- (3,3,3-trifluoropropylsulfinyl)propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-di- fluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol- 4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide; sarolaner, lotilaner, /V- [4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2-pentafluoroethyl)-
4- (trifluoromethyl)-1 A/-pyrazole-5-carboxamide; M. UN.22a 2-(3-ethylsulfonyl-2-pyridyl)-3-me- thyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]- 3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 4-[5-(3,5-dichlorophenyl)-5-(trifluorome- thyl)-4 isoxazol-3-yl]-N[(4 )-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide, 4-[5- (3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4 isoxazol-3-yl]-/V-[(4 )-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide; /V-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-me- thyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide, /V-[4-chloro-3- [(1 -cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoro- methyl)pyrazole-3-carboxamide; acynonapyr; benzpyrimoxan; chloro-/V-(1 -cyanocyclopro- pyl)-5-[1-[2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4- yl]benzamide.
The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;
EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244,
JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272;
US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271 , WO 1 1/028657, WO 12/168188, WO 07/006670, WO 1 1/77514; WO 13/047749, WO 10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441 , WO 13/162072, WO 13/092224, WO 1 1/135833, CN 1907024, CN 1456054, CN 103387541 , CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/1 16251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/16551 1 , WO 1 1/081 174, WO 13/47441 ).
The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier. Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi. Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to K).
By applying compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, i.e. more then simple addition of the individual effects is obtained (synergistic mixtures).
This can be obtained by applying the compounds I and at least one further active substance simultaneously, either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.
When applying compound I and a pesticide II sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1 .5 hours to 5 days, even more preferred from 2 hours to 1 day.
In the binary mixtures and compositions according to the invention the weight ratio of the component 1 ) and the component 2) generally depends from the properties of the active com- ponents used, usually it is in the range of from 1 :10,000 to 10,000:1 , often it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50: 1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 , even more preferably in the range of from 1 :4 to 4:1 and in particular in the range of from 1 :2 to 2:1.
According to further embodiments of the binary mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 1000:1 to 1:1, often in the range of from 100: 1 to 1:1, regularly in the range of from 50:1 to 1:1, preferably in the range of from 20:1 to 1:1, more preferably in the range of from 10:1 to 1:1, even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1:1.
According to a further embodiments of the binary mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 1:1 to 1:1000, often in the range of from 1:1 to 1:100, regularly in the range of from 1:1 to 1:50, preferably in the range of from 1:1 to 1:20, more preferably in the range of from 1:1 to 1:10, even more preferably in the range of from 1:1 to 1:4 and in particular in the range of from 1:1 to 1:2.
In the ternary mixtures, i.e. compositions according to the invention comprising the component 1) and component 2) and a compound III (component 3), the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of from 1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component 1 ) and component 3) usually it is in the range of from 1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and in particular in the range of from 1:4 to 4:1.
Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the component 1).
These ratios are also suitable for inventive mixtures applied by seed treatment. Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q0 site in group A), more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A.1.25 (A.1.34) and (A.1.35); particularly selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.25), (A.1.34) and (A.1.35).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q, site in group A), more preferably selected from compounds (A.2.1), (A.2.3) and (A.2.4); particularly selected from (A.2.3) and (A.2.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex II in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.28), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39); particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from other respiration nhibitors in group A), more preferably selected from compounds (A.4.5) and (A.4.1 1 ); in particular (A.4.1 1 ).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from C14 demethylase inhibitors in group B), more preferably selected from compounds (B.1 .4), (B.1 .5), (B.1 .8), (B.1 .10), (B.1.1 1 ), (B.1 .12), (B.1.13), (B.1 .17), (B.1.18), (B.1 .21 ), (B.1.22), (B.1.23), (B.1 .25), (B.1.26), (B.1 .29), (B.1.34), (B.1 .37), (B.1.38), (B.1 .43) and (B.1 .46); particularly selected from (B.1.5), (B.1.8), (B.1 .10), (B.1.17), (B.1.22), (B.1.23), (B.1 .25), (B.1.33), (B.1 .34), (B.1.37), (B.138), (B.1.43) and (B.1.46).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from Delta 14-reductase inhibitors in group B), more preferably selected from com- pounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from phenylamides and acyl amino acid fungicides in group C), more preferably selected from compounds (C.1 .1 ), (C.1 .2), (C.1.4) and (C.1.5); particularly selected from (C.1 .1 ) and (C.1.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from other nucleic acid synthesis inhibitors in group C), more preferably selected from compounds (C.2.6),(C.2.7) and (C.2.8).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1 ), (D.1 .2), (D.1.5), (D.2.4) and (D.2.6); particularly selected from (D.1 .2), (D.1.5) and (D.2.6).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group E), more preferably selected from compounds (E.1.1 ), (E.1.3), (E.2.2) and (E.2.3); in particular (E.1.3).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group F), more preferably selected from compounds (F.1.2), (F.1.4) and (F.1.5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group G), more preferably selected from compounds (G.3.1 ), (G.3.3), (G.3.6), (G.5.1 ), (G.5.2), (G.5.3), (G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), (G.5.10) and (G.5.1 1 ); particularly selected from (G.3.1 ), (G.5.1 ), (G.5.2) and (G.5.3).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group H), more preferably selected from compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group I), more preferably selected from compounds (1.2.2) and (I.2.5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group J), more preferably selected from compounds (J.1 .2), (J.1.5) and (J.1 .8); in particular (J.1.5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group K), more preferably selected from compounds (K.1.41 ), (K.1 .42), (K.1.44), (K.1 .45), (K.1.47) and (K.1.49); particularly selected from (K.1 .41 ), (K.1.44), (K.1 .45), (K.1.47) and (K.1 .49).
The mixtures of active substances can be prepared as compositions comprising besides the ac- tive ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given for the compositions of compounds I. Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I.
Synthesis example
With due modification of the starting compounds, the procedures shown in the synthesis exam- pies below were used to obtain further compounds I. The resulting compounds, together with physical data, are listed in Table I below.
HPLC-MS: HPLC-column Kinetex XB C18 1 ,7μ (50 x 2,1 mm); eluent: acetonitrile / water + 0.1 % TFA (5 gradient from 5:95 to 100 : 0 in 1.5 min at 60°C, flow gradient from 0.8 to 1.0 ml/min in 1 .5 min). MS: Quadrupol Electrospray lonisation, 80 V (positive mode).
Example 1 ) Synthesis of 1 -(5,6-dimethyl-3-pyridyl)-3-methyl-3-(3-pyridyl)-4H-isoquinoline (1-1 )
2,0 g of trifluoromethane sulfonic acid was added dropwise to a mixture of 0,26 g (2 mmol) 5,6- dimethylpyridine-3-carbonitrile and 0,650 g (3 mmol) 1 -phenyl-2-(3-pyridyl)propan-2-ol in 50 mL dichloroethane at 0 - 5°C. After 3 h at room temperature the reaction mixture was poured onto sodium carbonate solution, the organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were extracted with sodium hydrogen carbonate and water, evaporated and the residue was purified via MPLC with water/ace- tonitrile mixtures to yield 0,1 19 g (18 %) of the title compound as a light yellow oil.
