WO2016062680A1 - Composés n-acylimino hétérocycliques - Google Patents
Composés n-acylimino hétérocycliques Download PDFInfo
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- WO2016062680A1 WO2016062680A1 PCT/EP2015/074199 EP2015074199W WO2016062680A1 WO 2016062680 A1 WO2016062680 A1 WO 2016062680A1 EP 2015074199 W EP2015074199 W EP 2015074199W WO 2016062680 A1 WO2016062680 A1 WO 2016062680A1
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- alkyl
- pyridyl
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- 0 *c1nnc(*)[s]1 Chemical compound *c1nnc(*)[s]1 0.000 description 3
- PJCPKDYJAFXTQD-VXLYETTFSA-N CO/N=C(/C(/N=C1/N(Cc(cc2)cnc2Cl)CCN1)=O)\C#N Chemical compound CO/N=C(/C(/N=C1/N(Cc(cc2)cnc2Cl)CCN1)=O)\C#N PJCPKDYJAFXTQD-VXLYETTFSA-N 0.000 description 1
- BOIJBHNLWFZJPQ-ZNICKJPMSA-N CO/N=C(/C(/N=C1\SCCN1Cc(cc1)cnc1Cl)=O)\C#N Chemical compound CO/N=C(/C(/N=C1\SCCN1Cc(cc1)cnc1Cl)=O)\C#N BOIJBHNLWFZJPQ-ZNICKJPMSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Definitions
- the present invention relates to N-acylimino heterocyclic compounds, including their stereoisomers, tautomers and salts, and to compositions comprising such compounds.
- the invention 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 co ula 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 Ci-C 4 - acyl.
- the moiety electron withdrawing moiety Z is an electron withdrawing group such as alkoxcarbonyl, arylcarbonyl, heterocyclic carbonyl, Ci-C4-alkylsulfonyl, sulfamoyl or Ci-C 4 - acyl.
- 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
- R b 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.
- Chem. 2008, 51 , 4213-4218 describe triflouroacetylimino and pyrazinoylimino heterocyclic compounds of imidazolidine and thiazolidine derivatives, which shows insecticide activity.
- WO2013/129692 describes pesticidal nitrogen-containing heterocyclic derivatives having a 2- imino group represented by formula C,
- Ar is optionally substituted phenyl, aromatic 5- to 6-membered heterocyclyl, or 4- to 10- membered heterocycloalkyl
- A is a 5- to 10-membered partially unsaturated heterocycle having one or more nitrogen atoms as ring members and which has an imino group substituted with an R group at a position adjacent to the nitrogen atom present on the cycle
- Y represents hydrogen, halogen, hydroxyl, alkyi, haloalkyl, alkoxy, haloalkoxy, cyano or nitro.
- US 62/063,965 describes N-substituted acyl-imino compounds nitrogen containing heter- ocycles, which have a pesticidal activity.
- 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):
- X is O or S
- Het is a 5- or 6- membered carbon-bound or nitrogen-bound heterocyclic or heteroaro- matic ring, comprising 1 , 2, 3, 4 or 5 carbon atoms and 1 , 2 or 3 heteroatoms as ring members, which are independently selected from sulfur, oxygen and nitrogen, wherein the carbon, sulfur and nitrogen ring members can independently be partly or fully oxidized, and wherein each ring is optionally substituted by k identical or different substituents R 6 , wherein k is an integer selected from 0, 1 , 2, 3 and 4;
- W 1 represents O, S or NR w1 ;
- R w1 is selected from the group consisting hydrogen, cyano, nitro, SCN, Ci- Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or may be partly or fully halogenated and/or may optionally be substituted with 1 , 2 or 3 identical or different radicals R 7 ,
- each R v2 , R v3 independently from each other, is selected from the group consist- ing of hydrogen, cyano, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl and C2-Cio-alkynyl, wherein the carbon atoms of the aforementioned 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 ; each R v4 , R v5 are independently from each other selected from the group consisting of hydrogen, halogen, cyano, azido
- R v4 and R v5 may together be a C2-C5 alkylene chain forming a 3- to 7- membered partly saturated ring together with the carbon atoms R v4 and R v5 are boned to, where the alkylenen chain is unsubstituted or may car- ry 1 , 2, 3 or 4 identical or different radicals R 7 ; each R w2 , R w3 are independently from each other selected from the group consisting of hydrogen, cyano, nitro, SCN, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2- Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or may be partly or fully halogenated and/or may optionally be substituted with 1 , 2 or 3 identical or different radicals R 7 ,
- R 1 , R 2 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 aro- matic 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
- Het # represents 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 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
- Q irrespectively of its occurrence, is a single bond, Ci-C6-alkanediyl, C2-C6- alkenediyl, or C2-C6-alkynediyl,
- R 5 is selected from the group consisting of hydrogen, halogen, CN , Ci-C6-alkyl,
- phenyl 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 4 and R 5 together may also form with the nitrogen atom they are bound to, a 3-, 4-, 5 -or
- each of the carbon atoms of the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , and where the heterocylce has 1 or 2 non- adjacent identical or different heteroatoms or heteroatom moieties as ring memberes, which are selected from O, S, N and N-R 17c ,
- R 5a is selected from the group consisting of hydrogen, 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,
- 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 completely 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 iden- tical 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,
- 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 ;
- R 7a 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- halocycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkylmethyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl,
- 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; is selected from the group consisting of halogen, cyano, Ci-C6-alkyl, C3-C8- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be partly or completely halogenated, and/or be substituted with 1 , 2 or 3 identical or different radicals R 7 , OR 8 , NR 17a R 17b , S(0) n R
- 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,
- 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 7c which are bound at the same or adjacent carbon atoms, may form a spi- ro- or fused 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocy-oul or heterocyclic ring together with the carbon atoms to which the two R 7c are bound, 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 ; is selected from the group consisting of cyano, nitro, -SCN, SF 5 , Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, and wherein the carbon atoms of the last three aforementioned aliphatic and cycloaliphatic radicals may be partly or completely halo- genated and/or may carry a
- R 9a , 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, Cs-Cs-cycloalkoxy, C3-C8- halocycloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalky
- 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 heterocyclic 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 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
- 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;
- R16 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 Ci-C4-alkoxy,
- phenyl, benzyl and pyridyl wherein the last three radicals may be unsubstituted, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkoxy)carbonyl,
- R 16a d-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -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
- phenyl, benzyl and pyridyl wherein the last three radicals may be unsubstituted, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkoxy)carbonyl,
- R 17 independently of its occurrence, is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,
- Ci-C6-alkyl C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-Ci-C 4 - alkyl, Ci-C6-alkoxy, C 2 -C6-alkenyloxy, C 2 -C6-alkynyloxy, C 3 -C 8 -cycloalkoxy, C 3 -C 8 - cycloalkyl-Ci-C 4 -alkoxy, Ci-C6-alkylthio, wherein the 11 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 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, fe/ibutyld
- Ci-C6-alkyl C 2 -C6-alkenyl, C 2 -C6-alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-Ci- C 4 -alkyl, wherein the five last mentioned aliphatic and cyclo-aliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy,
- 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 ni- trogen 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 or nitrogen, and may optionally be substituted with halogen, Ci-C4-alkyl, Ci-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; or
- R 17c independently of its occurrence, 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, 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 carry 1 , 2 or 3 substituents selected from C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkoxy)carbonyl, (Ci-
- 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 iden- tical 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 19b 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, Cs-Cs-halocycloalkyl, C3- C8-cycloalkyl-Ci-C4-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 19b 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 and 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, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6 haloal
- 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, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the 5 last mentioned aliphatic and cycloaliphatic radicals may be un- substituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-
- phenyl, benzyl, pyridyl wherein the three last mentioned radicals may be unsubsti- tuted, 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 (C1-C6- alkoxy)carbonyl, is O, S or N-R 23 , is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Cs-Cs-cycloalkyl, wherein each of the four last mentioned radicals are un- substituted, partly or completely halogenated or carry 1 or 2 radicals R 7 , it being also possible for cycloalkyl radicals to carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups, the moieties Q a
- Het** represents 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 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, and
- Q a irrespectively of its occurrence, is a single bond, Ci-C6-alkanediyl, C2-C6- alkenediyl, or C2-C6-alkynediyl,
- Q b irrespectively of its occurrence, is Ci-C6-alkanediyl, C2-C6-alkenediyl, or C2-C6- alkynediyl,
- R 23 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-C8-cycloalkyl-Ci-C4- alkyl, wherein the 5 last mentioned aliphatic and cycloaliphatic radicals may be un- substituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy,
- phenyl, benzyl, pyridyl wherein the three last mentioned radicals may be unsubsti- tuted, 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 (C1-C6- alkoxy)carbonyl; the stereoisomers, tautomers and the salts thereof.
