Classifications

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  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/81—Amides; Imides
  • C07D213/82—Amides; Imides in position 3
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/56—Amides
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • A—HUMAN NECESSITIES
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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  • 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
  • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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  • 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
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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  • 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
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  • 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
  • A01N43/82—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 three ring hetero atoms
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  • 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
  • A01N43/84—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
• • A—HUMAN NECESSITIES
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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
  • A01N47/14—Di-thio analogues thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
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• • C—CHEMISTRY; METALLURGY
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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  • 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
  • C07D401/12—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 chain containing hetero atoms as chain links
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  • 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
  • C07D405/12—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 chain containing hetero atoms as chain links
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  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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  • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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  • C07D417/12—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 chain containing hetero atoms as chain links

Definitions

• Alkynyl optionally substituted (C 3 -C 0 ) cycloalkyl, optionally substituted (C -C 0 ) cycloalkenyl, optionally substituted aryl or optionally substituted heterocyclyl;
• R 8 is substituted (-C-C 10 ) -alkyl, optionally substituted (C3-C 1 0) -alkenyl, optionally substituted (C 3 -C ⁇ o) -alkynyl, optionally substituted (C 3 -C ⁇ 0 ) -cycloalkyl, optionally substituted (C -C- ⁇ o) cycloalkenyl, optionally substituted aryl,
• R 9 is substituted (-C-C ⁇ o) alkyl, optionally substituted (C 3 -C 10 ) -
• R 10 is hydrogen, optionally substituted (C ⁇ C ⁇ o) alkyl, optionally substituted (C 3 -C ⁇ o) alkenyl, optionally substituted (C3-C 10 ) alkynyl, optionally substituted (C 3 -C 10 ) cycloalkyl, optionally substituted ( C 4 -C 10 -cycloalkenyl, optionally substituted aryl or optionally substituted
• Atoms optionally contains a heteroatom unit, such as oxygen, sulfur, S (O), S (O) 2 or NR 29 , in the case of oxygen optionally also two not immediately adjacent oxygen atoms, or which may also be benzo-condensed;
• a heteroatom unit such as oxygen, sulfur, S (O), S (O) 2 or NR 29 , in the case of oxygen optionally also two not immediately adjacent oxygen atoms, or which may also be benzo-condensed;
• R 13 is hydrogen, optionally substituted (-C-C ⁇ 0 ) alkyl, optionally substituted (C 3 -C ⁇ o) alkenyl, optionally substituted (C 3 -C ⁇ o) alkynyl, optionally substituted (C 3 -C1 0 ) - cycloalkyl, optionally substituted (C 4 -C ⁇ o) cycloalkenyl, optionally substituted aryl, optionally substituted