1H-NMR (CDCIs, δ in ppm): 8,8 ( d, 1 H); 8,6 (s, 1 H); 8,4 (d, 1 H); 7,9 (d, 1 H); 7,8 (s, 1 H); 7,4 (m, 1 H); 7,3-7,2 (m, 3H); 3,3 (d, 1 H); 3,1 (d, 1 H); 2,6 (s, 3H); 2,4 (d, 3H); 1 ,6 (s, 3H).
*HPLC-MS: Rt = 0,641 min; M++H = 328,1
Example 2) Synthesis of 3-(3,3-dichloroallyl)-1 -[6-(difluoromethyl)-5-methyl-3-pyridyl]-3-methyl- 4H-isoquinoline (I-5)
1. Synthesis of 2-(2,2-dichlorocyclopropyl)-1 -phenyl-propan-2-ol
The mixture of 2,2-dichlorocyclopropyl methyl ketone (2,645 g, 18.8 mmol) in THF (100 mL) was added BnMgCI (56,3mL, 56,3 mmol) dropwise at 0 °C under N2, the mixture was stirred for 3 h at 0 °C. The reaction mixture was quenched with aq. NH4CI (50 mL) and extracted with MTBE (50 mL), dried over Na2S04 and concentrated, the residue was purified by column
(PE:EtOAc=40:1 ) to give the tittle compound (2.7 g, 60%) as yellow oil.
H-NMR (CDCIs, δ in ppm): 1.43 - 1.54 (m, 3 H) 1 .58 (dd, J=8.38, 7.06 Hz, 1 H) 1 .65 - 1.72 (m, 1 H) 2.81 - 2.93 (m, 2H) 7.13 - 7.42 (m, 5 H)
2. Synthesis of [(1 E)-5,5-dichloro-2-methyl-penta-1 ,4-dienyl]benzene
The solution of 2-(2,2-dichlorocyclopropyl)-1-phenyl-propan-2-ol (0,4 g, 1 ,64 mmol) in toluene (20 mL) was added p-TsOH (156 mg, 0,82 mmol) under N2, the solution was heated to 80 oC for 16 h. The reaction mixture was concentrated, the residue was purified by column (PE) to give the tittle compound (254 mg, crude) as colorless oil.
3. Synthesis of methyl 5-[3-(3,3-dichloroallyl)-3-methyl-4H-isoquinolin-1-yl]-3-methyl-pyridine-2-car- boxylate
The solution of methyl 5-cyano-3-methyl-pyridine-2-carboxylate (105 mg, 0.6 mmol) and [(1 E)-
5.5- dichloro-2-methyl-penta-1 ,4-dienyl]benzene (270 mg, 1.2 mmol) were in DCM (20 mL) was added TfOH (450 mg, 3 mmol) dropwise at 0 oC under N2, the mixture was stirred for 1 .5 h at 0 °C. The reaction mixture was quenched with aq. NaHCC>3 (30 mL) and extracted with DCM (20 mL), the organic layer was dried over Na2S04 and concentrated, the residue was purified by Pre-TLC (PE:EtOAc=1 :1 ) to give the tittle compound (1 1 1 mg, 46%) as red oil.
1H-NMR (CDCIs, δ in ppm): 1.22 (s, 3 H) 2.43 - 2.58 (m, 2 H) 2.66 (s, 3 H) 2.73 - 2.93 (m, 2 H) 3.96 - 4.04 (m, 3 H), 6.01 - 6.09 (m, 1 H) 7.14 (d, J=7.50 Hz, 1 H) 7.21 - 7.28 (m, 2 H) 7.37 - 7.46 (m, 1 H) 7.85 (s, 1 H) 8.69 (s, 1 H)
4. Synthesis of 5-[3-(3,3-dichloroallyl)-3-methyl-4H-isoquinolin-1 -yl]-3-methyl-pyridine-2- carbaldehyde
The mixture of 5-[3-(3,3-dichloroallyl)-3-methyl-4H-isoquinolin-1-yl]-3-methyl-pyridine-2-carbox- ylic acid (360 mg, 0,89 mmol) in DCM (20 mL) was added DIBAL-H (1 ,34 mL, 1 ,34 mmol) drop- wise at -78 °C under N2, the mixture was stirred for 1 h at -78 °C. The reaction mixture was quenched with aq. NH4CI (30 mL) and extracted with DCM (30 mL), dried over Na2S04 and con- centrated to give the tittle compound (360 mg, crude) as yellow solid.
1H-NMR (CDCI3, δ in ppm): 2.37 (s, 5 H) 2.47 - 2.60 (m, 3 H) 2.74 (s, 3 H) 2.77 - 2.95 (m, 3 H) 6.08 (t, J=7.59 Hz, 1 H), 7.40 - 7.48 (m, 1 H) 7.85 (s, 1 H) 8.83 (s, 1 H) 10.27 (s, 1 H)
5. Synthesis of 3-(3,3-dichloroallyl)-1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-3-methyl-4H-iso- quinoline
The solution of 5-[3-(3,3-dichloroallyl)-3-methyl-4H-isoquinolin-1 -yl]-3-methyl-pyridine-2-carbal- dehyde (0,5 g, 1 ,34 mmol) in DCM (40 mL) was added DAST (1 ,534 g, 6,7 mmol) dropwise at 0 °C under N2, the solution was stirred for 1 h at 0°C. The reaction mixture was quenched with aq. NaHCC>3 (60 mL) and extracted with DCM (30 mL), dried over Na2S04 and concentrated, the residue was purified by Pre-TLC (PE:EtOAc=3:1 ) to give tittle compound (180 mg, 34%) as col- orless oil.
1H-NMR (CDCI3, δ in ppm): 1.24 (s, 3 H) 2.46 - 2.57 (m, 2 H) 2.59 (s, 3 H) 2.76 - 2.95 (m, 2 H) 6.07 (t, J=7.59 Hz, 1 H), 6.61 - 6.90 (m, 1 H) 7.17 (d, J=8.03 Hz, 1 H) 7.25 (br. s., 1 H) 7.29 (s, 1 H) 7.41 - 7.46 (m, 1 H) 7.83 (s, 1 H) 8.61 (s, 1 H)
*HPLC-MS: Rt = 1 ,097 min; M++H = 394,9
Example 3) Synthesis of 1 -(5,6-dimethyl-3-pyridyl)spiro[4H-isoquinoline-3,1 -cydopentane] (I-8)
1 ,5 g of trifluoromethane sulfonic acid was added dropwise to a mixture of 0,33 g (2,5 mmol)
5.6- dimethylpyridine-3-carbonitrile and 0,49 g (2,8 mmol) 2— phenylcyclohexanol in 15 mL di- chloroethane at 0 - 5°C. After 12 h at room temperature the reaction mixture was poured onto sodium carbonate solution, the organic layer was separated and the aqueous layer was ex- traded with dichloromethane. The combined organic extracts were extracted with sodium hydrogen carbonate and water, evaporated and the residue was purified via silica gel column chromatography with heptane/ethyl acetate mixtures to yield 0,17 g (24 %) of the title compound as a light yellow oil.
H-NMR (CDCIs, δ in ppm): 8,5 (s, 1 H); 7,6 (s, 1 H); 7,3 (d, 1 H); 7,2-7,1 (m, 2H); 2,8 (s, 2H); 2,6 (s, 3H);2,3 (s, 3H); 1 ,9 (br t, 2H), 1 ,8 (t, 2H); 1 ,6 (m, 4H)
*HPLC-MS: Rt = 0,746 min; M++H = 291 ,2
With due modification of the starting compounds, the procedures shown in the synthesis examples below were used to obtain further compounds I. The resulting compounds, together with physical data, are listed in Table I below.
