WO2015124706A1 - Composes n-acylimino heterocycliques pour lutter contre les nuisibles invertebres - Google Patents

Composes n-acylimino heterocycliques pour lutter contre les nuisibles invertebres Download PDF

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WO2015124706A1
WO2015124706A1 PCT/EP2015/053559 EP2015053559W WO2015124706A1 WO 2015124706 A1 WO2015124706 A1 WO 2015124706A1 EP 2015053559 W EP2015053559 W EP 2015053559W WO 2015124706 A1 WO2015124706 A1 WO 2015124706A1
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alkyl
het
radicals
cycloalkyl
group
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Karsten KÖRBER
Martin John MCLAUGHLIN
Birgit GOCKEL
Wolfgang Von Deyn
Jochen Dietz
Matthias Pohlman
Kenichi Kojima
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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  • the present invention relates to N-acylimino heterocyclic compounds, including their stereoisomers, tautomers and salts, and to compositions comprising such compounds.
  • the inven- tion also relates to the use of the N-acylimino heterocyclic compounds, their stereoisomers, their tautomers and their salts, for combating invertebrate pests.
  • the invention relates also to methods of combating invertebrate pests, which comprises applying such compounds.
  • Invertebrate pests such as insects, acaridae and nematode pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating animal pests. In particular, animal pests such as insects and acaridae are difficult to be effectively controlled.
  • EP 259738 discloses compounds of the formula A, which have insecticidal activity:
  • W is a substituted pyridyl radical or a 5-or 6-membered heterocyclic radical
  • R is hydrogen or alkyl
  • Y is inter alia a nitrogen atom
  • Z is an electron withdrawing group selected from nitro and cyano.
  • Pesticidal compounds which are similar to those of EP 259738, are known from
  • EP 639569 where the moiety electron withdrawing moiety Z is an electron withdrawing group such as alkoxcarbonyl, arylcarbonyl, heterocyclic carbonyl, Ci-C4-alkylsulfonyl, sulfamoyl or
  • Ar is an aryl or 5- or 6-membered heterocyclic group
  • R a is hydrogen or alkyi
  • Y' is hydrogen, halogen, a hydroxyl group, an alkyi group or an alkoxy group
  • Rb is an alkyi group substituted with halogen or an alkoxy group, optionally substituted with halogen.
  • Pesticidal compounds which are similar to those of US 2013/0150414, are known from WO 2013/129688.
  • the pesticidal activity of the compounds is not satisfactory. It is therefore an object of the present invention to provide compounds having a good pesticidal activity, especially against difficult to control insects and acarid pests.
  • N-substituted acyl-imino compounds of the general formula (I) described below by their stereoisomers, their tautomers and their salts. Therefore, the present invention relates to N-acylimino compounds of formula (I):
  • Cyc is a radical Cyc-1 or Cyc-2
  • X is O or S
  • D is CH2 or CH2-CH2, where 1 or 2 of the hydrogen atoms may be replaced by R 4 ,
  • Y is O, S, CR 5a R 5b or N-R 5 ;
  • W 1 , W 2 , W 3 and W 4 each individually represent CR V R W , wherein
  • each R w independently from each other, is hydrogen, halogen, cyano, azido, nitro,
  • each R v independently from each other, are selected from the group consisting of hydrogen, halogen, cyano, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl and C2-Cio-alkynyl, wherein the carbon atoms of the aforementioned four aliphatic and cycloaliphatic radicals may be unsubstituted or may be partly or fully halogenated or may optionally be further substituted with 1 , 2 or 3 identical or different radicals R 7 ; or
  • R w of adjacent carbon atoms may form both together and together with the existing bond a double bond between the adjacent carbon atoms
  • W 2 or W 3 may optionally represent a single or a double bond between the adjacent carbon atoms; are independently from each other selected from the group consisting of hydrogen, halogen, CN, SCN, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 ,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3-, 4-, 5- or 6-membered saturated or partly unsaturated carbocyclic or heterocyclic ring, wherein each of the carbon atoms of said cycle are unsubstituted or may carry any combination of 1 or 2 identical or different radicals R 7 , or
  • Z is O, S or N-R z ;
  • R z if present, is selected from the group consisting of hydrogen, CN, d-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 - cycloalkyl-Ci-C4-alkyl, Ci-C6-alkylcarbonyl, Ci-C6-alkylsulfonyl, Ci- C6-alkoxycarbonyl, wherein each of the eight last mentioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenyl-Ci-C4-alkyl, phenylcarbonyl, phenoxycarbonyl or phenylsulfonyl, where the phenyl ring in the last 5 mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ;
  • Het # represents a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2, 3 or 4 heteroa- toms as ring members, which are selected from oxygen, nitrogen and/or sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, and
  • Ci-C6-alkanediyl, C2-C6-alkenediyl, or C2-C6-alkynediyl is selected from the group consisting of halogen, cyano, azido, nitro,-SCN, SF 5 , d-Ce-alkyl, Ci-C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-Ci-C 4 - alkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 8 -halocycloalkyl-Ci-C 4 -alkyl, C2-C6-alkenyl, C2- Ce-haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 haloalkynyl, Si(R 11 ) 2 R 12 ,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is unsubstituted or substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 4 which are bound to the same carbon atom may, together with said carbon atom, form a 3- to 6-membered carbo- or heterocyclic ring, where the heterocyclic ring has 1 or 2 heteroatoms or heteroatom moieties as ring members which are selected from the group consisting of O, S, S(O), S(0)2 and N, where said carbo- or heterocyclic ring is unsubstituted or carry 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C2-C6-alkoxy, C3-C8- cycloalkyl, C2-C6-alkenyl, and C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or completely halogenated;
  • R 5 if present, is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl,
  • phenyl phenyl-Ci-C4-alkyl, phenylcarbonyl, phenoxycarbonyl and phenylsulfonyl, where the phenyl ring in the last five mentioned groups is unsubstituted or substituted with 1 to 5 identical or different substituents R 10 , or
  • R 5a , R 5b independently of each other are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, Ci-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein each of the five last mentioned radicals are unsubstituted, partly or completely halogenated, phenyl, and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , or
  • R 5a , R 5b together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated or partially unsaturated carbocycle or heterocycle, where the heterocycle has 1 or 2 heteroatoms as ring members which are selected from the group consisting of O and S, and wherein each of the carbon atoms of said carbo- or heterocycle is unsubstituted or may carry any combination of 1 or 2 identical or different radicals, which are independently of each other are selected from the group consisting of halogen, CN, Ci-C4-alkyl and C1-C4- haloalkyl; where, independently of their occurrence, n is 0, 1 or 2;
  • R 6 is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF 5 , Ci- Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the last 4 aliphatic and cycloaliphatic radicals may be partially or complete- ly halogenated and/or further substituted independently from one another with 1 , 2 or 3 radicals R 7 ,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocy- die ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 7 may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R 7 are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 ; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halo
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-Ci-C 4 -alkyl, C 3 -C 8 - halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloal
  • phenyl phenyl-Ci-C- 4 -alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , and
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 9b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3- C8-cycloalkyl-Ci-C 4 -alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6 haloalkynyl,
  • phenyl benzyl, 1 -phenethyl or 2-phenethyl, where the phenyl ring in the last four mentioned radicals is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ; and
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 9a and R 9b are together a C2-C7 alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partly saturated or unsaturated aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur or nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from OH, halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy, and
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocy- die ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituents selected independently from one another from halogen, cyano, NO2, Ci-C6-alkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • R 11 , R 12 independently of their occurrence, are selected from the group consisting of d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 4 -alkyl, C 2 -C 6 - alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-Ci-C 4 -alkyl, C3-Cs-halocycloalkyl-Ci-C 4 - alkyl, Ci-C6-haloalkoxy-Ci-C 4 -alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals are unsubstituted or substituted with 1
  • R 13 , R 14 independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C 4 -alkoxy-Ci-C 4 - alkyl, phenyl and benzyl;
  • R 15 independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C 4 - alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy,
  • phenyl, benzyl and pyridyl wherein the last three radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 , 2 or 3 substituents selected from
  • R 16 independently of its occurrence, is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fer/butyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci- C 4 alkoxy,
  • R 17 independently of its occurrence, is selected from the group consisting of hydrogen,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3-C8- cycloalkyl-Ci-C4-alkoxy, Ci-C6-alkylthio, wherein the 1 1 last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy,
  • radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl,
  • R 17a , R 17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, ferfbutyldimethylsilyl,
  • phenyl, benzyl, pyridyl, phenoxy wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substitu- ents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl,
  • R 17a and R 17b may together be a C2-C6 alkylene chain forming a 3- to 7- membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R 17a and R 17b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected, independently of each other, from oxygen, sulfur and nitrogen, and may optionally be substituted with halogen, C1-C4- haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • phenyl, benzyl and pyridyl wherein the last three radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino and di-(Ci-C6-alkyl)amino; the stereoisomers, tautomers and the salts thereof.
