CN1195734C - 邻苯二甲酰胺衍生物、其制备中的中间体和农业/园艺杀虫剂及其使用方法 - Google Patents

邻苯二甲酰胺衍生物、其制备中的中间体和农业/园艺杀虫剂及其使用方法 Download PDF

Info

Publication number
CN1195734C
CN1195734C CNB008100071A CN00810007A CN1195734C CN 1195734 C CN1195734 C CN 1195734C CN B008100071 A CNB008100071 A CN B008100071A CN 00810007 A CN00810007 A CN 00810007A CN 1195734 C CN1195734 C CN 1195734C
Authority
CN
China
Prior art keywords
halo
alkyl
wan
och
alkylthio
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.)
Expired - Fee Related
Application number
CNB008100071A
Other languages
English (en)
Other versions
CN1360573A (zh
Inventor
町谷幸三
远藤和义
古谷敬
中尾勇美
后藤诚
河野荣司
远西正范
坂田和之
森本雅之
濑尾明
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.)
Nihon Nohyaku Co Ltd
Original Assignee
Nihon Nohyaku Co 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 Nihon Nohyaku Co Ltd filed Critical Nihon Nohyaku Co Ltd
Publication of CN1360573A publication Critical patent/CN1360573A/zh
Application granted granted Critical
Publication of CN1195734C publication Critical patent/CN1195734C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • 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
    • A01N43/08—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 oxygen 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
    • A01N43/02—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
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-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
    • A01N43/34—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
    • A01N43/54—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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C07D231/40—Acylated on said nitrogen atom
    • 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
    • C07D233/66—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 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
    • C07D233/88—Nitrogen atoms, e.g. allantoin
    • 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
    • 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
    • C07D241/20—Nitrogen atoms
    • 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
    • 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
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/48—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/04—1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/50—Nitrogen atoms bound to hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/66—Nitrogen atoms
    • 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms

Abstract

由通式(I)代表的杂环胺衍生物，其中R1、R2和R3各自代表H、任选被卤化的C3-C6环烷基等；Q代表任选被取代的含O、S或N的杂环；X代表卤素、氰基、卤代C1-C6烷基等；n是1至4；Z1和Z4各自代表O或S；及其由下列通式(IV’)代表的中间体：Q’-NH2，其中Q’代表一定的杂环，选自由Q代表的那些。农业/园艺杀虫剂，具有显著的防治农作物害虫的作用，例如稻、果树和蔬菜以及各种农业、林业、园艺和储存谷物害虫。

Description

邻苯二甲酰胺衍生物、其制备中的中间体 和农业/园艺杀虫剂及其使用方法
发明背景
发明领域
本发明涉及邻苯二甲酰胺衍生物、其中间体的制备、含有所述化合物作为活性成分的农艺杀虫剂和使用所述杀虫剂的方法。
相关技术
一部分本发明的邻苯二甲酰胺衍生物公开在JP-A-59-163353、JP-A-61-180753、《英国化学会志(J.C.S.)柏尔金汇刊I》1338-1350(1978)等中。不过，关于这些化合物作为农艺杀虫剂的有用性其中完全没有说明和提示。另一方面，由通式(IV)代表的杂环胺衍生物作为制备所述邻苯二甲酰胺衍生物的中间体化合物，是文献中没有记载的新化合物。
发明概述
本发明人为研制新颖的农艺药物而进行了反复研究。结果发现，由通式(I)代表的本发明的邻苯二甲酰胺衍生物是新颖的化合物，有些是现有技术公开的已知化合物，它们可用作新颖的农艺杀虫剂。进一步发现，由通式(IV’)代表的杂环胺衍生物是文献中没有记载的新化合物，它们可用作各种生理活性化合物制备的中间体，这些生理活性物质可用作药物、农药等。基于这些发现，完成了本发明。
发明的详细说明
本发明涉及由通式(I)代表的邻苯二甲酰胺衍生物：
{其中R1、R2和R3可以是相同或不同的，代表氢原子、C3-C6环烷基、卤代C3-C6环烷基或-A1-(G)r(该式中，A1代表C1-C8亚烷基、C3-C6亚烯基或C3-C6亚炔基；G可以是相同或不同的，代表氢原子，卤原子，氰基，硝基，卤代C1-C6烷基，C3-C6环烷基，卤代C3-C6环烷基，C1-C6烷氧基羰基，二(C1-C6)烷氧基磷酰基、其中(C1-C6)烷氧基可以是相同或不同的，二(C1-C6)烷氧基硫代磷酰基、其中(C1-C6)烷氧基可以是相同或不同的，二苯基膦基，二苯基膦酰基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(此处所用的术语“杂环基”表示吡啶基、吡啶-N-氧化物、嘧啶基、呋喃基、四氢呋喃基、噻吩基、四氢噻吩基、四氢吡喃基、噁唑基、异噁唑基、噁二唑基、噻唑基、异噻唑基、噻二唑基、咪唑基、***基或吡唑基)，取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，或-Z3-R4(该式中，Z3代表-O-、-S-、-SO-、-SO2-、-N(R5)-(该式中，R5代表氢原子，C1-C6烷基羰基，卤代C1-C6烷基羰基，C1-C6烷氧基羰基，苯基羰基，取代的苯基羰基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，苯基C1-C4烷氧基羰基，取代的苯基C1-C4烷氧基羰基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，C1-C6烷基磺酰基，或卤代C1-C6烷基磺酰基)、-C(＝O)-或-C(＝NOR6)-(该式中，R6代表氢原子，C1-C6烷基，卤代C1-C6烷基，C3-C6烯基，卤代C3-C6烯基，C3-C6炔基，C3-C6环烷基，苯基C1-C4烷基，或取代的苯基C1-C4烷基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组)，和R4代表氢原子，C1-C6烷基、卤代C1-C6烷基，C3-C6烯基，卤代C3-C6烯基，C3-C6炔基，卤代C3-C6炔基，C3-C6环烷基，卤代C3-C6环烷基，C1-C6烷氧基C1-C6烷基，C1-C6烷硫基C1-C6烷基，甲酰基，C1-C6烷基羰基，卤代C1-C6烷基羰基，C1-C6烷氧基羰基，一(C1-C6)烷基氨基羰基，二(C1-C6)烷基氨基羰基、其中(C1-C6)烷基可以是相同或不同的，一(C1-C6)烷基氨基硫代羰基，二(C1-C6)烷基氨基硫代羰基、其中(C1-C6)烷基可以是相同或不同的，二(C1-C6)烷氧基磷酰基、其中(C1-C6)烷氧基可以是相同或不同的，二(C1-C6)烷氧基硫代磷酰基、其中(C1-C6)烷氧基可以是相同或不同的，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，苯基C1-C4烷基，取代的苯基C1-C4烷基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，或取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组)；r代表1至4的整数)；进一步，R1和R2可以结合一起形成可以被1至3个相同或不同的氧原子、硫原子或氮原子间断的4-至7-元环；
X可以是相同或不同的，代表卤原子，氰基，硝基，C3-C6环烷基，卤代C3-C6环烷基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，或-A2-R7[该式中，A2代表-O-、-S-、-SO-、-SO2-、-NR8-(该式中，R8代表氢原子，C1-C6烷基羰基，卤代C1-C6烷基羰基，C1-C6烷氧基羰基，苯基羰基，取代的苯基羰基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，苯基C1-C4烷氧基羰基，或取代的苯基C1-C4烷氧基羰基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组)、-C(＝O)-、-C(＝NOR6)-(该式中，R6定义同上)、C1-C6亚烷基、卤代C1-C6亚烷基、C2-C6亚烯基、卤代C2-C6亚烯基、C2-C6亚炔基或卤代C3-C6亚炔基；和
(1)在A2代表-O-、-S-、-SO-、-SO2-或-NR8-(该式中，R8定义同上)的情况下，R7代表氢原子，卤代C3-C6环烷基，卤代C3-C6环烯基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，或-A3-R9(该式中，A3代表C1-C6亚烷基、卤代C1-C6亚烷基、C3-C6亚烯基、卤代C3-C6亚烯基、C3-C6亚炔基或卤代C3-C6亚炔基；R9代表氢原子，卤原子，C3-C6环烷基，卤代C3-C6环烷基，C1-C6烷氧基羰基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，或-A4-R10(该式中，A4代表-O-、-S-、-SO-、-SO2-或-C(＝O)-；R10代表C1-C6烷基，卤代C1-C6烷基，C3-C6烯基，卤代C3-C6烯基，C3-C6环烷基，卤代C3-C6环烷基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，或取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组))；
(2)在A2代表-C(＝O)-或-C(＝NOR6)-(该式中，R6定义同上)的情况下，R7代表氢原子，C1-C6烷基，卤代C1-C6烷基，C2-C6烯基，卤代C2-C6烯基，C3-C6环烷基，卤代C3-C6环烷基，C1-C6烷氧基，C1-C6烷硫基，一(C1-C6)烷基氨基，二(C1-C6)烷基氨基、其中(C1-C6)烷基可以是相同或不同的，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，苯基氨基，取代的苯基氨基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，或取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组；和
(3)在A2代表C1-C6亚烷基、卤代C1-C6亚烷基、C2-C6亚烯基、卤代C2-C6亚烯基、C2-C6亚炔基或卤代C3-C6亚炔基的情况下，R7代表氢原子，卤原子，C3-C6环烷基，卤代C3-C6环烷基，C1-C6烷氧基羰基，三(C1-C6)烷基甲硅烷基、其中(C1-C6)烷基可以是相同或不同的，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，或-A5-R11(该式中，A5代表-O-、-S-、-SO-、或-SO2-；R11代表C3-C6环烷基，卤代C3-C6环烷基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，或-A6-R12(该式中，A6代表C1-C6亚烷基、卤代C1-C6亚烷基、C2-C6亚烯基、卤代C2-C6亚烯基、C2-C6亚炔基或卤代C3-C6亚炔基；R12代表氢原子，卤原子，C3-C6环烷基，卤代C3-C6环烷基，C1-C6烷氧基，卤代C1-C6烷氧基，C1-C6烷硫基，卤代C1-C6烷硫基，C1-C6烷基亚磺酰基，卤代C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，卤代C1-C6烷基磺酰基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，苯氧基，取代的苯氧基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，苯硫基，取代的苯硫基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，或取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组))]；
n代表0至4的整数；进一步，X可以与苯环上相邻的碳原子结合一起形成稠合的环(此处所用的术语稠合的环表示萘、四氢化萘、茚、二氢化茚、喹啉、喹唑啉、苯并二氢吡喃、异苯并二氢吡喃、吲哚、二氢吲哚、苯并二噁烷、苯并间二氧杂环戊烯、苯并呋喃、二氢苯并呋喃、苯并噻吩、二氢苯并噻吩、苯并噁唑、苯并噻唑、苯并咪唑或吲唑)，所述稠合的环可以具有至少一个相同或不同的取代基，选自卤原子，C1-C6烷基，卤代C1-C6烷基，C1-C6烷氧基，卤代C1-C6烷氧基，C1-C6烷硫基，卤代C1-C6烷硫基，C1-C6烷基亚磺酰基，卤代C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，卤代C1-C6烷基磺酰基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，和取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组；
Q代表含N-、S-或O-的、任选被取代的杂环基或稠合的杂环基，选自由下式Q1至Q60组成的组：
(这些式中，Y可以是相同或不同的，代表卤原子，氰基，硝基，卤代C3-C6环烷基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，或-A2-R7(该式中，A2和R7定义同上)；m代表0至6的整数；式Q22和Q23中的R13代表氢原子，C1-C6烷基，卤代C1-C6烷基，C3-C6烯基，卤代C3-C6烯基，C3-C6炔基，卤代C3-C6炔基，C3-C6环烷基，卤代C3-C6环烷基，C1-C6烷氧基C1-C6烷基，卤代C1-C6烷氧基C1-C6烷基，C1-C6烷硫基C1-C6烷基，卤代C1-C6烷硫基C1-C6烷基，C1-C6烷基亚磺酰基C1-C6烷基，卤代C1-C6烷基亚磺酰基C1-C6烷基，C1-C6烷基磺酰基C1-C6烷基，卤代C1-C6烷基磺酰基C1-C6烷基，C1-C6烷基磺酰基，卤代C1-C6烷基磺酰基，C1-C6烷基羰基，卤代C1-C6烷基羰基，C1-C6烷氧基羰基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，苯基C1-C4烷基，取代的苯基C1-C4烷基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，苯基羰基，或取代的苯基羰基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组)；
或者，Y可以与环上相邻的碳原子结合一起形成稠合的环(稠合的环定义同上)，所述稠合的环可以具有至少一个相同或不同的取代基，选自卤原子，C1-C6烷基，卤代C1-C6烷基，C1-C6烷氧基，卤代C1-C6烷氧基，C1-C6烷硫基，卤代C1-C6烷硫基，C1-C6烷基亚磺酰基，卤代C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，卤代C1-C6烷基磺酰基，苯基，取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组，杂环基(术语杂环基定义同上)，和取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组；
W代表O、S或N-R13(该式中，R13定义同上)；Z1和Z2代表氧原子或硫原子；
其条件是若X、R1和R3同时代表氢原子，Z1和Z2同时代表氧原子，Q代表Q27，Y是2-位的氯原子，则R2不是1，2，2-三甲基丙基}；
还涉及农艺杀虫剂及其使用方法。
本发明进一步涉及由下列通式(IV’)代表的杂环胺衍生物：
              Q’-NH2               (IV’)
其中：
(1)在Q’代表下式Q26、Q28-Q31和Q33-Q39的情况下，
Figure C0081000700191
Y可以是相同或不同的，代表氢原子、卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或卤代C1-C6烷基磺酰基，m代表1至4的整数，总数为m的Y至少有一个是全氟C2-C6烷基；
(2)在Q’代表Q27和Q32的情况下，
Y可以是相同或不同的，代表氢原子、卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或卤代C1-C6烷基磺酰基，m代表1至4的整数，总数为m的Y至少有一个是全氟C2-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷氧基卤代C1-C6烷氧基或卤代C1-C6烷硫基。
式(IV’)的杂环胺衍生物可用作制备式(I)的邻苯二甲酰胺衍生物的中间体化合物。
在本发明邻苯二甲酰胺衍生物通式(I)的定义中，“卤原子”表示氯原子、溴原子、碘原子或氟原子；“C1-C6烷基”表示具有1至6个碳原子的直链或支链烷基，例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、正己基等；“卤代C1-C6烷基”表示被至少一个相同或不同的卤原子取代的、具有1至6个碳原子的直链或支链烷基；“C1-C8亚烷基”表示具有1至8个碳原子的直链或支链亚烷基，例如亚甲基、亚乙基、1，2-亚丙基、1，3-亚丙基、二甲基亚甲基、亚丁基、异亚丁基、二甲基亚乙基、亚辛基等。
关于“R1和R2结合一起形成可以被1至3个相同或不同的氧原子、硫原子或氮原子间断的4-至7-元环”的实例，可以提及氮杂环丁烷环、吡咯烷环、吡咯啉环、哌啶环、咪唑烷环、咪唑啉环、噁唑烷环、噻唑烷环、异噁唑烷环、异噻唑烷环、四氢吡啶环、哌嗪环、吗啉环、硫代吗啉环、二噁嗪环、二噻嗪环等。
有些由通式(I)代表的本发明的邻苯二甲酰胺衍生物在其结构式中具有不对称碳原子或不对称中心，有时可以存在两种旋光异构体。本发明包括所有这样的旋光异构体和它们的任意比例混合物，有时包括它们的盐和水合物。