Table I:
Figure imgf000152_0001
Table I:
Figure imgf000152_0002
Figure imgf000153_0001
0,83 min;
I-22 H H CHs # CHF2 CHs 0 - M++H=345
0,861 min;
I-23 H H CHs CHF2 CHs 0 - M++H=313
^O H 0,74 min;
I-24 H H CHs # CHF2 CHs 0 - M++H=317
1 ,104 min;
I-25 H H CHs CHF2 CHs 0 -
# M++H=312,1
1 ,042 min;
I-26 H H CHs CHF2 CHs 0 -
# M++H=31 1
0,984 min;
I-27 H H CHs # CHF2 CHs 1 6-F
M++H=367,1
1 ,099 min;
I-28 H H CHs ft CHF2 CHs 1 6-F
# M++H=330
/—F 0,910 min;
I-29 H H CHs # CHF2 CHs 0 - M++H=319,1
0,961 min;
I-30 H H CHs # CHF2 CHs 1 6-F
M++H=337,1
CI
CHs 0,921 min;
1-31 H H CHs CHs 0 -
# M++H=395
HPLC-MS: HPLC-column Kinetex XB C18 1 ,7μ (50 x 2,1 mm); eluent: acetonitrile / water + 0.1 % TFA (5 gradient from 5:95 to 100 : 0 in 1.5 min at 60°C, flow gradient from 0.8 to 1.0 ml/min in 1.5 min). MS: Quadrupol Electrospray lonisation, 80 V (positive mode). II. Biological trials
Microtest
The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. Example 1 - Activity against the grey mold Botrytis cinerea in the microtiterplate test
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Botrci cinerea in a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.
In this test, the samples which had been treated with 31 ppm of the active substance from examples I-2, I-3, I-5, I-6, I-7, I-9, 1-10, 1-1 1 , 1-13, 1-14, 1-15, 1-17, 1-18, 1-19, I-20, 1-21 , I-22, I-23, I- 24 and I-29 respectively, showed up to at most 9 % growth of the pathogen. Example 2 - Activity against Fusarium culmorum in the microtiterplate test
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Fusarium culmorum in an aqueous biomalt or yeast-bactopeptone-glycerine solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
In this test, the samples which had been treated with 31 ppm of the active substance from examples I-3, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-15, 1-18, 1-21 and I-23 respectively, showed up to at most 16 % growth of the pathogen
Example 3 - Activity against rice blast Pyricularia oryzae in the microtiterplate test
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Pyricularia oryzae in a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.
In this test, the samples which had been treated with 31 ppm of the active substance from 1-1 , I- 3, I-4, I-5, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14 ,1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I-22, I-23, I- 24 and I-29 respectively, showed up to at most 13 % growth of the pathogen.
Example 4 - Activity against leaf blotch on wheat caused by Septoria tritici The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Septoria tritici Ίη a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.
In this test, the samples which had been treated with 31 ppm of the active substance from examples I-3, I-5, I-6, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-18, 1-19, I-20, 1-21 , I-23 and I-29 respectively, showed up to at most 13 % growth of the pathogen. The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds.
Green House
The spray solutions were prepared in several steps:
The stock solution were prepared: a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a relation (volume) sol- vent-emulsifier of 99 to 1 was added to 25 mg of the compound to give a total of 5 ml. Water was then added to total volume of 100 ml.
This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration.
Example 1 - Preventative fungicidal control of Botrytis cinerea on leaves of green pepper
Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The next day the plants were inoculated with an aqueous biomalt solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24· C and a relative humidity close to 100 % the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
In this test, the samples which had been treated with 250 ppm of the active substance from examples 1-14, 1-15, 1-19, I-20, 1-21 , I-22, I-23, I-25, I-26, I-27, I-28 and I-30 respectively, showed up to at most 1 1 % growth of the pathogen whereas the untreated plants were 80% infected. Example 2 - Long lasting control of Botrytis cinerea on leaves of green pepper
Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The plants were then cultivated in the greenhouse for 7 days and then inoculated with an aqueous biomalt solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24· C and a relative humidity close to 100 % the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
In this test, the samples which had been treated with 250 ppm of the active substance from examples I-3, I-5, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-19, I-20, 1-21 , I-26 and I-27 respectively, showed up to at most 13 % growth of the pathogen whereas the untreated plants were 80% infected.
III. Comparative Examples Microtest
The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
Example 1 - Activity against the grey mold Botrytis cinerea in the microtiterplate test
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Botrci cinerea in a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation. Growth (%) at
Compound Structure
8 ppm
State of the art 36
Figure imgf000157_0001
I-3 1
1-1 1 0
Example 2 - Activity against Fusanum culmorum in the microtiterplate test
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Fusarium culmorum in an aqueous biomalt or yeast-bactopeptone-glycerine solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
Growth (%)
Compound Structure
at 31 ppm
State oft he art 58
Figure imgf000158_0001
Example 3 - Activity against rice blast Pynculana oryzae in the microtiterplate test
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Pyricularia oryzae in a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.
Growth (%) at 0.5
Compound Structure
PPm
State of the art 60
Figure imgf000158_0002
I-3 1
Figure imgf000159_0001
Example 4 - Activity against leaf blotch on wheat caused by Septoria tritid
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Septoria tritici'm a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.
Figure imgf000159_0002
Green House
The spray solutions were prepared in several steps: The stock solution were prepared: a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a relation (volume) sol- vent-emulsifier of 99 to 1 was added to 25 mg of the compound to give a total of 5 ml.
Water was then added to total volume of 100 ml.
This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration.
