TW318829B - - Google Patents

Download PDF

Info

Publication number
TW318829B
TW318829B TW084102527A TW84102527A TW318829B TW 318829 B TW318829 B TW 318829B TW 084102527 A TW084102527 A TW 084102527A TW 84102527 A TW84102527 A TW 84102527A TW 318829 B TW318829 B TW 318829B
Authority
TW
Taiwan
Prior art keywords
group
coome
pyridyl
alkyl
meo
Prior art date
Application number
TW084102527A
Other languages
English (en)
Original Assignee
Agrevo Uk Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Agrevo Uk Ltd filed Critical Agrevo Uk Ltd
Application granted granted Critical
Publication of TW318829B publication Critical patent/TW318829B/zh

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81Amides; Imides
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, 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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/501,3-Diazoles; Hydrogenated 1,3-diazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/501,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/521,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/601,4-Diazines; Hydrogenated 1,4-diazines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713Biocides, 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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, 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
    • A01N43/82Biocides, 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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, 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
    • A01N43/84Biocides, 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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12Carbamic 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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20N-Aryl derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N59/00Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16Heavy metals; Compounds thereof
    • A01N59/20Copper
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10Antimycotics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81Amides; Imides
    • C07D213/82Amides; Imides in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic 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
    • C07D231/12Heterocyclic 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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/30Halogen atoms or nitro radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/34One oxygen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/38One sulfur atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/42One nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52Two oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56One oxygen atom and one sulfur atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
    • C07D241/24Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/12Heterocyclic 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 chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/12Heterocyclic 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

