WO2016062678A1 - N-acylimino heterocyclic compounds - Google Patents

N-acylimino heterocyclic compounds Download PDF

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WO2016062678A1
WO2016062678A1 PCT/EP2015/074196 EP2015074196W WO2016062678A1 WO 2016062678 A1 WO2016062678 A1 WO 2016062678A1 EP 2015074196 W EP2015074196 W EP 2015074196W WO 2016062678 A1 WO2016062678 A1 WO 2016062678A1
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het
alkyl
radicals
group
alkoxy
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PCT/EP2015/074196
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French (fr)
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Karsten KÖRBER
Martin John MCLAUGHLIN
Birgit GOCKEL
Wolfgang Von Deyn
Kenichi Kojima
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—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
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/88—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
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • 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

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
  • 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 C1-C4- acyl.
  • the moiety electron withdrawing moiety Z is an electron withdrawing group such as alkoxcarbonyl, arylcarbonyl, heterocyclic carbonyl, Ci-C4-alkylsulfonyl, sulfamoyl or C1-C4- 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
  • Chem. 2008, 51 , 4213-4218 describe triflouroacetylimino and pyrazinoylimino heterocyclic compounds of imidazolidine and thiazolidine derivatives, which show 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.
  • PCT/EP2014/069900 relates to saturated, unsaturated, or partially unsaturated 5- or 6- membered nitrogen containing heterocycles having a 2-imino group.
  • the compounds 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 compound of formula (I):
  • n is an integer selected from 0, 1 , 2, 3, 4, 5 and 6;
  • X 1 is O or S;
  • X 2 is CN or N0 2 ; is a 5- or 6-membered carbon-bound or nitrogen-bound heterocyclic or heteroaromatic 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 cydoaliphatic 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, are selected from the group consisting 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 cydoaliphatic radicals may be unsubstituted or may be partly or fully halogenated and/or
  • 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, or
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3-,
  • phenyl benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • R 4a , R 4b are selected each independently from one another and independently from the integer of m from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C1-C6- alkoxy, Ci-C6-alkylthio and Cs-Cs-cycloalkyl, wherein each of the four last mentioned radicals are unsubstituted, partly or completely halogenated,
  • R 4a and R 4b may form together with the carbon atom they are bound to, a 3-, 4-, 5- or 6- membered aliphatic ring, wherein each of the carbon atoms of the ring may be
  • Ci-C4-alkyl unsubstituted or may be partly or fully halogenated, and/or may carry 1 , 2, 3, 4, 5 or 6 radicals selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
  • R 9b is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2 Ce-alkynyl, C 3 -C 8 -cycloalkyl, 0-Ci-C 6 -alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -C 6 -alkynyl, 0-C 3 -C 8 - cycloalkyl, S(0) n -Ci-C 6 -alkyl, S(0)n-C 2 -C 6 -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, 4 or 5 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, O, S, S(O), S(0)2, NR 9a ,
  • 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 aforementioned aliphatic and cyclo-aliphatic radicals may optionally be further substituted independently from one another with 1 , 2 or 3 radicals R 7 ,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the 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 ; 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, C3-Cio-cycloalkyl, C3-C8- hal
  • 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-Cio-alkyl, C3-C10- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Cs-Cs-cycloalkenyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be partly or completely halogenated, and/or be substituted with 1 , 2,3 or 4, in particular 1 , 2 or 3, identical or
  • 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, independently of its occurrence, is selected from the group consisting of Ci-C6-alkyl, C3-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C 4 -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the five last mentioned radicals are unsubstituted, partly or completely halogenated,
  • phenyl benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • 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, C1-C6- alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alky
  • 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, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 halo
  • R 10 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 cydoaliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals R 10a ,
  • 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; or
  • halogen, cyano, halomethyl and halomethoxy independently of its occurrence, is selected from the group consisting of halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl,
  • 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;
  • R 11 , R 12 independently of their occurrence, are selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8-halocycloalkyl-Ci-C4-alkyl, C1-C6- haloalkoxy-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals are unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical
  • 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; 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
  • 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;
  • R 17 independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, trimethylsilyl, triethylsilyl, te/ibutyldimethylsilyl,
  • 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 , R 17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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-C 4 -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-
  • 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-C 4 -haloalkyl, Ci-C 4 -alkoxy or Ci-C 4 -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; the stereoisomers, tautomers and the salts thereof.
  • N-acylimino compound of formula (I) wherein m is an integer selected from 0, 1 , 2, 3, 4, 5 and 6; X 1 is O or S; X 2 is CN or N0 2 ;
  • Het is a 5- or 6-membered carbon-bound or nitrogen-bound heterocyclic or heteroaromatic 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 ;
  • ?w1 is selected from the group consisting hydrogen, cyano, nitro, SCN , Ci-Cio-alkyl, C3- Ce-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, are selected from the group consisting 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
  • 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-C10- alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or may be partly
  • 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
  • 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, or
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3-,
  • phenyl benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • 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 4b are selected each independently from one another and independently from the integer of m from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C1-C6- alkoxy, Ci-C6-alkylthio, and Cs-Cs-cycloalkyl, wherein each of the four last mentioned radicals are unsubstituted, partly or completely halogenated,
  • R 4a and R 4b may form together with the carbon atom they are bound to, a 3-, 4-, 5- or 6- membered aliphatic ring, wherein each of the carbon atoms of the ring may be
  • Ci-C4-alkyl unsubstituted or may be partly or fully halogenated, and/or may carry 1 , 2, 3, 4, 5 or 6 radicals selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
  • R 9b is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C2-C6-alkenyl, C 2 - Ce-alkynyl, C 3 -C 8 -cycloalkyl, 0-Ci-C 6 -alkyl, 0-C 2 -C 6 -alkenyl, 0-C 2 -C 6 -alkynyl, 0-C 3 -C 8 - cycloalkyl, S(0) n -Ci-C 6 -alkyl, S(0)n-C 2 -C 6 -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, O, S, S(O), S(0)2, NR 9a ,
  • 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 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-Cio-alkyl, Cs-Cs- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C3-Cs-cycloalkenyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be partly or completely halogenated, and/or be substituted with 1 , 2,3 or 4, in particular 1 , 2 or 3, identical or
  • 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, independently of its occurrence, is selected from the group consisting of Ci-C6-alkyl, Cs-Cs-cycloalkyI, C3-C8-cycloalkyl-Ci-C 4 -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the five last mentioned radicals are unsubstituted, partly or completely halogenated,
  • phenyl benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 9b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-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 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, Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci- C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6 halo
  • 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,
  • R 10 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 R 10a ,
  • 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; or
  • 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;
  • R 11 , R 12 independently of their occurrence, are selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8-halocycloalkyl-Ci-C4-alkyl, C1-C6- haloalkoxy-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or
  • R 13 , R 14 independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl; R 15 independently of its occurrence, is selected from the group consisting of hydrogen,
  • R 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,
  • 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;
  • R 17 independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, trimethylsilyl, triethylsilyl, te/ibutyldimethylsilyl,
  • 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 , R 17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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-C 4 -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-
  • 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-C 4 -haloalkyl, Ci-C 4 -alkoxy or Ci-C 4 - haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • 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; the stereoisomers, the 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 parasiticidally effective amount of a compound of formula (I) or the stereoisomers and/or salts, in particular veterinary acceptable salts, thereof;
  • 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 use of a compound of formula (I) or the stereoisomers, tautomers and/or veterinary acceptable salt thereof for the preparation of a medicament for treating, controlling, preventing or protecting animals against infestation or infection by parasites.
  • 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.
  • 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 .
  • Another centre of chirality may be the carbon atom which carries R 3 , in particular if R 3 is different from CN and the group [CR 4a R 4b ] m R 5 .
  • 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.
  • Suitable compounds of the formula (I) also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
  • 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
  • the present invention includes both amorphous and crystalline compounds of the formula (I), mixtures of different crystalline states or modifications of the respective
  • 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 (NH 4 + ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C 4 -alkyl, Ci-C 4 -hydroxyalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, hydroxy-Ci- C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, 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 Ci- 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 is also termed haloalkthio
  • partially or fully halogenated alkylsulfinyl is also termed haloalkylsulfinyl
  • partially or fully halogenated alkylsulfonyl is also termed haloalsulfonyl
  • partially or fully halogenated cycloalkylalkylalkyl is also termed halocycloalkylalkyl.
  • C n -C m -alkyl refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g.
  • 1 to 10 carbon atoms C1-C10- alkyl
  • preferably 1 to 6 carbon atoms Ci-C6-alkyl
  • Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 - methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.
  • C n -C m -haloalkyl refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g.
  • Ci-C4-haloalkyl such as chloromethyl, 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,
  • Ci-C4-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloroflu
  • Ci-Cio-haloalkyl in particular comprises C1-C2- fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.
  • fluoromethyl 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 -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).
  • C1-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, 3,3-dimethylbutylthio, 1 -ethylbutylthio,
  • Ci-Cs-Alkylthio includes the meanings given for Ci-C6-alkylthio and also includes, for example, heptylthio, octylthio, 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 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,
  • chlorodifluoromethoxy 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy.
  • Ci-C m -haloalkylthio (also referred to as haloalkylsulfanyl) is a Ci-C m -haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C2-haloalkylthio such as chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, 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- difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio and
  • 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 -haloalkenyl refers to C2-C m -alkenyl as defined above, 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,
  • C2-C m -alkynyl refers to a linear or branched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1 -butynyl, 2-butynyl, and the like.
  • C2-C m -haloalkynyl as used herein, which is also expressed as “C2-C m -alkynyl which is partially or fully halogenated”, refers to C2-C m -alkynyl as defined above, 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.
  • C2-C m -haloalkynyl examples include 1 -fluoro-2- propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl, 1 -fluoro-2-propynyl and 1 ,1 -difluoro-2- propenyl, and the like.
  • C3-C m -cycloalkyl refers to a monocyclic, bicyclic and polycyclic
  • cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
  • C3-C m -halocycloalkyl as used herein, which is also expressed as “cycloalkyl which is partially or fully halogenated”, refers C3-C m -cycloalkyl as mentioned above, in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • C3-C m -halocycloalkyl examples include 1 - fluorocyclopropyl, 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, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, 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.
  • CHF2OCH2 difluoromethoxymethyl
  • trifluoromethoxymethyl 1 -difluoromethoxyethyl
  • 2-difluoromethoxyethyl 2-trifluoromethoxyethyl
  • difluoro-methoxy-methyl CH3OCF2
  • Ci-C m -alkoxycarbonyl is a Ci-C m -alkoxy group, as defined above, attached via a carbonyl group to the remainder of the moleculae.
  • Ci-C2-Alkoxycarbonyl is methoxycarbonyl or ethoxycarbonyl.
  • Ci-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 Ci-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, hexoxycarbonyl, 1 -methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1 ,1 -dimethylbutoxycarbonyl, 1 ,2- dimethylbutoxycarbonyl, 1 ,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3- dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1 -ethylbutoxy, 2-
  • cycloalkenyl refers to monocyclic hydrocarbon radicals with at least one C-C double bond in the ring, which ring is however not aromatic, the hydrocarbon radicals having 3 to 8 (“Cs-Cs-cycloalkenyl) carbon atoms.
  • Examples are cyclopropenyl, such as cycloprop-1 -enyl and cycloprop-2-enyl, cyclobutenyl, such as cyclobut-1 -enyl and cyclobut-2- enyl, cyclopentenyl, such as cyclopent-1 -enyl, cyclopent-2-enyl and cyclopent-3-enyl, cyclopentadienyl, such as cyclopenta-1 ,3-dienyl, cyclpenta-1 ,4-dienyl and cyclpenta-2,4-dienyl, cyclohexenyl, such as cyclohex-1 -enyl, cyclohex-2-enyl and cyclohex-3-enyl, cyclohexadienyl, such as cyclohexa-1 ,3-dienyl, cyclohexa-1 ,4-dienyl, cyclo
  • aryl refers to an aromatic hydrocarbon radical having usually 6 to 14 carbon atoms such as phenyl or naphthyl or in particular phenyl.
  • 3- to 6-membered carbocyclic ring refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings.
  • 3- to 7-membered carbocyclic ring refers to cyclopropane, cyclobutane, cyclopentane, cyclohexane and cycloheptane rings.
  • heteroatom groups also referred to as "3-, 4-, 5-, 6- or 7-membered saturated, partially saturated or (unsaturated) aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms” or “containing heteroatom groups", wherein those heteroatom(s) (group(s)) are selected from N, O, S, NO, SO and SO2 and are ring members, as used herein refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic.
  • the heterocyclic radical may be attached to the remainder of the 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
  • Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3- dihydrothien-2-yl, 2,3 dihydrothien-3-yl, 2,4 dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2- yl, 2-pyrrolin-3-yl, 3 pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4 isoxazolin 3 yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2 isoxazolin-5-yl, 3-isox
  • 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.
  • Cn-Cm-alkylene is divalent branched or preferably non-branched or linear saturated aliphatic chain having n to m, e.g. 2 to 7 carbon atoms, for example CH2CH2, -CH(CH3)-,
  • Embodiments of the present invention as well preferred compounds of the present invention are outlined in the following paragraphs.
  • the remarks made below concerning preferred embodiments of the variables of the compounds of formula (I), especially with respect to their substituents X 1 , X 2 , W 1 , W 2 , W 3 , W 4 , Het, R 1 ,R 2 , R 3 , R 4a , R 4b and R 5 and their variable k and m are valid both on their own and, in particular, in every possible combination with each other.
  • Het is selected from the group consisting of radicals of formulae Het-1 to Het-24, with preference given to compounds of the formula (I), their stereoisomers, there tautomers and their salts, where Het is selected from the radicals of the formulae Het-1 , Het-1 1 and Het-24:
  • Het-21 Het-22 Het-23 Het-24 wherein # denotes the bond to the remainder of the molecule 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 Ci-C4-haloalkyl.
  • k is 0, 1 or 2, especially 0 or 1.
  • Het-1 , Het-2, Het-3, Het-4, Het-7, Het-8, Het-9, Het-10, Het-1 1 , Het-18 and Het-21 k is especially 1.
  • R 6a in formulae Het-12, Het-13, Het-14, Het-16, Het-17, Het-19, Het 20 and Het-22 is different from hydrogen.
  • R 6 is in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, C1-C4- haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as 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-difluoroethy
  • 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 difluoro
  • 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 consistin of radicals of formulae Het-1 , Het-1 1 a and Het-24,
  • Ci-C4-alkyl such as methyl or ethyl
  • Ci-C4-alkoxy such as methoxy or ethoxy
  • Ci-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 Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pent
  • 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,
  • 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 difluo
  • a particular sub-group of embodiments relates to compounds of the formula (I), to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 a
  • R 6 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl or pentafluoroethyl;
  • halogen such as chlorine or fluorine
  • Ci-C4-alkyl such as methyl or ethyl
  • Ci-C4-haloalkyl such as difluoromethyl, trifluoro
  • 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 Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as
  • Het-1 1 a 2-chlorothiazol-5-yl, i.e. R 6a is chlorine.
  • Het is a radical of formula Het-24, where k is 0, 1 or 2, in particular 0 or 1 , and where R 6 , if present, is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci- C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoro
  • R 1 and R 2 are independently from each other selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6- cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl.
  • Ci-C6-alkyl in particular Ci-C4
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl.
  • R 1 and R 2 are independently from each other selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl.
  • At least one of the radicals R 1 and R 2 is hydrogen.
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, C3-C6-halocycloalkyl, such as 1 -fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 1 -fluorocyclobutyl, 2- fluorocyclobutyl, 3-fluorocyclobutyl, 2,2-difluorocyclobutyl or 3,3-difluorocyclobutyl, NR 9a R 9b and NR
  • the radicals R 7a is 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.
  • Ci-C4-alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl
  • Ci-C4-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethy
  • the radicals 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-C4-alkyl and Ci- C4-haloalkyl.
  • 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.
  • radicals NR 9a C(
  • the radical R 3 is especially selected from the group consisting of hydrogen and Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl or n-butyl.
  • Het # is preferably 5- or 6-membered hetaryl such as pyridyl, thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxazolyl or isoxazolyl, which is
  • R 10 is preferably 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-C 2 -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-C 2 -haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluorome
  • the radical R 7a is preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C 3 -C6-cycloalkyl, C 3 -C6-cycloalkyl- Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted 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-C 2 -haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-diflu
  • R 7a is in particular Ci-C4-alkyl.
  • the radical R 8 is preferably 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 unsubstituted 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- fluoroeth
  • the radicals 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
  • 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.
  • the phenyl ring is optionally substituted with 1 , 2, 3, 4, or 5 identical or different substituents R 10 .
  • the radical R 10 is preferably selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C4- alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy,
  • the radical R 5 is in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, Ci-C6-alkyl, in particular C1-C4- alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, S-d-Ce-alkyl, in particular S-Ci-C 4 -alkyl, such as methylthio, ethylthio, n-propylthio and isopropylthio, S-Ci-C
  • variable m is preferably 0, 1 or 2, in particular with regard to the group of
  • R 3 and R 5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated carbocyle, in particular a 3-membered carbocycle, wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , wherein R 7b is as defined above and wherein
  • R 7b is in particular selected from the group consisting of halogen, Ci-C6-alkyl, C1-C6- alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by 1 or 2 radicals R 7 , and wherein one or two radicals R 7b may also be C3-C8-cycloalkyl, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2,
  • C3-C6-cycloalkenyl which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl,
  • R 7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
  • R 7 is as defined above and in particular selected from Ci-C4-alkoxy, C1-C4- alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy, phenyl, phenoxy, 5- or 6- membered saturated heterocyclyl having 1 heteroatom selected from O and S, and 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N as ring memberes, where 5- or 6-membered saturated heterocyclyl and 5- or 6-mbered hetaryl may be unsubstituted or carry 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and C1-C4- haloalkoxy
  • R 10 is as defined above and in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy,
  • R 3 and R 5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated carbocyle, in particular a 3-membered carbocycle, wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , wherein R 7b is as defined above and wherein
  • R 7b is in particular selected from the group consisting of halogen, Ci-C6-alkyl, C1-C6- alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by 1 or 2 radicals R 7 , wherein R 7 is as defined above and has in particular one of the preferred meanings and
  • C3-C8-cycloalkyl in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , or
  • R 7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
  • R 10 is as defined above and in particular selected from the group consisting of halogen,
  • Ci-C4-alkyl Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 3 and R 5 together with the carbon atom, to which they are bound, form a 3- or 4-membered saturated carbocyle, i.e. a 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical, in particular a 1 ,1 -cyclopropylidene radical wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , wherein
  • R 7b is as defined above and in particular selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxycarbonyl, and wherein one radical R 7b may also be C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine, Ci-C4-alkyl such as methyl, or Ci-C4-alkoxycarbonyl, or phenyl, optionally substituted with 1 , 2, 3, 4 or 5, in particular 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 or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
  • halogen such as fluorine or chlorine
  • Ci-C4-alkyl CN
  • Ci-C4-haloalkyl Ci-C4-alkoxy
  • C1-C4- haloalkoxy C1-C4- haloalkoxy
  • R 3 and R 5 together with the carbon atom, to which they are bound, form a 3- or 4-membered saturated carbocyle, i.e. a 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical, in particular a 1 ,1 -cyclopropylidene radical wherein each of the carbon atoms of the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , wherein R 7b is as defined above and in particular selected from the group consisting of halogen, Ci-C4-alkyl, and wherein one radical R 7b may also be
  • R 10 is as defined above, and in particular selected from the group consisting of halogen, such as fluorine or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
  • halogen such as fluorine or chlorine
  • Ci-C4-alkyl CN
  • Ci-C4-haloalkyl Ci-C4-alkoxy
  • C1-C4- haloalkoxy C1-C4- haloalkoxy
  • CHCI-CHCI-CHCI CCI2-CHCI-CH2, CHCI-CCI2-CH2, CCI2-CH2-CCI2, CCI2-CCI2-CH2,
  • R 7bb is selected from the group consisting of
  • Ci-C6-alkyl in particular C2-C6-alkyl, such as ethyl, n-propyl, isopropyl, n-butyl, tert.butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3- dimethylpropyl, 1 -methylbutyl, 1 ,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl, , Ci-C6-haloalkyl, in particular C2-C4-haloalkyl, such as 2,2-difluoroethyl, 1 ,1 - difluoroethyl or 2,2,2-trifluoroethyl,
  • Ci-C6-alkoxy such as methoxy, ethoxy, propoxy
  • Ci-C6-alkyl which is substituted by 1 radical selected from Ci-C4-alkoxy, C1-C4- alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Cs-Cs-cycloalkyl, C3- Cs-cycloalkoxy, phenoxy and 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothiopyranyl, where Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy and 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples of substituted Ci-C6-alkyl including 1 -methoxyethyl, 2-meth
  • C2-C6-alkynyl such as ethynyl
  • Ci-C4-alkyl optionally substituted by 1 or 2 Ci-C4-alkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 4-methylcyclohexyl, 4- isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl,
  • Ci-C4-alkyl such as 2- methylcyclohex-3-en-1 -yl
  • 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6-membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tehtrahydrothiopyran-
  • phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl, 3- (trifluoromethyl)phenyl and 4-cyanophenyl,
  • phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-flu
  • 5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy examples of hetaryl including 4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl, phenyl-Ci-C4-alkyl, such as benzyl or phenethyl, and
  • hetaryl-Ci-C4-alkyl where the hetaryl is 5- or 6-membered and has 1 or 2
  • heteroatoms as ring memberes selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy examples of hetaryl-Ci-C4-alkyl including 1 ,1 -dimethyl-2-(3-pyridyl)ethyl,
  • CHCI-CHCI-CHCI CCI2-CHCI-CH2, CHCI-CCI2-CH2, CCI2-CH2-CCI2, CCI2-CCI2-CH2,
  • Ar is selected from phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl and 4-cyanophenyl,
  • R 7b1 is hydrogen or has one of the meanings given for R 7b ;
  • R 7b2 , R 7b3 and R 7b4 are hydrogen, methyl or halogen, in particular hydrogen.
  • R 7b1 is in particular hydrogen or a radical selected from the group consisting of Ci-C6-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert. butyl, 1 - methylpropyl, 2-methylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3- dimethylpropyl, 1 -methylbutyl, 1 ,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl,
  • Ci-C6-alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert. butyl, 1 - methylpropyl, 2-methylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3- dimethylpropyl, 1 -methylbutyl, 1 ,2-d
  • Ci-C4-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 1 ,1 - difluoroethyl or 2,2,2-trifluoroethyl,
  • Ci-C6-alkyl which is substituted by 1 radical selected from Ci-C4-alkoxy, C1-C4- alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Cs-Cs-cycloalkyl, C3- Cs-cycloalkoxy, phenoxy and 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothiopyranyl, where Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy and 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples of substituted Ci-C6-alkyl including 1 -methoxyethyl, 2-meth
  • C2-C6-alkynyl such as ethynyl
  • C3-Cio-cycloalkyl optionally substituted by halogen and/or Ci-C4-alkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 4- methylcyclohexyl, 4-isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
  • Ci-C4-alkyl such as 2- methylcyclohex-3-en-1 -yl
  • 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6-membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tehtrahydrothiopyran-
  • phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl, 3- (trifluoromethyl)phenyl and 4-cyanophenyl,
  • phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-flu
  • 5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy examples of hetaryl including 4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl, phenyl-Ci-C4-alkyl, such as benzyl or phenethyl, and
  • hetaryl-Ci-C4-alkyl where the hetaryl is 5- or 6-membered and has 1 or 2
  • heteroatoms as ring memberes selected from O, S and N and where the hetaryl is unsubsituted or substituted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, examples of hetaryl-Ci-C4-alkyl including 1 ,1 -dimethyl-2-(3-pyridyl)ethyl.
  • compounds of formula (I) are preferred, wherein R 3 and R 5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6-membered saturated heterocycle having 1 or 2 non adjacent heteroatoms as ring memberes which are selected from O and S, wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , wherein
  • R 7b is as defined above and in particular as defined for embodiment B and especially selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4- alkyl, Ci-C4-alkoxycarbonyl,
  • C3-C6-cycloalkyl which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine, Ci-C4-alkyl such as methyl, or Ci-C4-alkoxycarbonyl, or
  • R 10 is as defined above, and in particular selected from the group consisting of halogen, such as fluorine or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
  • halogen such as fluorine or chlorine
  • Ci-C4-alkyl CN
  • Ci-C4-haloalkyl Ci-C4-alkoxy
  • C1-C4- haloalkoxy C1-C4- haloalkoxy
  • R 3 and R 5 together form O-CH2 or O-CH2CH2, wherein 1 , 2, 3 or 4 of the hydrogen atoms in CH2 or CH2CH2, may be replaced by R 7b , thereby forming, together with the carbon atom they are bound to, an unsubstituted or substituted oxiran-2,2-diyl or oxetan-2,2-diyl.
  • R w1 is 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, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluor
  • R w1 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-alkylcarbonyl.
  • R w1 is hydrogen, methyl or methylcarbonyl (acetyl).
  • a further preferred group of embodiments relates to compounds of formulae (I) and (la), wherein W 2 -W 3 -W 4 is a bivalent radical -C(R v2 R w2 )-C(R v3 R w3 )-, in which the carbon atom which carries R v2 and R w2 is attached to W 1 .
  • R v2 , R w2 , R v3 and R w3 are independently from each other preferably selected from 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 C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
  • R v2 , R w2 , R v3 and R w3 are, independently of each other, selected from hydrogen and Ci-C2-alkyl.
  • R v2 , R w2 , R v3 and R w3 are, independently of each other, hydrogen or methyl.
  • R v2 , R w2 , R v3 and R w3 is in particular 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 C1-C2- haloalkoxy, such as fluoromethoxy,
  • R v2 , R v3 , R w2 and R w3 are each hydrogen.
  • W is preferably S or NR w1 , wherein R w1 is as defined above and has in particular one of the preferred meanings, especially hydrogen or Ci-C2-alkyl such as methyl.
  • R v4 and R v5 are both hydrogen.
  • W is in particular S or NR w1 , wherein R w1 has one of the meanings given above, especially a preferred meaning, in particular hydrogen or methyl, especially hydrogen.
  • W is in particular N-CH3.
  • W is in particular O.
  • R v4 and R v5 are both different from hydrogen.
  • 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, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroe
  • R v4 and R v5 are both selected from Ci-C4-alkyl.
  • W is O, S or NR w1 , wherein R w1 has one of the meanings given above, especially a preferred meaning.
  • W is S.
  • W 1 is O, S or NR w1 , wherein R w1 has one of the meanings given above, especially a preferred meaning.
  • W is S.
  • a further particular group of embodiments relates to compounds of formulae (I) and (la), wherein W 2 -W 3 -W 4 is C(R v2 R w2 )-0-C(R v3 R w3 )-, wherein C(R v2 R w2 )- is bound to W 1 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, CN, Ci-C4-alkyl, in particular Ci-C2-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-alkyl, such as Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2- diflu
  • R w2 , R v3 and R w3 are different from hydrogen.
  • R v2 , R v3 , R w2 and R w3 are all hydrogen.
  • W is preferably NR w1 , where R w1 is as defined above and, preferably has one of the preferred meanings.
  • R w1 is hydrogen or Ci-C4-alkyl, more preferably hydrogen or methyl.
  • 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, and W.Het-5 and W.Het-6
  • R w1 if present, is as defined above and in particular 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 me
  • R w1 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-alkylcarbonyl. Especially, R w1 is hydrogen, methyl or methylcarbonyl (acetyl), in particular hydrogen or methyl.
  • R v 4 and R v5 are different from hydrogen and R v4 and R v5 have the meanings given above, preferably the meanings given as preferred and in particular are independently from each other selected from the group consisting of hydrogen, halogen such as chlorine, Ci-C4-alkyl such as methyl, ethyl, n-propyl and isopropyl, and Ci-C4-haloalkyl in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,
  • compounds of formulae (I) and (la) wherein the moiety of the formula (W.Het) is a radical W.Het-2a, wherein R v4 and R v5 are as defined and in particular are independently from each other selected from the group consisting of hydrogen, halogen such as chlorine, Ci-C4-alkyl such as methyl, ethyl, n-propyl and isopropyl, and 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, wherein at
  • the heterocycle Het is in particular selected from the group consisting of the radicals of formulae Het-1 to Het-24, as defined above, and in particular selected from the group consisting of the radicals of the formulae Het-1 or Het-1 a, Het-1 1 a and Het-24.
  • the radicals R 1 and R 2 are, independently from each other, in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci- C4-alkyl, such as methyl, ethyl, n-propyl or 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 C
  • 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-2a, W.Het-2, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, are both hydrogen.
  • a particular group 1 of embodiments relates to compounds of the formulae (I) and (la), 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 2 of embodiments relates to compounds of the formulae (I) and (la), 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 3 of embodiments relates to compounds of the formulae (I) and (la), 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 4 of embodiments relates to compounds of the formulae (I) and
  • a further particular group 5 of embodiments relates to compounds of the formulae (I) and (la), 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 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-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 6 of embodiments relates to compounds of the formulae (I) and (la), 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 and Het-24.
  • W.Het represents a radical selected from the group consisting of W.Het-2a
  • Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
  • a further particular group 7 of embodiments relates to compounds of the formulae (I) and (la), 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 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 and Het-24.
  • a special group 1 a of embodiments relates to compounds of the formulae (I) and (la), 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 2a of embodiments relates to compounds of the formulae (I) and (la), 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 a radicals of formulae Het-1 a.
  • a further special group 3a of embodiments relates to compounds of the formulae (I) and (la), 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 a radicals of formulae Het-1 a.
  • a further special group 4a of embodiments relates to compounds of the formulae (I) and (la), 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 radicals of formulae Het-1 a.
  • a further special group 5a of embodiments relates to compounds of the formulae (I) and (la), 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 radicals of formulae Het-1 a.
  • a further special group 6a of embodiments relates to compounds of the formulae (I) and
  • a further special group 7a of embodiments relates to compounds of the formulae (I) and (la), 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 radicals of formulae Het-1 a.
  • the radical R w1 is as defined above and in particular 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, 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-fluoroe
  • n 0 or 1 ;
  • R 1 and R 2 are, independently from each other, selected from the group consisting of
  • R 3 is selected from the group consisting of hydrogen, halogen, CN , Ci-C6-alkyl, in
  • R 7a , R 9a , R 9b and R 10 are as defined above and in particular have the preferred meanings;
  • n 0 or 1 ;
  • R 1 and R 2 are, independently from each other, selected from the group consisting of hydrogen, halogen, cyano, Ci-C 3 -alkyl, such as methyl ethyl or isopropyl, or Ci-C 3 - 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;
  • R 5 is selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, S-d-Ce-alkyl, in particular S-Ci-C 4 -alkyl, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, 2-butylthio or iso
  • the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a
  • the variables R 1 , R 2 , R 3 , and R 5 independently of each other or in particular in combination, especially may also have the following meanings:
  • n 0 or 1 ;
  • R 1 and R 2 are hydrogen; R 3 is selected from the group consisting of hydrogen, fluorine, chlorine, Ci-C4-alkyl,
  • R 5 is hydrogen, halogen, d-Ce-alkyl, d-Ce-haloalkyl, S-d-Ce-alkyl, S-d-Ce-haloalkyl, d-d- cycloalkyl, d-d-halocycloalkyl, S-d-d-cycloalkyl, S-d-d-halocycloalkyl, phenyl and and S-phenyl, where the phenyl ring in the last to radicals is unsubstituted or carries 1 , 2,
  • R 4a , R 4b are each hydrogen, or
  • R 3 and R 5 together with the carbon atom, to which they are bound, form a 3- or 4-membered saturated carbocycle, wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3,
  • R 3 and R 5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated heterocycle having 1 or 2 non adjacent heteroatoms as ring members which are selected from O and S, wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , where
  • R 7b is selected from the group consisting of halogen, d-d-alkyl, and wherein one
  • radical R 7b may also be
  • R 10 is selected from the group consisting of halogen, CN, d-d-alkyl, Ci-C 4 - haloalkyl, d-d-alkoxy and d-d-haloalkoxy.