Example 1 - Long lasting control of Botrytis cinema on leaves of green pepper
Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The plants were then cultivated in the greenhouse for 7 days and then inoculated with an aqueous biomalt solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24°C and a relative humidity close to 100 % the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
Figure imgf000160_0001

Claims

Claims
1. Compounds of formula I
Figure imgf000161_0001
wherein
is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 are unsubstituted or substituted by groups R1a which independently of one another are selected from:
R1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4 halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or
substituted by groups R1 b which independently of one another are selected from:
R1 b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio; is in each case independently selected from H, halogen, OH, CN, N02, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; wherein the acyclic moieties of R2 are unsubstituted or substituted by groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted or substituted by substituents R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or
substituted by groups R2b which independently of one another are selected from: R2b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl,
C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R3 is in each case independently selected from CH3, CH2F, CHF2 and CF3;
R4 is independently selected from CN, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogen- alkynyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-halogenalkoxy, CH(=0),
C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R' and R" are independently selected from H, C1-C4- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2- C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci- C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or
wherein the acyclic moieties of R4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R4a, which independently of one another are selected from:
R a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4- alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6- alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N , O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , CN , NO2, SH , N H2, N H(Ci-C4-al- kyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, Ci- C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl; and wherein Rx, R' and R" are as defined above wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R4 are independently unsubstituted or substituted with identical or different groups R4b, which independently of one another are selected from:
R4b halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4- alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , C1-C4- alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
and wherein Rx is as defined above;
n is 0, 1 , 2 or
R3, R4 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N , O and S, wherein the heteroatom N may carry one substituent selected from CrC4-alkyl, CrC4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from CN , Ci-C4-al- kyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or S02, and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R34 independently selected from halogen, OH , CN , N02, SH , N H2, d-Ce-alkyl, Ci-Ce-halogen- alkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, C1-C4- alkoxy-CrC4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R34a selected from the group consisting of CN , halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and
R5 is H ;
R6 is H ;
A is selected from below group:
Figure imgf000164_0001
wherein, the positions of the rings marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I.; wherein Y is H;
o is 0, 1 , 2 or 3; and
R78 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-R*, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy,
Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N, O and S; wherein Rx , R' and R" are as defined above; and wherein the acyclic moieties of R78 are unsubstituted or substituted by R78a which independently of one another are selected from:
R78a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or substituted by R78aa selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubsti- tuted or substituted by R78b which independently of one another are selected from:
R78b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio;
is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H2, N H(Ci- C4-alkyl), N(Ci-C4-alkyl)2, N H (C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4-alkynyl)2, N H(C3-C6-cycloalkyl), N (C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4- alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4- alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n- aryl, Ci-C6-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)N H (Ci- Ce-alkyl), CH(=S), C(=S)C C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- Ce-cycloalkyl, C(=S)N H(C C6-alkyl), C C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3- C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S; wherein
Rx is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, and C3-C6-halogencycloalkyl; wherein the acyclic moieties of R9 are unsubstituted or substituted by groups R9a which independently of one another are selected from:
R9a halogen, OH , CN , CrC6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R9 are unsubstituted or
substituted by groups R9b which independently of one another are selected from:
R9b halogen, OH , CN , C C4-alkyl, C C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
is in each case independently selected from the substituents as defined for R9, wherein the possible substituents for R10 are R10a and R10b , respectively, which correspond to R9a and R9b, respectively;
together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or het- eroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N , O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted by substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and CN ; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R11)m, wherein m is 0, 1 , 2, 3 or 4;
R11 is in each case independently selected from halogen, OH , CN , NO2, SH , N H2, N H(Ci-C4- alkyl), N(Ci-C4-alkyl)2, N H-S02-Rx, d-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;
wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein
Rx is as defined above;
wherein the acyclic moieties of R11 are unsubstituted or substituted with identical or different groups R11a which independently of one another are selected from:
R11a halogen, OH , CN , C C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN , C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R11 unsubstituted or substituted with identical or different groups R11 b which independently of one another are selected from:
R11 b halogen, OH , CN , C C4-alkyl, C C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; with the provisio that f A is phenyl,
R1 is H ; and
R4 can not be unsubstituted Ci-C6-alkyl; and
R10 can not be H
and the N-oxides and the agriculturally acceptable salts thereof.
2. The compounds of claim 1 , wherein
R1 is H ;
R2 is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H2, N H(Ci- C4-alkyl), N(Ci-C4-alkyl)2, N H-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the het- eroaryl contains one, two or three heteroatoms selected from N , O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH , CN , Ci-C4-halogenalkyl, CrC4-alkoxy and CrC4-halogenalkoxy; wherein the acyclic moieties of R2 are unsubstituted or substituted by groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted or substituted by substituents R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or
substituted by groups R2b which independently of one another are selected from: R2b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl,
C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R3 is in each case independently selected from CH3, CH2F, CHF2 and CF3;
R4 is independently selected from CN, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, substituted Ci- C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-halogenalkoxy,
CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6- alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroa- toms selected from N, O and S; and wherein R' and R" are independently selected from H, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four- , five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six- membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halo- genalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci- C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or wherein the acyclic moieties of R4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R4a, which independently of one another are selected from:
R a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4- alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6- alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N , O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , CN , NO2, SH , N H2, N H(Ci-C4-al- kyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, Ci- C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl; and wherein Rx, R' and R" are as defined above wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R4 are independently unsubstituted or substituted with identical or different groups R4b, which independently of one another are selected from:
R4b halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4- alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , C1-C4- alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
and wherein Rx is as defined above;
n is 0, 1 , 2 or
R3, R4 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N , O and S, wherein the heteroatom N may carry one substituent selected from CrC4-alkyl, CrC4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from CN , Ci-C4-al- kyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or S02, and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R34 independently selected from halogen, OH , CN , N02, SH , N H2, d-Ce-alkyl, Ci-Ce-halogen- alkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, C1-C4- alkoxy-CrC4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R34a selected from the group consisting of CN , halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and
R5 is H ;
R6 is H ;
A is selected from below group:
Figure imgf000169_0001
wherein, the positions of the rings marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I.; wherein Y is H;
o is 0, 1 , 2 or 3; and
R78 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-R*, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy,
Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N, O and S; wherein Rx , R' and R" are as defined above; and wherein the acyclic moieties of R78 are unsubstituted or substituted by R78a which independently of one another are selected from:
R78a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or substituted by R78aa selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubsti- tuted or substituted by R78b which independently of one another are selected from:
R78b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio;
is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4-alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4- alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4- alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n- aryl, Ci-C6-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)NH(Ci- Ce-alkyl), CH(=S), C(=S)C C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- Ce-cycloalkyl, C(=S)NH(C C6-alkyl), C C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3- C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, and C3-C6-halogencycloalkyl; wherein the acyclic moieties of R9 are unsubstituted or substituted by groups R9a which independently of one another are selected from:
R9a halogen, OH, CN, CrC6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R9 are unsubstituted or
substituted by groups R9b which independently of one another are selected from:
R9b halogen, OH, CN, C C4-alkyl, C C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
is in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4- alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4-alkenyl), N(Ci- C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-al- kynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl),
NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, d-Ce-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)C C6-al- kyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)NH(Ci-C6- alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6- cycloalkyl, C(=S)NH(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3-C6- cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, and C3-C6-halogencycloalkyl; wherein the acyclic moieties of R10 are unsubstituted or substituted by groups R10a which independently of one another are selected from:
R10a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R101a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R10 are unsubstituted or
substituted by groups R10b which independently of one another are selected from:
R10b halogen, OH, CN, C C4-alkyl, C C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or het- eroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted by substituents selected from C1-C4- alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R11)m, wherein m is 0, 1 , 2, 3 or 4;
is in each case independently selected from halogen, OH, CN, NO2, SH , NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;
wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein
Rx is as defined above;
wherein the acyclic moieties of R11 are unsubstituted or substituted with identical or different groups R11a which independently of one another are selected from:
R11a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R11 unsubstituted or substituted with identical or different groups R11 b which independently of one another are selected from:
R11 b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, CrC4-halogenalkoxy, and Ci-C6-alkylthio;
and the N-oxides and the agriculturally acceptable salts thereof.
The compounds of claims 1 to 2, wherein R2 is hydrogen, F, CI, Br, CN, Ci-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, wherein the acyclic moieties of R2 are unsubtitted or substituted by halogen.
The compounds of claims 1 to 3, wherein R4 is in each case independently selected from CN, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), CR'=NOR", C3-C6-halogencycloalkyl, a saturated three-, four-, five- , six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and Ci-C6-alkyl substituted by CN, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, S(0)n-Ci-C6-alkyl, NH-S02-Rx, NH(Ci-C6-alkyl), N(Ci-C6-alkyl)2, CH(=0), C(=0)Ci-C6- alkyl, C(=0)0(Ci-C6-alkyl), a saturated three-, four-, five-, six-, membered carbocycle, heterocycle or aryl.