318829 Α7 Β7 i、發明説明( 本發明闞於用作殺真菌劑的新穎鄰胺基苯甲酸衍生物。 前吐坊越 GB 1,563,664及日本公告(Japanese Kokai&gt; —53130655 號掲示鄰胺基苯甲酸酯的殺真菌劑。發明人發現特定的新 穎鄰胺基笨甲酸衍生物也具有價值的殺真菌活性’且其優 點勝於此等公告所揭示的化合物。 太發明根示 根據本發明,提供一種式I化合物
(I) (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局負工消費合作社印製 其中 X是 A是 R1是 0或S ; 含至少一個氮原子的6員的雜芳基,視需要可被一 或多個R 2基圑取代; 烷基,環烷基,環烯基,烯基*炔基或胺基’(每 一此等基圑可視需要經取代)、η ,鹵素’氰 基,硝基,醯基,醯氧基,視需要經取代的苯基; 或二個相鄱基圑與其相聯的碳原子共同形成苯并環 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(2 ) 9 R2之 意義與R1同,或二僩相鄰的與其相脚的碳原子共同 形成視需要取代的雜環; Y是 烷基•環烷基,環烯基,烯基或炔基,每一此等基 團可視需要經取代,氫或醢基; Y1之 意義與Y同*或是視需要經取代的苯基或是視需要 取代的雜瑁; Z是 CkXM-X^-R3,氰基,硝基,胺基•醣基•視需要 取代的雜環,-(:(1?6)=1^-01^或-(:(1^&gt;=»1-«1^117; R3是 烷基,環烷基,環烯基&gt; 烯基》炔基》苯基或雜環 •每一此等基團可視需要經取代,氫或無機或有機 陽離子基團; X1及 X2,可相同或相異•是0或S; R6, Re&amp;R7,可相同或相異,是烷基,環烷基,瑁烯基 ,烯基,炔基,笨基或雜瓖,每一此等基圈可視需 要經取代·或氫或Re&amp;R7與其相聯的碳原子共同形 成一環; η是 0至4 ; 及與金鼸鼸形成的錯合物,Μ及與_所成的《(當化合物 為酸)及與酸所成的篇(當化合物為,前題是在Υ為 氫且 i ) ζ為羧基,甲氧羰基或乙氧羰基時,環Α不是未經取 代的吡啶基或吡畊基;而 ϋ &gt;在ζ為羧基且1»是0時,A不是2-氣-4-吡啶基· &amp;-( 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) I-----:--------iT (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印裝 A7 B7 五、發明説明(5 ) 2-二乙胺乙氧基)-3-吡啶基或2-吡啶基。 烷基較佳是1至20個•例如1至6個•破原子的。烯基及 炔基一般是3至6個碳原子。環烷基或環烯基較佳是3至6個 碳原子。 取代基,在見於烷基、環烷基、環烯基、烯基或炔基上 時,包括鹵素,叠篦基,氰基,視需要取代的烷氧基,視 需要取代的烷硫基,羥基,硝基,視需要取代的胺基*醣 基,醣氧基*視裔要取代的苯基,視需要取代的雜環,視 需要取代的苯氧基及視需要取代的_環氧基。 瑁烷基及環烯基也可K烷基取代。 見於任何苯基上的取代基一般是一或多僩如R1所界定的 基團。 雑環一詞包括芳香族及非芳香族雑瓖基團。雜環基團一 般是5,6或7員的環,含達4個選自氮,氧,及硫的雜原 子。雜瑁基圈的例是呋喃基,噻盼基*吡咯基•吡咯啉基 ,吡咯啶基,眯唑基*二氧戊瓌基·噚唑基*噻唑基,眯 唑基,咪唑啉基,咪唑啶基,吡唑基,吡唑啉基,吡唑啶 基,異嗶唑基,異噻唑基,嗶二唑基•***基,_二唑基 *吡喃基•吡啶基,六氫吡啶基•二嗶烷基,嗎福啉基· 吡畊基,六氫吡畊基,三畊基*噻唑啉基》苯并眯唑基, 四唑基,苯并噚唑基*眯唑吡啶基,1,3-笨并噚畊基· 1,3-苯并噻畊基,嗶唑吡啶基,笨并呋哺基,《明:基•枝 唑啉基,晻喔唞基,環丁礪基•二簋_唑啉基,苯并_唑 基,酞皤亞胺基•苯并呋喃基•吖庚因基及苯并二13 丫庚因 -6 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210 X 297公嫠) -------:—:士衣— (請先閲讀背面之注意事項再填寫本頁) 訂 318629 at Β7 i、發明説明(4 ) 基° 雜瑁基團本身也可是取代的,如取代的苯基。 胺基可由,例如•一或二個視霈要取代的烷基或醢基所 取代,或二個取代基形成一環,較佳是5 -至7 -員的環,而 此等環也可是取代的,並含其他雜原子,例如嗎福啉*硫 代嗎福啉或六氫吡啶。 醮基一詞包括硫及含磷的酸或羧酸的殘基。釀基的例是 -CORB · -COOR8 · -CXHRBRe · -CON (RB)ORe · -C00NRBRe ,-COH (RB)HReR7 ,-COSR6,-CSSRB ♦ -S (0)PRB · -S(0)z0R5 » -S(0)pNRBRe » -P ( =X) (0RB) (0Re) · -C0-C00Re ,其中RB· ReRR7之定義如前述*或1^及1{7與 其相聪的原子共同形成一環,P是1或2,而X是OSS。 A —般較佳是吡啶(尤其是3-吡啶基&gt;·嘧啶(尤其是 5-嘧啶基),或吡畊環。A也可是,例如四畊*吡畊或三 畊環。 R2較佳是選自鹵素,尤其是氟,或烷基,尤其是甲基。 f較佳是(ΜζΧΜ-Χ2-!?3,X1及X2較佳都是0,R—般是烷基 ,烯基或炔基•每一此等基團是視需要取代的•特別是甲 基。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) Υ較佳是氫•烷基,尤其是甲基或醮基*尤其是烷醣基 或烷氧醣基。 X較佳是0 。 η較佳是0 。 本發明的此等化合物一般是由式Han 2的Μ形成*其中Μ 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X297公釐) 經濟部中央橾準局員工消貧合作社印製 A7 B7 五、發明説明(5 ) 為二價金靨陽離子,例如網錳、鈷,鏵、嫌或鋅,而An為 陰雄子,例如氯化合物,硝酸嬲或碕酸鹽。 本發明化合物對多種原自半知菌類、子囊菌類、藻狀菌 類、及擔子菌類的病原菌都有抗菌活性•特別是對植物的 真菌疾病*如霉病*特別是大麥白粉病(Erysiphe graeinia) * 黃瓜白粉病(Erysiphe cichoracaeruB) 及葡 萄箱霉病 (Plasaopara viticola及 Uncinula necator) · 稻瘟病(Pyricularia oryzae),毅 BBSS (P s e u d o c e r c o s p o r e 1 1 a h e r* p o t r i c h i d o s ),稻鞴疫病 (Pellicularia sasakii),灰霉病(Botrytis cinerea), 小麥棟銹病(Pucinia recondita) *晩期蕃S3或馬铃薯疫 病(P h y t o p h t h o r a i n f e s t a n s ) * 蘋果瘡痂病(V e n t u r* i a inaequalis)及穎斑病(Leptosphaeria nodorum)。可能 有些化合物只對幾種病原菌有效,其他的有廣效活性· 有些式I化合物具有弱殺蟲活性·但仍可用作中間»· 而此類化合物也是本發明的一方面。 本發明化合物一般調配成殺真菌的傅統姐合物。此等姐 合物可含一種或多種農藥,例如具餘草性質的、殺真菌性 質的、殺昆盡性質的、殺滿性霣的或殺線蟲性質的化合物 Ο 本發明姐合物中的稀釋劑或載劑可以是固體或液體,視 需要加有界面活性劑,例如分散劑•乳化劑或增湄劑。合 適的界面活性劑包括陰離子化合物*例如羧酸化合物•長 - 8 - 本紙張尺度適用中國國家梯準(CNS &gt; A4規格(210X297公釐) -------:---A------1T (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(6 ) 鏈腊肪酸的羧酸金靨;釀基肌胺酸鹽,帶有脂肪酵乙氧 基化合物的單一或二一磷酸酯或此等酯的鼸;硫酸麵腊肪 酵,如十二烷基疏酸納•十八烷基硫酸納或十六烷基硫酸 納;乙氣化腊肪酵疏酸獼•,乙氧化烷酚基醃酸釀;磺酸木 素;磺酸石油;磺酸烷基芳基酯如烷基笨磺酸酯或低烷基 奈磺酸酯,例如丁基奈磺酸酯;磺酸奈一甲醛箱合物;磺 酸化酚一甲醛縮合物的鹽;或更複嫌的磺酸酿如纗胺磺酸 _,例如油酸及H -甲基牛磺酸磺酸化縮合物或二烷基磺基 丁二酸_,例如二辛基丁二酸磺酸納。非鐮子劑包括脂肪 酸酯、脂肪醇、脂肪酸醯胺或脂肪烷基或烯基取代的酚與 環氧乙烷的縮合產物*多羥基酵酯的脂肪《,例如山梨糖 酵脂肪酸酯*此等酯與環氧乙烷的縮合物*例如聚環氧乙 烷山梨糖醇脂肪酸酯•環氧乙烷輿氧化丙烯的嵌共聚物, 炔靨二酵如2,4,7,9-四甲基-5-癸炔-4,7-二酵,或乙氧 化炔二酵。陽離子界面活性麵的例包括•例如,胞肪族單 一、二一或多胺醋酸酷•環烷酸酯、或油酸醮;含氧的胺 如氧化胺或聚氧乙烯烷基胺;由羧酸輿二-或多胺縮合製 成的聯结釀胺的胺;或四级銨鼸。 本發明姐合物可Μ此技藉所已知的任何雇蕖爾形*如溶 液·分散液•水性乳液,撒粉,種子包衣(seed dressing),滅蒸劑》煙霧劑(3«1〇156),可分散的粉,可 乳化的湄縮物*或頼粒。此外,也可Μ是通於直接使用的 形式,或者是澹縮物或初鈒姐合物,在使用前遴量的水或 其他稀釋劑稀釋。 -9 - 本紙張尺度適用中國國家橾準(CNS ) Α4規格(210X297公嫠) -------:---*衣------、訂 (請先閲讀背面之注意事項再填寫本頁) 318829 A7 _B7_ 五、發明説明(7 ) 作為分散液時,此類姐合物係由本發明化合物分散於液 體介質(較佳是水)内構成。供應使用者時較佳是初鈒姐 合物*此姐合物可用水稀釋成所需溻度的分散液。初級姐 合物可以下述任何形式供應。可Μ是含有溶於可與水混溶 的溶劑内的本發明化合物,並加有分散爾。另一種是含有 磨成细粉的本發明化合物及分散劑•與水均勻混合物成期 或霜*必要時可加於水包油的乳液中,形成水性油乳液内 有有效成分的分散液。 可乳化的濃縮物含有不與水混溶的溶麵内的本發明化合 物及乳化劑•與水混合物時形成乳液。 撒粉含有本發明化合物及與其均勻混合的粉末稀釋_ * 例如高領土。 顆粒固體含有本發明化合物及類似用於擔粉的稀釋劑· 但此混合物係用已知方法製成頼粒。或者是將有效成分吸 附於預先製成的顆粒稀釋劑上*例如吸附於傅勒式土 (Ful. ler’s earth&gt;±,美 _活性白土(attagulgite)上或 石灰石沙上。 可濕的粉一般含有效成分、合缠的界面活性劑及惰性粉 稀釋劑(如瓷土)。 經濟部中央橾準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 另一合4的濃縮物*特別是在產物為固體時*是可流動 的懸浮液濃縮物,此係由磨碎此化合物、水、增濕爾及懸 浮劑製成。 本發明組合物中有效成分的濃度較佳是在1至30重量百 分比範圔内,尤佳是在5至30重量百分比範画内。初級姐 -10 - 本紙張尺度適用中國國家梂準(CNS ) A4规格(210Χ:297公釐)