  • the present invention relates, in particular, to compounds of the formula (I), to the stereoisomers, the tautomers and the salts thereof, where Het is not tetrahydrofuran-3-yl, if Y is O, NH or S, R 3 is hydrogen and D is CH2 where one or two of the hydrogen atoms of CH2 may be replaced by R 4 .
  • the present invention relates, even more particularly, to compounds of the formula (I), to the stereoisomers, the tautomers and the salts thereof, where Het is not tetrahydrofu- ran-3-yl, if Y is O, NR 5 or S and D is CH2 where one or two of the hydrogen atoms of CH2 may be replaced by R 4 .
  • the present invention relates, especially, to compounds of the formula (I), to the stereoisomers, the tautomers and the salts thereof, where Het is not tetrahydrofuran-3-yl. Moreover, the present invention relates to and includes the following embodiments:
  • compositions comprising an amount of at least one compound of the formula (I) or a stereoisomer, tautomer or salt thereof;
  • a method for protecting growing plants from attack or infestation by invertebrate pests comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of the formula (I) or a stereoisomer, a tautomer or salt thereof, in particular a method protecting crop plants from attack or infestation by animal pests, which comprises contacting the crop plants with a pesticidally effective amount of at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;
  • a method for the protection of plant propagation, especially seeds, from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;
  • seeds comprising a compound of the formula (I) or an enantiomer, diastereomer or salt thereof;
  • a method for treating animals infested or infected by parasites or preventing animals of getting infected or infested by parasites or protecting animals against infestation or infection by parasites which comprises administering or applying to the animals a parasiticidal- ly effective amount of a compound of formula (I) or the stereoisomers and/or salts, in particular veterinary acceptable salts, thereof;
  • a process for the preparation of a veterinary composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises formulating a compound of formula (I) or a stereoisomer, tautomer and/or veterinary acceptable salt thereof with a carrier composition suitable for veterinary use;
  • the present invention also relates to plant propagation materials, in particular as mentioned above to seeds, containing at least one compound of formula (I), a stereoisomer, a tautomer and/or an agriculturally acceptable salt thereof.
  • the present invention relates to every possible stereoisomer of the compounds of formula (I), i.e. to single enantiomers, diastereomers and E/Z-isomers as well as to mixtures thereof and also to the salts thereof.
  • the present invention relates to each isomer alone, or mixtures or combinations of the isomers in any proportion to each other.
  • Suitable compounds of the formula (I) also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
  • the compounds of the formula (I) may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • One center of chirality is the carbon ring atom carrying radical R 1 .
  • the invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures.
  • the present invention also relates to potential tautomers of the compounds of formula (I) and also to the salts of such tautomers.
  • the present invention relates to the tautomer as such as well as to mixtures or combinations of the tautomers in any proportion to each other.
  • the term "tautomers” encompasses isomers, which are derived from the compounds of formula (I) by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.
  • the compounds of the present invention i.e. the compounds of formula (I), their stereoi- somers, their tautomers as well as their salts, in particular their agriculturally acceptable salts and their veterinarily acceptable salts, may be amorphous or may exist in one ore more different crystalline states (polymorphs) or modifications which may have a different macroscopic proper- ties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of the formula (I), mixtures of different crystalline states or modifications of the respective stereoisomers or tautomers, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the formula (I) are preferably agriculturally salts as well as veterinary acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula (I) has a basic functionality or by reacting an acidic compound of formula (I) with a suitable base.
  • Suitable agriculturally or veterinary useful salts are especially the salts of those cations or anions, in particular the acid addition salts of those acids, whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH4 + ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy- Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammo- nium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, 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, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen car- bonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4- alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n - Cm indicates in each case the possible number of carbon atoms in the group.
  • Halogen will be taken to mean fluoro, chloro, bromo and iodo.
  • partially or fully halogenated will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in partic- ular by fluorine or chlorine.
  • partially or fully halogenated alkyl is also termed haloalkyl
  • partially or fully halogenated cycloalkyl is also termed halocycloalkyl
  • partially or fully halogenated alkylenyl is also termed haloalkenyl
  • partially or fully halogenated alkylynyl is also termed haloalkynyl
  • partially or fully halogenated alkoxy is also termed haloalkoxy
  • partially or fully halogenated alkylthio is also termed haloalkthio
  • partially or fully halogenated alkylsulfinyl is also termed haloalkylsulfinyl
  • partially or fully halogenated alkylsulfonyl is also termed haloalsulfonyl
  • partially or fully halogenated cycloalkylalkylalkyl is also termed halocycloalkylalkyl.
  • C n -C m -alkyl as used herein, and also in C n -C m -alkylamino, di-C n -C m -alkylamino,
  • Cn-Cm-alkylaminocarbonyl di-(C n -C m -alkylamino)carbonyl, C n -C m -alkylthio , C n -C m -alkylsulfinyl and Cn-Cm-alkylsulfonyl, refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g.
  • 1 to 10 carbon atoms preferably 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl,
  • Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.
  • C n -C m -alkanediyl refers to a linear or branched saturated bivalent hydrocarbon group having n to m, e.g. 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, for example methylene, ethane-1 ,1 -diyl, ethane-1 ,2-diyl, propane-1 ,1 -diyl, propane-1 ,2-diyl, propane-1 ,3-diyl, propane-2,2-diyl, butane-1 ,1 -diyl, butane-1 ,2-diyl, butane-2,3-diyl, butane-2,2- diyl, butane-1 ,3-diyl, butane-1 ,4-diyl, pentane-1 ,1 -diyl, pentane-2,2-diyl, pentane-3,3
  • linear Ci-C6-alkanediyl refers to a linear saturated bivalent hydrocarbon group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, for example methylen, ethane-1 ,2-diyl, propane-1 ,3-diyl, butane-1 ,4-diyl, pentane-1 ,5-diyl and hexane-1 ,6- diyl.
  • C n -C m -haloalkyl refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g.
  • Ci-C4-haloalkyl such as chloro- methyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluorome- thyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 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, pent
  • Ci-C4-haloalkyl such as chloro- methyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl
  • Ci-Cio-haloalkyl in particular comprises Ci-C2-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoro- methyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.
  • Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
  • C n -C m -haloalkoxy refers to straight-chain or branched alkyl groups having n to m carbon atoms, e.g.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • Ci-C4-Alkoxy is, for example, methoxy, ethoxy, n- propoxy, 1 -methylethoxy (isopropoxy), butoxy, 1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy).
  • Ci-C6-Alkoxy includes the meanings given for Ci-C4-alkoxy and also includes, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 - dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethyl butoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1 -ethyl-1 -methylpropoxy or 1 -ethyl-2-methylpropoxy.