  • R 7b is in particular selected from the group consisting of
  • halogen Ci-C6-alkyl, Ci-C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by a radical selected from Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, phenoxy, 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected
  • Cs-Cs-cycloalkyI in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from halogen, Ci-C4-alkyl and Ci-C4-alkoxycarbonyl , in particular selected from fluorine, chlorine, and methyl,
  • C3-C6-cycloalkenyl which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl,
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , or
  • R 7b together form a linear C2-C7-alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
  • R 10 has one of the meanings given above and where R 10 is in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy,
  • R 7b is more particularly selected from the group consisting of halogen, Ci-C6-alkyl, Ci-
  • C3-C6-cycloalkyl which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , or a
  • R 7b together form a linear C2-C7-alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
  • R 10 has one of the meanings given above and is in particular selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
  • 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;
  • R 3 and R 5 together with the carbon atom, to which they are bound, form a 3- or 4-membered saturated carbocycle, i.e. a 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical, wherein each of the carbon atoms of the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , wherein
  • R 7b is as defined above and in particular selected from the group consisting of
  • halogen Ci-C6-alkyl, Ci-C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by a radical selected from Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, phenoxy, 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected
  • C3-C8-cycloalkyl in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from halogen, Ci-C4-alkyl and Ci-C4-alkoxycarbonyl, in particular selected from fluorine, chlorine and, methyl as,
  • C3-C6-cycloalkenyl which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl,
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , or
  • R 7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
  • R 10 has one of the meanings give above and where R 10 is in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or
  • R 7b is especially selected from the group consisting of particular selected from the group consisting of halogen, Ci-C4-alkyl, and wherein one radical R 7b may also be phenyl, optionally substituted with 1 , 2, 3, 4 or 5, in particular 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 or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
  • halogen such as fluorine or chlorine
  • Ci-C4-alkyl CN
  • Ci-C4-haloalkyl Ci-C4-alkoxy
  • C1-C4- haloalkoxy C1-C4- haloalkoxy
  • R 1 and R 2 are hydrogen or one of R 1 and R 2 is hydrogen and the other of R 1 and R 2 is
  • R 3 and R 5 together form the following moieties:
  • R 7bb is selected from the group consisting of
  • C2-C6-alkyl such as ethyl, n-propyl, isopropyl, n-butyl, tert.butyl, 1 -methylpropyl, 2- methylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3-dimethylpropyl, 1 - methylbutyl, 1 ,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl, ,
  • C2-C4-haloalkyl such as 2,2-difluoroethyl, 1 , 1 -difluoroethyl or 2,2,2-trifluoroethyl, Ci-C6-alkyl, which is substituted by 1 radical selected from Ci-C4-alkoxy, C1-C4- alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Cs-Cs-cycloalkyl, C3- Cs-cycloalkoxy, phenoxy and 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothiopyranyl, where Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy and 5- or 6- membered saturated heterocyclyl may be unsubstituted or
  • C3-Cio-cycloalkyl optionally substituted by 1 or 2 Ci-C4-alkyl, in particular C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 4-methylcyclohexyl, 4-isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl, C5-C6-cycloalkenyl, optionally substituted by 1 or 2 Ci-C4-alkyl, such as 2- methylcyclohex-3-en-1 -yl,
  • 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6-membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tehtrahydrothiopyran-
  • phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl, 3- (trifluoromethyl)phenyl and 4-cyanophenyl,
  • phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-flu
  • 5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy examples of hetaryl including 4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl, phenyl-Ci-C4-alkyl, such as benzyl or phenethyl, and
  • hetaryl-Ci-C4-alkyl where the hetaryl is 5- or 6-membered and has 1 or 2
  • heteroatoms as ring memberes selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy examples of hetaryl-Ci-C4-alkyl including 1 ,1 -dimethyl-2-(3-pyridyl)ethyl,
  • R 1 and R 2 are hydrogen or one of R 1 and R 2 is hydrogen and the other of R 1 and R 2 is methyl;
  • R 3 and R 5 together form a moiety selected from the group consisting of:
  • CHF-CHF-CHF CHF-CHF-CHF, CF 2 -CHF-CH 2 , CHF-CF 2 -CH 2 , CF 2 -CH 2 -CF 2 , CF 2 -CF 2 -CH 2 , CF 2 -CF 2 -CF 2 , CHCI-CH2-CH2, CH2-CHCI-CH2, CCI2-CH2-CH2, CH2-CCI2-CH2, CHCI-CHCI-CH2,
  • 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;
  • R 7b1 is hydrogen or has one of the meanings given for R 7b ;
  • R 7b2 , R 7b3 and R 7b4 are hydrogen, methyl or halogen, in particular hydrogen and where
  • R 7b1 is in particular hydrogen or a radical selected from the group consisting of
  • Ci-C6-alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert. butyl, 1 - methylpropyl, 2-methylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3- dimethylpropyl, 1 -methylbutyl, 1 ,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 1 ,1 - difluoroethyl or 2,2,2-trifluoroethyl,
  • Ci-C6-alkyl which is substituted by 1 radical selected from Ci-C4-alkoxy, C1-C4- alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Cs-Cs-cycloalkyl, C3- Cs-cycloalkoxy, phenoxy and 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothiopyranyl, where Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy and 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples of substituted Ci-C6-alkyl including 1 -methoxyethyl, 2-meth
  • Ci-C4-alkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 4-methylcyclohexyl, 4- isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
  • Ci-C4-alkyl such as 2- methylcyclohex-3-en-1 -yl
  • 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6-membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tehtrahydrothiopyran- 3-yl, tetrahydrothiopyran-4-yl, 6-methoxy-3-methyltetrahydropyran-2-yl, and 5,5- dimethyltetrahydrofuran-2-yl,
  • phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl, 3- (trifluoromethyl)phenyl and 4-cyanophenyl,
  • phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-flu
  • 5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy examples of hetaryl including 4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl, phenyl-Ci-C4-alkyl, such as benzyl or phenethyl, and
  • hetaryl-Ci-C4-alkyl where the hetaryl is 5- or 6-membered and has 1 or 2
  • heteroatoms as ring memberes selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy examples of hetaryl-Ci-C4-alkyl including 1 ,1 -dimethyl-2-(3-pyridyl)ethyl.
  • R 7b if present, is in particular selected from the group consisting of
  • halogen Ci-C6-alkyl, Ci-C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by a radical selected from Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, phenoxy, 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected
  • Cs-Cs-cycloalkyI in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine, Ci-C4-alkyl such as methyl and Ci- C4-alkoxycarbonyl such as methoxycarbonyl,
  • C3-C6-cycloalkenyl which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl,
  • R 10 has one of the meanings give for R 10 and where R 10b is in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy,
  • halogen is more particularly selected from the group consisting of halogen, Ci-C6-alkyl, Ci- C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated, and wherein one or two radicals R 7b may also be
  • C3-C6-cycloalkyl which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , or a
  • R 7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where R 10 has one of the meanings given above and where R 10 is in particular selected from the group consisting of halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • 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;
  • R 3 and R 5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated heterocycle having 1 or 2 non adjacent heteroatoms as ring members which are selected from O and S, in particular a 3- or 4-membered saturated heterocycle having 1 oxygen atom as ring member wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R 7b , wherein R 7b , if present, is as defined above and wherein
  • R 7b is as defined above and in particular selected from the group consisting of
  • halogen Ci-C6-alkyl, Ci-C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by a radical selected from Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, phenoxy, 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected
  • C3-Ce-cycloalkyl in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine, Ci-C4-alkyl such as methyl and Ci- C4-alkoxycarbonyl such as methoxycarbonyl, in particular selected from fluorine, chlorine and methyl,
  • C3-C6-cycloalkenyl which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , or
  • R 7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
  • R 10 has one of the meanings give for R 10 and where R 10b is in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or
  • R 7b is especially selected from the group consisting of particular selected from the group consisting of halogen, Ci-C4-alkyl, and wherein one radical R 7b may also be phenyl, optionally substituted with 1 , 2, 3, 4 or 5, in particular 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 or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
  • halogen such as fluorine or chlorine
  • Ci-C4-alkyl CN
  • Ci-C4-haloalkyl Ci-C4-alkoxy
  • C1-C4- haloalkoxy C1-C4- haloalkoxy
  • R 1 and R 2 are hydrogen or one of R 1 and R 2 is hydrogen and the other of R 1 and R 2 is methyl; R 3 and R 5 together form 0-CH 2 or O-CH2-CH2, where 1 , 2, 3 or 4 of the hydrogen atoms of CH 2 and CH2-CH2, respectively, may be replaced by a radical R 7b , thereby forming, together with the carbon atom they are bound to, an unsubstituted or substituted 1 ,1 -cyclopropylidene or 1 ,1 - cyclobutylidene radical.
  • Het # irrespectively of its occurrence, is 5- or 6-membered hetaryl such as pyridyl, thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxazolyl or isoxazolyl, which is unsubstituted or substituted by 1 , 2 or 3 radicals R 10 .
  • Q is, irrespectively of its occurrence, selected from a single bond, S, NR 9a , CH2, and NR 9a CH 2 , and it is in particular a single bond, S, NH, N(Ci-C 4 -alkyl), CH 2 , NHCH 2 or N(Ci- C 4 -alkyl)CH 2 .
  • R 6 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C 4 -alkyl, such as methyl or ethyl, Ci-C 4 -alkoxy, such as methoxy or ethoxy, Ci-C 4 -haloalkoxy, such as difluoromethoxy or trifluormethoxy, and Ci-C 4 -haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C 4 -alkyl and Ci-C 4 -haloalkyl, even more preferably from fluorine, chlorine, Ci-C 2 -alkyl, such as methyl or ethyl and Ci-C 2 -haloalkyl such as
  • difluoromethyl trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
  • R 7 irrespectively of its occurrence, is selected from the group consisting of CN, C1-C4- alkoxy, such as methoxy or ethoxy, Ci-C 4 -haloalkoxy, such as difluoromethoxy or
  • trifluormethoxy such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C 4 -alkyl and Ci-C 4 -haloalkyl, even more preferably from fluorine, chlorine, Ci-C 2 -alkyl, such as methyl or ethyl and Ci-C 2 -haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C3- C6-cycloalkyl such as cyclopropyl, cyclobutyl or cyclopropyl, and C3-C6-halocycloalkyl.
  • R 7a irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C 4 -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, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoro
  • 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 Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,
  • R 8a 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 Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or
  • R 9a and R 9b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR 9a R 9b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C
  • radicals NR 9a R 9b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n- butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n- butylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N- methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N- isobutylamino, 1 -pyrrolidinyl, 1 -piperidinyl, 1 -piperazinly, 4-methyl-1 -piperazinly and 4- morpholinyl.
  • R 10 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci- C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluor
  • R 10a irrespectively of its occurrence, is selected from the group consisting of halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, 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, C1-C6- alkoxy and Ci-C6-haloalkoxy.
  • R 11 , R 12 independently of their occurrence, are selected from the group consisting of Ci- C6-alkyl, Ci-C6-alkoxy, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or substituted with 1 , 2, or 3 identical or different radicals selected from fluorine, chlorine, Ci-C3-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy and Ci-C 2 -haloalkoxy.
  • R 13 , R 14 independently of their occurrence, are selected from the group consisting of hydrogen, fluorine, chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl or n-butyl, C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, and phenyl.
  • R 15 irrespectively of its occurrence, is selected from the group consisting of 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, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl
  • 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 Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or
  • R 17 irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyl, C3-C6- cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is 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,
  • R 17a and R 17b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR 9a R 9b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C
  • radicals NR 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, 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 Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethy
  • Examples of preferred embodiments of the invention are compounds of the formulae 1.1 to
  • Tables 49 to 52 Compounds of the formula 1.7, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X 2 is cyano, and m, R 3 , R 4a , R 4b and R 5 for a compound corresponds in each case to one row of table A.
  • Tables 85 to 88 Compounds of the formula 1.1 1 , their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X 2 is nitro, and m, R 3 , R 4a , R 4b and R 5 for a compound corresponds in each case to one row of table A.
  • Tables 121 to 124 Compounds of the formula 1.16, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X 2 is cyano, and m, R 3 , R 4a , R 4b and R 5 for a compound corresponds in each case to one row of table A.
  • Tables 157 to 160 Compounds of the formula 1.20, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X 2 is nitro, and m, R 3 , R 4a , R 4b and R 5 for a compound corresponds in each case to one row of table A.
  • Tables 193 to 196 Compounds of the formula 1.25, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X 2 is cyano, and m, R 3 , R 4a , R 4b and R 5 for a compound corresponds in each case to one row of table A.
  • Tables 229 to 232 Compounds of the formula 1.29, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X 2 is nitro, and m, R 3 , R 4a , R 4b and R 5 for a compound corresponds in each case to one row of table A.
  • Tables 265 to 268 Compounds of the formula 1.34, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X 2 is cyano, and m, R 3 , R 4a , R 4b and R 5 for a compound corresponds in each case to one row of table A.
  • Tables 301 to 304 Compounds of the formula 1.38, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X 2 is nitro, and m, R 3 , R 4a , R 4b and R 5 for a compound corresponds in each case to one row of table A.
  • R 3 , [CR 4a R 4b ]m and R 5 have the meanings given in one of the rows of the following table A may have S- or R-configuration with regard to the carbon atom carrying the radical R 3 in case that m is zero, R 3 is different from R 5 and different from X 2 and in case that m is 0, R 3 is different from X 2 .
  • the aforementioned embodiments include both the S-enantiomers and the R-enantiomers as well as mixtures of these enantiomers, in particular racemic mixtures.
  • the particularly preferred compounds amongst the compounds of formulae 1.1 to 1.38 mentioned above are those of the formulae 1.1 , 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.13, 1.14, 1.15 and 1.16, in particular 1.1 , I.3, 1.5, 1.7 and 1.15.
  • Particularly preferred compounds are compiled in the following tables B, C, D, E, F, G, H, J, K, L, M and N.
  • the compounds I are selected from the compounds specified in tables B, C, D, E, F, G, H, J, K, L, M, N and in the examples, either as a free base or a tautomer, or a stereoisomer, or a salt thereof.
  • the particularly preferred compounds amongst the compounds of formulae 1.1 to 1.38 mentioned above are also those of the formulae 1.17, 1.18, 1.19, I.20, I.27, I.28 I.35, I.36, 1.37 and 1.38, in particular 1.17, 1.19, I.27, 1.35 and 1.37.

Abstract

The present invention relates to N-acylimino compound of formula (I): (I) wherein X1 is O or S, in particular O; X2 is CN or NO2; m is an integer selected from 0, 1, 2, 3, 4, 5 and 6; Het is a 5- or 6- membered carbon-bound or nitrogen-bound heterocyclic or heteroaromatic ring, W1 is O, S or NRw1; W2-W3-W4 isa bivalent radical selected from -C(Rv2Rw2)-C(Rv3Rw3)-, -C(Rv4)=C(Rv5)- and - C(Rv2Rw2)-O-C(Rv3Rw3)-; R1, R2 may be hydrogen, halogen, etc. R3 may be hydrogen, halogen, CN, C1-C6-alkyl, etc. R4a, R4b if present, may be hydrogen, halogen, C1-C6-alkyl, etc. R5 may be hydrogen, halogen, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C3-C8- cycloalkyl, S(O)nNR9aR9b, NR9aR9b, C(=O)OR8, C(=O)NR9aR9b, C(=S)NR9aR9b, C(=O)R7a, C(=S)R7a, NR9a-C(=O)R7a, NR9a-C(=S)R7a, NR9a-S(O)nR8a, a moitey Q-phenyl, where the phenyl ring is optionally substituted with one or more, e.g. 1, 2, 3, 4 or 5 identical or different substituents R10, or a moiety Q-Het#, or R3 and R5 together may also form with the carbon atom they are bound to, a 3-, 4-, 5- or 6- membered saturated partially unsaturated carbocycle or heterocycle, wherein Rw1, Rw2, Rw3, Rv2, Rv3, Rv5, R7a, R8, R8a, R9a, R9b, Q, Het# are as defomed in the claims. The invention also relates to the use of the N-acylimino heterocyclic compounds, their stereoisomers, their tautomers and their salts, for combating invertebrate pests. Furthermore the invention relates also to methods of combating invertebrate pests, which comprises applying such compounds.

Description

N-acylimino heterocyclic compounds
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. Furthermore the invention relates also to methods of combating invertebrate pests, which comprises applying such compounds. Background of Invention
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:
Figure imgf000002_0001
(A)
where W is a substituted pyridyl radical or a 5-or 6-membered heterocyclic radical, R is hydrogen or alkyl, T together with the atoms to which it is bound forms a 5- or 6-membered heterocyclic ring, Y is inter alia a nitrogen atom and 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 C1-C4- acyl.
US 2013/0150414 describe, inter alia, pesticidal compounds of the formula B
Figure imgf000003_0001
wherein Ar is an aryl or 5- or 6-membered heterocyclic group, Ra is hydrogen or alkyi, Y' is hydrogen, halogen, a hydroxyl group, an alkyi group or an alkoxy group and Rb is an alkyi group substituted with halogen or an alkoxy group, optionally substituted with halogen.
Pesticidal compounds, which are similar to those of US 2013/0150414, are known from
WO 2013/129688.
Ohno et. al, J. Agric. Food chem. 2010, 58, 4999-5003 and Tomizawa et.al, J. Med.
Chem. 2008, 51 , 4213-4218 describe triflouroacetylimino and pyrazinoylimino heterocyclic compounds of imidazolidine and thiazolidine derivatives, which show insecticide activity.
Li et al, J. Mol. Model, 2012, 18(6), 2279-2289 describes three-dimensional quantitative structure-activity relationship of Imidacloprid derivatives (I Ml).
WO2013/129692 describes pesticidal nitrogen-containing heterocyclic derivatives having a 2-imino group represented by formula C,
Figure imgf000003_0002
wherein 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.
PCT/EP2014/069900 relates to saturated, unsaturated, or partially unsaturated 5- or 6- membered nitrogen containing heterocycles having a 2-imino group. The compounds 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. Summary of Invention
It has been found that these objects are solved by 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 compound of formula (I):
Figure imgf000004_0001
wherein m is an integer selected from 0, 1 , 2, 3, 4, 5 and 6;
X1 is O or S; X2 is CN or N02; is a 5- or 6-membered carbon-bound or nitrogen-bound heterocyclic or heteroaromatic 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 R6, wherein k is an integer selected from 0, 1 , 2, 3 and 4;
W1 represents O, S or NRw1;
W2-W3-W4 represents a bivalent radical selected from -C(Rv2Rw2)-C(Rv3Rw3)-, -C(Rv4)=C(Rv5)- and -C(Rv2Rw2)-0-C(Rv3Rw3)-; Rw1 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 cydoaliphatic 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 R7,
OR8, NR9aR9b, S(0)nR8, S(0)nNR9aR9b, C(=0)R7a, C(=0)NR9aR9b, C(=0)OR8, C(=S)R7a, C(=S)NR9aR9b, C(=S)OR8, C(=S)SR8, C(=NR 7)R7a and C(=NR 7)NR9aR9 ; each Rv2, Rv3 independently from each other, are selected from the group consisting 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 cydoaliphatic radicals may be unsubstituted or may be partly or fully halogenated and/or may optionally be further substituted with 1 , 2 or 3 identical or different radicals R7; each Rv4, Rv5 are independently from each other selected from the group consisting hydrogen, halogen, cyano, azido, nitro, SCN, SF5, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2- Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cydoaliphatic 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 R7,
OR8, NR9aR9 , S(0)nR8, S(0)nNR9aR9 , C(=0)R7a, C(=0)NR9aR9 , C(=0)OR8, C(=S)R7a, C(=S)NR9aR9 , C(=S)OR8, C(=S)SR8, C(=NR 7)R7a, C(=NR 7)NR9aR9 and Si(R11)2R12,
or
Rv4 and Rv5 may together be a C2-C5 alkylene chain forming a 4- to 7-membered unsaturated ring together with the carbon atoms atom Rv4 and Rv5 are bonded to and wherein the alkylene chain is unsubstituted or may carry any combination of 1 , 2, 3 or 4 identical or different radicals R7; each Rw2, Rw3 are independently from each other selected from the group consisting hydrogen, cyano, nitro, SCN, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-C10- alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cydoaliphatic 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 R7, C(=0)R7a, C(=0)NR9aR9 , C(=0)OR8, C(=S)R7a, C(=S)NR9aR9 , C(=S)OR8,
C(=S)SR8, C(=NR 7)R7a and C(=NR 7)NR9aR9 , R2 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 and/or may carry any combination of 1 , 2 or 3 radicals R7,
Si(R11)2R12, OR8, OSO2R8, S(0)nR8, S(0)nNR9aR9b, NR9aR9b, C(=0)NR9aR9b,
C(=S)NR aR , C(=0)OR8, C(=0)R7a, C(=S)R7a,
phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
R1 and R2 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 R7,
or
R and R2 may together be =0, =CR13R14, =S, =NR17, =NOR16 or =NNR9aR9 ; is selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated or carries 1 or 2 radicals R7, it being also possible for cycloalkyl to carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
S(0)nNR9aR9 , NR9aR9 , C(=0)OR8, C(=0)NR9aR9 , C(=S)NR9aR9 , C(=0)R7a, C(=S)R7a, NR9a-C(=0)R7a, NR9a-C(=S)R7a, NR9a-S(0)nR8a,
phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; R4a, R4b are selected each independently from one another and independently from the integer of m from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C1-C6- alkoxy, Ci-C6-alkylthio and Cs-Cs-cycloalkyl, wherein each of the four last mentioned radicals are unsubstituted, partly or completely halogenated,
or
R4a and R4b may form together with the carbon atom they are bound to, a 3-, 4-, 5- or 6- membered aliphatic ring, wherein each of the carbon atoms of the ring may be
unsubstituted or may be partly or fully halogenated, and/or may carry 1 , 2, 3, 4, 5 or 6 radicals selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
R4a and R4b may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b, is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2 Ce-alkynyl, C3-C8-cycloalkyl, 0-Ci-C6-alkyl, 0-C2-C6-alkenyl, 0-C2-C6-alkynyl, 0-C3-C8- cycloalkyl, S(0)n-Ci-C6-alkyl, S(0)n-C2-C6-alkenyl,
S(0)n-C2-C6-alkynyl, S(0)n-C3-C8-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl parts of each of the 12 last mentioned radicals are unsubstituted, partly or completely halogenated or carries 1 or 2 radicals R7, it being also possible for cycloalkyl radicals to carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
S(0)nNR9aR9 , NR9aR9 , C(=0)OR8, C(=0)NR9aR9 , C(=S)NR9aR9 , C(=0)R7a, C(=S)R7a, 0-C(=0)OR8, 0-C(=0)NR9aR9 , 0-C(=S)NR9aR9 , 0-C(=0)R7a, 0-C(=S)R7a, NR9a- C(=0)R7a, NR9a-C(=S)R7a, NR9a-S(0)nR8a, a moiety Q-phenyl, where the phenyl ring is optionally substituted with one or more, e.g. 1 ,
2, 3, 4 or 5 identical or different substituents R10,
and a moiety Q-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, 4 or 5 identical or different substituents R10, 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, O, S, S(O), S(0)2, NR9a,
-0-S(=0)2-, -NR a-S(=0)2-, -0-C(=0)-, -NR a-C(=0)-, -0-Ci-C4-alkylene, -S-Ci-C4-alkylene, -S(0)-Ci-C4-alkylene, S(0)2-Ci-C4-alkylene, -NR9a-Ci-C4- alkylene, -0-C(=0)-Ci-C4-alkylene or
Figure imgf000008_0001
where the heteroatom in the last 7 moieties is bound to the carbon atom of C(X2)R3 or CR4aR4a, respectively; or, if m = 0, R3 and R5 together may also form with the carbon atom they are bound to, a 3-, 4-, 5- or 6- membered saturated partially unsaturated carbocyde or heterocycle, wherein the carbocyde or heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, and where the heterocycle 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-R17c, or
R3 and R5 may together form =0 or =S; where, independently of their occurrence, n is 0, 1 or 2;
R6 is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, Ci- Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be further substituted independently from one another with 1 , 2 or 3 radicals R7,
OR8, NR17aR17b, S(0)nR8, S(0)nNR 7aR 7b, C(=0)R7a, C(=0)NR 7aR 7b, C(=0)OR8, C(=S)R7a, C(=S)NR 7aR 7 , C(=S)OR8, C(=S)SR8, C(=NR 7)R7a, C(=NR 7)NR 7aR 7 , Si(R11)2R12;
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R6 present on one ring carbon may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9 , or two R6 together form a linear C2-C7 alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and NR17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=NR17; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6-haloalkynyl, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 radicals R10; independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF5, d-C6-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, Cs-Cs- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Si(R11)2R12, OR8, OSO2R8, S(0)nR8, S(0)nNR 7aR 7b, NR17aR17b, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, C(=0)OR8, C(=0)R15, C(=S)R15, C(=NR 7)R15,
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 R10, 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two R7 present on one carbon atom may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b,
or two R7 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 R7 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 R10; 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, C3-Cio-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, 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 R10, 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-Cio-alkyl, C3-C10- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Cs-Cs-cycloalkenyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be partly or completely halogenated, and/or be substituted with 1 , 2,3 or 4, in particular 1 , 2 or 3, identical or different radicals R7,
OR8, NR17aR17b, S(0)nR8, S(0)nNR 7aR 7b, C(=0)R7a, C(=0)NR 7aR 7b, C(=0)OR8, C(=S)R7a, C(=S)NR 7aR 7b, C(=S)OR8, C(=NR 7)R7a, C(=NR 7)NR 7aR 7 , Si(R11)2R12 phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R7b present on one ring carbon may together form =0, =S or =CR13R14, or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and NR17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=NR17; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 radicals R10; independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, C(=0)R15, C(=0)N R 7aR 7b, C(=S)N R 7aR 7b, C(=0)OR16, 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 R10, 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 R10, 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 Ci-C6-alkyl, C3-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the five last mentioned radicals are unsubstituted, partly or completely halogenated,
phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, R9a, R9b 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, C1-C6- alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl,
S(0)nR16, -S(0)nN R 7aR 7 , C(=0)R15, C(=0)OR16, C(=0)N R 7aR 7 , C(=S)R15, C(=S)SR16, C(=S)N R 7aR 7b, C(=N R 7)R15;
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 R10; and
a 3-, 4-, 5-, 6- or 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or,
R9a and R9b 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, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or
R9a and R9 together may form =CR13R14, =N R17, =NOR16, =N N R17aR17 moiety;
R10 independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN , SF5, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-C10- alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cydoaliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals R10a,
Si(R11)2R12, OR16, OS(0)nR16, -S(0)nR16, S(0)nNR 7aR 7b, NR17aR17b, C(=0)R15, C(=S)R15, C(=0)OR16, -C(=NR 7)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b,
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; or
two R10 present together on one carbon ring atom of a saturated or partly
unsaturated heterocyclic radical may form =0, =CR13R14, =S, =NR17, =NOR16, =NNR17aR17b;
or,
two R10 on adjacent carbon ring atoms may also be a bivalent radical selected from CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S,
CH=CHS, CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2NR17, CH2CH=N, CH=CH-NR17, OCH=N, SCH=N and form together with the carbon atoms to which the two R10 are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3,
OCH3, halogen, cyano, halomethyl and halomethoxy; independently of its occurrence, is selected from the group consisting of halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl,
Si(R11)2R12, OR16, OS(0)nR16, -S(0)nR16, S(0)nNR 7aR 7 , NR17aR17b, C(=0)R15, C(=S)R15, C(=0)OR16, -C(=NR 7)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b,
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;
R11 , R12 independently of their occurrence, are selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8-halocycloalkyl-Ci-C4-alkyl, C1-C6- haloalkoxy-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals are unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH , cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy and Ci-C6-haloalkoxy; R13, R14 independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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; 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,
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;
R17 independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, trimethylsilyl, triethylsilyl, te/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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, 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,
R17a, R17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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,
or,
R17a and R17b 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 R17a and R17b 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-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
R17a and R17b together may form =CR13R14, =NR17 or =NOR16 moiety; R17c independently of its occurrence, is selected from the group consisting of hydrogen, CN , d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci- C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from 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; the stereoisomers, tautomers and the salts thereof.
One embodiment of the present invention relates to N-acylimino compound of formula (I): wherein m is an integer selected from 0, 1 , 2, 3, 4, 5 and 6; X1 is O or S; X2 is CN or N02;
Het is a 5- or 6-membered carbon-bound or nitrogen-bound heterocyclic or heteroaromatic 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 R6, wherein k is an integer selected from 0, 1 , 2, 3 and 4;
W1 represents O, S or NRw1;
W2-W3-W4 represents a bivalent radical selected from -C(Rv2Rw2)-C(Rv3Rw3)-, -C(Rv4)=C(Rv5)- and -C(Rv2Rw2)-0-C(Rv3Rw3)-;
?w1 is selected from the group consisting hydrogen, cyano, nitro, SCN , Ci-Cio-alkyl, C3- Ce-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 R7,
OR8, NR9aR9b, S(0)nR8, S(0)nNR9aR9b, C(=0)R7a, C(=0)NR9aR9b, C(=0)OR8, C(=S)R7a, C(=S)NR9aR9b, C(=S)OR8, C(=S)SR8, C(=NR 7)R7a and C(=NR 7)NR9aR9 ; each Rv2, Rv3 independently from each other, are selected from the group consisting 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 R7; each Rv4, Rv5 are independently from each other selected from the group consisting hydrogen, halogen, cyano, azido, nitro, SCN, SF5, 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 R7,
OR8, NR9aR9 , S(0)nR8, S(0)nNR9aR9 , C(=0)R7a, C(=0)NR9aR9 , C(=0)OR8, C(=S)R7a, C(=S)NR9aR9 , C(=S)OR8, C(=S)SR8, C(=NR 7)R7a, C(=NR 7)NR9aR9 and Si(R11)2R12, each Rw2, Rw3 are independently from each other selected from the group consisting hydrogen, cyano, nitro, SCN, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-C10- 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 R7, C(=0)R7a, C(=0)NR9aR9 , C(=0)OR8, C(=S)R7a, C(=S)NR9aR9 , C(=S)OR8,
C(=S)SR8, C(=NR 7)R7a and C(=NR 7)NR9aR9 ,
, R2 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 R7,
Si(R11)2R12, OR8, OSO2R8, S(0)nR8, S(0)nNR9aR9 , NR9aR9 , C(=0)NR9aR9 ,
C(=S)NR aR , C(=0)OR8, C(=0)R7a, C(=S)R7a, phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
R1 and R2 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 R7,
or
R and R2 may together be =0, =CR13R14, =S, =NR17, =NOR16 or =NNR9aR9b; is selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated or carries 1 or 2 radicals R7, it being also possible for cycloalkyl to carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
S(0)nNR9aR9b, NR9aR9b, C(=0)OR8, C(=0)NR9aR9b, C(=S)NR9aR9 , C(=0)R7a, C(=S)R7a, NR9a-C(=0)R7a, NR9a-C(=S)R7a, NR9a-S(0)nR8a,
phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
R4b are selected each independently from one another and independently from the integer of m from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C1-C6- alkoxy, Ci-C6-alkylthio, and Cs-Cs-cycloalkyl, wherein each of the four last mentioned radicals are unsubstituted, partly or completely halogenated,
or R4a and R4b may form together with the carbon atom they are bound to, a 3-, 4-, 5- or 6- membered aliphatic ring, wherein each of the carbon atoms of the ring may be
unsubstituted or may be partly or fully halogenated, and/or may carry 1 , 2, 3, 4, 5 or 6 radicals selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
R4a and R4b may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b, is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2- Ce-alkynyl, C3-C8-cycloalkyl, 0-Ci-C6-alkyl, 0-C2-C6-alkenyl, 0-C2-C6-alkynyl, 0-C3-C8- cycloalkyl, S(0)n-Ci-C6-alkyl, S(0)n-C2-C6-alkenyl,
S(0)n-C2-C6-alkynyl, S(0)n-C3-C8-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl parts of each of the 12 last mentioned radicals are unsubstituted, partly or completely halogenated or carries 1 or 2 radicals R7, it being also possible for cycloalkyl radicals to carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups,
S(0)nNR9aR9b, NR9aR9 , C(=0)OR8, C(=0)NR9aR9 , C(=S)NR9aR9 , C(=0)R7a, C(=S)R7a, 0-C(=0)OR8, 0-C(=0)NR9aR9 , 0-C(=S)NR9aR9 , 0-C(=0)R7a, 0-C(=S)R7a,
NR9a-C(=0)R7a, NR9a-C(=S)R7a, NR9a-S(0)nR8a, a moitey Q-phenyl, where the phenyl ring is optionally substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R10,
and a moiety Q-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 R10, 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, O, S, S(O), S(0)2, NR9a,
-0-S(=0)2-, -NR a-S(=0)2-, -0-C(=0)-, -NR a-C(=0)-, -0-Ci-C4-alkylene,
-S-Ci-C4-alkylene, -S(0)-Ci-C4-alkylene, S(0)2-Ci-C4-alkylene, -NR9a-Ci-C4- alkylene, -0-C(=0)-Ci-C4-alkylene or
Figure imgf000019_0001
where the heteroatom in the last 7 moieties is bound to the carbon atom of C(X2)R3 or CR4aR4a, respectively; or, if m = 0,
R3 and R5 together may also form with the carbon atom they are bound to, a 3-, 4-, 5- or 6- membered saturated partially unsaturated carbocycle or heterocycle, wherein the carbocycle or heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, and where the heterocycle 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-R17c, or R3 and R5 may together form =0 or =S; where, independently of their occurrence, n is 0, 1 or 2;
R6 is selected from the group consisting of halogen, cyano, azido, nitro, SCN , SF5, Ci- Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be further substituted independently from one another with 1 , 2 or 3 radicals R7, OR8, NR17aR17b, S(0)nR8, S(0)nNR 7aR 7b, C(=0)R7a, C(=0)NR 7aR 7b, C(=0)OR8,
C(=S)R7a, C(=S)NR 7aR 7 , C(=S)OR8, C(=S)SR8, C(=NR 7)R7a, C(=NR 7)NR 7aR 7 , Si(R11)2R12;
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents
R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R6 present on one ring carbon may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b,
or two R6 together form a linear C2-C7 alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and NR17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=NR17; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6-haloalkynyl, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 radicals R10; independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF5, Ci-Ce-alkyI, Ci-C6-haloalkyl, C3-C8-cycloalkyl, Cs-Cs- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Si(R11)2R12, OR8, OSO2R8, S(0)nR8, S(0)nNR 7aR 7b, NR17aR17b, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, C(=0)OR8, C(=0)R15, C(=S)R15, C(=NR 7)R15,
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 R10, 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two R7 present on one carbon atom may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b,
or two R7 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 R7 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 R10; 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, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, 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 R10, 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-Cio-alkyl, Cs-Cs- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C3-Cs-cycloalkenyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be partly or completely halogenated, and/or be substituted with 1 , 2,3 or 4, in particular 1 , 2 or 3, identical or different radicals R7,
OR8, N R17aR17b, S(0)nR8, S(0)nN R 7aR 7b, C(=0)R7a, C(=0)N R 7aR 7b, C(=0)OR8, C(=S)R7a, C(=S)N R 7aR 7b, C(=S)OR8, C(=N R 7)R7a, C(=N R 7)N R 7aR 7 , Si(R1 1)2R12 phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R7b present on one ring carbon may together form =0, =S or =CR13R14, or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and N R17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=N R17; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs- Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 radicals R10; independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, C(=0)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7 , C(=0)OR16, 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 R10, 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 R10, 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 Ci-C6-alkyl, Cs-Cs-cycloalkyI, C3-C8-cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the five last mentioned radicals are unsubstituted, partly or completely halogenated,
phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
R9b 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, C1-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,
S(0)nR16, -S(0)nN R 7aR 7 , C(=0)R15, C(=0)OR16, C(=0)N R 7aR 7 , C(=S)R15, C(=S)SR16, C(=S)N R 7aR 7b, C(=N R 7)R15;
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 R10; and
a 3-, 4-, 5-, 6- or 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or,
R9a and R9b 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, Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci- C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or
R9a and R9 together may form =CR13R14, =N R17, =NOR16, =N N R17aR17 moiety;
R10 independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN , SF5, 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 R10a,
Si(R11)2R12, OR16, OS(0)nR16, -S(0)nR16, S(0)nNR 7aR 7b, NR17aR17b, C(=0)R15, C(=S)R15, C(=0)OR16, -C(=NR 7)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b,
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; or
two R10 present together on one carbon ring atom of a saturated or partly
unsaturated heterocyclic radical may form =0, =CR13R14, =S, =NR17, =NOR16, =NNR17aR17b;
or,
two R10 on adjacent carbon ring atoms may also be a bivalent radical selected from CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S,
CH=CHS, CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2NR17, CH2CH=N, CH=CH-NR17, OCH=N, SCH=N and form together with the carbon atoms to which the two R10 are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3,
OCH3, halogen, cyano, halomethyl and halomethoxy;
R10a independently of its occurrence, is selected from the group consisting of halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Si(R11)2R12, OR16, OS(0)nR16, -S(0)nR16, S(0)nNR 7aR 7b, NR17aR17b, C(=0)R15, C(=S)R15, C(=0)OR16, -C(=NR 7)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b,
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;
R11, R12 independently of their occurrence, are selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8-halocycloalkyl-Ci-C4-alkyl, C1-C6- haloalkoxy-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy;
R13, R14 independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl; R15 independently of its occurrence, is selected from the group consisting of hydrogen,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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; 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-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;
R17 independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, trimethylsilyl, triethylsilyl, te/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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, 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,
R17a, R17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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,
or,
R17a and R17b 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 R17a and R17b 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-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
R17a and R17b together may form =CR13R14, =NR17 or =NOR16 moiety; R17c independently of its occurrence, is selected from the group consisting of hydrogen, CN, d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci- C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from 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; the stereoisomers, the tautomers and the salts thereof.