A7 B7 五、發明説明(8 ) 合物中有效成分的量的變化範圍很大,例如,可佔姐合物 重量的百分之5至95。 本發明化合物可用已知方式製備,例如,用式II化合物 (II) 與式111化合物反應 0
II (III) ---.I^-- (請先閱讀背面之注意事項再填寫本頁) 訂 其中Q是離去基,較佳是鹵素,尤其是氯*產生式I化合 物,其中X是0,Y是氫,如有必要將此化合物用已知方法 修改,生成另一化合物,其中X及 /或γ有另外所需的值, 如有必要再將式I化合物用已知方法改成另一化合物,其 中R1,R2及Z有其他值。 化合物II及III之間的反應一般是在有鹼(例如有機三 级胺〉之存在下在溶劑(如醚)内進行。 化合物II及III是已知的或可用已知方法製備的。 所得式I化合物可用已知方式修改成另一式1化合物, 即是將基團之一修改成另一所需基團° 例如,可用已知方法將醋轉化成自由態的酸或鹽。 11 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) -良· 經濟部中央標準局負工消費合作社印装 Α7 Β7 五、發明説明(9 ) 疏代基圄可用氧化劑•如-氯過苯甲酸,氧化成亞磺釀 基或磺醯基。 炭基可藉已知方法*例如用勞孫式(Lawesson)試劑或五 碲化磷,硫化成硫代炭基。 以合缠的羥基或氫碕基化合物反應,A環上的烷磺醢基 可由合遘的親核基(如芳氧基或芳确基 &gt; 代替。 本發明Μ下述實例說明。分雕出的新穎化合物構造係用 元素及/或其他合遘的分析箱實。溫度Kt:表示。 ------------ 装-- (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 將三乙基胺(28.4克)加於6-氯菸_酸(40克&gt; 於無水 二氣甲烷( 900毫升)内之溶液中。此混合物於冰浴内冷 卻,滴加氛甲酸甲_( 26.8克)。此混合物於室通播拌過 夜*輪流用水、碳酸氫納水溶液及鹽水洗。有機相於碲酸 鎂上乾嫌,遇濾•蒸發,得6-菸_酸甲_。 將10克此產物加於甲酵納(由1.61克納及100毫升甲酵 製得)中。此混合物於回流下加熱3小時·於室溫靜置過 夜。加氫氧化鉀水溶液(10克氫氧化鉀於30奄升水内&gt; * 再將此混合物於回流加熱8小時。再於室溫靜置過夜,蒸 發*將殘餘物加於水(120毫升)内。用鹽酸將混合物酸 化至出3。遇濾沉澱物,乾煉,得6-甲氧基菸_酸*熔點 175 — 177 υ 〇 將此酸(6克)與超董之亞硫醢氣於回流加熱2小時。 將混合物冷卻,蒸發•將殘餘物(含粗製6-甲氧基菸鐮醣 -12 - 本紙張尺度適用中國國家標準(CNS ) Α4规格(210X297公釐&gt; 、?τ 經濟部中央揉準局員工消費合作社印製 A 7 B7 五、發明説明(10 ) 氛)溶於無水四氫呋喃(10奄升)内。將此溶液滴加於鄰 胺基笨甲酸甲酯(6.22克)及三乙基胺(7.92克)於四氫 呋喃( 200毫升)内之溶液中。此混合物於室通攪半《夜 ,蒸發* 酸乙_萃取。萃取物用水洗*乾嫌並蒸發, 殘餘物於二氧化矽膠柱上作色層分析純化*製得(6 -甲 氧基菸《8(醣基 &gt; 鄰胺基笨甲酸甲醮•熔黏121-3。(化合物 1) ° Μ類似方式製得Η- (2-甲磙基-5-唯啶羰基)鄹胺基苯 甲酸甲«,熔點166-8。(化合物la&gt; 。 奮例___2. 將氫化納(0.15克*60X的於油内之溶液)加於由實例 1所得化合物(1克)於無水四氫呋喃(25毫升)内之已 於冰浴上冷卻之溶液中。將此混合物攪拌2 0分鐘·然後加 甲基碘(0.44毫升 &gt; 。此混合物於室溫播拌48小時*蒸發 •用_酸乙酷萃取。萃取物輪流用水及鹽水洗,於确酸鎂 上乾嫌,蒸發。殘餘物於二氧化矽膠柱上作色層分析純化 ,製得N- ( 6-甲氧菸鐮醣基&gt; 甲基邮胺基苯甲酸甲酯 ,熔黏68-70。。(化合物2) 於由實例2所製化合物2 (0.6克)於乙酵(20毫升) 内之溶液中加氯化鋦(11)(0.134克 &gt; 。將混合物靜置過 夜,蒸發,殘餘物用酷酸乙醏研磨,製得贰一〔甲基N-( -13 - 本紙張尺度適用中國國家橾準(CNS ) Α4規格(210X297公釐) --------I Λ-- (請先閲讀背面之注意事項再填寫本頁) 訂 良. 318829 at Β7 五、發明説明(11) 6 -甲氧基菸鹺醐基&gt; -N-甲基郾胺基笨甲酸_〕氛化鋦 (II)錯合物*熔點196-8β。(化合物3&gt; 例-^ 將B-氯遇苯甲酸(13.7克)在播拌下加於化合物la(6 克)於二氛甲烷内之溶液中。此混合物於室溫攪拌過夜· 加硫酸納,用二氮甲烷萃取。萃取物經處理後得N- (2 -甲 磺醣基-5-嘧啶羰基)鄰胺基笨甲_甲_ *熔點187-9°。 (化合物4) 將氫化納(0.24克*60X内的於油内之溶液)加於2-駑 硫基吡啶(0.33克)於無水二甲基甲釀胺(20亳升)内之 溶液中。此混合物於室溫攪拌半小時。在攫拌下滴加化合 物4 (1克)於無水二甲基甲醣胺(20毫升)内之溶液。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 此混合物於室溫攪拌遇夜。冷卻,用甲酵使停止反應。將 混合物倒入水内,用稀鹽酸使成酸性。收取沉澱物,溶於 二氯甲烷内,此溶液用蘧水洗,蒸發,得H-〔2- (2-吡啶 碕基)-5-嘧啶羰基〕一鄰胺基笨甲_甲_,熔點145-147° (化合物 5) 以類似方式,使用碳酸鉀代替氫化納作_,製得N-〔 2- (4-甲氧苯氧基&gt; -5-嘧啶羰基)一鄰胺基苯甲酸甲酯 *為油體(化合物5a)。 一 14 - 本紙張尺度適用中國國家揉準(CNS ) Α4規格(210X297公釐) Α7 Β7 五、發明説明(彳2 ) 啻俐 fi 將化合物1輿等莫耳量的氫氧化納加热•製得N- (6-甲 氧菸鐮醢基)一鄰胺基苯甲酸•熔點224-3。(化合物6) 再將此化合物用氫氧化納處理*製得製得N- (6-甲氧转 齙醣基 鄰胺基笨甲酸納,熔點&gt;250。(化合物6a&gt; 奮俐 7 將勞孫氏試_ (2,4-贰(4-甲氧苯基&gt; -1,3-二_ -2.4-二鼷2.4-二碴化物;5.09克)加於化合物1 (3克 &gt;於四氬呋_ (100毫升)内之溶液中。此混合物於氮氣 下搢拌20小時。再加勞孫氏轼瘌(2.6克)*此混合物於 回流加熱13小時*蒸發,殘餘物於二氧化矽腰柱上作色臛 分析鈍化,製得N- (6 -甲氧基-3-吡啶磓羰基)鄹胺基苯 甲酸甲酯*熔點133-4°。(化合物7&gt; 。 Μ類似前面揭示的實例之一之製法,製得下列式I化合 物0 ----------------、訂------^ (請先閲讀背面之注意事項再填寫本頁) 經濟部中央榡準局*:工消費合作社印製 5 ix 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公嫠) 318829 A7 B7 五、發明説明(15 Y Ο Ν—-G—ί (I) 經濟部中央標準局員工消費合作社印製 化合物 Z Y A 熔點Ο S CCOMe H 5-£^〇-3-啦咱基 150-2 9 — COOEt H 6-Meow 喷基 129-30 10 - coost Me 6 -MeO - 3 -% 喷基 31-2 11 - COOne -CH2CN 6-14£:〇-3_耻0^ 基 oil 12 - COOMe -COOMe 6-MeC-3-吡啶基 gum 13 3-Me cooMe n 6-MeO-3.-B比啶基 111-2 14 5-C1 COOMe K 63 —啦症基 172-3 15 4,5-(MeO)2 COOMe H 6-MeO* 3-¾¾¾ 173-5 16 一 coo苄基 Me 6-Me。-3-¾ 口定基 110-3 17 5-Cl COOMe Me 6-MeO-3-吡啶基 89-91 IS 4 r5-(MeO)2 COOMe Me 6-MeO-3-吡啶基 147-50 19 5-Mes cooMe H 6-MeO-3 胃Pit 喷基 135-7 20 5-MeS COOMe Me 6-1^0-3-¾0¾ 基 78-SO 2_ι CN 6-MeO-3-tft 啶基 163 — δ 22 — CN Me 6-MeO - 3 -啦症基 90,5-3 23 - COMe ΣΙ 6-MSO-3-:吡啶基 131-5-4 24 — N〇2 H 6-MeCX -:¾ 陡基 125-7 25 — COOMe K 5-MeO-2-吡哄基 169-70 26 6-Me c〇〇Me H 6 —ΪΊ©0—3 — 1¾ 1¾ ^ 102.5-5 27 - CCOHe Ή 5-Cl-6-MeO- 165-6 3-吡啶基 16 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X297公釐) I--------:——士衣------ir------&amp;K. (請先閲讀背面之注意事項再填寫本頁) 318829 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明(U ) ib合物 (-)η η Y A 熔點(°) 2δ - CCOMe Me 5-C1-6-Me〇— 3-¾:喷基 110-2 29 6-Me COOMe Me 6 —MeO — 3 — 0¾ B定基 1;Ι7·5_3·5 30 一 COOPrj K 6-HeO-3-吡啶基 :107-9 31 場 COOMe H 6-MeS - 3、0¾ 喃基 102.5-5 32 擊 COOMe Me S-StO-3-耻啶基 oil 33 » CCCMe H 4,6-(MeO)2-5-嘧啶基 125-7 34 - COOMe H 5^6—(M^O)2&quot; 2-吡阱基 156-9 35 Μ COCMe He 3-吡啶基 36-S 36 一 SO-Me II 6-MeO-3-吡啶基 143 * 5-50.5 37 SOMe H 6-Me〇-3-吡啶基 111-3 38 4-NCH COOMe Me 6 —- 3 —耻陡基 110-2 39 - COOH 2-F-苄基 6-Me〇-3-啦喷基 195-7 40 4-MeOCO COCMe