  • Ci-Cs-Alkoxy includes the meanings given for Ci-C6-alkoxy and also includes, for example, heptyloxy, octyloxy, 2- ethylhexyloxy and positional isomers thereof.
  • Ci-Cio-Alkoxy includes the meanings given for Ci- Ce-alkoxy and also includes, for example, nonyloxy, decyloxy and positional isomers thereof.
  • C n -C m -alkylthio is a C n -C m -alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C2-Alkylthio is methylthio or ethylthio.
  • Ci-C4-Alkylthio is, for example, methylthio, ethyl- thio, n-propylthio, 1 -methylethylthio (isopropylthio), butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio).
  • Ci-C6-Alkylthio includes the meanings given for Ci-C4-alkylthio and also includes, for example, pentylthio, 1 - methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2- dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2- dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,
  • Ci-Cs-Alkylthio includes the meanings given for Ci-C6-alkylthio and also includes, for example, heptylthio, oc- tylthio, 2-ethylhexylthio and positional isomers thereof.
  • Ci-Cio-Alkylthio includes the meanings given for Ci-Cs-alkylthio and also includes, for example, nonylthio, decylthio and positional iso- mers thereof.
  • C n -C m -haloalkyloxy is a C n -C m -haloalkyl group, as defined above, attached via an oxygen atom.
  • Examples include Ci-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluo- romethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 - fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and pen
  • C n -C m -haloalkylthio is a C n -C m -haloalkyl group, as defined above, attached via a sulfur atom.
  • Examples include Ci-C2-haloalkylthio, such as chloromethylthio, bromomethyl- thio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethyl- thio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1 -chloroethylthio, 1 -bromoethylthio, 1 -fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2- trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2, 2-
  • Ci-C2-fluoroalkoxy and Ci-C2-fluoroalkylthio refer to Ci-C2-fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respec- tively.
  • C2-C m -alkenediyl refers to linear or branched mono- unsaturated bivalent hydrocarbon group having 2 to m, e.g.2 to 6 carbon atoms, preferably 2 to 4 carbon atoms, for example ethene-1 ,1-diyl, ethene-1,2-diyl, prop-1-ene-1 ,1-diyl, prop-1-ene- 1,2-diyl, prop-2-ene-1,1-diyl, prop-2-ene-1,2-diyl, propene-1,3-diyl, but-1 -ene-1 ,1 -diyl, but-1- ene-1 ,2-diyl, but-1 -ene-1 ,3-diyl, but-2-ene-1 ,1-diyl, but-2-ene-1,2-diyl, but-3-ene-1,1-diyl
  • C2-C m -haloalkenyl refers to C2-C m -alkenyl, where some or all of the hydro- gen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example 1-fluoroethenyl, 2-fluoroethenyl, 2,2-difluoroethenyl, 1 ,2,2-trifluoroethenyl, 1-fluoro-2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl, 1-fluoro-1- propenyl, 1,2-difluoro-1 -propenyl, 3,3-difluoropropen-2-yl, 1-chloroethenyl, 2-chloroethenyl, 2,2,- dichloroe
  • C2-C m -alkynyl refers to a linear or branched unsaturated hydrocarbon group having 2 to m, e.g.2 to 10 or 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1-butynyl, 2-butynyl, and the like.
  • C2-C m -haloalkynyl as used herein, which is also expressed as “C2-C m -alkynyl which is partially or fully halogenated”, refers to C2-C m -alkynyl, where some or all of the hydro- gen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • C2-C m -haloalkynyl examples include 1-fluoro-2-propenyl, 2- fluoro-2-propenyl, 3-fluoro-2-propenyl, 1 -fluoro-2-propynyl and 1 ,1 -difluoro-2-propenyl, and the like.
  • C3-C m -cycloalkyl refers to a monocyclic and polycyclic 3- to m- membered saturated cycloaliphatic radicals, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohex- yl, cycloheptyl, cyclooctyl, cyclodecyl, bicyclo[2.2.1 ]heptyl, bicyclo[3.1 .1]heptyl, bicy- clo[2.2.2]octyl and bicyclo[3.2.1 ]octyl.
  • cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
  • C3-C m -halocycloalkyl as used herein, which is also expressed as “cycloalkyl which is partially or fully halogenated”, refers C3-C m -cycloalkyl as mentioned above, in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • C3-C m -halocycloalkyl examples include 1 - fluorocycloprpyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 1 -chlorocyclcopropyl, 2- chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,3-difluorocyclopropyl, 1 -fluorocycobutyl etc.
  • C3-C m -cycloalkyl-Ci-C4-alkyl refers to a C3-C m -cycloalkyl group as defined above, which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • C3-C m -cycloalkyl-Ci-C4-alkyl examples include cyclopropyl methyl, cyclopropylethyl, cyclopropyl propyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclo- pentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
  • C3-C m -halocycloalkyl-Ci-C4-alkyl refers to a C3-C m -halocycloalkyl group as de- fined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms, e.g. like specific examples mentioned above, wherein one hydrogen atom of the alkyl radical is replaced by an Ci-C4-alkoxy group.
  • Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert- butoxymethyl, 1 -methoxyethyl, 1 -ethoxyethyl, 1 -propoxyethyl, 1 -isopropoxyethyl, 1 -n- butoxyethyl, 1 -sec-butoxyethyl, 1 -isobutoxyethyl, 1 -tert-butoxyethyl, 2-methoxyethyl, 2- ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2- isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1 -ethoxypropyl, 1 -propoxypropyl, 1 - is
  • Ci-C4-haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms, either in the alkoxy moiety or in the alkyl moiety or in both, are replaced by halogen atoms.
  • Examples are difluoromethoxymethyl (CHF2OCH2), trifluoromethoxymethyl, 1 -difluoromethoxyethyl, 1 - trifluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl, difluoro-methoxy-methyl (CH3OCF2), 1 ,1 -difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.
  • Ci-C m -alkoxycarbonyl is a Ci-C m -alkoxy group, as defined above, attached via a carbonyl group atom.
  • Ci-C2-Alkoxycarbonyl is methoxycarbonyl or ethoxycarbonyl.
  • C1-C4- Alkoxy is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1 - methylethoxycarbonyl, butoxycarbonyl, 1 -methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1 ,1 -dimethylethoxycarbonyl.
  • Ci-C6-Alkoxycarbonyl includes the meanings given for C1-C4- alkoxycarbonyl and also includes, for example, pentoxycarbonyl, 1 -methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1 ,1 -dimethylpropoxycarbonyl, 1 ,2- dimethylpropoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1 -ethylpropoxycarbonyl, hexoxycar- bonyl, 1 -methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4- methylpentoxycarbonyl, 1 ,1 -dimethylbutoxycarbonyl, 1 ,2-dimethylbutoxycarbonyl,
  • aryl refers to an aromatic hydrocarbon radical such as naphthyl or in particular phenyl.
  • 3- to 6-membered carbocyclic ring refers to cyclopropane, cy- clobutane, cyclopentane and cyclohexane rings.
  • 3- to 7-membered carbocyclic ring refers to cyclopropane, cyclobutane, cyclopentane, cyclohexane and cyclohep- tane rings.
  • heterocyclic ring containing 1 , 2 or 3 heteroatoms or “containing heteroatom groups", wherein those heteroatom(s) (group(s)) are selected from N, O, S, NO, SO and SO2 and are ring members, as used herein refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic.
  • the heterocyclic radical may be attached to the remainder of the mole- cule via a carbon ring member or via a nitrogen ring member.
  • Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic rings include: oxiranyl, aziridinyl, azetidinyl, 2 tetrahydrofuranyl, 3-tetrahydrofuranyl, 2 tetrahydrothienyl, 3 tetrahy- drothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyrazolidinyl, 5-pyrazolidinyl, 2 imidaz- olidinyl, 4 imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4 isoxa- zolidinyl, 5 isoxazolidinyl, 2 thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3 isothiazolidinyl, 4- is
  • Examples of 5- or 6-membered aromatic heterocyclic rings also termed heteroaromatic rings or hetaryl, include: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4- pyrazo-"lyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4 thiazolyl, 5-thiazo-"lyl, 2- imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
  • C2-Cm-alkylene is divalent branched or preferably non-branched or linear saturated aliphatic chain having 2 to m, e.g. 2 to 7 carbon atoms, for example CH2CH2, -CH(CH3)-,
  • the term "compound(s) of the present invention” or “compound(s) according to the invention” refers to the compound(s) of formula (I) as defined above, which are also referred to as “compound(s) of formula I” or “compound(s) I” or “formula I compound(s)”, and includes their salts, tautomers, and stereoisomers.
  • Embodiments of the present invention as well preferred compounds of the present inven- tion are outlined in the following paragraphs.
  • the remarks made below concerning preferred embodiments of the variables of the compounds of formula (I), especially with respect to their substituents X, W 1 , W 2 , W 3 , W 4 , Het, Cyc, Y, D, R 1 , R 2 and R 3 , and the variables k and m are valid both on their own and, in particular, in every possible combination with each other.
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is unsubstituted or substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 4 which are bound to the same carbon atom may, together with said carbon atom, form a 3- to 6-membered carbo- or heterocyclic ring, where the heterocyclic ring has 1 or 2 heteroatoms or heteroatom moieties as ring members which are selected from the group consisting of O, S, S(O), S(0)2 and N, where said carbo- or heterocyclic ring is unsubstituted or carry 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C2- C6-alkoxy, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or completely halogenated, wherein R 7A , R 8 , R 9A , R 9B , R 10 , R 11 , R 12 , R 13
  • Het is selected from the group consisting of radicals of formulae Het-1 to Het-24, with preference given to compounds of the formula (I), their stereoisomers, there tautomers and their salts, where Het is selected from the radicals of the formulae Het-1 , Het-1 1 and Het-24:
  • Het-21 Het-22 Het-23 Het-24 wherein # denotes the bond in formula (I), and wherein R 6 and k are as defined above and where R 6A is hydrogen or has one of the meanings given for R 6 and where R 6B is hydrogen or a C-bound radical mentioned as R 6 and where R 6B is in particular hydrogen, Ci-C4-alkyl or C1-C4- haloalkyl.
  • k is 0, 1 or 2, especially 0 or 1.
  • Het-1 , Het-2, Het-3, Het-4, Het-7, Het-8, Het-9, Het-10, Het-11 , Het-18 and Het-21 k is especially 1.
  • R 6A in formulae Het-12, Het-13, Het-14, Het-16, Het-17, Het-19, Het 20 and Het-22 is different from hydrogen.
  • R 6 is in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, C1-C4- haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoro- methyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci- C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroeth
  • R 6a is in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroeth
  • R 6b is in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably C1-C2- alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
  • Ci-C4-alkyl such as methyl or ethyl
  • Ci-C4-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethy
  • Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24,
  • R 6 is selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, C1-C4- haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluo- roethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and C1-C2- haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-
  • R 6a is selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pen- tafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci- C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluor
  • k 0, 1 or 2.
  • a particularly preferred group of embodiments relates to compounds of formula (I), to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 , where k is 0, 1 or 2, in particular 1 or 2 and especially 1 and where R 6 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci- C4-alkyl and Ci-C4-haloalkyl, even
  • a particular sub-group of embodiments relates to compounds of the formula (I), to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 a
  • R 6 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, and C1-C4- haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl;
  • halogen such as chlorine or fluorine
  • Ci-C4-alkyl such as methyl or ethyl
  • C1-C4- haloalkyl such as difluoromethyl,
  • R 6a is as defined above and in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine and Ci-C4-alkyl, such as methyl or ethyl, more preferably is hydrogen.
  • a special embodiment of the radical Het-1 a is 6-chloropyridin-3-yl, i.e. R 6a is hydrogen and R 6 is chlorine.
  • a further special embodiment of the radical Het-1 a is 6-(trifluoromethyl)pyridin-3- yl, i.e. R 6a is hydrogen and R 6 is trifluoromethyl.
  • Another particularly preferred group of embodiments relates to compounds of formula (I), to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 1 , where k is 0, 1 or 2, in particular 0 or 1 , and where Het is in particular a radical of formula Het-1 1 a,
  • R 6a is as defined above and wherein R 6a is in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and C1-C4- haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluor
  • Het is a radical of formula Het-24, where k is 0, 1 or 2, in particular 0 or 1 , and where R 6 , if present, is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci- C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoro
  • R 1 and R 2 are independently from each other selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6- cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 , 1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl.
  • Ci-C6-alkyl in particular Ci-C4
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl.
  • R 1 and R 2 are independently from each other selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluo- romethyl, 1 , 1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl.
  • At least one of the radicals R 1 and R 2 is hydrogen.
  • a first group (1 ) of embodiments relates to compounds of the formula (I), to their stereoi- somers and their tautomers and to the salts thereof, where Cyc in formula (I) is a radical Cyc-1 .
  • a second group (2) of embodiments relates to compounds of the formula (I), to their stereoisomers and their tautomers and to the salts thereof, where Cyc in formula (I) is a radical Cyc-2.
  • R 3 is in particular selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-
  • Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl and Ci-C4-haloalkylthio especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-haloalkyl and Ci-C4-haloalkoxy.
  • R 3 is more particularly selected from the group consisting of hydrogen, C1-C6- alkyl, C3-C6-cycloalkyl, Ci-C6-alkyl-S, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated;
  • Ci-C4-alkoxycarbonyl and Ci-C4-haloalkylthio especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-haloalkyl and Ci-C4-haloalkoxy.
  • R 3 is especially selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-
  • phenyl or 6-membered hetaryl wherein the 6-membered hetaryl comprises 1 , 2 or 3 nitrogen atoms as ring members, such as pyridyl, pyrimidinyl, pyrazinyl and pyridazinyl, and wherein phenyl and hetaryl are unsubstituted or carry 1 , 2 or 3 identical or different radicals R 10 as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, N0 2 , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkyl, C1-C4- haloalkoxy, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4
  • first and second groups (1 ) and (2) of embodiments D is preferably CH2, where 1 or both hydrogen atoms may be substituted by R 4 , wherein
  • R 4 if present, is as defined above, and preferably selected from the group consisting of halogen, in particular fluorine, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-alkyl- S, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each Ci-C6-alkyl, C3-
  • Ci-C6-alkyl-S and C3-C6-cycloalkylmethyl are unsubstituted, partly or completely halogenated,
  • R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, C1-C4- haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl and Ci- C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci- C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy,
  • R 4 if present, is more preferably selected from the group consisting of hydrogen, halogen, in particular fluorine, Ci-C4-alkyl, such as methyl or ethyl, C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, wherein the carbon atoms of each Ci-C6-alkyl and C3-C6-cycloalkyl are unsubstituted, partly or completely halogenated,
  • phenyl which is unsubstituted or carries 1 , 2 or 3 radicals R 10 , where R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, C1-C4- alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and C1-C4- haloalkoxy,
  • first and second groups (1 ) and (2) of embodiments D is more preferably selected from the group consisting of CH2, CH F, CF2,
  • D is in particular selected from the group consisting of CH2, CH F, CF2, CHCN,
  • CH(CH 3 ), CH(C 2 H 5 ), C(CH 3 ) 2 , cyclopropan-1 ,1 -diyl, cyclobutan-1 ,1 -diyl, and D is especially CH2.
  • D is also especially CH(CHs).