- Another embodiment of the invention relates to N-acylimino compounds of formula (I): wherein
- X is O or S
- Het is a 5 or 6 membered carbon-bound or nitrogen-bound heterocyclic or heteroaro- matic ring, comprising 2, 3, 4 or 5 carbon atoms and 1 , 2 or 3 heteroatoms as ring members, which are independently selected from sulfur, oxygen or nitrogen, wherein the sulfur and nitrogen ring members can independently be partly or fully oxidized, and wherein each ring is optionally substituted by k identical or different substituents R 6 , wherein k is an integer selected from 0, 1 , 2, 3 and 4;
- W 1 represents O, S or NR w1 ;
- W 2 -W 3 -W 4 represents a bivalent radical selected from -C(R v2 R w2 )-C(R v3 R w3 )-,
- R w1 is selected from the group consisting hydrogen, cyano, nitro, SCN, Ci-
- each R w2 , R w3 are independently from each other selected from the group consisting hydrogen, cyano, nitro, SCN, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2- Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the afore- mentioned aliphatic and cycloaliphatic radicals may be unsubstituted or may be partly or fully halogenated and/or may optionally be substituted with 1 , 2 or 3 identical or different radicals R 7 ,
- R 1 , R 2 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
- R 4 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl,
- Het # represents 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 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
- Q irrespectively of its occurrence, is a single bond, Ci-C6-alkandiyl, C2-C6- alkendiyl, or C2-C6-alkyndiyl,
- phenyl 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 4 and R 5 together may also form with the nitrogen atom they are bound to, a 3, 4, 5 or 6 membered saturated partially unsaturated N-bound heterocycle, wherein each of the carbon atoms of the heterocycle may be unsubstituted or may carry 1 ,
- heterocylce has 1 or 2 non-adjacent identical or different heteroatoms or heteroatom moieties as ring memberes, which are selected from O, S, N and N-R 17c , or
- R 5a is selected from the group consisting of hydrogen, CN , Ci-C6-alkyl, C2-C6- alkenyl, Ci-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein each of the five last mentioned radicals are unsubstituted, partly or completely halogenated,
- 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,
- phenyl, phenyl-Ci-C4-alkyl where the phenyl ring in the last two groups is optionally 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 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; is selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Cs-Cs- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be partly or completely halogenated, and/or be substituted with 1 , 2 or 3 identical or different radicals R 7 , OR 8 , NR 17a R 17b , S(0) n R
- 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,
- 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 7c which are bound at the same or adjacent carbon atoms, may form a spi- ro- or fused 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocy-oul or heterocyclic ring together with the carbon atoms to which the two R 7c are bound, 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 ; is selected from the group consisting of cyano, nitro, -SCN, SF 5 , Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, and wherein the carbon atoms of the last three aforementioned aliphatic and cycloaliphatic radicals may be partly or completely halo- genated and/or may carry a
- 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
- 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,
- 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, se- lected 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
- heterocyclic ring 7- membered saturated, partly saturated or unsaturated aromatic C-bound 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,
- halogen independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF 5 , Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-C10- alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, Ci-C6-alkyl, cyano, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci- C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino and di-(Ci-C6-alkyl)amino,
- 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 heterocyclic 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-Cs-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 last two radicals are unsubstituted or substituted with 1
- 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-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 C1-C4 alkoxy;
- Ci- C6-alkyl Ci-C6-haloalkyl
- Ci-C6-alkoxy Ci-C6-alkoxy
- C1-C6 haloalkoxy C1-C6 haloalkoxy
- (Ci-C6-alkoxy)carbonyl Ci-C6-alkyl)amino or di-(Ci-C6-alkyl)amino
- ?16 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, 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,
- Ci- C6-alkyl Ci-C6-haloalkyl
- Ci-C6-alkoxy Ci-C6-alkoxy
- C1-C6 haloalkoxy C1-C6 haloalkoxy
- (Ci-C6-alkoxy)carbonyl Ci-C6-alkyl)amino or di-(Ci-C6-alkyl)amino
- Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-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 C1-C4 alkoxy,
- Ci- C6-alkyl Ci-C6-haloalkyl
- Ci-C6-alkoxy C1-C6 haloalkoxy
- (Ci-C6-alkoxy)carbonyl Ci-C6-alkyl)amino or di-(Ci-C6-alkyl)amino
- independently of its occurrence is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,
- 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 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, fe/ibutyldimethylsilyl,
- Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci- C4-alkyl, wherein the five last mentioned aliphatic and cyclo-aliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy,
- phenyl, benzyl, pyridyl, phenoxy wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents 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 or nitrogen, and may optionally be substituted with halogen, Ci-C4-alkyl, Ci-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; or
- R 17c independently of its occurrence, 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, 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 carry 1 , 2 or 3 substituents selected from C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkoxy)carbonyl, (Ci- C6-alkyl)amino or di-(Ci-C6-alkyl)amino;
- 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
- R 19a , R 19b 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, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 - C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 - C 8 -cycloalkyl,
- 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 19a and R 19b 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, se- lected 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, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl,
- 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, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the 5 last mentioned aliphatic and cycloaliphatic radicals may be un- substituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-
- phenyl, benzyl, pyridyl wherein the three last mentioned radicals may be unsubsti- tuted, 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 (C1-C6- alkoxy)carbonyl,
- Y' is O, S or N-R 23 ,
- R 22 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Cs-Cs-cycloalkyl, wherein each of the four last mentioned radicals are un- substituted, partly or completely halogenated or carry 1 or 2 radicals R 7 , it being also possible for cycloalkyl radicals to carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups, the moieties Q a -phenyl, Q b -0-phenyl and Q b -S-phenyl, where the phenyl ring is optionally substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 , and the moieties O-Hel** Q ⁇ O-Het" and Q k -S-Het** where
- Het** represents 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 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
- Q a irrespectively of its occurrence, is a single bond, Ci-C6-alkandiyl, C2-C6- alkendiyl, or C2-C6-alkyndiyl,
- Q b irrespectively of its occurrence, is Ci-C6-alkandiyl, C2-C6-alkendiyl, or C2-C6- alkyndiyl,
- R 23 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-C8-cycloalkyl-Ci-C4- alkyl, wherein the 5 last mentioned aliphatic and cycloaliphatic radicals may be un- substituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy,
- phenyl, benzyl, pyridyl wherein the three last mentioned radicals may be unsubsti- tuted, 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 (C1-C6- alkoxy)carbonyl; the stereoisomers, tautomers and the salts thereof.
- 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 stereoisomers, 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 properties such as stability or show different biological properties such as activities.
- the present inven- tion 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 veterinarily 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 carbonate, 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 particular 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 alkynyl is also termed haloalkynyl
- partially or fully halogenated alkoxy is also termed haloalkoxy
- partially or fully halogenated alkylthio also referred to as C n -C m -alkylsulfanyl
- haloalkthio partially or fully halogenated alkylsulfinyl
- partially or fully halogenated alkylsulfonyl is also termed haloalsulfonyl
- partially or fully halogenated cycloalkylalkylalkyl is also termed haloalkyl
- Ci-C m -alkyl refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g.
- 1 to 10 carbon atoms (Ci-Cio-alkyl), preferably 1 to 6 carbon atoms (C1-C6- alkyl), 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-dimethylbuty
- Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.
- Ci-C m -alkandiyl refers to a linear or branched saturated bival- net hydrocarbon group having 1 to m, e.g. 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, for example methylen, ethan-1 ,1 -diyl, ethan-1 ,2-diyl, propan-1 ,1 -diyl, propan-1 ,2-diyl, propan- 1 ,3-diyl, propan-2,2-diyl, butan-1 ,1 -diyl, butan-1 ,2-diyl, butan-2,3-diyl, butan-2,2-diyl, butan-1 ,3- diyl, butan-1 ,4-diyl, pentan-1 ,1 -diyl, pentan-2,2-diyl, pentan-3,3-diyl, pent
- linear Ci-C6-alkandiyl refers to a linear saturated bivalnet hydrocarbon group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, for example methylen, ethan-1 ,2-diyl, propan-1 ,3-diyl, butan-1 ,4-diyl, pentan-1 ,5-diyl and hexan-1 ,6-diyl.
