CN1143954A - 杀真菌化合物 - Google Patents

杀真菌化合物 Download PDF

Info

Publication number
CN1143954A
CN1143954A CN95192131A CN95192131A CN1143954A CN 1143954 A CN1143954 A CN 1143954A CN 95192131 A CN95192131 A CN 95192131A CN 95192131 A CN95192131 A CN 95192131A CN 1143954 A CN1143954 A CN 1143954A
Authority
CN
China
Prior art keywords
coome
pyridyl
meo
group
compound
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
CN95192131A
Other languages
English (en)
Inventor
P·D·里奥丹
I·K·波迪
S·E·欧斯本
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience Ltd Great Britain
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
Publication of CN1143954A publication Critical patent/CN1143954A/zh
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/60—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
    • 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
    • A01N43/02—Biocides, 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
    • A01N43/04—Biocides, 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
    • A01N43/06—Biocides, 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
    • A01N43/10—Biocides, 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
    • 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
    • A01N43/34—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
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—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
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/713—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
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—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
    • 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
    • A01N43/90—Biocides, 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
    • 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
    • A01N47/10—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
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • A01N59/20—Copper
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • 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
    • C07D213/60—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
    • 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
    • C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic 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
    • C07D233/56—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic 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
    • C07D239/28—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic 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
    • C07D239/28—Heterocyclic 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
    • C07D239/30—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic 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
    • C07D239/28—Heterocyclic 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic 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
    • C07D239/28—Heterocyclic 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic 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
    • C07D239/28—Heterocyclic 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic 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
    • C07D239/28—Heterocyclic 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic 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
    • C07D239/28—Heterocyclic 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic 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
    • C07D241/14—Heterocyclic 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
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic 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
    • C07D333/26—Heterocyclic 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Inorganic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (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)

Abstract

式I化合物X是O或S；A是含有至少一个氮原子的6元杂芳基，它任由一个或多个R2基团取代；R1是烷基、环烷基、环烯基、链烯基、炔基、或氨基，(各基团任选被取代)，Y′-X-、卤素、氰基、硝基、酰基、酰氧基、任选取代的杂环基或任选取代的苯基；或两个相邻基团和与之相连的碳原子一起可以形成任选取代的苯并环；R2具有与R1相同的含意或两个相邻基团和与之相连的碳原子一起可以形成任选取代的杂环；Y是烷基、环烷基、环烯基、链烯基或炔基，各基团任选被取代，氢或酰基；Y1具有与Y相同的含意或是任选取代的苯基或任选取代的杂环基；Z是C(=X1)-X2-R3、氰基、硝基、氨基、酰基、任选取代的杂环基、-C(R5)=N-OR6或-C(R5)=N-NR6R7；R3是烷基、环烷基、环烯基、链烯基、炔基、苯基或杂环基，各基团任选被取代，氢或无机或有机阳离子基团；X1和X2，它们可以相同或不同，为O或S；R5、R6和R7，它们可以相同或不同，是烷基、环烷基、环烯基、链烯基、炔基、苯基或杂环基，各基团任选被取代，或是氢或R6和R7和与之相连的原子一

