DK2686303T3 - N-(3-carbamoylphenyl)-1h-pyrazol-5-carboxamid-derivativer og deres anvendelse til bekæmpelse af skadedyr - Google Patents

N-(3-carbamoylphenyl)-1h-pyrazol-5-carboxamid-derivativer og deres anvendelse til bekæmpelse af skadedyr Download PDF

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DK2686303T3
DK2686303T3 DK12707819.4T DK12707819T DK2686303T3 DK 2686303 T3 DK2686303 T3 DK 2686303T3 DK 12707819 T DK12707819 T DK 12707819T DK 2686303 T3 DK2686303 T3 DK 2686303T3
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methyl
butyl
compounds
plants
ethyl
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Isabelle Adelt
Markus Heil
Peter Jeschke
Olga Malsam
Peter Lösel
Arnd Voerste
Ulrich Görgens
Michael Maue
Tobias Kapferer
Friedrich August Mühlthau
Alexander Sudau
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Bayer Ip Gmbh
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/18—One oxygen or sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/38—Nitrogen atoms
    • C07D231/40—Acylated on said nitrogen atom
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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  • Organic Chemistry (AREA)
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Claims (11)

1. Forbindelser med den almene formel (I),
hvor R1 betegner hydrogen, eventuelt substitueret Ci-C6-alkyl, C2-C6~ alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, Ci-Ce-alkylcarbonyl, Ci-C6-alkoxycarbonyl, cyan-Ci-C2-alkyl, aryl-(C1-C3)-alkyl, heteroaryl- (C1-C3) -alkyl, den kemiske gruppe Ai betegner CR2 eller nitrogen, A2 betegner CR3 eller nitrogen, A3 betegner CR4 eller nitrogen og A4 betegner CR5 eller nitrogen, men hvor der ikke mere end tre af kemiske grupper Ai til A4 samtidigt repræsentere nitrogen; R2, R3, R4 og R5 uafhængigt af hinanden betegner hydrogen, halogen, CN, N02/ eventuelt substitueret Ci-C6-alkyl, C4-C6-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C4-C6- alkoxy, Ci-C6-halogenalkoxy, Ci-C6_alkylthio, Ci-C6- halogenalkylthio, Ci-C6-alkylsulfinyl, C1-C6- halogenalkylsulphinyl, Ci-C6_alkylsulfonyl, C1-C6- halogenalkylsulf onyl, Ci-C 6-al kyl amino, N, N-di -C1-C6- al kyl amino, N-Ci-C6-al kyl amino carbonyl, N-C3-C6-cycloalkylaminocarbonyl eller (C4-C3-alkoxy)carbonyl; hvis ingen af grupperne A2 og A3 betegner nitrogen, kan R3 og R4 sammen med det carbonatom, hvortil de er bundet, danne en 5-eller 6-leddet ring, som indeholder 0, 1 eller 2 nitrogenatomer og/eller 0 eller 1 oxygenatom og/eller 0 eller 1 svovlatom, eller hvis ingen af grupperne A4 og A2 betegner nitrogen, kan R2 og R3 sammen med det carbonatom, hvortil de er bundet, danne en 6- leddet ring, som indeholder 0, 1 eller 2 nitrogenatomer; W betegner oxygen eller svovl; R6 betegner hydrogen, eventuelt substitueret Ci-C6-alkyl, aryl-(Ci-C3) -alkyl, heteroaryl- (C1-C3) -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, (Ci-C3-alkyl) -C3-C6-cycloalkyl og (C3-C6_cycloalkyl)-Ci-C3-alkyl, Ci-C6-alkylcarbonyl, C1-C6- alkoxycarbonyl; Q betegner
E betegner en binding, -CH2-, S, SO, S02, -S-CH2 -, -SO-CH2-, -S02-CH2-, -CH2-S-CH2-, -CH2-SO-CH2 -, -CH2-S02-CH2-, -S-CH2-CH2-, -SO-CH2-CH2-, -SO2-CH2-CH2-, -nr6-ch2-, -ch2-nr6-ch2-; R7 betegner cyano eller C (= S)NH2; Z1 betegner eventuelt substitueret Ci-C6-halogenalkyl eller C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, og Z2 betegner halogen, cyan, nitro eller eventuelt substitueret Ci~C6-halogenalkyl, Ci-C6_alkylthio, Ci-C6-halogenalkylthio, Ci-C6~alkylsulfinyl, Ci-C6-halogenalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6_halogenalkylsulfonyl, og Z3 betegner hydrogen eller eventuelt substitueret Ci-C6-alkyl, Ci-C4-alkenyl, Ci-C4~alkynyl, Ci-C6_halogenalkyl.