The compounds of claims 1 to 4, wherein R4 is in each case independently selected from C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, six-membered heteroaryl or aryl which is unsubstituted or substituted by halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, CN, Ci-C6-alkoxyor Ci-C4-halogenalkoxy.
The compounds of claims 1 to 5, wherein A is
Figure imgf000172_0001
The compounds of any one of claims 1 to 6, wherein R9 and R10 independently are selected from CN, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkynyl, ORY, C3-C6-cy- cloalkyl.
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl or C2-C6-alkynyl.
A process for the synthesis of compounds I of claim 1 , comprising the step of: a) reactin a compound X
Figure imgf000173_0001
X
The intermediate compounds X as defined in claim 8, whererin the definition of the sub- stitutents R1, R2, R3, R4, R5, R6, A, R78, o, R9 and R10 is as defined in claim 1 and 2 with the proviso that if A is phenyl R2 is H.
10. The Intermediate compounds X according to claim 8, with the proviso that if A is phenyl R2 is H or R3 and R4 together with the carbon atom to which they are bound can not form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten- membered carbocycle or heterocycle.
1 1 . A composition, comprising one compound of formula I, as defined in any of the claims 1 to 7, an N-oxide or an agriculturally acceptable salt thereof.
12. The composition according to claim 1 1 , comprising additionally a further active substance.
13. A use of a compound of formula I, as defined in any of the claims 1 to 7, and of an agriculturally acceptable salt thereof or of the compositions, as defined in any of the claims 1 1 or 12, for combating phytopathogenic fungi.
14. A method for combating phytopathogenic fungi, comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I, as defined in any of the claims 1 to 7 or with a composition, as defined in any of the claims 1 1 or 12.
15. Seed, coated with at least one compound of formula I, as defined in any of the claims 1 to 7, and/or an agriculturally acceptable salt thereof or with a composition, as defined in any of the claims 1 1 or 12, in an amount of from 0.1 to 10 kg per 100 kg of seed.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019115343A1 (en) * 2017-12-15 2019-06-20 Basf Se Fungicidal mixture comprising substituted pyridines
WO2022073932A1 (en) * 2020-10-05 2022-04-14 Syngenta Crop Protection Ag Fungicidal compositions
US11425910B2 (en) 2017-02-21 2022-08-30 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US11820747B2 (en) 2021-11-02 2023-11-21 Flare Therapeutics Inc. PPARG inverse agonists and uses thereof

Citations (104)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
WO1983003968A1 (en) 1982-05-18 1983-11-24 University Of Florida Brain-specific drug delivery
EP0141317A2 (en) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them
EP0152031A2 (en) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Azolyl cycloalkanol derivatives and agricultural fungicides
EP0226917A1 (en) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Acrylic acid esters and fungicides containing these compounds
EP0243970A1 (en) 1986-05-02 1987-11-04 Stauffer Chemical Company Fungicidal pyridyl imidates
EP0256503A2 (en) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Pyridinecarboxamide derivatives and their use as fungicide
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en) 1989-03-24 1990-10-17 Ciba-Geigy Ag Disease-resistant transgenic plants
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
EP0428941A1 (en) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Hexahydrotriazine compounds and insecticides
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
EP0532022A1 (en) 1991-09-13 1993-03-17 Ube Industries, Ltd. Acrylate compound, preparation process thereof and fungicide using the same
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
WO1994001546A1 (en) 1992-07-01 1994-01-20 Cornell Research Foundation, Inc. Elicitor of the hypersensitive response in plants
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
DE19650197A1 (en) 1996-12-04 1998-06-10 Bayer Ag 3-thiocarbamoylpyrazole derivatives
WO1998046608A1 (en) 1997-04-14 1998-10-22 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
WO1999014187A1 (en) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Benzamidoxim derivatives, intermediate products and methods for preparing and using them as fungicides
WO1999024413A2 (en) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Isothiazole carboxylic acid amides and the application thereof in order to protect plants
WO1999027783A1 (en) 1997-12-04 1999-06-10 Dow Agrosciences Llc Fungicidal compositions and methods, and compounds and methods for the preparation thereof
WO2000029404A1 (en) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultura/horticultural bactericides
WO2000046148A1 (en) 1999-02-02 2000-08-10 Sintokogio, Ltd. Silica gel carrying titanium oxide photocatalyst in high concentration and method for preparation thereof
EP1028125A1 (en) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptide compounds having fungicidal activity and their agronomic use
EP1035122A1 (en) 1999-03-11 2000-09-13 Rohm And Haas Company Heterocyclic subsituted isoxazolidines and their use as fungicides
WO2000065913A1 (en) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Sulfonamide derivatives
DE10021412A1 (en) 1999-12-13 2001-06-21 Bayer Ag Fungicidal active ingredient combinations
WO2001054501A2 (en) 2000-01-25 2001-08-02 Syngenta Participations Ag Herbicidal composition
EP1122244A1 (en) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Uracil compounds and their use
WO2001056358A2 (en) 2000-01-28 2001-08-09 Rohm And Haas Company Enhanced propertied pesticides
CN1309897A (en) 2000-02-24 2001-08-29 沈阳化工研究院 Unsaturated oximino ether bactericide
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2002022583A2 (en) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl amides and imides for use as fungicides
EP1201648A1 (en) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Carbamate derivatives and agricultural/horticultural bactericides
WO2002040431A2 (en) 2000-11-17 2002-05-23 Dow Agrosciences Llc Compounds having fungicidal activity and processes to make and use same
JP2002316902A (en) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd Plant blight-preventing agent composition
WO2003010149A1 (en) 2001-07-25 2003-02-06 Bayer Cropscience Ag Pyrazolylcarboxanilides as fungicides
WO2003011853A1 (en) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates and their use as herbicides
WO2003014103A1 (en) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Iodobenzopyran-4-one derivatives having fungicidal activity
WO2003016303A1 (en) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient
WO2003016286A1 (en) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2003053145A1 (en) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Bactericidal composition
WO2003061388A1 (en) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Fused heterocyclic sulfonylurea compound, herbicide containing the same, and method of controlling weed with the same
WO2003064572A1 (en) 2002-01-31 2003-08-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with improved friction properties