Moreover, the present invention relates to and includes the following embodiments:
agricultural and veterinary compositions comprising an amount of at least one compound of the formula (I) or a stereoisomer, tautomer or salt thereof;
the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts thereof for combating invertebrate pests;
the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts thereof for protecting growing plants from attack or infestation by invertebrate pests;
the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts, thereof for protecting plant proparagation material, especially seeds, from soil insects; the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts thereof for protecting the seedlings roots and shoots of plants from soil and foliar insects; a method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of the formula (I) or a stereoisomer, a tautomer or salt thereof;
a method for protecting growing plants from attack or infestation by invertebrate pests, which method 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;
- the use of compounds of formula (I), the stereoisomers, the tautomers or the salts, in particular the veterinary acceptable salts, thereof for combating parasites in and on animals, in particular for the use in the treatment of animals infested or infected by parasites, for preventing animals of getting infected or infested by parasites or for protecting animals against infestation or infection by parasites;
- 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 parasiticidally 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 use of a compound of formula (I) or the stereoisomers, tautomers and/or veterinary acceptable salt thereof for the preparation of a medicament for treating, controlling, preventing or protecting animals against infestation or infection by parasites.
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.
Detailed Description of Invention
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. Depending on the substitution pattern, 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 R1. Another centre of chirality may be the carbon atom which carries R3, in particular if R3 is different from CN and the group [CR4aR4b]mR5. 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. Suitable compounds of the formula (I) also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
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 invention includes both amorphous and crystalline compounds of the formula (I), mixtures of different crystalline states or modifications of the respective
stereoisomers or tautomers, as well as amorphous or crystalline salts thereof.
Salts of the compounds of the formula (I) are preferably agriculturally salts as well as 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. Examples of substituted ammonium ions comprise methylammonium, 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 Ci- 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 Cn- 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.
The term "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. For example, 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 is also termed haloalkthio, partially or fully halogenated alkylsulfinyl is also termed haloalkylsulfinyl, partially or fully halogenated alkylsulfonyl is also termed haloalsulfonyl, partially or fully halogenated cycloalkylalkyl is also termed halocycloalkylalkyl.
The term "Cn-Cm-alkyl" as used herein, and also in Cn-Cm-alkylamino, di-Cn-Cm-alkylamino, Cn-Cm-alkylaminocarbonyl, di-(Cn-Cm-alkylamino)carbonyl, Cn-Cm-alkylthio (also referred to as Cn-Cm-alkylsulfanyl) , Cn-Cm-alkylsulfinyl and Cn-Cm-alkylsulfonyl, refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g. 1 to 10 carbon atoms (C1-C10- alkyl), preferably 1 to 6 carbon atoms (Ci-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-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 - methylpropyl, 1 -ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 - methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.
The term "Cn-Cm-haloalkyl" as used herein, and also in Cn-Cm-haloalkylthio (= Cn-Cm- haloalkylsulfanyl), Cn-Cm-haloalkylsulfinyl and Ci-Cm-haloalkylsulfonyl, refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g. 1 to 10 in particular 1 to 6 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C4-haloalkyl, such as chloromethyl, 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,
pentafluoroethyl and the like. The term Ci-Cio-haloalkyl in particular comprises C1-C2- fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, 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.
The term "Ci-Cm-alkoxy" is a Ci-Cm-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.
The term "Ci-Cm-alkylthio" is a Ci-Cm-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). C1-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, 3,3-dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1 ,1 ,2-trimethylpropylthio, 1 ,2,2- trimethylpropylthio, 1 -ethyl-1 -methylpropylthio or 1-ethyl-2-methylpropylthio. Ci-Cs-Alkylthio includes the meanings given for Ci-C6-alkylthio and also includes, for example, heptylthio, octylthio, 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.
The term "Ci -Cm-a I ky I su If i nyl" is a Ci-Cm-alkyl group, as defined above, attached via a S(=0) group.
The term "Ci-Cm-alkylsulfonyl" is a Ci-Cm-alkyl group, as defined above, attached via a S(=0)2 group.
The term "Ci-Cm-haloalkyloxy" (also referred to as Ci-Cm-haloalkoxy) is a Ci-Cm-haloalkyl group, as defined above, attached via an oxygen atom. Examples include Ci-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy,
chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy.
The term "Ci-Cm-haloalkylthio" (also referred to as haloalkylsulfanyl) is a Ci-Cm-haloalkyl group, as defined above, attached via a sulfur atom. Examples include Ci-C2-haloalkylthio, such as chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, 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- difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio and the like.
Similarly the terms 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.
The term "Ci-Cm-haloalkylsulfinyl" is a Ci-Cm-haloalkyl group, as defined above, attached via a S(=0) group. The term "Ci-Cm-haloalkylsulfonyl" is a Ci-Cm-haloalkyl group, as defined above, attached via a S(=0)2 group.
The term "C2-Cm-alkenyl" as used herein denotes a linear or branched ethylenically unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and a C=C- double bond in any position, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methyl-ethenyl, 1 - butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2- methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl- 1 -butenyl, 3-methyl-1 -butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 - methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1 -dimethyl-2-propenyl, 1 ,2-dimethyl-
1 - propenyl, 1 ,2-dimethyl-2-propenyl, 1 -ethyl-1 -propenyl, 1 -ethyl-2-propenyl, 1 -hexenyl, 2- hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl-1 -pentenyl, 2-methyl-1 -pentenyl, 3-methyl- 1 -pentenyl, 4-methyl-1 -pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2- pentenyl, 4-methyl-2-pentenyl, 1 -methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl- 4-pentenyl, 1 ,1 -dimethyl-2-butenyl, 1 ,1 -dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-dimethyl-
2- butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1 -butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl- 3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-
3- butenyl, 3, 3-dimethyl-1 -butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1 -ethyl-2-butenyl, 1 - ethyl-3-butenyl, 2-ethyl-1 -butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2- propenyl, 1 -ethyl-1 -methyl-2-propenyl, 1 -ethyl-2-methyl-1 -propenyl and 1 -ethyl-2-methyl-2- propenyl.
The term "C2-Cm-haloalkenyl" as used herein, which is also expressed as "C2-Cm-alkenyl which is partially or fully halogenated", refers to C2-Cm-alkenyl as defined above, 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, 2,2,-dichloroethenyl, 1 -chloro-2-propenyl, and the like.
The term "C2-Cm-alkynyl" as used herein refers to a linear or branched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1 -butynyl, 2-butynyl, and the like.
The term "C2-Cm-haloalkynyl" as used herein, which is also expressed as "C2-Cm-alkynyl which is partially or fully halogenated", refers to C2-Cm-alkynyl as defined above, 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-Cm-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.
The term "C3-Cm-cycloalkyl" as used herein refers to a monocyclic, bicyclic and polycyclic
3- to m-membered saturated cycloaliphatic radicals, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, bicyclo[2.2.1 ]heptyl, bicyclo[3.3.1]heptyl, bicyclo- [3.1.1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical. The term "C3-Cm-halocycloalkyl" as used herein, which is also expressed as "cycloalkyl which is partially or fully halogenated", refers C3-Cm-cycloalkyl as mentioned above, in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine. Examples of C3-Cm-halocycloalkyl include 1 - fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 1 -chlorocyclcopropyl, 2- chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,3-difluorocyclopropyl, 1 -fluorocycobutyl etc.
The term "C3-Cm-cycloalkyl-Ci-C4-alkyl" refers to a C3-Cm-cycloalkyl group as defined above, which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above. Examples for C3-Cm-cycloalkyl-Ci-C4-alkyl are cyclopropyl methyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
The term "C3-Cm-halocycloalkyl-Ci-C4-alkyl" refers to a C3-Cm-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
The term "Ci-C4-alkoxy-Ci-C4-alkyl" as used herein 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 - isopropoxypropyl, 1 -n-butoxypropyl, 1 -sec-butoxypropyl, 1 -isobutoxypropyl, 1 -tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl, 2- sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3- propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl, 3- tert-butoxypropyl and the like.
The term 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.
The term "Ci-Cm-alkoxycarbonyl" is a Ci-Cm-alkoxy group, as defined above, attached via a carbonyl group to the remainder of the moleculae. Ci-C2-Alkoxycarbonyl is methoxycarbonyl or ethoxycarbonyl. Ci-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 Ci-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, hexoxycarbonyl, 1 -methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1 ,1 -dimethylbutoxycarbonyl, 1 ,2- dimethylbutoxycarbonyl, 1 ,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3- dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1 -ethylbutoxy, 2-ethylbutoxycarbonyl, 1 ,1 ,2-trimethylpropoxycarbonyl, 1 ,2,2-trimethylpropoxycarbonyl, 1 -ethyl-1 - methylpropoxycarbonyl or 1 -ethyl-2-methylpropoxycarbonyl.
The term "cycloalkenyl" as used herein refers to monocyclic hydrocarbon radicals with at least one C-C double bond in the ring, which ring is however not aromatic, the hydrocarbon radicals having 3 to 8 ("Cs-Cs-cycloalkenyl) carbon atoms. Examples are cyclopropenyl, such as cycloprop-1 -enyl and cycloprop-2-enyl, cyclobutenyl, such as cyclobut-1 -enyl and cyclobut-2- enyl, cyclopentenyl, such as cyclopent-1 -enyl, cyclopent-2-enyl and cyclopent-3-enyl, cyclopentadienyl, such as cyclopenta-1 ,3-dienyl, cyclpenta-1 ,4-dienyl and cyclpenta-2,4-dienyl, cyclohexenyl, such as cyclohex-1 -enyl, cyclohex-2-enyl and cyclohex-3-enyl, cyclohexadienyl, such as cyclohexa-1 ,3-dienyl, cyclohexa-1 ,4-dienyl, cyclohexa-1 ,5-dienyl and cyclohexa-2,5- dienyl, cycloheptenyl, cycloheptadienyl, cycloheptatrienyl cyclooctenyl, cyclooctadieny, cyclooctatrienyl and cyclooctatetraenyl.
The term "aryl" as used herein refers to an aromatic hydrocarbon radical having usually 6 to 14 carbon atoms such as phenyl or naphthyl or in particular phenyl.
The term "3- to 6-membered carbocyclic ring" as used herein refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings. The term "3- to 7-membered carbocyclic ring" as used herein refers to cyclopropane, cyclobutane, cyclopentane, cyclohexane and cycloheptane rings.
The term "3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms" or "containing heteroatom groups" (also referred to as "3-, 4-, 5-, 6- or 7-membered saturated, partially saturated or (unsaturated) aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms" or "containing heteroatom groups"), wherein those heteroatom(s) (group(s)) are selected from N, O, S, NO, SO and SO2 and are ring members, as used herein refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic. The heterocyclic radical may be attached to the remainder of the 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
tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyrazolidinyl, 5-pyrazolidinyl, 2 imidazolidinyl, 4 imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4 isoxazolidinyl, 5 isoxazolidinyl, 2 thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3 isothiazolidinyl, 4- isothiazolidinyl, 5 isothiazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4 oxadiazolidin 5 yl, 1 ,2,4- thiadiazolidin-3-yl, 1 ,2,4 thiadiazolidin-5-yl, 1 ,2,4 triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4 thiadiazolidin-2-yl, 1 ,3,4 triazolidin-2-yl, 2-tetrahydropyranyl, 4 tetrahydropyranyl, 1 ,3-dioxan-5- yl, 1 ,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4 hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5 hexahydropyrimidinyl,
2- piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4 hexahydrotriazin-3-yl, 2-morpholinyl, 3- morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1 -oxothiomorpholin-2-yl, 1 -oxothiomorpholin-
3- yl, 1 ,1 -dioxothiomorpholin-2-yl, 1 ,1 -dioxothiomorpholin-3-yl, hexahydroazepin-1 -, -2-, -3- or -4- yl, hexahydrooxepinyl, hexahydro-1 ,3-diazepinyl, hexahydro-1 ,4-diazepinyl, hexahydro-1 ,3- oxazepinyl, hexahydro-1 ,4-oxazepinyl, hexahydro-1 ,3-dioxepinyl, hexahydro-1 ,4-dioxepinyl and the like. Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3- dihydrothien-2-yl, 2,3 dihydrothien-3-yl, 2,4 dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2- yl, 2-pyrrolin-3-yl, 3 pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4 isoxazolin 3 yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2 isoxazolin-5-yl, 3-isoxazolin-5-yl, 4- isoxazolin-5-yl, 2-isothiazolin-3-yl, 3 isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3- isothiazolin-4-yl, 4 isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3 dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3 dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4 dihydropyrazol-3-yl, 3,4-dihydropyrazol-4- yl, 3,4-dihydropyrazol-5-yl, 4,5 dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-
4- yl, 4,5 dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3 dihydrooxazol- 4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4 dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 3,4-dihydrooxazol-5-yl, 3,4 dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4 di- or
tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5 di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1 ,3,5-di- or tetrahydrotriazin-2-yl, 1 ,2, 4-di- or tetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6- tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7 tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5- , -6- or -7-yl, 2,3,6,7 tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as 2,3,4, 5-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7 tetrahydro[1 H]oxepin-2- , -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7 tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1 ,3- diazepinyl, tetrahydro-1 ,4-diazepinyl, tetrahydro-1 ,3-oxazepinyl, tetrahydro-1 ,4-oxazepinyl, tetrahydro-1 ,3-dioxepinyl and tetrahydro-1 ,4-dioxepinyl.
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.
A "Cn-Cm-alkylene" is divalent branched or preferably non-branched or linear saturated aliphatic chain having n to m, e.g. 2 to 7 carbon atoms, for example CH2CH2, -CH(CH3)-,
CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2,
CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2.
Embodiments of the present invention as well preferred compounds of the present invention are outlined in the following paragraphs. The remarks made below concerning preferred embodiments of the variables of the compounds of formula (I), especially with respect to their substituents X1, X2, W1, W2, W3, W4, Het, R1 ,R2, R3, R4a, R4b and R5 and their variable k and m are valid both on their own and, in particular, in every possible combination with each other.
When # appears in a formula showing a preferred substructure of a compound of the present invention, it denotes the attachment of the bond in the remainder molecule.
Preferred are compounds of formula (I), wherein Het is selected from the group consisting of radicals of formulae Het-1 to Het-24, with preference given to compounds of the formula (I), their stereoisomers, there tautomers and their salts, where Het is selected from the radicals of the formulae Het-1 , Het-1 1 and Het-24:
Figure imgf000038_0001
Het-6 Het-7 Het-8 Het-9 Het-10
Figure imgf000038_0002
Het-11 Het-12 Het-13 Het-14 Het-15
Figure imgf000039_0001
-16 Het-17 Het-18 Het-19 Het-20
Figure imgf000039_0002
Het-21 Het-22 Het-23 Het-24 wherein # denotes the bond to the remainder of the molecule in formula (I), and wherein R6 and k are as defined above and where R6a is hydrogen or has one of the meanings given for R6 and where R6b is hydrogen or a C-bound radical mentioned as R6 and where R6b is in particular hydrogen, Ci-C4-alkyl or Ci-C4-haloalkyl. In particular k is 0, 1 or 2, especially 0 or 1. In formulae Het-1 , Het-2, Het-3, Het-4, Het-7, Het-8, Het-9, Het-10, Het-1 1 , Het-18 and Het-21 , k is especially 1. In particular R6a in formulae Het-12, Het-13, Het-14, Het-16, Het-17, Het-19, Het 20 and Het-22 is different from hydrogen.
Irrespectively of its occurrence, R6 is preferably selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may optionally be partly or completely halogenated, in particular by fluorine or chlorine, or may further substituted independently from one another with one or more R7, or R6 may also be a radical selected from the group consisting of OR8, NR17aR17b, S(0)nR8, S(0)nNR 7aR 7b, C(=0)R7a, C(=0)NR 7aR 7 , C(=0)OR8, C(=S)R7a, C(=S)NR 7aR 7 , C(=NR 7)R7a, C(=NR 7)NR 7aR 7 . Irrespectively of its occurrence, R6 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 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-trifluoroethyl or pentafluoroethyl.
Irrespectively of its occurrence, R6a is preferably selected from the group consisting of hydrogen, halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may optionally be partly or completely halogenated, in particular by fluorine or chlorine, or may further substituted independently from one another with one or more R7, or R6a may also be a radical selected from the group consisting of OR8, NR17aR17b, S(0)nR8, S(0)nNR17aR17b, C(=0)R7a, C(=0)NR 7aR 7b, C(=0)OR8, C(=S)R7a, C(=S)NR 7aR 7b, C(=NR 7)R7a,
C(=NR17)NR17aR17b. Irrespectively of its occurrence, R6a 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-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
Irrespectively of its occurrence, R6b 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.
Particularly preferred are compounds of formula (I), wherein Het is selected from the group consistin of radicals of formulae Het-1 , Het-1 1 a and Het-24,
Figure imgf000040_0001
Het-1 Het-11a Het-24 where
# denotes the bond to the remainder of the molecule in formula (I),
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 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-trifluoroethyl or pentafluoroethyl; and where 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, C1-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-trifluoroethyl or pentafluoroethyl and k is 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 R6 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 more preferably from fluorine, chlorine, 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. Amongst the compounds of this particular group of embodiments, 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
Figure imgf000041_0001
where
# denotes the bond to the remainder of the molecule in formula (I),
R6 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl or pentafluoroethyl;
R6a 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. R6a is hydrogen and R6 is chlorine. A further special embodiment of the radical Het-1 a is 6-(trifluoromethyl)pyridin-3- yl, i.e. R6a is hydrogen and R6 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,
Figure imgf000042_0001
where # denotes the bond to the remainder of the molecule in formula (I), R6a is as defined above and wherein R6a 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-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl. A special embodiment of the radical Het-1 1 a is 2-chlorothiazol-5-yl, i.e. R6a 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 R6, if present, is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci- C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
Preferred are compounds of formula (I), wherein R1 and R2 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.
Preferred are also compounds of formula (I), wherein R1 and R2 may together be
=CR13R14.
Preferred are also compounds of formula (I), wherein R1 and R2 form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl.
Even more preferred are compounds of formula (I), wherein R1 and R2 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.
Preferably at least one of the radicals R1 and R2 is hydrogen.
Especially more preferred are compounds of formula (I), wherein R1 and R2 are both hydrogen.
Especially more preferred are also compounds of formula (I), wherein one of R1 and R2 is methyl while the other is hydrogen.
According to a first group of embodiments A, compounds of formula (I) are preferred, wherein R3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, C3-C6-halocycloalkyl, such as 1 -fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 1 -fluorocyclobutyl, 2- fluorocyclobutyl, 3-fluorocyclobutyl, 2,2-difluorocyclobutyl or 3,3-difluorocyclobutyl, NR9aR9b and NR9a-C(=0)R7a.
In the context of R3, the radicals R7a is 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. In the context of R3, the radicals R9a and R9b 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 NR9aR9b 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-C4-alkyl and Ci- C4-haloalkyl. Examples of radicals NR9aR9b 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. Examples of radicals NR9aC(=0)R7a include, but are not limited NH-C(=0)H, NH-C(=0)CH3, NH-C(=0)CH2CH3 and
NH-C(=0)CH(CH3)2.
In this group of embodiments A, the radical R3 is in particular selected from the group consisting of hydrogen, fluorine, chlorine, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl or n-butyl, NH-C(=0)H, NHC(=0)-Ci-C4-alkyl, such as NH-C(=0)CH3, NH-C(=0)CH2CH3 or NH-C(=0)CH(CH3)2, and CN.
In this group of embodiments A, the radical R3 is especially selected from the group consisting of hydrogen and Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl or n-butyl.
In this group of embodiments A, preference is given to compounds of formula (I), wherein
R5 is selected from the group consisting of hydrogen, halogen, NR9aR9b, Ci-C6-alkyl, in particular Ci-C4-alkyl, Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, S-Ci-C6-alkyl, in particular S-C1-C4- alkyl, S-Ci-C6-haloalkyl, in particular S-Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, S-Cs-Ce-cycloalkyl, S-C3-C6-halocycloalkyl, C(=0)OR8, C(=0)NR aR b, C(=S)NR aR , C(=0)R7a, C(=S)R7a, Q-phenyl, where phenyl is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or Q-Het#, where Het# is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
and where Q, irrespectively of its occurrence, is a single bond, S, NR9a, such as NH or N(CH3), NR a-C(=0), such as NH-C(=0), NR a-C(=0)R7a, such as NH-C(=0)H, NH-C(=0)CH3, NH- C(=0)CH2CH3 or NH-C(=0)CH(CH3)2, OC(=0), NR aCH2, such as NHCH2 or N(CH3)CH2, OC(=0)CH2, or NR aC(=0)CH2 such as NHC(=0)CH2.
In context of R5, Het# is preferably 5- or 6-membered hetaryl such as pyridyl, thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxazolyl or isoxazolyl, which is
unsubstituted or substituted by 1 , 2 or 3 radicals R10. In this context, R10 is preferably selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci- C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
In context of R5, the radical R7a is preferably 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 unsubstituted 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, 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, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy. R7a is in particular Ci-C4-alkyl. In context of R5, the radical R8 is preferably 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 unsubstituted or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such 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-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy. R8 is in particular Ci-C4-alkyl.
In context of R5, the radicals R9a and R9b 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 NR9aR9b 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- C4-alkyl and Ci-C4-haloalkyl. Examples of such radicals NR9aR9b 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.
In context of R5, the phenyl ring is optionally substituted with 1 , 2, 3, 4, or 5 identical or different substituents R10. The radical R10 is preferably selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, 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-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
In this group of embodiments A, the radical R5 is in particular selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, Ci-C6-alkyl, in particular C1-C4- alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, S-d-Ce-alkyl, in particular S-Ci-C4-alkyl, such as methylthio, ethylthio, n-propylthio and isopropylthio, S-Ci-C6-haloalkyl, in particular S- Ci-C4-haloalkyl, such as fluoromethylthio, difluoromethylthio, trifluoromethylthio, 1 ,1 - difluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio or 2,2,2-trifluoroethylthio, C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, C3-C6-halocycloalkyl, such as 1 -fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2-chlorocyclopropyl, 2,2- dichlorocyclopropyl, 1 -fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 2,2- difluorocyclobutyl or 3,3-difluorocyclobutyl, S-C3-C6-cycloalkyl, such as cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio, -C3-C6-halocycloalkylsuch as 1 - fluorocyclopropylthio, 2-fluorocyclopropylthio, 2,2-difluorocyclopropylthio, 2- chlorocyclopropylthio, 2,2-dichlorocyclopropylthio, 1 -fluorocyclobutylthio, 2-fluorocyclobutylthio, 3-fluorocyclobutylthio, 2,2-difluorocyclobutylthio or 3,3-difluorocyclobutylthio, phenyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different substituents R10 and S-phenyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different substituents R10.
The variable m is preferably 0, 1 or 2, in particular with regard to the group of
embodiments A.
If R4a and R4b are present, i.e. if m is different from 0 and in particular 1 or 2, and especially 1 , the variables R4a and R4b are in particular selected, independently from one another, from the group consisting of hydrogen, Ci-C4-alkyl, in particular methyl, and halogen, in particular fluorine or chlorine, or R4a and R4b together are =0.
According to a second group of embodiments B, compounds of formula (I) are preferred, wherein
R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated carbocyle, in particular a 3-membered carbocycle, wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, wherein R7b is as defined above and wherein
R7b is in particular selected from the group consisting of halogen, Ci-C6-alkyl, C1-C6- alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by 1 or 2 radicals R7, and wherein one or two radicals R7b may also be C3-C8-cycloalkyl, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2,
3, 4 or 5 radicals selected from fluorine, chlorine, Ci-C4-alkyl such as methyl and Ci- C4-alkoxycarbonyl such as methoxycarbonyl,
C3-C6-cycloalkenyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl,
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents
R10, or 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, such as tetrahydrofuryl, tetrahydropyranyl, tetrahydrothiopyranyl or thiazolyl, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, in particular a 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N, where the 5- or 6-membered hetaryl is unsubstituted or carries 1 , 2 or 3 identical or different substituents R10, or two of R7b present on one ring carbon may together form =0 or =S,
or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
R7 is as defined above and in particular selected from Ci-C4-alkoxy, C1-C4- alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy, phenyl, phenoxy, 5- or 6- membered saturated heterocyclyl having 1 heteroatom selected from O and S, and 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N as ring memberes, where 5- or 6-membered saturated heterocyclyl and 5- or 6-mbered hetaryl may be unsubstituted or carry 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and C1-C4- haloalkoxy;
R10 is as defined above and in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy,
in particular, wherein
R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated carbocyle, in particular a 3-membered carbocycle, wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, wherein R7b is as defined above and wherein
R7b is in particular selected from the group consisting of halogen, Ci-C6-alkyl, C1-C6- alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by 1 or 2 radicals R7, wherein R7 is as defined above and has in particular one of the preferred meanings and
wherein one or two radicals R7b may also be
C3-C8-cycloalkyl, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or
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, such as tetrahydrofuryl, tetrahydropyranyl, tetrahydrothiopyranyl or thiazolyl, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, in particular a 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N, where the 5- or 6-membered hetaryl is unsubstituted or carries 1 , 2 or 3 identical or different substituents R10, or two of R7b present on one ring carbon may together form =0 or =S,
or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
R10 is as defined above and in particular selected from the group consisting of halogen,
Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
According to the second group of embodiments B, particular preference is given to compounds of formula (I), wherein
R3 and R5 together with the carbon atom, to which they are bound, form a 3- or 4-membered saturated carbocyle, i.e. a 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical, in particular a 1 ,1 -cyclopropylidene radical wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, wherein
R7b is as defined above and in particular selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxycarbonyl, and wherein one radical R7b may also be C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine, Ci-C4-alkyl such as methyl, or Ci-C4-alkoxycarbonyl, or phenyl, optionally substituted with 1 , 2, 3, 4 or 5, in particular 1 , 2 or 3, identical or different substituents R10, where
R10 is as defined above, and in particular selected from the group consisting of halogen, such as fluorine or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
According to the second group of embodiments B, more preference is given to
compounds of formula (I), wherein
R3 and R5 together with the carbon atom, to which they are bound, form a 3- or 4-membered saturated carbocyle, i.e. a 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical, in particular a 1 ,1 -cyclopropylidene radical wherein each of the carbon atoms of the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, wherein R7b is as defined above and in particular selected from the group consisting of halogen, Ci-C4-alkyl, and wherein one radical R7b may also be
phenyl, optionally substituted with 1 , 2, 3, 4 or 5, in particular 1 , 2 or 3, identical or different substituents R10, where
R10 is as defined above, and in particular selected from the group consisting of halogen, such as fluorine or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
According to the second group of embodiments B, even more particular preference is given to compounds of formula (I), wherein R3 and R5 together form the following moieties: CH2-CH2, CHF-CH2, CF2-CH2, CHF-CHF, CF2-CH F, CF2-CF2, CHCI-CH2, CCI2-CH2,
CHCI-CHCI, CC -CHCI, CCI2-CCI2, CH(CH3)-CH2, C(CH3)2-CH2, CH(CH3)-CH(CH3),
C(CH3)2-CH(CH3), C(CH3)2-C(CH3)2, CH(OCH3)-CH2, CH(CH2CH3)-CH2, CH(CH2CH2CH3)-CH2, CH(CH2CH2CH2CH3)-CH2, CH(CH3)-CH2-CH2, CH2-CH(CH3)-CH2, C(CH3)2-CH2-CH2,
CH2-C(CH3)2-CH2, CH(CH3)-CH(CH3)-CH2, CH(CH3)-CH2-CH(CH3),
CH(CH3)-CH(CH3)-CH(CH3), C(CH3)2-CH(CH3)-CH2, CH(CH3)-C(CH3)2-CH2,
C(CH3)2-CH2-C(CH3)2, C(CH3)2-C(CH3)2-CH2, C(CH3)2-C(CH3)2-C(CH3)2, CHF-CH2-CH2, CH2-CHF-CH2, CF2-CH2-CH2, CH2-CF2-CH2, CHF-CHF-CH2, CHF-CH2-CHF, CHF-CHF-CHF, CF2-CHF-CH2, CHF-CF2-CH2, CF2-CH2-CF2, CF2-CF2-CH2, CF2-CF2-CF2, CHCI-CH2-CH2, CH2-CHCI-CH2, CCI2-CH2-CH2, CH2-CCI2-CH2, CHCI-CHCI-CH2, CHCI-CH2-CHCI,
CHCI-CHCI-CHCI, CCI2-CHCI-CH2, CHCI-CCI2-CH2, CCI2-CH2-CCI2, CCI2-CCI2-CH2,
Figure imgf000049_0001
a radical CH(R7bb)-CH2, where R7bb is selected from the group consisting of
Ci-C6-alkyl, in particular C2-C6-alkyl, such as ethyl, n-propyl, isopropyl, n-butyl, tert.butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3- dimethylpropyl, 1 -methylbutyl, 1 ,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl, , Ci-C6-haloalkyl, in particular C2-C4-haloalkyl, such as 2,2-difluoroethyl, 1 ,1 - difluoroethyl or 2,2,2-trifluoroethyl,
Ci-C6-alkoxy such as methoxy, ethoxy, propoxy;
Ci-C6-alkyl, which is substituted by 1 radical selected from Ci-C4-alkoxy, C1-C4- alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Cs-Cs-cycloalkyl, C3- Cs-cycloalkoxy, phenoxy and 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothiopyranyl, where Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy and 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples of substituted Ci-C6-alkyl including 1 -methoxyethyl, 2-methoxyethyl, 1 -propoxyethyl, 2-propoxyethyl, 1 - isopropoxyethyl, 2-isopropoxyethyl, 1 -isobutoxyethyl, 2-isobutoxyethyl, 1 - (cyclohexyloxy)ethyl, 2-phenoxyethyl, (4-isopropylcyclohexyl)methyl, 1 -acetoxyethyl,
2- acetoxyethyl, 6-acetoxyhexyl, 2-methylsulfanylpropyl, 1 -methyl-2- methylsulfanylethyl, tetrahydropyran-4-ylmethyl, tetrahydrothiopyran-4-ylmethyl,
C2-Cio-alkenyl, such as 3-nonenyl,
C2-C6-alkynyl such as ethynyl;
C3-Cio-cycloalkyl, optionally substituted by 1 or 2 Ci-C4-alkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 4-methylcyclohexyl, 4- isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl,
C5-C6-cycloalkenyl, optionally substituted by 1 or 2 Ci-C4-alkyl, such as 2- methylcyclohex-3-en-1 -yl,
5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6-membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tehtrahydrothiopyran-
3- yl, tetrahydrothiopyran-4-yl, 6-methoxy-3-methyltetrahydropyran-2-yl, and 5,5- dimethyltetrahydrofuran-2-yl,
optionally substituted phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl, 3- (trifluoromethyl)phenyl and 4-cyanophenyl,
5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy examples of hetaryl including 4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl, phenyl-Ci-C4-alkyl, such as benzyl or phenethyl, and
hetaryl-Ci-C4-alkyl, where the hetaryl is 5- or 6-membered and has 1 or 2
heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy examples of hetaryl-Ci-C4-alkyl including 1 ,1 -dimethyl-2-(3-pyridyl)ethyl,
thereby forming, together with the carbon atom they are bound to, an unsubstituted or substituted 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical.