- Ci-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, trifluoromethyl, 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, penta
- Ci-Cio-haloalkyl in particular comprises Ci-C2-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hy- drogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 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.
- Ci-C m -haloalkoxy refers to straight-chain or branched alkyl groups having n to m carbon atoms, e.g.
- Ci-C m -alkoxy is a Ci-C m -alkyl group, as defined above, attached via an oxygen atom. 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.
- Ci-C m -alkylthio is a Ci-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, ethylthio, 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 in- eludes 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 isomers thereof.
- Ci-C m -haloalkyloxy (also referred to as Ci-C m -haloalkoxy) is a Ci-C m -haloalkyl group, as defined above, attached via an oxygen atom.
- Ci-C2-haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoro- methoxy, 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 pentafluoroethoxy.
- Ci-C2-haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy,
- Ci-C m -haloalkylthio is a Ci-C m -haloalkyl group, as defined above, attached via a sulfur atom.
- 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-difluoroethyl
- 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, respectively.
- C2-C m -alkendiyl refers to linear or branched mono-unsaturated bivalnet hydrocarbon group having 2 to m, e.g. 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms, for example ethen-1 ,1 -diyl, ethen-1 ,2-diyl, prop-1 -en-1 ,1 -diyl, prop-1 -en-1 ,2-diyl, prop-2- en-1 ,1 -diyl, prop-2-en-1 ,2-diyl, propen-1 ,3-diyl, but-1 -en-1 ,1 -diyl, but-1 -en-1 ,2-diyl, but-1 -en-1 ,3- diyl, but-2-en-1 ,1 -diyl, but-2-en-1 ,2-diyl, but-3-en-1 ,1 -diyl, but-3-en-1
- C2-C m -haloalkenyl refers to C2-C m -alkenyl, where some or all of the hydrogen 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
- 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 tri- pie 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 hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
- Examples of C2-C m -haloalkynyl 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 par- ticular 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, cy- clopropyl 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 defined 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,
- Examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n- butylcarbonyl and the like.
- Ci-C6-haloalkylcarbonyl a Ci-C6-haloalkylcarbonyl
- Ci-C4-haloalkylcarbonyl Ci-C4-haloalkylcarbonyl
- Examples are trifluoromethylcarbonyl, 2,2,2-trifluoroethylcarbonyl and the like.
- 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 radical refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic.
- the heterocyclic radical may be attached to the remainder of the molecule 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 bivalent 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)-,
- 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 , Het-3 and Het-24, in particular 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 .
- 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-3, Het-1 1 a and Het-24,
- Ci-C4- alkyl such as methyl or ethyl
- Ci-C4-alkoxy such as methoxy or ethoxy
- C1-C4- haloalkoxy such as difluoromethoxy or trifluoromethoxy
- 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 C1-C2- haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl
- 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 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 C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl
- 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 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-difluoroethyl, 2,2,2- trifluoroe
- 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 wherein
- 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
- a special embodiment of the radical Het-1 1 a is 2-chlorothiazol-5-yl, i.e. R 6a is chlorine.
- 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-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-C
- Het is a radical of formula Het-3, 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, 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,
- 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, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl.
- radicals R 1 and R 2 are hydrogen. Even more preferred the radicals R 1 and R 2 are either both hydrogen or one of R 1 and R 2 is hydrogen, while the other is methyl.
- R 3 is selected from the group consisting of hydrogen, NO2, CN, Ci-C6-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C6-alkynyl, which is unsubstituted, partly or completely halogenated or carries a radical R 7d ;
- R 7a , R 7d , R 8 , R 9a , R 9 , R 15 , R 16 , R 17 , R 17a , R 17 , R 21 and R 22 are as defined above and have in particular one of the following meanings:
- R 7a is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, phenyl, pyridyl, pyridylmethyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and
- Ci-C6-alkyl which is subsituted by 1 or 2 radicals selected from phenyl, pyridyl, OR 16 ,
- R 7a is in particular selected from the group consisting of is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, Ci-C6-alkyl, which is subsituted by 1 radical selected from phenyl, pyridyl, cyano, C1-C4- alkoxy, Ci-C4-alkoxycarbonyl and C3-C4-cycloalkyl;
- R 7d is in particular selected from the group consisting of Ci-C4-alkyl, Ci-C2-haloalkyl, phenyl, C3-C6-cycloalkyl and trimethylsilyl;
- Ci-C6-alkyl is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated,
- R 8 is in particular selected from the group consisting of Ci-C4-alkyl, C3-C4- cycloalkyl, C3-C4-cycloalkylmethyl, benzyl and pyridylmethyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,
- Ci-C4-alkyl which is substituted by 1 or 2 radicals selected from the group consisting of cyano, Ci-C4-alkoxy, Ci-C4-alkylamino and di-Ci-C4-alkylamino;
- R 9b is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3- C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last two mentioned groups to be unsubstituted, partly or completely halogenated, one of R 9a , R 9b may also be Ci-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6- cycloalkylmethoxy,
- R 9a together with R 9b forms a C4-C6 alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and Ci-C4-alkyl;
- R 9a , R 9b are in particular selected from the group consisting of are selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and C3-C4- cycloalkylmethyl, one of R 9a , R 9b may also be Ci-C4-alkoxy, C3-C4-cycloalkoxy or C3-C6- cycloalkylmethoxy,
- R 15 is in particular selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C3- C4-cycloalkyl and C3-C4-cycloalkylmethyl;
- ?16 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated, and where R 16 is in particular selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C4-cycloalkyl and C3-C4- cycloalkylmethyl;
- R 17 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and where R 17 is in particular selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C4-cycloalkyl and C3-C4- cycloalkylmethyl;
- R 17a , R 17b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C3- C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, or R 17a together with R 17b forms a C4-C6 alkylene chain and form a 5-, 6- or 7-membered saturated, 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 radi- cals selected from halogen and Ci-C4-alkyl
- R 17a , R 17b are in particular selected from the group consisting of are selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and C3-C4- cycloalkylmethyl;
- R 21 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated;
- R 22 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated
- Ci-C6-alkyl which is subsituted by 1 or 2 radicals selected from phenyl, pyridyl, OR 8 ,
- phenyl and pyridyl it being possible for phenyl and pyridiyl to be unsubstituted, partly or completely halogenated and/or carry 1 , 2 or 3 substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl and R 22 is in particular selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated,
- R 8 is selected from the group consisting of Ci-C4-alkyl, C3-C4-cycloalkyl, C3-C4- cycloalkylmethyl, benzyl and pyridylmethyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, Ci-C4-alkyl, which is substituted by 1 or 2 radicals selected from the group consisting of cyano, Ci-C4-alkoxy, Ci-C4-alkylamino, di-Ci-C4-alkylamino;
- R 17a , R 17b are selected from the group consisting of are selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and C3-C4-cycloalkylmethyl.
- R 7a is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6- cycloa I kyl , C3-C6-cycloa I kyl methyl ,
- Ci-C6-alkyl which is subsituted by 1 radical selected from phenyl, pyridyl, cyano, C1-C4- alkoxy, Ci-C4-alkoxycarbonyl and C3-C4-cycloalkyl,
- R 7d is selected from the group consisting of Ci-C4-alkyl, Ci-C2-haloalkyl, phenyl, C3-C6- cycloalkyl and trimethylsilyl;
- R 8 is selected from the group consisting of Ci-C4-alkyl, C3-C4-cycloalkyl, C3-C4- cycloalkylmethyl, benzyl and pyridylmethyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,
- Ci-C4-alkyl which is substituted by 1 or 2 radicals selected from the group consisting of cyano, Ci-C4-alkoxy, Ci-C4-alkylamino, di-Ci-C4-alkylamino;
- R 9a , R 9b is selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and
- R 9a , R 9b may also be Ci-C4-alkoxy, C3-C4-cycloalkoxy or
- R 15 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C4-cycloalkyl and C3-C4-cycloa I kyl m ethyl ;
- R 16 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C4-cycloalkyl and C3-C4-cycloa I kyl m ethyl ;
- R 17 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C4-cycloalkyl and C3-C4-cycloalkylmethyl;
- R 17a , R 17b are selected from the group consisting of are selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and C3-C4-cycloalkylmethyl;
- R 21 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C4-cycloalkyl and C3-C4-cycloa I kyl m ethyl ;
- R 22 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated,
- R 8 is selected from the group consisting of Ci-C4-alkyl, C3-C4-cycloalkyl, C3-C4- cycloalkylmethyl, benzyl and pyridylmethyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, Ci-C4-alkyl, which is substituted by 1 or 2 radicals selected from the group consisting of cyano, Ci-C4-alkoxy, Ci-C4-alkylamino, di-Ci-C4-alkylamino;
- R 17a , R 17b are selected from the group consisting of are selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and C3-C4-cycloalkylmethyl.