WO2003066609A1 (en) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Disubstituted thiazolyl carboxanilides and their use as microbicides
WO2003074491A1 (en) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyl-carboxanilides and their use as fungicides
CN1456054A (en) 2003-03-25 2003-11-19 浙江省化工研究院 Methoxy methyl acrylate compounds as bactericidal agent
WO2004013094A2 (en) 2002-08-02 2004-02-12 Massachusetts Institute Of Technology Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
WO2004039783A1 (en) * 2002-10-21 2004-05-13 Sankyo Agro Company, Limited Quinoline-3-carboxamide compound
WO2004049804A2 (en) 2002-11-29 2004-06-17 Syngenta Participations Ag Fungicidal combinations for crop potection
WO2004083193A1 (en) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Amide compound and bactericide composition containing the same
WO2005063721A1 (en) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Herbicidal pyrimidines
WO2005070917A1 (en) 2004-01-23 2005-08-04 Sankyo Agro Company, Limited 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines
WO2005087772A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005087773A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005120234A2 (en) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Fungicidal mixtures of amidinylphenyl compounds
WO2005123690A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide
WO2005123689A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl)-anilides and to use thereof as fungicide
WO2006015866A1 (en) 2004-08-12 2006-02-16 Syngenta Participations Ag Method for protecting useful plants or plant propagation material
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
WO2006087325A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said substances
DE102005009458A1 (en) 2005-03-02 2006-09-07 Bayer Cropscience Ag pyrazolylcarboxanilides
WO2007006670A1 (en) 2005-07-07 2007-01-18 Basf Aktiengesellschaft N-thio-anthranilamid compounds and their use as pesticides
CN1907024A (en) 2005-08-03 2007-02-07 浙江化工科技集团有限公司 Methoxyl group displacement methyl acrylate compound bactericidal agent
WO2007082098A2 (en) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2007090624A2 (en) 2006-02-09 2007-08-16 Syngenta Participations Ag A method of protecting a plant propagation material, a plant, and/or plant organs
WO2007129454A1 (en) 2006-05-08 2007-11-15 Kumiai Chemical Industry Co., Ltd. 1,2-benzisothiazole derivative, and agricultural or horticultural plant disease-controlling agent
WO2008013622A2 (en) 2006-07-27 2008-01-31 E. I. Du Pont De Nemours And Company Fungicidal azocyclic amides
WO2008143263A1 (en) 2007-05-22 2008-11-27 Astellas Pharma Inc. 1-substituted tetrahydroisoquinoline compound
WO2009090181A2 (en) 2008-01-15 2009-07-23 Bayer Cropscience Sa Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance
WO2009094442A2 (en) 2008-01-22 2009-07-30 Dow Agrosciences Llc 5-fluoro pyrimidine derivatives
WO2010069882A1 (en) 2008-12-17 2010-06-24 Syngenta Participations Ag Isoxazole derivatives for use as fungicides
EP2223919A1 (en) * 2007-12-26 2010-09-01 Nippon Soda Co., Ltd. Nitrogen-containing heterocyclic compound and bactericide for agricultural and horticultural use
WO2010139271A1 (en) 2009-06-05 2010-12-09 中国中化股份有限公司 E-type phenyl acrylic ester compounds containing substituted anilino pyrimidine group and uses thereof
WO2011028657A1 (en) 2009-09-01 2011-03-10 Dow Agrosciences Llc Synergistic fungicidal compositions containing a 5-fluoropyrimidine derivative for fungal control in cereals
WO2011038204A1 (en) 2009-09-25 2011-03-31 N30 Pharmaceuticals, Llc Novel dihydropyrimidin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors
WO2011042918A2 (en) 2009-10-07 2011-04-14 Msn Laboratories Limited Novel and improved processes for the preparation of prasugrel, its intermediates and pharmaceutically acceptable salts
WO2011077514A1 (en) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Plant disease control composition and method for controlling plant diseases by applying the composition
WO2011081174A1 (en) 2010-01-04 2011-07-07 日本曹達株式会社 Nitrogen-containing heterocyclic compound and agricultural/horticultural germicide
JP2011148714A (en) * 2010-01-19 2011-08-04 Nippon Soda Co Ltd Disease controlling method
WO2011135833A1 (en) 2010-04-28 2011-11-03 Sumitomo Chemical Company, Limited Plant disease control composition and its use
WO2012051036A1 (en) 2010-10-11 2012-04-19 Merck Sharp & Dohme Corp. Quinazolinone-type compounds as crth2 antagonists
WO2012084812A1 (en) 2010-12-20 2012-06-28 Isagro Ricerca S.R.L. Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
WO2012165511A1 (en) 2011-05-31 2012-12-06 クミアイ化学工業株式会社 Method for controlling diseases in rice plant
WO2012168188A1 (en) 2011-06-07 2012-12-13 Bayer Intellectual Property Gmbh Active compound combinations
WO2013007767A1 (en) 2011-07-13 2013-01-17 Basf Se Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
WO2013010862A1 (en) 2011-07-15 2013-01-24 Basf Se Fungicidal alkyl-substituted 2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
WO2013024009A1 (en) 2011-08-12 2013-02-21 Basf Se N-thio-anthranilamide compounds and their use as pesticides
WO2013024010A1 (en) 2011-08-12 2013-02-21 Basf Se N-thio-anthranilamide compounds and their use as pesticides
WO2013047749A1 (en) 2011-09-29 2013-04-04 三井化学アグロ株式会社 Production method for 4, 4-difluoro-3,4-dihydroisoquinoline derivative
WO2013047441A1 (en) 2011-09-26 2013-04-04 日本曹達株式会社 Agricultural and horticultural bactericide composition
WO2013092224A1 (en) 2011-12-21 2013-06-27 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi resistant to qo inhibitors
WO2013116251A2 (en) 2012-02-01 2013-08-08 E. I. Du Pont De Nemours And Company Fungicidal pyrazole mixtures
WO2013127704A1 (en) 2012-02-27 2013-09-06 Bayer Intellectual Property Gmbh Active compound combinations containing a thiazoylisoxazoline and a fungicide
WO2013162072A1 (en) 2012-04-27 2013-10-31 Sumitomo Chemical Company, Limited Tetrazolinone compounds and its use as pesticides
CN103387541A (en) 2012-05-10 2013-11-13 中国中化股份有限公司 Preparation method of substituted pyrazolylether compound
US20130324506A1 (en) 2012-06-05 2013-12-05 Bioprojet New 6,11-dihydro-5H-benzo[d]imidazo[1,2-a]azepines derivatives as histamine H4 receptor ligands
WO2014060177A1 (en) 2012-10-16 2014-04-24 Syngenta Participations Ag Fungicidal compositions
EP2865265A1 (en) 2014-02-13 2015-04-29 Bayer CropScience AG Active compound combinations comprising phenylamidine compounds and biological control agents
WO2015065922A1 (en) 2013-10-28 2015-05-07 Dexcom, Inc. Devices used in connection with continuous analyte monitoring that provide the user with one or more notifications, and related methods
WO2015141867A1 (en) * 2014-03-20 2015-09-24 Mitsui Chemicals Agro, Inc. Plant disease control composition and method for controlling plant disease by application of same

Patent Citations (107)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
WO1983003968A1 (en) 1982-05-18 1983-11-24 University Of Florida Brain-specific drug delivery
EP0141317A2 (en) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them
EP0152031A2 (en) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Azolyl cycloalkanol derivatives and agricultural fungicides
