WO2018054721A1 - Pyridine compounds for controlling phytopathogenic harmful fungi - Google Patents

Pyridine compounds for controlling phytopathogenic harmful fungi Download PDF

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WO2018054721A1
WO2018054721A1 PCT/EP2017/072884 EP2017072884W WO2018054721A1 WO 2018054721 A1 WO2018054721 A1 WO 2018054721A1 EP 2017072884 W EP2017072884 W EP 2017072884W WO 2018054721 A1 WO2018054721 A1 WO 2018054721A1
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alkyl
formula
halogen
alkoxy
compounds
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PCT/EP2017/072884
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French (fr)
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Bernd Mueller
Erica CAMBEIS
Jan Klaas Lohmann
Ana Escribano Cuesta
Antje Wolf
Marcus Fehr
Nadine RIEDIGER
Violeta TERTERYAN-SEISER
Wassilios Grammenos
Christian Winter
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Basf Se
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    • 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
    • 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—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.
  • 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-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, 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 hal ogen, 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 1 which independently of one another are selected from:
  • R 1 b 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 the substituents as defined for R 1 , wherein the possible substituents for R 2 are R 2a and R 2 , respectively, which correspond to R 1a and R 1 b , respectively;
  • 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 b halogen, OH , CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , N
  • 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-C4-alkyl, Ci-C4-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-C4-al- kyl, halogen, Ci-C 4 -halogenalkyl, Ci-C4-alkoxy and Ci-C4-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 carries one, two
  • R 5 is H ;
  • R 6 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 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 78 which independently of one another are selected from: R 78b halogen, OH , CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, d-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl,
  • R x is as defined above;
  • R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C 2 -C 6 -halogenalkynyl, C 3 -C 6 -cycloalkyl, and C 3 -C 6 -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, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C 3 -Ce-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;
  • R 9b which independently of one another are selected from: 9b 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 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, N H2, NH(Ci-C4- alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-Ce-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;
  • heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N,
  • 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, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, Ci-C 4 -alkylthio;
  • R 11b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, CrC 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthioand 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).
  • an acid in an organic solvent
  • sulfuric acid or a sulfonic acid, in particular triflic acid are used as acid.
  • suitable solvents are hydrocarbons, preferably benzene or dichloromethane.
  • 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 III 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 II can be prepared as described below, A skilled person will realize that compounds of type lllb can be reacted with organometaiiic 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.
  • organometaiiic reagents preferably alkyl Grignard or al- kyl-Lithium reagents
  • alcohols of type II can be prepared from epoxydes Ilia and compounds VI (see be- low):
  • 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 lllb can be achieved by reacting compounds of type IV with organometallic reagents, preferably alky! 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 alky! 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(C 2 H 5 ) 3 or pyridine (see e.g. US 20130324506; Tetrahedron: Asymmetry, 17(4), 508-511 ; 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).
  • aryl halides will react with compounds of type VII in the presence of a transition metal catalyst, preferably a copper ⁇ ) salt, in an organic solvent, preferably DMF or DMSO, at elevated temperatures.
  • a transition metal catalyst preferably a copper ⁇
  • organic solvent preferably DMF or DMSO
  • a base preferably potassium phos hate, 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 re- action 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.
  • the intramo- lecular 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
  • SnCI 4 or BF 3 are used as dehydrating agent.
  • suitable solvents are hydrocarbons, preferably benzene, toluene or acetonitrile.
  • 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. As described 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.
  • or- ganometallic agents preferably Grignard or Lithium reagent
  • 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 compounds of formula X have fungicidal activity and the details below referring to the compounds I also apply to compounds X.
  • Particular embodiments of the intermediate X are the following compounds X.A, X.B, X.C, X.D.
  • the substituents R 4 , R 78 , o, R 9 , R 10 are independently as defined in claim 1 or
  • 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-dimethylbutyl
  • 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).
  • Ci-C6-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
  • CrC 6 -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.
  • 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-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-Ce-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 OCH 2 F, OCHF 2 , OCF 3 , OCH2CI, OCHCI2, OCC , 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-flu
  • 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,
  • 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 “C 2 -C 4 -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-Cs-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).
  • CrC6-alkylthio refers to straight-chain or branched alkyl groups hav- ing 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 having 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,
  • 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-
  • 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
  • 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.
  • 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 in- vention.
  • 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-C 4 -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-halocycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 1a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, C 1 -C 4 - halogenalkyl, Ci-C 4 -alkoxy and CrC 4 -halogenalkoxy;
  • R 1 wherein the carbocyclic, heteroaryl and aryl moieties of R 1 are unsubstituted or substituted with identical or different groups
  • R 1 b which independently of one another are selected from: R 1b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halocycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
  • 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 OH
  • R 1 is CN
  • R 1 is NH2, NH(Ci-C 4 -alkyl), N(Ci-C4-alkyl)2 or NH-S02-R X , wherein R x is Ci-C 4 -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-C 4 -alkyl.
  • R 1 is CrC 6 -alkyl, in particular Ci-C 4 -alkyl,
  • R 1 is Ci-C6-halogenalkyl, in particular C 1 -C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI 2 or CH 2 CI.
  • 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-ECH.
  • R 1 is Ci-C6-alkoxy, in particular CrC 4 -alkoxy, more specifically Ci-C2-alkoxy such as OCH 3 or OCH2CH3.
  • R 1 is Ci-C6-halogenalkoxy, in particular Cr C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCIs, OCHCI2 or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 1 is C 3 -C6-cycloalkyl, in particular cyclopro- pyl.
  • R 1 is C 3 -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 C 3 -C6-halocycloalkyl.
  • 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 , N H-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 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 1 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-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-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-halocycloalkyl, Ci-C4-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-C4-alkyl, Ci-C4-halogenalkyl, Ci-C 4 -alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C 2 -alkyl, Ci-C 2 -halogenalkyl, Ci-C 2 - alkoxy and Ci-C2-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, C3- C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C2-halogenalkoxy.
  • R 1a is independently selected from F, CI, OH, CN , Ci-C 2 -alkoxy, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and Ci-C2-halogenalkoxy.
  • 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-halocycloalkyl and Ci-C2-halogenalkoxy. Specifically, R 1a is independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
  • R 1b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R 1 .
  • R 1 according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C 4 -halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C4-halogenalkoxy.
  • R 1b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalky and Ci-C2-halo- genalkoxy.
  • R 1 is independently selected from F, CI, OH, CN, CH 3 , OCH 3 , cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and halogenmethoxy.
  • R 1b is independently selected from halogen, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C2-hal- ogenalkoxy.
  • R 1 is independently selected from halogen, OH, CH 3 , OCH 3 , cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH 3 , OCH 3 , cyclopropyl, 1-F-cyclopropyl, 1-CI- 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-C 4 -alkoxy and Ci-C 4 -halogenalkoxy.
  • R x is in each case independently selected from Ci-C 4 -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 invention. Thereby, for every R 1 that is present in the inventive compounds, these specific
  • Ts in the table stands for the tosylgroup S0 2 -(p-CH 3 )phenyl.
  • 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-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, CrC 6 -alkoxy, C 3 -C 6 -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 x2 independently selected from Ci-C 4 -alkyl, halogen, OH,
  • Ci-C 4 -halogenalkyl Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
  • R 2a which independently of one another are selected from: R 2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalky, Ci-C4-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-C4-alkyl, C1-C4- halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
  • R 2 wherein the carbocyclic, heteroaryl and aryl moieties of R 2 are unsubstituted or substituted with identical or different groups R 2 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 - halocycloalky, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
  • R 2 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 2 is halogen, in particular Br, F or CI, more specifically F or CI.
  • R 2 is hydrogen
  • R 2 is OH
  • R 2 is CN
  • 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-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R x2 independently selected from Ci-C4-alkyl.
  • R 2 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH 3 or CH 2 CH 3 .
  • R 2 is CrC6-halogenalkyl, in particular C 1 -C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI 2 or CH 2 CI.
  • R 2 is C 2 -C6-alkynyl or C 2 -C6-halogenalkynyl, in particular C 2 -C4-alkynyl or C 2 -C4-halogenalkynyl, such as C-ECH.
  • R 2 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 2 is CrC6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically CrC 2 -halogenalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCI3, OCHCI 2 or OCH 2 CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
  • R 2 is C 3 -C6-cycloalkyl, in particular cyclopropyl.
  • R 2 is C 3 -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 defined and preferably herein.
  • R 2 is C3-C6-halocycloalky.
  • 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(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 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 2 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-C 4 -alkyl, Ci-C4-halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy.
  • R 2a are the possible substituents for the acyclic moieties of R 2 .
  • R 2a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalky, 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, CrC 4 -alkyl, Ci-C 4 -halogenalkyl, CrC 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 2a is independently selected from halogen, OH, CN, Ci-C 2 - alkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalky and Ci-C 2 -halogenalkoxy.
  • R 2a is independently selected from F, CI, OH, CN, Ci-C 2 -alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl and Ci-C 2 -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-halocycloalky and Ci-C 2 -halogenalkoxy. Specifically, R 2a is independently selected from OH, cyclopropyl and Ci-C 2 -halogenalkoxy.
  • R 2b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R 2 .
  • R 2 according to the invention is independently selected from halogen, OH, CN, Ci-C 4 -alkyl, Ci- C4-alkoxy, CrC 4 -halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalky and Ci-C4-halogenalkoxy.
  • R 2b is independently selected from halogen, CN, Ci-C 2 - alkyl, Ci-C 2 -alkoxy, CrC 2 -halogenalkyl, C3-C6-cycloalkyl, Cs-Ce-halocycloalkyl and Ci-C 2 -halo- genalkoxy.
  • R 2 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, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C2-hal- ogenalkoxy.
  • R 2b is independently selected from halogen, OH, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH 3 , OCH 3 , cyclopropyl, 1-F-cyclopropyl, 1-CI- cyclopropyl , OCH F2 and OCF3.
  • R 2 is in Table P2 below, wherein each line of lines P2-1 to P2-16 corresponds to one particular embodiment of the inven- tion. Thereby, for every R 2 that is present in the inventive compounds, these specific embodiments and preferences apply independently of the meaning of any other R 2 that may be present in the ring:
  • Ts in the table stands for the tosylgroup S0 2 -(p-CH 3 )phenyl.
  • R 3 is in each case independently selected from CH3, CH2F, CH F2 and CF3.
  • R 3 is CH3.
  • R 3 is CH2F.
  • R 3 is CHF 2 .
  • R 3 is CF 3 .
  • 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, N0 2 , SH, NH 2 , NH(Ci-C -alkyl), N(Ci-C 4 -alkyl) 2 ,
  • alkyl 2 , NH-S0 2 -R x , Ci-C 6 -alkylthio, Ci-C -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy, Ci-C 4 -halo- genalkoxy, and S(0)n-Ci-C6-alkyl; and wherein R x , R' and R" are as defined above;
  • 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:
  • R b halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 ,
  • 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 2 , halogenphenyl-CH 2 , phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted by substitu- ents 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 4 as defined below. According to one embodiment thereof, the carbo- and het- erocycle 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 4 as defined below.
  • R 4 is selected from C 2 -C6-alkenyl, C 2 -C6-halo- genalkenyl, C 2 -C6-alkynyl, C 2 -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 de- fined below.
  • R 4 is selected from CN, C 2 -C6-alkenyl, C 2 -C6- halogenalkenyl, C 2 -C6-alkynyl, C 2 -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 CrC6-alkylthio, such as SCH3, SC2H5, Sn-propyl, Si-propyl, Sn-butyl, Si-butyl, Stert-butyl, Sn-pentyl or Si-pentyl.
  • R 4 is Ci-C6-halogenalkylthio, such as SCF3, SCC .
  • 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:
  • R 4a halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 ,
  • N(C( 0)Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkylthio, Ci-C 4 -alkyl, Ci-C -halogenalkyl, C1-C4- 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 , Ci-C 6 -alkylthio, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, d-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: R 4a halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 ,
  • N(C( 0)Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C B -alkylthio, CrC 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 - alkoxy, Ci-C 4 -halogenalkoxy, and S(0)n-Ci-C6-alkyl.
  • R 4 is CN
  • R 4 is CH 2 CN.
  • R 4 is CH 2 OH.
  • R 4 is Ci-Ce-halogenalkyl, in particular C1-C4- halogenalkyl, more specifically Ci-C 2 -halogenalkyl, such as CF 3 , 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-ECH, C..C-CI, C ⁇ C-CH 3 , 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 Ci-C 4 - alkoxy, more specifically Ci-C 2 -alkoxy such as OCH 3 or OCH 2 CH 3 .
  • R 4 is Ci-C6-alkyl-Ci-C6-alkoxy, in particular Ci-C 4 -alkyl-Ci-C4-alkoxy, more specifically Ci-C 2 -alkyl-Ci-C 2 -alkoxy, such as
  • R 4 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH
  • R 4 is Ci-C6-halogenalkoxy, in particular CrC4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCI3, OCHCI2 or OCH2CI, in particular OCF 3 , OCHF2, OCCI 3 or OCHCI 2 .
  • R 4 is Ci-C6-alkyl-CrC6-halogenalkoxy, in particular Ci-C4-alkyl-Ci-C4-halogenalkoxy, more specifically Ci-C 2 -alkyl-CrC 2 -halogenalkoxy such as CH2OCF3, CH2OCHF2, CH2OCH2F, CH2OCCI3, CH2OCHCI2 or CH2OCH2CI, in particular CH2OCF3, CH 2 OCHF 2 , CH2OCCI3 or CH 2 OCHCI 2 .
  • 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.
  • R 4 is CR -NOR" such as
  • R 4 is Ci-C6-alkyl-NH(Ci-C4-alkyl) or Ci- C6-alkyl-N(Ci-C4-alkyl)2, wherein alkyl is CH 3 , C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
  • R 4 is Ci-C6-alkylthio, in particular C 1 -C4- alkoxy, more specifically Ci-C3-alkylthio such as CH2SCH3 or CH2SCH 2 CI-l3.
  • R 4 is Ci-C6-alkyl substituted by CN such as CH2CN
  • R 4 is Ci-C6-alkyl-S(0) n -Ci-C6-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.
  • 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-C2-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 , OCH3, CF 3 , CHF2, OCHF2, OCF3.
  • 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 selected from Ci-C6-alkyl which is sub- stituted, 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 selected from Ci-C6-alkyl which is substituted, a 3-mem- bered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4 . According to still another embodiment of formula I, it is substituted by R 4b .
  • R 4 is selected from Ci-C6-alkyl which is substituted, a 4-mem- bered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4 . According to still another embodiment of formula I, it is substituted by R 4b .
  • R 4 is selected from Ci-C6-alkyl which is substituted, a 5- membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4 . According to still another embodiment of formula I, it is substituted by R 4 .
  • R 4 is selected from Ci-C6-alkyl which is substituted, 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-alky ⁇ , especially Chb substituted by 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 .
  • 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 4 .
  • 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.
  • 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-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 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 4 .
  • 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 . According to one embodiment, 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 4 . 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-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 4 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 mem- bers.
  • 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 .
  • 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-C 2 -alkyl, C 1 -C 2 - alkoxy, Ci-C 2 -halogenalkyl, Ci-C 2 -halogenalkoxy and S(0) n -Ci-C6-alkyl, in particular from CN, F, CI, Br, CH3, OCH3, 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-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isoxa
  • 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 P4-128 corresponds to one particular embodiment of the invention, wherein P4-1 to P4-128 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 substit- uent selected from Ci-C4-alkyl, Ci-C4-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-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 SO 2 , and wherein the carbocycle or heterocycle is unsubstitute
  • R 3 and R 4 form a 3-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4 .
  • R 4 is substituted by R 4 .
  • R 3 and R 4 form a 4-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 5-membered saturated carbocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4 .