- a particular group (1 ) of embodiments relates to compounds of formula (I), their stereoi- somers, tautomers and salts wherein R 3 is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, C1-C6- haloalkyl, in particular Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl
- a particular group (1 ') of embodiments relates to compounds of formula (I), their stereoisomers, tautomers and salts wherein R 3 is selected from the group consisting of Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci-C6-haloalkyl, in par- ticular Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C3-C6- cycloalkyi, such as cyclopropyl or cyclobutyl, C3-C6-halocycloalkyl, such as 1 -fluorocycloprop
- R 7a , R 8 , R 9a , R 9b and R 22 are as defined herein and wherein R 7a , R 8 , R 9a , R 9b and R 22 have in particular the following meanings:
- R 7a is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6- cycloa I kyl , C3-C6-cycloa I kyl methyl ,
- Ci-C6-alkyl which is subsituted by 1 radical selected from phenyl, pyridyl, cyano, C1-C4- alkoxy, Ci-C4-alkoxycarbonyl and C3-C4-cycloalkyl,
- R 8 is selected from the group consisting of Ci-C4-alkyl, C3-C4-cycloalkyl, C3-C4- cycloalkylmethyl, benzyl and pyridylmethyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,
- Ci-C4-alkyl which is substituted by 1 or 2 radicals selected from the group consisting of cyano, Ci-C4-alkoxy, Ci-C4-alkylamino, di-Ci-C4-alkylamino;
- R 9a , R 9b is selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and
- R 9a , R 9b may also be Ci-C4-alkoxy, C3-C4-cycloalkoxy or
- R 22 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated,
- R 8 is selected from the group consisting of Ci-C4-alkyl, C3-C4-cycloalkyl, C3-C4- cycloalkylmethyl, benzyl and pyridylmethyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, Ci-C4-alkyl, which is substituted by 1 or 2 radicals selected from the group consisting of cyano, Ci-C4-alkoxy, Ci-C4-alkylamino, di-Ci-C4-alkylamino; R 17a , R 17b are selected from the group consisting of are selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and C3-C4-cycloalkylmethyl.
- R 3 is CN.
- R 7a is as defined above and in particular selected from the group consisting of Ci-C6-alkyl, C3- C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and where R 7a is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, or C1-C4- haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluorome- thyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, even more especially Ci-C2-alkyl such as methyl and ethyl;
- R 8 is as defined above and preferably is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated, and where R 8 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, C1-C4- haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluorome- thyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl;
- R 9a , R 9b are is as defined above and preferably selected from the group consisting of
- R 21 is as defined above and preferably selected from the group consisting of Ci-C6-alkyl, C3- C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated and where R 22 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, C1-C4- haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl.
- R 22 is as defined above and preferably selected from the group consisting of Ci-C6-alkyl, C3- C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated and where R 22 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, C1-C4- haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, even more especially Ci-C2-alkyl such as methyl or ethyl.
- Ci-C4-alkyl such
- R 8 is as defined above and preferably is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated, and where R 8 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, C1-C4- haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl;
- R 9a , R 9b are is as defined above and preferably selected from the group consisting of
- R 21 is as defined above and preferably selected from the group consisting of Ci-C6-alkyl, C3- C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzylyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and where R 21 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci- C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl.
- R 7a is as defined above and preferably selected from the group consisting of of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and where R 7a is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, or Ci-C4-haloalkyl, Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, even more especially Ci-C2-alkyl such as methyl and ethyl;
- R 22 is as defined above and preferably selected from the group consisting of Ci-C6-alkyl, C3- C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated and where R 22 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, C1-C4- haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, even more especially Ci-C2-alkyl such as methyl or ethyl.
- Ci-C4-alkyl such
- Y is in particular O or S and especially O.
- Y may also be NR 5 .
- Y may also be CHR 5a .
- the radical R 4 is in particular selected from the group consisting of the groups i) to xiii), each of which representing a particular group of embodiments:
- C3-C6-cycloalkyl which is unsubstituted, partially or completely halogenated and/or carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
- R 7a is as defined above and preferably selected from the group consisting of selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and where R 7a is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci-C4-haloalkyl, es- pecially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl;
- Ci-C6-alkyl is as defined above and preferably selected from the group consisting of selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated, and where R 8 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci-C4-haloalkyl, especially C1-C2- fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl;
- Ci-C6-alkyl is as defined above and preferably selected from the group consisting of selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and where R 15 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl;
- Ci-C6-alkyl is as defined above and preferably selected from the group consisting of selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and where R 17 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl;
- R 17a together with R 17b forms a C4-C6 alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and Ci-C4-alkyl, examples being, examples being 1 -piperidinyl, 4-morpholinyl, 1 -pyrrolidinyl, 1 -piperazinyl and 4-methyl
- R 18 is as defined above and in particular selected from the group consisting of Ci-C6-alkyl, C3- C6-cycloalkyl, C3-C6-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated,
- R 19a , R 19b are as defined above and in particular selected from the group consisting of
- Ci-C6-alkyl C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, or R 19a together with R 19b forms a C4-C6 alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and Ci-C4-alkyl;
- R 20 is as defined above and in particular selected from the group consisting of Ci-C6-alkyl, C3- C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated.
- radicals Q and Q' are as defined above and
- the radical Het # is as defined above and
- Het # in particular represents a 5- or 6-membered saturated, partially unsaturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the aromatic 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 more particularly Het # is 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, oxa- zolyl, thiazolyl, pyrazolyl, imidazolyl, isothiazolyl or isoxazolyl, where hetaryl is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 .
- the radical R 10 is selected from halogen, CN, Ci-C4-alkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkyl, Ci- C4-alkoxy, and Ci-C4-haloalkoxy.
- the radical R 4 is more particularly selected from the group consisting of the groups i), ii), iii), iv), vii), viii), ix), and xi), even more particularly selected from the group consisting of the groups ii), iii), iv), vii), viii), ix), and xi), each of which representing a par- ticular group of embodiments:
- R 8 is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl,
- R 17a , R 17b are as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted, partly or completely halogenated;
- R 19a , R 19b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6- cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated;
- Ci-C4-alkyl groups viii) is as defined above and in particular C3-C6-cycloalkyl, which is unsubstituted, partial- ly or completely halogenated and/or carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups, ix) is as defined above and in particular phenyl or benzyl, where the phenyl ring is optionally substituted with one or more, e.g.
- R 10 1 , 2, 3, 4 or 5 identical or different substituents R 10 , 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;
- Het # is as defined above and in particular Het # or Chb-Het* where Het # is as defined above and in particular represents a 5- or 6-membered saturated, partially unsaturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and 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, C1-C4- haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy.
- the radical R 4 is even more particularly selected from the group consisting of Chb-phenyl, Chb-pyridyl or Chb-thienyl, where phenyl, pyridyl and thienyl are un- substituted or carry 1 , 2 or 3 identical or different substituents R 10 , where R 10 is as defined above and especially selected from halogen, such as fluorine, chlorine or bromine, CN, C1-C4- alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- halogen such as fluorine, chlorine or bromine
- CN C1-C4- alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- Ci-C4-haloalkyl especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, and Ci-C4-haloalkoxy, such as difluo- romethoxy or trifluoromethoxy.
- radical R 4 is also even more particularly selected from the group consisting of
- Ci-C6-alkyl which is unsubstituted, partially or completely halogenated or substituted by one radical selected from CN, C3-C6-cycloalkyl, Ci-C4-alkoxy and Ci-C4-alkoxycarbonyl, and
- radical R 4 is also even more particularly C2-C6-alkenyl, which is partly or completely halogenated.
- the radical R 4 is also even more particularly hydrogen.
- the radical R 5 is as as defined above and in particular selected from the group consisting of
- R 10 is as defined above and in particular selected from the group consisting of halogen, CN, Ci-C4-alkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy.
- the radical R 5 is especially selected from the group consisting of hydrogen and Ci-C6-alkyl.