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
EP0226917A1 (en) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Acrylic acid esters and fungicides containing these compounds
EP0243970A1 (en) 1986-05-02 1987-11-04 Stauffer Chemical Company Fungicidal pyridyl imidates
EP0256503A2 (en) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Pyridinecarboxamide derivatives and their use as fungicide
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en) 1989-03-24 1990-10-17 Ciba-Geigy Ag Disease-resistant transgenic plants
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
EP0428941A1 (en) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Hexahydrotriazine compounds and insecticides
EP0532022A1 (en) 1991-09-13 1993-03-17 Ube Industries, Ltd. Acrylate compound, preparation process thereof and fungicide using the same
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
WO1994001546A1 (en) 1992-07-01 1994-01-20 Cornell Research Foundation, Inc. Elicitor of the hypersensitive response in plants
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
DE19650197A1 (en) 1996-12-04 1998-06-10 Bayer Ag 3-thiocarbamoylpyrazole derivatives
WO1998046608A1 (en) 1997-04-14 1998-10-22 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
WO1999014187A1 (en) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Benzamidoxim derivatives, intermediate products and methods for preparing and using them as fungicides
WO1999024413A2 (en) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Isothiazole carboxylic acid amides and the application thereof in order to protect plants
WO1999027783A1 (en) 1997-12-04 1999-06-10 Dow Agrosciences Llc Fungicidal compositions and methods, and compounds and methods for the preparation thereof
WO2000029404A1 (en) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultura/horticultural bactericides
EP1028125A1 (en) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptide compounds having fungicidal activity and their agronomic use
WO2000046148A1 (en) 1999-02-02 2000-08-10 Sintokogio, Ltd. Silica gel carrying titanium oxide photocatalyst in high concentration and method for preparation thereof
EP1035122A1 (en) 1999-03-11 2000-09-13 Rohm And Haas Company Heterocyclic subsituted isoxazolidines and their use as fungicides
WO2000065913A1 (en) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Sulfonamide derivatives
EP1201648A1 (en) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Carbamate derivatives and agricultural/horticultural bactericides
DE10021412A1 (en) 1999-12-13 2001-06-21 Bayer Ag Fungicidal active ingredient combinations
WO2001054501A2 (en) 2000-01-25 2001-08-02 Syngenta Participations Ag Herbicidal composition
WO2001056358A2 (en) 2000-01-28 2001-08-09 Rohm And Haas Company Enhanced propertied pesticides
EP1122244A1 (en) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Uracil compounds and their use
CN1309897A (en) 2000-02-24 2001-08-29 沈阳化工研究院 Unsaturated oximino ether bactericide
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2002022583A2 (en) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl amides and imides for use as fungicides
WO2002040431A2 (en) 2000-11-17 2002-05-23 Dow Agrosciences Llc Compounds having fungicidal activity and processes to make and use same
JP2002316902A (en) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd Plant blight-preventing agent composition
WO2003010149A1 (en) 2001-07-25 2003-02-06 Bayer Cropscience Ag Pyrazolylcarboxanilides as fungicides
WO2003011853A1 (en) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates and their use as herbicides
WO2003014103A1 (en) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Iodobenzopyran-4-one derivatives having fungicidal activity
WO2003016286A1 (en) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
WO2003016303A1 (en) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2003053145A1 (en) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Bactericidal composition
WO2003061388A1 (en) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Fused heterocyclic sulfonylurea compound, herbicide containing the same, and method of controlling weed with the same
WO2003064572A1 (en) 2002-01-31 2003-08-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with improved friction properties
WO2003066609A1 (en) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Disubstituted thiazolyl carboxanilides and their use as microbicides
WO2003074491A1 (en) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyl-carboxanilides and their use as fungicides
WO2004013094A2 (en) 2002-08-02 2004-02-12 Massachusetts Institute Of Technology Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
WO2004039783A1 (en) * 2002-10-21 2004-05-13 Sankyo Agro Company, Limited Quinoline-3-carboxamide compound
WO2004049804A2 (en) 2002-11-29 2004-06-17 Syngenta Participations Ag Fungicidal combinations for crop potection
WO2004083193A1 (en) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Amide compound and bactericide composition containing the same
CN1456054A (en) 2003-03-25 2003-11-19 浙江省化工研究院 Methoxy methyl acrylate compounds as bactericidal agent
WO2005063721A1 (en) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Herbicidal pyrimidines
WO2005070917A1 (en) 2004-01-23 2005-08-04 Sankyo Agro Company, Limited 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines
US20080275242A1 (en) 2004-01-23 2008-11-06 Hiroyuki Ito 3-(Dihydro(Tetrahydro)Isoquinolin-1-Yl)Quinoline Compound
US7632783B2 (en) 2004-01-23 2009-12-15 Mitsui Chemicals Agro, Inc. 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinoline compound
EP1736471A1 (en) * 2004-01-23 2006-12-27 Sankyo Agro Company, Limited 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines
WO2005087772A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005087773A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005120234A2 (en) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Fungicidal mixtures of amidinylphenyl compounds
WO2005123689A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl)-anilides and to use thereof as fungicide
WO2005123690A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide
WO2006015866A1 (en) 2004-08-12 2006-02-16 Syngenta Participations Ag Method for protecting useful plants or plant propagation material
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
WO2006087325A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said substances
DE102005009458A1 (en) 2005-03-02 2006-09-07 Bayer Cropscience Ag pyrazolylcarboxanilides
WO2007006670A1 (en) 2005-07-07 2007-01-18 Basf Aktiengesellschaft N-thio-anthranilamid compounds and their use as pesticides
CN1907024A (en) 2005-08-03 2007-02-07 浙江化工科技集团有限公司 Methoxyl group displacement methyl acrylate compound bactericidal agent
WO2007082098A2 (en) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2007090624A2 (en) 2006-02-09 2007-08-16 Syngenta Participations Ag A method of protecting a plant propagation material, a plant, and/or plant organs
WO2007129454A1 (en) 2006-05-08 2007-11-15 Kumiai Chemical Industry Co., Ltd. 1,2-benzisothiazole derivative, and agricultural or horticultural plant disease-controlling agent
WO2008013622A2 (en) 2006-07-27 2008-01-31 E. I. Du Pont De Nemours And Company Fungicidal azocyclic amides