Me 6-MeO-2,(ft 啶基 109-12 41 CONH-OMe H 6 —MeO * 3 —眼艇基 152-3 42 - COOMe H 5-(3-唪吩基 )_ 3-吡啶基 149-50 43 一 COOMe Me 6-*NH〇*~3-耻®基 119-22 44 COOMe H S_pr!Ci-3-社啶基 15-7 45 - 四唑. 5_基 -Me 6-MeO-3-败陡基 19S-200 45 — SO^Me He e-MeO-3-Dtti^g 100-2 47 COOMe H S-MeCOO-3“吡啶基 109-12 43 3-C1 COOMe H 6-MeO-3-lft 唯基 106-10 49 COOMe H 4-C1-2-吡啶基 15S-οϋ 50 COOPr H 6_舶〇-3』比咱基: 107-9 51 _ COOBu H 6-贴〇-3-口比唯基 57-60 S2 COOPr Me 6-MeO-3-ft 暗基 81.5-4 53 _ COOBu Me 6-MeO-3-吡啶基 72-6 54 3-C1 COOMe Me 6-MeO-3-吡啶基 S4-7 (請先閱讀背面之注意事項再填寫本頁) -17 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210X2.97公釐) 經濟部中央標準局員工消費合作社印製 A7 _____B7 五、發明説明(15 ) 化合物 z Y Λ 瑢點. 55 mm CON-OMe ί Me 6-HeO - 3-口比0^基 147^50 l Mo 56 — CKC H 6-^0-3-¾¾¾ 117-20 57 ·*· COO-allyl u 6 -Μ©0 - 3 - p比陡基 93-5.5 53 4-C1 COOMe 陡基 98-100 59 - COOMe -CK2C=CH 6-MeO-3-耻症基 84*5-87 60 •Η C=N-NHMe I H 6-MeO-3-p^ 喷基 124-34 1 Me 61 C=N-〇Me 1 H 6-Me〇-3-卩比嗤基 115-6 Me 62 4-F COOMe H 6-MeO-3-% 啶基 125-6 63 _ coonh4 H 6-1^^0-3-¾1¾¾ 250-2 64 5,6—本并 COOMe H δ, 157-61 65 4-CF- COOMe H 6-MeO-3-%^S 139-42 66 » COOMe 4_CF3_苄基 6 -MeC- 3 -;Plt ^ ® 111-3 67 — CON-OMe [ K 6-MeO-3-吡啶基 102-4 Me 68 COOMe H 6-MeNH-3-吡啶基 I87-S9 69 - COOMe 2 - Me-苄基 6_贴0-3場?吡啶基 112-4 70 - COOMe 4™MeO一 节基 6-MeO-3 一 基 115-21 71 CONK K 6 -MeO-3 w 1¾ 植基 165-7 CH-7Ph 72 一 COOMe Me 2-吡啶基 3〇-a 73 _ COOMe Η 2-MeO-4-姬旋基. 132-5 74 邏 COOMe Η 5,6-012-3-¾ 陡基 161-2 75 — COO- N 十 Bu4 H 6-MeO-3-吡啶基 250-2 76 . · COOMe Η 2-C1-3- ’耻陡基 120-1 77 COOMe Η 2 -MeO- 3 —阳:陡基 7S-S1 -18 - (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家檬準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明(16) 化合物⑺Μη 2 經濟部中央標準局屬工消費合作社印製 78 - CKO Me 6-Meo-3 - 0比陡基: 83-4 79 - CH=N-〇H h 咱基 145-6 80 - I * H 6_5^0_3_啦啶基— 87-9 1 Me 81 - I H 嗤基. 140-2 82 - COOMe H 2-MCS-3-吡啶基. 117-9 83 - COOMe 5-Br-6-MeO~ 164-3 3-吡啶基, 34 - COCNe Me 5—Br-^ —MeO ^ 112-4 3-毗啶基 3 5 — COGMc H 5-ΜθΟ-2 基 141-3 36 - COO^ie H 6*-Μθ-3 -基 125-6 37 5-Me COOMe H 2-MeO-3-吡啶基 13S-40 33 - COOCjH^ K 6-MeO-3-¾¾ 基 4S-52 S3 — CC〇Cr〇- H 6-MeO-3_.吡啶基 125-7 COOMe 90 ~ COOCK-j- H 6-MeO«3-〇lt〇£S 129-32 91 — COOBu1 H 6 -MeCW 3 - % 哺基. S1-3 32 _ COOHe H 5-Ph-6-Mc〇- 159-61 3 -啦腔基、 93 - COOKe -CII: ?C〇OHe 6-MeO-3-基 oil 94 * cootoenzyl .H 2-MeO-3—% 症基 79-30 95 ~ CONKHe H 6 - - Oft 陡基, 162-4 96 - C—N-OMe 1 MO 6-MGO-3-吡啶基: oil 1 Me 97 - Ph H 6-^6〇-3-:0比°^基: 107-9 - 5-(4-Cl- H 6 -MeG - 3 &quot;眼喷基 193-7 Ph)-i,3,4- 二啤-2-基 (請先閱讀背面之注意事項再填寫本頁) -19 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明(17)
化合物(RA)n Z 99 - 100 4-F^S-Me 101 -102 - 103 ^
104 5-F 105 - 10 6 -107 -* 102 - 109 一 110 - 111 -112 - 113 - 114 - 115 — llo 4-He 117 一 IIS - 119 5-Me 120 -121 G-Cl
A 經濟部中央標準局員工消費合作社印装 環己基 COO· Ν + Η] H S-MeO-O-吡啶基.. 203-5 環己基. COOMe Η 2-MeO—3 —阳;0¾ 基. glass 2-furyl H 6-MeO-3-吡啶基. 112-7 cooch2- K 6-MeO-3-吡啶基 155-δ CK-,G1 cookie Me ,2—MeO-3-耻喷基 oil COCHe H 6-MeO-3·% 晚基 125-6 COOMe 稀丙基 oil COOMe 乙醯基 色 3 -1¾唯基 oil COOMe 苯甲醯基 6-14^0-3-¾¾¾ 117-S COOMe 3,4~Ήβ〇2&quot; 6-MeO-3·吡啶基‘ 116-8 COOMe ph.—CH-sCH.^ -Η 5 eO— 3 _ (¾ D定基 117-9 COOMe -CH2Ph S-Cl-6—Me〇- 126-8 COOMe Me 3-吡啶基‘ 5,S-Cl2-3-吡啶基.. 103-4 COOMe II 5—C1 — 6 —M©S — 167-9 COOMe K 3-吡啶基 比啼基 122-3 5-(4-CI- Me 6-MeO-3 - Pfci:喷基 13S-91 Ph)-1,2,4-晖二唑-2-基 COCM^ Μβ 4,6-(ΜβΟ)2&quot; 111-3 COOMe H 2-嘧啶基. 6-MeO-3-'卩比η定基 116-9 COOMe Me 5_MeO—2 — 基 ^ 82*4 SO^NHMe u 6-MeO-3-®:喃基 sclid COOMe H 6_Me〇-3 -ift嗤基 丄 5G-2 COOM^ Mg 5—Me〇一 3 一 Ptti® 基 ¢0-2 COOMe K 6-Me〇-3-吡啶基 160-2 -------Γ--------ίτ------良 (請先閲讀背面之注意事項再填寫本頁) 20 本紙張尺度適用中國國家標準 (CNS ) A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 __B7 五、發明説明(18 ) 化合物 (Rl)n Z V A 熔點.(3) 122 cc〇Me H 5,6_(MeO)2_ 3-吡啶基 155-7 123 一 5-(4-01-PhJ-1,3,4-_二唑-2-基 H 6-ile〇-3-吡啶基 215-7 124 - C0NH COOMe H 6-MeO-3-1¾ 嗤基 140-2 125 4-C1 COOMe H 2-(MeS〇2)&quot; 啶基 183-5 126 5-NO, •COOMe K 6-ΜβΟ-3 -啦唯基 197-9 127 3,5-Me? C00MC H 咱基: 131-3 123 - COOMe SO舞 6-Μθ:0·3 -啦陡基 125-8 129 - COOHe II 4 —Hg〇&quot;~2 — MsSO·^ w 5-啼陡基 lS7_9〇 130 i·吡咯基 H 5-Me〇-3-Dtt 唯基 113-6 131 4—Cl COOMe H 剛定基 175-7 132 cooMe H S-Me〇-3-吡啶基 177-9 133 4-MeO COOMe H 6-Mg〇-3 -啦嗦基 164-5 134 — COOMC -CH(M$)Ph 6 '&quot;MoO- 3 _ 〇H: 1¾ 基 132-3 135 - COOMe Me 5/6-(ΜβΟ)2&quot; 3-吡啶基. 110-2 136 一 C〇CH?0Me H 6-MeO-3-吡啶基: 110-2 137 - CONH, H 6-MeO-姬陡基&lt; 224-S 138 一 COOMe H 4· wCl-6 —〔N_ (2—MeOCO— Ph)HHCO]-2* 吡啶基. 210-2 139 CCOMe H 4—McO—β— [ N— (2 -M.eO— CO-Pii)NHCO]-2-吡啶基 195-9 140 - COOMe H 6-[N-(2-Me〇CO-Ph)-NFCO] -3*·阳:唯基 198-200 141 一 COOMe H 6-CF3CH2〇-3-吡啶基. 173-4 (請先閱讀背面之注意事項再填寫本頁) -21 - 本紙張尺度適用中國國家標準(CNS ) A4規格(2IOX297公釐) A7 經濟部中央標準局員工消費合作社印製 318829 B7 五、發明説明(19 ) 化合物(ν)η 2 Y A 诏點.(。 