- the radicals R 4 and R 5 together with the nitrogen atom they are bound to may also form, a 3-, 4-, 5- or 6- membered saturated, partially unsaturated or aromatic N-bound heterocycle, wherein each of the carbon atoms of the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , and where the heterocylce has 1 or 2 non-adjacent identical or different heteroatoms or heteroatom moieties as ring memberes, which are selected from O, S, N and N-R 17c .
- R 7b is in particular selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
- R 17c is in particular selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
- N-bound heterocycles which R 4 and R 5 together with the nitrogen atom they are bound to may form, include 1 -pyrrolyl, 1 -pyrrolidinyl, 1 -piperidinyl, 4-morpholinyl, 1 -piperazinyl and 4-methyl-1 - piperazinyl, where the carbon atoms of the radicals may carry 1 , 2, 3 or 4 radicals R 7b .
- a further particular group (3) of embodiments relates to compounds of formula (I), their stereoisomers, tautomers and salts wherein R 3 and R 4 together form a bivalent radical, selected from the group consisting of C2-Cs-alkandiyl, C2-Cs-alkendiyl, Q"-Ci-C4-alkandiyl and Q"-C2-C4- alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R 7c , and wherein Q" is selected from O and S and bound to the carbon atom, which carries R 3 .
- a further particular group (3a) of embodiments relates to compounds of formula (I), their stereoisomers, tautomers and salts wherein R 3 and R 4 together form a bivalent radical, selected from the group consisting of Q"-Ci-C4-alkandiyl and Q"-C2-C4-alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R 7c , and wherein Q" is selected from O and S and bound to the carbon atom, which carries R 3 .
- R 3 and R 4 together form, in particular a bivalent radical O- CH2CH2, wherein 1 , 2, 3 or 4 hydrogen atoms of CH2CH2 may be replaced by R 7c .
- a further particular group (3b) of embodiments relates to compounds of formula (I), their stereoisomers, tautomers and salts wherein R 3 and R 4 together form a bivalent radical, selected from the group consisting of C2-C4-alkandiyl and C2-C4-alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R 7c .
- R 3 and R 4 together form, in particular a bivalent radical CH2CH2, wherein 1 , 2, 3 or 4 hydrogen atoms of CH2CH2 may be replaced by R 7c .
- These compounds are hereinafter termed compounds of group (3b') embodiments.
- the radical Y is in particular selected from the group consisting of O, S and NH.
- Y is in particular O.
- Y may also be CHR 5a , in particular CH2.
- Y 1 is O, S, CHR 5a or N- R 5 , where R 5a and R 5a are as defined herein and where R 7A , R 7B , R 7D and R 7E are hydrogen or have one of the meanings given for R 7c .
- the radical Y 1 is in particular selected from the group consisting of O, S and NH. In the compounds of formula l-A, the radical Y 1 is in especially O. In the compounds of formula l-A, the radical Y 1 may also be CHR 5a , in particular Chb. In the compounds of formula l-A, the radicals R 7A , R 7B , R 7D and R 7E are in particular as follows:
- R 7A and R 7B are, independently of each other, selected from the group consisting of hy- drogen, 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 un- substituted, partly or completely halogenated,
- a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aro- matic 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 7A , R 7B , R 7D and R 7E are more particularly as follows:
- R 7A and R 7B are, independently of each other, selected from the group consisting of hy- drogen, Ci-C6-alkyl and Ci-C6-haloalkyl, and where R 7A and R 7B are in particular both hydrogen;
- R 7D and R 7E are, independently of each other, selected from the group consisting of hydrogen, cyano, azido, nitro, -SCN, SF 5 , Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6 haloalkynyl,
- 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 7A , R 7B , R 7D and R 7E are even more particu- larly as follows:
- R 7A and R 7B are, independently of each other, selected from the group consisting of hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl, and where R 7A and R 7B are in particular both hydrogen;
- R 7D is selected from the group consisting of hydrogen, Ci-C4-alkyl and C1-C4- haloalkyl;
- R 7E is selected from the group consisting of hydrogen cyano, Ci-C6-alkyl, C1-C6- haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl,
- phenyl and phenyl-Ci-C4-alkyl where the phenyl ring in the last two groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 .
- R 7A , R 7B , R 7D and R 7E are especially as follows:
- R 7A and R 7B are hydrogen
- R 7D is selected from the group consisting of hydrogen, Ci-C4-alkyl and C1-C4- haloalkyl;
- R 7E is selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, Ci-
- C6-haloalkyl Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Ci-C6-alkoxycarboyl,
- phenyl and phenyl-Ci-C4-alkyl such as benzyl or 1 -phenethyl, where the phe- nyl ring in the last two groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 .
- R 17a and R 17b are as defined above and in particular as follows:
- Ci-C6-alkyl is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated, and where R 8 is more particularly C1-C4- alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci-C4-haloalkyl, especially C1-C2- fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl;
- R 9b are selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, or R 9a together with R 9b forms a C4-C6 alkylene chain and form a 5-, 6- or 7-membered saturated 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 and Ci-C4-alkyl, examples being 1-piperidinyl, 4-morpholinyl,
- R 9a , R 9b are, independently of each other, in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, and phenyl, which is unsubstituted, partly or completely halogenated;
- halogen such as fluorine, chlorine or bromine
- CN Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- Ci-C4-alkylcarbonyl such as acetyl, Ci-C4-haloalkyl, especially C1-C2- fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy or eth- oxy, and Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, Ci-C4-alkylthio, such as methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl,
- Ci-C4-alkylsulfonyl such as methyl- sulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, 2-butylsulfonyl, isobutylsulfonyl, or tert.-butylsulfonyl
- Ci-C4-haloalkylthio especially Ci-C2-fluoroalkylthio, such as fluoromethylsulfanly, difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1- difluoroethylsulfanyl, 2-fluoroethylsulfanyl, 2,2-difluoroeth
- R 12 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-C2-haloalkoxy;
- R 14 are selected from the group consisting of hydrogen, fluorine, chlorine, CN, C1-C4- alkyl, such as methyl, ethyl, n-propyl or n-butyl, C3-C6-cycloalkyl, such as cyclopropyl, cy- clobutyl or cyclopentyl, and phenyl.
- ⁇ is selected from the group consisting of hydrogen, 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, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluorome- thyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroe
- Ci-C4-alkyl is selected from the group consisting of 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-difluoroethyl or 2,2,2-
- R 17 is selected from the group consisting of selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and where R 17 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci- C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl; R 17a , R 17b are selected from the group consisting of selected from the group consisting of hydrogen, Ci-C6-alky
- a particular group (1 a) of embodiments relates to compounds of the formula (I), where Y is O and where R 3 is as defined for groups (1 ) or (1 ') of embodimens and R 3 is in particular hydrogen.
- R 4 is as defined above and in particular selected from the group of radicals of groups i) to vi) and viii) to xii) and especially from the radicals of groups ii), iii), iv), viii), ix), and xi), as defined above and where
- R 7a is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl,
- R 8 is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl,
- R 17a , R 17b are as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted, partly or completely halogenated;
- viii) is in particular C3-C6 cycloalkyl, which is unsubstituted, partially or completely halogenated and/or carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
- ix) is in particular phenyl or benzyl, where the phenyl ring is optionally substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 , where the radical R 10 , irrespective of its occurrence, is in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- halogen such as fluorine, chlorine or bromine
- CN Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- Ci-C4-haloalkyl especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, and Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, Ci-C4-alkylthio, such as methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl, isobutylsulfanyl, or
- xi) is in particular Het # or Chb-Het*
- Het # is as defined above and in particular represents a 5- or 6-membered saturated, partially unsaturated or 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/or 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, C1-C4- alkylcarbonyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy.
- the radical R 4 is even more particularly selected from the group consisting of Chb-phenyl, Chb-pyridyl or Chb-thienyl, where phenyl, pyridyl and thienyl are unsubstituted or carry 1 , 2 or 3 identical or different substituents R 10 , where R 10 is as defined above and in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- halogen such as fluorine, chlorine or bromine
- CN Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- Ci-C4-alkylcarbonyl such as acetyl, Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, and Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, Ci-C4-alkylthio, such as methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl, isobutylsulfanyl, or
- Ci-C4-haloalkylthio especially Ci-C2-fluoroalkylthio, such as fluoromethylsulfanly, difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2-fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl and Ci-C4-haloalkylsulfonyl, especially Ci- C2-fluoroalkylsulfonyl, such as fluoromethylsulfonly, difluoromethylsulfonyl, trifluoromethyl- sulfonyl, 1 ,1 -difluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-diflu
- Ci-C4-alkylcarbonyl such as acetyl
- Ci-C4-haloalkyl especially C1-C2- fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl
- Ci-C4-alkoxy such as methoxy or ethoxy
- C1-C4- haloalkoxy such as difluoromethoxy or trifluoromethoxy.