  • R 4 is substituted by R 4 .
  • 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 4 .
  • R 4 is substituted by R 4 .
  • 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 4 .
  • R 4 is substituted by R 4 .
  • 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 4 .
  • R 4 is substituted by R 4 .
  • R 3 and R 4 form a 7-membered saturated heterocycle.
  • the carbocycle is unsubstituted, i.e. it does not carry any substituent R 4 .
  • R 4 is substituted by R 4 .
  • Particularly preferred embodiments of combinations of R 3 and R 4 according to the invention are in Table P34 below, wherein each line of lines P34-1 to P34-534 corresponds to one particular embodiment of the invention, wherein P34-1 to P34-534 are also in any combination with one another a preferred embodiment of the present invention.
  • the carbon atom, to which R 3 and R 4 are bound is marked with * in the drawings. "Ts" in the drawings stands for the tosylgroup S02-(p-CH 3 )phenyl. Table P34
  • R 4a is in each case independently selected from halogen, OH, CN, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and heterocycle, wherein the heretocy- clocycle 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 substi- tuted by halogen selected from the group consisting of F, CI, Br, CH 3 , CHF 2 , OCH 3 , OCHF 3 , CN or S0 2 CH3.
  • 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 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, CrC 6 -alkoxy, Ci-C -halogenalkoxy, CrC 6 - 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-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy.
  • R 4a is in each case independently selected from halogen and phenyl wherein the phenyl is substituted by halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
  • R 4b are the possible substituents for the carbocycle, heterocycle, heteroaryl and aryl moieties and are independently selected from halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C -alkyl), N(Ci-C 4 - alkyl) 2 , NH-S0 2 -R x , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci- C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, Ci-C 4 -halogenalkoxy, Ci-C 6 -alkylthio, Ci-C6-halogenalkylthio, S(0) n -Ci-C6-alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubsti
  • R 4b is in each case independently selected from halogen, OH, CN, SH, Ci-C6-alkyl, Ci-CB-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C1-C6- alkylthio and S(0) n -Ci-C6-alkyl.
  • R 4b is in each case independently selected from halogen, Ci-C 5 -alkoxy, CrC 6 -halogenalkyl, Ci-C 6 -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 further 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 OCH3. According to one further particular embodiment, R 4 is in each case independently selected from Ci-C4-halogenalkoxy, such as OCHF2 and OCF3. According to one further particular embodiment, R 4b is in each case independently selected from S(0) n -Ci-C 6 -alkyl. such as SO2CH3.
  • R 5 is H.
  • R 6 is H.
  • R 78 are independently selected from halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl),
  • Ci-C6-halogenalkoxy C 2 -C6-alkenyloxy, C 2 -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
  • R 78a wherein the acyclic moieties of R 78 are unsubstituted or substituted by R 78a which independently of one another are selected from:
  • R 78a halogen, OH, CN, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C B -cycloalkenyl, C 3 -C 6 - halogencycloalkyl, C3-C6-halocycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, 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, C1-C4- alkoxy and Ci-C4-halogenalkoxy;
  • R 78 wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R 78 are unsubsti- tuted or substituted by R 78b which independently of one another are selected from:
  • R 78 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-C 6 -alkyl, Ci-C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 - 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 N0 2 .
  • R 78 is SH.
  • R 78 is NH 2 .
  • R 78 is , NH(Ci-C4-alkyl), in particular
  • R 78 is , N(CrC 4 -alkyl) 2 , in particular
  • R 78 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 or NH-S0 2 -Ts.
  • R 78 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH 3 . or C 2 H5, in particular CH 3 .
  • R 78 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 78 is C 2 -C6-alkynyl or C 2 -C6-halogen- alkynyl, in particular C 2 -C4-alkynyl or C 2 -C4-halogenalkynyl, such as C CH or CH 2 - C CH.
  • R 78 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH 3 or OCH2CH3.
  • R 78 is Ci-C6-halogenalkoxy, in particular CrC4-halogenalkoxy, more specifically Ci-C 2 -halogenalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCI3, OCHCI 2 or OCH2CI, in particular OCF 3 , OCHF2, 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
  • R 78 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
  • R 78 is C3-C6-halogencycloalkyl.
  • R 1 is fully or partially halogenated cyclopropyl.
  • R 78 is C3-C6-cycloalkenyl, in particular cyclo- propenyl.
  • R 78 is a 3-membered saturated carbocycle. 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 78b .
  • R 78 is a 4-membered saturated carbocycle. 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 .
  • R 78 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R78 . According to still another embodiment of formula I, it is substituted by R 78b .
  • R 78 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R78 b . According to still another embodiment of formula I, it is substituted by R 78 .
  • R 78 is a partially unsaturated 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 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-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 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 heteroatom.
  • the heterocycle is unsubstituted, i.e. it does not carry any substituent R 78b .
  • it is substituted by
  • 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 .
  • it is substituted by 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, Ci-C 2 -alkyl, Ci-C 2 -alkoxy, Ci-C 2 -halogenalkyl and Ci-C 2 -halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF 2 , 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 R 78b 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, CH 3 , CHF 2 , OCH 3 , 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 in each case independently selected from halogen, CN, Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Cs-alkoxy, 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 carbo- and het- erocycle 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 unsubstitute
  • R 78 is in each case independently selected from halogen, CN, Ci-C B -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C B -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 unsub
  • 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-Cs-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Cs-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 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-C 2 -alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl , 1 ,1-F2-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-C 4 -alkoxy.
  • R 78b is independently selected from F, CI, CN, CH 3 , OCH 3 and halogenmethoxy.
  • Particularly preferred embodiments of the phenyl ring, optionally substituted by (R 78 ) 0 , according to the invention are in Table P78 below, wherein each line of lines P78-1 to P78-40 corresponds to one particular embodiment of the invention, wherein P78-1 to P78-40 are also in any combi- nation 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:
  • R 9 is in each case independently selected from H, halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci- C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH(C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkenyl) 2 , NH(C 2 -C 4 -alkynyl), N(C 2 -C 4 -al- kynyl) 2 , NH(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 -alkynyl), N(C 2 -C -cycloalkyl)(C 3 -C 6 -cycl
  • heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
  • CrC 6 -alkyl is CrC 6 -alkyl, Ci-C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 alkynyl, C 2 -C6-halogenalkynyl, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl;
  • R 9a which independently of one another are selected from: R 9a halogen, OH, CN, Ci-Ce-alkoxy, Ca-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci- C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is un- substituted 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-halo- genalkoxy;
  • groups 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, C3-C6-halogencycloalkyl, Ci-C4-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, C3-C6-cycloalkyl, C3-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 N0 2 .
  • R 9 is SH.
  • R 9 is NH 2 .
  • R 9 is , NH(Ci-C 4 -alkyl), in particular NH(CH 3 NH(C 2 H 5 ).
  • R 9 is , N(Ci-C 4 -alkyl) 2 , in particular NH(CH 3 )
  • R 9 is , NH(C 2 -C4-alkynyl), in particular NH(C CH), NH(CH 2 C ⁇ CH).
  • R 9 is , N(C2-C4-alkynyl) 2 , in particular N(C CH) 2 , N(CH 2 C ⁇ CH) 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)(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 9 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 9 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 Hg), N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ).
  • R 9 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 9 is S(0)n-C 2 -C6-alkenyl such as
  • R 9 is Ci-Ce-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH 3 or CH2CH3.
  • R 9 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 , CCI3CH2 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.
  • R 9 is OR Y , wherein R Y is CrC6-alkyl, Cr C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3- Ce-cycloalkyl, C 3 -C 6 -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 OCH 3 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 , OCCI3 or OCHC .
  • 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 C 2 -C6-alkynyl, in particular C 2 -C6-alkynyl, in particular C 2 -C4-alkynyl, more specifically Ci-C 2 -alkynyl.
  • R 9 is such as OC ⁇ CH
  • 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-halocycloal- kyl.
  • 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 9 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 phenyl-Ci-C6-alkyl, such as phenyl-
  • R 9 which independently of one another are selected from halogen, Ci-C 2 -alkyl, Ci-C 2 -alkoxy, Ci-C 2 -halogenalkyl and Ci-C 2 -halogenalkoxy, in particular F, CI, Br,
  • 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 halogen, Ci-C 2 -alkyl, Ci-C 2 -alkoxy, Ci-C 2 -halogenalkyl and Ci-C 2 -halogenalkoxy, in particular F, CI, Br, CH3, OCH3, CF3 and OCF3.
  • 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-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 9 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, C 1 -C6- alkoxy, Ci-C 6 -halogenalkoxy, C 3 -C 3 -alkenyloxy, C 3 -C 6 -alkynyloxy and C 3 -C 6 -cycloalkyl 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 carbocyclic, 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, 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 9 are unsubstituted or substituted with identical or different groups R 9a as defined and preferably defined herein, and wherein the cycloalkyl moieties of R 9 are unsubstituted or substituted with identical or different groups R 9b as defined and preferably defined herein.
  • R 9a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyl, C3-C6-halocycloalkyl 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 cycloalkyl, 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, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-halogenalkoxy and Ci- C6-alkylthio.
  • R Sb 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 , CH 3 , OCH 3 and halogenmethoxy.
  • R s 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 in- vention, 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 , NH 2 , NH(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 3 -cycloalkyl), N(C 3 -C6-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 -alkynyl), N(C 2 -C -
  • 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, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-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 -halocycloalkyl, Ci-C 4 - halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted or substituted by substituents R 101a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
  • 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, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
  • R 10 is secected 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 and OR Y .
  • R 10 is H.
  • 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-C 4 -alkyl) 2 , in particular
  • R 10 is , NH(C 2 -C 4 -alkynyl), in particular NH(C ⁇ CH), NH(CH 2 C ⁇ CH).
  • R 10 is , N(C 2 -C 4 -alkynyl) 2 , in particular N(C ⁇ CH) 2 , N(CH 2 C ⁇ CH) 2 .
  • R 10 is , NH(C3-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-C 4 -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)(C3-C6-cycloalkyl), in particular N(CH 3 )(C 3 H 7 ), N(CH 3 )(C 4 H 9 ), N(C 2 H5)(C 3 H7), N(CH 3 )(C 4 H 9 ).
  • R 10 is N(C2-C4-alkynyl)(C3-C6-cycloalkyl), in particular N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H9), N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ).
  • R 10 is NH-S02-R X such as NH-SO2- CH 3 , NH-SO2-CH2-CH3, NH-SO2-CF3, NH-SO2-TS.
  • R 10 is S(0)n-C2-C6-alkenyl such as
  • R 10 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH 3 or CH2CH3.
  • 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 , CCI3CH2 or CF 2 CHF 2 .
  • R 10 is C2-C6-alkynyl or C2-C6-halogen- alkynyl, in particular C2-C 4 -alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2 C CH.
  • R 10 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, C 3 -C 6 -cycloalkyl, C 3 -C 6 -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 OCH 3 or OCH2CH3.
  • R 10 is OR Y , wherein R Y is Ci-C6-halo- genalkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C 2 -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-C 4 -alkenyl, more specifically CrC 2 -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
  • 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-halocycloal- kyl.
  • 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 -F 2 -cyclopropyl, 1 ,1-CI 2 -cyclopropyl
  • R 10 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 10b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br,
  • 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 halogen, Ci-C 2 -alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and CrC 2 -halogenalkoxy, in particular F, CI, Br, CH 3 , OCH 3 , 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, 69yrazine69-1 -yl, 69yrazine69-2-yl, 69yrazine69-4-yl, 69yra- zine69-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thia- zol-2-yl, thiazol-4-yl, thiazol-5-yl, iso
  • R 10 is a 6-membered heteroaryl such as 69yrazine-2-yl, 69yrazine-3-yl, 69yrazine-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, py- rimidin-4-yl, pyrimidin-5-yl, 69yrazine-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-C 6 -alkyl, Ci-C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 - alkoxy, Ci-C6-halogenalkoxy,C 3 -C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl wherein the acyclic moieties of 10 are unsubstituted or substituted with identical or different groups R 10a as defined and preferably defined herein, and wherein the carbocyclic, phenyl and heteroaryl moieties of R 10 are unsubstituted or substituted with identical or different groups R 10b as defined and preferably defined herein.
  • R 10 is in each case independently selected from H , halogen, CN , CrC 5 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, CrC 5 -alkoxy, C 3 -C 6 -alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl, 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 cycloalkyl moieties of R 10 are unsubstituted or substituted with identical or different groups R 10 as defined and preferably defined herein.
  • R 10a is independently selected from halogen, Ci-C6-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy.
  • R 10a is independently selected from 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 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, C 3 -C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-Ce-alkylthio.
  • R 10b is independently selected from halogen, CN , C1-C4- alkyl, Ci-C4-alkoxy, CrC4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C 4 -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 invention, 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 NR 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-haloalkyl and S02Ph, 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-haloalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl substituents.
  • R N is in each case independently selected from Ci-C 2 -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 11 it is substituted by 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 .
  • 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. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 11 . According to still another embodiment of formula I, it is substituted by R 11 . According to one embodiment, R 9 and R 10 form a 6-membered heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 11 . According to still another embodiment of formula I, it is substituted by R 11 .
  • R 11 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 -C 6 -alkynyl, CrC 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; wherein the heterocycle and 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 x11 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-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, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, Ci-C 4 -halogen- alkoxy, 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, C1-C4- halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C 3 -C6-halogencycloal- kyl, 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-C4-halogenalkoxy and Ci-C6-alkylthio.
  • R 11 is H, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-Ce-alkoxy or , Ci-C 6 -halogenalkoxy, in particular H, CH 3 , Et, CHF 2 , OCH 3 , OCHF 2 , OCF 3 , F, CI, more specifically H, CH 3 , F or CI most preferred H, F or CI.
  • R 11 is hydrogen
  • 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 NH 2 , NH(Ci-C4-alkyl), N(Ci-C 4 -alkyl) 2 or NH-S0 2 -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-C 4 -al- kyl.
  • R 11 is Ci-C6-alkyl, in particular Ci-C 4 -alkyl
  • R 11 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI 2 or CH 2 CI.
  • R 11 is C 2 -C6-alkynyl or C 2 -C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, Ch C CH.
  • R 11 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
  • R 11 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF 2 , OCH2F, OCCI 3 , OCHCI2 or OCH2CI, in particular OCF 3 , OCH F2, 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 11b , 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 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 , d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and Ca-Ce-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 11b as defined below.
  • R 11 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-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-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-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 and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy, Ci-C2-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-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy.
  • R 11a is independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F 2 -cyclopropyl, 1 ,1-Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
  • 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-C2-halogenalkoxy. Specifically, R 11a is independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
  • R 11b are the possible substituents for the carbocyclic, heterocyclic and heteroaryl moieties of
  • R 11b 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 11b 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 11 is independently selected from F, CI, OH, CN, CH 3 , OCH 3 , cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1-F 2 -cyclopropyl, 1 ,1-CI 2 -cyclopropyl and halogenmethoxy.
  • R 11b 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 is independently selected from OH, CH 3 , OCH 3 , 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- CI-, 1 ,1-F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl cyclopropyl and OCHF 2 .
  • Particular embodiments of the compounds I are the following compounds: I.A, I.B, I.C, I.D, I.E, I.F, I.G, I.I, I.J, I.K, I.L.
  • substituents R 4 , R 9 and R 10 are independently as defined in claim 1 or referably defined below:
  • Table 1-1 Compounds of the formula I.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.A.1 -1.A-1 to I.A.1-1.A-246).
  • Table 1-2 Compounds of the formula I.A in which R 9 is CHF2 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.A.1 -2.A-1 to I.A.1-2.A-246).
  • Table 1-3 Compounds of the formula I.A 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.A.1 -3.A-1 to I.A.1-3.A-246).