142 替 co〇Me H 2,5-(MeO)2_6-[N— (2 -MeOCD-Ptl) NHCO ] ^ 3-%¾基 195-9 143 麵 COOHe 4,6-(EtO)2-2-吡啶基 115-6 144 - C〇NEt2 H 6-Me〇-3-吡啶基 oil 145 conhnh2 K 6-Me〇-3-吡啶基 183-9 145 - CONH- N=CMe2 H 6-Me〇-3-吡啶基 174-7 147 - COOM 白 2-Me-苄基 2-MeO-3-吡啶基.. 101-3 14S ?-νη2 COOMe H 6-MeO-3-吡啶基 171-3 149 - COOMe H 6-(2,3, pyrrol.yl〉*-3-吼喃基 1S3 150 — SCH〇CH?CN !l 0 l·: S-MeO-3-吡啶基 113-5 151 2-benz— R imidasolyl o 6 —M eQ—3 - 1】比P定基 272—5 152 - li SCH^CH-^CN il 0 H 6-MeO-3-吡啶基. I41-3 153 COMHNH- COMe H 6 一 Me〇一 3 參 1¾ 0¾ 基 193-7 154 一 C〇〇-ally丄 H 5-Cl-6-MeO-3-吡啶基 113-5 155 — COOCHo- C^CH H 5-Cl-6-MeO- 3-吡啶基. 10 3 — 5 156 3-F CCOMe u 6 -MeO — 3 _口比 基 107-9 157 5-ΟΗ co〇Me H 6-MeO-3-吡啶基 203-5 15S 5-1 CCOMe H (3-Me〇-3-吡啶基 154—0 159 5-Me〇C〇 COOMe H 6-MeO-3-pttng 基 155—β (請先閲讀背面之注意事項再填寫本頁) -22 -本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A 7 __B7 五、發明説明(20 ) 化合物(R1)^ Z Y 熔點(3) 160 5-MeCONH COOMe H 2S2-6 161 - GOOMe -CH(Me)-COCHe 6-MeO-3-吡啶基· 134-5 152 - COCMc 节基 5-Cl-6-MeO-3-吡啶基. oil 163 — COOEt H 5-Cl-6-MeO-3-吡啶基. 136-3 164 - COOH H 5-Cl-6-Me0-3'- Ptt 喃基_ 247-50 165 5-MSSO-7NH .COOMe H 6〜ΜβΟ-3-败症基 184-5 1S6 C00M° H 5-氣基:-3-¾咱基_ ISC*2 167 COOiMe H 卜甲酿基-3-¾啼基 153-7 16S CONH- (4-Cl»Ph) H 6-HeO-3-D(£D$g ias-90 159 - COOMe K 5-3r-2-Me〇-3-吡啶基 180-2 17C 4-Cl cooKe Me 2-MeO-5-暗症基 S 6 —δ 171 COOMe H 2-01-4-¾ 暗基 10S-1C 172 一 COOMe H 2- G1-6-MOO- 3- 吡啶基 144-5 173 - COOHe H 6-(2r3f4,5-Cl4-1-¾略基-)-3-吼陡基 2S9 174 _ COONa H 6-C1-3-PH:咱基. 300 175 一 COOMe H 6-MeOCH,-3-% 啶基 117-8 176 - COOMe H 5-氮基 3-吡啶基 247-50 177 - 5-Me-1,3,4-噻二唑-2-基 H β—M©〇—3 — 〇比唯基 143-5 173 - COOM^ H 3-吡啶基. iy〇-2 179 — COOMe H 5—MeSO,〇—3 _眼旋基. 149-51 (請先閲讀背面之注意事項再填寫本頁) -23 麵 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 318329 Α7 Β7 五、發明説明(21 ) 化台物 熔點(°)
130 - COOMe H 181 - COGMe H 132 - COOHe H 133 - COOKe H 184 - COOHe II 185 - COOHe H 18 6 - CCOHe H 1S7 - cocHe H 183 * COOMe Me 1S9 - COOMe H 19 0 · CCCMe Me 191 - COOMe H 192 一 C00H ti 193 - COOMe Π 194 - COOHe H 19 5 - COOHe H 196 - COOMe H 197 - cooHe H 19S - COOMe H 199 - -CO-COOMe II 200 - COCMe He 201 - C〇〇Me Me 202 _ CCOMe He 203 - COOH H 6-(2,3,5-CI3- 134-5 卜吡咯基 )-3-吡啶基 6-MeOCO_3_ 耻1® 基 141 5-P定基. 123-31 5 —He £—3 — ft 0¾ S. 122-3 5-MeOCO-2-吡啶基. 1S7_S 2 f 6- (MeO) 2** 141-3 3-吡啶基 5--社啼基_ 155-70 5-MeS〇-3 -ρ%1® S' 120-2 基 oil (N^C—CH-^O)— so?Lid 3-吡啶基 5—HcSO〇&quot;3 —社啼基 109-11 5-C lCIi2S - 3 -毗啶基· 6-C1-3- Ptt1® ®, 240 5-&gt;MeOCO-3 -附‘啶基 14 7-3 6-[N-(2-HeOCO-Ph)- 195-9 KHCO 陡基 5 - Me-3 -pi% 唯基 116-7 NO7— 15 0—1 3-吡啶基, 6-Ph〇-3- 'ftBiS, 97-s 5 f (MeS) 2* 157—8 3—吡啶基 6-KeO“3-耻症基 13 3-6 2 f 6- (HeO&gt;2^ 103-5 3-吡啶基. Pth^E® oil 5-Me-3-吡啶基. 114-5 5 -aoco- 3 啶基 275 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印策 _ 24 — 本紙張尺度適用中國國家標準(CNS ) Α4規格(210Χ297公釐) 五、發明説明(22 ) A7 B7 經濟部中央標準局員工消費合作社印製 化合物(R1、 z Y A 熔點(°) 204 - COOMe H S-乙醯基-S-Me- 3-吡啶基 144-5 205 - COOMG H 5-Ph-3- 〇tt 唯基: 12A-5 206 - COOMe Me 6-PhO-3-吡啶基i 114-5 207 - COOMe H 5**[N-(2-Me0C0-Ph)-NHC0 ;] - 3 -耻 _ 硫基 180-2 202 - cooMe H S-phCH^jS-S-吡啶基 104-6 209 - cooMe Me 5 - MeO-2-W:畊基 81-3 210 4-? COOHe Me 6 - % 症基 102-4 211 - COOMfit Et 6-Me〇-3-Pft 啶基. 53-5 212 - COOMe H 2-Me〇-5-喷症基 164-S 213 - COOMe Me 2-Me〇-5&quot;嘧B定基. 125-30 214 - COOMe H 4, 6-(MeO)2_2-PhCH2〇- 5-嘧啶基 127-$ 215 - cooMe H 2-C1-4C?:'-5-嘧啶基 139-40 2 IS - COOMe H 2-Me-;N-4CF3-5-嘧啶基 133-6 217 - COOMe H 2-MeO-4CF3™ 5-嘧啶基: 13940 21S · COOMe H 6-Cl-5-MeO-2-〇ttn井基 163-71 219 - COCMe H 5-Br-2-Me- 4-嘧啶基 165-6 220 - COOMe H 2,4,6-(MeO)3-5-嘧啶基 153-5 221 » COOMe He 6β1-3-吡啶基. 8 4 — 6 222 - COOMe H 2-C1-4-嘧啶基 159-61 223 - COOTie 5-Me-2-吡畊基 224 一 c〇GMe H 2-MeO-4 -喃唯基 135-6 225 - co〇Pr H 2 -HeSO-7— 5-嗯喃基 — 129-31 —25 — 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X 297公漦) -----------i衣-- (請先閱讀背面之注意事項再填寫本頁) ,ιτ 經濟部中央標準局員工消費合作社印製 318829 A7 B7 五、發明説明(25 ) 226 - COOPr H 2-MeSO- 5-嘧啶基 116-3 227 - COOPr H 2-Me〇-5-嘧啶基,. 1U4-5 228 - COOEt H 2WtO-5-啼陡基. 134-5 229 - COOH H 2-Et〇-5-嘧啶基 150*62 230 - COOMe H 2-Me-5-p:啼唯基 141 — 3 231 - coOMe H 5-嘧啶基 15S-61 232 · co〇Me Me 2-Me-5-嘧啶基. 83-90 233 - COOMe U 2-C1-5—嘧啶基 _ 159-61 234 - COOHe H 2-Br-5-嘧啶基 177—3 2 J 5 - 'COOMe H 2-PhCH2NH-5-嘧啶基 192-4 236 一 COOMe H 2-嗎福啉基 5-〇g症基 222-3 237 - COOMe K 5-Br-2-MeS- 嘧啶基 192-4 23S - cooMe H 4-嘧啶基 178-30 239 - COOMft H 2-MeCC〇CH2NH-5-嘧啶基 194-7 240 - cooMe H 2 , δ-ΟΙο&quot;* 4-嘧啶基 170-5 241 - C00MO H 2-CF3**5-暗啶基. 143-5 242 - COOMg H 2-Ph*5-赠啼基, .151-5 243 - COOMq H 2,6-(MeO)2&quot; 4-嘧啶基 167—9 244 - COOMe Me 2-Ph-5-嘧啶基 gura 245 - COOMe H 2; 6-Cl2~ 5-嘧啶基 135-7 246 - COOMe H 2-NC-5-嘧啶基 136-3 247 - COCMc H 4,5- (MeO) 2&quot; 2-嘧啶基 1S2-3 (請先閱讀背面之注意事項再填寫本頁) * 26 -本紙張尺度適用中國國家梂準(CNS ) A4规格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A7 __B7 五、發明説明(24 ) 化合物(w)n 2 V A ‘熔點(。) 