  • Y is as defined above and in particular O or NR 5 . Especially Y is O.
  • the radical R 5 is as defined above and preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-alkylcarbonyl, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated,
  • phenyl and benzyl where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined above and preferably selected from the group consisting of halogen, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci- C4-haloalkoxy and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • the radical R 5 is more preferably selected from the group consisting of hydro- gen, Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined above and preferably selected from the group consisting of halogen, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci- C4-haloalkyl, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • the radicals R 5a and R 5b are preferably selected from the group consisting of hydrogen, halogen, in particular fluorine, Ci-C6-alkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each Ci-C6-alkyl, C3-C6- cycloalkyl, and C3-C6-cycloalkylmethyl are unsubstituted, partly or completely halogenated, phenyl or benzyl, where the phenyl rings in the two last mentioned radicals are unsubstituted or carry 1 , 2 or 3 radicals R 10 , where R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-alkylthio,
  • the radicals R 5a and R 5b are more preferably selected from the group consisting of hydrogen, halogen, in particular fluorine, Ci-C4-alkyl, such as methyl or ethyl, C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, wherein the carbon atoms of each Ci-C6-alkyl and C3-C6-cycloalkyl are unsubstituted, partly or completely halogenated, and phenyl, which is unsubstituted or carries 1 , 2 or 3 radicals R 10 , where R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C
  • At least one of the radicals R 5a and R 5b is hydrogen, while the other is as defined above and in particular selected from the group consisting of hydrogen, halogen, in particular fluorine, Ci-C4-alkyl, such as methyl or ethyl, C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, wherein the carbon atoms of each Ci-C6-alkyl and C3-C6-cycloalkyl are unsubstituted, partly or completely halogenated, and phenyl, which is unsubstituted or carries 1 , 2 or 3 radicals R 10 , where R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C
  • R 3 is in particular selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-
  • radicals R 10 as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-
  • D is CH2, where 1 or both hydrogen atoms may be substituted by R 4 , wherein R 4 if present, is as defined above, and preferably selected from the group consisting of halogen, in particular fluorine, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-alkyl- S, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each Ci-C6-alkyl, C3- C6-cycloalkyl, Ci-C6-alkyl-S and C3-C6-cycloalkylmethyl are unsubstituted, partly or completely halogenated,
  • R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, C1-C4- haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl and Ci-
  • C4-haloalkylthio especially from the group consisting of halogen, CN, NO2, Ci- C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy,
  • R 4 if present, is more preferably selected from the group consisting of halogen, in particular fluorine, Ci-C4-alkyl, such as methyl or ethyl, C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, wherein the carbon atoms of each Ci-C6-alkyl and C3-C6-cycloalkyl are unsubstituted, partly or completely halogenated,
  • phenyl which is unsubstituted or carries 1 , 2 or 3 radicals R 10 , where R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, C1-C4- alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and C1-C4- haloalkoxy,
  • R 5 if present, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3- C6-cycloalkyl, Ci-C6-alkylcarbonyl, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated, phenyl and benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined above and preferably selected from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and C1-C4- haloalkylthio, especially from the group consisting of halogen, CN, NO2, C1-C4- al
  • R 5 if present, is in particular selected from the group consisting of hydrogen, Ci- C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as de- fined above and preferably selected from the group consisting of halogen, CN,
  • R 3 is more particularly selected from the group consisting of hydrogen, C1-C6- alkyl, C3-C6-cycloalkyl, Ci-C6-alkyl-S, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated;
  • Ci-C4-alkyl Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci- C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-haloalkyl and Ci-C4-haloalkoxy.
  • D is CH2, where 1 or both hydrogen atoms may be substituted by R 4 , wherein
  • R 4 if present, is more preferably selected from the group consisting of halogen, in particular fluorine, Ci-C4-alkyl, such as methyl or ethyl, C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, wherein the carbon atoms of each Ci-C6-alkyl and C3-C6-cycloalkyl are unsubstituted, partly or completely halo- genated,
  • phenyl which is unsubstituted or carries 1 , 2 or 3 radicals R 10 , where R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, C1-C4- alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and C1-C4- haloalkoxy,
  • Y is O or NR 5 and especially Y is O, wherein
  • R 5 if present, is selected from the group consisting of hydrogen, Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined above and preferably selected from the group consisting of halogen, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and C1-C4- haloalkylthio, especially from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • R 3 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C3- C6-cycloalkyl-methyl, wherein the carbon atoms of each of the 3 last mentioned radicals are unsubstituted, partly or completely halogenated;
  • phenyl or 6-membered hetaryl wherein the 6-membered hetaryl comprises 1 , 2 or 3 nitrogen atoms as ring members, such as pyridyl, pyrimidinyl, pyrazinyl and pyri- dazinyl, and wherein phenyl and hetaryl are unsubstituted or carry 1 , 2 or 3 identical or different radicals R 10 as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, Ci- C4-alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C
  • CH(CH 3 ), CH(C 2 H 5 ), C(CH 3 ) 2 , cyclopropan-1 ,1 -diyl, cyclobutan-1 ,1 -diyl, and D is especially CH2;
  • Y is O or NR 5 and especially Y is O, wherein
  • R 5 if present, is selected from the group consisting of hydrogen, Ci-C6-alkyl, phenyl and benzyl, where the phenyl ring in the last two mentioned radicals is un- substituted or carries 1 , 2, 3 or 4 radicals R 10 , which are selected from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci- C4-haloalkyl, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio; particularly preferred from the group consisting of hydrogen, Ci-C4-alkyl, phe- nyl and benzyl, where the phenyl ring in the last two mentioned radicals is un- substituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined above and preferably selected from the group consisting of halogen, CN, Ci-C4-alkyl, Ci- C
  • R w is preferably selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci- C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluor
  • R w3 , R w4 and R w6 are hydrogen while R w5 has one of the meanings given for R w , and where R w5 is in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, in particular Ci-C
  • R w3 , R w4 and R w5 are hydrogen while R w6 has one of the meanings given for R w , and where R w6 is in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci- C4-haloalkoxy, in particular Ci-C2-haloalkoxy,
  • R w3 , R w4 , R w5 and R w6 are hydrogen.
  • radical of formula (A) represents a radical selected from the group consisting of W.Het-1 , W.Het-2, W.Het-3, W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-1 1 and W.Het-12, wherein the radical of formula (A) is in particular selected rom the radicals W.Het-1 , W.Het-2, W.Het-5, W.Het-6, W.Het-9 and W.Het-10.
  • R 1 , R 2 and Het are as defined herein and where R 1 , R 2 and Het, individually or in combination have the meanings given as preferred meanings, and wherein R w3 , R w4 , R w5 and R w6 are as defined above and in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl
  • R w5 is as defined above and in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n- propoxy and isopropoxy, and
  • the heterocycle Het is in particular selected from the group consisting of the radicals of formulae Het-1 to Het-24, as defined above, and in particular selected from the group consisting of the radicals of the formulae Het-1 or Het-1 a, Het-1 1 a and Het-24.
  • the radicals R 1 and R 2 are, independently from each other, in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or iso- propyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular C1-C2- haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or iso- propyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl
  • the radicals R 1 and R 2 are, independently from each other, more particularly selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl or 2,2,2-trifluoroethyl, where in particular at least one of the radicals R 1 and R 2 is hydrogen.
  • R 1 and R 2 in the moieties W.Het-1 , W.Het-2, W.Het-3, W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-1 1 and W.Het-12 are both hydrogen.
  • a particular group of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the radical A is selected from the group consisting of W.Het-2, W.Het-6 and W.Het-10 and wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24
  • R 6 is selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkyl;
  • R 6a is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-
  • k 0, 1 or 2.