  • Table 1-4 Compounds of the formula I.A in which R s is Br and the meaning for the combina- tion of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.A.1 -4.A-1 to I.A.1-4.A-246).
  • Table 1-5 Compounds of the formula I.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.A.1 -5.A-1 to I.A.1-5.A-246).
  • Table 1-6 Compounds of the formula I.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 I.A.1-6.A-1 to I.A.1-6.A-246).
  • Table 2-1 Compounds of the formula I.B 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.B.2-1.A-1 to I.B.2-1.A-246).
  • Table 2-2 Compounds of the formula I.B in which R 9 is CHF2 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.B.2-2.A-1 to I.B.2-2.A-246).
  • Table 2-4 Compounds of the formula I.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 I.B.2-4.A-1 to I.B.2-4.A-246).
  • Table 2-5 Compounds of the formula I.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 I.B.2-5.A-1 to I.B.2-5.A-246).
  • Table 2-6 Compounds of the formula I.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 I.B.2-6.A-1 to I.B.2-6.A-246).
  • Table 3-1 Compounds of the formula I.C 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.C.3-1.A-1 to I.C.3-1.A-246).
  • Table 3-2 Compounds of the formula I.C in which R 9 is CHF2 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.C.3-2.A-1 to I.C.3-2.A-246).
  • Table 3-3 Compounds of the formula I.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 I.C.3-3.A-1 to I.C.3-3.A-246).
  • Table 3-4 Compounds of the formula I.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 I.C.3-4.A-1 to I.C.3-4.A-246).
  • Table 3-5 Compounds of the formula I.C in which R 9 is OCH3 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.C.3-5.A-1 to I.C.3-5.A-246).
  • Table 3-6 Compounds of the formula I.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 I.C.3-6.A-1 to I.C.3-6.A-246).
  • Table 4-1 Compounds of the formula I. D 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.D.4-1.A-1 to I.D.4-1.A-246).
  • Table 4-2 Compounds of the formula I.D in which R 9 is CHF2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Ta- ble A (compounds I.D.4-2.A-1 to I.D.4-2.A-246).
  • Table 4-3 Compounds of the formula I.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 I.D.4-3.A-1 to I.D.4-3.A-246).
  • Table 4-4 Compounds of the formula I.D in which R 9 is Br and the meaning for the combina- tion of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.D.4-4.A-1 to I.D.4-4.A-246).
  • Table 4-5 Compounds of the formula I.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 I.D.4-5.A-1 to I.D.4-5.A-246).
  • Table 4-6 Compounds of the formula I.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 I.D.4-6.A-1 to I.D.4-6.A-246).
  • Table 5-1 Compounds of the formula I.E 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.E.5-1.A-1 to I.E.5-1.A-246).
  • Table 5-2 Compounds of the formula I.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 I.E.5-2.A-1 to I.E.5-2.A-246).
  • Table 5-3 Compounds of the formula I.E in which R 9 is C ⁇ CH and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.E.5-3.A-1 to I.E.5-3.A-246).
  • Table 5-4 Compounds of the formula I.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 I.E.5-4.A-1 to I.E.5-4.A-246).
  • Table 5-5 Compounds of the formula I.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 I.E.5-5.A-1 to I.E.5-5.A-246).
  • Table 5-6 Compounds of the formula I.E in which R s 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 I.E.5-6.A-1 to I.E.5-6.A-246).
  • Table 6-1 Compounds of the formula I.F 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.F.6-1 .A-1 to I.F.6-1.A-246).
  • Table 6-2 Compounds of the formula I.F in which R 9 is CHF2 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.F.6-2.A-1 to I.F.6-2.A-246).
  • Table 6-3 Compounds of the formula I.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 Ta- ble A (compounds I.F.6-3.A-1 to I.F.6-3.A-246).
  • Table 6-4 Compounds of the formula I.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 I.F.6-4.A-1 to I.F.6-4.A-246).
  • Table 6-5 Compounds of the formula I.F in which R 9 is OCH3 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.F.6-5.A-1 to I.F.6-5.A-246).
  • Table 6-6 Compounds of the formula I.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 I.F.6-6.A-1 to I.F.6-6.A-246).
  • Table 7-1 Compounds of the formula I.G 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.G.7-1.A-1 to I.G.7-1.A-246).
  • Table 7-2 Compounds of the formula I.G in which R 9 is CHF2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Ta- ble A (compounds I.G.7-2.A-1 to I.G.7-2.A-246).
  • Table 7-4 Compounds of the formula I.G in which R 9 is Br and the meaning for the combina- tion of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.G.7-4.A-1 to I.G.7-4.A-246).
  • Table 7-5 Compounds of the formula I.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 I.G.7-5.A-1 to I.G.7-5.A-246).
  • Table 7-6 Compounds of the formula I.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 I.G.7-6.A-1 to I.G.7-6.A-246).
  • Table 8-1 Compounds of the formula I.H 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.H.8-1.A-1 to I.H.8-1.A-246).
  • Table 8-2 Compounds of the formula I.H in which R 9 is CHF2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Ta- ble A (compounds I.H.8-2.A-1 to I.H.8-2.A-246).
  • Table 8-3 Compounds of the formula I.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 I.H.8-3.A-1 to I.H.8-3.A-246).
  • Table 8-4 Compounds of the formula I.H in which R 9 is Br and the meaning for the combina- tion of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.H.8-4.A-1 to I.H.8-4.A-246).
  • Table 8-5 Compounds of the formula I.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 I.H.8-5.A-1 to I.H.8-5.A-246).
  • Table 8-6 Compounds of the formula I.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 I.H.8-6.A-1 to I.H.8-6.A-246).
  • Table 9-1 Compounds of the formula I.I 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 1.1.9-1.A-1 to 1.1.9-1.A-246).
  • Table 9-2 Compounds of the formula I.I in which R 9 is CHF2 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.I.9-2.A-1 to 1.1.9-2.A-246).
  • Table 9-3 Compounds of the formula I.I in which R 9 is C ⁇ CH and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.I.9-3.A-1 to I.I.9-3.A-246).
  • Table 9-4 Compounds of the formula I.I 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.I.9-4.A-1 to 1.1.9-4.A-246).
  • Table 9-5 Compounds of the formula I.I 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.I.9-5.A-1 to I.I.9-5.A-246).
  • Table 9-6 Compounds of the formula I.I 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 I.I.9-6.A-1 to I.I.9-6.A-246).
  • Table 10-1 Compounds of the formula I.J in which R 9 is 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.J.10-1.A-1 to I.J.10-1.A-246).
  • Table 10-2 Compounds of the formula I.J 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.J.10-2.A-1 to I.J.10-2.A-246).
  • Table 10-3 Compounds of the formula I.J 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 Ta- ble A (compounds I.J.10-3.A-1 to I.J.10-3.A-246).
  • Table 0-4 Compounds of the formula I.J 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.J.10-4.A-1 to I.J.10-4.A-246).
  • Table 10-5 Compounds of the formula I.J in which R 9 is OCH3 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.J.10-5.A-1 to I.J.10-5.A-246).
  • Table 10-6 Compounds of the formula I.J 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 I.J.10-6.A-1 to I.J.10-6.A-246).
  • Table 1 1 -1 Compounds of the formula I. K in which R s 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.K.1 1-1.A-1 to I. K.1 1-1.A-246).
  • Table 1 1 -2 Compounds of the formula I.K 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 Ta- ble A (compounds I. K.1 1-2.A-1 to I. K.1 1-2.A-246).
  • Table 1 1 -3 Compounds of the formula I.K 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. K.1 1-3.A-1 to I. K.1 1-3.A-246).
  • Table 1 1 -4 Compounds of the formula I.K in which R 9 is Br and the meaning for the combina- tion of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds I.K.1 1-4.A-1 to I. K.1 1-4.A-246).
  • Table 1 1 -5 Compounds of the formula I.K 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.K.1 1-5.A-1 to I.K.1 1-5.A-246).
  • Table 1 1 -6 Compounds of the formula I.K 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 I.K.1 1-6.A-1 to I.K.1 1-6.A-246).
  • Table12- 1 Compounds of the formula I.L 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.L.1 1-1.A-1 to I.L.1 1-1.A-246).
  • Table12- 2 Compounds of the formula I.L in which R 9 is CHF2 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.L.1 1-2.A-1 to I.L.1 1-2.A-246).
  • Table12- 3 Compounds of the formula I.L 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.L.1 1-3.A-1 to I.L.1 1-3.A-246).
  • Table12- 4 Compounds of the formula I.L 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.L.1 1-4.A-1 to I.L.1 1-4.A-246).
  • Table12- 5 Compounds of the formula I.L 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.L.1 1-5.A-1 to I.L.1 1-5.A-246).
  • Table12- 6 Compounds of the formula I.L 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 I.L.1 1-6.A-1 to I.L.11 -6.A-246).
  • Particular embodiments of the compounds X are the following compounds X.A -X.L.
  • the substituents R 4 , R 78 , o, R 9 , R 10 are independently as defined in claim 1 or preferabl defined herein:
  • Table 1-1 Compounds of the formula X.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.A.1 -1.A-1 to X.A.1-1 .A-246).
  • Table 1-2 Compounds of the formula X.A in which R 9 is CHF2 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.A.1 -2.A-1 to X.A.1-2.A-246).
  • Table 1-3 Compounds of the formula X.A in which R 9 is C ⁇ CH and the meaning for the com- bination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.A.1 -3.A-1 to X.A.1-3.A-246).
  • Table 1-4 Compounds of the formula X.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.A.1-4.A-1 to X.A.1-4.A-246).
  • Table 1-5 Compounds of the formula X.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.A.1 -5.A-1 to X.A.1-5.A-246).
  • Table 1-6 Compounds of the formula X.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.A.1-6.A-1 to X.A.1-6.A-246).
  • Table 2-1 Compounds of the formula X.B 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 X.B.2-1.A-1 to X.B.2-1 .A-246).
  • Table 2-2 Compounds of the formula X.B in which R 9 is CHF2 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.B.2-2.A-1 to X.B.2-2.A-246).
  • Table 2-4 Compounds of the formula X.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 X.B.2-4.A-1 to X.B.2-4. A-246).
  • Table 2-5 Compounds of the formula X.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 Ta- ble A (compounds X.B.2-5.A-1 to X.B.2-5.A-246).
  • Table 2-6 Compounds of the formula X.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 X.B.2-6.A-1 to X.B.2-6. A-246).
  • Table 3-1 Compounds of the formula X.C in which R 9 is CH3 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.C.3-1 .A-1 to X.C.3-1.A-246).
  • Table 3-2 Compounds of the formula X.C in which R 9 is CHF2 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.C.3-2.A-1 to X.C.3-2.A-246).
  • Table 3-3 Compounds of the formula X.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 X.C.3-3.A-1 to X.C.3-3.A-246).
  • Table 3-4 Compounds of the formula X.C in which R s is Br and the meaning for the combina- tion of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.C.3-4.A-1 to X.C.3-4.A-246).
  • Table 3-5 Compounds of the formula X.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 X.C.3-5.A-1 to X.C.3-5.A-246).
  • Table 3-6 Compounds of the formula X.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 X.C.3-6.A-1 to X.C.3-6.A-246).
  • Table 4-1 Compounds of the formula X.D 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 Ta- ble A (compounds X.D.4-1 .A-1 to X.D.4-1.A-246).
  • Table 4-2 Compounds of the formula X.D in which R 9 is CHF2 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.D.4-2.A-1 to X.D.4-2.A-246).
  • Table 4-4 Compounds of the formula X.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 X.D.4-4.A-1 to X.D.4-4.A-246).
  • Table 4-5 Compounds of the formula X.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 X.D.4-5.A-1 to X.D.4-5.A-246).
  • Table 4-6 Compounds of the formula X.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 X.D.4-6.A-1 to X.D.4-6.A-246).
  • Table 5-1 Compounds of the formula X.E 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 X.E.5-1.A-1 to X.E.5-1 .A-246).
  • Table 5-2 Compounds of the formula X.E in which R 9 is CHF2 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.E.5-2.A-1 to X.E.5-2.A-246).
  • Table 5-3 Compounds of the formula X.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 X.E.5-3.A-1 to X.E.5-3.A-246).
  • Table 5-4 Compounds of the formula X.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 X.E.5-4.A-1 to X.E.5-4.A-246).
  • Table 5-5 Compounds of the formula X.E in which R 9 is OCH3 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.E.5-5.A-1 to X.E.5-5.A-246).
  • Table 5-6 Compounds of the formula X.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 X.E.5-6.A-1 to X.E.5-6.A-246).
  • Table 6-1 Compounds of the formula X.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 X.F.6-1 .A-1 to X.F.6-1 .A-246).
  • Table 6-2 Compounds of the formula X.F in which R 9 is CHF2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.F.6-2.A-1 to X.F.6-2.A-246).
  • Table 6-3 Compounds of the formula X.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 X.F.6-3.A-1 to X.F.6-3.A-246).
  • Table 6-4 Compounds of the formula X.F in which R 9 is Br and the meaning for the combina- tion of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.F.6-4.A-1 to X.F.6-4.A-246).
  • Table 6-5 Compounds of the formula X.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 X.F.6-5.A-1 to X.F.6-5.A-246).
  • Table 6-6 Compounds of the formula X.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 X.F.6-6.A-1 to X.F.6-6.A-246).
  • Table 7-1 Compounds of the formula X.G 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 Ta- ble A (compounds X.G.7-1.A-1 to X.G.7-1.A-246).
  • Table 7-2 Compounds of the formula X.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 X.G.7-2.A-1 to X.G.7-2.A-246).
  • Table 7-3 Compounds of the formula X.G in which R 9 is C ⁇ CH and the meaning for the com- bination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.G.7-3.A-1 to X.G.7-3.A-246).
  • Table 7-4 Compounds of the formula X.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 X.G.7-4.A-1 to X.G.7-4.A-246).
  • Table 7-5 Compounds of the formula X.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 X.G.7-5.A-1 to X.G.7-5.A-246).
  • Table 7-6 Compounds of the formula X.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 X.G.7-6.A-1 to X.G.7-6.A-246).
  • Table 8-1 Compounds of the formula X.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 X.H.8-1 .A-1 to X.H.8-1.A-246).
  • Table 8-2 Compounds of the formula X.H in which R 9 is CHF2 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.H.8-2.A-1 to X.H.8-2.A-246).
  • Table 8-3 Compounds of the formula X.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 Ta- ble A (compounds X.H.8-3.A-1 to X.H.8-3.A-246).
  • Table 8-4 Compounds of the formula X.H 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.H.8-4.A-1 to X.H.8-4.A-246).
  • Table 8-5 Compounds of the formula X.H in which R 9 is OCH3 and the meaning for the com- bination of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.H.8-5.A-1 to X.H.8-5.A-246).
  • Table 8-6 Compounds of the formula X.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 X.H.8-6.A-1 to X.H.8-6.A-246).
  • Table 9-1 Compounds of the formula X.I 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 X.X.9-1.A-1 to X.X.9-1 .A-246).
  • Table 9-2 Compounds of the formula X.I in which R 9 is CHF2 and the meaning for the combination of R 4 and R 10 for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.X.9-2.A-1 to X.X.9-2.A-246).
  • Table 9-4 Compounds of the formula X.I in which R 9 is Br and the meaning for the combina- tion of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.X.9-4.A-1 to X.X.9-4.A-246).
  • Table 9-5 Compounds of the formula X.I 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.X.9-5.A-1 to X.X.9-5.A-246).
  • Table 9-6 Compounds of the formula X.I 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.X.9-6.A-1 to X.X.9-6.A-246).
  • Table 10-1 Compounds of the formula X.J in which R 9 is CH3 and the meaning for the combina- tion of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.J.10-1.A-1 to X.J.10-1.A-246).
  • Table 10-2 Compounds of the formula X.J 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.J.10-2.A-1 to X.J.10-2.A-246).