243 - COOMe H 4/6-(MeO)2-2-嘧啶基 163 — 4 249 - CCOMe H 2-MeONK-5-嘧啶基 19 4 — β 250 - COOMe H 5-嘧啶基 230-1 251 - COOMe H 2-CI-4-(2-MeOCO-PMH) - 5-嘧啶基 190-2 252 - COOMe 5-Ci-6wMe-2-吡畊基 136-41 2B3 - 'COOMe K 5-HeO-5-Me_ 2-吡畊基 16 6 — 9 254 — COOMe u 2-(N-甲氧基 一 N#甲氧猿基 _ 胺基 )-5-嘧啶基 151-2 255 COOlie K 2-環丙基 S--嘧啶基. 112-^ 256 3-MeOCO COOMe u 6 _MeO - 3 — 口比喷基 111-4 257 COOMe H 2-MeS-5-嘧啶基 160-2 25S 一 COOMe H 5,2-阳:哄基 143-S 259 - COOMe H 5-(2-_噻吩基)-3-吡啶基_ 143-9 260 - COOMe H 5-(i-CF3-Ph)-3-吡啶基: 155-6 261 — COOMe H 5-(ClS〇2)-3-吡啶基. 144-3 252 - COOMe H 5-(CL2CHS)» 3-吡啶基 120-2 263 COOMe H 5-(NH2S〇2) -3-吡啶基. 135-7 264 COOMe H 5-Br-6-Cl~3- 157-9 265 - COOMe He 5 - NO。一 6—MeO-3-吡啶基 9S-100 I----------1¾衣------?τ------ (請先閲讀背面之注意事項再填寫本頁) -27 - 本紙張尺度適用中國國家標準(CNS ) A4規格(2IOX297公釐) 318S29 A7 B7 五、發明説明(25 經濟部中央標準局員工消費合作社印製 化合物(y)n 2 V A 熔點(5) 256 辦 COCHe K 2-(l-眯唑基 Ιό-嘧啶基 193-5 267 _ COOMe H 4 ♦HeO-2—MeS·&quot;-5-喑啶基 140-2 258 — COOMe Me 2 f 6- (Me〇) 啤婉基 101-3 269 情 COOH 3, r 4-(HeO)2&quot; 苄基 社啼基 123-4 . 270 — COOMe H 5-(Me?NS〇2 卜 3 - 旋基 169—70_ 271 — COOMe H 5-Br—S^MeO— 3-基. 169-70 272 一 COOMG H 5—6—MgS〇7_ 3-吡啶基 223-5 273 - COOMe H 5—Sr—6.SC— 3-吡啶基. 160-2 274 — cooc5hu H 2-MeO-3-吡歧基 47-3 275 — COO-ally1 H 2-ΜβΟ-3-ϋίΡ定基. 80-1 276 - COOMe 2-Me-苄基 6-(2-Me-节基.)- 3-吡啶基 oil 277 一 COOMo H 2-C1-4-B奎睹咐基 163^4 27S 一 COOMe -CH2Ph 6-MeO-3-吡啶基 101-2 279 4,5-Me〇2 COOMe H 2-MeO~3-tft啶基: 152-4 2S0 COOMe n 5 —WH^ ^ 6 -Μβ〇·* 3-吡啶基. 202-3 231 — COOHe He 2,4- (MeO) 2&quot; 5-嘧啶基 7S-S1 282 - COOMe 2-MeO-苄基喃症基 gum 233 COCMc 4-Me-2-MeS-' 78-Sl 5-嘧啶基 28 良紙張尺度適用中國國家橾準(CNS ) A4規格(210X297公釐) (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 318329 A7 A7 B7 五、發明説明(26 ) 化合物(R1):! S Y A 熔點(°) 234 - COOMe H 2-(3-:¾咱氧基 )- l2d~6 5-嘧啶基. 2S5 * COOMe H 2-F-3-吡啶基 130-1 236 - COCMe 2 — S,6-(MeO)2- oil benzyl 3-吡啶基 2S7 - COCKe H 5 , S-伸甲基二氧基 w 168—79 3-吡啶基 233 _ COOMe H 5 -1 - 6 -MeO-卩比症基 173-5 289 3,4-Me2 COOM0 H 2 -MeO - 3 -卩tfc卩定基. 126-7 290 4-C1 COOMe H 2-MeO-3-吡陡基 128-30 -------:--------.訂------2 I (請先閲讀背面之注意事項再頊寫本頁) -29 - 本紙張尺度適用中國國家揉準(CNS ) A4^格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A7 _____B7 五、發明説明(2?) 也製備了下述化合物: a&gt;H- (6 -甲氧基-3-吡啶硪代炭基)鄰胺基苯甲酸乙_ * 為油體,(化合物291 ) b&gt;N- (5,6-二甲氧基-3-吡啶碕代炭基)鄰胺基苯甲酸甲 酯,熔點154-5。,(化合物292 ) c&gt;H- &lt;2-甲氧基-5-嘧啶硫代炭基 &gt; 鄰胺基笨甲酸甲酿, 熔點135-7。,&lt;化合物293 &gt;,及 d)N- &lt;6-甲氧基-3-吡啶硫代炭基)鄰胺基苯甲酸異丁 _ ,為油體·(化合物294 &gt;。 試驗奮例 評估各化合物對下列一或多種疾病之活性: P h y t 〇 p h t h o r a i n f e s t a n s :晩期蕃 S5 疫病 Plasaiopara viticola:葡萄霜霉病 Erysiphe graminis··大麥白粉病 Pyr丨cular丨a oryzae:招瘟病 Pellicularia sasakii:稻销疫病 B o t r y t i s c i n e r e a :灰霉病 V e n t u r i a ί n a e q u a 1 i s :顔果瘡痛病 Leptosphaeria nodorua:類斑病 M此等化合物所懦湄度的水溶液或分散液•包括增獮薄 *噴或浸於試驗植物的莖下部。然後將植物或植物的一部 分以合逋的試驗病原菌培養•使植物在受控制的條件下生 -30 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) I I I I— fA (請先閣讀背面之注意事項再填寫本頁)
第84102Γ)27號專利申請案 中文說明書修正頁(86年1月 五、發明説明( ----------裝—I----訂 (請先閱讀背面之注意事項再填寫本頁) 長,Μ便植物及病原菌都能發育。過一段合適的時間後* 肉眼估許植物感染部位的程度。評估真菌病害之控制程度 W分數0-4表示,其中各代表之意義如下: 〇= 0-24% 控制 1 = 25-49¾ 控制 2 = 50-74% 控制 3 = 75-98¾ 控制 4= 99-1003;控制 在化合物濃度為500 ppm (重量/容積)或更少時如分數 為2或2M上,即認為化合物對該疾病有活性。 於濃度500 ppm或更少: 化合物 30, 36, 43, 47, 58, 112, 115, 180, 242,及 289 之分數為 2或 2M 上 Μ 抗 Phytophthora infestans; 化合物 9, 30, 36, 40, 42, 57, 58, 59, 62, 63, 67-70. 76, 77, 82, 83, 96, 112, 115, 127, 129, 130, 132, 138, 139, 161, 163, 166, 181, 186, 200-204, 210, 213, 234, 248, 249, 261, 267, 268, 經濟部中央標準局員工消費合作社印製 271,及 2*77 之分數為 2 或 2M 上 Μ抗 Plasmopara viticola • 化合物 1-3,9-12,20, 23,25, 27-29,32, 33,34, 38, 39, 41, 46, 50, 52, 62, 66, 70, 73, 83, 84, 90, 91, 104-104, 110, 113, 115, 121-123, 132, 135, 145, 154, 155, 163, 176, 177, 196, 200, 208, -31 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐)
81妁 中文說明書修正頁(86年1月)T 02527號專利申謫案 A7 子月 3
Wi-i補充j 五、發明説明(Y) 209, 210-2, 213, 218, 228, 239, 243, 249, 150, 252-4, 258, 265, 268, 271-3, 275, 276, 278,及 286 之分數為2或2M上K抗Erysiphe graminis ; 化合物 1, la, 2, 6a, 48, 29, 54-56, 65,68, 72. 74, 75, 126, 129, 145, 146, 169, 171, 197, 230, 23 2,249,及 277 之分數為 2或 2K 上 Μ抗 Pyricularia 〇 r y z a e ; 化合物 14, 44, 49, 62, 1 14, 1 15 , 152, 21 1, 215, 216,及278之分數為2或2K上K抗Pellicularia sasaki i ; 化合物 48, 51, 52, 53, 61, 63, 1 21,129,195, 228 及 251 之分數為 2或 2M 上 Μ 抗 Botrytis cinerea; 化合物 1, 8, 12, 17, 45, 63, 86, 104, 112, 119, 146, 149, 150, 151, 187, 204, 211, 219, 224, 239, 244,245, 248,及250之分數為2或2M上以抗Venturia i n a e q u a 1 is ; 化合物 24, 35, 60, 61, 71, 204, 216, 220,及 249 之 分數為 2或 2M 上 M 抗 Leptosphaeria nodorum 。 ^^1-^^^1 m nn m m· m * 1^^1- 1^1^9J (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標隼局員工消費合作社印製 32 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐)