在由通式(I)代表的本发明的邻苯二甲酰胺衍生物中，优选的取代基如下。因而，本发明的邻苯二甲酰胺衍生物优选为这样的通式(I)的邻苯二甲酰胺衍生物，其中R1、R2和R3可以是相同或不同的，代表氢原子或-A1-G(该式中，A1代表C1-C8亚烷基，G代表氢原子、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基氨基或C1-C6烷氧基羰基氨基)；X可以是相同或不同的，代表卤原子、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基或卤代C1-C6烷硫基；n代表0至4的整数；Q代表Q27；Y可以是相同或不同的，代表卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、卤代C1-C6烷氧基卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷氧基卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基或卤代C1-C6烷基磺酰基；m代表0至4的整数；Z1和Z2代表氧原子。进一步优选地，本发明的邻苯二甲酰胺衍生物是这样的通式(I)的邻苯二甲酰胺衍生物，其中R1和R3代表氢原子；R2代表C1-C6烷硫基C1-C6烷基；X代表卤原子；n代表1至2的整数；Q代表Q27；Y可以是相同或不同的，代表卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基；m代表1至2的整数；Z1和Z2代表氧原子。
本发明化合物可以按照下述流程1和2加以制备，不过本发明化合物也可以通过JP-A-11-240857所述方法加以制备。
制备方法1
其中R1、R2、Z1、Z2、X、Q和n定义同上。
在惰性溶剂的存在下，由通式(V)代表的邻苯二甲酸酐衍生物与由通式(IV)代表的杂环胺衍生物反应，生成由通式(III)代表的邻苯二甲酰亚胺衍生物。分离或者不分离邻苯二甲酰亚胺衍生物(III)后，(III)与由通式(II)代表的胺反应。因而，可以制备由通式(I-1)代表的邻苯二甲酰亚胺衍生物。
(1)通式(V)→通式(III)
关于用在该反应中的惰性溶剂，可以使用任意溶剂，只要它不明显妨碍反应进行即可。可以使用的惰性溶剂实例包括芳族烃，例如苯、甲苯、二甲苯等，卤代烃，例如二氯甲烷、氯仿、四氯化碳等，氯代芳族烃，例如氯苯、二氯苯等，无环族与环族醚，例如***、二噁烷、四氢呋喃等，酯，例如乙酸乙酯等，酰胺，例如二甲基甲酰胺、二甲基乙酰胺等，酸，例如乙酸等，二甲基亚砜，1，3-二甲基-2-咪唑烷酮等。这些惰性溶剂既可以单独使用，也可以两种或多种溶剂结合使用。
由于该反应是等摩尔反应，可以使用等摩尔量的反应物。不过如果需要的话，也可以使用过量的任意一种反应物。根据需要，该反应可以在脱水条件下进行。
反应可以在室温至所用惰性溶剂的回流温度之间的温度下进行。尽管反应时间可以因反应的规模和温度而异，不过可以在若干分钟至48小时的范围内加以适当选择。
反应完全后，按常规方式从反应***中分离目标产物，根据需要通过重结晶、柱色谱等方法纯化，由此可以得到目标产物。不经分离而将目标产物送入随后的步骤也是可能的。
由通式(V)代表的邻苯二甲酸酐衍生物可以按照《有机化学杂志》 52，129(1987)、《美国化学会志》 51，1865(1929)、出处同上 63，1542(1941)等所述方法加以制备。由通式(IV)代表的杂环胺衍生物可以按照《有机化学杂志》 18，138(1953)、《有机化学杂志》28，1877(1963)、《化学报告》 89，2742(1956)、《印度科学院院报》 37A，758(1953)、《杂环化学杂志》 17，143(1980)、JP-A-62-96479、JP-A-10-340345、JP-A-11-302233等所述方法加以制备。
(2)通式(III)→通式(I-1)
关于可用在该反应中的惰性溶剂，可以与可用在上述反应(1)中的那些相同。由于该反应是等摩尔反应，可以使用等摩尔量的反应物，不过如果需要的话，也可以使用过量的通式(II)的胺。反应可以在室温至所用惰性溶剂的回流温度之间的温度下进行。尽管反应时间可以因反应的规模和温度而异，不过可以在若干分钟至48小时的范围内加以适当选择。
反应完全后，按常规方式从含有产物的反应***中分离目标产物。根据需要通过重结晶、柱色谱等方法纯化产物，由此可以得到目标产物。
制备方法2
其中R1、R2、R3、X、Q和n定义同上。
在惰性溶剂的存在下，由通式(V)代表的邻苯二甲酸酐衍生物与由通式(II)代表的胺反应，生成由通式(III-2)代表的邻苯二甲酰胺。在(III-2)中的R1是氢原子的情况下，分离或者不分离邻苯二甲酰胺(III-2)，然后在缩合剂的存在下进行缩合反应，生成由通式(VI-1)代表的化合物，分离或者不分离(VI-1)后，在惰性溶剂的存在下，化合物(VI-1)与由通式(IV)代表的杂环胺衍生物反应。在邻苯二甲酰胺(III-2)中的R1不是氢原子的情况下，在缩合剂的存在下，已经分离或者末分离的(III-2)与由通式(IV)代表的杂环胺进行缩合反应。按这些方式，可以制备由通式(I-2)代表的邻苯二甲酰胺衍生物。
或者，在惰性溶剂的存在下，由通式(V)代表的邻苯二甲酸酐衍生物与由通式(IV)代表的杂环胺衍生物反应，生成由通式(III-1)代表的邻苯二甲酰胺。在(III-1)中的R3是氢原子的情况下，分离或者不分离邻苯二甲酰胺(III-1)，然后在缩合剂的存在下进行缩合反应，生成由通式(VI)代表的化合物，分离或者不分离(VI)后，在惰性溶剂的存在下，(VI)与由通式(II)代表的胺进行反应。在(III-1)中的R3不是氢原子的情况下，在缩合剂的存在下，已经分离或者未分离的(III-1)与由通式(II)代表的胺进行缩合反应。按这些方式，可以制备由通式(I-2)代表的邻苯二甲酰胺衍生物。
(1)通式(V)→(III-2)或通式(VI-1)→通式(I-2)
该反应可以按与制备方法1-(2)相同的方式进行，由此可以得到目标产物。
(2)通式(III-1)→(VI)或通式(III-2)→通式(VI-1)
该反应可以按照《药物化学杂志》 10，982(1967)的说明进行，由此可以得到目标产物。
(3)通式(VI)→(I-2)或通式(V)→通式(III-2)
该反应可以按与制备方法1-(2)相同的方式进行，由此可以得到目标产物。
(4)通式(III-1)或通式(III-2)→通式(I-2)
该反应可以这样进行，即，在缩合剂和惰性溶剂的存在下，由通式(III-1)或(III-2)代表的邻苯二甲酰胺衍生物与由通式(II)或(IV)代表的胺反应。如果必要的话，该反应可以在碱的存在下进行。
关于用在该反应中的惰性溶剂实例，可以提及四氢呋喃、***、二噁烷、氯仿、二氯甲烷等。关于用在该反应中的缩合剂，可以使用用在常规酰胺制备中的那些，其实例包括Mukaiyama试剂(2-氯-N-甲基吡啶输碘化物)、DCC(1，3-二环己基碳二亚胺)、CDI(羰基二咪唑)、DEPC(氰基膦酸二乙酯)等。基于由通式(III-1)或(III-2)代表的邻苯二甲酰胺衍生物而言，缩合剂的量可以在等摩尔量至过量摩尔量的范围内加以适当选择。
关于可以用在该反应中的碱实例，可以提及有机碱，例如三乙胺、吡啶等，和无机碱，例如碳酸钾等。基于由通式(III-1)或(III-2)代表的邻苯二甲酰胺衍生物而言，碱的量可以在等摩尔量至过量摩尔量的范围内加以适当选择。
反应可以在0℃至所用惰性溶剂的沸点之间的温度下进行。尽管反应时间可以因反应的规模和温度而异，不过在若干分钟至48小时的范围内。
反应完全后，通过常规方法从反应***中分离目标产物，根据需要可以通过重结晶、柱色谱等方法纯化产物，由此可以得到目标产物。
下面，由通式(IV’)代表的杂环胺衍生物的典型实例列在表1中，由通式(I)代表的邻苯二甲酰胺衍生物的典型实例列在表2至12中。本发明决不限于这里所示的化合物。下表中，“Me”表示甲基，“Et”表示乙基，“Pr”表示丙基，“Bu”表示丁基，“Ac”表示乙酰基，“Ph”表示苯基，“c-”表示脂环族烃，“mp”表示熔点，“nD”表示折光指数。
通式(IV’)
     Q′-NH2                            (IV′)
Figure C0081000700261
                                           表1
No.         Q′       Ym                    mp(℃)或1H-NMR[δ(ppm/CDCl3)]
IV′-1      Q26       3-Me-5-C2F5         2.17(s.3H)，4.82(br.2H)，7.42(d.
                                            1H)，8.16(s.1H).
IV′-2      Q26       3-Me-5-n-C3F7       2.18(s.3H)，4.94(br.2H)，7.41(d.
                                            1H)，8.19(s.1H).
IV′-3      Q26       3-Me-5-i-C3F7       2.18(s.3H)，4.80(br.2H)，7.42(d.
                                            1H)，8.15(s.1H).
                               表1(续)
No.           Q′    Ym                       mp(℃)或1H-NMR[δ(ppm/CDCl3)]
IV′-4        Q27    2-n-C3F7               4.08(br.2H)，7.04(dd.1H)，7.43(d.
                                              1H)，8.16(d.1H).
IV′-5        Q27    6-Cl-2-n-C3F7          4.65(br.2H)，7.17(d.1H)，7.57(d.
                                              1H).
IV′-6        Q27    2-C2F5                 3.72(br.2H)，7.04(dd.1H)，7.46(d.
                                              1H)，8.16(d.1H).
IV′-7        Q27    2-i-C3F7               4.12(br.2H)，7.06(dd.1H)，7.44(dd.
                                              1H)，8.13(d.1H).
IV′-8        Q27    4-Me-2-i-C3F7          2.22(s.3H)，4.12(br.2H)，7.34(d.
                                              1H)，8.07(s.1H).
IV′-9        Q27    4-Me-6-i-C3F7          2.21(s.3H)，4.26(br.2H)，7.09(dd.
                                              1H)，7.98(d.1H).
IV′-10       Q27    6-Me-2-i-C3F7          2.42(s.3H)，4.12(br.2H)，6.98(d.
                                              1H)，7.31(dd.1H).
IV′-11       Q27    6-Cl-2-i-C3F7          4.40(br.2H)，7.12(d.1H)，7.41(dd.
                                              1H).
IV′-12       Q27    6-F-2-i-C3F7
IV′-13       Q27    6-i-C3F7               4.28(br.2H)，7.04(dd.1H)，7.18(m.
                                              1H)，8.07(d.1H).
IV′-14       Q27    4，6-Cl2-2-i-C3F7     4.80(br.2H)，7.53(d.1H).
IV′-15       Q27    6-MeO-2-i-C3F7         3.96(s.3H)，4.03(br.2H)，6.91(d.
                                              1H)，7.10(dd.1H).
IV′-16       Q27    6-MeS-2-i-C3F7         2.58(s.3H)，4.00(br.2H)，6.91(d.
                                              1H)，7.22(dd.1H).
IV′-17       Q27    6-MeSO-2-i-C3F7
                              表1(续)
No.            Q′      Ym                      mp(℃)或1H-NMR[δ(ppm/CDCl3)]
IV′-18        Q27      6-MeSO2-2-I-C3F7
IV′-19        Q32      4-Me-2-i-C3F7         2.46(s.3H)，3.94(br.2H)，8.15(s.1H).
IV′-20        Q32      4-Me-6-i-C3F7         2.49(s.3H)，4.35(br.2H)，8.55(s.1H).
IV′-21        Q34      5-i-C3F7              5.0(br.2H)，8.01(s.1H)，8.31(s.1H).
IV′-22        Q27      2-OCF2CHF2            3.43(br.2H)，6.13(tt.1H)，6.88(d.
                                                1H)，7.08(dd.1H)，7.74(d.1H).
IV′-23        Q27      2-OCHF2                3.60(br.2H)，6.72(d.1H)，7.07(dd.
                                                1H)，7.26(dd.1H)，7.63(d.1H).
IV′-24        Q27      6-Me-2-OCHF2           1.30(s.3H)，3.45(br.2H)，6.58(d.1H)，
                                                6.98(d.1H)，7.30(t.1H).
IV′-25        Q27      2-SCHF2                3.81(br.2H)，6.94(dd.1H)，7.24(t.
                                                1H)，7.25(d.1H)，8.06(d.1H).
IV′-26        Q27      6-Me-2-SCHF2           44-46℃
IV′-27        Q27      2-OCH(CF3)2           3.70(br.2H)，6.40(m.1H)，6.76(d.1H)，
                                                 7.08(dd.1H)，7.59(d.1H).
IV′-28        Q27      6-Me-2-OCH(CF3)2      2.33(s.3H)，3.45(br.2H)，6.49(m.1H)，
                                                 6.64(d.1H)，7.03(d.1H).
IV′-29        Q27      6-Cl-2-OCH(CF3)2      3.89(br.2H)，6.24(m.1H)，6.76(d.1H)，
                                                 7.16(d.1H).
IV′-30        Q27      6-F-2-OCH(CF3)2
IV′-31        Q27      6-OMe-2-OCH(CF3)2     3.15-3.60(br.2H)，3.95(s.3H)，6.15(m.
                                                 1H)，6.38(d.1H)，6.99(d.1H).
IV′-32        Q27      6-Cl-2-SCH(CF3)2
IV′-33        Q27      6-Me-2-SCH(CF3)2
                               表1(续)
No.            Q′     Ym                        mp(℃)或1H-NMR[δ(ppm/CDCl3)]
IV′-34        Q27     6-F-2-SCH(CF3)2
IV′-35        Q27     6-OMe-2-SCH(CF3)2
IV′-36        Q27     2-OCF2CHFOCF3
IV′-37        Q27     6-Me-2-OCF2CHFOCF3     2.35(s.3H)，3.50(br.2H)，6.31(dt.
                                                 1H)，6.77(d.1H)，7.01(d.1H).
IV′-38        Q27     6-Cl-2-OCF2CHFOCF3
IV′-39        Q27     2-OCF2CHFO-n-C3F7     3.20(br.2H)，6.43(dt.1H)，6.84(d.
                                                 1H)，7.08(dd.1H)，7.73(d.1H).
IV′-40        Q27     6-Me-2-OCF2CHFO-         2.35(s.3H)，3.60(br.2H)，6.50(dt.
                                 n-C3F7       1H)，6.74(d.1H)，7.02(d.1H).
IV′-41        Q27     6-Cl-2-OCF2CHFO-         3.40(br.2H)，6.37(dt.1H)，6.85(d.
                                 n-C3F7       1H)，7.14(d.1H).
IV′-42        Q27     6-Me-2-OCF2CHFCF3      2.36(s.3H)，3.30(br.2H)，5.35(m.
                                                 1H)，6.76(d.1H)，7.01(d.1H).
IV′-43        Q27     6-Me-2-OCF＝CFCF3        2.04(s.3H)，3.10(br.2H)，6.65(d.
                                                 0.5H)，6.69(d.0.5H)，7.03(d.1H).
                                                (E，Z混合物)
IV′-44        Q27     6-Me-2-OCH(CF3)2       2.20(s.3H)，3.20-3.60(br.2H)，
                                                 6.41(m.1H)，6.67(s.1H)，7.55(s.1H).
IV′-45        Q27     6-Me-2-OCF2CHF2        2.37(s.3H)，3.40(br.2H)，6.16(tt.
                                                 1H)，6.79(d.1H)，7.06(d.1H).
IV′-46        Q27     6-Cl-2-OCF2CHF3        3.50(br.2H)，6.11(tt.1H)，6.88(d.
                                                 1H)，7.15(d.1H).
IV′-47        Q27     6-Me-2-OCH2C2F5       2.31(s.3H)，3.33(br.2H)，4.75(t.