  • Table 10-3 Compounds of the formula X.J 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 X.J.10-3.A-1 to X.J.10-3.A-246).
  • Table 10-4 Compounds of the formula X.J 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.J.10-4.A-1 to X.J.10-4.A-246).
  • Table 10-5 Compounds of the formula X.J 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.J.10-5.A-1 to X.J.10-5.A-246).
  • Table 10-6 Compounds of the formula X.J 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.J.10-6.A-1 to X.J.10-6.A-246).
  • Table 1 1 -1 Compounds of the formula X.K 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.K.1 1-1.A-1 to X.K.1 1-1.A-246).
  • Table 1 1 -2 Compounds of the formula X.K in which R 9 is CHF2 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.K.1 1-2.A-1 to X.K.1 1-2.A-246).
  • Table 1 1 -3 Compounds of the formula X.K 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 Ta- ble A (compounds X.K.1 1-3.A-1 to X.K.1 1-3.A-246).
  • Table 1 1 -4 Compounds of the formula X.K 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.K.1 1 -4.A-1 to X.K.11-4.A-246).
  • Table 1 1 -5 Compounds of the formula X.K in which R 9 is OCH3 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.K.1 1-5.A-1 to X.K.1 1-5.A-246).
  • Table 1 1 -6 Compounds of the formula X.K 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.K.1 1-6.A-1 to X.K.1 1-6.A-246).
  • Table 12- 1 Compounds of the formula X.L 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 X.L.12-1.A-1 to X.L.12-1.A-246).
  • Table 12- 2 Compounds of the formula X.L in which R 9 is CHF2 and the meaning for the combi- nation of R 4 and R 10 for each individual compound corresponds in each case to one line of Table A (compounds X.L.12-2.A-1 to X.L.12-2.A-246).
  • Table 12- 3 Compounds of the formula X.L 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 X.L.12-3.A-1 to X.L.12-3.A-246).
  • Table 12- 4 Compounds of the formula X.L 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.L.12-4.A-1 to X.L.12-4.A-246).
  • Table 12- 5 Compounds of the formula X.L 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 Ta- ble A (compounds X.L.12-5.A-1 to X.L.12-5.A-246).
  • Table 12- 6 Compounds of the formula X.L 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.L.12-6.A-1 to X.L.12-6. A-246).
  • Table A Compounds X.L.12-6.A-1 to X.L.12-6. A-246).
  • 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.
  • 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.
  • compounds I and compositions thereof 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.
  • 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.
  • 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.
  • 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.
  • cultiva 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 ob- tained by cross breeding, mutations or natural recombination.
  • 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.
  • auxin herbi- cides such as dicamba or 2,4-D
  • bleacher herbicides such as hydroxylphenylpyruvate dioxy
  • herbicides 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.
  • BASF SE Germany
  • imidazolinones e. g. imazamox
  • ExpressSun ® sunflowers DuPont, USA
  • sulfonyl ureas e. g. tribenuron.
  • 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 ⁇ -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 nematodes, e. g. Photorhabdus spp.
  • VIP1 , VIP2, VIP3 or VIP3A vegetative insecticidal proteins
  • 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
  • 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.
  • 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).
  • 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.
  • 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).
  • PR proteins pathogenesis- related proteins
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum
  • T4-lysozym e. g. potato cultivars capable of synthe
  • plants are also covered that are by the use of recombinant DNA techniques capa- ble 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.
  • productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
  • 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).
  • 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); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A brassico/a or brassi- cae), sugar beets (A tenuis), fruits, rice, soybeans, potatoes (e. g. A solani or A alternata), tomatoes (e. g. A solani OK A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g.
  • Botrytis cinerea teleomorph: Botryotinia fuckeliana. grey mold
  • 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
  • Ceratocystis syn. Ophiostoma
  • spp. rot or wilt
  • 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 ox C. k/kuchi/) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C.
  • herbarum black ear
  • Claviceps purpurea ergot
  • Cochliobolus anamorph: Helminthosporium of Bipolaris
  • spp. leaf spots
  • corn C. carbonum
  • cereals e. g. C. sativus, anamorph: B. soro- kiniana
  • rice e. g. C. miyabeanus, anamorph: H. oryzae
  • Colletotrichum teleomorph: Glo- merella
  • spp. anthracnose
  • cotton e. g. C. gossypii
  • corn e. g. C.
  • graminicola Anthracnose stalk rot
  • soft fruits e. g. C. coccodes: black dot
  • beans e. g. C. lindemuthi- anum
  • soybeans e. g. C. truncatum or C. gloeosporioides
  • Corticium spp. e. g. C. sasakii (sheath blight) on rice
  • Corynespora cassiicola leaf spots
  • Cy- cloconium spp. e. g. C. oleaginum on olive trees
  • Cylindrocarpon spp. e. g.
  • teleomorph Nectria or Neonectria spp.
  • fruit trees canker or young vine decline
  • teleomorph Nectria or Neonectria spp.
  • fruit trees canker or young vine decline
  • teleomorph Nectria or Neonectria spp.
  • fruit trees vines
  • teleomorph Neonectria liriodendri. Black Foot Disease
  • 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.
  • Phaeomoniella chlamydospora (earlier Phaeo- acremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa
  • 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.
  • cucurbits e. g. E. cichoracearum
  • cabbages rape (e. g. E. cruciferarum)
  • Eutypa lata Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertell
  • Bakanae disease Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochlioboius) on corn, cereals and rice; Hemi/eiaspp., e. g. H.
  • 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.
  • phaseoll, teleomorph Diaporthe phaseolorum
  • Phy- soderma maydis brown spots
  • Phytophthora spp. wilt, root, leaf, fruit and stem root
  • paprika and cucurbits e. g. P. capsicl
  • soybeans e. g. P.
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers
  • Podosphaera spp. powdery mildew
  • hum/lion 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.
  • Pyrenophora anamorph: Drechslera
  • tritici-repentis tan spot
  • P. teres net blotch
  • 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 Roso-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.
  • Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum
  • pruni plum pocket
  • Thielaviopsis spp. black root rot
  • tobacco, pome fruits, vegetables, soybeans and cotton e. g. T. basicola (syn. Chalara elegans)
  • Tilletia spp. common bunt or stinking smut
  • cereals such as e. g. T. tritici ⁇ syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat
  • Typhula incarnata grey snow mold
  • Urocystis spp. e. g. U.
  • occulta stem smut
  • Uromyces spp. rust
  • vegetables such as beans (e. g. U. appendicu/atus, 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
  • Venturia spp. scab
  • apples e. g. V. inaequalis
  • pears 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 harm- ful fungi in the protection of stored products or harvest and in the protection of materials.
  • 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.
  • Ascomycetes such as Ophiostom a spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp:, Basidiomycetes such as Coni- ophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Ser- pu/a spp.
  • Ascomycetes such as Ophiostom a spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp:, Basidiomycetes such as Coni
  • Candida spp. and Saccharomyces cerevisae 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.
  • 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.
  • stored products are 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 fur- niture 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 pro- Ded 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.
  • 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.
  • 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
  • tolerance to abiotic and/or biotic stress e. g. improved content or composition of certain ingredients
  • 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 com- prising 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.
  • 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.
  • compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6 th Ed. May 2008, CropLife International.
  • 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; gly- cols; DMSO; ketones, e. g. cyclohexanone; esters, e. g.
  • mineral oil fractions of medium to high boiling point e. g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalen
  • 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.
  • 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, star
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric 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.
  • 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 sul- fates 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, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • 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.
  • N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolygluco- sides.
  • polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl al- cohols, 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 ox- ide, 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 them- selves, 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 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 phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • a compound I and 5-15 wt% wetting agent e. g. alcohol alkoxylates
  • a water-soluble solvent e. g. alcohols
  • Dispersible concentrates 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.
  • a compound I e. g. polyvinyl pyrrolidone
  • organic solvent e. g. cyclohexanone
  • emulsifiers e. g. calcium dodecylbenzenesul- fonate and castor oil ethoxylate
  • water-insoluble organic solvent e. g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e. g. aromatic hydrocarbon
  • a compound I 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.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • 0.1- 2 wt% thickener e. g. xanthan gum
  • a compound I 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.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (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.
  • dispersants e. g. sodium lignosulfonate
  • wetting agents e. g. alcohol ethoxylate
  • solid carrier e. g. silica gel
  • a compound I 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.
  • dispersants e. g. sodium lignosulfonate
  • 1 -5 wt% thickener e. g. carboxymethyl cellulose
  • a compound I 5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl 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.
  • organic solvent blend e. g. fatty acid dimethyl amide and cyclohexanone
  • surfactant blend e. g. alcohol ethoxylate and ar- ylphenol ethoxylate
  • 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.
  • 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).
  • a protective colloid e. g. polyvinyl alcohol.
  • the addition of a polyamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1 - 10 wt%.
  • the wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • a compound I 1 -10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.
  • solid carrier e. g. finely divided kaolin
  • a compound I 0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%.
  • solid carrier e. g. silicate
  • Granulation is achieved by extrusion, spray-drying or fluidized bed.
  • organic solvent e. g. aromatic hydrocarbon
  • 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% colorants.
  • 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).
  • 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.
  • 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.
  • 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.
  • 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.
  • the amount of active substance ap- plied 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.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides 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).
  • pesticides e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides
  • 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 pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease.
  • 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 facili- tate 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 reduce 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.
  • 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.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention 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 ap- intestinalte.
  • one embodiment of the invention is a kit for preparing a usable pesticidal composition, 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 option- ally a further active component 3) as defined herein.
  • pesticides II e. g. pesticidally-active substances and biopesticides
  • the compounds I in conjunction with which the compounds I can be used, is intended to illustrate the possible combinations but does not limit them:
  • Inhibitors of complex III at Q 0 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.
  • 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);
  • - 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.1.11), 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), pen
  • 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);
  • nucleic acid synthesis inhibitors hymexazole (C.2. ), 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);
  • tubulin inhibitors benomyl (D.1 .1 ), carbendazim (D.1 .2), fuberidazole (D1.3), thiabendazole (D. .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-
  • 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);
  • cyprodinil E.1.1
  • mepanipyrim E.1.2
  • pyrimethanil E.1.3
  • 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);
  • MAP / histidine kinase inhibitors fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1 .4), fludioxonil (F.1.5);
  • quinoxyfen F.2.1 ;
  • edifenphos G.1.1
  • iprobenfos G.1.2
  • pyrazophos G.1.3
  • isoprothiolane G.1.4
  • 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
  • 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.3J
  • propamocarb (G.4.1 );
  • 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
  • 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 );
  • 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;
  • - melanin synthesis inhibitors pyroquilon (1.2.1 ), tricyclazole (I.2.2), carpropamid (I.2.3), dicy- clomet (I.2.4), fenoxanil (I.2.5);
  • 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, padobutrazol, prohexadione, prohexadi- one-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithio
  • 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,
  • 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, nico
  • 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, brom
  • 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
  • N.5 Bleacher herbicides beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,
  • norflurazon picolinafen, 4-(3-trifluoromethy phenoxy)-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);
  • Glutamine synthase inhibitors bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;
  • 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, 11.3 , II.4, II.5, II.6, II.7, II.8 and II.9
  • Cellulose biosynthesis inhibitors chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1-cyclohexyl-5-pentafluorphenyloxy-14-[ ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1);
  • 2,4-D and its salts and esters 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,
  • 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, cyanopho
  • GABA-gated chloride channel antagonists endosulfan, chlordane; ethiprole, fipronil,
  • 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, fluc
  • Nicotinic acetylcholine receptor agonists acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam;
  • Nicotinic acetylcholine receptor allosteric activators spinosad, spinetoram; 0.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbe- mectin;
  • Juvenile hormone mimics hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;
  • miscellaneous non-specific (multi-site) inhibitors methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;
  • 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.
  • israeltaki Bacillus thuringiensis subsp. tenebrionis, the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 ;
  • Inhibitors of mitochondrial ATP synthase diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;
  • Nicotinic acetylcholine receptor (nAChR) channel blockers bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium;

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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 compounds 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-halocycloalkyl, Ci-C4-hal ogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R11a selected from the group consisting of hal ogen, 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 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;
R2 is in each case independently selected from the substituents as defined for R1 , wherein the possible substituents for R2 are R2a and R2 , respectively, which correspond to R1a and R1 b, respectively;
R3 is in each case independently selected from CH3, CH2F, CHF2 and CF3; 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-halogen- alkoxy, CH(=0),
Figure imgf000003_0001
Figure imgf000003_0002
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, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-al- kyl)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-Ce-halogenalkoxy, C3-C6-cycloal- kyl, 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)d-C4- alkyl),
Figure imgf000003_0003
NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C5- alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0),
Figure imgf000003_0004
Ce-alkyl,
Figure imgf000003_0005
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 se- lected from the group consisting of halogen, OH, CN , NO2, SH , N H2, NH(Ci-C4-al- kyl), N(CrC4-alkyl)2, N
Figure imgf000004_0001
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 R4 , which independently of one another are selected from:
R b halogen, OH , CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N
Figure imgf000004_0002
alkyl),
Figure imgf000004_0003
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 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, d-Ce-alkyl, Ci-Ce-halogen- alkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, C1-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 , CrC4-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 ;
o is 0, 1 , 2 or 3; and
R78 are independently selected from halogen, OH , CN, N02, SH, N H2, N H(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, CH(=0),
Figure imgf000004_0004
C(=0)N H(CrC6-alkyl), CR'=NOR", C C6-alkyl, C 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-membered 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 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 R78 which independently of one another are selected from: R78b halogen, OH , CN, Ci-C4-alkyl, Ci-C4-alkoxy, d-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, NH (C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4-alkynyl)2, N H(C3-C3-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
Figure imgf000005_0001
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)N H(Ci- Ce-alkyl), CH(=S),
Figure imgf000005_0002
C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-
Cs-cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, C2-CB-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, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C3-Ce-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: 9b 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;
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, N H2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-Ce-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, CrC4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthioand 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.
Figure imgf000007_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 III 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 II can be prepared as described below, A skilled person will realize that compounds of type lllb can be reacted with organometaiiic 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 imgf000007_0002
lllb
Alternatively, alcohols of type II can be prepared from epoxydes Ilia and compounds VI (see be- low):
"metallation"
Figure imgf000007_0003
Ilia VI
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 lllb can be achieved by reacting compounds of type IV with organometallic reagents, preferably alky! 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 imgf000008_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(C2H5)3 or pyridine (see e.g. US 20130324506; Tetrahedron: Asymmetry, 17(4), 508-511 ; 2006). If X = OH, the addition of an activating reagent, preferably a carbodiimide, may be preferred (see for example ChemMedChem, 7(12), 2101 -2112; 2012; 2011038204; Journal of Organic Chemistry, 76(1 ), 164-169; 2011).
Figure imgf000008_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), 2113-2120; 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 copper^) salt, in an organic solvent, preferably DMF or DMSO, at elevated temperatures. Typically a base, preferably potassium phos hate, is added.
Figure imgf000008_0003
VI
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 re- action is performed in a temperature range from -78 °C to room temperature under inert conditions in an ethereal solvent.
Figure imgf000009_0001
Alternatively compounds I in which R6 stands for hydrogen can be accessed by reacting a nitrile III with an olefin ll# under acidic conditions as described elsewhere (US 7632783, B2, page 60, method A .
Figure imgf000009_0002
Alternatively compounds I can be prepared via intramolecular reaction of amide X. The intramo- lecular 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, SnCI4 or BF3 are used as dehydrating agent. Most suitable solvents are hydrocarbons, preferably benzene, toluene or acetonitrile.
Figure imgf000009_0003
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(C2H5)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, 3088-3115).
Figure imgf000010_0001
If required, compounds of type XII can be synthesized from the correspond nitriles. As described 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.