- radical R 4 is also even more particularly selected from the group consisting of
- Ci-C6-alkyl which is unsubstituted, partially or completely halogenated or substituted by one radical selected from CN, C3-C6 cycloalkyl, Ci-C4-alkoxy and Ci-C4-alkoxycarbonyl, - C3-C6 cycloalkyl, which is unsubstituted, partly or completely halogenated, and
- a particular group (1 b) of embodiments relates to compounds of the formula (I), where Y is NR 5 and where R 3 is as defined for groups (1 ) or (1 ') of embodimens and R 3 is in particular hydrogen.
- R 4 is as as defined above and in particular selected from the group of radicals of groups i) to to xii) and especially from the radicals of groups ii), iii), iv), vii), viii), ix), and xi), as defined above and where
- R 7a is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl,
- R 8 is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl
- R 17a , R 17b are as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted, partly or completely halogenated;
- R 19a , R 19b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6- cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated;
- viii) is in particular C3-C6 cycloalkyi, which is unsubstituted, partially or completely halogenated and/or carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
- ix) is in particular phenyl or benzyl, where the phenyl ring is optionally substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 , 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, Ci-C4-alkoxy, and C1-C4- haloalkoxy;
- xi) is in particular Het # or Chb-Het*
- Het # is as defined above and in particular represents a 5- or 6-membered saturated, partially unsaturated or 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/or 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 the group consisting of halogen, such as fluorine, chlorine or bromine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- halogen such as fluorine
- Ci-C4-alkylcarbonyl such as acetyl, Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, and C1-C4- haloalkoxy, such as difluoromethoxy or trifluoromethoxy, Ci-C4-alkylthio, such as methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n- butylsulfanyl, 2-butylsulfanyl, isobutylsulfanyl,
- R 5 is as as defined above and in particular selected from the group consisting of
- R 10 is as defined above and in particular selected from the group consisting of halogen, CN , Ci-C4-alkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy.
- R 5 is especially selected from the group consisting of hydrogen and Ci-C6-alkyl.
- radicals R 4 and R 5 together with the nitrogen atom they are bound to may also form, a 3, 4, 5 or 6 membered saturated, partially unsaturated or aromatic N-bound heterocycle, wherein each of the carbon atoms of the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , and where the heterocylce has 1 or 2 non-adjacent identical or different heteroatoms or heteroatom moieties as ring memberes, which are selected from O, S, N and N-R 17c .
- R 7b is in particular selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
- R 17c is in particular selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
- N-bound heterocycles which R 4 and R 5 together with the nitrogen atom they are bound to may form, include 1 -pyrrolyl, 1 -pyrrolidinyl, 1 - piperidinyl, 4-morpholinyl, 1 -piperazinyl and 4-methyl-1 -piperazinyl, where the carbon atoms of the radicals may carry 1 , 2, 3 or 4 radicals R 7b .
- a particular group (1 c) of embodiments relates to compounds of the formula (I), where Y is a single bond and where R 3 is as defined for group (1 ) or (V) of embodimens and R 3 is in par- ticular hydrogen.
- R 4 is as as defined above and in particular selected from the group of radicals of groups i) to vi) and viii) to xii) and especially from the radicals of groups ii), iii), iv), viii), ix), and xi), as defined above and where
- R 7a is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl
- R 8 is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl
- R 17a , R 17b are as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted, partly or completely halogenated;
- viii) is in particular C3-C6 cycloalkyl, which is unsubstituted, partially or completely halogenated and/or carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
- ix is in particular phenyl or benzyl, where the phenyl ring is optionally substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 , 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, Ci-C4-alkoxy, and C1-C4- haloalkoxy;
- xi) is in particular Het # or Chb-Het*
- Het # is as defined above and in particular represents a 5- or 6-membered saturat- ed, partially unsaturated or unsaturated aromatic heterocyclic ring comprising
- 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 compris- ing 1 , 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or 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, C1-C4- alkylcarbonyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy.
- R 4 is as as defined above and in particular selected from the group of radicals of groups i) to vi) and viii) to xii) and especially from the radi- cals of groups ii), iii), iv), viii), ix), and xi), as defined above and where
- R 7a is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl,
- R 8 is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl,
- R 17a , R 17b are as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted, partly or completely halogenated;
- viii) is in particular C3-C6 cycloalkyl, which is unsubstituted, partially or completely halo- genated and/or carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
- ix) is in particular phenyl or benzyl, where the phenyl ring is optionally substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 , 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, Ci-C4-alkoxy, and C1-C4- haloalkoxy;
- xi) is in particular Het # or Chb-Het*
- Het # is as defined above and in particular represents a 5- or 6-membered saturated, partially unsaturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are selected from oxygen, ni- trogen 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/or 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, C1-C4- alkylcarbonyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy.
- the radical R 4 is even more particu- larly selected from the group consisting of Chb-phenyl, Chb-pyridyl or Chb-thienyl, where phenyl, pyridyl and thienyl are unsubstituted or carry 1 , 2 or 3 identical or different substituents R 10 , where R 10 is as defined above and in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- halogen such as fluorine, chlorine or bromine
- CN Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- Ci-C4-alkylcarbonyl such as acetyl, Ci-C4-haloalkyl, es- pecially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, and Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, Ci-C4-alkylthio, such as methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl, isobutylsul
- Ci-C4-haloalkylthio especially Ci-C2-fluoroalkylthio, such as fluoromethylsulfanly, difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2-fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl and Ci-C4-haloalkylsulfonyl, especially Ci- C2-fluoroalkylsulfonyl, such as fluoromethylsulfonly, difluoromethylsulfonyl, trifluoromethyl- sulfonyl, 1 ,1 -difluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-diflu
- Ci-C4-alkylcarbonyl such as acetyl
- Ci-C4-haloalkyl especially C1-C2- fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl
- Ci-C4-alkoxy such as methoxy or ethoxy
- C1-C4- haloalkoxy such as difluoromethoxy or trifluoromethoxy.
- radical R 4 is also even more particularly selected from the group consisting of
- Ci-C6-alkyl which is unsubstituted, partially or completely halogenated or substituted by one radical selected from CN, C3-C6 cycloalkyl, Ci-C4-alkoxy and Ci-C4-alkoxycarbonyl,
- C3-C6 cycloalkyl which is unsubstituted, partly or completely halogenated, and C2-C6-alkenyl, which is partly or completely halogenated.
- a particular group (2a) of embodiments relates to compounds of the formula (I), where Y is O and where R 3 is as defined for groups (2) or (2') of embodimens and R 3 is in particular selected from the group consisting of:
- R 7a , R 8 , R 9a , R 9b and R 22 are as defined herein and wherein R 7a , R 8 , R 9a , R 9b and R 22 have in particular the following meanings:
- R 7a is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6- cycloa I kyl , C3-C6-cycloa I kyl methyl ,
- Ci-C6-alkyl which is subsituted by 1 radical selected from phenyl, pyridyl, cyano, C1-C4- alkoxy, Ci-C4-alkoxycarbonyl and C3-C4-cycloalkyl,
- R 8 is selected from the group consisting of Ci-C4-alkyl, C3-C4-cycloalkyl, C3-C4- cycloalkylmethyl, benzyl and pyridylmethyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,
- Ci-C4-alkyl which is substituted by 1 or 2 radicals selected from the group consisting of cyano, Ci-C4-alkoxy, Ci-C4-alkylamino, di-Ci-C4-alkylamino;
- R 9a , R 9b is selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and
- R 9a , R 9b may also be Ci-C4-alkoxy, C3-C4-cycloalkoxy or
- R 22 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated,
- R 8 is selected from the group consisting of Ci-C4-alkyl, C3-C4-cycloalkyl, C3-C4- cycloalkylmethyl, benzyl and pyridylmethyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, Ci-C4-alkyl, which is substituted by 1 or 2 radicals selected from the group consisting of cyano, Ci-C4-alkoxy, Ci-C4-alkylamino, di-Ci-C4-alkylamino;
- R 17a , R 17b are selected from the group consisting of are selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and C3-C4-cycloalkylmethyl.
- R 3 is CN.
- R 3 is NO2.