Claims (1)

  1. 第84102527號專利申請案 丨專利範圍條正太(86年1月) A8 . B8 ' 六、申請專利範圍 .一種式I之化合物 (R1) X
    N—C—A. (I) 其中 X是 A是 R1是 R2是 經濟部中央標準局員工消費合作社印製 0或S ; 吡啶基,吡阱基或嘧啶基,視需要可被一或多個 1?2基團取代; Cl-4综基,Cl-4齒fes基* Cl-Λ综氧基* Cl-4·院硫 基,咹基,酵烷基,(:烷磺醯胺基,鹵素 ,羥基,硝基,烷氧羥基,或二個相鄰的基 團與其相聯的碳原子共同形成茏并環; Cx-4烷氧基* Ck烷基,C!—鹵烷基,Ci-4烷氧 _Cl-4综基&gt; Cl-4®烧氧基,Cl-a综硫基,Cl-4 鹵烷碲基,吡啶硫基,吡啶氧基,鹵吡咯基, (Ca-4烷氧羰茏基)胺羰基,Cx-4烷氧羰基, 烷氧羰-Ct-a烷胺基*苄氧基,嗎福啉基, 氟基,烷氧基•胺基,Ci-4烷胺基,C:L-4烷 氢睽基,N - C i - &lt;1烷氧-N - C 1 - 4烷羰胺基,C i - 4醇 基,氧基,Ci-4烷碣臨·氧基,Ct-4烷磺醯 基’ Cl - 4综亞碌藤基,商素,哮吩基,硝基,梭 * /碏醻胺撐,N.N-Ci-A二烷磺藤胺撐,眯唑基 n^n ^1^11 HH «^—^1 n* fti^i— nil— ^mfl 1J 、va (請先閏讀背面之注意事-^再填寫本頁) 本纸張尺度速用中國國家標準(CNS ) A4洗格(210X297公釐) 31S829 公告‘本 A8ΰά -DS、 經濟部中央標準局員工消費合作社印製 申請專利範圍 ,或二個相鄰的基團與其相聯的碳原子共同形成 茏并或亞甲基二氧基; Y是 氫,C Λ - Λ烷基(:視需要羥氰基取代1,C t - 4烷氧羰 基,C2-4炔基,苄基(視裔要羥鹵素或Cl-4烷基 ,鹵-CP4烷基或烷氧基取代),醇基, 笮氧基*笼乙基,Ca-4 -烷磺醯基或α-甲基苄基 » Ζ是 氟基,硝基,Ci-4醇基(視需要經烷氧基取代), C 1 - a -烷磺酵基(視需要經氰基取代),c i 4烷亞 磺醯基(視需要羥氰基取代),Ci-4垸磺醯胺撐, Crt-d-垸氧羰基,或選自四唑基,晖二唑(視需要 涇鹵呆基取代),噻二唑基(視需要羥鹵苯基或 C- 4垸基取代),呋喃基,吡咯基或茏并眯唑基 ,或基團COOR3,其中烷基(視需要經茏 基,Cl-4L综氧截基或鹵素),Cz-Λ -烯基,C2-4块 基,茏基,氫或一無機或有機陽離子基團; 或基薄!-CiRs)=N-R3;其中R5是氫,Ct-4垸基及 Re是羥基,C^-4 -二烷胺基或Ct-4烷氧基,或基 團-CONR7R8,其中R7是氫,烷基,R8是氫, Ck烷氧基,C^-4烷基,胺基,(:τ-4酵胺基, C,-4烷氧羰基,苄基,Ct-4-烷亞胺基或鹵苯基 η是 0,1或2 ; 及與金覉鹽形成的錯合物,以及與鹼所成的鹽(當化合 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) n 1n^ ntn 1^1 —Bui V^ ^mn Inti n (請先閲讀背面之注意事項再填寫本頁) 3iS8% 4 本 A8 B8 C8 D8 年Λ β 補充 申請專利範圍 2 . 3 . 物為酸)及與酸所成的鹽(當化合物為鹼),前題是在 Y為氫旦 i ) z為羧基,甲氧羰基或乙氧羰基時,環A並非未經 取代的吡啶基或吡哄基;而 y ii)在z為羧基且η是0時,ί\不是2 -氯-4-吡啶基, 6- (2 -二乙胺乙氧基)-3-吡啶基或2 -吡啶基。 一種殺真菌姐合物,其含有與展業上可接受的稀釋劑或 截體摻和的根據申請專利範圍第1項之化合物。 一種於植物感染部位或可能感染部位克服植物病原性真 菌的方法,其包括於該部位使用根據申請專利範圍第1 頂之化合物。 1 — n HI —i— n ft - l m ____ In - m T ·ν5 (請先閲讀背面之注意事1再填寫本頁) 經濟部中央標隼局員工消費合作社印製 本紙張尺度逋用中國國家橾準(CNS ) Α4规格(210Χ297公釐)
TW084102527A 1994-03-18 1995-03-16 TW318829B (zh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9405347A GB9405347D0 (en) 1994-03-18 1994-03-18 Fungicides