                                                 2H)，6.55(d.1H)，6.98(d.1H).
通式(I)：
                                  表2(Z1＝Z2＝O)
Q         No.         Xn        R1    R2        R3    W        Ym                  mp(℃)
Q1        1-1         3-Cl      H      i-Pr        H      O        H
Q1        1-2         3-Cl      H      i-Pr        H      O        3-Me-5-C2F5
Q1        1-3         3-Cl      H      i-Pr        H      S        4，5-Br2           143
Q1        1-4         3-Br      H      i-Pr        H      O        3-Me-5-n-C3F7
Q1        1-5         3-NO2    H      i-Pr        H      O        3-Me-5-i-C3F7
Q1        1-6         3-I       H      i-Pr        H      S        H
Q1        1-7         3-I       H      i-Pr        H      S        3-Me                207
Q1        1-8         3-I       H      i-Pr        H      S        5-Cl
Q1        1-9         3-I       H      i-Pr        H      S        5-C2F5
Q1        1-10        3-I       H      i-Pr        H      S        5-n-C3F7
Q1        1-11        3-I       H      i-Pr        H      S        5-i-C3F7
Q1        1-12        3-I       H      i-Pr        H      S        3-Me-5-t-Bu         160
Q1        1-13        3-I       H      i-Pr        H      S        3-Me-5-Br
Q1        1-14        3-I       H      i-Pr        H      S        3-Me-5-C2F5
Q1        1-15        3-I       H      i-Pr        H      S        3-Me-5-n-C3F7
Q1        1-16        3-I       H      i-Pr        H      S        3-Me-5-i-C3F7
Q1        1-17        3-I       H      i-Pr        H      S        3-Me-4-C2F5
Q1        1-18        3-I       H      i-Pr        H      S        3-Me-4-n-C3F7
Q1        1-19        3-I       H      i-Pr        H      S        3-Me-4-i-C3F7
Q1        1-20        3-I       H      t-Bu        H      NMe      5-i-C3F7
Q1        1-21        3-I       H      t-Bu        H      NMe      5-C2F5
Q1        1-22        3-I       H      t-Bu        H      NMe      5-n-C3F7
Q1        1-23        3-I       H      t-Bu        H      NMe      3-Me-5-i-C3F7
                                表2(续)
Q       No.       Xn         R1      R2                       R3    W        Ym                    mp(℃)
Q1      1-24      3-I        H        CH(CH3)CH2SCH3         H      S        3-Me-5-i-C3F7
Q1      1-25      3-I        H        CH(CH3)CH2SOCH3        H      S        3-Me-5-i-C3F7
Q1      1-26      3-I        H        CH(CH3)CH2SO2CH3      H      S        3-Me-5-i-C3F7
Q1      1-27      3-I        H        C(CH3)2CH2SCH3        H      S        3-Me-5-i-C3F7
Q1      1-28      3-I        H        C(CH3)2CH2SOCH3       H      S        3-Me-5-i-C3F7
Q1      1-29      3-I        H        C(CH3)2CH2SO2CH3     H      S        3-Me-5-i-C3F7
Q1      1-30      3-I        H        CH(CH3)CH2NHAc           H      S        3-Me-5-i-C3F7
Q1      1-31      3-I        H        C(CH3)2CH2NHAc          H      S        3-Me-5-i-C3F7
Q1      1-32      3-I        H        CH(CH3)CH2CH2OCH3     H      S        3-Me-5-i-C3F7
Q1      1-33      3-I        H        C(CH3)2CH2CH2OCH3    H      S        3-Me-5-i-C3F7
Q1      1-34      3-I        Et       Et                          H      O        H
Q1      1-35      3-I        Et       Et                          H      O        3-Me-5-C2F5
Q1      1-36      3-I        Et       Et                          H      O        3-Me-5-n-C3F7
Q1      1-37      3-I        Et       Et                          H      O        3-Me-5-i-C3F7
Q1      1-38      3-I        Et       Et                          H      O        5-Cl
Q1      1-39      3-I        Et       Et                          H      O        5-Br
Q1      1-40      3-I        Et       Et                          H      O        5-n-C3F7
Q1      1-41      6-I        H        i-Pr                        H      S        3-Me-5-t-Bu            97
Q1      1-42      6-I        H        i-Pr                        H      S        3-Me                   168
Q1      1-43      3-CF3     H        i-Pr                        H      NMe      3-Me-5-C2F5
Q1      1-44      3-Ph       H        i-Pr                        H      NMe      3-Me-5-n-C3F7
Q1      1-45      3-SOCF3   H        i-Pr                        H      NMe      3-Me-5-i-C3F7
Q1      1-46      3-C2F5   H        i-Pr                        H      NMe      3-Me-5-C2F5
                                      表2(续)
Q       No.       Xn               R1    R2                       R3     W        Ym                mp(℃)
Q1      1-47      3-I-4-Cl         H      i-Pr                      H        NMe      3-Me-5-n-C3F7
Q1      1-48      3-I-4-CF3       H      i-Pr                      H        S        3-Me-5-i-C3F7
Q1      1-49      3-CF3-4-Cl      H      i-Pr                      H        S        3-Me-5-C2F5
Q1      1-50      3-OCF2O-4       H      i-Pr                      H        S        3-Me-5-n-C3F7
Q1      1-51      3-OCF2CF2O-4   H      i-Pr                      H        S        3-Me-5-i-C3F7
Q2      2-1       3-I              H      i-Pr                      H        S        2-Me-5-C2F5
Q2      2-2       3-I              H      i-Pr                      H        S        2-Me-5-n-C3F7
Q2      2-3       3-I              H      i-Pr                      H        S        2-Me-5-i-C3F7
Q2      2-4       3-I              H      i-Pr                      H        S        4-Me-5-C2F5
Q2      2-5       3-I              H      i-Pr                      H        S        4-Me-5-n-C3F7
Q2      2-6       3-I              H      i-Pr                      H        S        4-Me-5-i-C3F7
Q2      2-7       3-I              H      t-Bu                      H        NMe      5-i-C3F7
Q2      2-8       3-I              H      t-Bu                      H        NMe      5-C2F5
Q2      2-9       3-I              H      t-Bu                      H        NMe      5-n-C3F7
Q2      2-10      3-I              H      t-Bu                      H        NMe      4-Me-5-i-C3F7
Q2      2-11      3-I              H      CH(CH3)CH2SCH3        H        S        4-Me-5-i-C3F7
Q2      2-12      3-I              H      CH(CH3)CH2SOCH3       H        S        4-Me-5-i-C3F7
Q2      2-13      3-I              H      CH(CH3)CH2SO2CH3     H        S        4-Me-5-i-C3F7
Q2      2-14      3-I              H      C(CH3)2CH2SCH3       H        S        4-Me-5-i-C3F7
Q2      2-15      3-I              H      C(CH3)2CH2SOCH3      H        S        2-Me-5-i-C3F7
Q2      2-16      3-I              H      C(CH3)2CH2SO2CH3    H        S        2-Me-5-i-C3F7
Q2      2-17      3-I              H      CH(CH3)CH2NHAc          H        S        2-Me-5-i-C3F7
Q2      2-18      3-I              H      C(CH3)2CH2NHAc         H        S        2-Me-5-i-C3F7
                                   表2(续)
Q         No.         Xn         R1       R2                          R3     W      Ym                mp(℃)
Q2        2-19        3-I        H         CH(CH3)CH2CH2OCH3       H       S       2-Me-5-i-C3F7
Q2        2-20        3-I        H         C(CH3)2CH2CH2OCH3      H       S      4-Me-5-i-C3F7
Q2        2-21        3-I        Et        Et                            H       O      H
Q2        2-22        3-I        Et        Et                            H       O      2-Me-5-C2F5
Q2        2-23        3-I        Et        Et                            H       O      2-Me-5-n-C3F7
Q2        2-24        3-I        Et        Et                            H       O      4-Me-5-i-C3F7
                                  表3(Z2＝Z2＝O)
Q       No.        Xn       R1      R2      R3    W        Ym                  mp(℃)
Q4      4-1        H        H        i-Pr      H      O        5-Me                185
Q4      4-2        3-Cl     H        i-Pr      H      O        H
Q4      4-3        3-Cl     H        i-Pr      H      O        4-Me-5-C2F5
Q4      4-4        3-Cl     H        i-Pr      H      O        4，5-Br2
Q4      4-5        3-Cl     H        i-Pr      H      O        5-Me                136
Q4      4-6        3-Cl     H        i-Pr      H      O        5-(4-Br-Ph)         158
Q4      4-7        3-Cl     H        i-Pr      H      O        4-Me-5-(4-Cl-Ph)    184
Q4      4-8        6-Cl     H        i-Pr      H      O        4-Me-5-(4-Cl-Ph)    101
Q4      4-9        3-Br     H        i-Pr      H      O        4-Me-5-n-C3F7
Q4      4-10       3-NO2   H        i-Pr      H      O        4-Me-5-i-C3F7
Q4      4-11       3-I      H        i-Pr      H      O        4-Me                144
Q4      4-12       3-I      H        i-Pr      H      O        4-Me-5-CF3          151
Q4      4-13       3-I      H        i-Pr      H      S        H
Q4      4-14       3-I      H        i-Pr      H      S        4-Me
Q4      4-15       3-I      H        i-Pr      H      S        5-Cl
Q4      4-16       3-I      H        i-Pr      H      S        5-C2F5
Q4      4-17       3-I      H        i-Pr      H      S        5-n-C3F7
Q4      4-18       3-I      H        i-Pr      H      S        5-i-C3F7
Q4      4-19       3-I      H        i-Pr      H      S        4-Me-5-t-Bu
Q4      4-20       3-I      H        i-Pr      H      S        4-Me-5-Br
Q4      4-21       3-I      H        i-Pr      H      S        4-Me-5-C2F5
Q4      4-22       3-I      H        i-Pr      H      S        4-Me-5-n-C3F7
Q4      4-23       3-I      H        i-Pr      H      S        4-Me-5-i-C3F7
                           表3(续)
Q       No.       Xn         R1      R2                      R3      W          Ym                mp(℃)
Q4      4-24      3-I        H        t-Bu                      H        NMe        5-i-C3F7
Q4      4-25      3-I        H        t-Bu                      H        NMe        5-C2F5
Q4      4-26      3-I        H        t-Bu                      H        NMe        5-n-C3F7
Q4      4-27      3-I        H        t-Bu                      H        NMe        4-Me-5-i-C3F7
Q4      4-28      3-I        H        CH(CH3)CH2SCH          H        S          4-Me-5-i-C3F7
Q4      4-29      3-I        H        CH(CH3)CH2SOCH3       H        S          4-Me-5-i-C3F7
Q4      4-30      3-I        H        CH(CH3)CH2SO2CH3     H        S          4-Me-5-i-C3F7
Q4      4-31      3-I        H        C(CH3)2CH2SCH3       H        S          4-Me-5-i-C3F7
Q4      4-32      3-I        H        C(CH3)2CH2SOCH3      H        S          4-Me-5-i-C3F7
Q4      4-33      3-I        H        C(CH3)2CH2SO2CH3    H        S          4-Me-5-i-C3F7
Q4      4-34      3-I        H        CH(CH3)CH2NHAc          H        S          4-Me-5-i-C3F7
Q4      4-35      3-I        H        C(CH3)2CH2NHAc         H        S          4-Me-5-i-C3F7
Q4      4-36      3-I        H        CH(CH3)CH2CH2OCH3     H        S          4-Me-5-i-C3F7
Q4      4-37      3-I        H        C(CH3)2CH2CH2OCH3   H        S          4-Me-5-i-C3F7
Q4      4-38      3-I        Et       Et                         H        O          H
Q4      4-39      3-I        Et       Et                         H        O          4-Me-5-C2F5
Q4      4-40      3-I        Et       Et                         H        O          4-Me-5-n-C3F7
Q4      4-41      3-I        Et       Et                         H        O          4-Me-5-i-C3F7
Q4      4-42      3-I        Et       Et                         H        O          5-Cl
Q4      4-43      3-I        Et       Et                         H        O          5-Br
Q4      4-44      3-I        Et       Et                         H        O          5-n-C3F7
Q4      4-45      6-I        H        i-Pr                       H        O          4-Me-5-CF3          143
Q4      4-46      3-CF3     H        i-Pr                       H        NMe        4-Me-5-C2F5
                                        表3(续)
Q       No.       Xn                  R1      R2       R3      W          Ym                    mp(℃)
Q4      4-47      3-Ph                H        i-Pr       H        NMe        4-Me-5-n-C3F7
Q4      4-48      3-SOCF3            H        i-Pr       H        NMe        4-Me-5-i-C3F7
Q4      4-49      3-C2F5            H        i-Pr       H        NMe        4-Me-5-C2F5
Q4      4-50      3-I-4-Cl            H        i-Pr       H        NMe        4-Me-5-n-C3F7
Q4      4-51      3-I-4-CF3          H        i-Pr       H        S          4-Me-5-i-C3F7
Q4      4-52      3-CF3-4-Cl         H        i-Pr       H        S          4-Me-5-C2F5
Q4      4-53      3-OCF2O-4          H        i-Pr       H        S          4-Me-5-n-C3F7
Q4      4-54      3-OCF2CF2O-4      H        i-Pr       H        S          4-Me-5-i-C3F7
Q5      5-1       3-Cl                 H        i-Pr       H        O          H
Q5      5-2       3-Cl                 H        i-Pr       H        O          3-Me-5-Cl
Q5      5-3       3-Cl                 H        i-Pr       H        O          3，5-Br2
Q5      5-4       3-Cl                 H        i-Pr       H        NMe        3-Me                 180
Q5      5-5       3-Cl                 H        i-Pr       H        NMe        3-Me-5-OMe           220
Q5      5-6       3-Cl                 H        n-Pr       H        NMe        3-Me-5-OMe           90
Q5      5-7       3-Cl                 H        n-Pr       H        NMe        3-Me-5-OPh           190
Q5      5-8       6-Cl                 H        i-Pr       H        NMe        3-Me-5-OPh           245
Q5      5-9       6-Cl                 H        i-Pr       H        NMe        3-Me-5-OMe           175
Q5      5-10      3-Br                 H        i-Pr       H        O          3，5-Me2
Q5      5-11      3-NO2               H        i-Pr       H        O          3，5-Me2
Q5      5-12      3-I                  H        i-Pr       H        O          3-CF3
Q5      5-13      3-I                  H        i-Pr       H        O          5-CF3
Q5      5-14      3-I                  H        i-Pr       H        S          H
Q5      5-15      3-I                  H        i-Pr       H        S          3-Me
                                      表3(续)
Q       No.         Xn         R1      R2                      R3       W        Ym                 mp(℃)
Q5      5-16        3-I        H        i-Pr                      H        S        5-Cl
Q5      5-17        3-I        H        i-Pr                      H        S        5-C2F5
Q5      5-18        3-I        H        i-Pr                      H        S        5-n-C3F7
Q5      5-19        3-I        H        i-Pr                      H        S        5-i-C3F7
Q5      5-20        3-I        H        i-Pr                      H        S        3-C2F5
Q5      5-21        3-I        H        i-Pr                      H        S        3-n-C3F7
Q5      5-22        3-I        H        i-Pr                      H        S        3-i-C3F7
Q5      5-23        3-I        H        i-Pr                      H        S        3-Me-5-Br
Q5      5-24        3-I        H        i-Pr                      H        S        3-Me-5-C2F5
Q5      5-25        3-I        H        i-Pr                      H        S        3-Me-5-n-C3F7
Q5      5-26        3-I        H        i-Pr                      H        S        3-Me-5-i-C3F7
Q5      5-27        3-I        H        t-Bu                      H        NMe      5-i-C3F7
Q5      5-28        3-I        H        t-Bu                      H        NMe      5-C2F5