Figure imgf000010_0002
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 tables 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:
Figure imgf000010_0003
The compounds of formula X have fungicidal activity and the details below referring to the compounds I also apply to compounds X.
Particular embodiments of the intermediate X are the following compounds X.A, X.B, X.C, X.D. In these formulae, the substituents R4, R78, o, R9, R10 are independently as defined in claim 1 or
Figure imgf000011_0001
X D
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 "Ci-C6-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 "CrC6-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 "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-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-Ce-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, OCC , 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-Cs-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 "CrC6-alkylthio" as used herein refers to straight-chain or branched alkyl groups hav- ing 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 having 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 : N H(CrC4-alkyl), N(Ci-C4-alkyl)2, NH(C3-C6-cycloalkyl) , N(C3-C6-cycloalkyl)2, C(=0)-N H(Ci-C6- alkyl), C(=0)-N(CrCe-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 corre- sponding -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-thi ad iazol-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 in- vention.
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-halocycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 1a selected from the group consisting of halogen, OH, Ci-C4-alkyl, C1-C4- halogenalkyl, Ci-C4-alkoxy and CrC4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or substituted with identical or different groups R1 b which independently of one another are selected from: R1b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C -halogenalkyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, 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 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 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 Rx1 independently selected from Ci-C4-alkyl. According to still another embodiment of formula I, R1 is CrC6-alkyl, in particular Ci-C4-alkyl,
Figure imgf000016_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 or CH2CI.
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.
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-ECH.
According to still another embodiment of formula I, R1 is Ci-C6-alkoxy, in particular CrC4-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 Cr 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 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-halocycloalkyl. 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, N H-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 R1 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 Ci-C4-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-halocycloalkyl, 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-halocycloalkyl 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-halocycloalkyl 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.
R1 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-halocycloalkyl and Ci-C4-halogenalkoxy.
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-halocycloalky and Ci-C2-halo- genalkoxy. Specifically, R1 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 R1b is independently selected from halogen, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C2-hal- ogenalkoxy. Specifically, R1 is independently selected from halogen, OH, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI- 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 invention. 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 imgf000018_0001
Figure imgf000018_0002
R2 according to the invention 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, CrC6-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-halocycloalky, 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, C1-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 R2 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- halocycloalky, 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 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.
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.
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 CrC6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2 or CH2CI.
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.
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-ECH.
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 CrC6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically CrC2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 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 defined and preferably herein. According to still another embodiment of formula I, R2 is C3-C6-halocycloalky. 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(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 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 R2 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-halocycloalky, 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, CrC4-alkyl, Ci-C4-halogenalkyl, CrC4-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.
According to one embodiment R2a is independently selected from halogen, OH, CN, Ci-C2- alkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalky and Ci-C2-halogenalkoxy. Specifically, R2a 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 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-halocycloalky 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.
R2 according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, CrC4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalky and Ci-C4-halogenalkoxy.
According to one embodiment thereof R2b is independently selected from halogen, CN, Ci-C2- alkyl, Ci-C2-alkoxy, CrC2-halogenalkyl, C3-C6-cycloalkyl, Cs-Ce-halocycloalkyl and Ci-C2-halo- genalkoxy. Specifically, R2 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, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C2-hal- ogenalkoxy. Specifically, R2b is independently selected from halogen, OH, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI- cyclopropyl , OCH F2 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 inven- tion. 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 imgf000021_0002
Figure imgf000021_0003
R3 is in each case independently selected from CH3, CH2F, CH F2 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, substituted Ci- C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halo- genalkynyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-halogenalkoxy, CH(=0),
Figure imgf000021_0001
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, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-Ce-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(C C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)d-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-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),
Figure imgf000022_0001
C(=0)NH(Ci-C6-alkyl),
Figure imgf000022_0002
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, NH2, NH(Ci-C -alkyl), N(Ci-C4-alkyl)2,
Figure imgf000022_0003
alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C -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:
R b halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2,
Figure imgf000022_0004
Figure imgf000022_0005
NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C -halogenalkyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-CB-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),
Figure imgf000022_0006
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, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, S(0)n-Ci-C6-alkyl, NH- S02-Rx, N(Ci-C6-alkyl)2, CH(=0),
Figure imgf000023_0001
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, Cs-Ce-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, Ci-Ce-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, S(0)n-Ci-C6-alkyl, NH-S02-R*, N(Ci-C6- alkyl)2, CH(=0), C(=0)Ci-C6-alkyl,
Figure imgf000023_0002
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-CH2, halogenphenyl-CH2, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted by substitu- ents 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 R4 as defined below. According to one embodiment thereof, the carbo- and het- erocycle 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 R4 as defined 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 de- fined 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 CrC6-alkylthio, such as SCH3, SC2H5, Sn-propyl, Si-propyl, Sn-butyl, Si-butyl, Stert-butyl, Sn-pentyl or Si-pentyl.
According to still another embodiment of formula I, R4 is Ci-C6-halogenalkylthio, such as SCF3, SCC .
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,
Figure imgf000024_0001
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),
Figure imgf000024_0002
C(=0)NH(Ci-C6-alkyl),
Figure imgf000024_0003
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, NH2, NH(C C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)d-C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C -halogenalkyl, C1-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:
R a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2,
Figure imgf000024_0004
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),
Figure imgf000024_0005
C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl),
Figure imgf000024_0006
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, NH2, NH(C C4-alkyl), N(Ci-C4-alkyl)2,
Figure imgf000024_0007
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, d-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,
Figure imgf000025_0001
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),
Figure imgf000025_0002
C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl),
Figure imgf000025_0003
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, 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-CB-alkylthio, CrC4-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 CN.
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-Ce-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-ECH, C..C-CI, C≡C-CH3, 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 Ci-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
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
CH2OCH3 or CH2OCH2CH3
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
According to a further specific embodiment of formula I , R4 is Ci-C6-halogenalkoxy, in particular CrC4-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-CrC6-halogenalkoxy, in particular Ci-C4-alkyl-Ci-C4-halogenalkoxy, more specifically Ci-C2-alkyl-CrC2-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)CrC6-alkyl,
Figure imgf000026_0001
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)CrC6-alkyl, Ci-C4-alkyl-C(=0)0(Ci-C6-alkyl), Ci-C4-alkyl-C(=0)NH(Ci-C6-alkyl) or C1-C4- alkyl-C(=0)N(Ci-C6-alkyl)2, especially CH2CH(=0), CH2C(=0)Ci-Ce-alkyl,
Figure imgf000026_0002
alkyl),
Figure imgf000026_0003
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-alkylthio, in particular C1-C4- alkoxy, more specifically Ci-C3-alkylthio such as CH2SCH3 or CH2SCH2CI-l3.According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl substituted by CN such as CH2CN
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl-S(0)n-Ci-C6-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 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 selected from Ci-C6-alkyl which is sub- stituted, 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 selected from Ci-C6-alkyl which is substituted, a 3-mem- bered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4 . According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R4 is selected from Ci-C6-alkyl which is substituted, a 4-mem- bered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4 . According to still another embodiment of formula I, it is substituted by R4b.
According to one embodiment, R4 is selected from Ci-C6-alkyl which is substituted, a 5- membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R4 . According to still another embodiment of formula I, it is substituted by R4 .
According to one embodiment, R4 is selected from Ci-C6-alkyl which is substituted, 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-alky{, especially Chb substituted by 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 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 em- bodiment, 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 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 CH2 substituted by a 5-membered saturated heterocycle which contains one N as ring member and optionally one or two groups CH2 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-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 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 R4 .
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 R4 . 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-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 R4 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 mem- bers. 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 R .
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 P4-128 corresponds to one particular embodiment of the invention, wherein P4-1 to P4-128 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 imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_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 substit- uent 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, Ci-Ce-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogen- alkoxy, 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-C 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).
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 R4 . According to still another embodiment of formula I, it is substituted by R4 .
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 R4 . According to still another embodiment of formula I, it is substituted by R4 .
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 R4 . According to still another embodiment of formula I, it is substituted by R4 .
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 R4 . According to still another embodiment of formula I, it is substituted by R4 .
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 R4 . According to still another embodiment of formula I, it is substituted by R4 .
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 R4 . 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 P34-534 corresponds to one particular embodiment of the invention, wherein P34-1 to P34-534 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 S02-(p-CH3)phenyl. Table P34
Figure imgf000036_0002
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_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(Ci-C4-alkyl), N(C C4-alkyl)2,
Figure imgf000052_0002
NH-S02-R*, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0),
Figure imgf000053_0001
CR'=NOR", heterocarbocycle, aryl and phenoxy, wherein the aryl and phenyl groups are independently un- substituted 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-al- kyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C -halogen- alkoxy 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 halo- gen, OH, CN, NH-S02-R*, CH(=0),
Figure imgf000053_0002
kyl) and CR'=NOR".
According to one preferred embodiment, R4a is in each case independently selected from halogen, OH, CN, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and heterocycle, wherein the heretocy- clocycle is a satureated 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-halocycloalkyl and heterocycle, wherein the heretocy- clocycle 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 halo- gen, OH, CN, C3-C6-cycloalkyl, C3-C6-halocycloalkyl 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 substi- tuted 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-halocycloalkyl, CrC6-alkoxy, Ci-C -halogenalkoxy, CrC6- 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, Ci-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 halogen 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(Ci-C -alkyl), N(Ci-C4- alkyl)2,
Figure imgf000053_0003
NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, 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 substituted with substituents selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy.
According to one preferred embodiment, R4b is in each case independently selected from halogen, OH, CN, SH, Ci-C6-alkyl, Ci-CB-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C1-C6- alkylthio and S(0)n-Ci-C6-alkyl. According to one further preferred embodiment, R4b is in each case independently selected from halogen, Ci-C5-alkoxy, CrC6-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 further 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, R4 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 SO2CH3.
R5 is H.
R6 is H.
R78 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl),
N(Ci-C4-alkyl)2,
Figure imgf000054_0001
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, CH(=0),
Figure imgf000054_0002
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:
R78a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-CB-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halocycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, 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, C1-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:
R78 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 N02.
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(CrC4-alkyl)2, in particular
NH(CH3)2, NH(C2H5)2.
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-S02-CH3, NH-S02-CH2-CH3, NH-S02-CF3 or NH-S02-Ts.
According to a further specific embodiment of formula I, R78 is CH(=0), 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, 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 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, 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 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. 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 or CH2- C CH.
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 CrC4-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 , 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
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 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 one embodiment, R78 is a 3-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 4-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 R78 .
According to one embodiment, R78 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R78 . According to still another embodiment of formula I, it is substituted by R78b.
According to one embodiment, R78 is a 6-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 R78 .
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-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 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-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 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 heteroatom. 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, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, 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 in each case independently selected from halogen, CN, Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Cs-alkoxy, 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 carbo- and het- erocycle 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-CB-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-CB-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-Cs-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Cs-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 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 phenyl ring, optionally substituted by (R78)0, according to the invention are in Table P78 below, wherein each line of lines P78-1 to P78-40 corresponds to one particular embodiment of the invention, wherein P78-1 to P78-40 are also in any combi- nation 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 imgf000059_0001
Table P78: No. (R78)o No. (R78)o
P78-14 2'-CN P78-27 3'-CN
P78-15 3'-F P78-28 4'-F
P78-16 3 -CI P78-29 4'-CI
P78-17 3'-Br P78-30 4'-Br
P78-18 3'-CH3 P78-31 4'-CH3
P78-19 3 -C2H5 P78-32 4'-C2H5
P78-20 3'-CH2F P78-33 4'-CH2F
P78-21 3'-CHF2 P78-34 4'-CHF2
P78-22 3'-CF3 P78-35 4'-CF3
3'-OCH3 P78-36 4'-OCH3
P78-23
P78-37 4'-OCH2F
P78-38 4'-OCHF2
P78-24 3'-OCH2F
P78-39 4'-OCF3
P78-25 3'-OCHF2
Figure imgf000060_0001
P78-40 4'-CN
P78-26 3'-OCF3
R9 is in each case independently selected from H, 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-al- kynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-al- kyl)(C2-C -alkynyl), N(C2-C -alkyl)(C3-C6-cycloalkyl), N(C2-C -alkenyl)(C2-C -alkynyl), N(C2-C - 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-R*, S(0)n-Ci-C6-alkyl, S(0)n-aryl, Ci-C6-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-C3- alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)NH(C C6-alkyl), CH(=S), C(=S)CrC6-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
is as defined above;
is CrC6-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 R9 are unsubstituted or substituted by groups R9a which independently of one another are selected from: R9a halogen, OH, CN, Ci-Ce-alkoxy, Ca-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci- C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is un- substituted 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-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 l, R9 is CI.
According to still another embodiment of formula l, R9 is Br.
According to still another embodiment of formula l, R9 is OH.
According to still another embodiment of formula l, R9 is CN.
According to still another embodiment of formula I, R9 is N02.
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 l, R9 is , N(Ci-C4-alkyl)2, in particular NH(CH3)
According to still another embodiment of formula l, 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 l, R9 is , N(C2-C4-alkynyl)2, in particular N(C CH)2, N(CH2C≡CH)2.
According to still another embodiment of formula l, 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(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, 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
Figure imgf000062_0001
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)(C4Hg), 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-S02-CH3, NH-S02-CH2-CH3, NH-S02-CF3, NH-S02-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(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, 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- C6-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)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 , 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 (C4H9).
According to a further specific embodiment of formula I , Rs 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-Ce-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 C1-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, CCI2CC 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.
According to a further specific embodiment of formula I , R9 is ORY, wherein RY is CrC6-alkyl, Cr C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3- Ce-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 OCHC .
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
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-halocycloal- kyl. 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 R9 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 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 R9 which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br,
Figure imgf000064_0001
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 halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br, CH3, OCH3, 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-C3-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl 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 carbocyclic, 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, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl, 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 cycloalkyl moieties of R9 are unsubstituted or substituted with identical or different groups R9b as defined and preferably defined herein.
According to one embodiment R9a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyl, C3-C6-halocycloalkyl 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 cycloalkyl, 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-halocycloalkyl, Ci-C4-halogenalkoxy and Ci- C6-alkylthio.
According to one embodiment thereof RSb 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 Rs 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 in- vention, 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:
No. R9 No. R9
P13-1 H P13-9 CH2CH2CH2CH3
P13-2 CH3 P13-10 CH2CH(CH3)2
P13-3 CH2F P13-1 1 C(CH3)3
P13-4 CH F2 P13-12 CH2CH2CH2CH2CH3
P13-5 CF3 P13-13 CH=CH2
P13-6 C2H5 P13-14 CH2CH=CH2
P13-7 CH(CH3)2 P13-15 C≡CH
P13-8 CH2CH2CH3 P13-16 CH2C≡CH
Figure imgf000066_0001
R10 is in each case independently selected from H , halogen, OH , CN , NO2, SH , NH2, NH(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-C3-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-al- kyl)(C2-C4-alkynyl), N(C2-C -alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C -alkynyl), N(C2-C - alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl),
Figure imgf000066_0002
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),
Figure imgf000066_0003
alkynyl, C(=0)C3-C6-cyclpalkyl, C(=0)N H(CrC3-alkyl), CH(=S) ,
Figure imgf000066_0004
C(=S)C2-C6- alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cyclpalkyl, 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, 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-halocycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted 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, 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, R10 is secected 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 and ORY.
According to one embodiment of formula I, R10 is H.
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 R10 is , N(Ci-C4-alkyl)2, in particular
NH(CH3)2, NH(C2H5)2.
According to still another embodiment of formula R10 is , NH(C2-C4-alkenyl), in particular NH(CH=CH2), NH(CH2CH=CH2).
According to still another embodiment of formula R10 is , N(C2-C4.-alkenyl)2, in particular N(CH=CH2)2, N(CH2CH=CH2)2.