2. Forbindelser med den almene formel (I) ifølge krav 1, hvor R1 betegner hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl, t- butoxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl, 2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl, pyrid-3-yl-methyl, pyrid-4-yl-methyl, 4-chlor-pyrid-3-yl-methyl; den kemiske gruppe Ai betegner CR2 eller nitrogen, A2 betegner CR3 eller nitrogen, A3 betegner CR4 eller nitrogen og A4 betegner CR5 eller nitrogen, men hvor ikke mere end tre af de kemiske grupper Ai til A4 samtidigt betegner nitrogen; R2 og R5 uafhængigt af hinanden betegner hydrogen, methyl, fluor eller chlor og R3 og R4 uafhængigt af hinanden betegner hydrogen, fluor, chlor, brom, CN, N02, methyl, ethyl, fluormethyl, difluormethyl, trifluormethyl, 2,2,2-trifluorethyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluormethoxy, difluormethoxy, chlordifluormethoxy, dichlorfluormethoxy, trifluormethoxy, 2,2,2-trifluorethoxy, 2-chlor-2,2- difluorethoxy, pentafluorethoxy, methylsulfonyl, methylsulfinyl, trifluormethylsulfony1, trifluoromethylsulphinyl; hvor W betegner oxygen, R6 betegner hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl, t- butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl, t- butoxycarbonyl, cyanomethyl, 2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl, pyrid-3-ylmethyl, pyrid-4-yl-methyl, 4-chlorpyrid-3-ylmethyl; Q betegner
E betegner en binding eller -CH2-; R7 betegner cyano eller C(=S)NH2; Z1 betegner difluormethyl, trichlormethyl, chlordifluormethyl, dichlorfluormethyl, trifluormethyl, bromdichlormethyl, chlormethyl, brommethyl, 1-fluorethyl, 1-fluor-l-methylethyl, 2-fluorethyl, 2,2-difluorethyl, 2,2,2-trifluorethyl, 1,2,2,2- tetrafluorethyl, 1-chlor-l,2,2,2-tetrafluorethyl, 2,2,2- trichlorethyl, 2-chlor-2,2-difluorethyl, 1,1-difluorethyl, pentafluorethyl, pentafluor-t-butyl, heptafluor-n-propyl, heptafluorisopropyl, nonafluor-n-butyl, cyclopropyl, 1-chlorcyclopropyl, 1-fluorcyclopropyl, 1-bromcyclopropyl, 1- cyancyclopropyl, 1-trifluormethylcyclopropyl, cyclobutyl eller 2.2- difluor-l-methylcyclopropyl, og Z2 betegner halogen, cyan, nitro, difluormethyl, trichlormethyl, chlordifluormethyl, dichlorfluormethyl, trifluormethyl, bromodichloromethyl, chlormethyl, brommethyl, 1-fluorethyl, 1-fluor-l-methylethyl, 2-fluorethyl, 2,2- difluorethyl, 2,2,2-trifluorethyl, 1,2,2,2-tetrafluorethyl, 1- chlor-1,2,2,2-tetrafluorethyl, 2,2,2-trichlorethyl, 2-chlor- 2.2- difluorethyl, 1,1-difluoroethyl, pentafluorethyl, pentafluor-t-butyl, heptafluor-n-propyl, heptafluorisopropyl, nonafluoro-n-butyl, methylthio, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethylsulfonyl, trifluormethylthio, trifluoromethylsulphinyl, trifluormethylsulfonyl, og Z3 betegner hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, ethenyl, 1-propenyl, 2-propenyl, ethynyl, 1-propynyl, 1-butynyl, difluormethyl, trichlormethyl, chlordifluormethyl, dichlorfluormethyl, trifluormethyl, chlormethyl, brommethyl, 1-fluorethyl, 1- fluor-l-methylethyl, 2-fluorethyl, 2,2-difluorethyl, 2,2,2- trifluorethyl.