Description

杀真菌化合物
发明领域
本发明涉及新的用作杀真菌剂的邻氨基苯甲酸衍生物。
现有技术
GB 1,563,664和日本专利公开53130655中公开了杀真菌的邻氨基苯甲酸酯。我们发现某些新颖的邻氨基苯甲酸衍生物也具有有价值的杀真菌活性并且还具有优于上述文献中公开的化合物的优点。
发明内容
本发明提供式I化合物
Figure A9519213100041
X是O或S；A是含有至少一个氮原子的6元杂芳基，它任由一个或多个R2基团取
代；R1是烷基、环烷基、环烯基、链烯基、炔基、或氨基，(各基团任选被
取代)，Y′-X-、卤素、氰基、硝基、酰基、酰氧基、任选取
代的杂环基或任选取代的苯基；或两个相邻基团和与之相连的碳原
子一起可以形成任选取代的苯并环；R2具有与R1相同的含意或两个相邻基团和与之相连的碳原子一起可以
形成任选取代的杂环；Y是烷基、环烷基、环烯基、链烯基或炔基，各基团任选被取代，氢或
酰基；Y1具有与Y相同的含意或是任选取代的苯基或任选取代的杂环基；Z是C(＝X1)-X2-R3、氰基、硝基、氨基、酰基、任选取代的
杂环基、-C(R5)＝N-OR6或-C(R5)＝N-NR6R7；R3是烷基、环烷基、环烯基、链烯基、炔基、苯基或杂环基，各基团任
选被取代，氢或无机或有机阳离子基团；X1和X2，它们可以相同或不同，为O或S；R5、R6和R7，它们可以相同或不同，是烷基、环烷基、环烯基、链烯
基、炔基、苯基或杂环基，各基团任选被取代，或是氢或R6和R7
和与之相连的原子一起可以形成环；且n是0至4，与金属盐的配合物，以及当化舍物是酸时与碱形成的盐和当化合物是碱
时与酸形成的盐，其条件是当Y是氢且：i)是Z是羧基、甲氧羰基或乙氧羰基时，环A不是未取代的吡啶基或吡嗪基；和ii)当Z是羧基和n是0时，A不是2-氯-3-吡啶基、6-(2-二乙基氨基乙氧基)-3-吡啶基或2-吡啶基。
烷基优选具有1至20个，例如1至6个碳原子。链烯基和炔基一般具有3至6个碳原子。环烷基或环烯基优选具有3至8个碳原子。
当取代基存在于任何烷基、环烷基、环烯基、链烯基或炔基部分时，它包括氢、叠氮基、氰基、任选取代的烷氧基、任选取代的烷硫基、羟基、硝基、任选取代的氨基、酰基、酰氧基、任选取代的苯基、任选取代的杂环基、任选取代的苯氧基和任选取代的杂环氧基。
环烷基或环烯基也可以被烷基取代。
当取代基存在于任何苯基上时。它通常是一个或多个如R1定义的相同基团。
术语杂环基包括芳杂环和非芳杂环。杂环基一般是含有最多4个选自氮、氧和硫的杂原子的5，6或7元环。杂环基的实例是呋喃基、噻吩基、吡咯基、吡咯啉基、吡咯烷基、咪唑基、二氧戊环基、噁唑基、噻唑基、咪唑基、咪唑啉基、咪唑烷基、吡唑基、吡唑啉基、吡唑烷基、异噁唑基、异噻唑基、噁二唑基、***基、噻二唑基、吡喃基、吡啶基、哌啶基、二噁烷基、吗啉代、二噻烷基、硫代吗啉代、哒嗪基、嘧啶基、吡嗪基、哌嗪基、三嗪基、噻唑啉基、苯并咪唑基、四唑基、苯并噁唑基、咪唑并吡啶基、1，3-苯并噁嗪基、1，3-苯并噻嗪基、噁唑并吡啶基、苯并呋喃基、喹啉基、喹唑啉基、喹喔啉基、四氢噻吩砜基、二氢喹唑啉基、苯并噻唑基、邻苯二甲酰亚氨基、苯并呋喃基、氮杂_基、噁氮杂_基、噻氮杂_基、二氮杂_基和苯并二氮杂_基。
杂环基本身可以被取代，例如被苯基取代。
氨基可以被例如一个或两个任选取代的烷基或酰基取代，或两个取代基可以形成环，优选5至7元环，该环可以被取代或可以含有其它杂原子，例如吗啉、硫代吗啉或哌啶。
术语酰基包括含硫和磷的酸以及羧酸的残基。因此酰基的实例是-COR5、-COOR5、-CXNR5N6、-CON(R5)OR6、-COONR5R6、-CON(R5)NR6R7、-COSR5、CSSR5、-S(O)pR5、-S(O)2OR5、-S(O)pNR5R6、-P(＝X)(OR5)(OR6)、-CO-COOR5，其中R5、R6和R7如前面所定义，或R6和R7和与之相连的原子-起形成环，P是1或2且X是0或3。
一般优选A是吡啶(特别是3-吡啶基)、嘧啶(特别是5-嘧啶基)或吡嗪环。也可以是例如四嗪、哒嗪或三嗪环。
R2优选选自卤素和烷氧基，特别是甲氧基。
R1优选选自卤素，特别是氟，和烷基，特别是甲基。
Z优选C(＝X1)-X2-X3。X1和X2均优选是氧且R3一般是烷基、链烯基或炔基，各基团任选被取代，且特别优选甲基。
Y优选氢、烷基，特别是甲基或酰基，特别是烷酰基或烷氧羰基。
X优选0。
n优选0。
本发明化合物配合物一般由式Man2的盐形式，其中M是二价金属阳离子，例如铜、锰、钴、镍、铁或锌且An是阴离子，例如氯化物、硝酸盐或硫酸盐。
本发明化合物具有广谱的防治半知菌类、子囊菌纲、藻菌纲和担子菌纲源的病原菌的活性，特别是防治植物真菌病害，例如，白粉病且特别是大麦白粉病(Erysiphe graminis)、黄瓜白粉病(Erysiphecichoracaerum)和葡萄霜霉病(Plasmopara viticola和Uncinulanecator)、稻瘟病(Pyricularia orgzae)、麦类眼斑病(Pseudocercosporella herpotrichoides)、稻纹枯病(Pelliculariasasakii)、灰霉病(Botrytis cinerea)、小麦叶锈病(Pucciniarecondita)、蕃茄或马铃薯晚疫病(Phytophthora infestans)、苹果黑星病(Ventaria inaegualis)和颖枯病(Leptosphaeria nodorum)。某些化合物可能只对少数病原菌有活性而其它化合物可能具有广谱的活性。
某些新颖的式I化合物具有弱的农药活性，但还是有作为中间体的实用性，且这些化合物也构成本发明的一方面。
本发明化合物一般加工成用作杀菌剂的常规组合物。这些组合物可以含有一种或多种附加的农药，例如已知拥有除草、杀菌、杀虫、杀螨或杀线虫性能的化合物。
本发明组合物中的稀释液或载体可以是固体或液体，任选与表面活性剂结合，例如分散剂、乳化剂或润湿剂。适合的表面活性剂包括阴离子化合物如羧酸盐，例如长链脂肪酸的金属羧酸盐；N-酰基肌氨酸盐；磷酸与脂肪醇乙氧化物的单或二酯或这些酯的盐，脂肪醇硫酸盐如十二烷基硫酸钠、十八烷基硫酸钠或十六烷基硫酸钠；乙氧基脂肪醇硫酸盐；乙氧基烷基酚硫酸盐；木质素磺酸盐；石油磺酸盐；烷基芳基磺酸盐如烷基苯磺酸盐或低级烷基萘磺的盐，例如，丁基萘磺酸盐；磺化萘-甲醛缩舍物的盐；磺化酚-甲醛缩合物的盐；或更复杂的磺酸盐如酰胺磺酸盐，例如油酸和牛磺酸的磺化的缩合产物或磺化琥珀酸二烷基酯，例如，二辛基琥珀酸酯的磺酸钠。非离子表面活性剂包括脂肪酸酯、脂肪醇、脂肪酸酰胺或脂肪一烷基或链烯基取代酚与环氧乙烷的缩合产品，多元醇醚的脂肪酸酯，例如，失水山梨醇脂肪酸酯类，这些酯与环氧乙烷的缩合产品，例如，聚氧乙烯失水山梨醇脂肪酸酯，环氧乙烷与环氧丙烷的嵌段共聚物，炔二醇如2，4，7，9-四甲基-5-癸炔-4，7-二醇，或乙氧基炔二醇。阳离子表面活性剂的实例包括，例如，脂族单、二或多胺的乙酸盐、环烷酸盐或油酸盐；含氧的胺如氧化胺或聚氧乙烯烷基胺；羧酸与二或多胺缩合制备的酰胺连接的胺；或季胺盐。
本发明组合物可以是农药制剂领域已知的任何形式，例如，溶液、分散液、水乳剂、喷粉剂、拌种剂、熏蒸剂、烟剂、可分散粉剂、乳油或颗粒剂。而且它可以以适合的形式直接施用或作为需要在施用前用适合量的水或其它稀释剂稀释的浓缩物或初级组合物。
作为分散液，本发明组合物包含分散于液体介质(优选是水)中的本发明化合物。提供给用户可以用水稀释形成具有所需浓度的分散液的初级组合物，通常是方便可行的。初级组合物可以下列任一形式提供。它可以是一种可分散溶液，该可分散溶液包括溶于加有分散剂的与水可互混溶剂中的本发明化合物。另一种选择包含与分散剂结合的细研磨粉状的本发明化合物，且它们紧密与水混合给出一种糊剂或膏剂，该糊剂或膏剂如果需要可以加入水包油乳液中，以给出活性成分在水油乳液中的分散液。
乳油包含溶于能和水互混溶剂中并有乳化剂的本发明化合物，且当它与水混合时形成乳液。
喷粉剂包含紧密与固体粉状稀释剂例如高岭土混合的本发明化合物。
颗粒固体包含与那些可以用于喷粉剂中的类似的稀释剂结合的本发明化合物，但此混合物由已知方法造粒。另一种选择是，它包含吸附或吸收在前-颗粒稀释剂例如漂白土、硅镁土或石灰硬渣上的活性成分。
可湿性粉剂通常含有与适合的表面活性剂和惰性粉状稀释剂如陶土掺和的活性成分。
另一种适合的浓缩物，特别是当产品为固体时，是流动性悬浮制剂，它通过将化合物与水、润湿剂和悬浮剂一起研磨而形成。
本发明组合物中的活性成分浓度优选为1至30％(重量)，特别是5至30％(重量)。在初级组合物中，活性成分的量可以在宽范围内变化，且可以是例如组合物的5至95％(重量)。
本发明化合物可以以已知的方式制备，例如使式II化合物
与式III化合物反应，
Figure A9519213100082
其中Q是离去基，优选卤素，且特别是氯，以给出式I化合物，其中X是0且Y是氢，和如果需要，以已知的方式改变此化合物以给出其中X和/或Y具有其它所需含意的其它化舍物，且如果需要，以已知的方式改变式I化合物以给出其中R1、R2和Z具有其它含意的化合物。
化合物II和III间的反应通常在碱如有机叔胺存在下和优选在溶剂如醚存在下进行。
式II和III化合物或是已知的或可以以已知方式制备。
所得式I化合物可以以已知方式改变以给出其中基团之一被改变成其它所需基团的其它式I化合物。
例如，酯可以以已知方式转化成游离酸或盐。
硫代基团可以用适合的氧化剂例如间氯过苯甲酸氧化以给出亚磺酰基和磺酰基。
羰基可以通过已知方式，例如，使用Lawesson试剂或五硫化磷硫代而转化成硫代羰基。
A环上的烷基磺酰基可以通常与适合的羟基或巯基化合物反应而被适合的亲核试剂如芳氧或芳硫基代替。
本发明用下列实施例作说明。分离出的新化合物的结构由元素分析和/或其它适宜的分析确证。温度为0℃。
实施例1
将三乙胺(28.4g)加入到6-氯烟酸(40g)的无水二氯甲烷(900ml)溶液中。混合物在冰浴中冷却并滴加氯甲酸甲酯(26.8g)。混合物在室温下搅拌过夜，依次用水、碳酸氢钠水溶液和盐水洗涤。有机相经硫酸镁干燥，过滤并蒸发，给出6-氯烟酸甲酯。
将10g此产物加入到甲醇钠(由1.61g钠和100ml无水甲醇获得)中。混合物加热回流3小时并让其在室温下静置过夜。加入氢氧化钾水溶液(10g于30ml水中)并将此混合物加热回流8小时。放置于室温下过夜，蒸发并将残留物加入水(120ml)中。混合物用盐酸酸化至pH3。过渡沉淀物并干燥给出6-甲氧基烟酸，mp.175-177°。
将此酸(6g)与过量的亚硫酰氯加热回流2小时。将混合物冷却，蒸发并将残留物(包含粗产品6-甲氧基烟酰氯)溶于无水四氢呋喃(10ml)中。将此溶液滴加到邻氨基苯甲酸甲酯(6.22g)和三乙胺(7.92g)的无水四氢呋喃(200ml)溶液中。将混合物在室温下搅拌过夜，蒸发并用乙酸乙酯萃取。萃取液用水洗涤，干燥并蒸发，残留物用硅胶柱色谱纯化，给出N-(6-甲氧基烟酰基)邻氨基苯甲酸甲酯m.p.121-3°(化合物1)
以相似的方式获得N-(2-甲基硫代-5-嘧啶羰基)邻氨基苯甲酸甲酯，m.p.166-8°(化合物1a)
实施例2
将氢化钠(0.15g的60％油溶液)加入到已在冰浴中冷却的由实施例1得的化合物1(1g)的无水四氢呋喃(25ml)溶液中。将混合物搅拌20分钟，然后加入甲基碘(0.44ml)。将混合物在室温下搅拌48小时，蒸发并用乙酸乙酯萃取。萃取液依次用水和盐水洗涤，经硫酸镁干燥并蒸发。残留物用硅胶柱色谱提纯，给出N-(6-甲氧基烟酰)-N-甲基邻氨基苯甲酸甲酯，m.p.68-70°(化合物2)
实施例3
向实施例2得到的化合物2(0.6g)的乙醇(20ml)溶液中加入氯化铜(II)(0.134g)。让混合物静置过夜，蒸发并将残留物用乙酸乙酯研制，给出双-〔N-(6-甲氧基烟酰)-N-甲基邻氨基苯甲酸甲酯〕氯化铜(II)配合物，m.p.196-8°(化合物3)
实施例4
伴随搅拌将间氯过苯甲酸(13.7g)加入到化合物1a(6g)的二氯甲烷溶液中。将此混合物在室温下搅拌过夜，加入硫酸钠并用二氯甲烷萃取。萃取液经处理，给出N-(2-甲基磺酰基-5-嘧啶羰基)邻氨基苯甲酸甲酯，m.p.187-9°(化合物4)
实施例5
将氢化钠(0.24g的60％油分散液)加入到溶于无水二甲基甲酰胺(20ml)中的2-巯基吡啶(0.33g)溶液中。将此混合物在室温下搅拌半小时。搅拌下滴加化合物4(1g)的无水二甲基甲酰胺(20ml)溶液。混合物在室温下搅拌过夜。将其冷却并用甲醇停止反应。将混合物倒入水中，并用稀盐酸酸化。收集沉淀物，用二氯甲烷溶解，将溶液用盐水洗涤并蒸发，给出N-〔2-(2-吡啶硫代)-5-嘧啶羰基〕-邻氨基苯甲酸甲酯，m.p.145-147°(化合物5)
以相似的方式，采用碳酸钾作为碱来替代氢化钠，得到N-〔2-(4-甲氧基苯氧基)-5-嘧啶羰基〕邻氨基苯甲酸甲酯，其为油状物(化合物5a)。
实施例6
化合物1用等摩尔量的氢氧化钠水溶液加热，给出N-(6-甲氧基烟酰)邻氨基苯甲酸m.p.224-3°(化合物6)。
此化合物接下来再用氢氧化钠处理，给出N-(6-甲氧基烟酰)邻氨基苯甲酸钠，m.p.＞250°(化合物6a)。
实施例7
将Lawesson试剂(2，4-双4-甲氧基苯基)-1，3-二硫杂-2，4-二磷杂(diphosphetane)-2，4-二硫化物；5.09g)加入到化合物1(3g)的无水四氢呋喃(100ml)溶液中。将混合物在氮气下搅拌20小时。加入另外的Lawesson试剂(2.6g)，并将混合物加热回流13小时，蒸发并将残留物用硅胶柱色谱纯化，给出N-(6-甲氧基-3-吡啶硫代羰基)-邻氨基苯甲酸甲酯m.p.133-4°。(化合物7)
实施例8
以前面实施例公开的方式之一的相似方式，获得下列式I化合物。
Figure A9519213100111