  • a particular group (a) of embodiments relates to compounds of the formula (I), to their ste- reoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-1 , wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
  • a further particular group (b) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-2, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
  • a further particular group (c) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-5, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
  • a further particular group (d) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (3), (A), (B), (1 -A), (2-A) and (3-A) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-6, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
  • a further particular group (e) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-9, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
  • a further particular group (f) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-10, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
  • a special group (aa) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-1 , wherein Het is a radical of formula Het-1 a.
  • a further special group (ba) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-2, wherein Het is a radical of formula Het-1 a.
  • a further special group (ca) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-5, wherein Het is a radical of formula Het-1 a.
  • a further special group (da) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-6, wherein Het is a radical of formula Het-1 a.
  • a further special group (ea) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-9, wherein Het is a radical of formula Het-1 a.
  • a further special group (fa) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ) and (2) embodiments, wherein the moiety of formula (A) represents a radical selected from the group consisting of W.Het-10, wherein Het is a radical of formula Het-1 a.
  • the radical R w6 is as defined above and in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as meth- oxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluorome
  • the radical R w5 is as defined above and in particular selected from the group consisting of hydrogen, halogen, such as fluo- rine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as meth- oxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, di
  • radicals R 1 and R 2 are, independently from each other, in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particu- lar Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6-cycloalkyl, such as cyclopro- pyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoromethyl, 1,2,2-trifluoromethyl, 1,4-difluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroalkyl, such as
  • radicals R 1 and R 2 are, independently from each other, more particularly selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or iso- propyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 , 1 -d if I uoroethyl , 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, where in particular at least one of the radicals R 1 and R 2 is hydrogen and where especially both R 1 and R 2 are hydrogen.
  • R 3 is in particular selected from the group consisting of hydrogen, Ci-C6-alkyl, C3- C6-cycloalkyl, Ci-C6-alkyl-0, Ci-C6-alkyl-S, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each of the five last mentioned radicals are unsubstituted, partly or completely halogenated, it being also possible for these radicals to carry 1 or 2 radicals R 7 , which are different from Ci-C6-alkyl, it being also possible for cycloalkyl radicals to carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups;
  • D is CH2, where 1 or both hydrogen atoms may be substituted by R 4 , wherein
  • R 4 if present, is as defined above, and preferably selected from the group consist- ing of halogen, in particular fluorine, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-alkyl-
  • Ci-C6-alkyl-S C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each Ci-C6-alkyl, C3- C6-cycloalkyl, Ci-C6-alkyl-S and C3-C6-cycloalkylmethyl are unsubstituted, partly or completely halogenated,
  • R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, C1-C4- haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl and Ci- C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci- C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy,
  • R 4 if present, is more preferably selected from the group consisting of halogen, in particular fluorine, Ci-C4-alkyl, such as methyl or ethyl, C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, wherein the carbon atoms of each Ci-C6-alkyl and C3-C6-cycloalkyl are unsubstituted, partly or completely halogenated,
  • phenyl which is unsubstituted or carries 1 , 2 or 3 radicals R 10 , where R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, C1-C4- alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and C1-C4- haloalkoxy,
  • Y is O or NR 5 and especially Y is O, wherein R 5 if present, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3- C6-cycloalkyl, Ci-C6-alkylcarbonyl, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated,
  • phenyl and benzyl where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined above and preferably selected from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and C1-C4- haloalkylthio, especially from the group consisting of halogen, CN, NO2, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy;
  • R 5 if present, is in particular selected from the group consisting of hydrogen, Ci- C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined above and preferably selected from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • R 1 and R 2 are, independently from each other, selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, and Ci-C6-alkyl, in particular C1-C4- alkyl, such as methyl, ethyl, n-propyl or isopropyl;
  • R 3 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-alkyl-S, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated;
  • Ci-C4-alkyl Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci- C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-haloalkyl and Ci-C4-haloalkoxy.
  • D is CH2, where 1 or both hydrogen atoms may be substituted by R 4 , wherein
  • R 4 if present, is more preferably selected from the group consisting of halogen, in particular fluorine, Ci-C4-alkyl, such as methyl or ethyl, C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, wherein the carbon atoms of each Ci-C6-alkyl and C3-C6-cycloalkyl are unsubstituted, partly or completely halo- genated,
  • phenyl which is unsubstituted or carries 1 , 2 or 3 radicals R 10 , where R 10 is as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, C1-C4- alkoxycarbonyl and Ci-C4-haloalkylthio, especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and C1-C4- haloalkoxy,
  • Y is O or NR 5 and especially Y is O, wherein
  • R 5 if present, is selected from the group consisting of hydrogen, Ci-C4-alkyl, phe- nyl and benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined above and preferably selected from the group consisting of halogen, CN , Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and C1-C4- haloalkylthio, especially from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • R 1 and R 2 are both hydrogen
  • Y is O
  • D is selected from the group consisting of CH2, CH F, CF2, CHCN, CH(CHs), cyclopropan- 1 ,1 -diyl and cyclobutan-1 ,1 -diyl;
  • R 3 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C1-C6- alkyl-S, C3-C6-cycloalkyl-methyl, wherein the carbon atoms of each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated;
  • R 1 and R 2 are hydrogen
  • R 3 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, wherein the carbon atoms of each of the 2 last mentioned radicals are unsubstituted, partly or completely halogenated;
  • phenyl or 6-membered hetaryl wherein the 6-membered hetaryl comprises 1 , 2 or 3 nitrogen atoms as ring members, such as pyridyl, pyrimidinyl, pyrazinyl and pyri- dazinyl, and wherein phenyl and hetaryl are unsubstituted or carry 1 , 2 or 3 identical or different radicals R 10 as defined above and in particular selected, independently of each other, from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, Ci-
  • C4-alkoxycarbonyl and Ci-C4-haloalkylthio especially from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy;
  • D is selected from the group consisting of CH 2 , CHF, CF 2 , CHCN, CH(CH 3 ), CH(C 2 H 5 ), C(CH3)2, cyclopropan-1 ,1 -diyl, cyclobutan-1 ,1 -diyl, and D is especially CH2;
  • Y is O or NR 5 and especially Y is O, wherein
  • R 5 if present, is selected from the group consisting of hydrogen, Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined above and preferably selected from the group consisting of halogen, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and C1-C4- haloalkylthio, especially from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • R 1 and R 2 are hydrogen or one of R 1 and R 2 may be methyl;
  • R 3 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, wherein the carbon atoms of each of the 2 last mentioned radicals are unsubstitut- ed, partly or completely halogenated.
  • D is selected from the group consisting of CH 2 , CHF, CF 2 , CHCN, CH(CH 3 ), CH(C 2 H 5 ),
  • Y is O or NR 5 and especially Y is O, wherein
  • R 5 if present, is selected from the group consisting of hydrogen, methyl and ethyl.
  • R 5 if present, is selected from the group consisting of hydrogen, methyl and ethyl.
  • X is in particular O.
  • Het # in particular represents a 5- or 6-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur, where the aromatic heterocyclic ring is optionally substituted with 1 , 2 or 3 identical or different substituents R 10 , and where Het # is in particular a 5- or 6-membered aromatic heterocyclic ring, i.e.
  • hetaryl comprising 1 , 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, such as pyridyl, pyrimidinyl, pyrazinyl, pyridazinly, thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, pyrazolyl, imidazolyl, isothiazolyl or isoxazolyl, where hetaryl is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 and where the radical R 10 , irrespective of its occurrence, is in particular selected from halogen, CN, Ci-C4-alkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkyl, C1-C4- alkoxy, and Ci-C4-haloalkoxy.
  • R v is hydrogen .