Q5      5-29        3-I        H        t-Bu                      H        NMe      5-n-C3F7
Q5      5-30        3-I        H        CH(CH3)CH2SCH3        H        NMe      3，5-Me2
Q5      5-31        3-I        H        CH(CH3)CH2SOCH3       H        NMe      3，5-Me2
Q5      5-32        3-I        H        CH(CH3)CH2SO2CH3     H        NMe      3，5-Me2
Q5      5-33        3-I        H        C(CH3)2CH2SCH3       H        NMe      3，5-Me2
Q5      5-34        3-I        H        C(CH3)2CH2SOCH3      H        NMe      3，5-Me2
Q5      5-35        3-I        H        C(CH3)2CH2SO2CH3    H        NMe      3，5-Me2
Q5      5-36        3-I        H        CH(CH3)CH2NHAc          H        NMe      3，5-Me2
Q5      5-37        3-I        H        C(CH3)2CH2NHAc         H        NMe      3，5-Me2
Q5      5-38        3-I        H        CH(CH3)CH2CH2OCH3    H        NMe      3，5-Me2
                                表3(续)
Q       No.       Xn               R1    R2                        R3      W        Ym                 mp(℃)
Q5      5-39      3-I              H      C(CH3)2CH2CH2OCH3    H        NMe      3，5-Me2
Q5      5-40      3-I              Et     Et                          H        O        H
Q5      5-41      3-I              Et     Et                          H        O        3-Me-5-C2F5
Q5      5-42      3-I              Et     Et                          H        O        3-Me-5-n-C3F7
Q5      5-43      3-I              Et     Et                          H        O        3-Me-5-i-C3F7
Q5      5-44      3-I              Et     Et                          H        O        5-Cl
Q5      5-45      3-I              Et     Et                          H        O        5-Br
Q5      5-46      3-I              Et     Et                          H        O        5-n-C3F7
Q5      5-47      3-I              Et     Et                          H        O        5-n-C3F7
Q5      5-48      3-CF3           H      i-Pr                        H        NMe      3-Me-5-C2F5
Q5      5-49      3-Ph             H      i-Pr                        H        NMe      3-Me-5-n-C3F7
Q5      5-50      3-SOCF3         H      i-Pr                        H        NMe      3-Me-5-i-C3F7
Q5      5-51      3-C2F5         H      i-Pr                        H        NMe      3-Me-5-C2F5
Q5      5-52      3-I-4-Cl         H      i-Pr                        H        NMe      3-Me-5-n-C3F7
Q5      5-53      3-I-4-CF3       H      i-Pr                        H        S        3-Me-5-i-C3F7
Q5      5-54      3-CF3-4-Cl      H      i-Pr                        H        S        3-Me-5-C2F5
Q5      5-55      3-OCF2O-4       H      i-Pr                        H        S        3-Me-5-n-C3F7
Q5      5-56      3-OCF2CF2O-4   H      i-Pr                        H        S        3-Me-5-i-C3F7
Q6      6-1       3-Cl              H      i-Pr                        H        O        H
Q6      6-2       3-Cl              H      i-Pr                        H        O        4-Me-3-C2F5
Q6      6-3       3-Cl              H      i-Pr                        H        O        3，4-Br2
Q6      6-4       3-Br              H      i-Pr                        H        O        4-Me-3-n-C3F7
Q6      6-5       3-NO2            H      i-Pr                        H        O        4-Me-3-i-C3F7
                                表3(续)
Q       No.         Xn         R1      R2                     R3      W        Ym                mp(℃)
Q6      6-6         3-NO2     H        i-Pr                     H        NMe      3-Me             176
Q6      6-7         3-I        H        i-Pr                     H        O        4-Me-3-Et         85
Q6      6-8         3-I        H        i-Pr                     H        O        4-Me-3-CF3      103
Q6      6-9         3-I        H        i-Pr                     H        S        H
Q6      6-10        3-I        H        i-Pr                     H        S        4-Me
Q6      6-11        3-I        H        i-Pr                     H        S        3-Cl
Q6      6-12        3-I        H        i-Pr                     H        S        3-C2F5
Q6      6-13        3-I        H        i-Pr                     H        S        3-n-C3F7
Q6      6-14        3-I        H        i-Pr                     H        S        3-i-C3F7
Q6      6-15        3-I        H        i-Pr                     H        S        4-Me-3-t-Bu
Q6      6-16        3-I        H        i-Pr                     H        S        4-Me-3-Br
Q6      6-17        3-I        H        i-Pr                     H        S        4-Me-3-C2F5
Q6      6-18        3-I        H        i-Pr                     H        S        4-Me-3-n-C3F7
Q6      6-19        3-I        H        i-Pr                     H        S        4-Me-3-i-C3F7
Q6      6-20        3-I        H        t-Bu                     H        NMe      3-i-C3F7
Q6      6-21        3-I        H        t-Bu                     H        NMe      3-C2F5
Q6      6-22        3-I        H        t-Bu                     H        NMe      3-n-C3F7
Q6      6-23        3-I        H        t-Bu                     H        NMe      4-Me-3-i-C3F7
Q6      6-24        3-I        H        CH(CH3)CH2SCH3       H        S        4-Me-3-i-C3F7
Q6      6-25        3-I        H        CH(CH3)CH2SOCH3      H        S        4-Me-3-i-C3F7
Q6      6-26        3-I        H        CH(CH3)CH2SO2CH3    H        S        4-Me-3-i-C3F7
Q6      6-27        3-I        H        C(CH3)2CH2SCH3      H        S        4-Me-3-i-C3F7
Q6      6-28        3-I        H        C(CH3)2CH2SOCH3     H        S        4-Me-3-i-C3F7
                                           表3(续)
Q       No.         Xn                R1       R2                        R3      W        Ym                mp(℃)
Q6      6-29        3-I               H         C(CH3)2CH2SO2CH3     H        S        4-Me-3-i-C3F7
Q6      6-30        3-I               H         CH(CH3)CH2NHAc           H        S        4-Me-3-i-C3F7
Q6      6-31        3-I               H         C(CH3)2CH2NHAc          H        S        4-Me-3-i-C3F7
Q6      6-32        3-I               H         CH(CH3)CH2CH2OCH3      H        S        4-Me-3-i-C3F7
Q6      6-33        3-I               H         C(CH3)2CH2CH2OCH3    H        S        4-Me-3-i-C3F7
Q6      6-34        3-I               Et        Et                          H        O        H
Q6      6-35        3-I               Et        Et                          H        O        4-Me-3-C2F5
Q6      6-36        3-I               Et        Et                          H        O        4-Me-3-n-C3F7
Q6      6-37        3-I               Et        Et                          H        O        4-Me-3-i-C3F7
Q6      6-38        3-I               Et        Et                          H        O        3-Cl
Q6      6-39        3-I               Et        Et                          H        O        3-Br
Q6      6-40        3-I               Et        Et                          H        O        3-n-C3F7
Q6      6-41        3-CF3            H         i-Pr                        H        NMe      4-Me-3-C2F5
Q6      6-42        3-Ph              H         i-Pr                        H        NMe      4-Me-3-n-C3F7
Q6      6-43        3-SOCF3          H         i-Pr                        H        NMe      4-Me-3-i-C3F7
Q6      6-44        3-C2F5          H         i-Pr                        H        NMe      4-Me-3-C2F5
Q6      6-45        3-I-4-Cl           H         i-Pr                        H        NMe      4-Me-3-n-C3F7
Q6      6-46        3-I-4-CF3        H         i-Pr                        H        S        4-Me-3-i-C3F7
Q6      6-47        3-CF3-4-Cl       H         i-Pr                        H        S        4-Me-3-C2F5
Q6      6-48        3-OCF2O-4        H         i-Pr                        H        S        4-Me-3-n-C3F7
Q6      6-49        3-OCF2CF2O-4    H         i-Pr                        H        S        4-Me-3-i-C3F7
                                表4(Z1＝Z2＝O)
Q       No.       Xn          R1      R2        R3      W        Ym              mp(℃)
Q8      8-1       3-Cl        H        i-Pr        H        S        H               137
Q8      8-2       3-Cl        H        i-Pr        H        S        4-Me            175
Q8      8-3       3-Cl        H        i-Pr        H        S        4-CF3          185
Q8      8-4       3-Cl        H        i-Pr        H        S        4-Ph            175
Q8      8-5       3-Cl        H        i-Pr        H        S        4-Ph-5-Cl       205
Q8      8-6       3-Cl        H        i-Pr        H        O        4-Me-5-Cl
Q8      8-7       3-Cl        H        i-Pr        H        O        4，5-Br2
Q8      8-8       3-Cl        H        i-Pr        H        NMe      4-Me
Q8      8-9       3-Cl        H        i-Pr        H        NMe      4-Me-5-OMe
Q8      8-10      3-Cl        H        n-Pr        H        NMe      4-Me-5-OMe
Q8      8-11      3-Cl        H        n-Pr        H        NMe      4-Me-5-OPh
Q8      8-12      6-Cl        H        i-Pr        H        S        4-CH3          155
Q8      8-13      6-Cl        H        i-Pr        H        S        4-CF3          165
Q8      8-14      6-Cl        H        i-Pr        H        S        4-Ph            155
Q8      8-15      6-Cl        H        i-Pr        H        S        4-Ph-5-Cl       155
Q8      8-16      3-Br        H        i-Pr        H        O        4，5-Me2
Q8      8-17      3-NO2      H        i-Pr        H        O        4，5-Me2
                                         表4(续)
Q       No.       Xn         R1    R2                    R3      W        Ym        mp(℃)
Q8      8-18      3-I        H      i-Pr                    H        O        4-CF3
Q8      8-19      3-I        H      i-Pr                    H        O        5-CF3
Q8      8-20      3-I        H      i-Pr                    H        S        H
Q8      8-21      3-I        H      i-Pr                    H        S        4-Me
Q8      8-22      3-I        H      i-Pr                    H        S        5-Cl
Q8      8-23      3-I        H      i-Pr                    H        S        5-C2F5
Q8      8-24      3-I        H      i-Pr                    H        S        5-n-C3F7
Q8      8-25      3-I        H      i-Pr                    H        S        5-i-C3F7
Q8      8-26      3-I        H      i-Pr                    H        S        4-C2F5
Q8      8-27      3-I        H      i-Pr                    H        S        4-n-C3F7
Q8      8-28      3-I        H      i-Pr                    H        S        4-i-C3F7
Q8      8-29      3-I        H      i-Pr                    H        S        4-Me-5-Br
Q8      8-30      3-I        H      i-Pr                    H        S        4-Me-5-C2F5
Q8      8-31      3-I        H      i-Pr                    H        S        4-Me-5-n-C3F7
Q8      8-32      3-I        H      i-Pr                    H        S        4-Me-5-i-C3F7
Q8      8-33      3-I        H      t-Bu                    H        NMe      5-i-C3F7
Q8      8-34      3-I        H      t-Bu                    H        NMe      5-C2F5
Q8      8-35      3-I        H      t-Bu                    H        NMe      5-n-C3F7
Q8      8-36      3-I        H      CH(CH3)CH2SCH3      H        NMe      4，5-Me2
Q8      8-37      3-I        H      CH(CH3)CH2SO2CH3   H        NMe      4，5-Me2
Q8      8-38      3-I        H      CH(CH3)CH2SOCH3     H        NMe      4，5-Me2
Q8      8-39      3-I        H      C(CH3)2CH2SCH3     H        NMe      4，5-Me2
Q8      8-40      3-I        H      C(CH3)2CH2SOCH3    H        NMe      4，5-Me2
                                         表4(续)
Q       No.       Xn               R1      R2                        R3       W          Ym          mp(℃)
Q8      8-41      3-I              H        C(CH3)2CH2SO2CH3     H        NMe        4，5-Me2
Q8      8-42      3-I              H        CH(CH3)CH2NHAc           H        NMe        4，5-Me2
Q8      8-43      3-I              H        C(CH3)2CH2NHAc          H        NMe        4，5-Me2
Q8      8-44      3-I              H        CH(CH3)CH2CH2OCH3      H        NMe        4，5-Me2
Q8      8-45      3-I              H        C(CH3)2CH2CH2OCH3    H        NMe        4，5-Me2
Q8      8-46      3-I              Et       Et                          H        O          H
Q8      8-47      3-I              Et       Et                          H        O          5-C2F5
Q8      8-48      3-I              Et       Et                          H        O          4-n-C3F7
Q8      8-49      3-I              Et       Et                          H        O          4-i-C3F7
Q8      8-50      3-I              Et       Et                          H        O          5-Cl
Q8      8-51      3-I              Et       Et                          H        O          5-Br
Q8      8-52      3-I              Et       Et                          H        O          5-n-C3F7
Q8      8-53      3-I              Et       Et                          H        S          4-(4-Cl-Ph)    139
Q8      8-54      3-CF3           H        i-Pr                        H        NMe        5-C2F5
Q8      8-55      3-Ph             H        i-Pr                        H        NMe        4-n-C3F7
Q8      8-56      3-SOCF3         H        i-Pr                        H        NMe        4-i-C3F7
Q8      8-57      3-C2F5         H        i-Pr                        H        NMe        5-C2F5
Q8      8-58      3-I-4-Cl         H        i-Pr                        H        NMe        4-n-C3F7
Q8      8-59      3-I-4-CF3       H        i-Pr                        H        S          4-i-C3F7
Q8      8-60      3-CF3-4-Cl      H        i-Pr                        H        S          5-C2F5
Q8      8-61      3-OCF2O-4       H        i-Pr                        H        S          4-n-C3F7
Q8      8-62      3-OCF2CF2O-4   H        i-Pr                        H        S          4-i-C3F7
Q8      8-63      3-I               H        i-Pr                        H        S          4-S-Et          86
                            表4(续)
Q       No.       Xn         R1      R2        R3      W        Ym                  mp(℃)
Q8      8-64      6-I        H        i-Pr        H        S        4-S-Et              135
Q8      8-65      3-I        H        i-Pr        H        S        4-Me-5-CO2-Et
                                                                    无定形固体
Q9      9-1       3-Cl       H        i-Pr        H        O        H
Q9      9-2       3-Cl       H        i-Pr        H        O        5-Me-2-C2F5
Q9      9-3       3-Cl       H        i-Pr        H        O        2，5-Br2
Q9      9-4       3-Cl       H        i-Pr        H        S        2-Ph                131
Q9      9-5       3-Br       H        i-Pr        H        O        5-Me-2-n-C3F7
Q9      9-6       3-NO2     H        i-Pr        H        O        5-Me-2-i-C3F7
Q9      9-7       3-I        H        i-Pr        H        O        5-Me-2-CF3
Q9      9-8       3-I        H        i-Pr        H        S        H
Q9      9-9       3-I        H        i-Pr        H        S        2-Me
Q9      9-10      3-I        H        i-Pr        H        S        2-Cl
Q9      9-11      3-I        H        i-Pr        H        S        2-C2F5
Q9      9-12      3-I        H        i-Pr        H        S        2-n-C3F7