化合物 (R1)n         Z          Y            A               m.p.(°)8     -              COOMe       H        6-EtO-3-吡啶基        150-29     -              COOEt       H        6-MeO-3-吡啶基        129-3010     -              COOEt       Me       6-MeO-3-吡啶基        91-211     -              COOMe       -CH2CN  6-MeO-3-吡啶基        油状物12     -              COOMe       -COOMe   6-MeO-3-吡啶基        胶状物13    3-Me            COOMe       H        6-MeO-3-吡啶基        111-214    5-Cl            COOMe       H        6-MeO-3-吡啶基        172-315    4，5-(MeO)2    COOMe       H        6-MeO-3-吡啶基        173-516     -              苄氧羰基    Me       6-MeO-3-吡啶基        110-317    5-Cl            COOMe       Me       6-MeO-3-吡啶基        89-9118 4，5-(MeO)2       COOMe       Me       6-MeO-3-吡定基        147-5019    5-Mes           COOMe       H        6-MeO-3-吡啶基        135-720    5-Mes           COOMe       Me       6-MeO-3-吡啶基        78-8021     -              CN          H        6-MeO-3-吡定基        163-622     -              CN          Me       6-MeO-3-吡啶基        90.5-323     -              COMe        H        6-MeO-3-比啶基        131.5-424     -              NO2        H        6-MeO-3-吡啶基        125-725     -              COOMe       H        5-MeO-2-吡嗪基        169-7026    6-Me            COOMe       H        6-MeO-3-吡啶基        102.5-527     -              COOMe       H        5-Cl-6-MeO-           165-6
                                        3-吡啶基化合物 (R1)n        Z         Y             A           m.p.(°)28    -             COOMe      Me       5-Cl-6-MeO-      110-2
                                      3-吡啶基29   6-Me           COOMe      Me       6-MeO-3-吡啶基   117.5-8.530    -             COOPri     H        6-MeO-3-吡啶基   107-931    -             COOMe      H        6-MeS-3-吡啶基   102.5-532    -             COOMe      Me       6-EtO-3-吡啶基   油状物33    -             COOMe      H        4，6-(MeO)2-    125-7
                                      5-嘧啶基34    -             COOMe      H        5，6-(MeO)2-    156-9
                                      2-吡嗪基35    -             COOMe      Me       3-吡啶基         86-836    -             SO2Me     H        6-MeO-3-吡啶基   148.5-50.537    -             SOMe       H        6-MeO-3-吡啶基   111-338   4-NO2         COOMe      Me       6-MeO-3-吡啶基   110-239    -             COOH       2-F-     6-MeO-3-吡啶基   195-7
                             苄基40   4-MeOCO        COOMe      Me       6-MeO-3-吡啶基   109-1241    -             CONH-OMe   H        6-MeO-3-吡啶基   152-342    -             COOMe      H        5-(3-噻吩基)-    149-50
                                      3-吡啶基43    -             COOMe      Me       6-NH2-3-吡啶基   119-2244    -             COOMe      H        6-PriO-3-吡啶基  15-745    -             四唑-5-基  Me       6-MeO-3-吡啶基   198-20046    -             SO2Me     Me       6-MeO-3-吡啶基   100-247    -             COOMe      H        6-MeCOO-3-吡啶基 109-1248   3-Cl           COOMe      H        6-MeO-3-吡啶基   106-1049    -             COOMe      H        4-Cl-2-吡啶基    158-6050    -             COOPr      H        6-MeO-3-吡啶基   107-951    -             COOBu      H        6-MeO-3-吡啶基   57-6052    -             COOPr      Me       6-MeO-3-吡啶基   81.5-453    -             COOBu      Me       6-MeO-3-吡啶基   72-654   3-Cl           COOMe      Me       6-MeO-3-吡啶基   84-7化合物(R1)n          Z           Y               A             m.p.(°)55    -              Me         6-MeO-3-吡啶基     147-5056    -            CHO            H          6-MeO-3-吡啶基     117-2057    -            COO-烯丙基     H          6-MeO-3-吡啶基     98-9.558   4-Cl          COOMe          Me         6-MeO-3-吡啶基     98-10059    -            COOMe       -CH2C≡CH 6-MeO-3-吡啶基     84.5-876O    -           
Figure A9519213100142
 H          6-MeO-3-吡啶基     124-3461    -           
Figure A9519213100143
  H          6-MeO-3-吡啶基     115-662   4-F           COOMe          H          6-MeO-3-吡啶基     125-663    -            COONH4        H          6-MeO-3-吡啶基     250-264   5，6-苯并     COOMe          H          6-MeO-3-吡啶基     157-6165   4-CF3        COOMe          H          6-MeO-3-吡啶基     139-4266    -            COOMe          4-CF3-    6-MeO-3-吡啶基     111-3
                               苄基67    -           
Figure A9519213100144
  H          6-MeO-3-吡啶基     102-468    -            COOMe          H          6-MeNH-3-吡啶基    187-8969    -            COOMe          2-Me-      6-MeO-3-吡啶基     112-4
                               苄基70    -            COOMe          4-MeO-     6-MeO-3-吡啶基     119-21
                               苄基71    -           
Figure A9519213100145
  H          6-MeO-3-吡啶基     165-772    -            COOMe          Me         2-吡啶基           80-273    -            COOMe          H          2-MeO-4-吡啶基     132-574    -            COOMe          H          5，6-Cl2-3-吡啶基 161-275    -            COO-N+Bu4   H          6-MeO-3-吡啶基     250-276    -            COOMe          H          2-Cl-3-吡啶基      120-177    -            COOMe          H          2-MeO-3-吡啶基     78-81化合物(R1)n        Z           Y               A            m.p.(°)78    -           CHO            Me         6-MeO-3-比啶基    83-479    -           CH＝N-OH       H          6-MeO-3-吡啶基    145-68O    -          
Figure A9519213100151
 H          6-MeO-3-吡啶基    87-981    -           I              H          6-MeO-3-吡啶基    140-282    -           COOMe          H          2-MeS-3-吡啶基    117-983    -           COOMe          H          5-Br-6-MeO-       164-5
                                         3-吡啶基84    -           COOMe          Me         5-Br-6-MeO-       112-4
                                         3-吡啶基185    -           COOMe          H          5-MeO-2-吡啶基    141-386    -           COOMe          H          6-Me-3-吡啶基     125-687  5-Me          COOMe          H          2-MeO-3-吡啶基    139-4088    -           COOC5H11     H          6-MeO-3-吡啶基    49-5289    -           COOCH2-       H          6-MeO-3-吡啶基    125-7
               COOMe90    -           COOCH2-       H          6-MeO-3-吡啶基    129-32
               C≡CH91    -           COOBui        H          6-MeO-3-吡啶基    81-392    -           COOMe          H          5-Ph-6-MeO-       159-61
                                         3-吡啶基93    -           COOMe          -CH2COOMe 6-MeO-3-吡啶基    油状物94    -           苄氧羰基       H          2-MeO-3-吡啶基    79-8095    -           CONHMe         H          6-MeO-3-吡啶基    162-496    -          
Figure A9519213100152