• Heterocyclyl optionally substituted (-C 10 -C) alkanoyl, optionally substituted (C 3 -C 10) alkenoyl, optionally substituted (C 3 -C ⁇ o) alkynoyl, optionally substituted (C 4 -C 10 ) - cycloalkanoyl, optionally substituted aroyl, optionally substituted heterocyclylcarbonyl, carbamoyl, optionally substituted mono- or di- (C ⁇ -C- ⁇ o) alkylcarbamoyl, the latter The rest optionally cyclically linked and optionally one
• Heteroatom unit such as oxygen, sulfur, S (O), S (O) 2 or NR 29 , containing, optionally substituted mono- or di- (C 3 -C ⁇ o) - cycloalkylcarbamoyl, optionally substituted aryl or optionally substituted N-aryl- N-C ⁇ -C ⁇ 0 -alkylcarbamoyI, optionally substituted (C ⁇ -C- ⁇ o) alkoxycarbonyl, optionally substituted (C 3 -C ⁇ 0 ) -alkenyloxycarbonyl, optionally substituted (C 3 -C ⁇ o) alkynyloxycarbonyl, optionally substituted (C 3 -C ⁇ 0 ) -Cycloalkoxycarbonyl, optionally substituted aryloxycarbonyl, optionally substituted heterocyciyloxycarbonyl, optionally substituted (C 1 -C 10 ) -
• Cycloalkoxycarbonyl optionally substituted aryloxycarbonyl, optionally substituted heterocyclyloxycarbonyl, the thiocarbonyl analogs of the aforementioned carbonyl derivatives, optionally substituted (-CC 10 ) -alkylsulfonyl, optionally substituted arylsulfonyl or optionally substituted
• R 18 , R 19 , R 20 are the same or different and each have the meaning of R 10 , or are linked together to form a 3-8-membered ring which optionally contains a heteroatom unit, such as oxygen, sulfur, S (O), S (O) 2 , or NR 29 , contains or R 18 and / or R 19 are optionally substituted (-C-C- ⁇ o) alkanoyl, optionally substituted (C 3 -C ⁇ 0 ) alkenoyl, optionally substituted (C 3 -C 10 ) - Alkinoyl, optionally substituted (C 4 -C ⁇ o) cycloalkanoyl, optionally substituted aroyl, optionally substituted heterocyclylcarbonyl, carbamoyl, optionally substituted mono- or di- (-C-C ⁇ o) alkylcarbamoyl, the latter radical also cyclically linked and optionally a heteroatom unit , such as oxygen,
• Cycloalkoxycarbonyl optionally substituted aryloxycarbonyl, optionally substituted heterocyclyloxycarbonyl, optionally substituted (C ⁇ -C ⁇ o) alkylsulfonyl, optionally substituted arylsulfonyl, optionally substituted heterocyclylsulfonyl, optionally substituted aroyl or optionally substituted
• R 23 and R 24 are the same or different and each have the meaning of R 13 or are linked together to form a 3-8-membered ring;
• R 26 is optionally substituted (C 4 -C 0 ) cycloalkenyl or substituted (C 3 -C 0 ) cycloalkyl.
• Y is preferably O.
• n is preferably 0.
• R 1 is preferably substituted one or more times by F and / or Cl
• (-C-C 4 ) alkyl in particular CF 3 , CHF 2 or CF 2 CI.
• R 2 , R 3 are preferably hydrogen.
• R 4 is preferably hydrogen or (C 1 -C) alkyl.
• G 1 is preferably an unbranched or branched (C 2 -C 4 ) alkylene unit for which between the amide nitrogen and the second
• G 2 is preferably an unbranched or branched (C- ⁇ -C 4 ) -
• Y is O.
• n is O.
• R 4 is hydrogen or methyl.
• G 1 is CH 2 -CH 2 , CH 2 -CH 2 -CH 2 , CH (CH 3 ) -CH 2 or CH (C 2 H 5 ) -CH 2 .
• R 7 is preferably (-C 8 ) alkyl, (CrC 4 ) - fluoroalkyl, with optionally substituted phenyl, furyl, thienyl or with (C 3 -C 6 ) - Cycloalkyl substituted (-C-C 4 ) alkyl, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) haloalkenyl, (C 3 - C 6 ) alkynyl, (C 3 - C 6 ) -cycloalkyl or optionally substituted phenyl or heteroaryl, in particular fluorine, chlorine, methyl, trifluoromethyl and methoxy are preferred as substituents on the phenyl or heteroaryl group and heteroaryl is preferably thienyl, pyridyl, pyrimidyl, thiazolyl, benzothiazolyl, imidazolyl
• R 9 is preferably (CrC ⁇ fluoroalkyl, (C 3 - C 6) alkenyl, (C 3 -C 6) -alkynyl or (C 3 -C 6) cycloalkyl.
• R 14 and R 15 are preferably hydrogen, (-C 8 -C) alkyl, (C 3 -C 6 ) cycloalkyl, optionally by fluorine, chlorine , Methyl, methoxy or trifluoromethyl-substituted phenyl or pyridyl or R 14 and R 15 are linked to form a 4-6-membered carbocyclic ring.