According to still another embodiment of formula R10 is , NH(C2-C4-alkynyl), in particular NH(C ≡CH), NH(CH2C≡CH).
According to still another embodiment of formula 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-SO2- CH3, NH-SO2-CH2-CH3, NH-SO2-CF3, NH-SO2-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
Figure imgf000068_0001
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- C6-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 alkynyl 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, CCI2CC 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.
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-alkynyl, 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 CrC2-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
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-halocycloal- kyl. 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-CI2-cyclopropyl
According to still another embodiment of formula I, R10 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 R10b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br,
Figure imgf000070_0001
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 halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and CrC2-halogenalkoxy, in particular F, CI, Br, CH3, OCH3, 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, 69yrazine69-1 -yl, 69yrazine69-2-yl, 69yrazine69-4-yl, 69yra- zine69-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thia- zol-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-thiadi- azol-3-yl, 1 ,2,4-thiadiazol-5-yl.
According to still another embodiment of formula I, R10 is a 6-membered heteroaryl such as 69yrazine-2-yl, 69yrazine-3-yl, 69yrazine-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, py- rimidin-4-yl, pyrimidin-5-yl, 69yrazine-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, Ci-C6- alkoxy, Ci-C6-halogenalkoxy,C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl wherein the acyclic moieties of 10 are unsubstituted or substituted with identical or different groups R10a as defined and preferably defined herein, and wherein the carbocyclic, phenyl and heteroaryl moieties of R10 are unsubstituted or substituted with identical or different 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 , CrC5-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, CrC5-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl, 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 cycloalkyl moieties of R10 are unsubstituted or substituted with identical or different groups R10 as defined and preferably defined herein.
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 Ci-Ce-alkylthio.
According to one embodiment thereof R10b is independently selected from halogen, CN , C1-C4- alkyl, Ci-C4-alkoxy, CrC4-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 invention, 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 imgf000071_0001
Figure imgf000072_0001
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 heteroaromatic ring; wherein the heterocyclic or heteroaromatic ring contains 1 , 2, 3 or 4 heteroatoms se- lected from N, O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci- C4-halogenalkyl and SC Ph, 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 S02; 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 as defined below.
RN is the substituent of the heteroatom NRN 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-haloalkyl and S02Ph, 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-haloalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl substituents. In one particular embodiment, 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 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, CrC6-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, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-halogen- alkoxy, 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, C1-C4- halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloal- kyl, 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, R11 is H, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-Ce-alkoxy or , Ci-C6-halogenalkoxy, in particular H, CH3, Et, CHF2, OCH3, OCHF2, OCF3, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
According to another embodiment of formula I, R11 is hydrogen.
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 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 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, 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.
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, Ch C CH.
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, OCHCI2 or OCH2CI, in particular OCF3, OCH F2, 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 R11b, 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 hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and Ca-Ce-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 R11b as defined below.
According to still another embodiment of formula I, R11 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.
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, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-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-Cl2-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
R11b 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 R11b 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 is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-CI2-cyclopropyl and halogenmethoxy.
According to still another embodiment thereof R11b 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 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- CI-, 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 P35-301 corresponds to one particular embodiment of the invention, wherein P35-1 to P35-301 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 imgf000077_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
Figure imgf000081_0001
Figure imgf000082_0001
Particular embodiments of the compounds I are the following compounds: I.A, I.B, I.C, I.D, I.E, I.F, I.G, I.I, I.J, I.K, I.L. In these formulae, the substituents R4, R9 and R10 are independently as defined in claim 1 or referably defined below:
Figure imgf000082_0002
I.B I.C
Figure imgf000082_0003
I.D
Figure imgf000083_0001
Figure imgf000083_0002
Figure imgf000083_0003
I.L
In particular with a view to their use, according to one embodiment, preference is given to the compounds of the formulae I .A, I.B, I.C, I.D, I.E, I.F, I.G, I.H, I.I, I.J, I.K and I.L that are compiled in the Tables 1-1 to 1 -6, Tables 2-1 to 2-6, Tables 3-1 to 3-6, Tables 4-1 to 4-6, Tables 5-1 to 5- 6, Tables 6-1 to 6-6, Tables 7-1 to 7-6, Tables 8-1 to 8-6, Tables 9-1 to 9-6, Tables 10-1 to 10-6, Tables 1 1-1 to 1 1-6 and Tables 12-1 to 12-6. 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 I.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.A.1 -1.A-1 to I.A.1-1.A-246).
Table 1-2 Compounds of the formula I.A in which R9 is CHF2 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.A.1 -2.A-1 to I.A.1-2.A-246). Table 1-3 Compounds of the formula I.A in which R9 is C≡CH 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.A.1 -3.A-1 to I.A.1-3.A-246).
Table 1-4 Compounds of the formula I.A in which Rs is Br and the meaning for the combina- tion of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I.A.1 -4.A-1 to I.A.1-4.A-246).
Table 1-5 Compounds of the formula I.A in which R9 is OCH3 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.A.1 -5.A-1 to I.A.1-5.A-246).
Table 1-6 Compounds of the formula I.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 I.A.1-6.A-1 to I.A.1-6.A-246).
Table 2-1 Compounds of the formula I.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 I.B.2-1.A-1 to I.B.2-1.A-246).
Table 2-2 Compounds of the formula I.B in which R9 is CHF2 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.B.2-2.A-1 to I.B.2-2.A-246).
Table 2-3 Compounds of the formula I.B in which R9 is C=CH and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I.B.2-3.A-1 to I.B.2-3.A-246).
Table 2-4 Compounds of the formula I.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 I.B.2-4.A-1 to I.B.2-4.A-246).
Table 2-5 Compounds of the formula I.B in which R9 is OCH3 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.B.2-5.A-1 to I.B.2-5.A-246).
Table 2-6 Compounds of the formula I.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 I.B.2-6.A-1 to I.B.2-6.A-246).
Table 3-1 Compounds of the formula I.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 I.C.3-1.A-1 to I.C.3-1.A-246).
Table 3-2 Compounds of the formula I.C in which R9 is CHF2 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I.C.3-2.A-1 to I.C.3-2.A-246).
Table 3-3 Compounds of the formula I.C in which R9 is C≡CH 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.C.3-3.A-1 to I.C.3-3.A-246). Table 3-4 Compounds of the formula I.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 I.C.3-4.A-1 to I.C.3-4.A-246).
Table 3-5 Compounds of the formula I.C in which R9 is OCH3 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I.C.3-5.A-1 to I.C.3-5.A-246).
Table 3-6 Compounds of the formula I.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 I.C.3-6.A-1 to I.C.3-6.A-246).
Table 4-1 Compounds of the formula I. 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 I.D.4-1.A-1 to I.D.4-1.A-246).
Table 4-2 Compounds of the formula I.D in which R9 is CHF2 and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds I.D.4-2.A-1 to I.D.4-2.A-246).
Table 4-3 Compounds of the formula I.D in which R9 is C≡CH 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.D.4-3.A-1 to I.D.4-3.A-246).
Table 4-4 Compounds of the formula I.D in which R9 is Br and the meaning for the combina- tion of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I.D.4-4.A-1 to I.D.4-4.A-246).
Table 4-5 Compounds of the formula I.D in which R9 is OCH3 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.D.4-5.A-1 to I.D.4-5.A-246).
Table 4-6 Compounds of the formula I.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 I.D.4-6.A-1 to I.D.4-6.A-246).
Table 5-1 Compounds of the formula I.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 I.E.5-1.A-1 to I.E.5-1.A-246).
Table 5-2 Compounds of the formula I.E in which R9 is CHF2 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.E.5-2.A-1 to I.E.5-2.A-246).
Table 5-3 Compounds of the formula I.E in which R9 is C≡CH and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I.E.5-3.A-1 to I.E.5-3.A-246).
Table 5-4 Compounds of the formula I.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 I.E.5-4.A-1 to I.E.5-4.A-246). Table 5-5 Compounds of the formula I.E in which R9 is OCH3 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.E.5-5.A-1 to I.E.5-5.A-246).
Table 5-6 Compounds of the formula I.E in which Rs 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 I.E.5-6.A-1 to I.E.5-6.A-246).
Table 6-1 Compounds of the formula I.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.F.6-1 .A-1 to I.F.6-1.A-246).
Table 6-2 Compounds of the formula I.F in which R9 is CHF2 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.F.6-2.A-1 to I.F.6-2.A-246).
Table 6-3 Compounds of the formula I.F in which R9 is C≡CH and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds I.F.6-3.A-1 to I.F.6-3.A-246).
Table 6-4 Compounds of the formula I.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 I.F.6-4.A-1 to I.F.6-4.A-246).
Table 6-5 Compounds of the formula I.F in which R9 is OCH3 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I.F.6-5.A-1 to I.F.6-5.A-246).
Table 6-6 Compounds of the formula I.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 I.F.6-6.A-1 to I.F.6-6.A-246).
Table 7-1 Compounds of the formula I.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 I.G.7-1.A-1 to I.G.7-1.A-246).
Table 7-2 Compounds of the formula I.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 Ta- ble A (compounds I.G.7-2.A-1 to I.G.7-2.A-246).
Table 7-3 Compounds of the formula I.G in which R9 is C=CH 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.G.7-3.A-1 to I.G.7-3.A-246).
Table 7-4 Compounds of the formula I.G in which R9 is Br and the meaning for the combina- tion of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I.G.7-4.A-1 to I.G.7-4.A-246).
Table 7-5 Compounds of the formula I.G in which R9 is OCH3 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.G.7-5.A-1 to I.G.7-5.A-246). Table 7-6 Compounds of the formula I.G 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 I.G.7-6.A-1 to I.G.7-6.A-246). Table 8-1 Compounds of the formula I.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 I.H.8-1.A-1 to I.H.8-1.A-246).
Table 8-2 Compounds of the formula I.H in which R9 is CHF2 and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds I.H.8-2.A-1 to I.H.8-2.A-246).
Table 8-3 Compounds of the formula I.H in which R9 is C≡CH 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.H.8-3.A-1 to I.H.8-3.A-246).
Table 8-4 Compounds of the formula I.H in which R9 is Br and the meaning for the combina- tion of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I.H.8-4.A-1 to I.H.8-4.A-246).
Table 8-5 Compounds of the formula I.H in which R9 is OCH3 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.H.8-5.A-1 to I.H.8-5.A-246).
Table 8-6 Compounds of the formula I.H 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 I.H.8-6.A-1 to I.H.8-6.A-246).
Table 9-1 Compounds of the formula I.I 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 1.1.9-1.A-1 to 1.1.9-1.A-246).
Table 9-2 Compounds of the formula I.I 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.I.9-2.A-1 to 1.1.9-2.A-246).
Table 9-3 Compounds of the formula I.I in which R9 is C≡CH and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I.I.9-3.A-1 to I.I.9-3.A-246).
Table 9-4 Compounds of the formula I.I in which R9 is Br 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.I.9-4.A-1 to 1.1.9-4.A-246).
Table 9-5 Compounds of the formula I.I in which R9 is OCH3 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.I.9-5.A-1 to I.I.9-5.A-246).
Table 9-6 Compounds of the formula I.I 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 I.I.9-6.A-1 to I.I.9-6.A-246).
Table 10-1 Compounds of the formula I.J in which R9 is 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.J.10-1.A-1 to I.J.10-1.A-246).
Table 10-2 Compounds of the formula I.J in which R9 is CHF2 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.J.10-2.A-1 to I.J.10-2.A-246).
Table 10-3 Compounds of the formula I.J in which R9 is C≡CH and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds I.J.10-3.A-1 to I.J.10-3.A-246).
Table 0-4 Compounds of the formula I.J 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.J.10-4.A-1 to I.J.10-4.A-246).
Table 10-5 Compounds of the formula I.J in which R9 is OCH3 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I.J.10-5.A-1 to I.J.10-5.A-246).
Table 10-6 Compounds of the formula I.J 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 I.J.10-6.A-1 to I.J.10-6.A-246).
Table 1 1 -1 Compounds of the formula I. K in which Rs 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.K.1 1-1.A-1 to I. K.1 1-1.A-246).
Table 1 1 -2 Compounds of the formula I.K in which R9 is CHF2 and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds I. K.1 1-2.A-1 to I. K.1 1-2.A-246).
Table 1 1 -3 Compounds of the formula I.K in which R9 is C≡CH 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. K.1 1-3.A-1 to I. K.1 1-3.A-246).
Table 1 1 -4 Compounds of the formula I.K in which R9 is Br and the meaning for the combina- tion of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I.K.1 1-4.A-1 to I. K.1 1-4.A-246).
Table 1 1 -5 Compounds of the formula I.K in which R9 is OCH3 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.K.1 1-5.A-1 to I.K.1 1-5.A-246).
Table 1 1 -6 Compounds of the formula I.K 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 I.K.1 1-6.A-1 to I.K.1 1-6.A-246).
Table12- 1 Compounds of the formula I.L 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.L.1 1-1.A-1 to I.L.1 1-1.A-246).
Table12- 2 Compounds of the formula I.L 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.L.1 1-2.A-1 to I.L.1 1-2.A-246).
Table12- 3 Compounds of the formula I.L in which R9 is C≡CH 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.L.1 1-3.A-1 to I.L.1 1-3.A-246).
Table12- 4 Compounds of the formula I.L 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.L.1 1-4.A-1 to I.L.1 1-4.A-246).
Table12- 5 Compounds of the formula I.L in which R9 is OCH3 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.L.1 1-5.A-1 to I.L.1 1-5.A-246).
Table12- 6 Compounds of the formula I.L 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 I.L.1 1-6.A-1 to I.L.11 -6.A-246).
Particular embodiments of the compounds X are the following compounds X.A -X.L. In these formulae, the substituents R4, R78, o, R9, R10 are independently as defined in claim 1 or preferabl defined herein:
Figure imgf000089_0001
XA
xc
Figure imgf000089_0002
XD
Figure imgf000090_0001
Figure imgf000090_0002
Figure imgf000090_0003
Figure imgf000090_0004
XL
In particular with a view to their use, according to one embodiment, preference is given to the compounds of the formulae X.A, X.B, X.C, X.D, X.E, X.F, X.G, X.H, X.I, X.J, X.K and X.L that are compiled in the Tables 1-1 to 1-6, Tables 2-1 to 2-6, Tables 3-1 to 3-6, Tables 4-1 to 4-6, Tables 5-1 to 5-6, Tables 6-1 to 6-6, Tables 7-1 to 7-6, Tables 8-1 to 8-6, Tables 9-1 to 9-6, Tables 10-1 to 10-6, Taboes 1 1-1 to 1 1 -6 and Tables 12-1 to 12-6. 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.A in which R9 is CH3 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.A.1 -1.A-1 to X.A.1-1 .A-246). Table 1-2 Compounds of the formula X.A in which R9 is CHF2 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.A.1 -2.A-1 to X.A.1-2.A-246).
Table 1-3 Compounds of the formula X.A in which R9 is C≡CH and the meaning for the com- bination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.A.1 -3.A-1 to X.A.1-3.A-246).
Table 1-4 Compounds of the formula X.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.A.1-4.A-1 to X.A.1-4.A-246).
Table 1-5 Compounds of the formula X.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.A.1 -5.A-1 to X.A.1-5.A-246).
Table 1-6 Compounds of the formula X.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.A.1-6.A-1 to X.A.1-6.A-246).
Table 2-1 Compounds of the formula X.B in which R9 is CH3 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.B.2-1.A-1 to X.B.2-1 .A-246).
Table 2-2 Compounds of the formula X.B in which R9 is CHF2 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.B.2-2.A-1 to X.B.2-2.A-246).
Table 2-3 Compounds of the formula X.B in which R9 is C≡CH 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.B.2-3.A-1 to X.B.2-3.A-246).
Table 2-4 Compounds of the formula X.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.B.2-4.A-1 to X.B.2-4. A-246).