According to the second group of embodiments B, even more particular preference is given to compounds of formula (I), wherein R3 and R5 together form the following moieties: CH2-CH2, CHF-CH2, CF2-CH2, CHF-CHF, CF2-CHF, CF2-CF2, CHCI-CH2, CCI2-CH2,
CHCI-CHCI, CC -CHCI, CCI2-CCI2, CH(CH3)-CH2, C(CH3)2-CH2, CH(CH3)-CH(CH3),
C(CH3)2-CH(CH3), C(CH3)2-C(CH3)2, CH(OCH3)-CH2, CH(CH2CH3)-CH2, CH(CH2CH2CH3)-CH2, CH(CH2CH2CH2CH3)-CH2, CH(CH3)-CH2-CH2, CH2-CH(CH3)-CH2, C(CH3)2-CH2-CH2,
CH2-C(CH3)2-CH2, CH(CH3)-CH(CH3)-CH2, CH(CH3)-CH2-CH(CH3),
CH(CH3)-CH(CH3)-CH(CH3), C(CH3)2-CH(CH3)-CH2, CH(CH3)-C(CH3)2-CH2,
C(CH3)2-CH2-C(CH3)2, C(CH3)2-C(CH3)2-CH2, C(CH3)2-C(CH3)2-C(CH3)2, CHF-CH2-CH2, CH2-CHF-CH2, CF2-CH2-CH2, CH2-CF2-CH2, CHF-CHF-CH2, CHF-CH2-CHF, CHF-CHF-CHF, CF2-CHF-CH2, CHF-CF2-CH2, CF2-CH2-CF2, CF2-CF2-CH2, CF2-CF2-CF2, CHCI-CH2-CH2, CH2-CHCI-CH2, CCI2-CH2-CH2, CH2-CCI2-CH2, CHCI-CHCI-CH2, CHCI-CH2-CHCI,
CHCI-CHCI-CHCI, CCI2-CHCI-CH2, CHCI-CCI2-CH2, CCI2-CH2-CCI2, CCI2-CCI2-CH2,
Figure imgf000051_0001
or a radical CH(Ar)-CH2, where Ar is selected from phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl and 4-cyanophenyl,
thereby forming, together with the carbon atom they are bound to, an unsubstituted or substituted 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical.
According to the second group of embodiments B, special preference is given to compounds of formula (la)
Figure imgf000051_0002
where Het, W, W2, W3, W4, X1, X2, R1 and R2 are as defined above and in particular have the preferred meanings or the particularly preferred meanings; and where
R7b1 is hydrogen or has one of the meanings given for R7b;
R7b2, R7b3 and R7b4 are hydrogen, methyl or halogen, in particular hydrogen.
In formula (la), R7b1 is in particular hydrogen or a radical selected from the group consisting of Ci-C6-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert. butyl, 1 - methylpropyl, 2-methylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3- dimethylpropyl, 1 -methylbutyl, 1 ,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl,
Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 1 ,1 - difluoroethyl or 2,2,2-trifluoroethyl,
Ci-C6-alkyl, which is substituted by 1 radical selected from Ci-C4-alkoxy, C1-C4- alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Cs-Cs-cycloalkyl, C3- Cs-cycloalkoxy, phenoxy and 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothiopyranyl, where Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy and 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples of substituted Ci-C6-alkyl including 1 -methoxyethyl, 2-methoxyethyl, 1 -propoxyethyl, 2-propoxyethyl, 1 - isopropoxyethyl, 2-isopropoxyethyl, 1 -isobutoxyethyl, 2-isobutoxyethyl, 1 - (cyclohexyloxy)ethyl, 2-phenoxyethyl, (4-isopropylcyclohexyl)methyl, 1 -acetoxyethyl,
2- acetoxyethyl, 6-acetoxyhexyl, 2-methylsulfanylpropyl, 1 -methyl-2- methylsulfanylethyl, tetrahydropyran-4-ylmethyl, tetrahydrothiopyran-4-ylmethyl,
C2-Cio-alkenyl, such as 3-nonenyl,
C2-C6-alkynyl, such as ethynyl;
C3-Cio-cycloalkyl, optionally substituted by halogen and/or Ci-C4-alkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 4- methylcyclohexyl, 4-isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
C5-C6-cycloalkenyl, optionally substituted by 1 or 2 Ci-C4-alkyl, such as 2- methylcyclohex-3-en-1 -yl,
5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6-membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tehtrahydrothiopyran-
3- yl, tetrahydrothiopyran-4-yl, 6-methoxy-3-methyltetrahydropyran-2-yl, and 5,5- dimethyltetrahydrofuran-2-yl,
optionally substituted phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl, 3- (trifluoromethyl)phenyl and 4-cyanophenyl,
5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy examples of hetaryl including 4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl, phenyl-Ci-C4-alkyl, such as benzyl or phenethyl, and
hetaryl-Ci-C4-alkyl, where the hetaryl is 5- or 6-membered and has 1 or 2
heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substituted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, examples of hetaryl-Ci-C4-alkyl including 1 ,1 -dimethyl-2-(3-pyridyl)ethyl.
According to a third group of embodiments C, compounds of formula (I) are preferred, wherein R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6-membered saturated heterocycle having 1 or 2 non adjacent heteroatoms as ring memberes which are selected from O and S, wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, wherein
R7b is as defined above and in particular as defined for embodiment B and especially selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4- alkyl, Ci-C4-alkoxycarbonyl,
and wherein one radical R7b may also be
C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine, Ci-C4-alkyl such as methyl, or Ci-C4-alkoxycarbonyl, or
phenyl, optionally substituted with 1 , 2, 3, 4 or 5, in particular 1 , 2 or 3, identical or different substituents R10, where
R10 is as defined above, and in particular selected from the group consisting of halogen, such as fluorine or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
According to the third group of embodiments C, even more particular preference is given to compounds of formula (I), wherein R3 and R5 together form 0-Ci-C3-alkylene, wherein 1 , 2, 3 or 4 of the hydrogen atoms in Ci-C3-alkylene may be replaced by R7b, thereby forming, together with the carbon atom they are bound to, an unsubstituted or substituted saturated 3-, 4- or 5- membered heterocyclic radical having 1 oxygen atom as ring member. According to the third group of embodiments C, even more particular preference is given to compounds of formula (I), wherein R3 and R5 together form O-CH2 or O-CH2CH2, wherein 1 , 2, 3 or 4 of the hydrogen atoms in CH2 or CH2CH2, may be replaced by R7b, thereby forming, together with the carbon atom they are bound to, an unsubstituted or substituted oxiran-2,2-diyl or oxetan-2,2-diyl.
According to a fourth group of embodiments D, compounds of formula (I) are preferred, wherein R3 and R5 together form =S or =0, in particular =0.
Preferred are compounds of formulae (I) and (la), wherein W is S. Likewise preferred are compounds of formulae (I) and (la), wherein W is O. Likewise preferred are compounds of formulae (I) and (la), wherein W is NRw1. In this context, Rw1 is 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, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C4-alkoxy-Ci-C4-alkyl, in particular Ci-C2-alkoxy-Ci-C2-alkyl such as methoxymethyl, ethoxymethyl, methoxyethyl or ethoxyethyl, Ci-C4-alkylcarbonyl, in particular Ci-C2-alkylcarbonyl such as methylcarbonyl (acetyl) or ethylcarbonyl, and Ci-C4-haloalkylcarbonyl, in particular Ci-C2-haloalkylcarbonyl. More preferably, Rw1 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-alkylcarbonyl. In particular, Rw1 is hydrogen, methyl or methylcarbonyl (acetyl). In particular preference is given to cmpounds of formulae (I) and (la), wherein Rw1 is hydrogen or methyl, especially hydrogen.
A further preferred group of embodiments relates to compounds of formulae (I) and (la), wherein W2-W3-W4 is a bivalent radical -C(Rv2Rw2)-C(Rv3Rw3)-, in which the carbon atom which carries Rv2 and Rw2 is attached to W1. In this context, Rv2, Rw2, Rv3 and Rw3 are independently from each other preferably selected from 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 C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy. More preferably, Rv2, Rw2, Rv3 and Rw3 are, independently of each other, selected from hydrogen and Ci-C2-alkyl. Especially, Rv2, Rw2, Rv3 and Rw3 are, independently of each other, hydrogen or methyl. Likewise, in this preferred group, preference is given to those compounds of formulae (I) an (la), where on the radicals Rv2, Rw2, Rv3 and Rw3 is in particular 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 C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, while the other radicals Rv2, Rw2, Rv3 and Rw3 are hydrogen. Especially, Rv2, Rv3, Rw2 and Rw3 are each hydrogen. In this group of embodiments, W is preferably S or NRw1, wherein Rw1 is as defined above and has in particular one of the preferred meanings, especially hydrogen or Ci-C2-alkyl such as methyl. A further preferred group of embodiments relates to compounds of formulae (I) and (la), wherein W2-W3-W4 is a bivalent radical -C(Rv4)=C(Rv5)-, in which C(Rv4) is bound to W1 and where Rv4 and Rv5 are independently from each other preferably selected from hydrogen, halogen such as fluorine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C4- alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy. Preferably, at most one of Rv4 and Rv5 is different from hydrogen. Especially, Rv4 and Rv5 are both hydrogen. In this particular group of embodiments, W is in particular S or NRw1, wherein Rw1 has one of the meanings given above, especially a preferred meaning, in particular hydrogen or methyl, especially hydrogen. In this particular group of embodiments, likewise W is in particular N-CH3. In this particular group of embodiments, likewise W is in particular O.
A further preferred preferred group of embodiments relates to compounds of formulae (I) and (la), wherein W2-W3-W4 is a bivalent radical -C(Rv4)=C(Rv5)-, in which C(Rv4) is bound to W1 and where one of Rv4 and Rv5 is hydrogen while the other is 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 fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy. In this particular group of embodiments, W is O, S or NRw1, wherein Rw1 has one of the meanings given above, especially a preferred meaning, in particular hydrogen or methyl. Especially, W is S.
A further preferred preferred group of embodiments relates to compounds of formulae (I) and (la), wherein W2-W3-W4 is a bivalent radical -C(Rv4)=C(Rv5)-, in which C(Rv4) is bound to W1 and where Rv4 and Rv5 are both different from hydrogen. Preferably, Rv4 and Rv5 are
independently from each other selected from halogen such as fluorine or chlorine, CN, C1-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, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy. Especially, Rv4 and Rv5 are both selected from Ci-C4-alkyl. In this particular group of embodiments, W is O, S or NRw1, wherein Rw1 has one of the meanings given above, especially a preferred meaning. Especially, W is S.
A further preferred preferred group of embodiments relates to compounds of formulae (I) and (la), wherein W2-W3-W4 is a bivalent radical -C(Rv4)=C(Rv5)-, in which C(Rv4) is bound to W1 and where Rv4 and Rv5 may together be a C2-C4-alkylene chain forming a 4-, 5- or 6-memberd unsaturated ring together with the carbon atoms Rv4 and Rv5 are bonded to. Especially, Rv4 and Rv5 together form -CH2-CH2-CH2-. In this particular group of embodiments, W1 is O, S or NRw1, wherein Rw1 has one of the meanings given above, especially a preferred meaning. Especially, W is S.
A further particular group of embodiments relates to compounds of formulae (I) and (la), wherein W2-W3-W4 is C(Rv2Rw2)-0-C(Rv3Rw3)-, wherein C(Rv2Rw2)- is bound to W1 and where Rv2, Rw2, Rv3 and Rw3 independently of each other, are preferably selected from the group consisting of hydrogen, CN, hydrogen, CN, Ci-C4-alkyl, in particular Ci-C2-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-alkyl, such as Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, in particular Ci-C2-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-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy. Preferably, at most one of where Rw2, Rv3 and Rw3 are different from hydrogen. In this particular group of embodiments, preference is given to those compounds of formulae (I) and (la), where one of the radicals Rv2, Rv3, Rw2 and Rw3 is 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-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, while the other radicals Rv2, Rv3, Rw2 and Rw3 are hydrogen. In particular Rv2, Rv3, Rw2 and Rw3 are all hydrogen. In this particular group of embodiments, W is preferably NRw1, where Rw1 is as defined above and, preferably has one of the preferred meanings. Especially, Rw1 is hydrogen or Ci-C4-alkyl, more preferably hydrogen or methyl.
Preferred are compounds of formulae (I) and (la), wherein the moiety of the formula (W.Het)
Figure imgf000057_0001
represents a radical selected from the group consisting of W.Het-1 , W.Het-2, W.Het-2a, W.Het- 3, W.Het-4, and W.Het-5 and W.Het-6
Figure imgf000057_0002
(W.Het-1 ) (W.Het-2) (W.Het-2a)
Figure imgf000057_0003
(W.Het-3) (W.Het-4) (W.Het-5) (W.Het-6) wherein # denotes the bond to the remainder of the molecule and where X1, R1, R2 and Het are as defined herein and where R1, R2 and Het, individually or in combination have the meanings given as preferred meanings, and wherein Rw1, if present, is as defined above and in particular 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, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C4-alkoxy-Ci-C4-alkyl, in particular Ci-C2-alkoxy-Ci-C2-alkyl, such as methoxymethyl, ethoxymethyl, methoxyethyl or ethoxyethyl, Ci-C4-alkylcarbonyl, in particular C1-C2- alkylcarbonyl such as methylcarbonyl or ethylcarbonyl, and Ci-C4-haloalkylcarbonyl, in particular Ci-C2-haloalkylcarbonyl. More preferably, Rw1 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-alkylcarbonyl. Especially, Rw1 is hydrogen, methyl or methylcarbonyl (acetyl), in particular hydrogen or methyl. In the radical W.Het-2a, at least one of the radicals Rv4 and Rv5 is different from hydrogen and Rv4 and Rv5 have the meanings given above, preferably the meanings given as preferred and in particular are independently from each other selected from the group consisting of hydrogen, halogen such as chlorine, Ci-C4-alkyl such as methyl, ethyl, n-propyl and isopropyl, and 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, wherein at least one of the radicals Rv4 and Rv5 is different from hydrogen or Rv4 and Rv5 may together be a C2-C4 alkylene chain forming a 4- to 6-membered unsaturated ring together with the carbon atoms atom Rv4 and Rv5 are bonded to.
Particularly preferred are compounds of formulae (I) and (la), wherein the moiety of the formula (W.Het) is selected from the group consisting of W.Het-1 and W.Het-2. Likewise, particularly preferred are compounds of formulae (I) and (la), wherein the moiety of the formula (W.Het) is a radical W.Het-2a, wherein Rv4 and Rv5 are as defined and in particular are independently from each other selected from the group consisting of hydrogen, halogen such as chlorine, Ci-C4-alkyl such as methyl, ethyl, n-propyl and isopropyl, and 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, wherein at least one of the radicals Rv4 or Rv5 is different from hydrogen or Rv4 and Rv5 may together be a C2-C4 alkylene chain forming a 4- to 6-membered unsaturated ring together with the carbon atoms atom Rv4 and Rv5 are bonded to. Likewise, particularly preferred are compounds of formulae (I) and (la), wherein the moiety of the formula (W.Het) is selected from the group consisting of W.Het-3, and W.Het-4, wherein Rw1 is as defined and in particular has one of the preferred menaings. In particular Rw1 is hydrogen. Likewise, particularly preferred are compounds of formulae (I) and (la), wherein the moiety of the formula (W.Het) is a radical W.Het-6.
In the moieties W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, the heterocycle Het is in particular selected from the group consisting of the radicals of formulae Het-1 to Het-24, as defined above, and in particular selected from the group consisting of the radicals of the formulae Het-1 or Het-1 a, Het-1 1 a and Het-24.
In the moieties W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, the radicals R1 and R2 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 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6- halocycloalkyl such as 1 -fluorocyclopropyl or 2,2-difluorocyclopropyl, or R1 and R2 may together be =CR13R14 or R1 and R2 form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl.
In particular embodiments of moieties W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4,
W.Het-5 and W.Het-6, the radicals R1 and R2 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 R1 and R2 is hydrogen.
Especially, R1 and R2 in the moieties W.Het-1 , W.Het-2a, W.Het-2, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, are both hydrogen.
A particular group 1 of embodiments relates to compounds of the formulae (I) and (la), 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.
A further particular group 2 of embodiments relates to compounds of the formulae (I) and (la), 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.
A further particular group 3 of embodiments relates to compounds of the formulae (I) and (la), 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.
A further particular group 4 of embodiments relates to compounds of the formulae (I) and
(la), 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.
A further particular group 5 of embodiments relates to compounds of the formulae (I) and (la), 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 selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24.
A further particular group 6 of embodiments relates to compounds of the formulae (I) and (la), 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 and Het-24. A further particular group 7 of embodiments relates to compounds of the formulae (I) and (la), 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 and Het-24.
A special group 1 a of embodiments relates to compounds of the formulae (I) and (la), 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 2a of embodiments relates to compounds of the formulae (I) and (la), 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 a radicals of formulae Het-1 a.
A further special group 3a of embodiments relates to compounds of the formulae (I) and (la), 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 a radicals of formulae Het-1 a.
A further special group 4a of embodiments relates to compounds of the formulae (I) and (la), 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 radicals of formulae Het-1 a.
A further special group 5a of embodiments relates to compounds of the formulae (I) and (la), 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 radicals of formulae Het-1 a.
A further special group 6a of embodiments relates to compounds of the formulae (I) and
(la), 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 radicals of formulae Het-1 a.
A further special group 7a of embodiments relates to compounds of the formulae (I) and (la), 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 radicals of formulae Het-1 a.
In embodiments 3, 3a, 4 and 4a the radical Rw1 is as defined above and in particular 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, 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-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy. In embodiments 3, 3a, 4 and 4a the radical Rw1 is especially hydrogen. Likewise, in embodiments 3, 3a, 4 and 4a the radical Rw1 is especially methyl.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7,1 a, 2a, 3a, 4a, 5a, 6a and 7a, the variables m, R1 , R2, R3, R4a, R4b and R5 are as defined above and in particular have the preferred meanings.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7,1 a, 2a, 3a, 4a, 5a, 6a and 7a, the variables m, R1 , R2, R3, R4a, R4b and R5, independently of each other or in particular in combination, in particular have the following meanings:
m is 0 or 1 ;
R1 and R2 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 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, or R1 and R2 may together be =CR13R14 or R1 and R2 form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl;
R3 is selected from the group consisting of hydrogen, halogen, CN , Ci-C6-alkyl, in
particular Ci-C4-alkyl, Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, C3-C6-halocycloalkyl, such as 1 -fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2-chlorocyclopropyl, 2,2- dichlorocyclopropyl, 1 -fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 2,2- difluorocyclobutyl or 3,3-difluorocyclobutyl, NR9aR9b and NR9a-C(=0)R7a, where R7a, R9a and R9b are as defined above and in particular have the preferred meanings; R5 is selected from the group consisting of hydrogen, halogen, NR9aR9b, Ci-C6-alkyl, in particular Ci-C4-alkyl, Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, S-Ci-C6-alkyl, in particular S-Ci-C4-alkyl, S-Ci-C6-haloalkyl, in particular S-Ci-C4-haloalkyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, S-C3-C6-cycloalkyl, S-C3-C6-halocycloalkyl, C(=0)OR8, C(=0)NR aR , C(=S)NR aR , C(=0)R7a, C(=S)R7a, Q-phenyl, where phenyl is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or Q-Het#, where Het# is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
and where Q, irrespectively of its occurrence, is a single bond, S, NR9a, such as NH or N(CH3), -NR a-C(=0)-, such as -NH(C=0)-, -NR a-C(=0)R7a-, such as NH- C(=0)H, NH-C(=0)CH3, NH-C(=0)CH2CH3 or NH-C(=0)CH(CH3)2,
OC(=0)-, -NR aCH2-, such as NHCH2 or N(CH3)CH2, -OC(=0)CH2-,
or -NR aC(=0)CH2- such as -NHC(=0)CH2-,
where R7a, R9a, R9b and R10 are as defined above and in particular have the preferred meanings;
and if m =1
R4a and R4b are selected, independently from one another, from the group consisting of hydrogen, Ci-C4-alkyl, in particular methyl, and halogen, in particular fluorine or chlorine, or R4a and R4b together are =0.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4 W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a , the variables m, R1, R2, R3, R4a, R4b and R5, independently of each other or in particular in combination, more particularly have the following meanings:
m is 0 or 1 ;
R1 and R2 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 R1 and R2 is hydrogen and where especially both R1 and R2 are hydrogen;
R3 is selected from the group consisting of hydrogen, fluorine, chlorine, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl or n-butyl, NH-C(=0)H, NHC(=0)-Ci-C4- alkyl, such as
NH-C(=0)CH3, NH-C(=0)CH2CH3 or NH-C(=0)CH(CH3)2, and CN, and in particular selected from the group of hydrogen and Ci-C4-alkyl, such as methyl, ethyl, n- propyl, isopropyl or n-butyl;
R5 is selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, S-d-Ce-alkyl, in particular S-Ci-C4-alkyl, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, 2-butylthio or isobutylthio, S-Ci-C6-haloalkyl, in particular S-Ci-C4-haloalkyl, such as
fluoromethylthio, difluoromethylthio, trifluoromethylthio, 1 ,1 -difluoroethylthio, 2- fluoroethylthio, 2,2-difluoroethylthio or 2,2,2-trifluoroethylthio, C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, C3-C6-halocycloalkyl, such as 1 -fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 1 -fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 2,2-difluorocyclobutyl or 3,3-difluorocyclobutyl, C3-C6-cycloalkylthio, such as cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio, C3-C6- halocycloalkylthio, such as 1 -fluorocyclopropylthio, 2-fluorocyclopropylthio, 2,2- difluorocyclopropylthio, 2-chlorocyclopropylthio, 2,2-dichlorocyclopropylthio, 1 - fluorocyclobutylthio, 2-fluorocyclobutylthio, 3-fluorocyclobutylthio, 2,2- difluorocyclobutylthio or 3,3-difluorocyclobutylthio, phenyland S-phenyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different substituents R10, where R10 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci- C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2- trifluoroethoxy;
and if m =1
R4a and R4b are selected, independently from one another, from the group consisting of hydrogen and methyl, in particular hydrogen or R4a and R4b together are =0. In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a, the variables R1, R2, R3, and R5, independently of each other or in particular in combination, especially may also have the following meanings:
m is 0 or 1 ;
both R1 and R2 are hydrogen; R3 is selected from the group consisting of hydrogen, fluorine, chlorine, Ci-C4-alkyl,
NHC(=0)-Ci-C4-alkyl and CN;
R5 is hydrogen, halogen, d-Ce-alkyl, d-Ce-haloalkyl, S-d-Ce-alkyl, S-d-Ce-haloalkyl, d-d- cycloalkyl, d-d-halocycloalkyl, S-d-d-cycloalkyl, S-d-d-halocycloalkyl, phenyl and and S-phenyl, where the phenyl ring in the last to radicals is unsubstituted or carries 1 , 2,
3, 4 or 5 identical or different substituents R10;
if m is 1 ,
R4a, R4b are each hydrogen, or
if m is 0,
R3 and R5 together with the carbon atom, to which they are bound, form a 3- or 4-membered saturated carbocycle, wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3,
4, 5 or 6 radicals R7b, or
R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated heterocycle having 1 or 2 non adjacent heteroatoms as ring members which are selected from O and S, wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, where
R7b is selected from the group consisting of halogen, d-d-alkyl, and wherein one
radical R7b may also be
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, where
R10 is selected from the group consisting of halogen, CN, d-d-alkyl, Ci-C4- haloalkyl, d-d-alkoxy and d-d-haloalkoxy.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a , where m = 0, the variables R1, R2, R3, and R5, independently of each other or in particular in combination, in particular may also have the following meanings:
R1 and R2 are, independently from each other, selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-d-alkyl, in particular Ci-d-alkyl, such as methyl, ethyl, n-propyl or isopropyl, d-d-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-d-haloalkyl, in particular d-d-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or d-d-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl, or R1 and R2 may together be =CR13R14 or R1 and R2 form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl; R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated carbocycle, wherein each of the carbon atoms of the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, wherein R7b is as defined above and wherein
R7b is in particular selected from the group consisting of
halogen, Ci-C6-alkyl, Ci-C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by a radical selected from Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, phenoxy, 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, and
wherein one or two radicals R7b may also be
Cs-Cs-cycloalkyI, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from halogen, Ci-C4-alkyl and Ci-C4-alkoxycarbonyl , in particular selected from fluorine, chlorine, and methyl,
C3-C6-cycloalkenyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl,
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or
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, such as tetrahydrofuryl, tetrahydropyranyl, tetrahydrothiopyranyl or thiazolyl, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, in particular a 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N, where the 5- or 6-membered hetaryl is unsubstituted or carries 1 , 2 or 3 identical or different substituents R10, or two of R7b present on one ring carbon may together form =0 or =S,
or two R7b together form a linear C2-C7-alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
R10 has one of the meanings given above and where R10 is in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy,
R7b is more particularly selected from the group consisting of halogen, Ci-C6-alkyl, Ci-
C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated, and wherein one or two radicals R7b may also be
C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or a
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, in particular a 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N, where the 5- or 6-membered hetaryl is unsubstituted or carries 1 , 2 or 3 identical or different substituents R10, or two of R7b present on one ring carbon may together form =0 or =S,
or two R7b together form a linear C2-C7-alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
R10 has one of the meanings given above and is in particular selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7,1 a, 2a, 3a, 4a, 5a, 6a and 7a , where m = 0, the variables R1, R2, R3, and R5, independently of each other or in particular in combination, more particular may also have the following meanings:
R1 and R2 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 R1 and R2 is hydrogen and where especially both R1 and R2 are hydrogen;
R3 and R5 together with the carbon atom, to which they are bound, form a 3- or 4-membered saturated carbocycle, i.e. a 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical, wherein each of the carbon atoms of the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, wherein
R7b is as defined above and in particular selected from the group consisting of
halogen, Ci-C6-alkyl, Ci-C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by a radical selected from Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, phenoxy, 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, and wherein one or two radicals R7b may also be
C3-C8-cycloalkyl, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from halogen, Ci-C4-alkyl and Ci-C4-alkoxycarbonyl, in particular selected from fluorine, chlorine and, methyl as,
C3-C6-cycloalkenyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl,
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or
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, such as tetrahydrofuryl, tetrahydropyranyl, tetrahydrothiopyranyl or thiazolyl, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, in particular a 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N, where the 5- or 6-membered hetaryl is unsubstituted or carries 1 , 2 or 3 identical or different substituents R10, or two of R7b present on one ring carbon may together form =0 or =S,
or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
R10 has one of the meanings give above and where R10 is in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or
R7b is especially selected from the group consisting of particular selected from the group consisting of halogen, Ci-C4-alkyl, and wherein one radical R7b may also be phenyl, optionally substituted with 1 , 2, 3, 4 or 5, in particular 1 , 2 or 3, identical or different substituents R10, where
R10 is as defined above, and in particular selected from the group consisting of halogen, such as fluorine or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a, where m = 0, the variables R1, R2, R3, and R5, independently of each other or in particular in combination, especially may also have the following meanings:
R1 and R2 are are hydrogen or one of R1 and R2 is hydrogen and the other of R1 and R2 is
methyl;
R3 and R5 together form the following moieties:
CH2-CH2, CHF-CH2, CF2-CH2, CHF-CHF, CF2-CHF, CF2-CF2, CHCI-CH2, CCI2-CH2,
CHCI-CHCI, CC -CHCI, CCI2-CCI2, CH(CH3)-CH2, C(CH3)2-CH2, CH(CH3)-CH(CH3),
C(CH3)2-CH(CH3), C(CH3)2-C(CH3)2, CH(OCH3)-CH2, CH(CH2CH3)-CH2, CH(CH2CH2CH3)-CH2, CH(CH2CH2CH2CH3)-CH2, CH(CH3)-CH2-CH2, CH2-CH(CH3)-CH2, C(CH3)2-CH2-CH2,
CH2-C(CH3)2-CH2, CH(CH3)-CH(CH3)-CH2, CH(CH3)-CH2-CH(CH3),
CH(CH3)-CH(CH3)-CH(CH3), C(CH3)2-CH(CH3)-CH2, CH(CH3)-C(CH3)2-CH2,
C(CH3)2-CH2-C(CH3)2, C(CH3)2-C(CH3)2-CH2, C(CH3)2-C(CH3)2-C(CH3)2, CHF-CH2-CH2,
CH2-CHF-CH2, CF2-CH2-CH2, CH2-CF2-CH2, CHF-CHF-CH2, CHF-CH2-CHF, CHF-CHF-CHF, CF2-CHF-CH2, CHF-CF2-CH2, CF2-CH2-CF2, CF2-CF2-CH2, CF2-CF2-CF2, CHCI-CH2-CH2, CH2-CHCI-CH2, CCI2-CH2-CH2, CH2-CCI2-CH2, CHCI-CHCI-CH2, CHCI-CH2-CHCI, CHCI-CHCI-CHCI, CCI2-CHCI-CH2, CHCI-CCI2-CH2, CCI2-CH2-CCI2, CCI2-CCI2-CH2,
Figure imgf000069_0001
a radical CH(R7bb)-CH2, where R7bb is selected from the group consisting of
C2-C6-alkyl, such as ethyl, n-propyl, isopropyl, n-butyl, tert.butyl, 1 -methylpropyl, 2- methylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3-dimethylpropyl, 1 - methylbutyl, 1 ,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl, ,
C2-C4-haloalkyl, such as 2,2-difluoroethyl, 1 , 1 -difluoroethyl or 2,2,2-trifluoroethyl, Ci-C6-alkyl, which is substituted by 1 radical selected from Ci-C4-alkoxy, C1-C4- alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Cs-Cs-cycloalkyl, C3- Cs-cycloalkoxy, phenoxy and 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothiopyranyl, where Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy and 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples of substituted Ci-C6-alkyl including 1 -methoxyethyl, 2-methoxyethyl, 1 -propoxyethyl, 2-propoxyethyl, 1 - isopropoxyethyl, 2-isopropoxyethyl, 1 -isobutoxyethyl, 2-isobutoxyethyl, 1 - (cyclohexyloxy)ethyl, 2-phenoxyethyl, (4-isopropylcyclohexyl)methyl, 1 -acetoxyethyl,
2- acetoxyethyl, 6-acetoxyhexyl, 2-methylsulfanylpropyl, 1 -methyl-2- methylsulfanylethyl, tetrahydropyran-4-ylmethyl, tetrahydrothiopyran-4-ylmethyl,
C2-Cio-alkenyl, such as 3-nonenyl,
C3-Cio-cycloalkyl, optionally substituted by 1 or 2 Ci-C4-alkyl, in particular C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 4-methylcyclohexyl, 4-isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl, C5-C6-cycloalkenyl, optionally substituted by 1 or 2 Ci-C4-alkyl, such as 2- methylcyclohex-3-en-1 -yl,
5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6-membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tehtrahydrothiopyran-
3- yl, tetrahydrothiopyran-4-yl, 6-methoxy-3-methyltetrahydropyran-2-yl, and 5,5- dimethyltetrahydrofuran-2-yl,
optionally substituted phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl, 3- (trifluoromethyl)phenyl and 4-cyanophenyl,
5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy examples of hetaryl including 4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl, phenyl-Ci-C4-alkyl, such as benzyl or phenethyl, and
hetaryl-Ci-C4-alkyl, where the hetaryl is 5- or 6-membered and has 1 or 2
heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy examples of hetaryl-Ci-C4-alkyl including 1 ,1 -dimethyl-2-(3-pyridyl)ethyl,
thereby forming, together with the carbon atom they are bound to, an unsubstituted or substituted 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a , where m = 0, the variables R1, R2, R3, and R5, independently of each other or in particular in combination, especially may also have the following meanings:
R1 and R2 are hydrogen or one of R1 and R2 is hydrogen and the other of R1 and R2 is methyl;
R3 and R5 together form a moiety selected from the group consisting of:
CH2-CH2, CHF-CH2, CF2-CH2, CHF-CHF, CF2-CHF, CF2-CF2, CHCI-CH2, CCI2-CH2, CHCI-CHCI, CC -CHCI, CCI2-CCI2, CH(CH3)-CH2, C(CH3)2-CH2, CH(CH3)-CH(CH3), C(CH3)2-CH(CH3), C(CH3)2-C(CH3)2, CH(OCH3)-CH2, CH(CH2CH3)-CH2,
CH(CH2CH2CH3)-CH2, CH(CH2CH2CH2CH3)-CH2, CH(CH3)-CH2-CH2, CH2-CH(CH3)-CH2, C(CH3)2-CH2-CH2, CH2-C(CH3)2-CH2, CH(CH3)-CH(CH3)-CH2, CH(CH3)-CH2-CH(CH3), CH(CH3)-CH(CH3)-CH(CH3), C(CH3)2-CH(CH3)-CH2, CH(CH3)-C(CH3)2-CH2,
C(CH3)2-CH2-C(CH3)2, C(CH3)2-C(CH3)2-CH2, C(CH3)2-C(CH3)2-C(CH3)2, CHF-CH2-CH2, CH2-CHF-CH2, CF2-CH2-CH2, CH2-CF2-CH2, CHF-CHF-CH2, CHF-CH2-CHF,
CHF-CHF-CHF, CF2-CHF-CH2, CHF-CF2-CH2, CF2-CH2-CF2, CF2-CF2-CH2, CF2-CF2-CF2, CHCI-CH2-CH2, CH2-CHCI-CH2, CCI2-CH2-CH2, CH2-CCI2-CH2, CHCI-CHCI-CH2,
CHCI-CH2-CHCI, CHCI-CHCI-CHCI, CCI2-CHCI-CH2, CHCI-CCI2-CH2, CCI2-CH2-CCI2, CCI2-CCI2-CH2, CCI2-CCI2-CCI2 or a radical CH(Ar)-CH2, where Ar is selected from phenyl, 2-chlorophenyl, 2-fluorophenyl, 2-methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3- chlorophenyl, 3-fluorophenyl, 3-methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4- chlorophenyl, 4-fluorophenyl, 4-methylphenyl, 4-methoxyphenyl and 4-cyanophenyl, thereby forming, together with the carbon atom they are bound to, an unsubstituted or substituted 1 ,1 -cyclopropylidene or 1 ,1 -cyclobutylidene radical.