Q9      9-13      3-I        H        i-Pr        H        S        2-i-C3F7
Q9      9-14      3-I        H        i-Pr        H        S        5-Me-2-t-Bu
Q9      9-15      3-I        H        i-Pr        H        S        5-Me-2-I            135
Q9      9-16      3-I        H        i-Pr        H        S        5-Me-2-C2F5
Q9      9-17      3-I        H        i-Pr        H        S        5-Me-2-n-C3F7
Q9      9-18      3-I        H        i-Pr        H        S        5-Me-2-i-C3F7
Q9      9-19      3-I        H        i-Pr        H        S        5-Me-2-I            191
Q9      9-20      3-I        H        t-Bu        H        NMe      2-i-C3F7
                                   表4(续)
Q       No.         Xn           R1      R2                      R3        W        Ym               mp(℃)
Q9      9-21        3-I          H        t-Bu                      H          NMe      2-C2F5
Q9      9-22        3-I          H        t-Bu                      H          NMe      2-n-C3F7
Q9      9-23        3-I          H        t-Bu                      H          NMe      5-Me-2-i-C3F7
Q9      9-24        3-I          H        CH(CH3)CH2SCH3        H          S        5-Me-2-i-C3F7
Q9      9-25        3-I          H        CH(CH3)CH2SOCH3       H          S        5-Me-2-i-C3F7
Q9      9-26        3-I          H        CH(CH3)CH2SO2CH3     H          S        5-Me-2-i-C3F7
Q9      9-27        3-I          H        C(CH3)2CH2SCH3       H          S        5-Me-2-i-C3F7
Q9      9-28        3-I          H        C(CH3)2CH2SOCH3      H          S        5-Me-2-i-C3F7
Q9      9-29        3-I          H        C(CH3)2CH2SO2CH3    H          S        5-Me-2-i-C3F7
Q9      9-30        3-I          H        CH(CH3)CH2NHAc          H          S        5-Me-2-i-C3F7
Q9      9-31        3-I          H        C(CH3)2CH2NHAc         H          S        5-Me-2-i-C3F7
Q9      9-32        3-I          Et       Et                         H          O        H
Q9      9-33        3-I          Et       Et                         H          O        5-Me-2-C2F5
Q9      9-34        3-I          Et       Et                         H          O        5-Me-2-n-C3F7
Q9      9-35        3-I          Et       Et                         H          O        5-Me-2-i-C3F7
Q9      9-36        3-I          Et       Et                         H          O        2-Cl
Q9      9-37        3-I          Et       Et                         H          O        2-Br
Q9      9-38        3-I          Et       Et                         H          O        2-n-C3F7
Q9      9-39        3-CF3       H        i-Pr                       H          NMe      5-Me-2-C2F5
Q9      9-40        3-Ph         H        i-Pr                       H          NMe      5-Me-2-n-C3F7
Q9      9-41        3-SOCF3     H        i-Pr                       H          NMe      5-Me-2-i-C3F7
Q9      9-42        3-C2F5     H        i-Pr                       H          NMe      5-Me-2-C2F5
Q9      9-43        3-I-4-Cl     H        i-Pr                       H          NMe      5-Me-2-n-C3F7
                                表4(续)
Q        No.        Xn                R1      R2        R3      W        Ym               mp(℃)
Q9       9-44       3-I-4-CF3        H        i-Pr        H        S        5-Me-2-i-C3F7
Q9       9-45       3-CF3-4-Cl       H        i-Pr        H        S        5-Me-2-C2F5
Q9       9-46       3-OCF2O-4        H        i-Pr        H        S        5-Me-2-n-C3F7
Q9       9-47       3-OCF2CF2O-4   H        i-Pr        H        S        5-Me-2-i-C3F7
Q10      10-1       3-Cl              H        i-Pr        H        O        H
Q10      10-2       3-Cl              H        i-Pr        H        O        4-Me-2-C2F5
Q10      10-3       3-Cl              H        i-Pr        H        O        2，4-Br2
Q10      10-4       3-Cl              H        i-Pr        H        O        2-Ph
Q10      10-5       3-Br              H        i-Pr        H        O        4-Me-2-n-C3F7
Q10      10-6       3-NO2            H        i-Pr        H        O        4-Me-2-i-C3F7
Q10      10-7       3-I               H        i-Pr        H        S        4-Me             230
Q10      10-8       3-I               H        i-Pr        H        O        4-Me-2-CF3
Q10      10-9       3-I               H        i-Pr        H        S        H
Q10      10-10      3-I               H        i-Pr        H        S        4-Me
Q10      10-11      3-I               H        i-Pr        H        S        2-Cl
Q10      10-12      3-I               H        i-Pr        H        S        2-C2F5
Q10      10-13      3-I               H        i-Pr        H        S        2-n-C3F7
Q10      10-14      3-I               H        i-Pr        H        S        2-i-C3F7
Q10      10-15      3-I               H        i-Pr        H        S        4-Me-2-t-Bu
Q10      10-16      3-I               H        i-Pr        H        S        4-Me-2-I
Q10      10-17      3-I               H        i-Pr        H        S        4-Me-2-C2F5
Q10      10-18      3-I               H        i-Pr        H        S        4-Me-2-n-C3F7
Q10      10-19      3-I               H        i-Pr        H        S        4-Me-2-i-C3F7
                                表4(续)
Q        No.        Xn         R1      R2                      R3      W          Ym                  mp(℃)
Q10      10-20      6-I        H        i-Pr                      H        S          4-Me                198
Q10      10-21      3-I        H        t-Bu                      H        NMe        2-i-C3F7
Q10      10-22      3-I        H        t-Bu                      H        NMe        2-C2F5
Q10      10-23      3-I        H        t-Bu                      H        NMe        2-n-C3F7
Q10      10-24      3-I        H        t-Bu                      H        NMe        4-Me-2-i-C3F7
Q10      10-25      3-I        H        CH(CH3)CH2SCH3        H        S          4-Me-2-i-C3F7
Q10      10-26      3-I        H        CH(CH3)CH2SOCH3       H        S          4-Me-2-i-C3F7
Q10      10-27      3-I        H        CH(CH3)CH2SO2CH3     H        S          4-Me-2-i-C3F7
Q10      10-28      3-I        H        C(CH3)2CH2SCH3       H        S          4-Me-2-i-C3F7
Q10      10-29      3-I        H        C(CH3)2CH2SOCH3      H        S          4-Me-2-i-C3F7
Q10      10-30      3-I        H        C(CH3)2CH2SO2CH3    H        S          4-Me-2-i-C3F7
Q10      10-31      3-I        H        CH(CH3)CH2MHAc          H        S          4-Me-2-i-C3F7
Q10      10-32      3-I        H        C(CH3)2CH2NHAc         H        S          4-Me-2-i-C3F7
Q10      10-33      3-I        Et       Et                         H        O          H
Q10      10-34      3-I        Et       Et                         H        O          4-Me-2-C2F5
Q10      10-35      3-I        Et       Et                         H        O          4-Me-2-n-C3F7
Q10      10-36      3-I        Et       Et                         H        O          4-Me-2-i-C3F7
Q10      10-37      3-I        Et       Et                         H        O          2-Cl
Q10      10-38      3-I        Et       Et                         H        O          2-Br
Q10      10-39      3-I        Et       Et                         H        O          2-n-C3F7
Q10      10-40      3-CF3     H        i-Pr                       H        NMe        4-Me-2-C2F5
Q10      10-41      3-Ph       H        i-Pr                       H        NMe        4-Me-2-n-C3F7
Q10      10-42      3-SOCF3   H        i-Pr                       H        NMe        4-Me-2-i-C3F7
                            表4(续)
Q        No.        Xn                R1    R2     R3    W        Ym               mp(℃)
Q10      10-43      3-C2F5         H      i-Pr     H      NMe      4-Me-2-C2F5
Q10      10-44      3-I-4-Cl          H      i-Pr     H      NMe      4-Me-2-n-C3F7
Q10      10-45      3-I-4-CF3        H      i-Pr     H      S        4-Me-2-i-C3F7
Q10      10-46      3-CF3-4-Cl       H      i-Pr     H      S        4-Me-2-C2F5
Q10      10-47      3-OCF2O-4        H      i-Pr     H      S        4-Me-2-n-C3F7
Q10      10-48      3-OCF2CF2O-4    H      i-Pr     H      S        4-Me-2-i-C3F7
Figure C0081000700491
                            表5(Z1＝Z2＝O)
Q        No.        Xn         R1      R2                        R3      W        Ym          mp(℃)
Q13      13-1       3-Cl       H        i-Pr                        H        S        4-Me
Q13      13-2       3-Cl       H        i-Pr                        H        O        4-Me
Q13      13-3       3-Cl       H        i-Pr                        H        NMe      4-Me
Q13      13-4       3-I        H        i-Pr                        H        S        H
Q13      13-5       3-I        H        i-Pr                        H        S        4-Me        60
Q13      13-6       3-I        H        i-Pr                        H        S        4-Cl
Q13      13-7       3-I        H        i-Pr                        H        S        4-CF3
Q13      13-8       3-I        H        i-Pr                        H        S        4-C2F5
Q13      13-9       3-I        H        i-Pr                        H        S        4-n-C3F7
Q13      13-10      3-I        H        i-Pr                        H        S        4-i-C3F7
Q13      13-11      3-I        H        i-Pr                        H        S        4-t-Bu
Q13      13-12      6-I        H        i-Pr                        H        S        4-Me        73
Q13      13-13      3-I        H        CH(CH3)CH2SCH3          H        S        4-CF3
Q13      13-14      3-I        H        CH(CH3)CH2SOCH3         H        S        4-CF3
Q13      13-15      3-I        H        CH(CH3)CH2SO2CH3       H        S        4-CF3
Q13      13-16      3-I        H        C(CH3)2CH2SCH3         H        S        4-CF3
Q13      13-17      3-I        H        C(CH3)2CH2SOCH3        H        S        4-CF3
Q13      13-18      3-I        H        C(CH3)2CH2SO2CH3     H        S        4-CF3
Q13      13-19      3-I        H        CH(CH3)CH2NHAc           H        S        4-CF3
Q13      13-20      3-I        H        C(CH3)2CH2NHAc          H        S        4-CF3
Q13      13-21      3-I        H        CH(CH3)CH2CH2OCH3      H        S        4-CF3
Q13      13-22      3-I        H        C(CH3)2CH2CH2OCH3    H        S        4-CF3
Q13      13-23      3-I        Et       Et                          H        S        H
                                     表5(续)
Q        No.        Xn                R1      R2        R3      W        Ym          mp(℃)
Q13      13-24      3-I               Et       Et          H        S        4-CF3
Q13      13-25      3-I               Et       Et          H        S        4-CF3
Q13      13-26      3-I               Et       Et          H        S        4-CF3
Q13      13-27      3-I               Et       Et          H        S        4-CF3
Q13      13-28      3-CF3            H        i-Pr        H        S        3-C2F5
Q13      13-29      3-Ph              H        i-Pr        H        S        3-n-C3F7
Q13      13-30      3-SOCF3          H        i-Pr        H        S        3-i-C3F7
Q13      13-31      3-C2F5         H        i-Pr        H        S        3-C2F5
Q13      13-32      3-I-4-Cl          H        i-Pr        H        S        3-n-C3F7
Q13      13-33      3-I-4-CF3        H        i-Pr        H        S        3-i-C3F7
Q13      13-34      3-CF3-4-Cl       H        i-Pr        H        S        3-C2F5
Q13      13-35      3-OCF2O-4        H        i-Pr        H        S        3-n-C3F7
Q13      13-36      3-OCF2CF2O-4    H        i-Pr        H        S        3-i-C3F7
Figure C0081000700511
                            表6(Z1＝Z2＝O)
Q        No.          Xn         R1      R2                     R3      W        Ym          mp(℃)
Q19      19-1         3-Cl       H        i-Pr                     H        O        H
Q19      19-2         3-Cl       H        i-Pr                     H        O        5-C2F5
Q19      19-3         3-Cl       H        i-Pr                     H        S        5-Me        166
Q19      19-4         3-Br       H        i-Pr                     H        O        5-n-C3R7
Q19      19-5         3-NO2     H        i-Pr                     H        O        5-i-C3R7
Q19      19-6         3-I        H        i-Pr                     H        S        H
Q19      19-7         3-I        H        i-Pr                     H        S        5-Me
Q19      19-8         3-I        H        i-Pr                     H        S        5-Cl
Q19      19-9         3-I        H        i-Pr                     H        S        5-CF3       104
Q19      19-10        3-I        H        i-Pr                     H        S        5-C2R5
Q19      19-11        3-I        H        i-Pr                     H        S        5-n-C3F7
Q19      19-12        3-I        H        i-Pr                     H        S        5-i-C3F7
Q19      19-13        3-I        H        i-Pr                     H        S        5-t-Bu
Q19      19-14        3-I        H        i-Pr                     H        S        5-CF3       176
Q19      19-15        3-I        H        t-Bu                     H        NMe      5-i-C3F7
Q19      19-16        3-I        H        t-Bu                     H        NMe      5-C2F5
Q19      19-17        3-I        H        t-Bu                     H        NMe      5-n-C3F7
Q19      19-18        3-I        H        t-Bu                     H        NMe      5-CF3
Q19      19-19        3-I        H        CH(CH3)CH2SCH3       H        S        5-i-C3F7
Q19      19-20        3-I        H        CH(CH3)CH2SOCH3      H        S        5-i-C3F7
Q19      19-21        3-I        H        CH(CH3)CH2SO2CH3    H        S        5-i-C3F7
Q19      19-22        3-I        H        C(CH3)2CH2SCH3      H        S        5-i-C3F7
Q19      19-23        3-I        H        C(CH3)2CH2SOCH3     H        S        5-i-C3F7
                                 表6(续)
Q        No.          Xn                R1      R2                        R3       W        Ym           mp(℃)
Q19      19-24        3-I               H        C(CH3)2CH2SO2CH3     H         S        5-i-C3F7
Q19      19-25        3-I               H        CH(CH3)CH2NHAc           H         S        5-i-C3F7
Q19      19-26        3-I               H        C(CH3)2CH2NHAc          H         S        5-i-C3F7
Q19      19-27        3-I               H        CH(CH3)CH2CH2OCH3      H         S        5-i-C3F7
Q19      19-28        3-I               H        C(CH3)2CH2CH2OCH3    H         S        5-i-C3F7
Q19      19-29        3-I               Et       Et                          H         O        H
Q19      19-30        3-I               Et       Et                          H         O        5-C2F5
Q19      19-31        3-I               Et       Et                          H         O        5-n-C3F7
Q19      19-32        3-I               Et       Et                          H         O        5-i-C3F7
Q19      19-33        3-I               Et       Et                          H         O        5-Cl
Q19      19-34        3-I               Et       Et                          H         S        5-t-Bu          59
Q19      19-35        3-CF3            H        i-Pr                        H         NMe      5-C2F5