• R 12 is preferably hydrogen or (C 1 -C 4 ) alkyl, preferably methyl
• R 16 is preferably hydrogen or (C 1 -C 4) -Alkyl, preferably methyl and R 17, preferably phenyl or pyridyl optionally substituted by chlorine and / or trifluoromethyl, (C 1 -C 8 ) -alkanoyl, (C 4 -C 7 ) -cycloalkanoyl, optionally by fluorine, chlorine, methyl, methoxy or Trifluoromethyl substituted aroyl, pyridylcarbonyl, furoyl, carbamoyl, mono- or di- (-C-C 4 ) alkylcarbamoyl, (-C-C 4 ) alkoxycarbonyl, or the thiocarbonyl analogues of the aforementioned carbonyl derivatives.
• R 10 is preferably hydrogen or (C 1 -C 4 ) alkyl and R 12 is preferably (C 1 -C 8 ) - Alkyl or (C 5 -C 6 ) cycloalkyl.
• R 26 is preferably fluoro (C 3 -C 6 ) cycloalkyl or (-C-C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl.
• (C 2 -C 6 ) alkylene unit includes, for example, the groups (CH 2 ) 2 , CH (CH 3 ), (CH 2 ) 3 , (CH 2 ) 4 , CH (CH 3 ) CH 2 , CH (C 2 H 5 ), CH 2 CH (CH 3 ), CH 2 CH (CH 3 ) CH 2 , CH (CH 3 ) CH 2 CH 2 and CH 2 CH 2 CH (CH 3 ), (CH 2 ) 5 , CH 2 C (CH 3 ) 2 CH 2 or (CH 2 ) 6 .
• the term "(-C-C 6 ) alkylene unit” includes the above groups and the methylene group.
• halogen includes fluorine, chlorine, bromine and iodine.
• (0, -C) alkyl is an unbranched or branched hydrocarbon radical with 1,
• an unbranched or branched saturated is under an alkyl radical with a larger range of carbon atoms
• alkenyl and "Alkynyl” with a prefixed range of carbon atoms means a straight-chain or branched hydrocarbon radical with a range corresponding to this range Carbon atom number, which contains at least one multiple bond, which can be located at any position of the unsaturated radical in question.
• (C 3 -C 10 ) alkenyl thus stands for example for the allyl, 2-methylpropenyl, 1- or
• (C 3 -C 10 ) alkynyl stands for example for the propargyl, 2-methylpropinyl, 2-butynyl,
• Pentynyl 2-methylpentynyl, hexynyl, heptynyl, octynyl, nonynyl or the decynyl group.
• (C 2 -C 10 ) alkynyl are the radicals mentioned above and the ethynyl
• (C 3 -C 10 ) cycloalkyl stands for monocyclic alkyl radicals, such as the cyclopropyl
• (C 4 -C 10 ) Cycloalkenyl stands for monocyclic cycloalkylene radicals, such as the
• Bicyclo [2.2.2] octenyl residue or for condensed systems such as the tetra, hexa- or octahydronaphthyl residue.
• Methylbutyryl, pivaloyl, octanoyl or decanoyl group Methylbutyryl, pivaloyl, octanoyl or decanoyl group.
• (C 3 -C ⁇ o) alkenoyl stands for example for the acrylic, methacrylic, crotonoyl, dimethylacryl or octenoyl group.
• (C 3 -C ⁇ o) alkynoyl stands for example for the propinoyl, butinoyl, hexinoyl or octinoyl
• (C 4 -C ⁇ o) cycloalkanoyl stands for. B. for cyclopropylcarbonyl, cyclobutylcarbonyl,
• Cycloalkenyloxy are ether groups whose hydrocarbon radicals have the terms" (C 3 -C 10 ) alkenyl ",” (C 3 -C 10 ) alkynyl ",” (C 3 -C 10 ) cycloalkyl "and" (C 4 -C 10 ) -
• Cycloalkenyl "have the meanings given.” (C 3 -C ⁇ o) -cycloalkyl- (C ⁇ -C) -alkoxy "stands for example for the cyclopropylmethoxy,
• (C 4 -C ⁇ o) cycloalkenyl (C 3 -C) alkenyloxy stands for. B. for the cyclobutenylallyloxy or the cyclopentenylallyloxy group.