  Me         6-MeO-3-吡啶基    油状物97    -           Ph             H          6-MeO-3-吡啶基    107-998    -           5-(4-Cl-       H          6-MeO-3-吡啶基    193-7
               Ph)-1，3，4-
               噁二唑-2-基化合物(R1)n      Z               Y               A            m.p.(°)99    -          
Figure A9519213100161
                  6-MeO-3-吡啶基    203-5100  4-F，5-Me    COOMe            H          2-MeO-3-吡啶基    玻璃状物101   -           2-呋喃基         H          6-MeO-3-吡啶基    112-7102   -           COOCH2-         H          6-MeO-3-吡啶基    155-8
               CH2Cl103   -           COOMe            Me         2-MeO-3-吡啶基    油状物104  5-F          COOMe            H          6-MeO-3-吡啶基    125-6105   -           COOMe            烯丙基     6-MeO-3-吡啶基    油状物106   -           COOMe            乙酰基     6-MeO-3-吡啶基    油状物107   -           COOMe            苯甲酰基   6-MeO-3-吡啶基    117-8108   -           COOMe            3，4-MeO2-6-MeO-3-吡啶基    116-8
                                Ph-CH2CH2-109   -           COOMe            H          5-MeO-3-吡啶基    117-9110   -           COOMe            -CH2Ph    5-Cl-6-MeO-       126-8
                                           3-吡啶基1ll   -           COOMe            Me         5，6-Cl2-3-吡啶基103-4112   -           COOMe            H          5-Cl-6-MeS-       167-9
                                           3-吡啶基113   -           COOMe            H          5-Br-B-p吡啶基    122-3114   -           5-(4-Cl-         Me         6-MeO-3-吡啶基    188-91
               ph)-1，3，4-
               噁二唑-2-基115   -           COOMe            Me         4，6-(MeO)2-     111-3
                                           2-嘧啶基116  4-Me         COOMe            H          6-MeO-3-吡啶基    116-9117   -           COOMe            Me         5-MeO-2-吡啶基    82-4118   -           SO2NHMe         H          6-MeO-3-吡啶基    固体119  5-Me         COOMe            H          6-MeO-3-吡啶基    160-2120   -           COOMe            Me         5-MeO-3-吡啶基    60-2121  6-Cl         COOMe            H          6-MeO-3-吡啶基    160-2化合物(R1)n      Z           Y               A              m.p.(°)122   -           COOMe        H         5，6-(MeO)2-       155-7
                                      3-吡啶基123   -           5-(4-Cl-     H         6-MeO-3-吡啶基       215-7
               Ph)-1，3，4-
               噻二唑-2-基124   -          
Figure A9519213100171
H         6-MeO-3-吡啶基        140-2125  4-Cl         COOMe        H         2-(MeSO2)-          183-5
                                      5-嘧啶基126  5-NO2       COOMe        H         6-MeO-3-吡啶基       197-9127  3，5-Me2    COOMe        H         6-MeO-3-吡啶基       131-3128   -           COOMe        SO2Me    6-MeO-3-吡啶基       125-8129   -           COOMe        H         4-MeO-2-MeSO2-      187-90
                                      5-嘧啶基130   -           1-吡咯基     H         6-MeO-3-吡啶基       113-6131  4-Cl         COOMe        H         2-MeO-5-嘧啶基       175-7132  6-F          COOMe        H         6-MeO-3-吡啶基       177-9133  4-MeO        COOMe        H         6-MeO-3-吡啶基       164-5134   -           COOMe        -CH(Me)Ph 6-MeO-3-吡啶基       132-3135   -           COOMe        Me        5，6-(MeO)2-        110-2
                                      3-吡啶基136   -           COCH2OMe    H         6-MeO-3-吡啶基       110-2137   -           CONH2       H         6-MeO-3-吡啶基       224-8138   -           COOMe        H         4-Cl-6-[N-(2-MeOCO-  210-2
                                      Ph)NHCO]-2-吡啶基139   -           COOMe        H         4-MeO-6-[N-(2-MeO-   195-9
                                      CO-Ph)NHCO]-2-吡啶基140   -           COOMe        H         6-[N-(2-MeOCO-Ph)-   198-200
                                      NHCO]-3-吡啶基141   -           COOMe        H         6-CF3CH2O-3-吡啶基 173-4化合物(R1)n       Z              Y               A                m.p.(°)142   -           COOMe            H         2，5-(MeO)2-6-[N-     195-9
                                          (2-MeOCO-Ph)NHCO]-
                                          3-吡啶基143   -           COOMe            H         4，6-(EtO)2-          115-6
                                          2-吡啶基144   -           CONEt2          H         6-MeO-3-吡啶基         油状物145   -           CONHNH2         H         6-MeO-3-吡啶基         188-9146   -           CONH-            H         6-MeO-3-吡啶基         174-7
               N=CMe2147   -           COOMe            2-Me-     2-MeO-3-吡啶基         101-3
                                苄基148  5-NH2       COOMe            H         6-MeO-3-吡啶基         171-3149   -           COOMe            H         6-(2，3，4-Cl3-1-     183
                                          吡咯基)-3-吡啶基150   -                  6-MeO-3-吡啶基         113-5151   -           2-苯并            H        6-MeO-3-吡啶基         272-5
               咪唑基152   -          
Figure A9519213100182
       6-MeO-3-吡啶基         141-3153   -           CONHNH-          H         6-MeO-3-吡啶基         193-7
               COMe154   -           COO-烯丙基       H         5-Cl-6-MeO-            113-5
                                          3-吡啶基155   -           COOCH2-         H         5-Cl-6-MeO-            163-5
               C≡CH                      3-吡啶基156  3-F          COOMe            H         6-MeO-3-吡啶基         107-9157  5-OH         COOMe            H         6-MeO-3-吡啶基         203-5158  5-I          COOMe            H         6-MeO-3-吡啶基         154-6159  5-MeOCO      COOMe            H         6-MeO-3-吡啶基         155-6化合物 (R1)n     Z        Y                A                m.p.(°)160   5-MeCONH    COOMe     H           6-MeO-3-吡啶基        253-6161    -          COOMe     -CH(Me)-    6-MeO-3-吡啶基        134-5
                         COOMe162    -          COOMe     2-Me-       5-Cl-6-MeO-           油状物
                         苄基        3-吡啶基163    -          COOEt     H           5-Cl-6-MeO-           136-8
                                     3-吡啶基164    -          COOH      H           5-Cl-6-MeO-           247-50
                                     3-吡啶基165   5-MeSO2NH  COOMe     H           6-MeO-3-吡啶基        184-5166    -          COOMe     H           5-cyano-3-吡啶基      190-2167    -          COOMe     H           6-formyl-3-吡啶基     153-7168    -          CONH-     H           6-MeO-3-吡啶基        188-90