Speciall preference is given to compounds of formula (la),
Figure imgf000071_0001
where Het, W, W2, W3, W4, X1 and X2, are as defined above and in particular have the preferred meanings or the particularly preferred meanings;
R1 and R2 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 R1 and R2 is hydrogen and where especially both R1 and R2 are hydrogen;
R7b1 is hydrogen or has one of the meanings given for R7b;
R7b2, R7b3 and R7b4 are hydrogen, methyl or halogen, in particular hydrogen and where
R7b1 is in particular hydrogen or a radical selected from the group consisting of
Ci-C6-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert. butyl, 1 - methylpropyl, 2-methylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3- dimethylpropyl, 1 -methylbutyl, 1 ,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 1 ,1 - difluoroethyl or 2,2,2-trifluoroethyl,
Ci-C6-alkyl, which is substituted by 1 radical selected from Ci-C4-alkoxy, C1-C4- alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Cs-Cs-cycloalkyl, C3- Cs-cycloalkoxy, phenoxy and 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothiopyranyl, where Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy and 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples of substituted Ci-C6-alkyl including 1 -methoxyethyl, 2-methoxyethyl, 1 -propoxyethyl, 2-propoxyethyl, 1 - isopropoxyethyl, 2-isopropoxyethyl, 1 -isobutoxyethyl, 2-isobutoxyethyl, 1 - (cyclohexyloxy)ethyl, 2-phenoxyethyl, (4-isopropylcyclohexyl)methyl, 1 -acetoxyethyl, 2-acetoxyethyl, 6-acetoxyhexyl, 2-methylsulfanylpropyl, 1 -methyl-2- methylsulfanylethyl, tetrahydropyran-4-ylmethyl, tetrahydrothiopyran-4-ylmethyl, C2-Cio-alkenyl, such as 3-nonenyl,
C2-C6-alkynyl,
C3-Cio-cycloalkyl, optionally substituted by 1 or 2 Ci-C4-alkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 4-methylcyclohexyl, 4- isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
C5-C6-cycloalkenyl, optionally substituted by 1 or 2 Ci-C4-alkyl, such as 2- methylcyclohex-3-en-1 -yl,
5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6-membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tehtrahydrothiopyran- 3-yl, tetrahydrothiopyran-4-yl, 6-methoxy-3-methyltetrahydropyran-2-yl, and 5,5- dimethyltetrahydrofuran-2-yl,
optionally substituted phenyl such as phenyl, 2-chlorophenyl, 2-fluorophenyl, 2- methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl, 3- methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4- methylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl, 3- (trifluoromethyl)phenyl and 4-cyanophenyl,
5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy examples of hetaryl including 4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl, phenyl-Ci-C4-alkyl, such as benzyl or phenethyl, and
hetaryl-Ci-C4-alkyl, where the hetaryl is 5- or 6-membered and has 1 or 2
heteroatoms as ring memberes, selected from O, S and N and where the hetaryl is unsubsituted or substuted by 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy examples of hetaryl-Ci-C4-alkyl including 1 ,1 -dimethyl-2-(3-pyridyl)ethyl.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a, where m = 0, the variables R1, R2, R3, and R5, independently of each other or in particular in combination, in particular may also have the following meanings:
R1 and R2 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, or R1 and R2 may together be =CR13R14 or R1 and R2 form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl; R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated heterocycle having 1 or 2 non adjacent heteroatoms as ring members which are selected from O and S, in particular a 3 or 4 membered saturated heterocycle having 1 oxygen atom as ring member wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, wherein R7b, if present, is as defined above and wherein
R7b if present, is in particular selected from the group consisting of
halogen, Ci-C6-alkyl, Ci-C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by a radical selected from Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, phenoxy, 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, and wherein one or two radicals R7b may also be
Cs-Cs-cycloalkyI, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine, Ci-C4-alkyl such as methyl and Ci- C4-alkoxycarbonyl such as methoxycarbonyl,
C3-C6-cycloalkenyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl,
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 0 , or
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, such as tetrahydrofuryl, tetrahydropyranyl, tetrahydrothiopyranyl or thiazolyl, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, in particular a 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N, where the 5- or 6-membered hetaryl is unsubstituted or carries 1 , 2 or 3 identical or different substituents R10, or two of R7b present on one ring carbon may together form =0 or =S, or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
R10 has one of the meanings give for R10 and where R10b is in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy,
is more particularly selected from the group consisting of halogen, Ci-C6-alkyl, Ci- C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated, and wherein one or two radicals R7b may also be
C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or a
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, in particular a 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N, where the 5- or 6-membered hetaryl is unsubstituted or carries 1 , 2 or 3 identical or different substituents R10a, or two of R7b present on one ring carbon may together form =0 or =S,
or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where R10 has one of the meanings given above and where R10 is in particular selected from the group consisting of halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a, where m = 0, the variables R1, R2, R3, and R5, independently of each other or in particular in combination, more particular may also have the following meanings:
R1 and R2 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 R1 and R2 is hydrogen and where especially both R1 and R2 are hydrogen;
R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated heterocycle having 1 or 2 non adjacent heteroatoms as ring members which are selected from O and S, in particular a 3- or 4-membered saturated heterocycle having 1 oxygen atom as ring member wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, wherein R7b, if present, is as defined above and wherein
R7b is as defined above and in particular selected from the group consisting of
halogen, Ci-C6-alkyl, Ci-C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by a radical selected from Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, phenoxy, 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or 6- membered saturated heterocyclyl may be unsubstituted or carry 1 or 2 radicals selected from Ci-C4-alkyl and Ci-C4-alkoxy, and wherein one or two radicals R7b may also be
C3-Ce-cycloalkyl, in particular C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine, Ci-C4-alkyl such as methyl and Ci- C4-alkoxycarbonyl such as methoxycarbonyl, in particular selected from fluorine, chlorine and methyl,
C3-C6-cycloalkenyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or Ci-C4-alkyl such as methyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or
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, such as tetrahydrofuryl, tetrahydropyranyl, tetrahydrothiopyranyl or thiazolyl, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, in particular a 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N, where the 5- or 6-membered hetaryl is unsubstituted or carries 1 , 2 or 3 identical or different substituents R10, or two of R7b present on one ring carbon may together form =0 or =S,
or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, where
R10 has one of the meanings give for R10 and where R10b is in particular selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or
R7b is especially selected from the group consisting of particular selected from the group consisting of halogen, Ci-C4-alkyl, and wherein one radical R7b may also be phenyl, optionally substituted with 1 , 2, 3, 4 or 5, in particular 1 , 2 or 3, identical or different substituents R10, where
R10 is as defined above, and in particular selected from the group consisting of halogen, such as fluorine or chlorine, Ci-C4-alkyl, CN, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
In the compounds of formula (I), where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a , where m = 0, the variables R1, R2, R3, and R5, independently of each other or in particular in combination, especially may also have the following meanings:
R1 and R2 are hydrogen or one of R1 and R2 is hydrogen and the other of R1 and R2 is methyl; R3 and R5 together form 0-CH2 or O-CH2-CH2, where 1 , 2, 3 or 4 of the hydrogen atoms of CH2 and CH2-CH2, respectively, may be replaced by a radical R7b, thereby forming, together with the carbon atom they are bound to, an unsubstituted or substituted 1 ,1 -cyclopropylidene or 1 ,1 - cyclobutylidene radical.
In the compounds of formulae (I) and (la), in particular in those compounds of formula (I) where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het- 2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a, the variable X1 is in particular O.
In the compounds of formulae (I) and (la), in particular in those compounds of formula (I) where the moiety of formula (W.Het) is selected from the moieties of formulae W.Het-1 , W.Het- 2, W.Het-2a, W.Het-3, W.Het-4, W.Het-5 and W.Het-6, and likewise in the embodiments 1 , 2, 3, 4, 5, 6, 7, 1 a, 2a, 3a, 4a, 5a, 6a and 7a, the variable X2 is in particular CN.
Apart from that, the variables Het#, Q, R6, R7, R7a, R8, R8a, R9a, R9b, R10, R10a, R11, R12, R13, R14, R15, R16, R17, R17a, R17b and R17c, irrespectively of their occurrence, in particular have the following meanings, if not stated otherwise:
Het# irrespectively of its occurrence, is 5- or 6-membered hetaryl such as pyridyl, thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxazolyl or isoxazolyl, which is unsubstituted or substituted by 1 , 2 or 3 radicals R10.
Q is, irrespectively of its occurrence, selected from a single bond, S, NR9a, CH2, and NR9aCH2, and it is in particular a single bond, S, NH, N(Ci-C4-alkyl), CH2, NHCH2or N(Ci- C4-alkyl)CH2.
R6 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 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.
R7 irrespectively of its occurrence, is selected from the group consisting of CN, C1-C4- alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or
trifluormethoxy, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or 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-trifluoroethyl or pentafluoroethyl, C3- C6-cycloalkyl such as cyclopropyl, cyclobutyl or cyclopropyl, and C3-C6-halocycloalkyl.
R7a 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, 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 C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
R8 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 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, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy.
R8a 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 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, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy.
R9a and R9b irrespectively of their occurrence, 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 NR9aR9b 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-C4-alkyl and Ci-C4-haloalkyl. Examples of such radicals NR9aR9b 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.
R10 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci- C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy. R10a irrespectively of its occurrence, is selected from the group consisting of halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, 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, C1-C6- alkoxy and Ci-C6-haloalkoxy.
R11, R12 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.
R13, R14 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.
R15 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, 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 C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
R16 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 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, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy.
R17 irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyl, C3-C6- cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n- propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
R17a and R17b irrespectively of their occurrence, 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 NR9aR9b 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-C4-alkyl and Ci-C4-haloalkyl. Examples of such radicals NR9aR9b 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.
R17c irrespectively of its occurrence, 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, 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 fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy.
Examples of preferred embodiments of the invention are compounds of the formulae 1.1 to
1.38, the tautomers, stereoisomers and salts thereof, in which Het, X2, R3, [CR4aR4b]m and R5 have one of the general or preferred meanings. In particular, preferred compounds are the individual compounds compiled in the tables 1 to 304 below. Moreover, the meanings mentioned below for the individual variables in the tables per se, independently of the combination in which they are mentioned, are a particularly preferred embodiment of the substituents in questions.
Table 1
Compounds of the formula 1.1 , their tautomers, their stereoisomers and their salts, in which Het is 6-chloro-3-pyridyl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 2
Compounds of the formula 1.1 , their tautomers, their stereoisomers and their salts, in which Het is 6-trifluoromethyl-3-pyridyl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 3
Compounds of the formula 1.1 , their tautomers, their stereoisomers and their salts, in which Het is 2-chlorothiazol-5-yl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 4
Compounds of the formula 1.1 , their tautomers, their stereoisomers and their salts, in which Het is 3-tetrahydrofuryl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 5 to 8
Compounds of the formula 1.1 , their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 9
Compounds of the formula 1.2, their tautomers, their stereoisomers and their salts, in which Het is 6-chloro-3-pyridyl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 10
Compounds of the formula 1.2, their tautomers, their stereoisomers and their salts, in which Het is 6-trifluoromethyl-3-pyridyl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 1 1
Compounds of the formula 1.2, their tautomers, their stereoisomers and their salts, in which Het is 2-chlorothiazol-5-yl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 12
Compounds of the formula 1.2, their tautomers, their stereoisomers and their salts, in which Het is 3-tetrahydrofuryl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 13 to 16
Compounds of the formula 1.2, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 17
Compounds of the formula 1.3, their tautomers, their stereoisomers and their salts, in which Het is 6-chloro-3-pyridyl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 18
Compounds of the formula 1.3, their tautomers, their stereoisomers and their salts, in which Het is 6-trifluoromethyl-3-pyridyl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 19
Compounds of the formula 1.3, their tautomers, their stereoisomers and their salts, in which Het is 2-chlorothiazol-5-yl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 20
Compounds of the formula 1.3, their tautomers, their stereoisomers and their salts, in which Het is 3-tetrahydrofuryl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 21 to 24
Compounds of the formula 1.3, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 25
Compounds of the formula 1.4, their tautomers, their stereoisomers and their salts, in which Het is 6-chloro-3-pyridyl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 26
Compounds of the formula 1.4, their tautomers, their stereoisomers and their salts, in which Het is 6-trifluoromethyl-3-pyridyl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 27
Compounds of the formula 1.4, their tautomers, their stereoisomers and their salts, in which Het is 2-chlorothiazol-5-yl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Table 28
Compounds of the formula 1.4, their tautomers, their stereoisomers and their salts, in which Het is 3-tetrahydrofuryl, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 29 to 32
Compounds of the formula 1.4, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 33 to 36
Compounds of the formula 1.5, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 37 to 40
Compounds of the formula 1.5, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 41 to 44
Compounds of the formula 1.6, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 45 to 48
Compounds of the formula 1.6, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 49 to 52 Compounds of the formula 1.7, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 53 to 56
Compounds of the formula 1.7, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 57 to 60
Compounds of the formula 1.8, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 61 to 64
Compounds of the formula 1.8, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 65 to 68
Compounds of the formula 1.9, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 69 to 72
Compounds of the formula 1.9, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 73 to 76
Compounds of the formula 1.10, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 77 to 80
Compounds of the formula 1.10, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 81 to 84
Compounds of the formula 1.1 1 , their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 85 to 88 Compounds of the formula 1.1 1 , their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 89 to 92
Compounds of the formula 1.12, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 93 to 96
Compounds of the formula 1.12, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 97 to 100
Compounds of the formula 1.13, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 101 to 104
Compounds of the formula 1.13, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 105 to 108
Compounds of the formula 1.14, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 109 to 1 12
Compounds of the formula 1.14, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 1 13 to 1 16
Compounds of the formula 1.15, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 1 17 to 120
Compounds of the formula 1.15, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 121 to 124 Compounds of the formula 1.16, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 125 to 128
Compounds of the formula 1.16, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 129 to 132
Compounds of the formula 1.17, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 133 to 136
Compounds of the formula 1.17, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 137 to 140
Compounds of the formula 1.18, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 141 to 144
Compounds of the formula 1.18, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 145 to 148
Compounds of the formula 1.19, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 149 to 152
Compounds of the formula 1.19, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 153 to 156
Compounds of the formula 1.20, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 157 to 160 Compounds of the formula 1.20, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 161 to 164
Compounds of the formula 1.21 , their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 165 to 168
Compounds of the formula 1.21 , their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 169 to 172
Compounds of the formula 1.22, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 173 to 176
Compounds of the formula 1.22, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 177 to 180
Compounds of the formula 1.23, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 181 to 184
Compounds of the formula 1.23, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 185 to 188
Compounds of the formula 1.24, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 189 to 192
Compounds of the formula 1.24, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 193 to 196 Compounds of the formula 1.25, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 197 to 200
Compounds of the formula 1.25, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 201 to 204
Compounds of the formula 1.26, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 205 to 208
Compounds of the formula 1.26, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 209 to 212
Compounds of the formula 1.27, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 213 to 216
Compounds of the formula 1.27, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 217 to 220
Compounds of the formula 1.28, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 221 to 224
Compounds of the formula 1.28, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 225 to 228
Compounds of the formula 1.29, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 229 to 232 Compounds of the formula 1.29, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 233 to 236
Compounds of the formula 1.30, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 237 to 240
Compounds of the formula 1.30, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 241 to 244
Compounds of the formula 1.31 , their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 245 to 248
Compounds of the formula 1.31 , their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 249 to 252
Compounds of the formula 1.32, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 253 to 256
Compounds of the formula 1.32, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 257 to 260
Compounds of the formula 1.33, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 261 to 264
Compounds of the formula 1.33, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 265 to 268 Compounds of the formula 1.34, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 269 to 272
Compounds of the formula 1.34, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 273 to 276
Compounds of the formula 1.35, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 277 to 280
Compounds of the formula 1.35, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 281 to 284
Compounds of the formula 1.36, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 285 to 288
Compounds of the formula 1.36, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 289 to 292
Compounds of the formula 1.37, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 293 to 296
Compounds of the formula 1.37, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 297 to 300
Compounds of the formula 1.38, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is cyano, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
Tables 301 to 304 Compounds of the formula 1.38, their tautomers, their stereoisomers and their salts, in which Het is as defined in tables 1 to 4, X2 is nitro, and m, R3, R4a, R4b and R5 for a compound corresponds in each case to one row of table A.
A skilled person will readily appreciate that the compounds of formulae 1.1 to 1.38, where R3, [CR4aR4b]m and R5 have the meanings given in one of the rows of the following table A may have S- or R-configuration with regard to the carbon atom carrying the radical R3 in case that m is zero, R3 is different from R5 and different from X2 and in case that m is 0, R3 is different from X2. The aforementioned embodiments include both the S-enantiomers and the R-enantiomers as well as mixtures of these enantiomers, in particular racemic mixtures.
Figure imgf000091_0001
(I. 10) (I. 1 1 ) (I. 12)
Figure imgf000092_0001
Figure imgf000093_0001
Figure imgf000094_0001
Figure imgf000095_0001
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Figure imgf000100_0001
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000104_0001
Figure imgf000105_0001
# R3 R5 [CR4aR4b]m
461 . CH(2-Me-c-C6H8)-CH2 -
462. CH(4-Me-c-C6Hio)-CH2 -
463. CH(5,5-DM-2-THF)-CH2 -
464. CH(CH2-4-THP)-CH2 -
465. CH(CH2CH2OCH2CH(CH3)2)-CH2 -
466. CH(CH(CH3)OCH2CH2OCH3)-CH2 -
467. CH(2-EC-c-C3H5)-CH2
468. CH(CH(CH3)OCH3)-CH2 -
469. CH(CH(CH3)CH(CH3)2)-CH2 -
470. CH(4-Me-5-TZ)-CH2 -
471 . CH(3-THP)-CH2 -
472. CH(CH2-4-THTP)-CH2 -
473. CH(CH(CH3)OC6H5)-CH2 -
474. CH(CH(CH3)0-c-C6Hii)-CH2 -
475. CH(4-lp-c-C6Hio)-CH2 -
476. CH(6-Ac-0-C6Hi2)-CH2 -
477. CH(3-CF3-C6H4)-CH2 -
478. CH(3-N02-C6H4)-CH2 -
479. CH(2-Py)-CH2 -
480. CH(4-CF3-C6H4)-CH2 -
481 . CH(CH3-0-C(0))-CH2 -
482. CH(Bz)-CH2 -
483. CH(CH2CF3)-CH2 -
484. CH(3-THF)-CH2 -
In table A, the following abbreviations are used:
In the last column "-" indicates that m = 0, i.e. [CR4aR4b] is absent.
c-C3H5: cyclopropyl
c-C4H7: cyclobutyl
c-C5H9: cyclopentyl
c-C6Hii: cyclohexyl
2-Me-c-C6H8: 2-methylcyclohexen-3-yl
4-Me-c-C6Hi0: 4-methylcyclohexyl
c-C7Hi3: cycloheptyl
c-C8Hi5: cyclooctyl
S-c-C3H5: cyclopropylsulfanyl
S-c-C4H7: cyclobutylsulfanyl
S-C-C5H9: cyclopentylsulfanyl
S-c-CeHu: cyclohexylsulfanyl 1 Q6
C6H5: phenyl
CH2-C6H5: benzyl
CH2CH2-C6H5: phenetyl
2-CI-C6H4: 2-chlorophenyl
2-F-C6H4: 2-fluorophenyl
2-Br-C6H4: 2-bromophenyl
4-CI-C6H4: 4-chlorophenyl
4-F-C6H4: 4-fluorophenyl
4-Br-C6H4: 4-bromophenyl
3-CI-C6H4: 3-chlorophenyl
3-F-C6H4: 3-fluorophenyl
3-Br-Cel-U: 3-bromophenyl
2-CH3-C6H4: 2-methylphenyl
3-CH3-C6H4: 3-methylphenyl
4-CH3-C6H4: 4-methylphenyl
2-CF3-C6H4: 2-trifluoromethylphenyl
3-CF3-CeH4: 3-trifluoromethylphenyl
4-CF3-C6H4: 4-trifluoromethylphenyl
2-CN-C6H4: 2-cyanophenyl
3-CN-C6H4: 3-cyanophenyl
4-CN-C6H4: 4-cyanophenyl
3-CF3-CeH4: 3-trifluoromethylphenyl
4-CF3-C6H4: 4-trifluoromethylphenyl
3-N02-C6H4: 3-nitrophenyl
2-OCH3-C6H4: 2-methoxyphenyl
3-OCH3-C6H4: 3-methoxyphenyl
4-OCH3-C6H4: 4-methoxyphenyl
3,4-CI2-C6H3: 3,4-dichlorophenyl
3,5-Cl2-CeH3: 3,5-dichlorophenyl
2,3-Cl2-CeH3: 2,3-dichlorophenyl
2,4-CI2-C6H3: 2,4-dichlorophenyl
2,5-Cl2-CeH3: 2,5-dichlorophenyl
2,6-CI2-C6H3: 2,6-dichlorophenyl
3,4-F2-C6H3: 3,4-difluorophenyl
3,5-F2-C6H3: 3,5-difluorophenyl
2,3-F2-CeH3: 2,3-difluorophenyl
2,4-F2-C6H3: 2,4-dichlorophenyl
2,5-F2-CeH3: 2,5-difluorophenyl
2,6-F2-C6H3: 2,6-difluorophenyl
3-CI-4-F-C6H3: 3-chloro-4-fluorophenyl
4-CI-3-F-C6H3: 4-chloro-3-fluorophenyl 7
3-Br-4-F-C6H3: 3-bromo-4-fluorophenyl
4-Br-3-F-C6H3: 4-bromo-3-fluorophenyl
3-Br-4-CI-C6H3: 3-bromo-4-chlorophenyl
4-Br-3-CI-C6H3: 4-bromo-3-chlorophenyl
3-OH-C6H4: 3-hydroxyphenyl
3,4,5-((OCH3)3C6H2): 3,4,5-trimethoxyphenyl
3,4-(CH30)2-C6H3: 3,4-dimethoxyphenyl
3-CH30-4-F-C6H3: 4-fluoro-3-methoxyphenyl
4-CH30-3-F-C6H3: 3-fluoro-4-methoxyphenyl
2-CI-5-N02-C6H3: 2-chloro-5-nitrophenyl
CH2CHCH2: allyl
CH2C(CH3)CH2: 2-methallyl
(CH3)2C=CHCH2: 3-methylbut-2-enyl
2-Py: 2-pyridyl
3-Py: 3-pyridyl
3-THF: tetra hyd rof ura n-3-yl
3-THP: tetra hyd ropy ra n-3-yl
4-THP: tetra hyd ropyra n-4-yl
CH2-4-THP: tetrahydropyran-4-yl-methyl
3-THTP: tetra hyd roth iopyra n-3-yl
4-THTP: tetra hyd roth iopyra n-4-yl
CH2-4-THTP: tetrahydrothiopyran-4-yl-methyl
4-Me-5-TZ: 4-methylthiazol-5-yl
6,6-DM-2-N: 6,6-dimethylnorpinan-2-yl
5,5-DM-2-THF: 5 , 5-d i methyltetrahyd rof ura n-2-yl
Bz: Benzyl
1 -AOE: 1 -acetoxyethyl
CH(CH3)OCH3: 1 -methoxyethyl
CH(CH3)OCH(CH3)2: 1 -isopropoxyethyl
CH(CH3)CH2SCH3: 1 -methyl-2-methylsulfanylethyl
CH2CH2OCH2CH2CH3: 2-propoxyethyl
CH2CH2OCH2CH(CH3)2 2-isobutoxyethyl
CH(CH3)OCH2CH2OCH 3: 1 -(2-methoxyethoxy)ethyl
CH(CH3)OC6H5: 1 -(phenoxy)ethyl
CH(CH3)0-c-C6Hii: 1 -(cyclohexyloxy)ethyl
2-EC-c-C3H5: 2-ethoxycarbonylcyclopropyl
CH(CH3)CH(CH3)2: 1 ,2-dimethylpropyl 4-lp-c-C6Hio: 4-isopropylcyclohexyl
6-AC-O-C6H12: 6-acetoxyhexyl
CH3-0-C(0): methoxycarbonyl
CH2CF3: 2,2,2-trifluoroethyl
The particularly preferred compounds amongst the compounds of formulae 1.1 to 1.38 mentioned above are those of the formulae 1.1 , 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.13, 1.14, 1.15 and 1.16, in particular 1.1 , I.3, 1.5, 1.7 and 1.15.
Particularly preferred compounds are compiled in the following tables B, C, D, E, F, G, H, J, K, L, M and N.
Table B
(I. 1 )
Figure imgf000109_0001
# Het X2 R3 R5 [C R4aR4b]m
B-1 6-chloro-2-pyridyl CN -CH2-CH2- -
B-2 2-chloro-5-thiazolyl CN -CH2-CH2- -
B-3 3-tetrahydrofuryl CN -CH2-CH2- -
B-4 6-chloro-2-pyridyl N02 H S-CFs -
B-5 2-chloro-5-thiazolyl N02 H S-CFs -
B-6 3-tetrahydrofuryl N02 H S-CFs -
Table C
Figure imgf000109_0002
# Het X2 R3 R5 [C R4aR4b]m
C-1 6-chloro-2-pyridyl CN -CH2-CH2- -
C-2 2-chloro-5-thiazolyl CN -CH2-CH2- -
C-3 3-tetrahydrofuryl CN -CH2-CH2- -
C-4 6-chloro-2-pyridyl N02 H S-CFs -
C-5 2-chloro-5-thiazolyl N02 H S-CFs -
C-6 3-tetrahydrofuryl N02 H S-CFs - Table D
Figure imgf000110_0001
# Het X2 R3 R5 [C R4aR4b]m
D-1 6-chloro-2-pyridyl CN -CH2-CH2- -
D-2 2-chloro-5-thiazolyl CN -CH2-CH2- -
D-3 3-tetrahydrofuryl CN -CH2-CH2- -
D-4 6-chloro-2-pyridyl N02 H S-CFs -
D-5 2-chloro-5-thiazolyl N02 H S-CFs -
D-6 3-tetrahydrofuryl N02 H S-CFs -
D-7 6-chloro-2-pyridyl CN H H -
D-8 2-chloro-5-thiazolyl CN H H -
D-9 3-tetrahydrofuryl CN H H -
D-10 6-chloro-2-pyridyl N02 H H -
D-1 1 2-chloro-5-thiazolyl N02 H H -
D-12 3-tetrahydrofuryl N02 H H -
Table E
S 2 R
I— I
# Het X2 R3 R5 [C R4aR4b]m
E-1 6-chloro-2-pyridyl CN -CH2-CH2- -
E-2 2-chloro-5-thiazolyl CN -CH2-CH2- -
E-3 3-tetrahydrofuryl CN -CH2-CH2- -
E-4 6-chloro-2-pyridyl N02 H S-CFs -
E-5 2-chloro-5-thiazolyl N02 H S-CFs -
E-6 3-tetrahydrofuryl N02 H S-CFs -
E-7 6-chloro-2-pyridyl CN H H -
E-8 2-chloro-5-thiazolyl CN H H -
E-9 3-tetrahydrofuryl CN H H -
D-10 6-chloro-2-pyridyl N02 H H # Het X2 R3 R5 [C R4aR4b]m
D-1 1 2-chloro-5-thiazolyl N02 H H
D-12 3-tetrahydrofuryl N02 H H
Table F
Figure imgf000111_0001
Figure imgf000111_0002
Table H
Figure imgf000112_0001
Figure imgf000112_0003
Table K
Figure imgf000112_0002
# Het X2 R3 R5 [C R4aR4b]m
K-1 6-chloro-2-pyridyl CN -CH2-CH2- -
K-2 2-chloro-5-thiazolyl CN -CH2-CH2- - # Het X2 R3 R5 [C R4aR4b]m
K-3 3-tetrahydrofuryl CN -CH2-CH2- -
K-4 6-chloro-2-pyridyl N02 H S-CFs -
Κ-5 2-chloro-5-thiazolyl N02 H S-CFs -
Κ-6 3-tetrahydrofuryl N02 H S-CFs -
Table L
Figure imgf000113_0001
Figure imgf000113_0003
Table M
Figure imgf000113_0002
Figure imgf000113_0004
Table N
Figure imgf000114_0001
Figure imgf000114_0003
In a specific embodiment, the compounds I are selected from the compounds specified in tables B, C, D, E, F, G, H, J, K, L, M, N and in the examples, either as a free base or a tautomer, or a stereoisomer, or a salt thereof.
The particularly preferred compounds amongst the compounds of formulae 1.1 to 1.38 mentioned above are also those of the formulae 1.17, 1.18, 1.19, I.20, I.27, I.28 I.35, I.36, 1.37 and 1.38, in particular 1.17, 1.19, I.27, 1.35 and 1.37.
Particularly preferred compounds are also compiled in the following tables O, P, Q, R, S, T, U, V, W and X
Table O
Figure imgf000114_0002
# Het X2 R3 R5 [C R4aR4b]m
0-1 6-chloro-2-pyridyl CN -CH2-CH2- -
0-2 2-chloro-5-thiazolyl CN -CH2-CH2- -
0-3 3-tetrahydrofuryl CN -CH2-CH2- -
0-4 6-chloro-2-pyridyl N02 H S-CFs -
0-5 2-chloro-5-thiazolyl N02 H S-CFs -
0-6 3-tetrahydrofuryl N02 H S-CFs - Table P
Figure imgf000115_0001
Figure imgf000115_0003
Table Q
Figure imgf000115_0002
Figure imgf000115_0004
Table R
Figure imgf000116_0001
Figure imgf000116_0004
Table S
Figure imgf000116_0002
Figure imgf000116_0005
Table T
Figure imgf000116_0003
# Het X2 R3 R5 [CR4aR4b]m # Het X2 R3 R5 [C R4aR4b]m
T-1 6-chloro-2-pyridyl CN -CH2-CH2- -
T-2 2-chloro-5-thiazolyl CN -CH2-CH2- -
Τ-3 3-tetrahydrofuryl CN -CH2-CH2- -
Τ-4 6-chloro-2-pyridyl N02 H S-CFs -
Τ-5 2-chloro-5-thiazolyl N02 H S-CFs -
Τ-6 3-tetrahydrofuryl N02 H S-CFs -
Table U
Figure imgf000117_0001
Figure imgf000117_0003
Table V
Figure imgf000117_0002
# Het X2 R3 R5 [C R4aR4b]m
V-1 6-chloro-2-pyridyl CN -CH2-CH2- -
V-2 2-chloro-5-thiazolyl CN -CH2-CH2- -
V-3 3-tetrahydrofuryl CN -CH2-CH2- -
V-4 6-chloro-2-pyridyl N02 H S-CFs -
V-5 2-chloro-5-thiazolyl N02 H S-CFs - # Het X2 R3 R5 [C R4aR4b]m
V-6 3-tetrahydrofuryl N02 H S-CFs -
Table W
(I. 36)
Figure imgf000118_0001
Figure imgf000118_0003
Table X
Figure imgf000118_0002
Figure imgf000118_0004
In a specific embodimentin a specific embodiment, the compounds I are selected from the compounds specified in tables O, P, Q, R, S, T, U, V, W and X and in the examples, either as a free base or a tautomer, or a stereoisomer, or a salt thereof.
Compounds of formula (I) according to the present invention can be prepared e.g.
according to the preparation methods and preparation schemes as described below. Compounds of formula (I) according to the present invention can be prepared by standard methods of organic chemistry e.g. by the preparation methods and preparation schemes as described below and in the experimental part of this application. The definition of m, Het, X1, X2, W1, W2, W3, W4, R1, R2, R3, R4a, R4b and R5 of the molecular structures given in the schemes below are as defined above. Room temperature means a temperature range between about 20 and 25°C.
An example of a general method for the preparation of compounds of formula (I) is shown below in Scheme A. Thus, construction of the heterocyclic element 3 present in compounds of formula (I) can be achieved, for example, by alkylation of the appropriate 2-amino heterocycle precursor 1 with the appropriate reagent of formula 2. The transformation is preferably carried out in polar solvents such as acetonitrile, acetone, dichloromethane, 1 ,4-dioxane,
tetrahydrofuran, N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methylpyrolidinone or a Ci- C6 alcohol at a temperature ranging between room temperature and the reflux temperature of the solvent. Representative reaction conditions for the alkylation of compounds analogous to formula 1 are given in Tett. Lett. 201 1 , 52(23), 3033-3037 and in US 6,303,638. The synthesis of compounds of formula 5 can be achieved by acylation of the amine functionality in
compounds of formula 3 using carboxylic acid derivatives 4 which are activated in situ. The transformation is preferably carried out in polar solvents such as acetonitrile, acetone, 1 ,4- dioxane, tetrahydrofuran, N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N- methylpyrolidinone or in an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2- dimethoxyethane at temperatures ranging between room temperature and the reflux
temperature of the solvent. A representative procedure condition for the acylation is given in Journal of Medicinal Chemistry, 2012, 55, 7378-7391. Examples of suitable leaving groups (LG) in formula 2 include, but are not limited to: halogen, alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, alkyl phosphonate. Examples of suitable leaving groups (LG2) in formula 4 include, but are not limited to: halogen, alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, alkyl phosphonate and various activated esters derived from the reaction of a free carboxylic acid with a peptide coupling reagent in the presence of an amine base (Chem. Rev., 2011 , 777 (1 1 ), 6557-6602). Suitable coupling reagents are for example PyBrop (bromotripyrrolidino- phosphonium hexafluorophosphate), PPA (propylphosphonic anhydride) or Ghosez's reagent. A reversal of the order of these two steps would also result in an acceptable synthesis of the desired compounds. Scheme A:
Figure imgf000120_0001
1 3 5
Compounds of formula (I) can also be prepared using an alternative strategy to install the cyano group as is shown below in Scheme B. Thus, construction of intermediate 3 proceeds as described in Scheme A, and amine functionality present in intermediates of type 3 can then be acylated with a reagent of type 6. The transformation is preferably carried out in polar solvents such as acetonitrile, acetone, tetrahydrofuran, 1 ,4-dioxane, Ν,Ν-dimethylformamide, N,N- dimethylacetamide, N-methylpyrolidinone or in an inert solvent such as dichloromethane, 1 ,2- dichloroethane, or 1 ,2-dimethoxyethane at temperatures ranging between room temperature and the reflux temperature of the solvent. Representative procedure conditions for the acylation of 3 are given in Journal of Medicinal Chemistry, 1988, 31 , 4, 807-814. In reagent 6, suitable examples of substitutent Z are: halogen, alkyi sulfonate, halo alkyi sulfonate, aryl sulfonate, phosphate, phosphonate. Examples of suitable leaving groups (LG3) in formula 6 include, but are not limited to: halogen, alkyi sulfonate or haloalkyi sulfonate, alkyi phosphonate, and various activated esters derived from the reaction of the free carbonic acid with a peptide coupling reagent in the presence of an amine base (Chem. Rev., 2011 , 777 (1 1 ), 6557-6602). In the next step, Z is displaced through the action of a cyanide containing compound 8 to afford the desired compound 5, wherein X2 is cyano or Z is displaced through the action of a nitro containing compound 8 to afford the desired compound 5, wherein X2 is nitro. The
transformation is preferably carried out in polar solvents such as acetonitrile, acetone, tetrahydrofuran, 1 ,4-dioxane, N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methylpyrolidinone, a C-I-C6 alcohol or in an inert solvent such as dichloromethane, 1 ,2-dichloroethane, 1 ,2-dimethoxyethane, benzene, toluene, mesitylene, cymenes, or xylenes at temperatures ranging between room temperature and the reflux temperature of the solvent. Examples of suitable Y in formula 8, if X2 is cyano, include, but are not limited to: a metal of group 1 , 2, 1 1 or 12 of the peridodic table (by modern lUPAC numbering), hydrogen, Si(Ci-C4-alkyl)3 or
C(CH3)20H. Examples of suitable cyanide containing compounds 8 are: LiCN, NaCN, KCN, CuCN, Cu(CN)2, Zn(CN)2, HCN, TMS-CN (trimethylsilylcyanide), and acetone cyanohydrin. Representative procedure conditions for such a reaction are given in Journal of Medicinal Chemistry, 1989, 32, 1673-1681. Examples of suitable Y in formula 8, if X2 is nitro, include, but are not limited to: a metal of group 1 , 2, 1 1 or 12 of the peridodic table (by modern lUPAC numbering) or tetraalkylammonium, Examples of suitable nitro containing compounds (8) include, but are not limited to: sodium nitrite, potassium nitrite, silver nitrite, and tetraalkylammonium nitrites. A representative procedure conditions for this exchange reaction is given in Journal of American Chemical Society 1949, 71 , 1292-1297. A reversal of the order of these steps would also result in an acceptable synthesis of the desired compounds of formula (I).