Table 2-5 Compounds of the formula X.B in which R9 is OCH3 and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.B.2-5.A-1 to X.B.2-5.A-246).
Table 2-6 Compounds of the formula X.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.B.2-6.A-1 to X.B.2-6. A-246).
Table 3-1 Compounds of the formula X.C in which R9 is CH3 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.C.3-1 .A-1 to X.C.3-1.A-246).
Table 3-2 Compounds of the formula X.C in which R9 is CHF2 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.C.3-2.A-1 to X.C.3-2.A-246). Table 3-3 Compounds of the formula X.C in which R9 is C≡CH 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.C.3-3.A-1 to X.C.3-3.A-246).
Table 3-4 Compounds of the formula X.C in which Rs is Br and the meaning for the combina- tion of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X.C.3-4.A-1 to X.C.3-4.A-246).
Table 3-5 Compounds of the formula X.C in which R9 is OCH3 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.C.3-5.A-1 to X.C.3-5.A-246).
Table 3-6 Compounds of the formula X.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.C.3-6.A-1 to X.C.3-6.A-246).
Table 4-1 Compounds of the formula X.D in which R9 is CH3 and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.D.4-1 .A-1 to X.D.4-1.A-246).
Table 4-2 Compounds of the formula X.D in which R9 is CHF2 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.D.4-2.A-1 to X.D.4-2.A-246).
Table 4-3 Compounds of the formula X.D in which R9 is C=CH and the meaning for the com- bination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.D.4-3.A-1 to X.D.4-3.A-246).
Table 4-4 Compounds of the formula X.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.D.4-4.A-1 to X.D.4-4.A-246).
Table 4-5 Compounds of the formula X.D in which R9 is OCH3 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.D.4-5.A-1 to X.D.4-5.A-246).
Table 4-6 Compounds of the formula X.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.D.4-6.A-1 to X.D.4-6.A-246).
Table 5-1 Compounds of the formula X.E in which R9 is CH3 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.E.5-1.A-1 to X.E.5-1 .A-246).
Table 5-2 Compounds of the formula X.E in which R9 is CHF2 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.E.5-2.A-1 to X.E.5-2.A-246).
Table 5-3 Compounds of the formula X.E in which R9 is C≡CH 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.E.5-3.A-1 to X.E.5-3.A-246). Table 5-4 Compounds of the formula X.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.E.5-4.A-1 to X.E.5-4.A-246).
Table 5-5 Compounds of the formula X.E in which R9 is OCH3 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.E.5-5.A-1 to X.E.5-5.A-246).
Table 5-6 Compounds of the formula X.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.E.5-6.A-1 to X.E.5-6.A-246).
Table 6-1 Compounds of the formula X.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.F.6-1 .A-1 to X.F.6-1 .A-246).
Table 6-2 Compounds of the formula X.F in which R9 is CHF2 and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.F.6-2.A-1 to X.F.6-2.A-246).
Table 6-3 Compounds of the formula X.F in which R9 is C≡CH 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.F.6-3.A-1 to X.F.6-3.A-246).
Table 6-4 Compounds of the formula X.F in which R9 is Br and the meaning for the combina- tion of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X.F.6-4.A-1 to X.F.6-4.A-246).
Table 6-5 Compounds of the formula X.F in which R9 is OCH3 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.F.6-5.A-1 to X.F.6-5.A-246).
Table 6-6 Compounds of the formula X.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.F.6-6.A-1 to X.F.6-6.A-246).
Table 7-1 Compounds of the formula X.G in which R9 is CH3 and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.G.7-1.A-1 to X.G.7-1.A-246).
Table 7-2 Compounds of the formula X.G in which R9 is CHF2 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.G.7-2.A-1 to X.G.7-2.A-246).
Table 7-3 Compounds of the formula X.G in which R9 is C≡CH and the meaning for the com- bination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.G.7-3.A-1 to X.G.7-3.A-246).
Table 7-4 Compounds of the formula X.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.G.7-4.A-1 to X.G.7-4.A-246). Table 7-5 Compounds of the formula X.G in which R9 is OCH3 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.G.7-5.A-1 to X.G.7-5.A-246).
Table 7-6 Compounds of the formula X.G 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.G.7-6.A-1 to X.G.7-6.A-246).
Table 8-1 Compounds of the formula X.H in which R9 is CH3 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.H.8-1 .A-1 to X.H.8-1.A-246).
Table 8-2 Compounds of the formula X.H in which R9 is CHF2 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.H.8-2.A-1 to X.H.8-2.A-246).
Table 8-3 Compounds of the formula X.H in which R9 is C≡CH and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.H.8-3.A-1 to X.H.8-3.A-246).
Table 8-4 Compounds of the formula X.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.H.8-4.A-1 to X.H.8-4.A-246).
Table 8-5 Compounds of the formula X.H in which R9 is OCH3 and the meaning for the com- bination of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.H.8-5.A-1 to X.H.8-5.A-246).
Table 8-6 Compounds of the formula X.H 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.H.8-6.A-1 to X.H.8-6.A-246).
Table 9-1 Compounds of the formula X.I 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.X.9-1.A-1 to X.X.9-1 .A-246).
Table 9-2 Compounds of the formula X.I in which R9 is CHF2 and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.X.9-2.A-1 to X.X.9-2.A-246).
Table 9-3 Compounds of the formula X.I in which R9 is C=CH 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.X.9-3.A-1 to X.X.9-3.A-246).
Table 9-4 Compounds of the formula X.I in which R9 is Br and the meaning for the combina- tion of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X.X.9-4.A-1 to X.X.9-4.A-246).
Table 9-5 Compounds of the formula X.I in which R9 is OCH3 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.X.9-5.A-1 to X.X.9-5.A-246). Table 9-6 Compounds of the formula X.I 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.X.9-6.A-1 to X.X.9-6.A-246).
Table 10-1 Compounds of the formula X.J in which R9 is CH3 and the meaning for the combina- tion of R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X.J.10-1.A-1 to X.J.10-1.A-246).
Table 10-2 Compounds of the formula X.J in which R9 is CHF2 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.J.10-2.A-1 to X.J.10-2.A-246).
Table 10-3 Compounds of the formula X.J in which R9 is C≡CH 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.J.10-3.A-1 to X.J.10-3.A-246).
Table 10-4 Compounds of the formula X.J 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.J.10-4.A-1 to X.J.10-4.A-246).
Table 10-5 Compounds of the formula X.J in which R9 is OCH3 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.J.10-5.A-1 to X.J.10-5.A-246).
Table 10-6 Compounds of the formula X.J 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.J.10-6.A-1 to X.J.10-6.A-246).
Table 1 1 -1 Compounds of the formula X.K in which R9 is CH3 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.K.1 1-1.A-1 to X.K.1 1-1.A-246).
Table 1 1 -2 Compounds of the formula X.K in which R9 is CHF2 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.K.1 1-2.A-1 to X.K.1 1-2.A-246).
Table 1 1 -3 Compounds of the formula X.K in which R9 is C≡CH and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.K.1 1-3.A-1 to X.K.1 1-3.A-246).
Table 1 1 -4 Compounds of the formula X.K 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.K.1 1 -4.A-1 to X.K.11-4.A-246).
Table 1 1 -5 Compounds of the formula X.K in which R9 is OCH3 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.K.1 1-5.A-1 to X.K.1 1-5.A-246).
Table 1 1 -6 Compounds of the formula X.K 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.K.1 1-6.A-1 to X.K.1 1-6.A-246). Table 12- 1 Compounds of the formula X.L 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.L.12-1.A-1 to X.L.12-1.A-246).
Table 12- 2 Compounds of the formula X.L in which R9 is CHF2 and the meaning for the combi- nation of R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X.L.12-2.A-1 to X.L.12-2.A-246).
Table 12- 3 Compounds of the formula X.L in which R9 is C≡CH 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.L.12-3.A-1 to X.L.12-3.A-246).
Table 12- 4 Compounds of the formula X.L 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.L.12-4.A-1 to X.L.12-4.A-246).
Table 12- 5 Compounds of the formula X.L in which R9 is OCH3 and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Ta- ble A (compounds X.L.12-5.A-1 to X.L.12-5.A-246).
Table 12- 6 Compounds of the formula X.L 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.L.12-6.A-1 to X.L.12-6. A-246). Table A
Figure imgf000096_0002
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Figure imgf000100_0001
Figure imgf000101_0001
Figure imgf000102_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 ob- tained 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 herbi- cides 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 nematodes, 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 capa- ble 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); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A brassico/a or brassi- cae), sugar beets (A tenuis), fruits, rice, soybeans, potatoes (e. g. A solani or A alternata), tomatoes (e. g. A solani OK A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A //yfr (anthracnose) on wheat and A horde/ on barley; Bipolar/s and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (Z7. maydis) or Northern leaf blight (.?. zeicola) on corn, e. g. spot blotch (.?. sorokin- Λ2/7.2) on cereals and e. g. 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. t///77/'(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 ox C. k/kuchi/) 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: Anthracnose 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. pyn), 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. solani (f. 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- e//a spp. on cereals (e. g. G. zeae) and rice (e. g. G. fujikuror. Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochlioboius) on corn, cereals and rice; Hemi/eiaspp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoll) (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. phaseoll, 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. capsicl), 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 mildew) 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. cubensis on cucurbits or P. hum/lion 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 stolon/ fer(b\ac 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. rolfsii or 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 (s n. Erysiphe) necator (powdery mildew, ana- morph: 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. reilianar. 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. Phaeosphaeria] 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. tritici {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. appendicu/atus, 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; Venturia 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 harm- ful 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 Ophiostom a spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp:, Basidiomycetes such as Coni- ophora spp., 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 fur- niture 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 pro- cessed 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 iden- tified 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 com- prising 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), capsules (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; gly- cols; 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 amphoteric 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 sul- fates 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, esters, 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 al- cohols, 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 ox- ide, 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 them- selves, 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 phthalocyanine 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% dispersants (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 dimethyl 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% colorants. 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 treatment (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 ap- plied 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 pathogens, 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 facili- tate 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 reduce 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 invention 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 ap- propriate. Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, 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 option- ally 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 combinations 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. .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-AA[2-[(1 ,4-dimethyl-5-phenyl- pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), 1-[2-[[1 -(4-chlorophenyi)py- razol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1 .25), (2^2 )-5-[1 -(2,4-di- chlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-/V13-dimethyl-pent-3-enamide (A.1.34), (Z 2_r)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino- V,3-dimethyl-pent-3-enamide (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-[(2 )-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.1.11), 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)metha- 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. ), 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. .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.1.11 ), 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 . 6);
- 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.3J);
- 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-pipendyl]-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-carboxami (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 (I.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-tnmethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl forma- midine (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, padobutrazol, 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 312337-48-6); 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- oxo-2H-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-methy ethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]_imethyl]amino]-benzoic 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-trifluoromethy phenoxy)-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, 11.3 , II.4, II.5, II.6, II.7, II.8 and II.9
Figure imgf000122_0001
Figure imgf000122_0002
Figure imgf000122_0003
1 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1-cyclohexyl-5-pentafluorphenyloxy-14-[ ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1);
2 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;
3 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 /^imidazole-amine, (2£)-1-[(6-chloropyridin-3-yl)me- thyl]-A/-nitro-2-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, flupyradifurone, triflumezopyrim;
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 modulatorspymetrozine, flonicamid, 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; 4 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;
5 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen;
6 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-11 -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 firmus, 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-m 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-met yl-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- methylt io-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- ,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-met yl-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 -( ,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-carboxamide, tyclopyrazoflor; 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, N- [4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2-pentafluoroethyl)-
4-(trifluoromethyl)-1 pyrazole-S-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-(trifluorom thyl)-4 isoxazol-3-yl]-AA[(4 ^-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzam^ 4-[5- (3,5-dichloro-4-fluoro-phenyl)-5-(trifluorom
isoxazolidin-4-yl]-2-methyl-benzamide; AA[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-pen^
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 03/11853; 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 11/77514; 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 13/116251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454,
WO 12/165511 , WO 11/081 174, 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 I I in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.1 1 ), (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 com- pounds (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 Delta14-reductase inhibitors in group B), more preferably selected from compounds (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 (I.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)-5-fluoro-3-methyl-3-(2-pyridyl)-4H-isoquino- line (I-2)
Step 1.1 1-(2-fluorophenyl)-2-(2-pyridyl)propan-2-ol To a solution 1 ,29 g (0,053 mol) magnesium in ether, one drop of bromo was added. Then, a solution of 5,0 g (0,026 mol) 2-fluorbenzyl bromide in 25 ml_ ether was added slowly dropwise. After 2h stirring at room temperature, the mixture was cooled to 0°C and a solution of 2,24 g (0,019 mol) 2-acetylpyridine in 20 ml_ ether was added. The reaction mixture was stirred over- night, then it was cooled to 0 °C and quenched with a sat. NhUCI solution. The aqueous phase was extracted 3 times with MTBE, the combined of organic phases was washed with a sat. NH4CI solution, water and sat. NaCI solution, dried with Na2S04 and concentrated. The residues was purified via MPLC chromatography with water/Acetonitrile mixture to yield 2,05 g (48%) of the title compound as a light yellow oil.
1H-NMR (CDC , δ in ppm): 9,8 (d, 1 H); 9,5 (d, 1 H); 8,8 (dd, 1 H); 7,3-7,2 (m, 2H); 7,0 (m, 3H);
3.3 (d, 1 H); 3,1 (d, 1 H); 1 ,6 (s, 3H).
*HPLC-MS: Rt = 0,672 min; m++H = 232,1
Step 1.2 1-(5,6-dimethyl-3-pyridyl)-5-fluoro-3-methyl-3-(2-pyridyl)-4H-isoquinoline
13,0 g of trifluoromethane sulfonic acid was added dropwise to a mixture of 0,91 g (7,0 mmol) 2,3-dimethylpyridine-5-carbonitrile and 2,0 g (9,0 mmol) 1-(2-fluorophenyl)-2-(2-pyridyl)propan- 2-ol in 40 ml dichloroethane at 0 - 5°C. After 2 days 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/acetonitrile mixtures to yield 0,1 1 g (4 %) of the title compound as a light yellow oil.
1H-NMR (CDCI3, δ in ppm): 8,7 (s, 1 H); 8,6 (d, 1 H); 7,8 (m, 2H); 7,6 (m, 1 H); 7,3-7,1 (m, 4H);
3.4 (d, 1 H); 3,3, (d, 1 H); 2,6 (s, 3H); 2,4 (s, 3H); 1 ,6 (s, 6H).
*HPLC-MS: Rt = 0,743 min; M++H = 346,1
Example 2 Synthesis of 3-(3,3-dichloroallyl)-1-(5,6-dimethyl-3-pyridyl)-5-fluoro-3-methyl-4H-iso- quinoline (I-3)
Step 1.1 tert-butyl 3-(2,2-dichlorocyclopropyl)-2-(2-fluorophenyl)-3-oxo-propanoate
To a solution of tert-butyl 2-(2-fluorophenyl)acetate (13,5 g, 0,0645 mol) in THF (150 mL) was added n-BuLi (26 mL, 0,0645 mol) dropwise under N2 at -78°C, the solution was stirred for 0,5 h, 2,2-dichlorocyclopropanecarbonyl chloride (11 ,5 g, 0,0645 mol) in THF was added dropwise at -78°C under N2, the mixture was stirred for 2 h at -78°C. The reaction mixture was quenched with aq. NH4CI (100 mL) and extracted with MTBE (150 mL), dried over Na2SC>4 and concentrated, the residue was purified by column (PE:EtOAc=100:1) to give the tittle compound (10,7 g, 48,6 %).