               (4-Cl-Ph)169    -          COOMe     H           5-Br-2-MeO-           180-2
                                     3-吡啶基170   4-Cl        COOMe     Me          2-MeO-5-嘧啶基        86-8171    -          COOMe     H           2-Cl-4-吡啶基         108-10172    -          COOMe     H           2-Cl-6-MeO-           144-5
                                     3-吡啶基173    -          COOMe     H           6-(2，3，4，5-Cl4-   289
                                     1-吡咯基)-3-吡啶基174    -          COONa     H           6-Cl-3-吡啶基         300175    -          COOMe     H           6-MeOCH2-3-吡啶基    117-8176    -          COOMe     H           5-氰基O-6-MeO-        247-50
                                     3-吡啶基177    -          5-Me-     H           6-MeO-3-吡啶基        143-5
               1，3，4-
             噁二唑-2-基178    -          COOMe     H           5-氰基O-6-Me2N-      190-2
                                     3-吡啶基179    -          COOMe     H           5-MeSO2O-3-吡啶基     149-51化合物 (R1)n      Z         Y             A               m.p.(°)180    -           COOMe      H       6-(2，3，5-Cl3-      134-5
                                   1-吡咯基)-3-吡啶基181    -           COOMe      H       6-MeOCO-3-吡啶基      141182    -           COOMe      H       5-PhCH2O-3-吡啶基    123-31183    -           COOMe      H       5-MeS-3-吡啶基        122-3184    -           COOMe      H       5-MeOCO-2-吡啶基      187-8185    -           COOMe      H       2，6-(MeO)2-         141-3
                                   3-吡啶基186    -           COOMe      H       5-MeSO2-3-吡啶基     168-70187    -           COOMe      H       5-MeSO-3-吡定基       130-2188    -           COOMe      Me      5-MeS-3-吡啶基        油状物189    -           COOMe      H       5-(N≡C-CH2O)-       固体
                                   3-吡啶基190    -           COOMe      Me      5-MeSO2-3-吡啶基     109-11191    -           COOMe      H       5-ClCH2S-3-吡啶基    112-4192    -           COOH       H       6-Cl-3-吡啶基         240193    -           COOMe      H       5-MeOCO-3-吡啶基      147-8194    -           COOMe      H       6-[N-(2-MeOCO-Ph)-    195-9
                                   NHCO]-3-吡啶基195    -           COOMe      H       5-Me-3-吡啶基         116-7196    -           COOMe      H       6-MeO-5-NO2-         150-1
                                   3-吡啶基197    -           COOMe      H       6-PhO-3-吡啶基        97-8198    -           COOMe      H       5，6-(MeS)2-         157-8
                                   3-吡啶基199    -           -CO-COOMe  H       6-MeO-3-吡啶基        133-6200    -           COOMe      Me      2，6-(MeO)2-          103-5
                                   3-吡啶基201    -           COOMe      Me      5-MeOCO-3-吡啶基      油状物202    -           COOMe      Me      5-Me-3-吡啶基         114-5203    -           COOH       H       5-HOCO-3-吡啶基       275化合物 (R1)n      Z        Y              A                   m.p.(°)204    -           COOMe     H          5-乙酰基-6-Me-            144-5
                                     3-吡啶基205    -           COOMe     H          5-Ph-3-吡啶基             124-5206    -           COOMe     Me         6-PhO-3-吡啶基            114-5207    -           COOMe     H          5-(N-(2-MeOCO-Ph)-        180-2
                                     NHCO]-3-吡啶基硫代208    -           COOMe     H          5-PhCH2S-3-吡啶基        104-6209    -           COOMe     Me         5-MeO-2-吡嗪基            81-3210   4-F          COOMe     Me         6-MeO-3-吡啶基            102-4211    -           COOMe     Et         6-MeO-3-吡啶基            53-5212    -           COOMe     H          2-MeO-5-嘧啶基            164-5213    -           COOMe     Me         2-MeO-5-嘧啶基            128-30214    -           COOMe     H          4，6-(MeO)2-2-PhCH2O-  127-9
                                     5-嘧啶基215    -           COOMe     H          2-Cl-4CF3-               139-40
                                     5-嘧啶基216    -           COOMe     H          2-Me2N-4CF3-            133-6
                                     5-嘧啶基217    -           COOMe     H          2-MeO-4CF3-              13940
                                     5-嘧啶基218    -           COOMe     H          6-Cl-5-MeO-               168-71
                                     2-吡嗪基219    -           COOMe     H          5-Br-2-Me-                165-6
                                     4-嘧啶基220    -           COOMe     H          2，4，6-(MeO)3-          153-5
                                     5-嘧啶基221    -           COOMe     Me         6-Cl-3-吡啶基             84-6222    -           COOMe     H          2-Cl-4-嘧啶基             159-61223    -           COOMe     H          5-Me-2-吡嗪基             158-60.5224    -           COOMe     H          2-MeO-4-嘧啶基            135-6225    -           COOPr     H          2-MeSO2-                 129-31
                                     5-嘧啶基化合物 (R1)n         Z       Y             A               m.p.(°)226    -            COOPr      H        2-MeSO-              116-8
                                     5-嘧啶基227    -            COOPr      H        2-MeO-5-嘧啶基       104-5228    -            COOEt      H        2-EtO-5-嘧啶基       134-5229    -            COOH       H        2-EtO-5-嘧啶基       150-62230    -            COOMe      H        2-Me-5-p嘧啶基       141-3231    -            COOMe      H        5-嘧啶基             158-61232    -            COOMe      Me       2-Me-5-嘧啶基        88-90233    -            COOMe      H        2-Cl-5-嘧啶基        159-61234    -            COOMe      H        2-Br-5-嘧啶基        177-8235    -            COOMe      H        2-PhCH2NH-          192-4
                                     5-嘧啶基236    -            COOMe      H        2-吗啉代基           222-3
                                     5-嘧啶基237    -            COOMe      H        5-Br-2-MeS-          192-4
                                     4-嘧啶基238    -            COOMe      H        5-Br-2-MeO-          178-80
                                     4-嘧啶基239    -            COOMe      H        2-MeOCOCH2NH-       194-7
                                     5-嘧啶基240    -            COOMe      H        2，6-Cl2-           170-5