• (-C-C 4 ) alkyl (C 3 -C -o) -cycloalkoxy stands for. B. for the methylcyclopentyloxy
• (C 2 -C 4 ) alkynyl (C 3 -C 10 ) cycloalkoxy represents e.g. B. for the ethynylcyclopentyloxy, propynylcyclopentyloxy, ethynylcyclohexyloxy or propynylcyclohexyloxy
• (CrC 4 ) alkoxy- (-C-C 4 ) alkoxy means an alkoxy as defined above
• Methoxyallyloxy group "Mono- or di- (-C-C ⁇ 0 ) alkylcarbamoyl, the latter radical optionally cyclically linked and optionally containing a heteroatom unit such as oxygen, sulfur, S (O) or S (O) 2 " means, for example, the methyl, ethyl -, Propyl, isopropyl, butyl or tert-butyl-carbamoyl group or the dimethyl, diethyl, methyl-ethyl or diisopropylcarbamoyl group, but also cyclic derivatives, such as the pyrrolidino, morpholino, thiomorpholino - or piperidino-carbamoyl group.
• (C 3 -C ⁇ o) cycloalkoxycarbonyl means, for. B. the cyclopropoxycarbonyl, cyclobutoxycarbonyl, cyclopentyloxycarbonyl or the cyclohexyloxycarbonyl group.
• (-C-C ⁇ o) alkanoyloxy means z.
• (C 4 -C ⁇ o) cycloalkanoyloxy means, for. B. the cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or the cyclohexylcarbonyloxy group.
• (C ⁇ -C ⁇ o) alkanoylamino means z.
• (C 3 -C ⁇ o) -alkenoylamino means z.
• (C 4 -C ⁇ o) cycloalkenyl (-C 4 ) alkylsulfinyl represents, for example
• (C 2 -C 4 ) alkenyl (C 3 -C ⁇ o) cycloaIkylamino stands for example for the vinylcyclopentylamino, allylcyclopentylamino, vinylcyclohexylamino or the allylcyclohexylamino group.
• (C 2 -C 4 ) Alkynyl (C 3 -C ⁇ o) -cycloaIkyIamino stands for example for the ethynylcyclopentylamino, propargylcyclopentylamino, ethynylcyclohexylamino or the propargylcyclohexylamino group.
• Aryl- (C 3 -C 4 ) alkenylthio stands for an aryl residue linked via a (C 3 -C 4 ) alkenylthio group, for example the 1-, 2- or 3-phenylallylthio residue.
• AryKC ⁇ C ⁇ alkylamino stands for an aryl radical linked via a (C ⁇ C ⁇ alkylamino group, for example the benzylamino, naphthylamino, the 1- or 2-phenylethylamino or the 3-phenylpropylamino radical.
• Haloalkylsulfinyl such as trifluoromethylsulfinyl
• Haloalkylsulfonyl such as trifluoromethylsulfonyl
• Halocyclopropyl such as 1, 1-difluorocyclopropyl
• Haloalkanoyl such as trifluoroacetyl
• Haloalkylamino such as 2,2,2-trifluoroethylamino.
• the compounds of the formula (I) have acidic or basic properties and can form salts. If the compounds of the formula (I) carry hydroxyl, carboxy or other groups which induce acidic properties, these compounds can be reacted with bases to form salts. Suitable bases are, for example, hydroxides, carbonates, hydrogen carbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines with (C 1 -C 4 ) -alkyl radicals and mono-, di- and trialkanolamines of (-C-C 4 ) alkanols. If the compounds of the formula (I) carry amino, alkylamino or other groups which induce basic properties, these can
• Suitable acids are, for example, mineral acids, such as hydrochloric, sulfuric and phosphoric acids, organic acids, such as acetic acid or oxalic acid, and acidic salts, such as NaHSO and KHSO 4 .
• the salts obtainable in this way also have insecticidal, acaricidal and miticidal properties.
• the preparation takes place under reaction conditions which are known and suitable for the reactions mentioned. Use can also be made of variants which are known per se and are not mentioned here in detail.