  • R w irrespectively of its occurrence, is selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C4- alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -d
  • R 6 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluormethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluo- rine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,
  • R 7 irrespectively of its occurrence, is selected from the group consisting of CN, C1-C4- alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluormethoxy, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoro- ethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C3-C6-cycloalkyl such as cyclopropy
  • R 7a irrespectively of its occurrence, is selected from the group consisting of hydro- gen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, and phenyl , where the phenyl ring in the last radical is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such
  • R 8 irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular C1-C2- haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethy
  • R 9a and R 9b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR 9a R 9b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C
  • radicals NR 9a R 9b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2- butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, N- methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N-methyl-N- isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N-isobutylamino, 1 -pyrrolidinyl, 1 -piperidinyl, 1 -piperazinly, 4-methyl-1 -piperazinly and 4-morpholinyl.
  • R 10 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci- C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluor
  • R 11 , R 12 independently of their occurrence, are selected from the group consisting of Ci- C6-alkyl, Ci-C6-alkoxy, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or substituted with 1 , 2, or 3 identical or different radicals selected from fluorine, chlorine, Ci-C3-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy and Ci-C 2 -haloalkoxy.
  • R 13 , R 14 independently of their occurrence, are selected from the group consisting of hydrogen, fluorine, chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl or n-butyl, C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, and phenyl.
  • R 15 irrespectively of its occurrence, is selected from the group consisting of hydro- gen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroeth
  • R 16 irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or dif- ferent radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular C1-C2- haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-di
  • R 17 irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyl, C3-C6- cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is un- substitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-flu
  • R 17a and R 17b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR 9a R 9b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C
  • radicals NR 17a R 17b in- elude are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n- butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n- butylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N- methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N- isobutylamino, 1 -pyrrolidinyl, 1 -piperidinyl, 1 -piperazinly, 4-methyl-1 -piperazinly and 4- morpholinyl.
  • R 17c irrespectively of its occurrence, is selected from the group consisting of hydro- gen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoro
  • a special group of embodiments relates to the compounds of formula (l)-A.1 a, to their tau- tomers, to their stereoisomers and to their salts, where R 1 , D, Y, R 3 and R 4 are as defined above, examples being the compounds of formula (l)-A.1 a, their tautomers, their stereoisomers and their salts, where R 1 is H, Y is O, and where D and R 3 have one of the meanings given in any of lines 1 to 792 of the following table A.
  • a further special group of embodiments relates to the compounds of formula (l)-A.1 a', to their tautomers, to their stereoisomers and to their salts, where R 1 , D, Y, R 3 and R 4 are as de- fined above, examples being the compounds of formula (l)-A.1 a, their tautomers, their stereoisomers and their salts, where R 1 is H, Y is O, and where D and R 3 have one of the meanings given in any of lines 1 to 792 of the following table A.
  • a further special group of embodiments relates to the compounds of formula (l)-A.2a, to their tautomers, to their stereoisomers and to their salts, where R 1 , D, Y, R 3 and R 4 are as defined above, e.g. the compounds of formula (l)-A.2a, their tautomers, their stereoisomers and their salts where R 1 is H, Y is O, and where D and R 3 have in particular one of the meanings given in any of lines 1 to 792 of the following table A.
  • a further special group of embodiments relates to the compounds of formula (l)-A.3a, to their tautomers, to their stereoisomers and to their salts, where R 1 , D, Y, R 3 and R 4 are as defined above, e.g. the compounds of formula (l)-A.3.a, their tautomers, their stereoisomers and their salts, where R 1 is H, Y is O, and where D and R 3 have one of the meanings given in any of lines 1 to 792 of the following table A.
  • pecial groups of embodiments are the compounds of formulae (l)-A.3a ⁇ (l)-A.3b, (l)-A.3b ⁇ (l)-A.3c, (l)-A.3c ⁇ (l)-A.3d and (l)-A.3d', their tautomers, their stereoisomers and their salts, where R 1 is CH3, Y is N-C2H5 and where D and R 3 have one of the meanings given in any of lines 1 to 792 of the following table A.
  • R 1 is methyl may have R- or S-configuration with regard to the carbon atom that carries R 1 .
  • the aforementioned embodiments include both the R-isomer and the S-isomer
  • the compounds of formula (I) according to the present invention can be prepared e.g. according the preparation methods and preparation schemes as described below.
  • Compounds of formula (I) according to the present invention can be prepared by standard methods of organic chemistry e.g. by the preparation methods and preparation schemes as described below.
  • the definitions of Het, Cyc, D, X, Y, W 1 , W 2 , W 3 , W 4 , R 1 , R 2 and R 3 of the molecular structures given in the schemes are as defined above.
  • Room temperature means a temperature range between about 20 and 25 °C.
  • the compounds of formula (I) according to the present invention can be prepared e.g. according the preparation methods and preparation schemes as described below.
  • Compounds of formula (I) according to the present invention can be prepared by standard methods of organic chemistry e.g. by the preparation methods and preparation schemes as described below.
  • the definitions of Het, X, Y, W 1 , W 2 , W 3 , W 4 , R 1 , R 2 , R 3 , and R 4 of the molecular structures given in the schemes are as defined above.
  • Room temperature means a temperature range between about 20 and 25 °C.
  • the transformation is preferably carried out in polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, N,N- dimethylformamide, ⁇ , ⁇ -dimethylacetamide, N-methylpyrolidinone or in an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane at temperatures ranging between room temperature and the reflux temperature of the solvent.
  • polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, N,N- dimethylformamide, ⁇ , ⁇ -dimethylacetamide, N-methylpyrolidinone
  • an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane at temperatures ranging between room temperature and the reflux temperature of the solvent.
  • Examples of suitable leaving groups (Lg) in formula (III) include, but are not limited to: halogen, alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, alkyl phosphoante, halophosphate and various activated esters derived from the reaction of a free carboxylic acid with a peptide coupling rea- gent in the presence of an amine base ⁇ Chem. Rev., 2011 , 111 (1 1 ), 6557-6602).
  • Compounds of the formula (II) can be prepared, for example, by alkylation of the appropriate amino-heterocycle precursor (V) with the appropriate reagent of formula (VI) as depicted in the following scheme B.
  • the reaction is preferably carried out in polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, ⁇ , ⁇ -dimethylformamide, N,N- dimethylacetamide, N-methylpyrolidinone or a C1-C6 alcohol or inert solvents such as: dichloro- methane, 1 ,2-dichloroethane, 1 ,2-dimethoxyethane, carbon tetrachloride, tetrahydrofuran, toluene, xylenes, mesitylene, cymene, tetralone ranging between room temperature and the reflux temperature of the solvent.
  • polar solvents such as acetonitrile
  • reaction conditions for the alkylation of compounds analogous to formula (V) are given in Tet. Lett. 201 1 , 52(23), 3033-3037.
  • suitable leaving groups Lg 2 in formula (VI) include, but are not limited to: halogen, alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, alkyl phosphonate, etc.
  • Compound (la) corresponds to a compound of formula I, wherein Cyc is Cyc-1 , wherein D is CHR with R being hydrogen or having one of the meanings given for R 4 and where Y is O
  • compound (lb) corresponds to a compound of formula I, wherein Cyc is Cyc-2, wherein D is CHR with R being hydrogen or having one of the meanings given for R 4 and where Y is O.
  • a compound of formula (VII) is reacted with a hydroxamic acid halogenide compound of formula (VIII) or with the corresponding nitroxide compound in the sense of a 1 ,3- dipolar cycloaddition to yield the compound of formulae (la) or (lb) or a mixture thereof, depending on the stereoelectronic requirements, which compounds (la) and (lb) can be easily separat- ed.
  • the reaction is usually carried out in the presence of a base.
  • Suitable bases are inorganic bases such as alkali metal carbonates, earth alkali metal carbonates, alkali metal hydrogen carbonates or earth alkali metal carbonates such as potassium carbonate or potassium hydrogen carbonates or organic bases such as trialkylamines such as trimethylamine.