                                     4-嘧啶基241    -            COOMe      H        2-CF3-5-嘧啶基      143-5242    -            COOMe      H        2-Ph-5-嘧啶基        151-5243    -            COOMe      H        2，6-(MeO)2-        167-9
                                     4-嘧啶基244    -            COOMe      Me       2-Ph-5-嘧啶基        胶状物245    -            COOMe      H        2，6-Cl2-           135-7
                                     5-嘧啶基Linyl246    -            COOMe      H        2-NC-5-嘧啶基        186-8247    -            COOMe      H        4，5-(MeO)2-        182-3
                                     2-嘧啶基化合物 (R1)n     Z        Y               A             m.p.(°)248    -          COOMe     H         4，6-(MeO)2-        163-4
                                   2-嘧啶基249    -          COOMe     H         2-MeONH-            194-6
                                   5-嘧啶基250    -          COOMe     H         2-MeNH-             230-1
                                   5-嘧啶基251    -          COOMe     H         2-Cl-4-(2-MeOCO-    190-2
                                   PhNH)-5-嘧啶基252    -          COOMe     H         5-Cl-6-Me-          136-41
                                   2-吡嗪基253    -          COOMe     H         5-MeO-6-Me-         166-9
                                   2-吡嗪基254    -          COOMe     H         2-(N-甲氧基         151-2
                                   N-甲氧基羰基氨基
                                   -5-嘧啶基255    -          COOMe     H         2-丙基              112-4
                                   5-嘧啶基256   3-MeOCO     COOMe     H         6-MeO-3-吡啶基      111-4257    -          COOMe     H         2-MeS-5-嘧啶基      160-2258    -          COOMe     H         5，6-Cl2-2-吡嗪基  143-8259    -          COOMe     H         5-(2-噻吩基-        148-9
                                   3-吡啶基260    -          COOMe     H         5-(4-CF3-Ph)-      155-6
                                   3-吡啶基261    -          COOMe     H         5-(ClSO2)-3-吡啶基 144-5262    -          COOMe     H         5-(Cl2CHS)-        120-2
                                   3-吡啶基263    -          COOMe     H         5-(NH2SO2)-       185-7
                                   3-吡啶基264    -          COOMe     H         5-Br-6-Cl-3-吡啶基  157-9265    -          COOMe     Me        5-NO2-6-MeO-       98-100
                                   3-吡啶基化合物 (R1)n      Z        Y              A             m.p.(°)266    -           COOMe     H         2-(1-咪唑基)-      193-5
                                    5-嘧啶基267    -           COOMe     H         4-MeO-2-MeS-       140-2
                                    5-嘧啶基268    -           COOMe     Me        2，6-(MeO)2-      101-3
                                    4-嘧啶基269    -           COOH   3，4-(MeO)2-6-MeO-3-吡啶基     123-4
                          苄基270    -           COOMe     H         5-(Me2NSO2)-     169-70
                                    3-吡啶基271    -           COOMe     H         5-Br-6-MeO-        169-70
                                    3-吡啶基272    -           COOMe     H         5-Br-6-MeSO2-     223-5
                                    3-吡啶基273    -           COOMe     H         5-Br-6-MeSO-       160-2
                                    3-吡啶基274    -           COOC5H11H         2-MeO-3-吡啶基     47-8275    -           COO-烯丙基H         2-MeO-3-吡啶基     80-1276    -           COOMe     2-Me-     6-(2-Me-苄基)-     油状物
                          苄基      3-吡啶基277    -           COOMe     H         2-Cl-4-喹啉基      163-4278    -           COOMe     -CH2Ph   6-MeO-3-吡啶基     101-2279 4，5-MeO2     COOMe     H         2-MeO-3-吡啶基     152-4280    -           COOMe     H         5-NH2-6-MeO-      202-3
                                    3-吡啶基281    -           COOMe     Me        2，4-(MeO)2-      78-81
                                    5-嘧啶基282    -           COOMe     2-MeO-    2-MeO-5-嘧啶基     胶状物
                          苄基283    -           COOMe     H         4-Me-2-MeS-        78-81
                                    5-嘧啶基化合物 (R1)n      Z        Y              A               m.p.(°)284    -           COOMe     H          2-(3-吡啶氧基)-     124-6
                                     5-嘧啶基285    -           COOMe     H          2-F-3-吡啶基        130-1286    -           COOMe     2-Me-      5，6-(MeO)2-       油状物
                          苄基       3-吡啶基287    -           COOMe     H          5，6-亚甲基二氧基   168-79
                                     3-吡啶基288    -           COOMe     H          5-I-6-MeO-吡啶基    173-5289 3，4-Me2      COOMe     H          2-MeO-3-吡啶基      126-7290   4-Cl         COOMe     H          2-MeO-3-吡啶基      128-30
还制备了下列化合物
a)N-(6-甲氧基-3-吡啶硫代羰基)邻氨基苯甲酸乙酯，为油状物(化合物291)
b)N-(5，6-二甲氧基-3-吡啶硫代羰基)邻氨基苯甲酸甲酯，m.p.154-5°，(化合物292)
c)N-(2-甲氧基-5-嘧啶硫代羰基)邻氨基苯甲酸甲酯，m.p.135-7°，(化合物293)，和
d)N-(6-甲氧基-3-吡啶硫代羰基)-邻氨基苯甲酸异丁酯，(化合物294)。
试验实施例
将化合物对一种或多种下列病菌的活性作了评价：
Phytophthora infestans：    蕃茄晚疫病
plasmopara viticola：       葡萄霜霉病
Erysiphe graminis：         大麦白粉病
Pyricularia oryzae：        稻瘟病
Pellicularia sasakii：      稻纹枯病
Botrytis cinerea：          灰霉病
Venturia inaequalis：       苹果黑星病
Leptosphaeria nodorum：     颖枯病
包括润湿剂的化合物水溶液或分散液以所需浓度通过喷雾或(如果适宜)浸泡试验植物的茎基施用。然后用适宜的试验病原菌接种植物或植物部分，并放置在适于维持植物生长和病害发展的控制环境条件下。一段适宜的时间后，用肉眼观察，估计植物感病部分的感染程度。如果化合物在500ppm(w/v)或更低的浓度下给出大于50％的病害防治效果，则认为化合物是有活性的。
化合物30，36，43，47，58，112，115，180，242和286显示出对Phytophthora infestans有活性；
化合物9，30，36，40，42，57，58，59，62，64，67-70，76，77，82，83，96，112，115，127，129，130，132，138，139，161，163，166，181，186，200-204，210，213，234，248，249，261，267，266，268，271和277显示出对Plasmopara viticola有活性；
化合物1-3，9-12，20，23，25，27-29，32，33，34，38，39，41，46，50，52，62，66，70，73，83，84，90，91，104-108，110，113，115，121-123，132，135，145，154，155，163，176，177，196，200，208，209，210-2，213，218，228，239，243，249，250，252-4，258，265，268，271-3，275，276，278和286显示出对Erysiphegraminis有活性；
化合物1，1a，2，6a，48，49，54-56，65，68，72，74，75，126，129，145，146，169，171，197，230，232，249，和277显示出对Pyricularia oryzae有活性；
化合物14，44，49，62，114，115，152，211，215，216和278显示出对Pellicularia sasakii有活性；
化合物48，51，52，53，61，63，121，129，195，228，和251显示出对Botrytis cinerea有活性；
化合物1，8，12，17，45，63，86，104，112，119，146，149，150，151，187，189，204，211，219，224，239，244，245，248和250显示出对Venturia inaequalis有活性；和
化合物24，35，60，61，71，204，216，220和249显示出对Leptosphaeria nodorum有活性。