• the present invention also relates to processes for the preparation of compounds of the formula (I).
• a number of commercially available devices can be used for the parallel reaction and processing, for example from the companies Stern Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H + P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleissheim, Germany or the company Radleys, Shirehill, Saffron Waiden, Essex, England.
• Chromatography apparatuses are available, for example, from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA for the parallelized purification of compounds of the formula (I) or of intermediate products obtained in the preparation.
• Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus. , Eutetranychus spp ..
• Diplopoda e.g. Blaniulus guttulatus.
• Chilopoda e.g. Geophilus carpophagus, Scutigera spp ..
• Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
• Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
• Oestrus spp. Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
• Gastropoda e.g. Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp ..
• Gastropoda e.g. Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp ..
• Bivalva for example Dreissena spp.
• Protozoa such as Eimeria can also be controlled.
• the plant-parasitic nematodes that can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as those of the genera Meloidogyne (root-bile nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, Heterodera trifolii), such as Radisopolate, such as Radophenolholatus, such as Radophenolatheus, such as Radophenolus, such as Radophenolatheus, such as Radophenolatheus, such as Radophenolus, such as Radophenolus, such as Radophenolate, such as Radophenolate, such as Radophenolate, such as Radophenolate, such as Radophenolate, such as Radophenolate
• Tylenchulus such as Tylenchulus semipenetrans, Tylenchorhynchus such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus such as Rotylenchus robustus, Heliocotylenchus such as Haliocotylenchus multicinctus,
• the compounds of the invention can combat the nematode genera Ditylenchus (stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes such as Aphelenchoides ritzemabosi) and Anguina (flower nematodes such as Anguina tritici).
• Ditylenchus stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor
• Aphelenchoides leaf nematodes such as Aphelenchoides ritzemabosi
• Anguina flower nematodes such as Anguina tritici.
• the compounds according to the invention are preferably suitable for controlling sucking insects, such as aphids (for example Aphis fabae, Aphis pomi, Aphis spiraecola, Aphis gossypii, Aphis nasturtii, Dysaphis plantaginea, Eriosoma spp., Rhopalosiphum padi, Acyrthosiphon pisumursus, Pemus Myzus persicae, Myzus nicotianae, Myzus euphorbiae, Phylloxera spp., Toxoptera spp, Brevicoryne brassicae, Macrosiphum avenae, Macrosiphum euphorbiae, Nasonovia ribisnigri, Sitobion avenae, Brachycaudus helychrodisusiosis, cisodonosisosiodiscaisodiso
• the invention also relates to compositions, for example pesticides, preferably insecticides, acaricidal, ixodicidal, nematicidal, molluscicidal or fungicidal, particularly preferably insecticidal and acaricidal compositions which contain one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.
• pesticides preferably insecticides, acaricidal, ixodicidal, nematicidal, molluscicidal or fungicidal, particularly preferably insecticidal and acaricidal compositions which contain one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.
• the active ingredient and the other additives are combined and brought into a suitable form of use.
• the agents according to the invention generally contain the active ingredient (s) of the formula (I) in an amount of 1 to 95% by weight. They can be formulated in different ways, depending on how it is specified by the biological and / or chemical-physical parameters. Possible formulation options include:
• WP Wettable powder
• EC emulsifiable concentrates
• SL aqueous solutions
• SC oil or water-based dispersions
• SE suspoemulsions
• SE suspoemulsions
• DP dusts
• mordants granules in the form of , Spray, elevator and adsorption granules
• WG water-dispersible granules
• ULV formulations microcapsules, waxes or baits.
• auxiliaries ie carrier and / or surface-active substances, such as inert materials, surfactants, solvents and other additives, are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Garriers", 2nd Ed., Darland Books, Caldwell NJ; H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, NY; Marsden, Solvents Guide, 2nd Ed., Interscience, NY 1950; McCutcheon's, Detergents and Emulsifiers Annual, MC Publ.
• Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active ingredient, contain wetting agents, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium.
• wetting agents e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium.
• Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
• organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons.