Scheme B:
Figure imgf000121_0001
Figure imgf000121_0002
5
In cases where X1 is a sulfur atom, the sulfur atom is best installed in a subsequent step from the compound where X1 is an oxygen atom as detailed in Scheme C.
Scheme C:
Figure imgf000121_0003
9 11
Here C=0 containing compound 9 is transformed into C=S containing compound 1 1. The transformation is preferably carried out using a reagent of substructure 10 in polar solvents such as acetonitrile, acetone, tetrahydrofuran, Ν,Ν-dimethylformamide, or in an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane at temperatures ranging between room temperature and the reflux temperature of the solvent. Suitable Ra groups in compounds of formula 10 are: thio, alkyl, aryl or substituted aryl. Representative reaction conditions for thionation analogous substrates are given in European Journal of Organic Chemistry, 2000, 3273-3278.
Compounds of the formula 1 are commercially available, for example 2-aminoimidazole (CAS: 6646-51 -1 ) from Fluorochem or Sigma-Aldrich; 2-aminoimidazole as sulfate salt (CAS: 1450-93-7) from Sigma-Aldrich.
Compounds of formula 3 can be preprared in analogy to the methods described in US 6303638, e.g. compounds of formula 3, wherein W1 is S and W2-W3-W4 is -C(Rv2Rw2)-C(Rv3Rw3)- or W is S or NRw and W2-W3-W4 is -C(Rv4)=C(Rv5)-.
Compounds of formula 3, wherein W1 is NRw1, W2-W3-W4 is -C(Rv2Rw2)-0-C(Rv3Rw3)- can be prepared in analogy to the method described in J.Agr. Food. Chem. 2003, 51 , 1823-1830, followd by a reduction with e.g. iron.
Compounds of formula 3, wherein W1 is NRw1, W2-W3-W4 is -C(Rv2Rw2)-C(Rv3Rw3)- can be prepared in analogy to the method described in Journal of Agricultural and Food Chemistry, 56(17), 8023-8029; 2008.
If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds (I) or by customary modifications of the synthesis routes described.
The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by
chromatography, for example on alumina or silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils, which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or digestion.
Due to their excellent activity, the compounds of the present invention may be used for controlling invertebrate pests.
Accordingly, the present invention also provides a method for combatting or controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of the present invention or a composition as defined above. The invention also relates to the use of a compound of the invention, of a stereoisomer and/or of an agriculturally or veterinarily acceptable salt thereof for combating invertebrate pests
Preferably, the method of the invention serves for protecting plant propagation material (such as seed) and the plant which grows therefrom from invertebrate pest attack or infestation and comprises treating the plant propagation material (such as seed) with a pesticidally effective amount of a compound of the present invention as defined above or with a pesticidally effective amount of an agricultural composition as defined above and below. The method of the invention is not limited to the protection of the "substrate" (plant, plant propagation materials, soil material etc.) which has been treated according to the invention, but also has a preventive effect, thus, for example, according protection to a plant which grows from a treated plant propagation materials (such as seed), the plant itself not having been treated.
Alternatively preferably, the method of the invention serves for protecting plants from attack or infestation by invertebrate pests, which method comprises treating the plants with a pesticidally effective amount of at least one compound of the invention, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.
The invention further provides an agricultural composition for combating invertebrate pests, which comprises such an amount of at least one compound according to the invention and at least one inert liquid and/or solid agronomically acceptable carrier that has a pesticidal action and, if desired, at least one surfactant.
Such a composition may comprise a single active compound of the present invention or a mixture of several active compounds of the present invention. The composition according to the present invention may comprise an individual isomer or mixtures of isomers or a salt as well as individual tautomers or mixtures of tautomers.
As used herein, the term "compound(s) of the present invention" or "compound(s) according to the invention" refers to the compound(s) of formula (I) as defined above, which are also referred to as "compound(s) of formula I" or "compound(s) I" or "formula I compound(s)", and includes their salts, tautomers, stereoisomers, and N-oxides. The compounds of the formula (I) including their stereoisomers, tautomers and salts are in particular suitable for efficiently controlling arthropodal pests such as arachnids, gastropods, myriapedes and insects as well as nematodes.
The compounds of the formula (I) are especially suitable for efficiently combating insects, in particular the following pests:
insects from the order of Lepidoptera, for example Achroia grisella, Aden's spp. such as A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophila pometaria, Ampelophaga rubiginosa, Amyelois transitella, Anacampsis sarcitella, Anagasta kuehniella, Anarsia lineatella, Anisota senator/a, Antheraea pernyi,
Ant/cars/a (=Thermesia) spp. such as A. gemmatalis; Apamea spp., Aproaerema modicella, Arch '/ps spp. such as A. argyrospila, A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella, Argyroploce spp., Argyrotaenia spp. such as A. velutinana; Athetis mindara,
Austroasca viridigrisea, Autograph a gamma, Autograph a nigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C. podana; Cactoblastis cactorum, Cadra cautella, Calingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata, Chilo spp. such as C. Indicus, C. suppressaiis, C. parteiius; Choreutis pariana, Choristoneura spp. such as C. conflictana, C. fumiferana, C longicellana, C murinana, C occidentalis, C rosaceana;
Chrysodeixis (=Pseudoplusia) spp. such as C. eriosoma, C. includens; Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Cochylis hospes, Coleophora spp., Colias eurytheme, Conopomorpha spp., Conotrachelus spp., Cop/tarsia spp., Corcyra cepha/onica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis, Cydia (=Carpocapsa) spp. such as C.
pomonella, C latiferreana; Dalaca noctuides, Datana integerrima, Dasychira pinicola,
Dendrolimus spp. such as D. pini, D. spectabilis, D. sibiricus; Desmia funeralis, Diaphania spp. such as D. nitidalis, D. hyalinata; Diatraea grandiosella, Diatraea saccharalis, Diphthera festiva, Earias spp. such as E. insulana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curia/is, E/asmopa/pus lignosellus, Eldana saccharina, Endopiza viteana, Ennomos subsignaria, Eoreuma loftini, Ephestia spp. such as E. cautella, E. elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etie/ia spp., Eu/ia spp., Eupoeci/ia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bou liana, Faronta albilinea, Feltia spp. such as F. subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. such as G.
funebrana, G. molesta, G. inopinata; Ha 'lysidota spp., Harrisina americana, Hedylepta spp., Helicoverpa spp. such as H. armigera (=Heliothis armigera), H. zea (=Heliothis zea); Heliothis spp. such as H. assulta, H. subflexa, H. virescens; Hellula spp. such as H. undalis, H. rogatalis; Helocoverpa gelotopoeon, Hemileuca oliviae, Herpetogramma licarsisalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Kakivoria flavofasciata, Keiferia lycopersicella, Lambdina fiscellaria fiscellaria, Lambdina fiscellaria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Lerodea eufala, Leucinodes orbonalis, Leucoma salicis, Leucoptera spp. such as L. coffeella, L. scitella; Leuminivora lycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattia octo (=Amyna axis), Lobes/a botrana, Lophocampa spp., Loxagrot/s a/bicosta, Loxostege spp. such as L. sticticalis, L. cereralis; Lymantria spp. such as L. dispar, L. monacha; Lyonetia clerkella, Lyonetia prunifoliella, Malacosoma spp. such as M. americanum, M. californicum, M.
constrictum, M. neustria; Mamestra spp. such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulalis, Megalopyge lanata, Melanchra picta, Melanitis leda, Mods spp. such as M. lapites, M. repanda; Mods latipes, Monochroa fragariae, Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantalis, Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes indicata, Omphisa anastomosalis, Operophtera brumata, Orgy/a pseudotsugata, Or/a spp., Orthaga thyrisa/is, Ostrinia spp. such as O. nubilalis; Oulema oryzae, Paleacrita vernata, Panolis flammea, Parnara spp., Papaipema nebris, Papilio cresphontes, Paramyelois transitella, Paranthrene regalis, Paysandisia archon, Pectinophora spp. such as P. gossypiella; Peridroma saucia, Perileucoptera spp., such as P. coffeella; Phalera bucephala, Phryganidia californica, Phthorimaea spp. such as P. operculella; Phyllocnistis citrella, Phyllonorycter spp. such as P. biancardeiia, P. crataegeiia, P. issikii, P. ringoniella; Pieris spp. such as P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. such as P. flavedana, P.
idaeusalis, P. stultana; Platyptilia carduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp, Plutella maculipennis, Plutella xylostella, Pontia protodica, Prays pp., Prodenia spp., Proxenus /epigone, Pseudaletia spp. such as P. sequax, P. unipuncta; Pyrausta nubilalis, Rachiplusia nu, Rich/a albicosta, Rhizobius ventralis, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festaliella, Scirpophaga spp. such as S. incertulas, S. innotata; Scotia segetum, Sesamia spp. such as S. inferens, Seudyra subflava, Sitotroga cerealella, Sparganothis pilleriana, Spilonota lechriaspis, S. ocellana,
Spodoptera (=Lamphygma) spp. such as S. cosmoides, S. eridania, S. exigua, S. frugiperda, S. latisfascia, S. littoralis, S. litura, S. omithogalli; Stigmella spp., Stomopteryx subsecivella, Strymon bazochii, Sylepta derogata, Synanthedon spp. such as S. exitiosa, Tec/a solanivora, Telehin ileus, Thaumatopoea pityocampa, Thaumatotibia (=Cryptophlebia) leucotreta,
Thaumetopoea pityocampa, Thecla spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella, Tinea spp. such as T. cloacella, T. pellionella; Tineola bisselliella, Tortrix spp. such as T. viridana; Trichophaga tapetzella, Trichoplusia spp. such as T. ni; Tuta
(=Scrobipalpula) absoluta, Udea spp. such as U. rubigalis, U. rubigalis; Virachola spp.,
Yponomeuta padella, and Zeiraphera canadensis;
insects from the order of Coleoptera, for example Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. such as A. anxius, A. planipennis, A.
sinuatus; Agriotes spp. such as A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimaiius soistitiaiis, Anisandrus dispar, Anisopiia austriaca, Anobium punctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophora spp. such as A. glabripennis; Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such as A. linearis; Attagenus spp., Aulacophora fern oral is, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne, Callopistria floridensis, Callosobruchus chinensis, Cameraria ohridella, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as C. assimilis, C. napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. such as C. vespertinus;
Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. such as C. destructor;
Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dactyl/spa ba/yi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undecimpunctata, D. speciosa, D. longicornis, D. semipunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera, Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis), Enaphalodes rufulus, Epilachna spp. such as E. varivestis, E. vigintioctomaculata; Epitrix spp. such as E. hirtipennis, E. similaris; Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Gnathocerus cornutus, Hell u la undalis, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp. such as H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp. such as L. bilineata, L. melanopus; Leptinotarsa spp. such as L. decemlineata; Leptispa pygmaea, Limonius californicus,
Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp. such as L. bruneus;
Liogenys fuscus, Macrodactylus spp. such as M. subspinosus; Maladera matrida, Megapiatypus mutates, Megascelis spp., Me/anotus communis, Meligethes spp. such as M. aeneus;
Melolontha spp. such as M. hippocastani, M. melolontha; Metamasius hemipterus, Microtheca spp., Migdolus spp. such as M. fryanus, Monochamus spp. such as M. alternatus; Naupactus xanthographus, Niptus hololeucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros,
Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P. cochleariae; Phoracantha recurva, Phyllobius pyri, Phyllopertha horticola, Phyllophaga spp. such as P. helleri; Phyllotreta spp. such as P.
chrysocephala, P. nemorum, P. striolata, P. vittula; Phyllopertha horticola, Pop/ilia japonica, Premnotrypes spp., Psacothea hilaris, Psylliodes chrysocephala, Prostephanus truncates,
Psylliodes spp., Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp. such as R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R. vulneratus; Saperda Candida, Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp. such as T.
castaneum; Trogoderm a spp., Tychius spp., Xylotrechus spp. such as X. pyrrhoderus; and, Zabrus spp. such as Z. tenebrioides;
insects from the order of Diptera for example Aedes spp. such as A. aegypti, A.
albopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. macuiipennis, A. minimus, A. quadrimacuiatus, A. sinensis; Bactrocera invadens, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chrysomyia spp. such as C. bezziana, C. hominivorax, C. macellaria;
Chrysops atlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp. such as C.
hominivorax; Contarinia spp. such as C. sorghicola; Cordylobia anthropophaga, Culexspp. such as C. nigripalpus, C. pip/ens, C. quinquefasciatus, C. tarsalis, C. tritaeniorhynchus;
Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. such as D. antique, D. coarctata, D. platura, D. radicum; Dermatobia hominis, Drosophila spp. such as D. suzukii, Fannia spp. such as F. canicularis; Gastraphilus spp. such as G. intestinalis; Geomyza tipunctata, Glossina spp. such as G. fuscipes, G. morsitans, G. pa/pa/is, G tachinoides;
Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppobosca spp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. trifolii; Lucilia spp. such as L. caprina, L. cuprina, L. sericata; Lycoria pectoraiis, Mansonia titiiianus, Mayetioia spp. such as M. destructor; Musca spp. such as M. autumnalis, M. domestica; Muscina stabulans, Oestrus spp. such as O. ovis; Opomyza florum, Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami,
Phlebotomus argentipes, Phorbia spp. such as P. antiqua, P. brassicae, P. coarctata;
Phytomyza gymnostoma, Prosimuiium mixtum, Psiia rosae, Psorophora coiumbiae, Psorophora discolor, Rhagoletis spp. such as R. cerasi, R. cingulate, R. indifferens, R. mendax, R.
pomonella; Rivellia quadrifasciata, Sarcophaga spp. such as S. haemorrhoidalis; Simulium vittatum, Sitodiplosis mosellana, Stomoxys spp. such as S. calcitrans; Tabanus spp. such as T. atratus, T. bovinus, T. Iineoia, T. similis; Tannia spp., Thecodipiosis japonensis, Tipuia oieracea, Tipuia paludosa, and Wohlfahrtia spp;
insects from the order of Thysanoptera for example, Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femora/is, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. such as S. citri, S. dorsalis, S. perseae;
Stenchaetothrips spp, Taeniothrips cardamom,' Taeniothrips inconsequens, Thrips spp. such as T imagines, T hawaiiensis, T. oryzae, T. pa I mi, T. parvispinus, T. tabaci;
insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. are/Acyrthosipon spp. such as A. onobrychis, A. pisum; Adelges laricis, Adelges tsugae, Adelphocoris spp., such as A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp., Auiacorthum soiani, Aleurocanthus woglumi, Aleurodes spp., Aleurodicus disperses, Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp. , Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp. such as A. craccivora, A. fabae, A. forbesi, A. gossypii, A. grossulariae, A. maidiradicis, A. pomi, A.
sambuci, A. schneideri, A. spiraecola; Arboridia apicalis, Arilus critatus, Aspidiella spp.,
Aspidiotus spp., Atanus spp., Auiacaspis yasumatsui, Auiacorthum soiani, Bactericera cockereiii (Paratrioza cockereiii), Bemisia spp. such as B. argentifolii, B. tabaci (Aleurodes tabaci); Blissus spp. such as B. leucopterus; Brachycaudus spp. such as B. cardui, B. helichrysi, B. persicae, B. prunicola; Brachycolus spp., Brachycorynella asparagi, Brevicoryne brassicae, Cacopsylla spp. such as C. fulguralis, C. pyricola (Psylla piri); Calligypona marginata, Calocoris spp.,
Campylomma livida, Capitophorus horn/, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp., Ceratovacuna I an ig era, Ceroplastes ceriferus, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimex spp. such as C. hemipterus, C. lectularius; Coccomytilus halli, Coccus spp. such as C. hesperidum, C. pseudomagno/iarum, Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurodes spp. such as D. citrifolii;
Dalbulus maidis, Diaphorina spp. such as D. citri; Diaspis spp. such as D. bromeliae; Dichelops furcatus, Diconocoris hewetti, Dora/is spp., Dreyfus/a nordmannianae, Dreyfus/a piceae, Drosicha spp., Dysaphis spp. such as D. plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudoso/ani, Dysdercus spp. such as D. cingulatus, D. intermedins; Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp. such as E. fabae, E. solana; Epidiaspis leperii,
Eriosoma spp. such as E. lanigerum, E. pyricola; Erythroneura spp., Eurygaster spp. such as E. integ ceps; Euscelis bilobatus, Euschistus spp. such as E. heros, E. impictiventris, E. servus; Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei, Halyomorpha spp. such as H. halys; Heliopeltis spp., Homalodisca vitripennis (=H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, lcerya spp. such as /. purchase; Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus floccissimus, Lepidosaphes spp. such as L. ulmi; Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L.
hesperus, L. lineolaris, L pratensis; Maconellicoccus hirsutus, Marchalina hellenica, Macropes excavatus, Macrosiphum spp. such as M. rosae, M. avenae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Melanocallis (=Tinocallis) caryaefoliae, Metcafiella spp.,
Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus spp. such as M. ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians; Nasonovia ribis-nigri, Neotoxoptera formosana, Neomegaiotomus spp, Nephotettix spp. such as N. malayanus, N. nigropictus, N. parvus, N. virescens; Nezara spp. such as N. viridula;
Nilaparvata lugens, Nysius button/, Oeba/us spp. such as O. pugnax; Oncometopia spp., Orthezia praelonga, Oxycaraenus hyalinipennis, Parabemisia myricae, Parlatoria spp.,
Parthenolecanium spp. such as P. corn/, P. persicae; Pemphigus spp. such as P. bursar/us, P. popuiivenae; Peregrinus maidis, Perkinsieiia saccharicida, Phenacoccus spp. such as P. aceris, P. gossypii; Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp. such as P. devastatrix, Piesma quadrata, Piezodorus spp. such as P. guildinii; Pinnaspis aspidistrae, Pianococcus spp. such as P. citri, P. ficus; Prosapia bicincta, Protopulvinaria pyriformis, Psallus seriatus,
Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such as P. comstocki; Psylla spp. such as P. mali; Pteromalus spp., Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. such as R.
pseudobrassicas, R. insertum, R. maidis, R. pad/; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaptocoris spp., Scaphoides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insularis, Spissistilus festinus (=Stictocephala festina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis takeyai,
Tenalaphara malayensis, Tetraleurodes perseae, Therioaphis maculate, Thyanta spp. such as T. accerra, T. perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. such as T. aurantii;
Trialeurodes spp. such as T. abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifolii,
Insects from the order Hymenoptera for example Acanthomyops interjectus, Athalia rosae,
Atta spp. such as A. capiguara, A. cephalotes, A. cephalotes, A. laevigata, A. robusta, A.
sexdens, A. texana, Bombus spp., Brachymyrmex spp., Camponotus spp. such as C.
floridanus, C. pennsylvanicus, C. modoc; Cardiocondyla nuda, Chalibion sp, Crematogaster spp., Dasymutilla occidentalis, Diprion spp., Dolichovespula maculata, Dorymyrmex spp., Dryocosmus kuriphilus, Formica spp., Hoplocampa spp. such as H. minuta, H. testudinea;
Iridomyrmex humilis, Lasius spp. such as L. niger, Linepithema humile, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechina longicornis, Paravespula spp., such as P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. such as P. megacephala; Pogonomyrmex spp. such as P. barbatus, P. californicus, Polls tes rub/gin osa, Prenolepis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenopsis spp. such as S. geminata, S.invicta, S. molesta, S. richteri, S. xyloni, Sphecius speciosus, Sphex spp., Tapinoma spp. such as T.
melanocephalum, T. sessile; Tetramorium spp. such as T. caespitum, T. bicarinatum, Vespa spp. such as V. crabro; Vespula spp. such as V. squamosal; Wasmannia auropunctata, Xylocopa sp;
Insects from the order Orthoptera for example Acheta domesticus, Calliptamus italicus,
Chortoicetes terminifera, Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. such as G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis, Kraussaria anguiifera, Locusta spp. such as L. migratoria, L. pardaiina; Meianopius spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus;
Nomadacris septemfasciata, Oedaleus senegalensis, Scapteriscus spp., Schistocerca spp. such as S. americana, S. gregaria, Stemopelmatus spp., Tachycines asynamorus, and
Zonozerus variegatus;
Pests from the Class Arachnida for example Acari,e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A. americanum, A. variegatum, A.
maculatum), Argas spp. such as A. persicu), Boophilus spp. such as B. annulatus, B.
decoloratus, B. microplus, Dermacentor spp. such as D.silvarum, D. andersoni, D. variabilis, Hyalomma spp. such as H. truncatum, Ixodes spp. such as /. ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus, Rhipicephaius sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. such as P. ovis, Rhipicephaius spp. such as R. sanguineus, R. appendiculatus,
Rhipicephaius everts/, Rhizoglyphus spp., Sarcoptes spp. such asS. Scabiei, and Family
Eriophyidae including Acer/a spp. such as A. she/doni, A. anthocoptes, Acallitus spp., Aculops spp. such as A. iycopersici, A. pe/ekassi, Acu/us spp. such as A. sch/echtenda/i; Colomerus vitis, Epitrimerus pyri, Phyllocoptruta oleivora; Eriophytes ribis and Eriophyes spp. such as Eriophyes she/doni, Family Tarsonemidae including Hemitarsonem us spp., Phytonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp. Steneotarsonemus spinki, Family Tenuipalpidae including Brevipalpus spp. such as B. phoenicis, Family Tetranychidae including Eotetranychus spp., Eutetranychus spp., O/igonychus spp., Petrobia iatens,
Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseulus, T. telarius and T. urticae, Bryobia praetiosa, Panonychus spp. such as P. ulmi, P. citri,
Metatetranychus spp. and O/igonychus spp. such as O. pratensis, O. perseae, Vasates
Iycopersici, Raoiella indica, /¾/77// Carpoglyphidae including Carpoglyphus spp.; Penthaleidae spp. such as a/otydeus destructor, Family Demodicidae with species such as Demodexspp:, Family Trombicidea including Trombicula spp:, Family Macronyssidae including Ornothonyssus spp.; Family Pyemotidae including Pyemotes tritici, Tyrophagus putrescentiae; Family Acaridae including Acarus siro; Family Araneida including Latrodectus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosceles rec/usa;
Pests from the Phylum Nematoda, for example, plant parasitic nematodes such as root- knot nematodes, Meloidogyne spp. such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H. schachtii, H. trifo/ii; Seed gall nematodes, Anguina spp.; Stem and foliar nematodes, Aphelenchoides spp. such as A. besseyi; Sting nematodes, Belonolaimus spp. such as B. longicaudatus; P\ne nematodes, Bursaphelenchus spp. such as B. lignicolus, B. xylophilus; Ring nematodes, Criconema spp., Criconemella spp. such as C. xenop/axand C. ornata; and, Criconemoides spp. such as Criconemoides informis; Mesocriconema spp.; Stem and bulb nematodes, Ditylenchus spp. such as D. destructor, D. dipsaci; Awl nematodes, Dolichodorus spp.; Spiral nematodes, Heliocotylenchus multicinctus; Sheath and sheathoid nematodes, Hemicycliophora spp. and Hemicriconemoides spp.; Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; False rootknot nematodes, Nacobbus spp.; Needle nematodes, Longidorus spp. such as L. elongatus; Lesion nematodes, Pratylenchus spp. such as P.
brachyurus, P. neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopholus spp. such as R. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform
nematodes, Rotylenchus spp. such as R. robustus, R. reniformis; Scutellonema spp.; Stubby- root nematode, Trichodorus spp. such as T. obtusus, T. primitivus; Paratrichodorus spp. such as P. minor; Stunt nematodes, Tylenchorhynchus spp. such as 7! claytoni, T. dub/us; Citrus nematodes, Tylenchulus spp. such as 7! semipenetrans; Dagger nematodes, Xiphinema spp.; and other plant parasitic nematode species;
Insects from the order Isoptera for example Calotermes flavicollis, Coptotermes spp. such as C. formosanus, C. gestroi, C. acinaciformis; Cornitermes cumuians, Cryptotermes spp. such as C. brevis, C. cavifrons; Globitermes sulfureus, Heterotermes spp. such as H. aureus, H. longiceps, H. tenuis; Leucotermes flavipes, Odontotermes spp., I ncisitermes spp. such as /. minor, I. Snyder, Marginitermes hubbardi, Mastotermes spp. such as M. darwiniensis
Neocapritermes spp. such as N. opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp. such as Z. angusticollis, Z. nevadensis, Reticulitermes spp. such as R. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. santonensis, R.
virginicus; Termes natalensis,
Insects from the order Blattaria for example Blatta spp. such as B. orientalis, B. lateralis; Blattella spp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchlora nivea, Peripianeta spp. such as P. americana, P. austraiasiae, P. brunnea, P. fuiigginosa, P. japonica; Supella longipalpa, Parcoblatta pennsylvanica, Eurycotis floridana, Pycnoscelus surinamensis, Insects from the order Siphonoptera for example Cediopsylla simples, Ceratophyllus spp., Ctenocephalides spp. such as C. felis, C. cam's, Xenopsylla cheopis, Pulex irritans,
Trichodectes cam's, Tunga penetrans, and Nosopsyllus fascia tus,
Insects from the order Thysanura for example Lepisma saccharina , Ctenolepisma urbana, and Therm obia domes tica, Pests from the class Chilopoda for example Geophilus spp., Scutigera spp. such as Scutigera coleoptrata,
Pests from the class Diplopoda for example Blaniulus guttulatus, Ju/us spp., Narceus spp.,
Pests from the class Symphyla for example Scutigerella immaculata,
Insects from the order Dermaptera, for example Forficula auricularia,
Insects from the order Collembola, for example Onychiurus spp., such as Onychiurus armatus,
Pests from the order Isopoda for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber,
Insects from the order Phthiraptera, for example Damalinia spp., Pedicuius spp. such as Pedicuius humanus capitis, Pedicuius humanus corporis, Pedicuius humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis,
Linognathus spp. such as Linognathus vituii; Bovicoia bovis, Menopon gaiiinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.,
Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, for example, Dreissena spp:, class
Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp.; from the class of the helminths, for example, Ancyiostoma duodenale, Ancyiostoma ceylanicum, Acylostoma braziiiensis, Ancyiostoma spp., Ascaris lubricoides, Ascaris spp., Brugia maiayi, Brugia timori, Bunostomum spp., C ha bertia spp., Clonorchis spp., Cooper/a spp., Dicrocoelium spp.,
Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp. such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni,
Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.
Compounds of the formula (I) are particularly useful for controlling insects of the orders Hemiptera and Thysanoptera.
The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.
An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof. The term "pesticidally effective amount" is defined below.
For use in a method according to the present invention, the compounds of the formula (I) or the mixtures thereof can be converted into the customary agrochemical compositons, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules and directly sprayable solutions. The use form depends on the particular purpose and application method. Formulations and application methods are chosen to ensure in each case a fine and uniform distribution of the compound of the formula (I) according to the invention. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Mono-graph No. 2, 6th Ed. May 2008, CropLife International.
The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New
developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fracpolytions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo^hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates;
amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch;
fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 :
Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul- fates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox- ylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth- oxylates.
Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Exam-pies of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid
alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer-rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers. Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a compound I according to the invention and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a compound I according to the invention and 1 -10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water- insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium
lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g.
polyvinylalcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dis-persion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. ix) Microemulsion (ME)
5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insolu- ble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylme- thene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of a polyurea microcapsule. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.
xi) Dustable powders (DP, DS)
1 -10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
xii) Granules (GR, FG)
0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray- drying or the fluidized bed.
xiii) Ultra-low volume liquids (UL)
1 -50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably be-tween 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub- stance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions cormprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1. The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e. g. components comprising compounds of the present invention and/or mixing partners as defined above, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e. g. components comprising compounds of the present invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
The compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the present invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the present invention.
The compounds of the present invention are also suitable for use in combating or controlling animal pests. Therefore, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the present invention.
The compounds of the present invention are effective through both contact and ingestion. Furthermore, the compounds of the present invention can be applied to any and all
developmental stages, such as egg, larva, pupa, and adult.
The compounds of the present invention can be applied as such or in form of
compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above. The components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture "in situ" on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application. Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow. Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment. For foliar applications, it can be advantageous to modify the behavior of the pests by use of pheromones in combination with the compounds of the present invention. Suitable pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and
semiochemicals, such as http://www.pherobase.com.
As used herein, the term "contacting" includes both direct contact (applying the
compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
The term "animal pest" includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects. Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
The term "crop" refers to both, growing and harvested crops.
The term "plant" includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as beans, lentils, peas, alfalfa or soybeans; oil plants, such as rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, pumpkins, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g. carnation, petunias,
geranium/pelargoniums, pansies and impatiens), shrubs, broad-leaved trees (e.g. poplar) or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant" is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof.
Plants, which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice. In plants, which have been modified by mutagenesis or genetic engineering, one or more genes have been mutagenized or integrated into the genetic material of the plant. The one or more mutagenized or integrated genes are preferably selected from pat, epsps, crylAb, bar, cry1 Fa2, crylAc, cry34Ab1 , cry35AB1 , cry3A, cryF, cry1 F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asnl , and ppo5. The mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant. Such properties, also known as traits, include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control. Of these properties, herbicide tolerance, e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance, is of particular importance. Several plants have been rendered tolerant to herbicides by mutagenesis, for example Clearfield® oilseed rape being tolerant to imidazolinones, e.g. imazamox. Alternatively, genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
Furthermore, insect resistance is of importance, in particular lepidopteran insect resistance and coleopteran insect resistance. Insect resistance is typically achieved by modifying plants by integrating cry and/or vip genes, which were isolated from Bacillus thuringiensis (Bt), and code for the respective Bt toxins. Genetically modified plants with insect resistance are commercially available under trade names including WideStrike®, Bollgard®, Agrisure®, Herculex®,
YieldGard®, Genuity®, and Intacta®. Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance. In general, all relevant modified plants in connection with singular or stacked traits as well as detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http://www.isaaa.org/gmapprovaldatabase) and "Center for Environmental Risk Assessment (CERA)" (http://cera-gmc.org/GMCropDatabase).
It has surprisingly been found that the pesticidal activity of the compounds of the present invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.
The term "plant propagation material" refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
The term "seed" embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various
compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
In the case of soil treatment, in furrow application or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
The compounds of the present invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects. The present invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermination with a compound of the present invention. The protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.
The term "seed treatment" comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in- furrow application methods. Preferably, the seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
The present invention also comprises seeds coated with or containing the active compound. The term "coated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the
propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias,
geranium/pelargoniums, pansies and impatiens.
In addition, the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having
pregerminated the latter. Preferably, the formulations are applied such that germination is not included.
The active substance concentrations in ready-to-use formulations, which may be obtained after two-to-tenfold dilution, are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight.
In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1 -800 g/l of active ingredient, 1 -200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water. Especially preferred FS formulations of the compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
In the treatment of seed, the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
The invention therefore also relates to seed comprising a compound of the present invention, or an agriculturally useful salt thereof, as defined herein. The amount of the compound of the present invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
The compounds of the present invention may also be used for improving the health of a plant. Therefore, the present invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the present invention.
As used herein "an effective and non-phytotoxic amount" means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.
The terms "plant" and "plant propagation material" are defined above.
"Plant health" is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (for example increased biomass and/or increased content of valuable ingredients), quality (for example improved content or composition of certain ingredients or shelf life), plant vigour (for example improved plant growth and/or greener leaves ("greening effect"), tolerance to abiotic (for example drought) and/or biotic stress (for example disease) and production efficiency (for example, harvesting efficiency, processability).
The above identified indicators for the health condition of a plant may be interdependent and may result from each other. Each indicator is defined in the art and can be determined by methods known to a skilled person. The compounds of the invention are also suitable for use against non-crop insect pests. For use against said non-crop pests, compounds of the present invention can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied). Furthermore, drenching and rodding methods can be used.
As used herein, the term "non-crop insect pest" refers to pests, which are particularly relevant for non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitos, crickets, or cockroaches.
The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature (e.g. http://www.pherobase.com), and are known to those skilled in the art.
For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.
Formulations of the compounds of the present invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries such as emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants.
The oil spray formulations differ from the aerosol recipes in that no propellants are used. For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
The compounds of the present invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of the present invention and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like.
Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. The compounds of the present invention and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
Customary application rates in the protection of materials are, for example, from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m2 treated material, desirably from 0.1 g to 50 g per m2.
Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.
The compounds of the present invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the present invention also relates to the use of a compound of the present invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites.