Q19      19-36        3-Ph              H        i-Pr                        H         NMe      5-n-C3F7
Q19      19-37        3-SOCF3          H        i-Pr                        H         NMe      5-i-C3F7
Q19      19-38        3-C2F5          H        i-Pr                        H         NMe      5-C2F5
Q19      19-39        3-I-4-Cl           H        i-Pr                        H         NMe      5-n-C3F7
Q19      19-40        3-I-4-CF3        H        i-Pr                        H         S        5-i-C3F7
Q19      19-41        3-CF3-4-Cl       H        i-Pr                        H         S        5-C2F5
Q19      19-42        3-OCF2O-4        H        i-Pr                        H         S        5-n-C3F7
Q19      19-43        3-OCF2CF2O-4    H        i-Pr                        H         S        5-i-C3F7
                            表7(Z1＝Z2＝O)
Q        No.          Xn         R1      R2        R3      Ym                mp(℃)
Q26      26-1         H          H        i-Pr        H        3-Cl-5-CF3        85
Q26      26-2         3-Cl       H        i-Pr        H        H
Q26      26-3         3-Cl       H        i-Pr        H        3-Me-5-C2F5
Q26      26-4         3-Br       H        i-Pr        H        3-Me-5-n-C3F7
Q26      26-5         3-NO2     H        i-Pr        H        3-Me-5-i-C3F7
Q26      26-6         3-I        H        i-Pr        H        5-C2F5
Q26      26-7         3-I        H        i-Pr        H        5-n-C3F7
Q26      26-8         3-I        H        i-Pr        H        5-i-C3F7
Q26      26-9         3-I        H        i-Pr        H        3-Me-5-C2F5
Q26      26-10        3-I        H        i-Pr        H        3-Me-5-n-C3F7
Q26      26-11        3-I        H        i-Pr        H        3-Me-5-i-C3F7      140
Q26      26-12        3-I        H        i-Pr        H        3-Me-4-C2F5
Q26      26-13        3-I        H        i-Pr        H        3-Me-4-n-C3F7
Q26      26-14        3-I        H        i-Pr        H        3-Me-4-i-C3F7
Q26      26-15        3-I        H        t-Bu        H        5-i-C3F7
Q26      26-16        3-I        H        t-Bu        H        5-C2F5
                                  表7(续)
Q          No.          Xn             R1      R2                        R3      Ym                   mp(℃)
Q26        26-17        3-I            H        t-Bu                        H        5-n-C3F7
Q26        26-18        3-I            H        t-Bu                        H        3-Me-5-i-C3F7
Q26        26-19        3-I            H        CH(CH3)CH2SCH3          H        3-Me-5-i-C3F7
Q26        26-20        3-I            H        CH(CH3)CH2SOCH3         H        3-Me-5-i-C3F7
Q26        26-21        3-I            H        CH(CH3)CH2SO2CH3       H        3-Me-5-i-C3F7
Q26        26-22        3-I            H        C(CH3)2CH2SCH3         H        3-Me-5-i-C3F7
Q26        26-23        3-I            H        C(CH3)2CH2SOCH3        H        3-Me-5-i-C3F7
Q26        26-24        3-I            H        C(CH3)2CH2SO2CH3      H        3-Me-5-i-C3F7
Q26        26-25        3-I            H        CH(CH3)CH2SEt             H        3-Me-5-i-C3F7
Q26        26-26        3-I            H        C(CH3)CH2SEt              H        3-Me-5-i-C3F7
Q26        26-27        3-I            H        CH(CH3)CH2CH2SCH3      H        3-Me-5-i-C3F7
Q26        26-28        3-I            H        CH(CH3)2CH2CH2SCH3    H        3-Me-5-i-C3F7
Q26        26-29        3-I            Et       Et                           H        3-Me-5-C2F5       糊状
Q26        26-30        3-I            Et       Et                           H        3-Me-5-n-C3F7     糊状
Q26        26-31        3-I            Et       Et                           H        3-Me-5-i-C3F7     159
Q26        26-32        3-I            Et       Et                           H        5-Cl                 127
Q26        26-33        3-I            Et       Et                           H        5-Br                 154
Q26        26-34        3-CF3         H        i-Pr                         H        3-Me-5-C2F5
Q26        26-35        3-Ph           H        i-Pr                         H        3-Me-5-n-C3F7
Q26        26-36        3-SOCF3       H        i-Pr                         H        3-Me-5-i-C3F7
Q26        26-37        3-C2F5      H        i-Pr                         H        3-Me-5-C2F5
Q26        26-38        3-I-4-Cl       H        i-Pr                         H        3-Me-5-n-C3F7
Q26        26-39        3-I-4-CF3     H        i-Pr                         H        3-Me-5-i-C3F7
                                表7(续)
Q        No.          Xn                 R1      R2        R3      Ym                mp(℃)
Q26      26-40        3-CF3-4-Cl        H        i-Pr        H        3-Me-5-C2F5
Q26      26-41        3-OCF2O-4         H        i-Pr        H        3-Me-5-n-C3F7
Q26      26-42        3-OCF2CF2O-4    H        i-Pr        H        3-Me-5-i-C3F7
Q26      26-43        3-I                H        i-Pr        H        3-Me-5-i-C3F7     140
Q27      27-1         H                  H        i-Pr        H        H                 139
Q27      27-2         H                  H        i-Pr        H        2-Me
Q27      27-3         H                  H        i-Pr        H        3-Me
Q27      27-4         H                  H        i-Pr        H        4-Me
Q27      27-5         H                  H        i-Pr        H        6-Me
Q27      27-6         H                  H        i-Pr        H        2-Cl
Q27      27-7         H                  H        i-Pr        H        3-Cl
Q27      27-8         H                  H        i-Pr        H        4-Cl
Q27      27-9         H                  H        i-Pr        H        6-Cl
Q27      27-10        3-Cl               H        i-Pr        H        2-CF3
Q27      27-11        3-Cl               H        i-Pr        H        3-CF3
Q27      27-12        3-Cl               H        i-Pr        H        4-CF3
Q27      27-13        3-Cl               H        i-Pr        H        6-CF3
Q27      27-14        3-Cl               H        i-Pr        H        2-NO2
Q27      27-15        3-Cl               H        i-Pr        H        3-NO2
Q27      27-16        3-Cl               H        i-Pr        H        4-NO2
Q27      27-17        3-Cl               H        i-Pr        H        6-NO2
Q27      27-18        3-Cl               H        i-Pr        H        2-Et
Q27      27-19        3-Cl               H        i-Pr        H        2-i-Pr
                            表7(续)
Q        No.          Xn          R1      R2        R3      Ym                   mp(℃)
Q27      27-20        3-Cl        H        i-Pr        H        2-t-Bu
Q27      27-21        3-Cl        H        i-Pr        H        2-SCH3
Q27      27-22        3-Cl        H        i-Pr        H        2-SOCH3
Q27      27-23        3-Cl        H        i-Pr        H        2-SO2CH3
Q27      27-24        3-Cl        H        i-Pr        H        2-SCF3
Q27      27-25        3-Cl        H        i-Pr        H        2-SCHF2
Q27      27-26        3-Cl        H        i-Pr        H        2-COCH3
Q27      27-27        3-Cl        H        i-Pr        H        2-CN
Q27      27-28        3-Cl        H        i-Pr        H        2-OCH3
Q27      27-29        3-Cl        H        i-Pr        H        2-O-(4-Br-Ph)        101
Q27      27-30        3-Cl        H        i-Pr        H        2-O-(2，4-Cl2-Ph)    97
Q27      27-31        3-Cl        H        i-Pr        H        4-S-i-Pr             193
Q27      27-32        3-Cl        H        i-Pr        H        4-S-i-Bu             183
Q27      27-33        3-Cl        H        i-Pr        H        2-OCF2CCl2F
Q27      27-34        3-Cl        H        i-Pr        H        2-OCH2CF3
Q27      27-35        3-Cl        H        i-Pr        H        2-OCH2CF2CHF2
Q27      27-36        3-Cl        H        i-Pr        H        2-CF2CF3
Q27      27-37        3-Cl        H        i-Pr        H        2-COOCH(CF3)2
Q27      27-38        3-Cl        H        i-Pr        H        2-Ph
Q27      27-39        3-Cl        H        n-Bu        H        2-Cl
Q27      27-40        3-Cl        H        i-Bu        H        2-Cl
Q27      27-41        3-Cl        H        s-Bu        H        2-Cl
Q27      27-42        3-Cl        H        t-Bu        H        2-Cl
                                表7(续)
Q        No.          Xn          R1            R2                     R3      Ym        mp(℃)
Q27      27-43        3-Cl        H              c-C3H5                H        2-Cl
Q27      27-44        3-Cl        H              c-C4H7                H        2-Cl
Q27      27-45        3-Cl        H              c-C5H9                H        2-Cl
Q27      27-46        3-Cl        H              c-C6H11               H        2-Cl
Q27      27-47        3-Cl        H              CH2CH＝CH2            H        2-Cl
Q27      27-48        3-Cl        H              CH2C≡CH               H        2-Cl
Q27      27-49        3-Cl        H              CH2Ph                  H        2-Cl
Q27      27-50        3-Cl        H              C(CH3)2C≡CH          H        2-Cl
Q27      27-51        3-Cl        H              C(CH3)2C≡CPh         H        2-Cl
Q27      27-52        3-Cl        H              CH2CH2SCH3           H        2-Cl
Q27      27-53        3-Cl        H              CH2CH2SPh             H        2-Cl
Q27      27-54        3-Cl        H              CH2CH2SO2Ph          H        2-Cl
Q27      27-55        3-Cl        H              CH2CH2SO2CH3        H        2-Cl
Q27      27-56        3-Cl        H              CH2CH2CO2CH3        H        2-Cl
Q27      27-57        3-Cl        H              CH2CH2CONHCH3        H        2-Cl
Q27      27-58        3-Cl        Et             Et                       H        2-Cl
Q27      27-59        3-Cl        n-Pr           n-Pr                     H        2-Cl
Q27      27-60        3-Cl        i-Pr           i-Pr                     H        2-Cl
Q27      27-61        3-Cl        i-Pr           Me                       H        2-Cl
Q27      27-62        3-Cl        i-Bu           Me                       H        2-Cl
Q27      27-63        3-Cl        CH2CH＝CH2  CH2CH＝CH2             H        2-Cl
Q27      27-64        3-Cl        Et             Et                       Me       2-Cl
Q27      27-65        3-Cl        n-Pr           i-Pr                     Me       2-Cl
                            表7(续)
Q        No.        Xn          R1               R2          R3      Ym        mp(℃)
Q27      27-66      3-Cl        i-Pr              i-Pr          Me       2-Cl
Q27      27-67      3-Cl        Et                Et            Ac       2-Cl
Q27      27-68      3-Cl        n-Pr              i-Pr          Ac       2-Cl
Q27      27-69      3-Cl        i-Pr              i-Pr          Ac       2-Cl
Q27      27-70      3-Cl            -(CH2)4-                 H        2-Cl
Q27      27-71      3-Cl            -(CH2)2O(CH2)2-        H        2-Cl
Q27      27-72      3-Cl        i-Pr              SO2CH3     H        2-Cl
Q27      27-73      3-Cl        i-Pr              CN            H        2-Cl
Q27      27-74      3-Cl        i-Pr              CO2CH3     H        2-Cl
Q27      27-75      3-Cl        i-Pr              COCH3        H        2-Cl
Q27      27-76      3-Cl        i-Pr              COPh          H        2-Cl
Q27      27-77      3-Cl        i-Pr              NHCOCH3      H        2-Cl
Q27      27-78      3-Cl        H                 i-Pr          H        2，4-Me2
Q27      27-79      3-Cl        H                 i-Pr          H        2，4-Cl2
Q27      27-80      3-Cl        H                 i-Pr          H        4，6-Me2
Q27      27-81      3-Cl        H                 i-Pr          H        4-Me-2-Cl       211
Q27      27-82      3-Cl        H                 i-Pr          H        4-Me-2-F
Q27      27-83      3-Cl        H                 i-Pr          H        4-Me-2-Br
Q27      27-84      3-Cl        H                 i-Pr          H        4-Me-2-I
Q27      27-85      3-Cl        H                 i-Pr          H        4-Me-2-OCHF2
Q27      27-86      3-Cl        H                 i-Pr          H        4-Me-2-OCF3
Q27      27-87      3-Cl        H                 i-Pr          H        4-Me-2-NO2
Q27      27-88      3-Cl        H                 i-Pr          H        4-Me-2-NMe2
                            表7(续)
Q        No.           Xn          R1      R2        R3      Ym                 mp(℃)
Q27      27-89         3-Cl        H        i-Pr        H        4-Me-2-C≡CH
Q27      27-90         3-Cl        H        i-Pr        H        4-Me-2-C≡C-t-Bu
Q27      27-91         3-Cl        H        i-Pr        H        4-Me-2-C≡CPh
Q27      27-92         3-Cl        H        i-Pr        H        4-Me-2-CF2CF3
Q27      27-93         3-Cl        H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-94         3-Cl        H        i-Pr        H        4-Me-2-n-C3F7
Q27      27-95         3-Cl        H        i-Pr        H        4-Me-2-OCH2OCH3
Q27      27-96         3-Cl        H        i-Pr        H        4-Me-2-OCF2CHF2
Q27      27-97         3-Cl        H        i-Pr        H        4-Me-2-OPh
Q27      27-98         3-Cl        H        i-Pr        H        4-Me-2-O-(4-Br-Ph)    79
Q27      27-99         3-Cl        H        i-Pr        H        4-Me-2-OSO2Ph
Q27      27-100        3-Cl        H        i-Pr        H        4-Me-2-OCH2CO2CH3
Q27      27-101        3-Cl        H        i-Pr        H        4-Me-2-CO2CH3
Q27      27-102        3-Cl        H        i-Pr        H        4-Me-2-S-i-Pr
Q27      27-103        3-Cl        H        i-Pr        H        4-Me-2-SCHF2
Q27      27-104        3-Cl        H        i-Pr        H        4-Me-2-SOCHF2
Q27      27-105        3-Cl        H        i-Pr        H        4-Me-2-SO2CHF2
Q27      27-106        3-Cl        H        i-Pr        H        4-Cl-2-CF3
Q27      27-107        3-Cl        H        i-Pr        H        4-Cl-2-OCF3
Q27      27-108        3-Cl        H        i-Pr        H        4-Cl-2-i-C3F7
Q27      27-109        3-Cl        H        i-Pr        H        4-Cl-2-C2F5
Q27      27-110        3-Cl        H        i-Pr        H        4-Cl-2-OCHF2
Q27      27-111        3-Cl        H        i-Pr        H        4-Cl-2-OSO2Ph
                                 表7(续)
Q        No.           Xn          R1      R2        R3      Ym                    mp(℃)
Q27      27-112        3-Cl        H        i-Pr        H        4-OCH3-2-Ph
Q27      27-113        3-Cl        H        i-Pr        H        4-CF3-2-Cl
Q27      27-114        3-Cl        H        i-Pr        H        4-Me-3-CF3
Q27      27-115        3-Cl        H        i-Pr        H        4-Me-3-Cl
Q27      27-116        3-Cl        H        i-Pr        H        4-Me-3-OCF3
Q27      27-117        3-Cl        H        i-Pr        H        4-Me-3-CF2CF3
Q27      27-118        3-Cl        H        i-Pr        H        4-Me-3-n-C3F7
Q27      27-119        3-Cl        H        i-Pr        H        4-Me-3-i-C3F7
Q27      27-120        3-Cl        H        i-Pr        H        3，4-Me2-2-Cl
Q27      27-121        3-Cl        H        i-Pr        H        3，4-Me2-2-OMe