Claims (3)

1.一种式I化合物
Figure A9519213100021
X是O或S；A是含有至少一个氮原子的6元杂芳基，它任由一个或多个R2基团取
代；R1是烷基、环烷基、环烯基、链烯基、炔基、或氨基，(各基团任选被
取代)，Y′-X-、卤素、氰基、硝基、酰基、酰氧基、任选取
代的杂环基或任选取代的苯基；或两个相邻基团和与之相连的碳原
子一起可以形成任选取代的苯并环；R2具有与R1相同的含意或两个相邻基团和与之相连的碳原子一起可以
形成任选取代的杂环；Y是烷基、环烷基、环烯基、链烯基或炔基，各基团任选被取代，氢或
酰基；Y1具有与Y相同的含意或是任选取代的苯基或任选取代的杂环基；Z是C(＝X1)-X2-R3、氰基、硝基、氨基、酰基、任选取代的
杂环基、-C(R5)＝N-OR6或-C(R5)＝N-NR6R7；R3是烷基、环烷基、环烯基、链烯基、炔基、苯基或杂环基，各基团任
选被取代，氢或无机或有机阳离子基团；X1和X2，它们可以相同或不同，为O或S；R5、R6和R7，它们可以相同或不同，是烷基、环烷基、环烯基、链烯
基、炔基、苯基或杂环基，各基团任选被取代，或是氢或R6和R7
和与之相连的原子一起可以形成环；且n是0至4，与金属盐的配合物，以及当化合物是酸时与碱形成的盐和当化合物是碱
时与酸形成的盐，其条件是当Y是氢且：i)是Z是羧基、甲氧羰基或乙氧羰基时，环A不是未取代的吡啶基或吡嗪基；和ii)当Z是羧基和n是0时，A不是2-氯-3-吡啶基、6-(2-二乙基氨基乙氧基)-3-吡啶基或2-吡啶基。
2.杀真菌组合物，包含与农业上可接受的稀释剂或载体混合的按照权利要求1中所要求的化合物。
3.一种在滋生或易于滋生真菌病害的地点防治植物致病真菌的方法，其中包含向此地点施用按照权利要求1中所要求的化合物。
CN95192131A 1994-03-18 1995-03-16 杀真菌化合物 Pending CN1143954A (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9405347A GB9405347D0 (en) 1994-03-18 1994-03-18 Fungicides
GB9405347.7 1994-03-18