• alkylarylsulfonic acid calcium salts such as cadodecylbenzene sulfonate
• nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, alkyl polyethers, sorbitan acid ester fatty acid sorbitol polyesters, fatty oxyorbitol fatty acid sorbitol or polyoxyethylene esters or polyoxyethylene esters or polyoxyethylene esters or polyoxyethylene esters
• Dusts are obtained by grinding the active ingredient with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite, pyrophillite or diatomaceous earth.
• Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates using adhesives, for example polyvinyl alcohol, polyacrylic acid sodium or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material.
• adhesives for example polyvinyl alcohol, polyacrylic acid sodium or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material.
• Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
• the active ingredient concentration in wettable powders is usually about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation components. In the case of emulsifiable concentrates, the active substance concentration is approximately 5 to 80% by weight. Dust-like formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 2 to 20 wt .-%. In the case of granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulation aids, fillers, etc. are used.
• the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
• the concentrates which are available in the commercially available form, are optionally diluted in the customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and sometimes also for microgranules using water. Dust-like and granulated preparations as well as sprayable solutions are usually no longer diluted with other inert substances before use.
• the application rate required varies with the external conditions such as temperature, humidity and others. It can vary within wide limits, for example between 0.0005 and 10.0 kg / ha or more of active substance, but is preferably between 0.001 and 5 kg / ha of active substance.
• the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
• the pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds and substances produced by microorganisms.
• Preferred mix partners are:
• Prothiofos Pyraclofos, Pyridapenthion, Quinalphos, Sulprofos, Temephos, Terbufos, Tebupirimfos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorphon, Vamidothion;
• Tebufenozide Tebufenpyrad
• Teflubenzuron Tefluthrin
• Tetradifon Tetrasul
• Thiacloprid Thiametoxam, Thiocyclam
• Tolfenpyrad Triazamate
• Triflumuron Verbutin
• Vertalec Mycotal
• the active substance content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight.
• the application takes place in a customary manner adapted to the application forms.
• the invention therefore relates to the use of compounds of the formula (I) and their salts for controlling animal pests, preferably harmful arthropods, such as insects and arachnids, helminths and / or nematodes.
• animal pests preferably harmful arthropods, such as insects and arachnids, helminths and / or nematodes.
• the invention furthermore relates to a process for controlling harmful insects, arachnids and / or helminths, an effective amount of a compound of the formula (I) or its salts being applied to the pests or to the location of the desired action.
• the compounds of the formula (I) can accordingly also be used advantageously in livestock farming (for example cattle, sheep, pigs and poultry such as chickens, geese, etc.).
• livestock farming for example cattle, sheep, pigs and poultry such as chickens, geese, etc.
• the compounds if appropriate in suitable formulations and if appropriate with the drinking water or feed, are administered to the animals orally.
• There one Excretion in the feces is effective, it is very easy to prevent the development of insects in the feces of the animals.
• the appropriate dosages and formulations depend in particular on the type and stage of development of the farm animals and also on the infestation pressure and can be easily determined and determined using the customary methods.
• the compounds can be used in cattle, for example, in doses of 0.01 to 1 mg / kg of body weight.
• the active compounds according to the invention can be used in a special way for the treatment of vegetative and generative propagation material, such as e.g. of seeds of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamental plants, of onions, cuttings and tubers of other vegetatively propagated crops and ornamental plants.
• vegetative and generative propagation material such as e.g. of seeds of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamental plants, of onions, cuttings and tubers of other vegetatively propagated crops and ornamental plants.
• the treatment for this can take place before the sowing or planting process (e.g. using special techniques of seed coating, by dressing in liquid or solid form or seed box treatment), during the sowing process or planting or after the sowing or planting process by special application techniques (eg seed row treatment).
• the amount of active ingredient used can vary over a wide range depending on the application. In general, the application rates are between 1 g and 10 kg of active ingredient per
• the compounds of the formula (I) or their salts are also notable for a pronounced repellent effect.
• Repellent in the sense of the description is a substance or mixture of substances that has a protective or expelling effect on other living beings, in particular pests and nuisances.