Stepl .2 1-(2,2-dichlorocyclopropyl)-2-(2-fluorophenyl)ethanone
To a solution of tert-butyl 3-(2,2-dichlorocyclopropyl)-2-(2-fluorophenyl)-3-oxo-propanoate in MeCN\H20 (150 mL\6 mL) was added l2 (15,7 g, 0,062 mol) under N2, the mixture was heated to 105 °C for 2 h. The reaction mixture was quenched with aq. Na2SC>3 (100 mL) and extracted with MTBE (100 mL), dried over Na2S04 and concentrated, the residue was purified by column (PE:EtOAc=100:1) to give the tittle compound (4,24 g, 55.4 %) 1H-NMR (CDCI3, δ in ppm): 1 ,72 (dd, J=9,41 , 7,03 Hz, 1 H); 2;09 (t, J=7,53 Hz, 1 H); 2.76 (dd, J=9,29, 8,16 Hz, 1 H); 3,90 (s, 2 H); 7,01 - 7,1 1 (m, 2 H); 7,14 - 7,30 (m, 2 H)
Step .3 2-(2,2-dichlorocyclopropyl)-1-(2-fluorophenyl)propan-2-ol
To a solution of 1-(2,2-dichlorocyclopropyl)-2-(2-fluorophenyl)ethanone (4,24 g, 0,0172 mol) in THF (100 mL) was added MeMgBr (8,6 mL, 0,0257 mol) dropwise at 0 oC under N2, the mixture was stirred for 2 h at 0 °C. The reaction mixture was quenched with aq. N H4CI (100 mL) and extracted with MTBE (100 mL), dried over Na2SC>4 and concentrated, the residue was purified by column (PE:EtOAc=30:1 ) to give the tittle compound (3.55 g, 79 %).
H-NMR (CDCI3, δ in ppm): 1 ,50 (dd, J=8,22, 3,70 Hz, 2 H); 1 ,60 - 1 ,68 (m, 2 H); 1 ,98 (s, 1 H); 3,00 (d, J=13,43 Hz, 1 H); 3,20 (d, J=13,43 Hz, 1 H); 6,97 - 7,09 (m, 3 H); 7,13 - 7,33 (m, 3 H)
Step .4 3-(3,3-dichloroallyl)-1-(5,6-dimethyl-3-pyridyl)-5-fluoro-3-methyl-4H-isoquinoline
2-(2,2-dichlorocyclopropyl)-1-(2-fluorophenyl)propan-2-ol (1.3 g, 5 mmol) and 5,6-dimethylpyri- dine-3-carbonitrile (0.65 g, 5 mmol) in 100 mL flask was added TfOH (8 mL) dropwise at 0 °C under N2, the mixture was stirred for 16 h. The reaction mixture was quenched with aq. NaHCC>3 (100 mL), extracted with EtOAc (100 mL), washed with brine (100 mL), dried over Na2S04 and concentrated, purified by column (PE:EtOAc=8:1 ) and then further purified by Pre-HPLC (acid) to give the tittle compound (100 mg, 5 %) as yellow oil and 3-(2,3-dichloro-2-methyl-propyl)-1- (5,6-dimethyl-3-pyridyl)-5-fluoro-3-methyl-4H-isoquinoline (I-4) (350 mg, 17.5) as yellow solid.
1H-NMR (CDC , δ in ppm): 8,4 (br s, 1 H); 7,6 (s, 1 H); 7,2-7,1 (m, 2H); 7,0 (dd, 1 H); 6,0 (td, 1 H); 2,8 (s, 2H); 2,5 (s, 3H); 2,4-2,3 (m, 2H); 2,2 (s, 3H); 1 ,3 (s, 3H)
*HPLC-MS: Rt = 0,971 min; M++H = 377;1
Example 2 Synthesis of 3-(3,3-dichloroallyl)-1-(5,6-dimethyl-3-pyridyl)-5-fluoro-3-methyl-4H-iso- quinoline (I-3) and 3-(2,3-dichloro-2-methyl-propyl)-1-(5,6-dimethyl-3-pyridyl)-5-fluoro-3-methyl- 4H-isoquinoline (I-4) Step 1.1 Synthesis tert-butyl 2-(2-fluorophenyl)acetate
To a solution of 2-(2-fluorophenyl)acetic acid (50 g, 0.325 mol) in 300 mL THF and 360 mL t- BuOH was added DMAP (20 g, 0.163 mol) and (Boc)20 (106 g, 0.487 mol) dropwise under N2 at 25 °C, the solution was heated to reflux for 16 h. The reaction mixture was concentrated, the residue was diluted with water (800 mL) and extracted with MTBE (500 mL), dried over Na2S04 and concentrated, the residue was purified by column (PE:EtOAc=200:1 ) to give the desired compound (56 g, 80 %).
!H-N M R (CDCb, δ in ppm): 1.48 (s, 9 H) 3.61 (s, 2 H) 7.04 - 7.17 (m, 2 H) 7.22 - 7.36 (m, 2 H)
Step 1.2 Synthesis of tert-butyl 3-(2,2-dichlorocyclopropyl)-2-(2-fluorophenyl)-3-oxo-propano- ate
The solution of tert-butyl 2-(2-fluorophenyl)acetate (13.5 g, 0.0645 mol) in THF (150 mL) was added n-BuLi (26 mL, 0.0645 mol) dropwise under N2 at -78 °C, the solution was stirred for 0.5 h, 2,2-dichlorocyclopropanecarbonyl chloride (1 1.5 g, 0.0645 mol) in THF was added drop- wise at -78 °C under N2, the mixture was stirred for 2 h at -78 °C. The reaction mixture was quenched with aq. NH4CI ( 00 mL) and extracted with MTBE (150 mL), dried over Na2SC>4 and concentrated, the residue was purified by column (PE:EtOAc=100: 1) to give the desired compound (10.7 g, 48.6 %). Step 1.3 Synthesis of 1-(2,2-dichlorocyclopropyl)-2-(2-fluorophenyl)ethanone
The solution of tert-butyl 3-(2,2-dichlorocyclopropyl)-2-(2-fluorophenyl)-3-oxo-propanoate (10.7 g, 0.031 mol) in MeCN\H20 (150 mL\6 mL) was added l2 (15.7 g, 0.062 mol) under N2, the mixture was heated to 105 °C for 2 h. The reaction mixture was quenched with aq. Na2SC>3 (100 mL) and extracted with MTBE (100 mL), dried over Na2SC>4 and concentrated, the resi- due was purified by column (PE:EtOAc=100:1 ) to give the desired compound (4.24 g, 55.4 %). 1 H-NMR (CDCI3, δ in ppm): 1 .72 (dd, J=9.41 , 7.03 Hz, 1 H) 2.09 (t, J=7.53 Hz, 1 H) 2.76 (dd,
J=9.29, 8.16 Hz, 1 H) 3.90 (s, 2 H) 7.01 - 7.1 1 (m, 2 H) 7.14 - 7.30 (m, 2 H)
Step 1.4 Synthesis of 2-(2,2-dichlorocyclopropyl)-1 -(2-fluorophenyl)propan-2-ol
The solution of 1-(2,2-dichlorocyclopropyl)-2-(2-fluorophenyl)ethanone (4.24 g, 0.0172 mol) in THF (100 mL) was added MeMgBr (8.6 mL, 0.0257 mol) dropwise at 0 oC under N2, the mixture was stirred for 2 h at 0 oC. The reaction mixture was quenched with aq. NH4CI (100 mL) and extracted with MTBE (100 mL), dried over Na2S04 and concentrated, the residue was purified by column (PE:EtOAc=30:1 ) to give the desired compound (3.55 g, 79 %).
1 H-NMR (CDCI3, δ in ppm): 1 .50 (dd, J=8.22, 3.70 Hz, 2 H) 1.60 - 1.68 (m, 2 H) 1.98 (s, 1 H) 3.00 (d, J=13.43 Hz, 1 H), 3.20 (d, J=13.43 Hz, 1 H) 6.97 - 7.09 (m, 3 H) 7.13 - 7.33 (m, 3 H)
Step 1.4 Synthesis of 3-(3,3-dichloroallyl)-1-(5,6-dimethyl-3-pyridyl)-5-fluoro-3-methyl-4H-iso- quinoline (I-3) and 3-(2,3-dichloro-2-methyl-propyl)-1 -(5,6-dimethyl-3-pyridyl)-5-fluoro-3-me- thyl-4H-isoquinoline (I-4)
2-(2,2-dichlorocyclopropyl)-1-(2-fluorophenyl)propan-2-ol (1 .3 g, 5 mmol) and 5,6-dimethylpyri- dine-3-carbonitrile (0.65 g, 5 mmol) in 100 mL flask was added TfOH (8 mL) dropwise at 0 °C under N2, the mixture was stirred for 16 h. The reaction mixture was quenched with aq. Na- HCO3 (100 mL), extracted with EtOAc (100 mL), washed with brine (100 mL), dried over Na2S04 and concentrated, purified by column (PE:EtOAc=8:1 ) and then further purified by
Pre-HPLC (acid) to give I-3 (100 mg, 5 %) as yellow oil and I-4 (350 mg, 17.5) as yellow solid.
I-3, 1 H-NMR (CDCI3, δ in ppm): 8,4 (br s, 1 H); 7,6 (s, 1 H); 7,2-7,1 (m, 2H); 7,0 (dd, 1 H); 6,0 (td, 1 H); 2,8 (s, 2H); 2,5 (s, 3H); 2,4-2,3 (m, 2H); 2,2 (s, 3H); 1 ,3 (s, 3H)
*HPLC-MS: Rt = 0,971 min; M++H = 377;1
I-4, 1 H-NMR (CDCI3, δ in ppm): 8,4 (s, 1 H); 7,5 (s, 1 H); 7,3-7,2 (m, 2H); 7,1 (m, 2H); 5,4 (s, 2H); 3,1 (td, 2H); 3,0 (td, 1 H); 2,6 (d, 1 H); 2,5 (s, 3H); 2,3 (s, 3H), 1 ,5 (s, 3H)
Figure imgf000134_0001
Table I:
Figure imgf000134_0002
Figure imgf000135_0001
HPLC-MS: HPLC-column Kinetex XB C181,7μ (50x2,1 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 1-1 , I-2, I-3, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20 and I- 21 respectively, showed up to at most 13 % 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 ex- amples I-2, I-3, I-5, I-6, I-7, I-8, 1-10, 1-1 1 , 1-13, 1-14, 1-15, 1-17, 1-19 and 1-21 respectively, showed up to at most 12 % growth of the pathogen.
Example 3 - Activity against rice blast Pyriculana 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 examples 1-1 , I-2, I-3, 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 and 1-21 respectively, showed up to at most 12 % growth of the pathogen. 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.
In this test, the samples which had been treated with 31 ppm of the active substance from ex- amples I-3, I-5, I-6, I-8, I-9, 1-10, 1-1 1 , 1-13, 1-14, 1-15, 1-17, 1-18, 1-19 and 1-21 respectively, showed up to at most 5 % 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 I-9, 1-10, 1-1 1 , 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-21 , I-22, 1-23 and Ir respectively, showed up to at most 3 % growth of the pathogen whereas the untreated plants were 90% infected.
Example 2 - 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.
In this test, the samples which had been treated with 250 ppm of the active substance from examples I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-21 , I-22, I-23 and I-24 respectively, showed up to at most 15 % growth of the pathogen whereas the untreated plants were 90% 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 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 imgf000138_0001
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) solvent-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 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.
Disease
Compound Structure (%) at
63ppm
State of the
art 50
^^^^^^^^^^^^
1-1 33
I-3 4
Figure imgf000140_0001
Example 2 - Control of culm rot on pearl millet caused by Fusarium culmonim
Pot-grown pearl millet seedlings were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. Seven days later the plants were inoculated with a spore suspension of Fusarium culmorum in an aqueous biomalt or DOB media solution. Then the trial plants were immediately transferred to a humid chamber. After 6 days at 23-25°C and a relative humidity close to 100 % the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
Disease (%) at
Compound Structure 63ppm
State of the
art 88
I-2 56
Figure imgf000141_0001
Example 3 - Preventative fungicidal control of apple scrab Venturia inaequalis
Young seedlings of apple 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 solution containing the spore suspension of Venturia inaequalis. Then the plants were immediately transferred to a humid chamber. After 1 day at 22 to 24· C and a relative humidity close to 100 % the plants were transferred to a chamber with 22- 24°C and a relative humidity of 70%. After 12 days the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
Figure imgf000141_0002
Figure imgf000142_0001

Claims

Claims
1. Compounds of formula I
Figure imgf000143_0001
wherein
R1 is in each case independently selected from H, halogen, OH, CN, NO2, SH, N H2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C5-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:
R a halogen , OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C -hal- ogenalkoxy, 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, CrC4-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 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 the substituents as defined for R1, wherein the possible substituents for R2 are R2a and R2 , respectively, which correspond to R1a and R1b, respectively;
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-halogen- alkoxy, CH(=0),
Figure imgf000144_0001
C(=0)N H(Ci-C6-alkyl),
Figure imgf000144_0002
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 par- tially 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 , N H2, N H(C C4-alkyl), N(d-C -al- kyl)2, N H-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-cycloal- kyl, 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, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2,
Figure imgf000144_0003
alkyl),
Figure imgf000144_0004
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-Ce-alkyl), C(=0)N H(Ci-C3-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, NH(Ci-C4-al- kyl), N(CrC4-alkyl)2, N
Figure imgf000144_0005
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:
R b halogen, OH , CN, N02, SH, NH2, NH(C C4-alkyl), N(C C4-alkyl)2, N H(C(=0)Ci-C4- alkyl),
Figure imgf000144_0006
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 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 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 , N H2, Ci-C6-alkyl, Ci-C6-halogen- alkyl, Ci-C6-alkoxy, CrC6-halogenalkoxy, CrC6-alkylthio, Ci-C6-halogenalkylthio, C1-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 ;
o is 0, 1 , 2 or 3; and
R78 are independently selected from halogen, OH , CN, N02, SH, N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2,
Figure imgf000145_0001
N H-S02-Rx, CH(=0),
Figure imgf000145_0002
C(=0)N H(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 heteroatoms 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-CB-alkylthio; R9 is in each case independently selected from H, halogen, OH, CN , ΝΟ∑, SH , N H2, N H(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH (C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4-alkynyl)2, N H(C3-C3-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4- alkenyl), N(Ci-C -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
Figure imgf000146_0001
NH-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),
Figure imgf000146_0002
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),
Figure imgf000146_0003
C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- C3-cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, C2-C3-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, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C - 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, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C -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 S02; 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, Ci-Ce-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 unsubsti- tuted 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; and the N-oxides and the agriculturally acceptable salts thereof.
2. The compounds of claim 1 , wherein R1 and R2 is in each case independently selected from the group consisting of H, halogen, and Ci-C6-alkyl.
3. The compounds of claims 1 to 2, wherein R3 is CH3, CH2F, CHF2 or CF3.
4. 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-C3-cycloalkynyl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(CrC6-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, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, S(0)n-Ci-C6-alkyl, NH-S02-Rx, N(Ci-C6-alkyl)2, CH(=0),
Figure imgf000147_0001
C6-alkyl), a saturated three-, four-, five-, six-, membered carbo-, heterocycle or aryl; 5. 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 or Ci-C6-halogenalkyl.
6. The compounds of claims 1 to 5, wherein R78 is in each case halogen.
7. The compounds of claims 1 to 5, wherein o is 0.
8. The compounds of any one of claims 1 to 7, wherein R9 and R10 independently are selected from H, CN, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkynyl, ORY, C3-C6- cycloalkyl.
9. A process for the synthesis of compounds I of claim 1 , comprising the step of:
a) reactin a compound X
Figure imgf000148_0001
10. The intermediate compounds X as defined in claim 9.
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 10 or 1 1 , 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 10 or 11.
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 10 or 1 1 , in an amount of from 0.1 to 10 kg per 100 kg of seed.
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