Furthermore, the present invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of the present invention.
The present invention also relates to the non-therapeutic use of compounds of the present invention for treating or protecting animals against infestation and infection by parasites.
Moreover, the present invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.
The compounds of the present invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the present invention relates to a method of combating or controlling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the present invention.
The present invention also relates to the non-therapeutic use of compounds of the present invention for controlling or combating parasites. Moreover, the present invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.
The compounds of the present invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds of the present invention can be applied to any and all developmental stages.
The compounds of the present invention can be applied as such or in form of
compositions comprising the compounds of the present invention.
The compounds of the present invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.
The compounds of the present invention and compositions comprising them can be applied orally, parenterally or topically, e.g. dermally. The compounds of the present invention can be systemically or non-systemically effective.
The application can be carried out prophylactically, therapeutically or non-therapeutically. Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected.
As used herein, the term "contacting" includes both direct contact (applying the
compounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at it's locus for the latter) and indirect contact (applying the compounds/compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of the compounds of the present invention.
The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.
As used herein, the term "parasites" includes endo- and ectoparasites. In some embodiments of the present invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.
The compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively:
fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides cam's, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pip/ens, Cu/ex n/gr/pa/pus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Cu/iseta me/anura, Derma tobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina pa/pa/is, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris,
Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lu cilia caprina, Lu cilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor,
Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis; lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capiHatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma macuiatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae, Actinedida (Prostigmata) und Acaridida (Astigmata), e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp.,
Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pteroiichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Lam/nosioptes spp; Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp., and Arilus critatus; Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; Ma\\op ag\da (suborders Arnblycerina and Ischnocerina), e.g.
Tr/menopon spp., Menopon spp., Tr/noton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; Roundworms Nematoda: Wipeworms and
Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), Trichuridae,! Trichuris spp., Capillaria spp.; Rhabditida, e.g. Rhabditis spp., Strongyloides spp., Helicephalobus spp.;
Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooper/a spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp.,
Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris e iy/; Camallanida, e.g. Dracunculus medinensis (guinea worm); Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Thorny headed worms
(Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and
Oncicola spp.; Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis busk/, Clonorchis sinensis,
Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp:, Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium can/hum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp. , a n d Hymenolepis spp.. As used herein, the term "animal" includes warm-blooded animals (including humans) and fish. Preferred are mammals, such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur- bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels. Particularly preferred are domestic animals, such as dogs or cats.
In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
Generally, it is favorable to apply the compounds of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.
For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be
transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.
The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
Suitable preparations are:
- Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;
- Emulsions and suspensions for oral or dermal administration; semi-solid preparations; - Formulations in which the active compound is processed in an ointment base or in an oil- in-water or water-in-oil emulsion base;
- Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further auxiliaries such as acids, bases, buffer salts, preservatives, and solubilizers. Suitable auxiliaries for injection solutions are known in the art. The solutions are filtered and filled sterile.
Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.
Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on. Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.
Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art.
Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art.
Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water-in-oil type or of the oil-in-water type. They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.
Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances,
preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.
Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity. For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form. Suitable auxiliaries for this purpose are known in the art.
The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the present invention.
Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.
Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.
Furthermore, the preparations comprise the compounds of formula I against
endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.
Topical application may be conducted with compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
Generally it is favorable to apply solid formulations which release compounds of the present invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.
The present invention also relates to a mixture of at least one compound of the present invention with at least one mixing partner as defined herein after. Preferred are binary mixtures of one compound of the present invention as component I with one mixing partner as defined herein after as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
Also, in the method of the present invention compounds of formula (I) may be applied with other active ingredients (mixing partners). These additional ingredients may be used
sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients. Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like. Preferred mixing partners are insecticides, nematicides and fungicides.
The following list M of pesticides, grouped and numbered according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the present invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation:
M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of M.1 B organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;
M.2. GABA-gated chloride channel antagonists such as: M.2A cyclodiene organochlorine compounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;
M.3 Sodium channel modulators from the class of M.3A pyrethroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S- cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin,
tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;
M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of M.4A
neonicotinoids, for example acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.2: (2E-)-1 -[(6-Chloropyridin- 3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1 -[(6-Chloropyridin-3- yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; or from the class M.4B nicotine;
M.5 Nicotinic acetylcholine receptor allosteric activators from the class of spinosyns, for example spinosad or spinetoram;
M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin; M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;
M.8 miscellaneous non-specific (multi-site) inhibitors, for example M.8A alkyl halides as methyl bromide and other alkyl halides, or M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;
M.9 Selective homopteran feeding blockers, for example M.9B pymetrozine, or M.9C flonicamid;
M.10 Mite growth inhibitors, for example M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;
M.1 1 Microbial disruptors of insect midgut membranes, for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israe/ensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;
M.12 Inhibitors of mitochondrial ATP synthase, for example M.12A diafenthiuron, or
M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetradifon;
M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, for example chlorfenapyr, DNOC or sulfluramid;
M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, for example nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas as for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;
M.16 Inhibitors of the chitin biosynthesis type 1 , as for example buprofezin;
M.17 Moulting disruptors, Dipteran, as for example cyromazine;
M.18 Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide;
M.19 Octopamin receptor agonists, as for example amitraz;
M.20 Mitochondrial complex III electron transport inhibitors, for example M.20A
hydramethylnon, or M.20B acequinocyl, or M.20C fluacrypyrim;
M.21 Mitochondrial complex I electron transport inhibitors, for example M.21A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
M.22 Voltage-dependent sodium channel blockers, for example M.22A indoxacarb, or
M.22B metaflumizone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]- ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2- methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]- hydrazinecarboxamide;
M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid derivatives, for example spirodiclofen, spiromesifen or spirotetramat; M.24 Mitochondrial complex IV electron transport inhibitors, for example M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;
M.28 Ryanodine receptor-modulators from the class of diamides, as for example flubendiamide, chlorantraniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), tetraniliprole, or the phthalamide compounds M.28.1 : (R)-3-Chlor-N1 -{2-methyl-4-[1 ,2,2,2 -tetrafluor-1 - (trifluormethyl)ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonylethyl)phthalamid and M.28.2: (S)-3- Chlor-N1 -{2-methyl-4-[1 ,2,2,2 -tetrafluor-1 -(trifluormethyl)ethyl]phenyl}-N2-(1 -methyl-2- methylsulfonylethyl)phthalamid, or the compound M.28.3: 3-bromo-N-{2-bromo-4-chloro-6-[(1 - cyclopropylethyl)carbamoyl]phenyl}-1 -(3-chlorpyridin-2-yl)-1 H-pyrazole-5-carboxamide
(proposed ISO name: cyclaniliprole), or the compound M.28.4: methyl-2-[3,5-dibromo-2-({[3- bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1 ,2- dimethylhydrazinecarboxylate; or a compound selected from M.28.5a) to M.28.5d) and M.28.5h) to M.28.5I): M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2- (3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl- lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; M.28.5c) N-[4-chloro-2-[(di-2-propyl-lambda-4- sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5h) N-[4,6- dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; M.28.5i) N-[2-(5-Amino-1 ,3,4-thiadiazol-2-yl)-4-chloro- 6-methylphenyl]-3-bromo-1 -(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide; M.28.5j) 3- Chloro-1 -(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 - methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4- dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide; M.28.5I) N-[4-Chloro-2-[[(1 ,1 -dimethylethyl)amino]carbonyl]-6-methylphenyl]-1 -(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; or
M.28.6: cyhalodiamide; or;
M.29. insecticidal active compounds of unknown or uncertain mode of action, as for example afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen,
triflumezopyrim, or the compounds
M.29.3: 1 1 -(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1 -en-10-one, or the compound
M.29.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4.5]dec-3-en-2- one, or the compound M.29.5: 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H- 1 ,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); or
a compound selected from the group of M.29.6, wherein the compound is selected from M.29.6a) to M.29.6k): M.29.6a) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2- trifluoro-acetamide; M.29.6b) (E/Z)-N-[1 -[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]- 2,2,2-trifluoro-acetamide; M.29.6c) (E/Z)-2,2,2-trifluoro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2- pyridylidene]acetamide; M.29.6d) (E/Z)-N-[1 -[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2- trifluoro-acetamide; M.29.6e) (E/Z)-N-[1 -[1 -(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2- trifluoro-acetamide; M.29.6f) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro- acetamide; M.29.6g) (E/Z)-2-chloro-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro- acetamide; M.29.6h) (E/Z)-N-[1 -[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide; M.29.6i) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro- propanamide.); M.29.6j) N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- thioacetamide; or M.29.6k) N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N'- isopropyl-acetamidine; or the compounds
M.29.8: fluazaindolizine; or the compounds
M.29.9.a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1 - oxothietan-3-yl)benzamide; or M.29.9.b): fluxametamide; or
M.29.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; or a compound selected from the group of M.29.1 1 , wherein the compound is selected from
M.29.1 1 b) to M.29.1 1 p): M.29.1 1 .b) 3-(benzoylmethylamino)-N-[2-bromo-4-[1 , 2,2,3,3,3- hexafluoro-1 -(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.29.1 1.c)
3- (benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; M.29.1 1 .d) N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.29.1 1.e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide; M.29.1 1.f)
4- fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.29.1 1.g) 3-fluoro-N-[2- fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-
(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.29.1 1.h) 2-chloro-N-[3- [[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-
(trifluoromethyl)phenyl]amino]carbonyl]phenyl]- 3-pyridinecarboxamide; M.29.1 1.i) 4-cyano-N-
[2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.29.1 1.j) 4-cyano-3-[(4-cyano-2-methyl- benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]-2- fluoro-benzamide; M.29.1 1.k) N-[5-[[2-chloro-6-cyano-4-[1 ,2,2,3,3,3-hexafluoro-1 -
(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;
M.29.1 1 .1) N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;
M.29.1 1.m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.1 1 .n) 4-cyano-N- [2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.29.1 1 .o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethy^
benzamide; M.29.1 1 .p) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1 -
(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or
a compound selected from the group of M.29.12, wherein the compound is selected from M.29.12a) to M.29.12m): M.29.12.a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.29.12.b) 2-[6-[2-(5-Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.29.12.c) 2-[6-[2- (3-Pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.29.12.d) N-Methylsulfonyl-6-[2-(3- pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.29.12. e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol- 5-yl]pyridine-2-carboxamide; M.29.12.f) N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3- methylthio-propanamide; M.29.12. g) N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3- methylthio-propanamide; M.29.12.h) N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3- methylthio-propanamide; M.29.12. i) N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3- methylthio-propanamide; M.29.12.j) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3- methylthio-propanamide; M.29.12. k) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3- methylthio-propanamide; M.29.12.1) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylthio- propanamide; M.29.12. m) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio- propanamide; or the compounds
M.29.14a) 1 -[(6-Chloro-3-pyridinyl)methyl]-1 , 2,3,5, 6,7-hexahydro-5-methoxy-7-methyl-8- nitro-imidazo[1 ,2-a]pyridine; or M.29.14b) 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; or the compounds
M.29.16a) 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or
M.29.16b) 1 -(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16c) N,5-dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4- carboxamide; M.29.16d) 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M.29.16e) N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5-methyl-N-pyridazin-4- yl-pyrazole-4-carboxamide; M.29.16f) 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M.29.16g) 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4- yl-pyrazole-4-carboxamide; M.29.16h) N-methyl-1-(2-fluoro-1 -methyl-propyl]-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16i) 1 -(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; or M.29.16j) 1 -(4,4-difluorocyclohexyl)-N,5-dimethyl-N- pyridazin-4-yl-pyrazole-4-carboxamide, or
M.29.17 a compound selected from the compounds M.29.17a) to M.29.17j): M.29.17a) N-
(1 -methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.29.17b) N-cyclopropyl-2-(3- pyridinyl)-2H-indazole-4-carboxamide; M.29.17c) N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4- carboxamide; M.29.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; M.29.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide;
M.29.17f) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; M.29.17g) N- [(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.29.17h) N-(2,2- difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.29.17i) 2-(3-pyridinyl )-N-(2- pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.29.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2- (3-pyridinyl)-2H-indazole-5-carboxamide, or
M.29.18 a compound selected from the compounds M.29.18a) to M.29.18d): M.29.18a) N- [3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide;
M.29.18b) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfinyl)propanamide; M.29.18c) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2- difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; M.29.18d) N-[3-chloro-1 -(3- pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide; or the compound
M.29.19 sarolaner, or the compound
M.29.20 lotilaner.
The commercially available compounds of the group M listed above may be found in The Pesticide Manual, 16th Edition, C. MacBean, British Crop Protection Council (2013) among other publications. The online Pesticide Manual is updated regularly and is accessible through http://bcpcdata.com/pesticide-manual.html.
Another online data base for pesticides providing the ISO common names is
http://www.alanwood.net/pesticides.
The M.4 neonicotinoid cycloxaprid is known from WO2010/069266 and WO201 1/069456, the neonicotinoid M.4A.2, sometimes also to be named as guadipyr, is known from
WO2013/003977, and the neonicotinoid M.4A.3 (approved as paichongding in China) is known from WO2007/101369. The metaflumizone analogue M.22B.1 is described in CN10171577 and the analogue M.22B.2 in CN102126994. The phthalamides M.28.1 and M.28.2 are both known from WO2007/101540. The anthranilamide M.28.3 is described in WO2005/077934. The hydrazide compound M.28.4 is described in WO2007/043677. The anthranilamides M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and
WO2013/024010, the anthranilamide Μ.28.5Ϊ) is described in WO201 1/085575, M.28.5j) in WO2008/134969, M.28.5k) in US201 1/046186 and M.28.5I) in WO2012/034403. The diamide compound M.28.6 can be found in WO2012/034472. The spiroketal-substituted cyclic ketoenol derivative M.29.3 is known from WO2006/089633 and the biphenyl-substituted spirocyclic ketoenol derivative M.29.4 from WO2008/06791 1. The triazoylphenylsulfide M.29.5 is described in WO2006/043635, and biological control agents on the basis of bacillus firmus are described in WO2009/124707. The compounds M.29.6a) to Μ.29.6Ϊ) listed under M.29.6 are described in WO2012/029672, and M.29.6j) and M.29.6k) in WO2013/129688. The nematicide M.29.8 is known from WO2013/055584. The isoxazoline M.29.9.a) is described in WO2013/050317. The isoxazoline M.29.9.b) is described in WO2014/126208. The pyridalyl-type analogue M.29.10 is known from WO2010/060379. The carboxamides broflanilide and M.29.1 1.b) to M.29.1 1 .h) are described in WO2010/018714, and the carboxamides M.29.1 1 i) to M.29.1 1.p) in
WO2010/127926. The pyridylthiazoles M.29.12.a) to M.29.12.C) are known from
WO2010/006713, M.29.12.d) and M.29.12.e) are known from WO2012/000896, and M.29.12.†) to M.29.12.m) from WO2010/129497. The compounds M.29.14a) and M.29.14b) are known from WO2007/101369. The pyrazoles M.29.16.a) to M.29.16h) are described in WO2010/034737, WO2012/084670, and WO2012/143317, respectively, and the pyrazoles Μ.29.16Ϊ) and M.29.16j) are described in US 61/891437. The pyridinylindazoles M.29.17a) to M.29.17.j) are described in WO2015/038503. The pyridylpyrazoles M.29.18a) to M.29.18d) are described in US2014/0213448. The isoxazoline M.29.19 is described in WO2014/036056. The isoxazoline M.29.20 is known from WO2014/090918.
The following list of fungicides, in conjunction with which the compounds of the present invention can be used, is intended to illustrate the possible combinations but does not limit them:
A) Respiration inhibitors
Inhibitors of complex III at Q0 site (e. g. strobilurins): azoxystrobin (A.1 .1 ), coumeth- oxystrobin (A.1.2), coumoxystrobin (A.1 .3), dimoxystrobin (A.1.4), enestroburin (A.1 .5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim- methyl (A.1 .9), mandestrobin (A.1.10), metominostrobin (A.1.1 1 ), orysastrobin (A.1.12), picoxy- .strobin (A.1.13), pyraclostrobin (A.1 .14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1 .16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)- phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1.19),
triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1.21 ), fenamidone (A.1.21 ), methyl-/V-[2- [(1 ,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1 .22), 1 -[3- chloro-2-[[1 -(4-chlorophenyl)-1 H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one
(A.1.23), 1 -[3-bromo-2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5- one (A.1.24), 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl- tetrazol-5-one (A.1 .25), 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4- methyl-tetrazol-5-one (A.1 .26), 1 -[2-[[1 -(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro- phenyl]-4-methyl-tetrazol-5-one (A.1 .27), 1 -[2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3- methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.28), 1-[3-chloro-2-[[4-(p-tolyl)thiazol-2- yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1 .29), 1 -[3-cyclopropyl-2-[[2-methyl-4-(1 - methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one (A.1 .30), 1 -[3- (difluoromethoxy)-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl- tetrazol-5-one (A.1 .31 ), 1 -methyl-4-[3-methyl-2-[[2-methyl-4-(1 -methylpyrazol-3- yl)phenoxy]methyl]phenyl]tetrazol-5-one (A.1 .32), 1 -methyl-4-[3-methyl-2-[[1 -[3- (trifluoromethyl)phenyl]-ethylideneamino]oxymethyl]phenyl]tetrazol-5-one (A.1 .33), (Z,2E)-5-[\ - (2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-/V,3-dimethyl-pent-3-enamide (A.1.34), (^2 )-5-[1 -(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-/V,3-dimethyl-pent-3-enamide (A.1.35), (^2 )-5-[1 -(4-chloro-2-fluoro-phenyl)pyrazol-3-yl]oxy-2-methoxyimino-/V,3-dimethyl- pent-3-enamide (A.1.36),
inhibitors of complex III at Q, site: cyazofamid (A.2.1 ), amisulbrom (A.2.2), [(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9- dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acet- oxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl]
2-methylpropanoate (A.2.4), [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy- pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.5), [(3S,6S7R,8R)-8-benzyl-3-[[3-(1 ,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridine-2-car- bonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.6); (3S,6S,7R,8R)- 3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1 ,5- dioxonan-7-yl 2-methylpropanoate (A.2.7), (3S,6S,7R,8R)-8-benzyl-
3-[3-[(isobutyryloxy)methoxy]-4-methoxypicolinamido]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl isobutyrate (A.2.8);
inhibitors of complex II (e. g. carboxamides): benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18), N-(4'-trifluoromethylthiobiphenyl- 2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide (A.3.19), N-(2-(1 ,3,3-trimethyl- butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide (A.3.20), 3-(difluoromethyl)-1 - methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.21 ), 3-(trifluoromethyl)-1 - methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.22), 1 ,3-dimethyl-N-(1 ,1 ,3- trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.23), 3-(trifluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3- trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.24), 1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-4- yl)pyrazole-4-carboxamide (A.3.25), N-(7-fluoro-1 ,1 ,3-trimethyl-indan-4-yl)-1 ,3-dimethyl- pyrazole-4-carboxamide (A.3.26), N-[2-(2,4-dichlorophenyl)-2-methoxy-1 -methyl-ethyl]-3- (difluoromethyl)-l -methyl-pyrazole-4-carboxamide (A.3.27);
other respiration inhibitors (e. g. complex I, uncouplers): diflumetorim (A.4.1 ), (5,8- difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine (A.4.2); nitrophenyl derivates: binapacryl (A.4.3), dinobuton (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferimzone (A.4.7); organometal compounds: fentin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); and silthiofam
(A.4.12);
B) Sterol biosynthesis inhibitors (SBI fungicides)
C14 demethylase inhibitors (DMI fungicides): triazoles: azaconazole (B.1 .1 ), bitertanol (B.1 .2), bromuconazole (B.1.3), cyproconazole (B.1 .4), difenoconazole (B.1 .5), diniconazole (B.1 .6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1 .9), fluquinconazole (B.1 .10), flusilazole (B.1.1 1 ), flutriafol (B.1 .12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1 .15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1 .19), paclobutrazole (B.1 .20), penconazole (B.1 .21 ), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1 .24), tebuconazole (B.1 .25), tetraconazole (B.1.26), triadimefon (B.1 .27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1 .30), \ -\rel· (2^3 )-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1 H- [1 ,2,4]triazolo (B.1.31 ), 2-[reA(2^3 )-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]- 2H-[1 ,2,4]triazole-3-thiol (B.1 .32), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 -(1 ,2,4-triazol-1 - yl)pentan-2-ol (B.1 .33), 1 -[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -cyclopropyl-2-(1 ,2,4- triazol-1 -yl)ethanol (B.1 .34), 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 - yl)butan-2-ol (B.1.35), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1.36), 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1 -(1 ,2,4-triazol-1 -yl)butan- 2-o\ (B.1 .37), 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol (B.1.38), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1.39), 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 -yl)pentan-2-ol (B.1.40), 2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol (B.1.41 ), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1 ,2,4-triazol-1 -yl)pent-3-yn-2-ol (B.1 .51 ); imidazoles: imazalil (B.1 .42), pefurazoate (B.1.43), prochloraz (B.1 .44), triflumizol (B.1 .45); pyrimidines, pyridines and piperazines: fenarimol (B.1 .46), nuarimol (B.1 .47), pyrifenox (B.1.48), triforine (B.1 .49), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3- pyridyl)methanol (B.1 .50);
Delta14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph- acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8);
- Inhibitors of 3-keto reductase: fenhexamid (B.3.1 );
C) Nucleic acid synthesis inhibitors
phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (mefenoxam, C.1 .5), ofurace (C.1.6), oxadixyl (C.1.7);
- others: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate
(C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro- 2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7);
D) Inhibitors of cell division and cytoskeleton
tubulin inhibitors, such as benzimidazoles, thiophanates: benomyl (D1 .1 ), carbendazim (D1 .2), fuberidazole (D1 .3), thiabendazole (D1 .4), thiophanate-methyl (D1.5); triazolopyrimidines: 5-chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]tri- azolo[1 ,5-a]pyrimidine (D1 .6);
other cell division inhibitors: diethofencarb (D2.1 ), ethaboxam (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5), metrafenone (D2.6), pyriofenone (D2.7);
E) Inhibitors of amino acid and protein synthesis
methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil (E.1 .1 ), mepanipyrim (E.1.2), pyrimethanil (E.1 .3);
protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6), polyoxine (E.2.7), validamycin A (E.2.8);
F) Signal transduction inhibitors
MAP / histidine kinase inhibitors: fluoroimid (F.1 .1 ), iprodione (F.1 .2), procymidone (F.1 .3), vinclozolin (F.1.4), fenpiclonil (F.1 .5), fludioxonil (F.1 .6);
G protein inhibitors: quinoxyfen (F.2.1 );
G) Lipid and membrane synthesis inhibitors Phospholipid biosynthesis inhibitors: edifenphos (G.1.1 ), iprobenfos (G.1 .2), pyrazo- phos (G.1.3), isoprothiolane (G.1 .4);
lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos- methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
- phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph
(G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7) and N-(1 -(1 -(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4- fluorophenyl) ester (G.3.8);
compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 );
fatty acid amide hydrolase inhibitors: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1 -{[3,5-bis(di- fluoromethyl-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5- yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1 -{[3, 5-bis(difluoromethyl)-1 H-pyrazol-1 - yl]acetyl}piperidin-4-yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl
methanesulfonate (G.5.3);
H) Inhibitors with Multi Site Action
inorganic active substances: Bordeaux mixture (H.1.1 ), copper acetate (H.1 .2), copper hydroxide (H.1.3), copper oxychloride (H.1 .4), basic copper sulfate (H.1.5), sulfur (H.1 .6);
- thio- and dithiocarbamates: ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
organochlorine compounds (e. g. phthalimides, sulfamides, chloronitriles): anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 ), N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide (H.3.12);
guanidines and others: guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10);
I) Cell wall synthesis inhibitors
inhibitors of glucan synthesis: validamycin (1.1 .1 ), polyoxin B (1.1 .2);
melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5);
J) Plant defence inducers
acibenzolar-S-methyl (J.1.1 ), probenazole (J.1.2), isotianil (J.1 .3), tiadinil (J.1 .4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1 .6), fosetyl-aluminum (J.1 .7), phosphorous acid and its salts (J.1 .8), potassium or sodium bicarbonate (J.1.9);
K) Unknown mode of action
- bronopol (K.1 .1 ), chinomethionat (K.1.2), cyflufenamid (K.1 .3), cymoxanil (K.1 .4), dazomet (K.1 .5), debacarb (K.1.6), diclomezine (K.1 .7), difenzoquat (K.1 .8), difenzoquat- methylsulfate (K.1 .9), diphenylamin (K.1 .10), fenpyrazamine (K.1 .1 1 ), flumetover (K.1.12), flusulfamide (K.1 .13), flutianil (K.1 .14), methasulfocarb (K.1 .15), nitrapyrin (K.1 .16), nitrothal- isopropyl (K.1.18), oxathiapiprolin (K.1 .19), tolprocarb (K.1.20), oxin-copper (K.1 .21 ), proquinazid (K.1 .22), tebufloquin (K.1.23), tecloftalam (K.1 .24), triazoxide (K.1.25), 2-butoxy-6- iodo-3-propylchromen-4-one (K.1.26), 2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]-1 -[4-(4-{5-[2- (prop-2-yn-1 -yloxy)phenyl]-4,5-dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]ethanone (K.1.27), 2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]-1 -[4-(4-{5-[2-fluoro-6-(prop-2-yn-1 -yl- oxy)phenyl]-4,5-dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]ethanone (K.1 .28), 2-[3,5- bis(difluoromethyl)-1 H-pyrazol-1 -yl]-1 -[4-(4-{5-[2-chloro-6-(prop-2-yn-1 -yloxy)phenyl]-4,5- dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]ethanone (K.1.29), N-(cyclo- propylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide (K.1.30), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.31 ), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N- methyl formamidine (K.1.32), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)- phenyl)-N-ethyl-N-methyl formamidine (K.1.33), N'-(5-difluoromethyl-2-methyl-4-(3-tri- methylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.34), methoxy-acetic acid 6- tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester (K.1 .35), 3-[5-(4-methylphenyl)-2,3-dimethyl- isoxazolidin-3-yl]-pyridine (K.1 .36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]- pyridine (pyrisoxazole) (K.1.37), N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide (K.1.38), 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole (K.1 .39), 2-(4- chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide, ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), picarbutrazox (K.1.41 ), pentyl N-[6-[[(Z)- [(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .42), 2-[2- [(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (K.1 .43), 2-[2-fluoro-6-[(8- fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol (K.1 .44), 3-(5-fluoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinolin-1 -yl)quinoline (K.1 .45), 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1 - yl)quinoline (K.1.46), 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1 -yl)quinoline (K.1.47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1 ,4-benzoxazepine (K.1 .48).
The fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
The fungicides described by lUPAC nomenclature, their preparation and their pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197;
DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 1 1/028657, WO2012/168188, WO 2007/006670, WO 201 1/77514; WO13/047749, WO
10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/024010 and WO 13/047441 , WO 13/162072,
WO 13/092224, WO 1 1/135833).
The present invention is now illustrated in further details by the following examples, without imposing any limitation thereto.
The following abbreviations are used:
TFA: trifluoroacetic acid
EtOAc: ethyl acetate
HPLC: High Performance Liquid Chromatography
MS: Mass spectrometry
MeOH: Methanol
RT: Retention time
The Compound examples were characterized by coupled High Performance Liquid Chromatography with mass spectrometry (HPLC/MS) or by their melting point.
Method A: Analytical HPLC column 1 : RP-18 column Chromolith Speed ROD (from Merck KgaA, Germany). Elution: acetonitrile / water in a ratio of from 5:95 to 95:5 in 5 minutes at 40 °C.
Method B:
Analytical UPLC column: Phenomenex Kinetex 1 ,7 μηι XB-C18 100A; 50 x 2.1 mm; mobile phase: A: water; B: acetonitrile; gradient: 5-100% B in 1 .50 minutes; 100% B 0.20 min; flow: 0,8-1 ,0mL/min in 1 ,50 minutes at 60°C.
MS-method: ESI positive.
A. Preparation examples A.1 Preparation of amine compounds .1
Figure imgf000160_0001
1 -[(6-chloropyridin-3-yl)methyl]imidazolidin-2-imine was prepared in analogy to the method described in Journal of Agricultural and Food Chemistry, 56(17), 8023-8029; 2008 by reaction of imidacloprid with stannous(ll) chloride dihydrate A1.2 Preparation of amine compound E.2
Figure imgf000161_0001
The title compound was prepared by reduction of N-[3-[(2-chlorothiazol-5-yl)methyl]-5- methyl-1 ,3,5-oxadiazinan-4-ylidene]nitramide with iron. N-[3-[(2-chlorothiazol-5-yl)methyl]-5- methyl-1 ,3,5-oxadiazinan-4-ylidene]nitramide was obtained according to the method described in J. Agric. Food Chem. 2003, 51, 1823-1830.
The following amine compounds were prepared in analogy to methods described in literature.
Figure imgf000161_0002
Amine compounds not described herein can be prepared in analogy to the methods described herein.
A.2 Preparation of compounds I
Example 1 : Compound 1 -2 (compound of formula I, wherein R1 and R2 are H; Het is 6- chloropyridyl; -W1-W2-W3-W4- is -NH-CH2-CH2-; X1 is O; X2 is CN; and R3 and R5 together with the carbon atom to which they are attached form a cyclopropyl ring and m is 0
Figure imgf000162_0001
To the amine compound E1 (14.2 mmol) in dichloromethane (20 ml.) was added triethylamine (57.3 mmol) and 1 -cyanocyclopropanecarboxylic acid (18.9 mmol) at 0°C, and the mixture was stirred at room temperature for 5 min, before a solution of propylphosphonic anhydride (22.7 mmol, 50% by weight solution in ethyl acetate) was added. The mixture was allowed to reach room temperature over night. The reaction was then diluted with ethyl acetate (200 ml_), washed with saturated aqueous NaHCO3 (200 ml.) and water (200ml_). The layers were separated, and the organic layer dried over Na2S04 and concentrated in vacuo to afford a residue, which was purified using column chromatography over silica gel (0->30%
MeOH/EtOAc), followed by preparative HPLC to give the title compound.
H-NMR (CDCIs, 400 MHz): 1.49 (m, 2H), 1.58 (m, 2H), 3.44 (m, 2H), 3.65 (m, 2H), 4.61 (s, 2H), 7.35 (d, 1 H), 7.83 (m, 1 H), 8.27 (s, 1 H), 8.38 (s, 1 H) ppm.
By the method described above for example 1 , the following compound of formula Γ compiled in table 1 was prepared. Table 1 also shows physicochemical data for the compounds 1 -1 and 1 -2.
Figure imgf000162_0002
Table 1 :
Compound Het R3 R5 W RT [min] m/z [M+H]+ method Compound Het R3 R5 W RT [min] m/z [M+H]+ method
6-chloro-3-
1 -1 -CH2-CH2- S 2.391 321 .1 A
pyridyl
6-chloro-3-
1 -2 -CH2-CH2- NH 2.558 304.1 A
pyridyl
By the method described above for example 1 , the following compounds of formula I" compiled in table 2 were prepared. Table 2 also shows their physicochemical data
Figure imgf000163_0001
ComHet R3 R5 Rv5 Rv4 W RT m/z method pound [min] [M+H]+
6-chloro-3-
2-1 -CH2-CH2- H H S 0.930 319.0 B
pyridyl
6-chloro-3-
2-2 -CH2-CH2- H H NCHs 0.675 316.0 B
pyridyl
2-chloro-
2-3 -CH2-CH2- H H S 0.955 324.9 B
thiazol-5-yl
6-chloro-3-
2-4 -CH2-CH2- H H 0 0.809 302.9 B
pyridyl
6-chloro-3-
2-5 -CH2-CH2- CH3 H S 0.964 332.9 B
pyridyl
6-chloro-3-
2-6 -CH2-CH2- H CH3 S 1 .024 332.7 B
pyridyl
6-chloro-3-
2-7 -CH2-CH2- H CH2CH3 s 1 .093 347.1 B
pyridyl
6-chloro-3-
2-8 -CH2-CH2- CH3 CH3 s 1 .051 347.0 B
pyridyl
6-chloro-3-
2-9 -CH2-CH2- -CH2-CH2-CH2- s 1 .098 359.0 B
pyridyl
6-chloro-3-
2-10 -CH2-CH2- H CI s 1 .099 353.0 B
pyridyl
6-chloro-3-
2-1 1 -CH2-CH2- CF3 H s 1 .172 387.1 B
pyridyl
Figure imgf000164_0001
By the method described above for example 1 , the following compounds of formula Γ" compiled in table 3 were prepared. Table 3 also shows their physicochemical data
Figure imgf000164_0002
Table 3:
Figure imgf000164_0003
Biological exam
The biological activity of the compounds of formula I of the present invention may be evaluated in biological tests as described in the following.
General conditions: If not otherwise specified, most test solutions are to be prepared as follows:The active compound is to be dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water:acteon. Further, the test solutions are to be prepared at the day of use (and, if not otherwised specified, in general at concentrations wt/vol).
B.1 Green Peach Aphid (Myzus persicae)
For evaluating control of green peach aphid {Myzus persicae) through systemic means, the test unit consists of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.
The compounds are formulated using a solution containing 75% v/v water and 25% v/v
DMSO. Different concentrations of formulated compounds are pipetted into the aphid diet, using a custom built pipetter, at two replications. After application, 5 - 8 adult aphids are placed on the artificial membrane inside the microtiter plate wells. The aphids are then allowed to suck on the treated aphid diet and incubated at about 23 + 1 °C and about 50 + 5% relative humidity for 3 days. Aphid mortality and fecundity is then visually assessed.
In this test, compounds 1 -1 , 2-1 , 3-1 , 1-2, 2-2, 3-2, 2-3, 2-4, 2-5, 2-6, 2-7 at 2500 ppm showed at least 75 % mortality in comparison with untreated controls.
B.2 Vetch aphid {Megoura viciae)
For evaluating control of vetch aphid {Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at 2.5 μΙ, using a custom built micro atomizer, at two replications.