- R 4 is as as defined above and in particular selected from the group of radicals of groups i) to vi) and viii) to xii) and especially from the radicals of groups ii), iii), iv), viii), ix), and xi), as defined above and where
- R 7a is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl,
- R 8 is as defined above and in particular Ci-C4-alkyl or Ci-C4-haloalkyl,
- R 17a , R 17b are as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted, partly or completely halogenated;
- viii) is in particular C3-C6 cycloalkyl, which is unsubstituted, partially or completely halogenated and/or carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
- ix) is in particular phenyl or benzyl, where the phenyl ring is optionally substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 , where the radical R 10 , irrespective of its occurrence, is in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- halogen such as fluorine, chlorine or bromine
- CN Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- Ci-C4-haloalkyl especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, and Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, Ci-C4-alkylthio, such as methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl, isobutylsulfanyl, or
- xi) is in particular Het # or Chb-Het*
- Het # is as defined above and in particular represents a 5- or 6-membered saturated, partially unsaturated or 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/or 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, C1-C4- alkylcarbonyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy.
- radical R 4 is even more particularly selected from the group consisting of
- Ci-C6-alkyl which is unsubstituted, partially or completely halogenated or substituted by one radical selected from CN, C3-C6 cycloalkyl, Ci-C4-alkoxy and Ci-C4-alkoxycarbonyl; C3-C6 cycloalkyl, which is unsubstituted, partly or completely halogenated;
- Chb-phenyl, Chb-pyridyl or Chb-thienyl where phenyl, pyridyl and thienyl are unsubstituted or carry 1 , 2 or 3 identical or different substituents R 10 , where R 10 is as defined above and in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- halogen such as fluorine, chlorine or bromine
- CN Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.
- Ci-C4-alkylcarbonyl such as acetyl, Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, and Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, Ci-C4-alkylthio, such as methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl, isobutylsulfanyl, or ter
- Ci-C4-alkylcarbonyl such as acetyl
- Ci-C4-haloalkyl especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl
- Ci-C4-alkoxy such as methoxy or ethoxy
- Ci-C4-haloalkoxy such as difluoromethoxy or trifluoromethoxy.
- R w1 is also preferably selected from the group consisting of hydrogen, 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,
- R w1 is selected from the group consisting of hydrogen, CN, methyl or methoxy.
- a first particular group (A) of embodiments relates to compounds of formulae (I) and (l-A), wherein W 2 -W 3 -W 4 is -C(R v2 R w2 )-C(R v3 R w3 )-, wherein the carbon atom which carries R v2 is bound to the nitrogen atom and where R v2 , R w2 , R v3 and R w3 independently of each other, are preferably selected from the group consisting of hydrogen, CN, hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluo- romethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroeth
- R v2 , R v3 and R w2 are hydrogen while R w3 is in particular selected from the group consisting of hydrogen, 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,
- R w3 , R v3 and R w2 are hydrogen while R v2 is in particular selected from the group consisting of hydrogen, 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, di
- R v2 , R v3 , R w2 and R w3 are hydrogen.
- W is in particular S or NR w1 , wherin R w1 is de- fined above.
- W 1 is S.
- R v4 is hydrogen while R v5 is in particular selected from the group consisting 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, such as fluoromethoxy
- R v5 is hydrogen while R v4 is in particular selected from the group consisting 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, such as fluoromethoxy
- R v4 and R v5 are hydrogen.
- R v4 and R v5 may together be a C2-C4 alkylene chain forming a 4- to 6-membered unsaturated ring together with the carbon atoms atom R v4 and R v5 are bonded to, in particular R v4 and R v5 may together be a C3-alkylene chain forming a 5-membered unsaturated ring together with the carbon atoms atom R v4 and R v5 are bonded to.
- W is in particular S or NR w1 , wherin R w1 is defined above. Especially, W is S. In this particular group of embodiments, W is likewise in par- ticular O.
- a second particular group (C) of embodiments relates to compounds of formulae (I) and (l-A), wherein W 2 -W 3 -W 4 is -C(R v2 R w2 )-0-C(R v3 R w3 )-, wherein the carbon atom which carries R v2 is bound to the nitrogen atom and where R v2 , R w2 , R v3 and R w3 independently of each other, are preferably selected from the group consisting of hydrogen, 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- trifluoroethy
- R v2 , R v3 and R w2 are hydrogen while R w3 is in particular selected from the group consisting of hydrogen, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and iso- propyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, tri- fluoromethyl, 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
- R w3 , R v3 and R w2 are hydrogen while R v2 is in particular selected from the group consisting of hydrogen, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and iso- propyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, tri- fluoromethyl, 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
- R v2 , R v3 , R w2 and R w3 are hydrogen.
- W is in particular S or NR w1 , wherin R w1 is defined above.
- W is NR w1 , wherin R w1 is defined above, preferably selected from the group consisting of hydrogen, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-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, such as fluoromethoxy, di
- W.Het-1 represents a radical selected from the group consisting of W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, in where the radical of formula (W.Het) is in particularly even more selected from the radicals W.Het-1 , W.Het-2, W.Het-3, W.Het-4 and W.Het-5, particular selected from the radicals W.Het-1 and W.Het-2.
- R w1 is as defined above and in particular selected from the group consisting of hydrogen, 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- C 4 -alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C 4 -hal
- W.Het is selected from the group consisting of W.Het-3, W.Het-4 and W.Het- 5, wherein R w1 is as defined above and in particular selected from the group consisting of hy- drogen, CN, Ci-C 4 -alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C 4 -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-C 4 -alkoxy, such as methoxy, ethoxy, n- propoxy and isopropoxy, and Ci-C 4 -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-3, Het-1 1 a and Het-24, even more 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-C 4 -alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, C1-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
- 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 and W.Het-5 are both hydrogen.
- each R v4 , R v5 is as defined above and in particular each R v4 , R v5 are independently from each other se- lected from the group consisting of hydrogen, halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, wherein at least one of R v4 , R v5 is different from hydrogen.
- R v4 is hydrogen while R v5 is in particular selected from the group consisting 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, such as fluoro- methoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroeth
- the heterocycle Het is in particular selected from the group con- sisting 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, Het-3 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 isopropyl, C3-C6- cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 , 1 -d if I uoroethyl , 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclo
- 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 -difl 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.
- R 1 and R 2 in the moiety W.Het-2a are both hydrogen.
- 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, Het-3 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 isopropyl, C3-C6- cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difl uoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl
- 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 -difl 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.
- R 1 and R 2 in the moiety W.Het-6 are both hydrogen.
- a particular group (a) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, wherein the moiety of formula (W.Het) 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.
- W.Het represents a radical selected from the group consisting of W.Het-1
- 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, wherein the moiety of formula (W.Het) 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.
- W.Het 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, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-3, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
- W.Het represents a radical selected from the group consisting of W.Het-3, 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, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-4, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
- W.Het represents a radical selected from the group consisting of W.Het-4, 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, wherein the moiety of formula (W.Het) rep- resents 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 (f) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-2a, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a, Het-3 and Het-24.
- W.Het represents a radical selected from the group consisting of W.Het-2a, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a, Het-3 and Het-24.
- a further particular group (g) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, wherein the moiety of formula (W.Het) 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, Het-3 and Het-24.
- W.Het 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, Het-3 and Het-24.
- a special group (aa) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-1 , wherein Het is a radicals of formulae 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, wherein the moiety of formula (W.Het) rep- resents a radical selected from the group consisting of W.Het-2, wherein Het is a radical of formulae 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, wherein the moiety of formula (W.Het) rep- resents a radical selected from the group consisting of W.Het-3, wherein Het is a radical of formulae 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, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-4, wherein Het is a radical of for- mulae 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, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-5, wherein Het is a radical of formulae 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, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-5, wherein Het is a radical of formulae Het-1 1 a.
- a further special group (fa) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-2a, wherein Het is a radical of formulae 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, wherein the moiety of formula (W.Het) rep- resents a radical selected from the group consisting of W.Het-2a, wherein Het is a radical of formulae Het-3.
- a further special group (fa") of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-2a, wherein Het is a radical of formulae Het-1 1 .
- a further special group (ga) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, wherein the moiety of formula (W.Het) represents a radical selected from the group consisting of W.Het-6, wherein Het is a radical of formulae Het-1 a.
- R w1 is as defined above and in particular selected from the group consisting of hydrogen, 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-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, such as fluoromethoxy, difluo- romethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-d
- radicals R 1 and R 2 are, independently from each other, in particular selected from the group consist- ing 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,
- 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 radical
- the variables R 1 , R 2 independently of each other or in particular in combination in particular have the following meanings: 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 C1-C4- alkyl, such as methyl, ethyl, n-propy
- X is in particular O.