WO2008143263A1 (en) 2007-05-22 2008-11-27 Astellas Pharma Inc. 1-substituted tetrahydroisoquinoline compound
EP2223919A1 (en) * 2007-12-26 2010-09-01 Nippon Soda Co., Ltd. Nitrogen-containing heterocyclic compound and bactericide for agricultural and horticultural use
WO2009090181A2 (en) 2008-01-15 2009-07-23 Bayer Cropscience Sa Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance
WO2009094442A2 (en) 2008-01-22 2009-07-30 Dow Agrosciences Llc 5-fluoro pyrimidine derivatives
WO2010069882A1 (en) 2008-12-17 2010-06-24 Syngenta Participations Ag Isoxazole derivatives for use as fungicides
WO2010139271A1 (en) 2009-06-05 2010-12-09 中国中化股份有限公司 E-type phenyl acrylic ester compounds containing substituted anilino pyrimidine group and uses thereof
WO2011028657A1 (en) 2009-09-01 2011-03-10 Dow Agrosciences Llc Synergistic fungicidal compositions containing a 5-fluoropyrimidine derivative for fungal control in cereals
WO2011038204A1 (en) 2009-09-25 2011-03-31 N30 Pharmaceuticals, Llc Novel dihydropyrimidin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors
WO2011042918A2 (en) 2009-10-07 2011-04-14 Msn Laboratories Limited Novel and improved processes for the preparation of prasugrel, its intermediates and pharmaceutically acceptable salts
WO2011077514A1 (en) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Plant disease control composition and method for controlling plant diseases by applying the composition
WO2011081174A1 (en) 2010-01-04 2011-07-07 日本曹達株式会社 Nitrogen-containing heterocyclic compound and agricultural/horticultural germicide
JP2011148714A (en) * 2010-01-19 2011-08-04 Nippon Soda Co Ltd Disease controlling method
WO2011135833A1 (en) 2010-04-28 2011-11-03 Sumitomo Chemical Company, Limited Plant disease control composition and its use
WO2012051036A1 (en) 2010-10-11 2012-04-19 Merck Sharp & Dohme Corp. Quinazolinone-type compounds as crth2 antagonists
WO2012084812A1 (en) 2010-12-20 2012-06-28 Isagro Ricerca S.R.L. Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
WO2012165511A1 (en) 2011-05-31 2012-12-06 クミアイ化学工業株式会社 Method for controlling diseases in rice plant
WO2012168188A1 (en) 2011-06-07 2012-12-13 Bayer Intellectual Property Gmbh Active compound combinations
WO2013007767A1 (en) 2011-07-13 2013-01-17 Basf Se Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
WO2013010862A1 (en) 2011-07-15 2013-01-24 Basf Se Fungicidal alkyl-substituted 2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
WO2013024009A1 (en) 2011-08-12 2013-02-21 Basf Se N-thio-anthranilamide compounds and their use as pesticides
WO2013024010A1 (en) 2011-08-12 2013-02-21 Basf Se N-thio-anthranilamide compounds and their use as pesticides
WO2013047441A1 (en) 2011-09-26 2013-04-04 日本曹達株式会社 Agricultural and horticultural bactericide composition
WO2013047749A1 (en) 2011-09-29 2013-04-04 三井化学アグロ株式会社 Production method for 4, 4-difluoro-3,4-dihydroisoquinoline derivative
WO2013092224A1 (en) 2011-12-21 2013-06-27 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi resistant to qo inhibitors
WO2013116251A2 (en) 2012-02-01 2013-08-08 E. I. Du Pont De Nemours And Company Fungicidal pyrazole mixtures
WO2013127704A1 (en) 2012-02-27 2013-09-06 Bayer Intellectual Property Gmbh Active compound combinations containing a thiazoylisoxazoline and a fungicide
WO2013162072A1 (en) 2012-04-27 2013-10-31 Sumitomo Chemical Company, Limited Tetrazolinone compounds and its use as pesticides
CN103387541A (en) 2012-05-10 2013-11-13 中国中化股份有限公司 Preparation method of substituted pyrazolylether compound
US20130324506A1 (en) 2012-06-05 2013-12-05 Bioprojet New 6,11-dihydro-5H-benzo[d]imidazo[1,2-a]azepines derivatives as histamine H4 receptor ligands
WO2014060177A1 (en) 2012-10-16 2014-04-24 Syngenta Participations Ag Fungicidal compositions
WO2015065922A1 (en) 2013-10-28 2015-05-07 Dexcom, Inc. Devices used in connection with continuous analyte monitoring that provide the user with one or more notifications, and related methods
EP2865265A1 (en) 2014-02-13 2015-04-29 Bayer CropScience AG Active compound combinations comprising phenylamidine compounds and biological control agents
WO2015141867A1 (en) * 2014-03-20 2015-09-24 Mitsui Chemicals Agro, Inc. Plant disease control composition and method for controlling plant disease by application of same

Non-Patent Citations (33)

* Cited by examiner, † Cited by third party
Title
""Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed.", May 2008, CROPLIFE INTERNATIONAL
ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 52, no. 38, 2013, pages 10035 - 10039
ANTHONY J DE LUCCA: "Harmful fungi in both agriculture and medicine", REVISTA IBEROAMERICANA DE MICOLOGÍA, vol. 24, no. 1, 1 March 2007 (2007-03-01), Spain, pages 3 - 13, XP055211510, ISSN: 1130-1406 *
AUSTRAL. J. AGRICULT. RES., vol. 58, 2007, pages 708
BIOORGANIC & MEDICINAL CHEMISTRY, vol. 18, 2010, pages 3088 - 3115
CAN. J. PLANT SCI., vol. 48, no. 6, 1968, pages 587 - 94
CHEMICAL COMMUNICATIONS, vol. 49, no. 60, 2013, pages 6767 - 6769
CHEMMEDCHEM, vol. 7, no. 12, 2012, pages 2101 - 2112
DATABASE WPI Week 201154, Derwent World Patents Index; AN 2011-J81836, XP002764346 *
EDUARDO SOBARZO-SÁNCHEZ ET AL: "Synthesis of Anabaseine and Anabasine Derivatives: Structural Modifications of Possible Nicotinic Agonists", SYNTHETIC COMMUNICATIONS, vol. 37, no. 8, 1 April 2007 (2007-04-01), PHILADELPHIA, PA; US, pages 1331 - 1338, XP055320428, ISSN: 0039-7911, DOI: 10.1080/00397910701227168 *
J. AM. CHEM. SOC., vol. 123, no. 25, 2001, pages 5962 - 5973
J. HETEROCYC. CHEM., vol. 18, no. 7, 1981, pages 1305 - 8
J. MED. CHEM., vol. 38, no. 11, 1995, pages 1892 - 903
JOURNAL OF ORGANIC CHEMISTRY, vol. 76, no. 1, 2011, pages 164 - 169
JOURNAL OF ORGANIC CHEMISTRY, vol. 76, no. 2, 2011, pages 665 - 668
KNOWLES: "Agrow Reports DS243", 2005, T&F INFORMA, article "New developments in crop protection product formulation"
KNOWLES: "Agrow Reports DS256", 2006, T&F INFORMA, article "Adjuvants and additives"
MCCUTCHEON'S: "Emulsifiers & Detergents", vol. 1, 2008, MCCUTCHEON'S DIRECTORIES
MOLLET; GRUBE-MANN: "Formulation technology", 2001, WILEY VCH
PEST MANAGEM. SCI., vol. 61, 2005, pages 246
PEST MANAGEM. SCI., vol. 61, 2005, pages 258
PEST MANAGEM. SCI., vol. 61, 2005, pages 269
PEST MANAGEM. SCI., vol. 61, 2005, pages 277
PEST MANAGEM. SCI., vol. 61, 2005, pages 286
PEST MANAGEM. SCI., vol. 64, 2008, pages 326
PEST MANAGEM. SCI., vol. 64, 2008, pages 332
SCIENCE, vol. 316, 2007, pages 1185
SYNLETT., vol. 4, 2007, pages 652 - 654
SYNTHETIC COMMUNICATIONS, vol. 37, 2007, pages 1331 - 1338
TETRAHEDRON, vol. 68, 2012, pages 2696 - 2703
TETRAHEDRON, vol. 68, no. 9, 2012, pages 2113 - 2120
TETRAHEDRON: ASYMMETRY, vol. 17, no. 4, 2006, pages 508 - 511
WEED SCI., vol. 57, 2009, pages 108

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11425910B2 (en) 2017-02-21 2022-08-30 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2019115343A1 (en) * 2017-12-15 2019-06-20 Basf Se Fungicidal mixture comprising substituted pyridines
US11839214B2 (en) 2017-12-15 2023-12-12 Basf Se Fungicidal mixture comprising substituted pyridines
WO2022073932A1 (en) * 2020-10-05 2022-04-14 Syngenta Crop Protection Ag Fungicidal compositions
US11820747B2 (en) 2021-11-02 2023-11-21 Flare Therapeutics Inc. PPARG inverse agonists and uses thereof

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