Q27      27-122        3-Cl        H        i-Pr        H        3，4-Me2-2-SMe
Q27      27-123        3-Cl        H        i-Pr        H        4-Me-2，3-Cl2
Q27      27-124        6-Cl        H        i-Pr        H        2-O-(4-Br-Ph)          170
Q27      27-125        6-Cl        H        i-Pr        H        2-O-(2，4-Cl2-Ph)     189
Q27      27-126        6-Cl        H        i-Pr        H        2-S-i-Pr               120
Q27      27-127        6-Cl        H        i-Pr        H        2-S-i-Bu               187
Q27      27-128        6-Cl        H        i-Pr        H        4-Me-2-Cl              230
Q27      27-129        3-I         Et       Et          H        6-Cl-2-n-C3F7       122
Q27      27-130        3-I         Et       Et          H        2-Cl                   203
Q27      27-131        3-I         Et       Et          H        2-n-C3F7            200
Q27      27-132        3-I         Et       Et          H        2-O-(4-Br-Ph)          247
Q27      27-133        3-I         H        i-Pr        H        2-Cl                   215
Q27      27-134        3-I         H        i-Pr        H        2-C2F5              无定形固体
                            表7(续)
Q        No.           Xn         R1      R2                       R3      Ym                    mp(℃)
Q27      27-135        3-I        H        i-Pr                       H        2-n-C3F7           200
Q27      27-136        3-I        H        i-Pr                       H        2-i-C3R7           270
Q27      27-137        3-I        H        i-Pr                       H        4-Me-2-i-C3F7      257
Q27      27-138        3-I        H        i-Pr                       H        6-Me-2-i-C3F7      234
Q27      27-139        3-I        H        t-Bu                       H        2-i-C3F7           275
Q27      27-140        3-I        H        t-Bu                       H        2-C2F5             260
Q27      27-141        3-I        H        t-Bu                       H        2-n-C3F7           245
Q27      27-142        3-I        H        t-Bu                       H        4-Me-2-i-C3F7      250
Q27      27-143        3-I        H        t-Bu                       H        6-Me-2-i-C3F7      246
Q27      27-144        3-I        H        CH(CH3)CH2SCH3         H        4-Me-2-i-C3F7      225
Q27      27-145        3-I        H        CH(CH3)CH2SCH3         H        6-Me-2-i-C3F7      229
Q27      27-146        3-I        H        CH(CH3)CH2SOCH3        H        4-Me-2-i-C3F7
Q27      27-147        3-I        H        CH(CH3)CH2SOCH3        H        6-Me-2-i-C3F7
Q27      27-148        3-I        H        CH(CH3)CH2SO2CH3      H        4-Me-2-i-C3F7
Q27      27-149        3-I        H        CH(CH3)CH2SO2CH3      H        6-Me-2-i-C3F7
Q27      27-150        3-I        H        C(CH3)2CH2SCH3        H        4-Me-2-i-C3F7      173
Q27      27-151        3-I        H        C(CH3)2CH2SCH3        H        6-Me-2-i-C3F7      213
Q27      27-152        3-I        H        C(CH3)2CH2SOCH3       H        4-Me-2-i-C3F7
Q27      27-153        3-I        H        C(CH3)2CH2SOCH3       H        6-Me-2-i-C3F7      无定形
Q27      27-154        3-I        H        C(CH3)2CH2SO2CH3    H        4-Me-2-i-C3F7
Q27      27-155        3-I        H        C(CH3)2CH2SO2CH3    H        6-Me-2-i-C3F7
Q27      27-156        3-I        H        i-Pr                       H        4-Me-2-i-C3F7
Q27      27-157        3-I        H        t-Bu                       H        6-Me-2-i-C3F7
                            表7(续)
Q        No.           Xn          R1      R2                    R3      Ym                  mp(℃)
Q27      27-158        3-F         H        C(CH3)2CH2SCH3    H        4-Me-2-i-C3F7
Q27      27-159        3-F         H        C(CH3)2CH2SCH3    H        6-Me-2-i-C3F7
Q27      27-160        3-Br        H        i-Pr                   H        4-Me-2-i-C3F7
Q27      27-161        3-Br        H        t-Bu                   H        6-Me-2-i-C3F7
Q27      27-162        3-Br        H        CH(CH3)CH2SCH3     H        4-Me-2-i-C3F7
Q27      27-163        3-Br        H        C(CH3)2CH2SCH3    H        6-Me-2-i-C3F7
Q27      27-164        3-NO2      H        i-Pr                   H        H                    209
Q27      27-165        3-NO2      H        i-Pr                   H        4-Me-2-CF2CF3
Q27      27-166        3-NO2      H        i-Pr                   H        4-Me-2-n-C3F7
Q27      27-167        3-NO2      H        i-Pr                   H        4-Me-2-i-C3F7
Q27      27-168        3-NO2      H        i-Pr                   H        6-Me-2-CF2CF3
Q27      27-169        3-NO2      H        i-Pr                   H        6-Me-2-n-C3F7
Q27      27-170        3-NO2      H        i-Pr                   H        6-Me-2-i-C3F7
Q27      27-171        3-NO2      H        i-Pr                   H        4-Me-2-Cl
Q27      27-172        3-CN        Et       Et                     H        4-Me-2-CF2CF3
Q27      27-173        3-CN        Et       Et                     H        4-Me-2-n-C3F7
Q27      27-174        3-CN        Et       Et                     H        4-Me-2-i-C3F7
Q27      27-175        3-CN        Et       Et                     H        6-Me-2-CF2CF3
Q27      27-176        3-CN        Et       Et                     H        6-Me-2-n-C3F7
Q27      27-177        3-CN        Et       Et                     H        6-Me-2-i-C3F7
Q27      27-178        3-CN        Et       Et                     H        4-Me-2-Cl
Q27      27-179        3-CF3      H        i-Pr                   H        4-Me-2-CF2CF3
Q27      27-180        3-CF3      H        i-Pr                   H        6-Me-2-n-C3F7
                                表7(续)
Q        No.         Xn               R1      R2        R3      Ym               mp(℃)
Q27      27-181      3-OCH3          H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-182      3-OCH3          H        i-Pr        H        6-Me-2-CF2CF3
Q27      27-183      3-OCH3          H        i-Pr        H        4-Me-2-n-C3F7
Q27      27-184      3-OCH3          H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-185      3-SCH3          H        i-Pr        H        4-Me-2-CF2CF3
Q27      27-186      3-SCH3          H        i-Pr        H        6-Me-2-n-C3F7
Q27      27-187      3-S-i-Pr         H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-188      3-S-i-Pr         H        i-Pr        H        6-Me-2-CF2CF3
Q27      27-189      3-SOCH3         H        i-Pr        H        4-Me-2-n-C3F7
Q27      27-190      3-SOCH3         H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-191      3-SO2CH3       H        i-Pr        H        4-Me-2-CF2CF3
Q27      27-192      3-SO2CH3       H        i-Pr        H        6-Me-2-n-C3F7
Q27      27-193      3-SCH2CF3      H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-194      3-SCF3          H        i-Pr        H        4-Me-2-CF2CF3
Q27      27-195      3-SOCF3         H        i-Pr        H        4-Me-2-n-C3F7
Q27      27-196      3-SO2CF3       H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-197      3-SPh            H        i-Pr        H        6-Me-2-CF2CF3
Q27      27-198      3-SOPh           H        i-Pr        H        6-Me-2-n-C3F7
Q27      27-199      3-SO2Ph         H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-200      3-OPh            H        i-Pr        H        4-Me-2-CF2CF3
Q27      27-201      3-Ph             H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-202      3-C≡CH          H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-203      3-C≡C-t-Bu      H        i-Pr        H        4-Me-2-i-C3F7
                            表7(续)
Q        No.           Xn                    R1      R2        R3      Ym              mp(℃)
Q27      27-204        3-C≡CPh              H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-205        3-C2F5              H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-206        3-CO2CH3            H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-207        3-CONHCH3            H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-208        3-COCH3              H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-209        3-CCH3(＝NOCH3)     H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-210        3，4-Cl2             H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-211        3，6-Cl2             H        i-Pr        H        4-Me-2-n-C3F7
Q27      27-212        3，5-Cl2             H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-213        3，5-Cl2             H        i-Pr        H        6-Me-2-CF2CF3
Q27      27-214        4，5-Cl2             H        i-Pr        H        4-Me-2-n-C3F7
Q27      27-215        4，5-Cl2             H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-216        3-I-4-Cl              H        i-Pr        H        4-Me-2-CF2CF3
Q27      27-217        3-I-4-F               H        i-Pr        H        4-Me-2-n-C3F7
Q27      27-218        3-I-4CF3             H        i-Pr        H        4-Me-2-i-C3F7
Q27      27-219        3-I-4-OCH3           H        i-Pr        H        4-Me-2-CF2CF3
Q27      27-220        3-CF3-4-Cl           H        i-Pr        H        4-Me-2-n-C3F7
Q27      27-221        3-CF3-4-OCH3        H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-222        3-OCH2O-4            H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-223        3-OCF2O-4            H        i-Pr        H        6-Me-2-CF2CF3
Q27      27-224        3-OCH2CH2O-4        H        i-Pr        H        6-Me-2-n-C3F7
Q27      27-225        3-OCF2CF2O-4        H        i-Pr        H        6-Me-2-i-C3F7
Q27      27-226        3-CH＝CH-CH＝CH-4     H        i-Pr        H        6-Me-2-i-C3F7
                                    表7(续)
Q        No.           Xn         R1      R2                R3      Ym                       mp(℃)
Q27      27-227        3-I        H        i-Pr                H        4-Me-3-CF2CF3
Q27      27-228        3-I        H        i-Pr                H        4-Me-3-i-C3F7
Q27      27-229        3-I        H        i-Pr                H        4-Me-3-n-C3F7
Q27      27-230        3-I        H        i-Pr                H        6-Cl-2-i-C3F7         188
Q27      27-231        3-I        Et       Et                  H        6-Cl-2-i-C3F7         164
Q27      27-232        3-I        H        CH(Me)CH2SMe       H        6-Cl-2-i-C3F7         177
Q27      27-233        3-I        H        C(Me)2CH2SMe      H        2-i-C3F7              229
Q27      27-234        3-I        H        C(Me)2CH2SMe      H        6-Cl-2-i-C3F7         175
Q27      27-235        3-I        H        C(Me)2CH2SOMe     H        6-Cl-2-i-C3F7         糊状
Q27      27-236        3-I        H        C(Me)2CH2SO2Me   H        6-Cl-2-i-C3F7         无定形
Q27      27-237        3-I        H        C(Me)2CH2SMe      H        6-i-C3F7              183
Q27      27-238        3-I        H        C(Me)2CH2SOMe     H        6-i-C3F7              无定形
Q27      27-239        3-I        H        C(Me)2CH2SO2Me   H        6-i-C3F7              无定形
Q27      27-240        3-I        H        C(Me)2CH2SMe      H        4，6-Cl2-2-i-C3F7    120
Q27      27-241        3-I        H        CH(Me)CH2SMe       H        6-MeO-2-i-C3F7        134
Q27      27-242        3-I        H        i-Pr                 H        6-MeO-2-i-C3F7        158
Q27      27-243        3-I        H        C(Me)2CH2SMe      H        6-MeO-2-i-C3F7        134
Q27      27-244        3-I        H        C(Me)2CH2SOMe     H        6-MeO-2-i-C3F7        无定形
Q27      27-245        3-I        H        C(Me)2CH2SMe      H        6-MeS-2-i-C3F7        179
Q27      27-246        3-I        H        i-Pr                 H        6-MeS-2-i-C3F7        219
Q27      27-247        3-I        H        i-Pr                 H        6-MeSO-2-i-C3F7       无定形
Q27      27-248        3-I        H        C(Me)2CH2SMe      H        2-OCHF2                 198
Q27      27-249        3-I        H        C(Me)2CH2SO2Me   H        2-OCHF2                 207
                            表7(续)
Q        No.           Xn         R1      R2                 R3    Ym                   mp(℃)
Q27      27-250        3-I        H        i-Pr                 H      2-OCHF2             205
Q27      27-251        3-I        H        C(Me)2CH2SMe      H      2-SCHF2             174
Q27      27-252        3-I        H        i-Pr                 H      2-SCHF2             226
Q27      27-253        3-I        H        i-Pr                 H      2-SO2CHF2          230
Q27      27-254        3-I        H        i-Pr                 H      6-Me-2-OCHF2        252
Q27      27-255        3-I        H        C(Me)2CH2SMe      H      6-Me-2-OCHF           124
Q27      27-256        3-I        H        C(Me)2CH2SOMe     H      6-Me-2-OCHF2        185
Q27      27-257        3-I        H        C(Me)2CH2SO2Me   H      6-Me-2-OCHF2        102
Q27      27-258        3-I        H        i-Pr                 H      6-Me-2-SCHF2        226
Q27      27-259        3-I        H        C(Me)2CH2SMe      H      6-Me-2-SCHF2        198
Q27      27-260        3-I        H        i-Pr                 H      6-Me-2-OCH(CF3)2   266
Q27      27-261        3-I        H        C(Me)2CH2SMe      H      6-Me-2-OCH(CF3)2   223
Q27      27-262        3-I        H        i-Pr                 H      6-Cl-2-OCH(CF3)2   216
Q27      27-263        3-I        H        C(Me)2CH2SMe      H      6-Cl-2-OCH(CF3)2   100
Q27      27-264        3-I        H        C(Me)2CH2SOMe     H      6-Me-2-OCH(CF3)2   168
Q27      27-265        3-I        H        C(Me)2CH2SO2Me   H      6-Me-2-OCH(CF3)2   134
Q27      27-266        3-I        H        C(Me)2CH2SOMe     H      6-Cl-2-OCH(CF3)2
Q27      27-267        3-I        H        C(Me)2CH2SO2Me   H      6-Cl-2-OCH(CF3)2   121
Q27      27-268        3-I        H        C(Me)2CH2SMe      H      6-OMe-2-OCH(CF3)2  159
Q27      27-269        3-I        H        C(Me)2CH2SMe      H      6-F-2-OCH(CF3)2
Q27      27-270        3-I        H        i-Pr                 H      OCH(CF3)2          240
Q27      27-271        3-I        H        t-Bu                 H      OCH(CF3)2
Q27      27-272        3-I        H        CH(Me)CH2SMe        H      OCH(CF3)2
                                表7(续)
Q        No.           Xn         R1      R2                 R3    Ym                      mp(℃)
Q27      27-273        3-I        H        C(Me)2CH2SMe      H      OCH(CF3)2             237
Q27      27-274        3-I        H        i-Pr                 H      2-Me-6-OCH(CF3)2      232
Q27      27-275        3-I        H        C(Me)2CH2SMe      H      2-Me-6-OCH(CF3)2      171
Q27      27-276        3-Cl       H        i-Pr                 H      4-Me-2-OCH(CF3)2      226
Q27      27-277        3-I        H        i-Pr                 H      4-Me-2-OCH(CF3)2      248
Q27      27-278        3-I        H        C(Me)2CH2SMe      H      4-Me-2-OCH(CF3)2      200
Q27      27-279        3-I        H        C(Me)2CH2SOMe     H      4-Me-2-OCH(CF3)2      118
Q27      27-280        3-I        H        C(Me)2CH2SO2Me   H      4-Me-2-OCH(CF3)2      112
Q27      27-281        3-I        H        CH(Me)CH2SMe       H      6-Me-2-OCH(CF3)2