3. Forbindelser med den almene formel (I) ifølge krav 1 eller 2, hvor Z1 betegner trifluormethyl, 1-chlorcyclopropyl, 1-fluorcyclopropyl eller pentafluorethyl, Z2 betegner trifluormethyl, nitro, methylthio, methylsulfinyl, methylsulfonyl, fluor, chlor, brom eller iod, Z3 betegner methyl, ethyl, n-propyl eller hydrogen, R1 betegner hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl, t- butoxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl, 2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-yl-methyl, pyrid-3-yl-methyl, pyrid-4-yl-methyl, 4-chlor-pyrid-3-yl-methyl, A1, A2 og A4 betegner CH, A3 betegner CR4 og R4 betegner fluor, chlor, brom eller iod, R6 betegner hydrogen, methyl, ethyl, n-propyl, isopropyl, n-methyl, isobutyl, s-butyl, t-butyl, W betegner oxygen, og Q betegner 1-cyancyclopropyl.
4. Forbindelser med den almene formel (I) ifølge ethvert af kravene 1 til 3, hvor Z1 betegner trifluormethyl, 1-chlor-cyclopropyl, 1-fluor cyclopropyl eller pentafluorethyl, Z2 betegner trifluormethyl, chlor eller, Z3 betegner methyl, R1 betegner hydrogen, methyl, ethyl, A1, A2 og A4 betegner CH, A3 betegner CR4 og R4 betegner chlor, R6 betegner hydrogen, methyl, ethyl, W betegner oxygen, og Q betegner 1-cyancyclopropyl.
5. Anvendelse af forbindelser med den almene formel (I) ifølge ethvert af kravene 1 til 4 til bekæmpelse af insekter, spindlere og nematoder for at beskytte planter.
6. Farmaceutiske sammensætninger omfattende mindst en forbindelse ifølge et af kravene 1 til 4.
7. Forbindelser ifølge ethvert af kravene 1 til 4 til anvendelse som medikamenter.
8. Fremgangsmåde til fremstilling af plantebeskyttelsesmidler omfattende forbindelser med den almene formel (I) ifølge et vilkårligt af kravene 1 til 4 og sædvanlige strækkemidler og/eller overfladeaktive stoffer.
9. Fremgangsmåde til bekæmpelse af skadedyr på planter eller frø, kendetegnet ved, at en forbindelse med den almene formel (I) ifølge et af kravene 1 til 4 tillades at virke på skadedyrene og/eller deres levested.
10. Anvendelse af forbindelser med den almene formel (I) ifølge ethvert af kravene 1 til 4 til beskyttelse af formeringsmateriale af planter, især frø.
11. Forbindelser med de almene formler (IVa) og (IVb),
hvor R2, R3, R4 og R5 uafhængigt af hinanden betegner hydrogen, halogen, cyan, nitro, eventuelt substitueret Ci-C6_alkyl, Ci-C6~ halogenalkyl, C3-C6-cycloalkyl, C3-C6_halogencycloalkyl, Ci-C6~ alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6- halogenalkylthio, Ci-C6~alkylsulfinyl, Ci-Cg-haloalkylsulphinyl, Ci-C6-alkylsulfonyl, Ci-C6-halogenalkylsulfonyl, Ci-C6- alkylamino, N, N-di-Ci-C6_alkylamino, N-Ci-C6-alkylaminocarbonyl, N-C3-C6-cycloalkylaminocarbonyl eller (Ci-C3-alkoxy)carbonyl.
DK12707819.4T 2011-03-18 2012-03-12 N-(3-carbamoylphenyl)-1h-pyrazol-5-carboxamid-derivativer og deres anvendelse til bekæmpelse af skadedyr DK2686303T3 (da)

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US201161454134P 2011-03-18 2011-03-18
EP11158838 2011-03-18
EP11190693 2011-11-25
PCT/EP2012/054299 WO2012126766A1 (de) 2011-03-18 2012-03-12 N- (3 -carbamoylphenyl) - 1h - pyrazol - 5 - carboxamid - derivate und ihre verwendung zur bekämpfung von tierischen schädlingen

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KR (1) KR101834362B1 (da)
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RU (1) RU2600739C2 (da)
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