- 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 C1-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 fluorome- thyl, 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, or R 1 and R 2 may together be
- X is in particular O.
- 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 C1-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 and where especially both R 1 and R 2 are hydrogen or one of R 1 and R 2 is hydrogen while the other is methyl.
- 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, 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 and where especially both R 1 and R 2 are hydrogen or one of R 1 and R 2 is hydrogen while the other is methyl.
- R w1 irrespectively of its occurrence is selected from the group consisting of hydrogen
- 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
- Ci-C4-haloalkoxy in particular Ci-C2-haloalkoxy, such as fluoro- methoxy, difluoromethoxy, trifluoromethoxy, 1 , 1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy.
- R w1 is
- R v2 , R v3 are independently from each other, are selected from the group consisting of hydrogen CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and iso- propyl, 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 -difluoroethoxy, 2-
- R v2 , R v3 are independently from each other, more particularly hydrogen, or methyl and especially hydrogen.
- R v4 R v5 irrespectively of its occurrence, are independently from each other, are 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, or
- R v4 and R v5 may together be a C2-C4 alkylene chain forming a 4- to 6-membered unsaturated ring together with the carbon atoms atom R v4 and R v5 are bonded to,
- R v4 R v5 irrespectively of its occurrence, are independently from each other, are selected from the group consisting of in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoro- methoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2- trifluoroethoxy, or R v4 and R v5 may together be a C3-alkylene chain forming a 5-membered unsaturated ring together with the carbon atoms atom R v4 and R v5 are bonded to.
- R v4 ⁇ R v5 are independently from each other, more particularly hydrogen, chlorine, fluorine or methyl and espe- cially hydrogen.
- R w2 R w3 irrespectively of its occurrence, are independently from each other, are selected from the group consisting of hydrogen 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 -difluoroethoxy, 2-fluor
- R 5a is selected from the group consisting of hydrogen, CN , Ci-C4-alkyl, C3-C6- cycloalkyl, C3-C6-cycloalkylmethyl, wherein each of the three last mentioned radicals are unsub- stituted, partly or completely halogenated, phenyl and benzyl, 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 , in particular from the group consisting of hydrogen and Ci-C4-alkyl and especially hydrogen.
- 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 trifluormeth- oxy, 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 cyclo
- R 7a irrespectively of its occurrence, is selected from the group consisting of hydrogen, 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-difluoroethyl
- 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-difluoroethyl
- 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 is select- ed from the group consisting of halogen, such as fluorine, chlorine or bromine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, or tert.-butyl, C1-C4- alkylcarbonyl, such as acetyl, Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, and Ci-C4-haloalkoxy, such
- 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-C2-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 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 17 irrespectively of its occurrence, is selected from the group consisting of hydro- gen, 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 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, difluorome- thyl, trifluoromethyl, 1 ,1 -diflu
- 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 radi- cals selected
- 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 17c irrespectively of its occurrence, is selected from the group consisting of hydrogen, 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-difluoroethyl
- R 18 irrespectively of its occurrence, is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated,
- R 19a , R 19b irrespectively of its occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely
- R 19a together with R 19b forms a C4-C6 alkylene chain and form a 5-, 6- or 7- membered saturated, 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, se- lected from oxygen, sulfur or nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen and Ci-C4-alkyl; R 20 irrespectively of its occurrence, is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated.
- R 21 irrespectively of its occurrence, is selected from the group consisting of C1-C6- alkoxy, C3-C6-cycloalkoxy, C3-C6-cycloalkylmethoxy, phenoxy and benzyloxy, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, and where R 21 is more particularly Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci- C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl.
- Ci-C4-alkyl such as methyl, ethyl, propyl, isoprop
- R 22 irrespectively of its occurrence, is selected from the group consisting of hydrogen and Ci-C6-alkyl, it being possible for the last one mentioned group to be unsubstituted, partly or completely halogenated.
- R 23 irrespectively of its occurrence, is selected from the group consisting of hydrogen and Ci-C6-alkyl, it being possible for the last one mentioned group to be unsubstituted, partly or completely halogenated.
- 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 X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 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 X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 b, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2b, to their tautomers, to their stereoisomers and to their salts, whereX, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 c, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2c, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 e, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2d, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 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 X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4a, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3b, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4b, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3c, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4c, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3d, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4d, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3e, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4e, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.5a, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.6a, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.7a, to their tautomers, to their stereoisomers and to their salts, where X, R 3 , Y and R 4 are as defined above and where X, R 3 , Y and R 4 have in particular one of the meanings given in any of lines 1 to 1364 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 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 b, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2b, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 c, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2c, to their tautomers, to their stereoisomers and to their salts where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4a, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3b, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4b, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3c, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4c, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3d, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and whereX, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4d, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3e, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4e, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.5a, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.6a, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.7a, to their tautomers, to their stereoisomers and to their salts, where R 3 is NO2 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2c, to their tautomers, to their stereoisomers and to their salts where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the fol- lowing table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the fol- lowing table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.5a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.6a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.7a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CN and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2c, to their tautomers, to their stereoisomers and to their salts where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.5a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.6a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.7a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CH3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2c, to their tautomers, to their stereoisomers and to their salts where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the fol- lowing table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the fol- lowing table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and whereX, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.5a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.6a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.7a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the fol- lowing table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2c, to their tautomers, to their stereoisomers and to their salts where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.1 d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.2e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 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 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the fol- lowing table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4b, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4c, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4d, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.3e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.4e, to their tautomers, to their stereoisomers and to their salts, where R 3 is CF3 and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.5a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the fol- lowing table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.6a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
- a further special group of embodiments relates to the compounds of formula (l)-A.7a, to their tautomers, to their stereoisomers and to their salts, where R 3 is CI and where X, Y and R 4 have in particular one of the meanings given in any of lines 1 to 613 or 683 to 1295 of the following table A.
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- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
La présente invention concerne des composés N-acylimino de formule (I) : X représentant O ou S, notamment O; Y symbolisant une liaison simple entre N et R4 ou Y représentant O, S, S (=O), S(=O)2, CHR5a ou N-R5; Het représentant un noyau hétérocyclique à 5 ou 6 chaînons lié au carbone ou lié à l'azote, W1 représentant O, S ou NRw1; W2-W3-W4 représentant un radical bivalent sélectionné parmi -C(Rv2Rw2)-C(Rv3Rw3)-, -C(Rv4)=C(Rv5)- and -C(Rv2Rw2)-O-C(Rv3Rw3)-; R1, R2 pouvant représenter un hydrogène, halogène etc.; R3 pouvant représenter un hydrogène, CN, C1-C6-alkyle etc.; R4 pouvant représenter un hydrogène, C1-C6-alkyle, C2-C6-alcényle, C2-C6-alcinyle, C3-C8-cycloalkyle, Q-phényle, Q'-O-phényle, Q'-S-phényle, le noyau phényle étant éventuellement substitué par au moins, p.ex. 1, 2, 3, 4 ou 5 substituants identiques ou différents R10, et les groupements Q-Het#, Q'-O-Het# and Q'-S-Het#, Het# représentant un radical hétérocyclique, et Q et Q' représentant C1-C6-alcandiyle, C2-C6-alcèndiyle, ou C2-C6-alkyndiyle, Q pouvant également représenter une liaison simple; R3 et R4 pouvant ensemble représenter également un radical bivalent, sélectionné dans le groupe constitué par C2-C5-alcandiyle, C2-C5-alcèndiyle, Q"-C1-C4-alcandiyle et Q"-C2-C4-alcèndiyle, Q" représentant O ou S. L'invention concerne également l'utilisation des composés N-acylimino hétérocycliques, de leurs stéréoisomères, de leurs tautomères et de leurs sels pour lutter contre les nuisibles invertébrés. L'invention concerne également des procédés de lutte contre les nuisibles invertébrés comportant l'application de tels composés.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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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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 |
WO2013144223A1 (fr) * | 2012-03-30 | 2013-10-03 | Basf Se | Composés de pyrimidinylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles |
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- 2015-10-20 WO PCT/EP2015/074199 patent/WO2016062680A1/fr active Application Filing
Patent Citations (4)
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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 |
WO2013144223A1 (fr) * | 2012-03-30 | 2013-10-03 | Basf Se | Composés de pyrimidinylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles |
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Publication number | Priority date | Publication date | Assignee | Title |
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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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