Publications (1)

Publication Number Publication Date
TW318829B true TW318829B (zh) 1997-11-01

Family

ID=10752091

Family Applications (1)

Application Number Title Priority Date Filing Date
TW084102527A TW318829B (zh) 1994-03-18 1995-03-16

Country Status (16)

Country Link
US (1) US5756524A (zh)
EP (1) EP0750611B1 (zh)
JP (1) JPH09510471A (zh)
CN (1) CN1143954A (zh)
AT (1) ATE168099T1 (zh)
AU (1) AU688473B2 (zh)
BR (1) BR9507105A (zh)
CZ (1) CZ269096A3 (zh)
DE (1) DE69503365T2 (zh)
GB (1) GB9405347D0 (zh)
HU (1) HU214292B (zh)
IL (1) IL113027A0 (zh)
PL (1) PL316289A1 (zh)
TW (1) TW318829B (zh)
WO (1) WO1995025723A1 (zh)
ZA (1) ZA952205B (zh)

Families Citing this family (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3964478B2 (ja) * 1995-06-30 2007-08-22 エーザイ・アール・アンド・ディー・マネジメント株式会社 ヘテロ環含有カルボン酸誘導体及びそれを含有する医薬
DE19531813A1 (de) * 1995-08-30 1997-03-06 Basf Ag Bisphenylamide
US5811428A (en) * 1995-12-18 1998-09-22 Signal Pharmaceuticals, Inc. Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions
CA2230894A1 (en) * 1995-09-01 1997-03-13 Signal Pharmaceuticals, Inc. Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions
GB9518993D0 (en) * 1995-09-16 1995-11-15 Agrevo Uk Ltd Fungicides
GB9518994D0 (en) * 1995-09-16 1995-11-15 Agrevo Uk Ltd Fungicides
AU1730497A (en) * 1996-02-17 1997-09-02 Agrevo Uk Limited Fungicidal 1,2,4-oxadiazoles and analogues
DE19622270A1 (de) * 1996-06-03 1997-12-04 Basf Ag Pyrimidin-4-carbonsäureamide
DE19629828A1 (de) 1996-07-24 1998-01-29 Bayer Ag Carbanilide
US6022884A (en) * 1997-11-07 2000-02-08 Amgen Inc. Substituted pyridine compounds and methods of use
US6191170B1 (en) * 1998-01-13 2001-02-20 Tularik Inc. Benzenesulfonamides and benzamides as therapeutic agents
DE69920923T2 (de) * 1998-07-24 2005-10-20 Teijin Ltd. Anthranilsäurederivate
US7183278B1 (en) 1998-11-04 2007-02-27 Meiji Seika Kaisha, Ltd. Picolinamide derivative and harmful organism control agent comprising said picolinamide derivative as active component
GB9824579D0 (en) 1998-11-10 1999-01-06 Novartis Ag Organic compounds
EP1516875A1 (en) * 1999-07-20 2005-03-23 Dow AgroSciences LLC Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
FR2803592A1 (fr) 2000-01-06 2001-07-13 Aventis Cropscience Sa Nouveaux derives de l'acide 3-hydroxypicolinique, leur procede de preparation et compositions fongicides les contenant.
JP2003520854A (ja) 2000-01-27 2003-07-08 サイトビア インコーポレイテッド カスパーゼのアクチベーターおよびアポトーシスのインデューサーとしての置換ニコチンアミドおよび類似物およびそれらの使用
MY138097A (en) * 2000-03-22 2009-04-30 Du Pont Insecticidal anthranilamides
GB0101996D0 (en) * 2001-01-25 2001-03-14 Syngenta Participations Ag Organtic compounds
EP1275653A1 (en) * 2001-07-10 2003-01-15 Bayer CropScience S.A. Oxazolopyridines and their use as fungicides
AR037233A1 (es) 2001-09-07 2004-11-03 Euro Celtique Sa Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento
AR036873A1 (es) * 2001-09-07 2004-10-13 Euro Celtique Sa Piridinas aril sustituidas a, composiciones farmaceuticas y el uso de las mismas para la preparacion de un medicamento
ITMI20012430A1 (it) * 2001-11-19 2003-05-19 Isagro Spa Composizioni a base di sali rameici sali rameici e loro utilizzo per il controllo di fitopatogeni
AU2002350172A1 (en) * 2001-12-07 2003-06-23 Eli Lilly And Company Substituted heterocyclic carboxamides with antithrombotic activity
US7176310B1 (en) * 2002-04-09 2007-02-13 Ucb Sa Pyrimidinecarboxamide derivatives and their use as anti-inflammatory agents
PA8578101A1 (es) * 2002-08-13 2004-05-07 Warner Lambert Co Derivados de heterobiarilo como inhibidores de metaloproteinasa de la matriz
JP4896518B2 (ja) * 2002-12-13 2012-03-14 ワイエム・バイオサイエンシズ・オーストラリア・ピーティーワイ・リミテッド ニコチンアミド系キナーゼ阻害薬
EP1569907B1 (en) * 2002-12-13 2016-03-09 YM BioSciences Australia Pty Ltd Nicotinamide-based kinase inhibitors
AU2003291839B2 (en) * 2002-12-13 2009-01-22 Ym Biosciences Australia Pty Ltd Nicotinamide-based kinase inhibitors
DE10349502A1 (de) * 2003-10-23 2005-05-25 Bayer Cropscience Ag 1,3-Dimethylbutylcarboxanilide
UA89035C2 (ru) 2003-12-03 2009-12-25 Лео Фарма А/С Эфиры гидроксамовых кислот и их фармацевтическое применение
DE102005009457A1 (de) * 2005-03-02 2006-09-07 Bayer Cropscience Ag Verfahren zum Herstellen von Alkylaniliden
CA2601468A1 (en) * 2005-03-14 2006-09-21 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
BRPI0609685A2 (pt) 2005-04-06 2010-04-20 Hoffmann La Roche compostos, processo para a sua manufatura, composições farmacêuticas que os compreendem, método para tratamento e/ou profilaxia de enfermidades que estão associados com a modulação de receptores de cb1, e utilização dos mesmos
EP1931642A4 (en) * 2005-09-15 2011-06-01 Orchid Res Lab Ltd NEW PYRIMIDINE CARBOXAMIDES
PE20110118A1 (es) * 2005-10-04 2011-03-08 Aventis Pharma Inc Compuestos de pirimidina amida como inhibidores de pgds
WO2007043677A1 (en) 2005-10-14 2007-04-19 Sumitomo Chemical Company, Limited Hydrazide compound and pesticidal use of the same
ATE507205T1 (de) * 2006-12-11 2011-05-15 Genetics Co Inc Aromatische 1,4-di-carboxylamide und deren verwendung
JP2008280336A (ja) * 2007-04-11 2008-11-20 Sumitomo Chemical Co Ltd アミド化合物の製造方法
JP2008280340A (ja) * 2007-04-12 2008-11-20 Sumitomo Chemical Co Ltd ヒドラジド化合物及びそれを含有する有害節足動物防除剤
JP2008280339A (ja) * 2007-04-12 2008-11-20 Sumitomo Chemical Co Ltd ヒドラジド化合物及びそれを含有する有害節足動物防除剤
US8748623B2 (en) 2009-02-17 2014-06-10 Syntrix Biosystems, Inc. Pyridinecarboxamides as CXCR2 modulators
AR081626A1 (es) 2010-04-23 2012-10-10 Cytokinetics Inc Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos
AR081331A1 (es) 2010-04-23 2012-08-08 Cytokinetics Inc Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos
WO2011133920A1 (en) 2010-04-23 2011-10-27 Cytokinetics, Inc. Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
EP2608672B1 (en) * 2010-08-23 2020-12-16 Syntrix Biosystems, Inc. Aminopyridine- and aminopyrimidinecarboxamides as cxcr2 modulators
US8410107B2 (en) 2010-10-15 2013-04-02 Hoffmann-La Roche Inc. N-pyridin-3-yl or N-pyrazin-2-yl carboxamides
US8669254B2 (en) 2010-12-15 2014-03-11 Hoffman-La Roche Inc. Pyridine, pyridazine, pyrimidine or pyrazine carboxamides as HDL-cholesterol raising agents
KR101939710B1 (ko) 2011-12-21 2019-01-17 노비라 테라퓨틱스, 인코포레이티드 B형 간염의 항바이러스성 제제
KR20210081451A (ko) 2012-08-28 2021-07-01 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 설파모일-아릴아미드 및 b형 간염 치료제로서의 그 용도
WO2014131847A1 (en) 2013-02-28 2014-09-04 Janssen R&D Ireland Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b
PT2981536T (pt) 2013-04-03 2017-08-09 Janssen Sciences Ireland Uc Derivados de n-fenil-carboxamida e sua utilização como medicamentos para o tratamento da hepatite b
JO3603B1 (ar) 2013-05-17 2020-07-05 Janssen Sciences Ireland Uc مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي
JP6441315B2 (ja) 2013-05-17 2018-12-19 ヤンセン・サイエンシズ・アイルランド・ユーシー スルファモイルチオフェンアミド誘導体およびb型肝炎を治療するための医薬品としてのその使用
WO2015011281A1 (en) 2013-07-25 2015-01-29 Janssen R&D Ireland Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis b
US8969365B2 (en) 2013-08-02 2015-03-03 Syntrix Biosystems, Inc. Thiopyrimidinecarboxamides as CXCR1/2 modulators
US10561676B2 (en) 2013-08-02 2020-02-18 Syntrix Biosystems Inc. Method for treating cancer using dual antagonists of CXCR1 and CXCR2
US10046002B2 (en) 2013-08-02 2018-08-14 Syntrix Biosystems Inc. Method for treating cancer using chemokine antagonists
DK3060547T3 (en) 2013-10-23 2018-01-15 Janssen Sciences Ireland Uc CARBOXAMIDE DERIVATIVES AND USE THEREOF AS MEDICINES FOR TREATMENT OF HEPATITS B
WO2015060378A1 (ja) * 2013-10-25 2015-04-30 日本曹達株式会社 アミノピリジン誘導体および農園芸用殺菌剤
US10392349B2 (en) 2014-01-16 2019-08-27 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
CA2936947A1 (en) 2014-02-05 2015-08-13 Novira Therapeutics, Inc. Combination therapy for treatment of hbv infections
US11078193B2 (en) 2014-02-06 2021-08-03 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
KR102579996B1 (ko) * 2015-05-13 2023-09-18 니혼노야쿠가부시키가이샤 안트라닐산 에스테르 화합물 또는 이의 염류 및 해당 화합물을 함유하는 농원예용 살균제 및 이의 사용 방법
US10875876B2 (en) 2015-07-02 2020-12-29 Janssen Sciences Ireland Uc Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
JP2019511542A (ja) 2016-04-15 2019-04-25 ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー カプシド集合阻害剤を含む組み合わせ及び方法
AU2019235522A1 (en) 2018-03-14 2020-09-03 Janssen Sciences Ireland Unlimited Company Capsid assembly modulator dosing regimen
CN110746407A (zh) * 2018-07-23 2020-02-04 南京农业大学 一种含苯并咪唑基团的酰胺类衍生物及其制备方法与应用
US11096931B2 (en) 2019-02-22 2021-08-24 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases
AU2020269897A1 (en) 2019-05-06 2021-10-14 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2417216A1 (de) * 1974-04-09 1975-11-06 Basf Ag Fungizide
GB1563664A (en) 1977-01-06 1980-03-26 Sumitomo Chemical Co N-benzoylanthranilates processes for producing them and compositions containing them

Also Published As

Publication number Publication date
EP0750611A1 (en) 1997-01-02
DE69503365T2 (de) 1999-01-07
WO1995025723A1 (en) 1995-09-28
HU214292B (hu) 1998-03-02
ZA952205B (en) 1995-10-31
PL316289A1 (en) 1997-01-06
AU1898195A (en) 1995-10-09
DE69503365D1 (de) 1998-08-13
MX9603735A (es) 1997-12-31
HU9602547D0 (en) 1996-11-28
US5756524A (en) 1998-05-26
ATE168099T1 (de) 1998-07-15
CN1143954A (zh) 1997-02-26
GB9405347D0 (en) 1994-05-04
EP0750611B1 (en) 1998-07-08
BR9507105A (pt) 1997-09-09
AU688473B2 (en) 1998-03-12
IL113027A0 (en) 1995-06-29
CZ269096A3 (en) 1996-12-11
HUT74778A (en) 1997-02-28
JPH09510471A (ja) 1997-10-21

Similar Documents

Publication Publication Date Title
TW318829B (zh)
CA2453623C (en) 6-aryl-4-aminopicolinates and their use as herbicides
JP4986977B2 (ja) 4−アミノピコリネート類及び除草剤としてのそれらの使用
AU2009313134B8 (en) Novel halogen-substituted compounds
JP6677637B2 (ja) 有害生物防除的に活性な、硫黄含有置換基を有する二環式または三環式複素環
TWI596088B (zh) 4-胺基-6-(經取代的苯基)吡啶甲酸酯及6-胺基-2-(經取代的苯基)-4-嘧啶羧酸酯之芳烷酯以及其等作為除草劑之用途
KR101006363B1 (ko) 가교 고리형 아민 화합물 및 유해 생물 방제제
US5326766A (en) 4-(2-(4-(2-pyridinyloxy)phenyl)ethoxy)quinazoline and analogues thereof
UA56987C2 (uk) Похідні фенілоцтової кислоти, засіб для боротьби з шкідниками та проміжні сполуки
AU2002322777A1 (en) 6-aryl-4-aminopicolinates and their use as herbicides
EA018801B1 (ru) Гербицидные соединения
AU2012209278A1 (en) Arylalkyl esters of 4-amino-6-(substituted phenyl)picolinates and 6-amino-2-(substituted phenyl)-4-pyrimidinecarboxylates and their use as herbicides
WO2007066601A1 (ja) ピリダジン化合物及びその用途
BR112014019622B1 (pt) Composto, seus usos, composição pesticida, material de propagação de plantas tratado e com-posições farmacêuticas
US4775762A (en) Novel (1H-1,2,3-triazol-1-yl)pyridines
CN109071495A (zh) 农业化学品
JP3694051B2 (ja) 1−ピリジルテトラゾリノン誘導体および除草剤
US4588735A (en) Fungicidal (trihalophenoxy or trihalophenthio) alkylaminoalkyl pyridines and pyrroles
KR20000070702A (ko) 살진균제로서 피리딘 환 상에 카복실산 유도체를 갖는 2-메톡시이미노-2-(피리디닐옥시메틸)페닐 아세트아미드
JPH03181480A (ja) ヘトアリール置換ピリジニルピリミジン誘導体
JP7244490B2 (ja) 殺有害生物的に活性なチオフェン誘導体
JP7202371B2 (ja) 殺有害生物的に活性なピラゾール誘導体
KR100191182B1 (ko) 제초활성을갖는피라졸유도체,그것의제법및용도
JPH09328483A (ja) 除草性イソオキサゾリン誘導体
JPH03133982A (ja) ピリジン誘導体及び好ましくない植物の成長を抑止する方法