Publications (1)

Publication Number Publication Date
CN1143954A true CN1143954A (zh) 1997-02-26

Family

ID=10752091

Family Applications (1)

Application Number Title Priority Date Filing Date
CN95192131A Pending CN1143954A (zh) 1994-03-18 1995-03-16 杀真菌化合物

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)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107531622A (zh) * 2015-05-13 2018-01-02 日本农药株式会社 邻氨基苯甲酸酯化合物或其盐类和含有该化合物的农业园艺用杀菌剂及其使用方法
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
CN114246189A (zh) * 2020-09-21 2022-03-29 青岛好利特生物农药有限公司 一种吡嗪酰胺类杀菌剂及其制备方法

Families Citing this family (68)

* 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
CA2230894A1 (en) * 1995-09-01 1997-03-13 Signal Pharmaceuticals, Inc. Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions
US5811428A (en) * 1995-12-18 1998-09-22 Signal Pharmaceuticals, Inc. Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions
GB9518994D0 (en) * 1995-09-16 1995-11-15 Agrevo Uk Ltd Fungicides
GB9518993D0 (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
EP1134214A4 (en) 1998-11-04 2004-12-15 Meiji Seika Kaisha PICOLINAMIDE DERIVATIVES AND PESTICIDES CONTAINING THESE DERIVATIVES AS ACTIVE INGREDIENT
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.
EP1257536A1 (en) * 2000-01-27 2002-11-20 Cytovia, Inc. Substituted nicotinamides and analogs as activators of caspases and inducers of apoptosis and the use thereof
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
WO2003050088A1 (en) * 2001-12-07 2003-06-19 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
CA2508171C (en) * 2002-12-13 2012-08-28 Cytopia Pty Ltd Nicotinamide-based kinase inhibitors
AU2003291839B2 (en) * 2002-12-13 2009-01-22 Ym Biosciences Australia Pty Ltd Nicotinamide-based kinase inhibitors
US8030336B2 (en) * 2002-12-13 2011-10-04 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
EP1863757A4 (en) * 2005-03-14 2012-02-22 Evotec Ag AMIDE DERIVATIVES AS IONIC CHANNEL LIGANDS AND PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF
RU2404164C2 (ru) * 2005-04-06 2010-11-20 Ф.Хоффманн-Ля Рош Аг Производные пиридин-3-карбоксамида в качестве обратных агонистов св1
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
DK1937664T3 (da) 2005-10-14 2011-07-18 Sumitomo Chemical Co Hydrazidforbindelse og pesticid anvendelse af den samme
DE602006021591D1 (de) * 2006-12-11 2011-06-09 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
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
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
EP3725775A1 (en) 2009-02-17 2020-10-21 Syntrix Biosystems, Inc. Pyridine- and pyrimidinecarboxamides 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
EP2560488B1 (en) 2010-04-23 2015-10-28 Cytokinetics, Inc. Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
AR081331A1 (es) 2010-04-23 2012-08-08 Cytokinetics Inc Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos
US8779149B2 (en) 2010-08-23 2014-07-15 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
CN104144913B (zh) 2011-12-21 2017-05-17 诺维拉治疗公司 B型肝炎抗病毒剂
TWI636036B (zh) * 2012-08-28 2018-09-21 健生科學愛爾蘭無限公司 胺磺醯基－芳基醯胺類及其作為用於治療ｂ型肝炎的藥物之用途
US10125094B2 (en) 2013-02-28 2018-11-13 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
PL2981536T3 (pl) 2013-04-03 2017-11-30 Janssen Sciences Ireland Uc Pochodne N-fenylo-karboksyamidu i ich zastosowanie jako leku do leczenia wirusowego zapalenia wątroby typu B
PT2997019T (pt) 2013-05-17 2018-11-21 Janssen Sciences Ireland Uc Derivados de sulfamoíltiofenamida e o seu uso 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
NO3024819T3 (zh) 2013-07-25 2018-07-21
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
JP6452119B2 (ja) 2013-10-23 2019-01-16 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 カルボキサミド誘導体およびｂ型肝炎の処置のための医薬品としてのその使用
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
CN106232136A (zh) 2014-02-05 2016-12-14 诺维拉治疗公司 用于治疗hbv感染的联合疗法
UY35980A (es) 2014-02-06 2015-08-31 Janssen Sciences Ireland Uc Derivados de sulfamoilpirrolamida como inhibidores del hbv y composiciones farmacéuticas que los contienen
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
MX2018012557A (es) 2016-04-15 2019-07-04 Janssen Sciences Ireland Uc Combinaciones y métodos que comprenden un inhibidor del ensamblaje de la cápside.
MX2020009531A (es) 2018-03-14 2020-10-05 Janssen Sciences Ireland Unlimited Co Regimen posologico del modulador del ensamblaje de la capside.
WO2020169784A1 (en) 2019-02-22 2020-08-27 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of hbv infection or hbv-induced diseases
US11491148B2 (en) 2019-05-06 2022-11-08 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

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107531622A (zh) * 2015-05-13 2018-01-02 日本农药株式会社 邻氨基苯甲酸酯化合物或其盐类和含有该化合物的农业园艺用杀菌剂及其使用方法
CN107531622B (zh) * 2015-05-13 2020-03-20 日本农药株式会社 邻氨基苯甲酸酯化合物或其盐类和含有该化合物的农业园艺用杀菌剂及其使用方法
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
CN114246189A (zh) * 2020-09-21 2022-03-29 青岛好利特生物农药有限公司 一种吡嗪酰胺类杀菌剂及其制备方法

Also Published As

Publication number Publication date
DE69503365T2 (de) 1999-01-07
BR9507105A (pt) 1997-09-09
US5756524A (en) 1998-05-26
CZ269096A3 (en) 1996-12-11
EP0750611A1 (en) 1997-01-02
IL113027A0 (en) 1995-06-29
ZA952205B (en) 1995-10-31
EP0750611B1 (en) 1998-07-08
WO1995025723A1 (en) 1995-09-28
AU688473B2 (en) 1998-03-12
TW318829B (zh) 1997-11-01
DE69503365D1 (de) 1998-08-13
HU214292B (hu) 1998-03-02
MX9603735A (es) 1997-12-31
HUT74778A (en) 1997-02-28
HU9602547D0 (en) 1996-11-28
JPH09510471A (ja) 1997-10-21
AU1898195A (en) 1995-10-09
PL316289A1 (en) 1997-01-06
GB9405347D0 (en) 1994-05-04
ATE168099T1 (de) 1998-07-15

Similar Documents

Publication Publication Date Title
CN1143954A (zh) 杀真菌化合物
CN1044233C (zh) 酰胺化合物及其盐，它们的制造工艺及其农药组合物
CN1026981C (zh) 胍衍生物的制备方法
CN1132816C (zh) 2－吡啶基甲胺衍生物及其应用和杀虫剂组合物
CN1038678C (zh) 杀真菌组合物,其制备方法及应用
CN1023600C (zh) 杀菌剂组合物及其制法
CN1020901C (zh) 杀真菌剂组合物其制备方法及用途
CN1318055A (zh) 用作除草剂的吡啶酮
CN1050714A (zh) 胺衍生物
CN1370047A (zh) 杀真菌剂
CN1543460A (zh) 用于防治无脊椎害虫的邻-杂环取代的芳基酰胺类化合物
CN1342137A (zh) N2－苯基脒衍生物
CN1370046A (zh) 杀真菌剂
CN1298706C (zh) 杀虫二酰胺类
CN1568144A (zh) 用于防治无脊椎害虫的亚氨基苯并噁嗪、亚氨基苯并噻嗪和亚氨基喹唑啉
CN1231663A (zh) 杀节肢动物剂和杀真菌剂环酰胺
CN1121399C (zh) 异噻唑羧酸衍生物
CN1147247A (zh) 用作杀微生物剂的n-磺酰和n-亚磺酰氨基酸酰胺
EA036913B1 (ru) Сельскохозяйственные фунгицидные химические вещества
CN1065659A (zh) N-苯基氨基甲酸酯化合物、其制备方法以及控制有害生物的杀虫剂组合物
CN1443174A (zh) 杀真菌的5－苯基取代的2－(氰氨基)嘧啶化合物
CN1620449A (zh) 二酰胺化合物无脊椎害虫防治剂
CN1045439C (zh) 杂芳酰基异噁唑衍生物、其制备应用及含该衍生物的组合物
CN1102828A (zh) 四氢化嘧啶的制备方法
CN1032184C (zh) 杀真菌剂及其制备方法

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C01 Deemed withdrawal of patent application (patent law 1993)