After application, the leaf disks were air-dried and 5 - 8 adult aphids were placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and were incubated at about 23 + 1 °C and about 50 + 5% relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed.
In this test, compounds 1 -1 , 2-1 , 1 -2, 2-2, 3-2, 2-3, 2-4, 2-5 at 2500 ppm showed at least 75 % mortality in comparison with untreated controls.
B.3 Cotton aphid {Aphis gossypii)
The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone. Surfactant (Alkamuls® EL 620) is added at a rate of 0.1 % (vol/vol). The test solution is prepared at the day of use.
Potted cowpea plants were colonized with approximately 50 - 100 aphids of various stages by manually transferring a leaf tissue cut from infested plant 24 hours before application. Plants were sprayed after the pest population has been recorded. Treated plants are
maintained on light carts at about 28°C. Percent mortality was assessed after 72 hours.
In this test, compounds 1 -2, 2-5 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.
B.4 Cowpea aphid {Aphis craccivora)
The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone. Surfactant (Alkamuls® EL 620) is added at a rate of 0.1 % (vol/vol). The test solution is prepared at the day of use. Potted cowpea plants are colonized with approximately 50 - 100 aphids of various stages by manually transferring a leaf tissue cut from infested plant 24 hours before application. Plants are sprayed after the pest population has been recorded. Treated plants are maintained on light carts at about 28°C. Percent mortality is assessed after 72 hours.
In this test, compounds 2-1 , 3-1 , 1-2, 2-2, 3-2, 2-4, 2-5 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.
B.5 Silverleaf whitefly (bemisia argentifolil) The active compounds are formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes are inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they serve as stock solutions for which lower dilutions are made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) is included in the solution at a volume of 0.01 % (v/v).
Cotton plants at the cotyledon stage (one plant per pot) are sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants are dried in the sprayer fume hood and then removed from the sprayer. Each pot is placed into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) are introduced. The insects are collected using an aspirator and a nontoxic Tygon® tubing connected to a barrier pipette tip. The tip, containing the collected insects, is then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups are covered with a reusable screened lid. Test plants are maintained in a growth room at about 25° C and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality is assessed 3 days after treatment, compared to untreated control plants.
In this test, compounds 1 -2, 3-2, 2-5, 2-7 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.
B.6 Orchid thrips (dichromothrips corbetti)
Dichromothrips corbetti a6u\\s used for bioassay are obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1 :1 mixture of acetone:water (vohvol), plus 0.01 % vol/vol Alkamuls® EL 620 surfactant.
Thrips potency of each compound is evaluated by using a floral-immersion technique. Plastic petri dishes are used as test arenas. All petals of individual, intact orchid flowers are dipped into treatment solution and allowed to dry. Treated flowers are placed into individual petri dishes along with about 20 adult thrips. The petri dishes are then covered with lids. All test arenas are held under continuous light and a temperature of about 28°C for duration of the assay. After 3 days, the numbers of live thrips are counted on each flower, and along inner walls of each petri dish. The percent mortality is recorded 72 hours after treatment.
In this test, compounds 2-1 , 1 -2, 3-2, 2-5 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.
B.7 Rice green leafhopper (Nephotettix virescens)
Rice seedlings are cleaned and washed 24 hours before spraying. The active compounds are formulated in 50:50 acetone:water (vohvol), and 0.1 % vol/vol surfactant (EL 620) is added. Potted rice seedlings are sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants are kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality is recorded after 72 hours.
In this test, compounds 2-1 , 1 -2 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.
B.8 Rice brown plant hopper (Nilaparvata lugens)
Rice seedlings are cleaned and washed 24 hours before spraying. The active compounds is formulated in 50:50 acetone:water (vohvol) and 0.1 % vol/vol surfactant (EL 620) was added. Potted rice seedlings are sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants are kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality is recorded after 72 hours.
In this test, compounds 1 -1 , 2-1 , 1 -2, 2-3 at 300 ppm showed at least 75 % mortality in comparison with untreated controls. B.9 Diamond back moth (Plutella xylostella)
The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : aceteone. Surfactant (Alkamuls® EL 620) is added at a rate of 0.1 %
(vol/vol). The test solution is prepared at the day of use.
Leaves of cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dish eslined with moist filter paper and inoculated with ten 3rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damages were also recorded using a scale of 0- 100%.
In this test, compound 1 -2 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.

Claims

Claims
1 . An N-acylimino compound of formula (I):
Figure imgf000168_0001
wherein m is an integer selected from 0, 1 , 2, 3, 4, 5 and 6; X1 is O or S; X2 is CN or N02;
Het is a 5- or 6-membered carbon-bound or nitrogen-bound heterocyclic or
heteroaromatic 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 R6, wherein k is an integer selected from 0, 1 , 2, 3 and 4;
W1 represents O, S or NRw1;
W2-W3-W4 represents a bivalent radical selected from -C(Rv2Rw2)-C(Rv3Rw3)-,
-C(Rv4)=C(Rv5)- and -C(Rv2Rw2)-0-C(Rv3Rw3)-;
Rw1 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 R7,
OR8, NR9aR9b, S(0)nR8, S(0)nNR9aR9b, C(=0)R7a, C(=0)NR9aR9b,
C(=0)OR8, C(=S)R7a, C(=S)NR9aR9b, C(=S)OR8, C(=S)SR8, C(=NR 7)R7a and C(=NR 7)NR9aR9 ; each Rv2, Rv3 independently from each other, are selected from the group
consisting of hydrogen, cyano, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-C10- 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 and/or may optionally be further substituted with 1 , 2 or 3 identical or different radicals R7; each Rv4, Rv5 are independently from each other selected from the group
consisting hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10- 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 R7, OR8, NR9aR9 , S(0)nR8, S(0)nNR9aR9 , C(=0)R7a, C(=0)NR9aR9 , C(=0)OR8, C(=S)R7a, C(=S)NR aR , C(=S)OR8, C(=S)SR8, C(=NR 7)R7a, C(=NR 7)NR9aR9 and Si(R11)2R12, or Rv4 and Rv5 may together be a C2-C5 alkylene chain forming a 4- to 7- membered unsaturated ring together with the carbon atoms atom Rv4 and Rv5 are bonded to and wherein the alkylene chain is unsubstituted or may carry any combination of 1 , 2, 3 or 4 identical or different radicals R7; each Rw2, Rw3 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 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 R7,
C(=0)R7a, C(=0)NR9aR9b, C(=0)OR8, C(=S)R7a, C(=S)NR9aR9b,
C(=S)OR8, C(=S)SR8, C(=NR 7)R7a and C(=NR 7)NR9aR9b,
R1, R2 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 and/or may carry any combination of 1 , 2 or 3 radicals R7,
Si(R11)2R12, OR8, OSO2R8, S(0)nR8, S(0)nNR9aR9b, NR9aR9 , C(=0)NR9aR9 , C(=S)NR aR , C(=0)OR8, C(=0)R7a, C(=S)R7a,
phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
R1 and R2 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 R7,
or
R and R2 may together be =0, =CR13R14, =S, =NR17, =NOR16 or =NNR9aR9 ;
R3 is selected from the group consisting of hydrogen, halogen, CN , Ci-C6-alkyl,
C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein each of the 4 last mentioned radicals are unsubstituted, partly or completely halogenated or carries 1 or 2 radicals R7, it being also possible for cycloalkyl to carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups, S(0)nNR9aR9b, NR9aR9b, C(=0)OR8, C(=0)NR9aR9b, C(=S)NR9aR9b, C(=0)R7a, C(=S)R7a, NR9a-C(=0)R7a, NR9a-C(=S)R7a, NR9a-S(0)nR8a,
phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
R4a, R4b are selected each independently from one another and independently from the integer of m from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio and Cs-Cs-cycloalkyl, wherein each of the four last mentioned radicals are unsubstituted, partly or completely halogenated, or
R4a and R4b may form together with the carbon atom they are bound to, a 3-, 4-, 5- or 6-membered aliphatic ring, wherein each of the carbon atoms of the ring may be unsubstituted or may be partly or fully halogenated, and/or may carry 1 , 2, 3, 4, 5 or 6 radicals selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy and Ci-C4-haloalkoxy;
or
R4a and R4 may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9 ,
R5 is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, 0-d-C6-alkyl, 0-C2-C6-alkenyl, O-C2- Ce-alkynyl, 0-C3-C8-cycloalkyl, S(0)n-Ci-C6-alkyl, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, S(0)n-C3-C8-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl parts of each of the 12 last mentioned radicals are
unsubstituted, partly or completely halogenated or carries 1 or 2 radicals R7, it being also possible for cycloalkyl radicals to carry 1 , 2, 3, 4, 5 or 6 Ci-C4-alkyl groups, S(0)nNR9aR9b, NR9aR9b, C(=0)OR8, C(=0)NR9aR9b, C(=S)NR9aR9b, C(=0)R7a, C(=S)R7a, 0-C(=0)OR8, 0-C(=0)NR9aR9 , 0-C(=S)NR9aR9 , 0-C(=0)R7a, O- C(=S)R7a, NR9a-C(=0)R7a, NR9a-C(=S)R7a, NR9a-S(0)nR8a, a moiety Q-phenyl, where the phenyl ring is optionally substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R10,
and a moiety Q-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, 4or 5 identical or different substituents R10, 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, O, S, S(O), S(0)2, NR9a, -0-S(=0)2-, -NR a-S(=0)2-, -0-C(=0)-, -NR a-C(=0)-, -0-Ci-C4-alkylene, -S-Ci-C4-alkylene, -S(0)-Ci-C4-alkylene, S(0)2-Ci-C4-alkylene, -NR9a-Ci-C4- alkylene, -0-C(=0)-Ci-C4-alkylene or
Figure imgf000172_0001
where the heteroatom in the last 7 moieties is bound to the carbon atom of C(X2)R3 or CR4aR4a, respectively; or, if m = 0, R3 and R5 together may also form with the carbon atom they are bound to, a 3-, 4-, 5- or
6-membered saturated partially unsaturated carbocycle or heterocyde, wherein the carbocycle or heterocyde may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, and where the heterocyde 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-R17c, or
R3 and R5 may together form where, independently of their occurrence, n is 0, 1 or 2; is selected from the group consisting of halogen, cyano, azido, nitro, SCN , SF5, Ci- Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be further substituted independently from one another with 1 , 2 or 3 radicals R7, OR8, N R17aR17b, S(0)nR8, S(0)nN R 7aR 7b, C(=0)R7a, C(=0)N R 7aR 7b, C(=0)OR8, C(=S)R7a, C(=S)N R 7aR 7b, C(=S)OR8, C(=S)SR8, C(=N R 7)R7a, C(=N R 7)N R 7aR 7 , Si(R1 1)2R12;
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents
R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R6 present on one ring carbon may together form =0, =CR13R14, =S, =N R17, =NOR16, =N N R9aR9b,
or two R6 together form a linear C2-C7 alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and N R17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=N R17; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6-haloalkynyl, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 radicals R10; independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN , SF5, Ci-Ce-alkyI, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Si(R11)2R12, OR8, OSO2R8, S(0)nR8, S(0)nNR 7aR 7b, NR17aR17b, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, C(=0)OR8, C(=0)R15, C(=S)R15, C(=NR 7)R15,
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 R10, 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two R7 present on one carbon atom may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b,
or two R7 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 R7 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 R10; 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, C3-Cio-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
R7b is selected from the group consisting of halogen, cyano, Ci-Cio-alkyl, C3-C10- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Cs-Cs-cycloalkenyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be partly or completely halogenated, and/or be substituted with 1 , 2,3 or 4, in particular 1 , 2 or 3, identical or different radicals R7,
OR8, NR17aR17b, S(0)nR8, S(0)nNR 7aR 7b, C(=0)R7a, C(=0)NR 7aR 7b, C(=0)OR8, C(=S)R7a, C(=S)NR 7aR 7b, C(=S)OR8, C(=NR 7)R7a, C(=NR 7)NR 7aR 7 , Si(R11)2R12 phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R7b present on one ring carbon may together form =0, =S or =CR13R14, or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and NR17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=NR17; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 radicals R10; independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, C(=0)R15, C(=0)N R 7aR 7 , C(=S)N R 7aR 7 , C(=0)OR16, 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 R10, 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 R10, 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 Ci-C6-alkyl, Cs-Cs-cycloalkyI, C3-C8-cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the five last mentioned radicals are unsubstituted, partly or completely halogenated,
phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or may be substituted with one or more, e.g. 1 , 2, 3, 4 or 5 identical or different substituents R10,
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
R9b 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-cycloalkyI, Cs-Cs-halocycloalkyl, C3- C8-cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6 haloalkynyl,
S(0)nR16, -S(0)nNR 7aR 7 , C(=0)R15, C(=0)OR16, C(=0)NR 7aR 7 , C(=S)R15, C(=S)SR16, C(=S)NR 7aR 7b, C(=NR 7)R15;
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 R10; and
a 3-, 4-, 5-, 6- or 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or,
R9a and R9b 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, Ci- Ce-alkyl, Ci-C6-haloalkyl, Ci-Ce-alkoxy, d-C6-haloalkoxy, Ci-C6-alkylthio, Ci-
C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or
R9a and R9b together may form =CR13R14, =NR17, =NOR16, =NNR17aR17b moiety; independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, 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 R10a,
Si(R11)2R12, OR16, OS(0)nR16, -S(0)nR16, S(0)nNR 7aR 7b, NR17aR17b, C(=0)R15, C(=S)R15, C(=0)OR16, -C(=NR 7)R15, C(=0)NR 7aR 7 , C(=S)NR 7aR 7 ,
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; or
two R10 present together on one carbon ring atom of a saturated or partly unsaturated heterocyclic radical may form =0, =CR13R14, =S, =NR17, =NOR16,
=NNR17aR17b;
or,
two R10 on adjacent carbon ring atoms may also be a bivalent radical selected from CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH,
OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2NR17, CH2CH=N, CH=CH-NR17, OCH=N, SCH=N and form together with the carbon atoms to which the two R10 are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3, OCH3, halogen, cyano, halomethyl and halomethoxy;
R10a independently of its occurrence, is selected from the group consisting of halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl,
Si(R11)2R12, OR16, OS(0)nR16, -S(0)nR16, S(0)nNR 7aR 7b, NR17aR17b, C(=0)R15, C(=S)R15, C(=0)OR16, -C(=NR 7)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7 ,
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; R11, R12 independently of their occurrence, are selected from the group consisting of
Ci-Ce-alkyI, Ci-Ce-haloalkyI, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-Cs-halocycloalkyl-Ci-C4- alkyl, Ci-C6-haloalkoxy-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals are unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, cyano, NO2, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy-Ci-C4- alkyl, phenyl and benzyl; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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; 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,
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; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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, 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,
R17a, R17b 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, te/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four 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,
or,
R17a and R17b 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 R17a and R17b 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-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
R17a and R17b together may form =CR13R14, =NR17 or =NOR16 moiety;
R17c independently of its occurrence, is selected from the group consisting of hydrogen, CN, d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci- C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry
1 or 2 radicals selected from 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; the stereoisomers, tautomers and the salts thereof.
2. The compound of claim 1 , wherein
Het is selected from the group consisting of radicals of the following formula Het-1 to Het-24:
Figure imgf000181_0001
Het-2 Het-3 Het-4 Het-5
Figure imgf000181_0002
Het-6 Het-7 Het-8 Het-9 Het-10
Figure imgf000181_0003
Het-11 Het-12 Het-13 Het-14 Het-15
Figure imgf000181_0004
Het-16 Het-17 Het-18 Het-19 Het-20
Figure imgf000181_0005
Het-21 Het-22 Het-23 Het-24 wherein # denotes the bond to the remainder of the molecule in formula (I), and wherein k is 0, 1 or 2; and R6a is hydrogen or has one of the meanings given for R6; and
R6b is hydrogen, Ci-C4-alkyl or Ci-C4-haloalkyl.
The compound of claim 2, wherein
Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24
Figure imgf000182_0001
Het-1 Het-11a Het-24
wherein # denotes the bond to the remainder of the molecule in formula (I), and wherein R6 is selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and C1-C4- haloalkyl;
R6a is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and
Ci-C4-haloalkyl; and
k is 0, 1 or 2.
The com ound of claim 3, wherein Het is Het-1 a
Figure imgf000182_0002
Het-1 a
wherein # denotes the bond to the remainder of the molecule in formula (I),
R6 is selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl; and
R6a is hydrogen or halogen, in particular hydrogen.
The compound of any of the preceding claims, wherein
R1 , R2 are independently from each other selected from the group consisting of hydrogen, halogen, CN , Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, C3-C6- halocycloalkyl;
or
R1 and R2 may together be =CR13R14; or
R1 and R2 form, together with the carbon atom, which they attached to, a 3- to 5-membered saturated carbocyclic ring.
The compound of claim 5, wherein both R1 and R2 are hydrogen.
The compound of any of the preceding claims, wherein
R3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, d-Ce-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, NR9aR9b and
NR9a-C(=0)R7a.
8. The compound of claim 7, wherein
R3 is selected from the group consisting of hydrogen, fluorine, chlorine, d-d- alkyl, NHC(=0)-Ci-C4-alkyl and CN.
9. The compound of any of the preceding claims, wherein m is 0 or 1.
The compounds of any of the preceding claims, wherein
m is 1 , and
R4a, R4b are selected independently from one another from hydrogen, methyl and halogen or R4a and R4b together are =0.
The compound of any of the preceding claims, wherein
R5 is hydrogen, halogen, NR9aR9b, Ci-C6-alkyl, d-d-haloalkyl, S-Ci-C6-alkyl, S-
Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, S-C3-C6-cycloalkyl, S- Cs-Ce-halocycloalkyl, C(=0)OR8, C(=0)NR aR , C(=S)NR aR , C(=0)R7a, C(=S)R7a, Q-phenyl, where phenyl is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or Q-Het#, where Het# is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
and where Q, irrespectively of its occurrence, is a single bond, S, NR9a, NR a-C(=0), OC(=0), NR aCH2, OC(=0)CH2, or NR aC(=0)CH2.
12. The compound of any of the preceding claims, wherein
R5 is hydrogen, halogen, d-d-alkyl, d-d-haloalkyl, S-d-d-alkyl, S-d-Ce- haloalkyl, d-d-cycloalkyl, d-d-halocycloalkyl, S-d-d-cycloalkyl, S-d-d- halocycloalkyl, phenyl and and S-phenyl, where the phenyl ring in the last to radicals is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different substituents R10.
The compound of any of claims 1 to 9, wherein m is 0, and
R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated carbocyle, wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, or
R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated heterocycle having 1 or 2 non adjacent heteroatoms as ring members which are selected from O and S, wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b,
wherein
R7b is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-alkoxy, and C2-C6-alkynyl, and wherein the carbon atoms of the aforementioned aliphatic radicals may optionally be partly or completely halogenated and/or substituted by 1 or 2 radicals R7, and wherein one or two radicals R7b may also be
C3-C6-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals selected from fluorine, chlorine or methyl,
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, or
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 R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R7b present on one ring carbon may together form =0 or =S, or two R7b together form a linear C2-C7 alkylene chain, thus forming, together with the carbon atom to which they are bound, a 3-, 4-, 5- or 6-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O and S, and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy,
wherein
R7 is selected from Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, C1-C4- alkylcarbonyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C3-C8- cycloalkyl, Cs-Cs-cycloalkoxy, phenyl, phenoxy, 5- or 6-membered saturated heterocyclyl having 1 heteroatom selected from O and S, and 5- or 6-membered hetaryl having 1 or 2 heteroatoms selected from O, S and N as ring memberes, where 5- or 6-membered saturated
heterocyclyl and 5- or 6-mbered hetaryl may be unsubstituted or carry 1 or 2 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, and Ci-C4-haloalkoxy;
R10 is selected from the group consisting of halogen, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
4. The compound of any claim 13, wherein
R3 and R5 together with the carbon atom, to which they are bound, form a 3- or 4- membered saturated carbocyle, wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b,
wherein
R7b is selected from the group consisting of halogen, Ci-C4-alkyl, and wherein one radical R7b may also be
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, where
R10 is selected from the group consisting of halogen, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
5. The compounds of any of the receding claims, wherein the moiety of the formula (W.Het)
(W.Het)
Figure imgf000185_0001
represents a radical selected from the group consisting of W.Het-1 , W.Het-2,W.Het-2a, W.Het-3 W.Het-4 and W.Het-5:
Figure imgf000186_0001
W.Het-3 W.Het-4 W.Het-5 wherein # denotes the bond to the remainder of the molecule; X1, R1, R2 and Het are as defined in any of claims 1 to 6, and wherein
Rw1 is as defined in claim 1 and in particular selected from hydrogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4- alkylcarbonyl and Ci-C4-haloalkylcarbonyl; and
each Rv4, Rv5 are as defined in claim 1 and in particular are independently from each other selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl and Ci- C4-haloalkyl, wherein at least one of the radicals Rv4 or Rv5 is different from hydrogen; or
Rv4 and Rv5 may together be a C2-C4 alkylene chain forming a 4- to 6-membered unsaturated ring together with the carbon atoms atom Rv4 and Rv5 are bonded to.
16. The compound of claim 15, wherein the radical W.Het is selected from the group
consisting of W.Het-1 , W.Het-2, W.Het-2a and W.Het-6.
17. The compound of claim 15, wherein the radical W.Het is selected from the group
consisting of W.Het-3, W.Het-4 and W.Het-5, wherein Rw1 is hydrogen, methyl or ethyl.
8. The compound of claims 15, 16 or 17, wherein Het is selected from the group consisting of radicals of formulae Het-1 Het-1 1 a and Het-24,
Figure imgf000187_0001
Het-1 Het-11a Het-24
wherein # denotes the bond to the remainder of the molecule in formula (I), and wherein R6 is selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and d-d- haloalkyl;
R6a is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and
Ci-C4-haloalkyl; and
k is 0, 1 or 2.
9. The compound of any of claims 15 to 18, wherein
m is 0 or 1 ;
both R1 and R2 are hydrogen;
R3 is selected from the group consisting of hydrogen, fluorine, chlorine, d-d- alkyl, N HC(=0)-Ci-C4-alkyl and CN;
R5 is hydrogen, halogen, d-d-alkyl, d-d-haloalkyl, S-d-d-alkyl, S-d-Ce- haloalkyl, d-d-cycloalkyl, d-d-halocycloalkyl, S-d-d-cycloalkyl, S-d-d- halocycloalkyl, phenyl and and S-phenyl, where the phenyl ring in the last to radicals is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different substituents R10;
if m is 1 ,
R4a, R4b are each hydrogen, or
if m is 0,
R3 and R5 together with the carbon atom, to which they are bound, form a 3- or 4- membered saturated carbocyle, wherein the carbocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, or
R3 and R5 together with the carbon atom, to which they are bound, form a 3-, 4-, 5- or 6- membered saturated heterocycle having 1 or 2 non adjacent heteroatoms as ring members which are selected from O and S, wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4, 5 or 6 radicals R7b, R7b is selected from the group consisting of halogen, Ci-C4-alkyl, and wherein one radical R7b may also be
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, where
R10 is selected from the group consisting of halogen, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
The compound of claim 15, wherein R1 and R2 are hydrogen, m is 0 and wherein the moiety W.Het, Het, X1 , X2, R3 and R5 are as defined in one of the rows of the following table:
W. Het Het X1 X2 R3 R5
W.Het-1 6-chloro-3-pyridyl 0 CN -CH2-CH2-
W.Het-1 6-chloro-3-pyridyl S CN -CH2-CH2-
W.Het-1 2-chloro-5-thiazolyl 0 CN -CH2-CH2-
W.Het-1 2-chloro-5-thiazolyl s CN -CH2-CH2-
W.Het-1 3-tetrahydrofuryl 0 CN -CH2-CH2-
W.Het-1 3-tetrahydrofuryl s CN -CH2-CH2-
W.Het-2 6-chloro-3-pyridyl 0 CN -CH2-CH2-
W.Het-2 6-chloro-3-pyridyl s CN -CH2-CH2-
W.Het-2 2-chloro-5-thiazolyl 0 CN -CH2-CH2- 0 W.Het-2 2-chloro-5-thiazolyl s CN -CH2-CH2- 1 W.Het-2 3-tetrahydrofuryl 0 CN -CH2-CH2- 2 W.Het-2 3-tetrahydrofuryl s CN -CH2-CH2- 3 W.Het-3, Rw1 = H 6-chloro-3-pyridyl 0 CN -CH2-CH2- 4 W.Het-3, Rw1 = H 6-chloro-3-pyridyl s CN -CH2-CH2- 5 W.Het-3, Rw1 = H 2-chloro-5-thiazolyl 0 CN -CH2-CH2- 6 W.Het-3, Rw1 = H 2-chloro-5-thiazolyl s CN -CH2-CH2- 7 W.Het-3, Rw1 = H 3-tetrahydrofuryl 0 CN -CH2-CH2- 8 W.Het-3, Rw1 = H 3-tetrahydrofuryl s CN -CH2-CH2- 9 W.Het-4, Rw = H 6-chloro-3-pyridyl 0 CN -CH2-CH2- 0 W.Het-4, Rw = H 6-chloro-3-pyridyl s CN -CH2-CH2- 1 W.Het-4, Rw = H 2-chloro-5-thiazolyl 0 CN -CH2-CH2- 2 W.Het-4, Rw = H 2-chloro-5-thiazolyl s CN -CH2-CH2- 3 W.Het-4, Rw = H 3-tetrahydrofuryl 0 CN -CH2-CH2- W. Het Het X1 X2 R3 R5
W.Het-4, Rw = H 3-tetrahydrofuryl S CN -CH2-CH2-
W.Het-5, Rw1 = H 6-chloro-3-pyridyl 0 CN -CH2-CH2-
W.Het-5, Rw1 = H 6-chloro-3-pyridyl S CN -CH2-CH2-
W.Het-5, Rw1 = H 2-chloro-5-thiazolyl 0 CN -CH2-CH2-
W.Het-5, Rw1 = H 2-chloro-5-thiazolyl s CN -CH2-CH2-
W.Het-5, Rw1 = H 3-tetrahydrofuryl 0 CN -CH2-CH2-
W.Het-5, Rw1 = H 3-tetrahydrofuryl s CN -CH2-CH2-
W.Het-5, Rw1 = CH3 6-chloro-3-pyridyl 0 CN -CH2-CH2-
W.Het-5, Rw1 = CH3 6-chloro-3-pyridyl s CN -CH2-CH2-
W.Het-5, Rw1 = CH3 2-chloro-5-thiazolyl 0 CN -CH2-CH2-
W.Het-5, Rw1 = CH3 2-chloro-5-thiazolyl s CN -CH2-CH2-
W.Het-5, Rw1 = CH3 3-tetrahydrofuryl 0 CN -CH2-CH2-
W.Het-5, Rw1 = CH3 3-tetrahydrofuryl s CN -CH2-CH2-
W.Het-1 6-chloro-3-pyridyl 0 N02 H S-CF3
W.Het-1 6-chloro-3-pyridyl s N02 H S-CF3
W.Het-1 2-chloro-5-thiazolyl 0 N02 H S-CF3
W.Het-1 2-chloro-5-thiazolyl s N02 H S-CF3
W.Het-1 3-tetrahydrofuryl 0 N02 H S-CF3
W.Het-1 3-tetrahydrofuryl s N02 H S-CF3
W.Het-2 6-chloro-3-pyridyl 0 N02 H S-CF3
W.Het-2 6-chloro-3-pyridyl s N02 H S-CF3
W.Het-2 2-chloro-5-thiazolyl 0 N02 H S-CF3
W.Het-2 2-chloro-5-thiazolyl s N02 H S-CF3
W.Het-2 3-tetrahydrofuryl 0 N02 H S-CF3
W.Het-2 3-tetrahydrofuryl s N02 H S-CF3
W.Het-3, Rw1 = H 6-chloro-3-pyridyl 0 N02 H S-CF3
W.Het-3, Rw1 = H 6-chloro-3-pyridyl s N02 H S-CF3
W.Het-3, Rw1 = H 2-chloro-5-thiazolyl 0 N02 H S-CF3
W.Het-3, Rw1 = H 2-chloro-5-thiazolyl s N02 H S-CF3 W. Het Het X1 X2 R3 R5
W.Het-3, Rw1 = H 3-tetrahydrofuryl 0 N02 H S-CF3
W.Het-3, Rw1 = H 3-tetrahydrofuryl S N02 H S-CF3
W.Het-4, Rw = H 6-chloro-3-pyridyl 0 N02 H S-CF3
W.Het-4, Rw = H 6-chloro-3-pyridyl s N02 H S-CF3
W.Het-4, Rw = H 2-chloro-5-thiazolyl 0 N02 H S-CF3
W.Het-4, Rw = H 2-chloro-5-thiazolyl s N02 H S-CF3
W.Het-4, Rw = H 3-tetrahydrofuryl 0 N02 H S-CF3
W.Het-4, Rw = H 3-tetrahydrofuryl s N02 H S-CF3
W.Het-5, Rw1 = H 6-chloro-3-pyridyl 0 N02 H S-CF3
W.Het-5, Rw1 = H 6-chloro-3-pyridyl s N02 H S-CF3
W.Het-5, Rw1 = H 2-chloro-5-thiazolyl 0 N02 H S-CF3
W.Het-5, Rw1 = H 2-chloro-5-thiazolyl s N02 H S-CF3
W.Het-5, Rw1 = H 3-tetrahydrofuryl 0 N02 H S-CF3
W.Het-5, Rw1 = H 3-tetrahydrofuryl s N02 H S-CF3
W.Het-5, Rw1 = CH3 6-chloro-3-pyridyl 0 N02 H S-CF3
W.Het-5, Rw1 = CH3 6-chloro-3-pyridyl s N02 H S-CF3
W.Het-5, Rw1 = CH3 2-chloro-5-thiazolyl 0 N02 H S-CF3
W.Het-5, Rw1 = CH3 2-chloro-5-thiazolyl s N02 H S-CF3
W.Het-5, Rw1 = CH3 3-tetrahydrofuryl 0 N02 H S-CF3
W.Het-5, Rw1 = CH3 3-tetrahydrofuryl s N02 H S-CF3
W.Het-4, Rw =CH3 6-chloro-3-pyridyl 0 CN -CH2-CH2-
W.Het-6 6-chloro-3-pyridyl 0 CN -CH2-CH2-
W.Het-2a, 0 CN -CH2-CH2-
6-chloro-3-pyridyl
Rv4 = H, Rv5 = CH3
W.Het-2a, 0 CN -CH2-CH2-
6-chloro-3-pyridyl
Rv4 = CH3, Rv5 = H
W.Het-2a, 0 CN -CH2-CH2-
6-chloro-3-pyridyl
Rv4 = C2H5, Rv5 = H W. Het Het X1 X2 R3 R5
78 W.Het-2a, 0 CN -CH2-CH2-
6-chloro-3-pyridyl
Rv4 = CH3, Rv5 = CH3
79 W.Het-2a, Rv4 and 0 CN -CH2-CH2- Rv5form together 6-chloro-3-pyridyl
Figure imgf000191_0001
80 W.Het-2a, 0 CN -CH2-CH2-
6-chloro-3-pyridyl
Rv4 = Rv5 = H
81 W.Het-2a, 0 CN -CH2-CH2-
6-chloro-3-pyridyl
Rv4 = H, Rv5 = CF3
82 W.Het-2 6-chloro-3-pyridyl 0 CN H H
21 . The compound of any of the preceding claims, wherein
X1 is O.
22. The compound of any of the preceding claims, wherein
X2 is CN.
23. An agricultural or veterinary composition for combating animal pests comprising at least one compound as defined in any of claims 1 to 22 and at least one inert liquid and/or solid acceptable carrier and optionally, if desired, at least one surfactant.
24. The use of a compound as defined in any of claims 1 to 22 for combating or controlling invertebrate pests, for protecting growing plants from attack or infestation by invertebrate pests, for protecting plant propagation material, especially seeds, from soil insects, or for protect the seedlings roots and shoots of plants from soil and foliar insects.
25. A method for combating or controlling invertebrate pests, which method comprises
contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound as defined in any one of claims 1 to 22.
26. A method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound as defined in any of claims 1 to 22. A method for the protection of plant propagation material, especially seeds, from soil insects and of the seedlings roots and shoots from soil and foliar insects comprising contacting the plant propagation material before sowing and/or after pregermination with at least one compound as defined in any one of claims 1 to 22.
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 parasiticidally effective amount of a compound as defined in any of claims 1 to 22.
29. The compound as defined in any of claims 1 to 22 for the use in the treatment animals infested or infected by parasites, for preventing animals of getting infected or infested by parasites or for protecting animals against infestation or infection by parasites.
PCT/EP2015/074196 2014-10-20 2015-10-20 N-acylimino heterocyclic compounds WO2016062678A1 (en)

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CN110301436A (en) * 2019-08-13 2019-10-08 福建拓烯新材料科技有限公司 A kind of microcapsule formulations composition and preparation method thereof
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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EP2305658A1 (en) * 2008-07-01 2011-04-06 Meiji Seika Kaisha, Ltd. Novel imino derivative, process for production of the same, and pesticide comprising the same
EP2591673A1 (en) * 2010-07-07 2013-05-15 Meiji Seika Pharma Co., Ltd. Pest control agent
EP2633756A1 (en) * 2012-02-29 2013-09-04 Meiji Seika Pharma Co., Ltd. Pest control composition including novel iminopyridine derivate

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EP2305658A1 (en) * 2008-07-01 2011-04-06 Meiji Seika Kaisha, Ltd. Novel imino derivative, process for production of the same, and pesticide comprising the same
EP2591673A1 (en) * 2010-07-07 2013-05-15 Meiji Seika Pharma Co., Ltd. Pest control agent
EP2633756A1 (en) * 2012-02-29 2013-09-04 Meiji Seika Pharma Co., Ltd. Pest control composition including novel iminopyridine derivate

Cited By (3)

* Cited by examiner, † Cited by third party
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
CN110301436A (en) * 2019-08-13 2019-10-08 福建拓烯新材料科技有限公司 A kind of microcapsule formulations composition and preparation method thereof

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