• the term also includes effects such as the antifeeding effect, in which food intake is disturbed or prevented (antagonistic effect), suppression of egg laying or influencing population development.
• N- (4-trifluoromethyl-nicotinoyl) -3-aminopropionsulfonic acid piperidide 5.32 g (15 mmol) (4-trifluoromethyl-nicotinic acid) -3- (benzylthio) propylamide (Example G) was in a mixture of 3.5 ml Water and 25 ml of glacial acetic acid are introduced and chlorine gas is introduced while cooling with ice. The reaction was complete after 20 minutes. The mixture was diluted with water, extracted several times with dichloromethane, the combined organic phases were stirred twice with aqueous bicarbonate solution, dried and concentrated. The crude acid chloride was purified by chromatography on silica gel (ethyl acetate).
• N-(4-trifluoromethylnicotinoyl) -3-aminopropionaldehyde diethylacetal was first prepared from 1-aminopropionaldehyde diethylacetal and 4-trifluoromethyl-nicotinoyl chloride in the presence of triethylamine (colorless solid, mp 59-60 ° C., yield 91. 8% of theory).
• the acetal was saponified by stirring with formic acid, to which a little water was added (1 hour, 30-40 ° C.). For working up, the formic acid was stripped off, the residue was taken up in dichloromethane / sodium bicarbonate solution and the organic phase was dried and concentrated. You got that Product as a colorless oil (73.1% of theory), which was reacted further without further purification.
• a dusting agent is obtained by mixing 10 parts by weight of active ingredient and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
• a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active ingredient, 65 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as the and dispersant mixes and grinds in a pin mill.
• a dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a Sulfosuccinic acid half ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water are mixed and ground in a attritor to a fineness of less than 5 microns.
• An emulsifiable concentrate can be prepared from 15 parts by weight of active ingredient, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.
• Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert granule carrier material such as attapulgite, pumice granules and / or
• Silica sand A suspension of the wettable powder from example b) with a solids content of 30% is expediently used and sprayed onto the surface of an attapulgite granulate, dried and mixed intimately.
• the proportion by weight of the wettable powder is approximately 5% and that of the inert carrier material approximately 95% of the finished granulate.
• Germinated field bean seeds (Vicia faba) with germ roots were transferred to amber glass bottles filled with tap water.
• Four milliliters of an aqueous solution of the compound to be tested and formulated were pipetted into the amber glass bottle.
• the broad bean was heavily coated with about 100 black bean aphids (Aphis fabae).
• the plant and aphids were then stored in a climatic chamber (16 hours light / day, 25 ° C., 40-60% RH). After 3 and 6 days of storage, the root systemic effect of the compound on the aphids was determined.
• the compounds according to Example Nos At a concentration of 300 ppm (based on the active ingredient content), the compounds according to Example Nos.
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
• Chinese cabbage leaf slices (Brassica pekinensis), which were affected by all stages of the green peach aphid (Myzus persicae), were sprayed with an active compound preparation of the desired concentration. After the desired time, the effect was determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

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• 2003
  • 2003-02-25 DE DE10307845A patent/DE10307845A1/de not_active Withdrawn
• 2004
  • 2004-02-19 JP JP2006501884A patent/JP2006518721A/ja active Pending
  • 2004-02-19 MX MXPA05008999A patent/MXPA05008999A/es unknown
  • 2004-02-19 EP EP04712514A patent/EP1601654A1/de not_active Withdrawn
  • 2004-02-19 US US10/547,004 patent/US20060173022A1/en not_active Abandoned
  • 2004-02-19 KR KR1020057015640A patent/KR20050102139A/ko not_active Application Discontinuation
  • 2004-02-19 BR BRPI0407842-0A patent/BRPI0407842A/pt not_active Application Discontinuation
  • 2004-02-19 WO PCT/EP2004/001577 patent/WO2004076421A1/de not_active Application Discontinuation
  • 2004-02-25 TW TW093104799A patent/TW200510318A/zh unknown
• 2005
  • 2005-08-02 ZA ZA200506154A patent/ZA200506154B/en unknown

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