  • J is halogen, in particular chlorine.
  • the compound of formula (VIII) can be prepared e.g. by halo- genation of the corresponding oxime with N-chlorosuccinimide, as described e.g. in WO
  • Compound lc corresponds to a compound of formula I, wherein Cyc is Cyc-1 , wherein D is CHR with R being hydrogen or having one of the meanings given for R 4 and where Y is
  • compound Id corresponds to a compound of formula I, wherein Cyc is Cyc-2, wherein D is CHR with R being hydrogen or having one of the meanings given for R 4 and where Y is Y is CR 5a R 5b .
  • the reaction of the compound of formula (VII) with the compound of formula (IX) depicted in scheme E can be achieved by alkylation, followed by fluorine catalysis by analogy to the method described in WO 2012/042007 or in WO 2009/097992.
  • the reaction may result in the compound of formulae (lc) or (Id) or a mixture thereof, which can be separated by standard methods.
  • Compounds of formula (IX) are known in the art and can be prepared by methods described in WO 2009/097992.
  • X is preferably oxygen.
  • the sulfur atom is best installed in a subsequent step from the compound where X is an oxygen atom as detailed in scheme F.
  • the transformation is preferably carried out using a thio- phosphorous reagent of substructure (X), such as Lawesson's reagent.
  • the reaction is preferably carried out in a polar solvent such as acetonitrile, acetone, tetrahydrofuran, N,N- dimethylformamide, or in an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2- dimethoxyethane at temperatures ranging between room temperature and the reflux temperature of the solvent.
  • Suitable R a groups in compounds of formula (X) are e.g.
  • Ci-C4-alkyl aryl, such as phenyl which is unsubstituted or substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl or Ci-C4-alkoxy.
  • Representative reaction conditions for thionation analogous substrates are given in US 2013/102568.
  • a) or (lll.b), respectively can be achieved by acylation of the amine functionality in compounds of formula (II) using carboxylic acid derivatives (III. a) or (lll.b), respectively, which may or may not be activated in situ.
  • the transformation is preferably carried out in polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, ⁇ , ⁇ -dimethylformamide, N,N- dimethylacetamide, N-methylpyrolidinone or in an inert solvent such as dichloromethane, 1 ,2- dichloroethane, or 1 ,2-dimethoxyethane at temperatures ranging between room temperature and the reflux temperature of the solvent.
  • polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, ⁇ , ⁇ -dimethylformamide, N,N- dimethylacetamide,
  • Suitable leaving groups (Lg) in formula (III. a) and (lll.b), respectively include, but are not limited to: halogen, alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, alkyl phosphoante, halophosphate and various activated esters derived from the reaction of a free carboxylic acid with a peptide coupling reagent in the presence of an amine base (Chem. Rev., 2011 , 111 (1 1 ), 6557-6602).
  • the reaction can be achieved by acylation of the amine functionality in compounds of formula (II) using carboxylic acid derivatives ((lll.c)) or (lll.d), respectively, which may or may not be activated in situ.
  • the reaction is preferably carried out in polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, N-methylpyrolidinone or in an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane at temperatures ranging between room temperature and the reflux temperature of the solvent.
  • polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, N-methylpyr
  • Suitable leaving groups (Lg) in formula (III. c) and (lll.d), respectively include, but are not limited to: halogen, alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, alkyl phosphoante, halophosphate and various activated esters derived from the reac- tion of a free carboxylic acid with a peptide coupling reagent in the presence of an amine base ⁇ Chem. Rev., 2011 , 711 (1 1 ), 6557-6602).

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  • Organic Chemistry (AREA)
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Abstract

La présente invention concerne un composé N-acylimino représenté par la formule (I), dans laquelle X représente O ou S, en particulier O ; Cyc représente un radical Cyc-1 ou Cyc-2 (II) (III), D représente CH2 ou CH2-CH2, 1 ou 2 des atomes d'hydrogène pouvant être remplacé(s) par R4, Y représente O, S, CR5a R5b ou N-R5 ; Het représente un noyau hétérocyclique à 5 ou 6 chaînons lié à un atome de carbone ou lié à un atome d'azote, W1 -W2 -W3 -W4 représente un groupe à chaîne carbonée lié à N et C=N, de manière à former un hétérocycle saturé, insaturé ou partiellement insaturé à 5 ou 6 chaînons contenant de l'azote, W1, W2, W3 et W4 représentant chacun individuellement 1 CRvRw ; R1, R2 peuvent représenter un hydrogène, un halogène, un alkyle en C1-C6, etc. ; R3 représente un hydrogène, un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6, un cycloalkyle en C3-C8, un cycloalkyle en C3-C8-alkyle en C1-C4, etc. ; R4, R5, R5a, R5b représentent un hydrogène, un halogène, un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6, un cycloalkyle en C3-C8, un cycloalkyle en C3-C8-alkyle en C1-C4, etc. L'invention concerne également l'utilisation des composés N-acylamino hétérocycliques, de leurs stéréo-isomères, de leurs tautomères et de leurs sels pour lutter contre les nuisibles invertébrés. L'invention concerne en outre des procédés de lutte contre les ravageurs invertébrés, qui consistent à appliquer de tels composés.
PCT/EP2015/053559 2014-02-21 2015-02-20 Composes n-acylimino heterocycliques pour lutter contre les nuisibles invertebres Ceased WO2015124706A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10206397B2 (en) 2013-09-19 2019-02-19 Basf Se N-acylimino heterocyclic compounds
US10440953B2 (en) 2015-08-07 2019-10-15 Basf Se Control of pests in maize by ginkgolides and bilobalide
US11297837B2 (en) 2016-02-19 2022-04-12 Basf Se Pesticidally activi mixtures comprising anthranilamide compounds

Citations (5)

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Publication number Priority date Publication date Assignee Title
EP0639569A1 (fr) * 1991-03-11 1995-02-22 Nippon Soda Co., Ltd. Nouveau compose heterocyclique
EP2305658A1 (fr) * 2008-07-01 2011-04-06 Meiji Seika Kaisha, Ltd. Nouveau dérivé imino, procédé de fabrication de celui-ci et pesticide le comprenant
EP2591673A1 (fr) * 2010-07-07 2013-05-15 Meiji Seika Pharma Co., Ltd. Agent de lutte contre les organismes nuisibles
EP2633756A1 (fr) * 2012-02-29 2013-09-04 Meiji Seika Pharma Co., Ltd. Composition pour la contrôle des organismes nuisibles comprenant un derivé d'iminopyridine
WO2013144223A1 (fr) * 2012-03-30 2013-10-03 Basf Se Composés de pyrimidinylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0639569A1 (fr) * 1991-03-11 1995-02-22 Nippon Soda Co., Ltd. Nouveau compose heterocyclique
EP2305658A1 (fr) * 2008-07-01 2011-04-06 Meiji Seika Kaisha, Ltd. Nouveau dérivé imino, procédé de fabrication de celui-ci et pesticide le comprenant
EP2591673A1 (fr) * 2010-07-07 2013-05-15 Meiji Seika Pharma Co., Ltd. Agent de lutte contre les organismes nuisibles
EP2633756A1 (fr) * 2012-02-29 2013-09-04 Meiji Seika Pharma Co., Ltd. Composition pour la contrôle des organismes nuisibles comprenant un derivé d'iminopyridine
WO2013144223A1 (fr) * 2012-03-30 2013-10-03 Basf Se Composés de pyrimidinylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10206397B2 (en) 2013-09-19 2019-02-19 Basf Se N-acylimino heterocyclic compounds
US10440953B2 (en) 2015-08-07 2019-10-15 Basf Se Control of pests in maize by ginkgolides and bilobalide
US11297837B2 (en) 2016-02-19 2022-04-12 Basf Se Pesticidally activi mixtures comprising anthranilamide compounds

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