Q27      27-282        3-I        H        CH(Me)CH2SEt       H      6-Me-2-OCH(CF3)2       256
Q27      27-283        H          H        i-Pr                 H      6-Me-2-OCH(CF3)2      235
Q27      27-284        H          H        t-Bu                 H      6-Me-2-OCH(CF3)2      255
Q27      27-285        H          H        CH(Me)CH2SMe       H      6-Me-2-OCH(CF3)2
Q27      27-286        H          H        CH(Me)CH2SOMe      H      6-Me-2-OCH(CF3)2
Q27      27-287        H          H        CH(Me)CH2SO2Me    H      6-Me-2-OCH(CF3)2
Q27      27-288        H          H        C(Me)2CH2SMe      H      6-Me-2-OCH(CF3)2
Q27      27-289        H          H        C(Me)2CH2SOMe     H      6-Me-2-OCH(CF3)2      108
Q27      27-290        H          H        C(Me)2CH2SO2Me   H      6-Me-2-OCH(CF3)2
Q27      27-291        3-F        H        i-Pr                 H      6-Me-2-OCH(CF3)2
Q27      27-292        3-F        H        t-Bu                 H      6-Me-2-OCH(CF3)2
Q27      27-293        3-F        H        CH(Me)CH2SMe        H      6-Me-2-OCH(CF3)2
Q27      27-294        3-F        H        C(Me)2CH2SMe      H      6-Me-2-OCH(CF3)2
Q27      27-295        3-F        H        C(Me)2CH2SOMe     H      6-Me-2-OCH(CF3)2
                                表7(续)
Q        No.         Xn        R1      R2                  R3    Ym                    mp(℃)
Q27      27-296      3-F       H        C(Me)2CH2SO2Me    H      6-Me-2-OCH(CF3)2
Q27      27-297      3-Cl      H        i-Pr                  H      6-Me-2-OCH(CF3)2      257
Q27      27-298      3-Cl      H        t-Bu                  H      6-Me-2-OCH(CF3)2      255
Q27      27-299      3-Cl      Et       Et                    H      6-Me-2-OCH(CF3)2
Q27      27-300      3-Cl      H        CH(Me)CH2SMe        H      6-Me-2-OCH(CF3)2
Q27      27-301      3-Cl      H        CH(Me)CH2SOMe       H      6-Me-2-OCH(CF3)2
Q27      27-302      3-Cl      H        CH(Me)CH2SO2Me     H      6-Me-2-OCH(CF3)2
Q27      27-303      3-Cl      H        CH(Me)CH2SEt        H      6-Me-2-OCH(CF3)2
Q27      27-304      3-Cl      H        CH(Me)CH2SO2Et     H      6-Me-2-OCH(CF3)2
Q27      27-305      3-Cl      H        C(Me)2CH2SMe       H      6-Me-2-OCH(CF3)2      236
Q27      27-306      3-Cl      H        C(Me)2CH2SOMe      H      6-Me-2-OCH(CF3)2      115
Q27      27-307      3-Cl      H        C(Me)2CH2SO2Me    H      6-Me-2-OCH(CF3)2      221
Q27      27-308      3-Br      H        i-Pr                  H      6-Me-2-OCH(CF3)2      252
Q27      27-309      3-Br      H        t-Bu                  H      6-Me-2-OCH(CF3)2      255
Q27      27-310      3-Br      Et       Et                    H      6-Me-2-OCH(CF3)2
Q27      27-311      3-Br      H        CH(Me)CH2SMe         H      6-Me-2-OCH(CF3)2
Q27      27-312      3-Br      H        CH(Me)CH2SOMe        H      6-Me-2-OCH(CF3)2
Q27      27-313      3-Br      H        CH(Me)CH2SO2Me      H      6-Me-2-OCH(CF3)2
Q27      27-314      3-Br      H        CH(Me)CH2SEt         H      6-Me-2-OCH(CF3)2
Q27      27-315      3-Br      H        CH(Me)CH2SO2Et      H      6-Me-2-OCH(CF3)2
Q27      27-316      3-Br      H        C(Me)2CH2SMe        H      6-Me-2-OCH(CF3)2      228
Q27      27-317      3-Br      H        C(Me)2CH2SOMe       H      6-Me-2-OCH(CF3)2      115
Q27      27-318      3-Br      H        C(Me)2CH2SO2Me     H      6-Me-2-OCH(CF3)2      225
                            表7(续)
Q        No.         Xn             R1      R2               R3    Ym                      mp(℃)
Q27      27-319      3-I            H        Me                 H      6-Me-2-OCH(CF3)2
Q27      27-320      3-I            H        Et                 H      6-Me-2-OCH(CF3)2
Q27      27-321      3-I            H        n-Pr               H      6-Me-2-OCH(CF3)2
Q27      27-322      3-I            H        c-C3H5          H      6-Me-2-OCH(CF3)2
Q27      27-323      3-I            H        n-Bu               H      6-Me-2-OCH(CF3)2      261
Q27      27-324      3-I            H        s-Bu               H      6-Me-2-OCH(CF3)2      274
Q27      27-325      3-I            H        t-Bu               H      6-Me-2-OCH(CF3)2      241
Q27      27-326      3-I            H        i-Bu               H      6-Me-2-OCH(CF3)2      264
Q27      27-327      3-I            Et       Et                 H      6-Me-2-OCH(CF3)2      165
Q27      27-328      3-I            Me       i-Pr               H      6-Me-2-OCH(CF3)2
Q27      27-329      3-Cl-4-F       H        i-Pr               H      6-Me-2-OCH(CF3)2
Q27      27-330      3-Cl-4-F       H        CH(Me)CH2SMe      H      6-Me-2-OCH(CF3)2
Q27      27-331      3-Cl-4-F       H        C(Me)2CH2SMe     H      6-Me-2-OCH(CF3)2
Q27      27-332      3，4-Cl2      H        i-Pr               H      6-Me-2-OCH(CF3)2      267
Q27      27-333      3，4-Cl2      H        t-Bu               H      6-Me-2-OCH(CF3)2
Q27      27-334      3，4-Cl2      H        CH(Me)CH2SMe      H      6-Me-2-OCH(CF3)2      210
Q27      27-335      3，4-Cl2      H        CH(Me)CH2SOMe     H      6-Me-2-OCH(CF3)2
Q27      27-336      3，4-Cl2      H        CH(Me)CH2SO2Me   H      6-Me-2-OCH(CF3)2      126
Q27      27-337      3，4-Cl2      H        CH(Me)CH2SEt      H      6-Me-2-OCH(CF3)2      205
Q27      27-338      3，4-Cl2      H        CH(Me)CH2SOEt     H      6-Me-2-OCH(CF3)2      119
Q27      27-339      3，4-Cl2      H        CH(Me)CH2SO2Et   H      6-Me-2-OCH(CF3)2      111
Q27      27-340      3，4-Cl2      H        C(Me)2CH2SMe     H      6-Me-2-OCH(CF3)2
Q27      27-341      3-Br-4-Cl      H        C(Me)2CH2SMe     H      6-Me-2-OCH(CF3)2
                            表7(续)
Q        No.         Xn           R1      R2                  R3      Ym                       mp(℃)
Q27      27-342      3，4-Br2    H        C(Me)2CH2SMe       H        6-Me-2-OCH(CF3)2
Q27      27-343      3-I-4-F      H        C(Me)2CH2SMe       H        6-Me-2-OCH(CF3)2
Q27      27-344      3-I-4-Cl     H        C(Me)2CH2SMe       H        6-Me-2-OCH(CF3)2
Q27      27-345      3-I-4-Br     H        C(Me)2CH2SMe       H        6-Me-2-OCH(CF3)2
Q27      27-346      3，4-I2     H        C(Me)2CH2SMe       H        6-Me-2-OCH(CF3)2
Q27      27-347      3-NO2       H        i-Pr                  H        6-Me-2-OCH(CF3)2      207
Q27      27-348      3-NO2       H        t-Bu                  H        6-Me-2-OCH(CF3)2
Q27      27-349      3-NO2       Et       Et                    H        6-Me-2-OCH(CF3)2
Q27      27-350      3-NO2       H        CH(Me)CH2SMe        H        6-Me-2-OCH(CF3)2
Q27      27-351      3-NO2       H        CH(Me)CH2SO2Me     H        6-Me-2-OCH(CF3)2
Q27      27-352      3-NO2       H        C(Me)2CH2SMe       H        6-Me-2-OCH(CF3)2      244
Q27      27-353      3-NO2       H        C(Me)2CH2SO2Me    H        6-Me-2-OCH(CF3)2      230
Q27      27-354      3-CF3       H        i-Pr                  H        6-Me-2-OCH(CF3)2      211
Q27      27-355      3-CF3       H        t-Bu                  H        6-Me-2-OCH(CF3)2      246
Q27      27-356      3-CF3       Et       Et                    H        6-Me-2-OCH(CF3)2
Q27      27-357      3-CF3       H        CH(Me)CH2SMe         H        6-Me-2-OCH(CF3)2
Q27      27-358      3-CF3       H        CH(Me)CH2SO2Me     H        6-Me-2-OCH(CF3)2
Q27      27-359      3-CF3       H        C(Me)2CH2SMe       H        6-Me-2-OCH(CF3)2      226
Q27      27-360      3-CF3       H        C(Me)2CH2SOMe      H        6-Me-2-OCH(CF3)2      112
Q27      27-361      3-CF3       H        C(Me)2CH2SO2Me    H        6-Me-2-OCH(CF3)2
Q27      27-362      3-OCF3      H        i-Pr                  H        6-Me-2-OCH(CF3)2
Q27      27-363      3-OCF3      H        CH(Me)CH2SMe         H        6-Me-2-OCH(CF3)2
Q27      27-364      3-OCF3      H        C(Me)2CH2SMe        H        6-Me-2-OCH(CF3)2
                                表7(续)
Q        No.         Xn               R1      R2                  R3       Ym                      mp(℃)
Q27      27-365      3-SCF3          H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-366      3-SCF3          H        CH(Me)CH2SMe        H          6-Me-2-OCH(CF3)2
Q27      27-367      3-SCF3          H        C(Me)2CH2SMe      H          6-Me-2-OCH(CF3)2
Q27      27-368      3-SOCF3         H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-369      3-SO2CF3        H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-370      3-Me             H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-371      3-Et             H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-372      5-t-Bu           H        i-Pr                 H          6-Me-2-OCH(CF3)2     280
Q27      27-373      3-C≡CH          H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-374      3-C≡CCF3       H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-375      3-C≡C-t-Bu      H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-376      3-C≡C-SiMe3    H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-377      3-C≡C-Ph        H        i-Pr                 H          6-Me-2-OCH(CF3)2
Q27      27-378      3-I              H        i-Pr                 H          6-Me-2-OCF2CHF2      217
Q27      27-379      3-I              H        t-Bu                 H          6-Me-2-OCF2CHF2
Q27      27-380      3-I              Et       Et                   H          6-Me-2-OCF2CHF2
Q27      27-381      3-I              H        CH(Me)CH2SMe        H          6-Me-2-OCF2CHF2
Q27      27-382      3-I              H        CH(Me)CH2SOMe       H          6-Me-2-OCF2CHF2
Q27      27-383      3-I              H        CH(Me)CH2SO2Me     H          6-Me-2-OCF2CHF2
Q27      27-384      3-I              H        C(Me)2CH2SMe       H          6-Me-2-OCF2CHF2      99
Q27      27-385      3-I              H        C(Me)2CH2SOMe      H          6-Me-2-OCF2CHF2
Q27      27-386      3-I              H        C(Me)2CH2SO2Me    H          6-Me-2-OCF2CHF2
Q27      27-387      3-I              H        i-Pr                  H          6-Cl-2-OCF2CHF2      200
                               表7(续)
Q        No.           Xn         R1      R2                   R3    Ym                           mp(℃)
Q27      27-388        3-I        H        C(Me)2CH2SMe        H      6-Cl-2-OCF2CHF2            142
Q27      27-389        3-I        H        C(Me)2CH2SOMe       H      6-Cl-2-OCF2CHF2
Q27      27-390        3-I        H        C(Me)2CH2SO2Me     H      6-Cl-2-OCF2CHF2
Q27      27-391        3-I        H        i-Pr                   H      6-Me-2-OCF2CHFCF3          205
Q27      27-392        3-I        H        CH(Me)CH2SMe          H      6-Me-2-OCF2CHFCF3
Q27      27-393        3-I        H        C(Me)2CH2SMe        H      6-Me-2-OCF2CHFCF3          158
Q27      27-394        3-I        H        i-Pr                   H      6-Me-2-OCF2CHFCF3
Q27      27-395        3-I        H        CH(Me)CH2SMe          H      6-Me-2-OCF2CHFCF3
Q27      27-396        3-I        H        C(Me)2CH2SMe        H      6-Me-2-OCF2CHFCF3          126
Q27      27-397        3-I        H        i-Pr                   H      6-Me-2-OCF2CHFOC3F7-n    194
Q27      27-398        3-I        H        t-Bu                   H      6-Me-2-OCF2CHFOC3F7-n
Q27      27-399        3-I        H        CH(Me)CH2SMe         H      6-Me-2-OCF2CHFOC3F7-n
Q27      27-400        3-I        H        CH(Me)CH2SOMe        H      6-Me-2-OCF2CHFOC3F7-n
Q27      27-401        3-I        H        CH(Me)CH2SO2Me      H      6-Me-2-OCF2CHFOC3F7-n
Q27      27-402        3-I        H        C(Me)2CH2SMe        H      6-Me-2-OCF2CHFOC3F7-n     91
Q27      27-403        3-I        H        C(Me)2CH2SOMe       H      6-Me-2-OCF2CHFOC3F7-n     81
Q27      27-404        3-I        H        C(Me)2CH2SO2Me     H      6-Me-2-OCF2CHFOC3F7-n    157
Q27      27-405        3-I        H        i-Pr                   H      6-Cl-2-OCF2CHFOC3F7-n    205
Q27      27-406        3-I        H        t-Bu                   H      6-Cl-2-OCF2CHFOC3F7-n
Q27      27-407        3-I        H        CH(Me)CH2SMe         H      6-Cl-2-OCF2CHFOC3F7-n     106
Q27      27-408        3-I        H        CH(Me)CH2SOMe        H      6-Cl-2-OCF2CHFOC3F7-n
Q27      27-409        3-I        H        CH(Me)CH2SO2Me      H      6-Cl-2-OCF2CHFOC3F7-n
Q27      27-410        3-I        H        C(Me)2CH2SMe        H      6-Cl-2-OCF2CHFOC3F7-n
                                表7(续)
Q        No.           Xn         R1      R2                  R3      Ym                        mp(℃)
Q27      27-411        3-I        H        C(Me)2CH2SOMe      H        6-Cl-2-OCF2CHFOC3F7-n
Q27      27-412        3-I        H        C(Me)2CH2SO2Me    H        6-Cl-2-OCF2CHFOC3F7-n
Q27      27-413        3-I        H        i-Pr                  H        6-Me-2-OCH2C2F5           259
Q27      27-414        3-I        H        CH(Me)CH2SMe         H        6-Me-2-OCH2C2F5           208
Q27      27-415        3-I        H        C(Me)2CH2SMe       H        6-Me-2-OCH2C2F5
Q27      27-416        3-I        H        i-Pr                  H        6-Me-2-OCH2-n-C3F7
Q27      27-417        3-I        H        CH(Me)CH2SMe         H        6-Me-2-OCH2-n-C3F7
Q27      27-418        3-I        H        C(Me)2CH2SMe       H        6-Me-2-OCH2-n-C3F7
Q27      27-419        3-I        H        i-Pr                  H        6-Me-2-O-(2，4-Cl2-Ph)
Q27      27-420        3-I        H        C(Me)2CH2SMe       H        6-Me-2-O-(2，4-Cl2-Ph)
Q27      27-421        3-I        H        i-Pr                  H        6-Me-2-O-(2-Cl-4-CF3-Ph)
Q27      27-422        3-I        H        C(Me)2CH2SMe       H        6-Me-2-O-(2-Cl-4-CF3-Ph)
Q27      27-423        3-I        H        i-Pr                  H        6-Me-2-SCF3
Q27      27-424        3-I        H        CH(Me)CH2SMe         H        6-Me-2-SCF3
Q27      27-425        3-I        H        C(Me)2CH2SMe       H        6-Me-2-SCF3
Q27      27-426        3-I        H        C(Me)2CH2SOMe      H        6-Me-2-SCF3
Q27      27-427        3-I        H        C(Me)2CH2SO2Me    H        6-Me-2-SCF3
Q27      27-428        3-I        H        C(Me)2CH2SO2Me    H        6-Me-2-SOCF3
Q27      27-429        3-I        H        C(Me)2CH2SO2Me    H        6-Me-2-SO2CF3
Q27      27-430        3-I        H        i-Pr                  H        6-Me-2-SC2F5
Q27      27-431        3-I        H        C(Me)2CH2SMe       H        6-Me-2-SC2F5
Q27      27-432        3-I        H        i-Pr                  H        6-Me-2-S-n-C3F7
Q27      27-433        3-I        H        C(Me)2CH2SMe       H        6-Me-2-S-n-C3F7
Q27      27-436        3-I        H        C(Me)2CH2SMe       H        6-Me-2-S-CH(CF3)2
                        表7(续)
Q        No.           Xn           R1      R2                  R3      Ym                           mp(℃)
Q27      27-434        3-I          H        i-Pr                  H        6-Me-2-SCF2CHF2
Q27      27-435        3-I          H        CH(Me)CH2SMe         H        6-Me-2-SCF2CHFCF3
Q27      27-437        3-I          H        i-Pr                  H        6-Me-2-NHCOCF3
Q27      27-438        3-I          H        i-Pr                  H        6-Me-2-NHCOC2F5              192
Q27      27-439        3-I          H        C(Me)2CH2SMe       H        6-Me-2-NHCOC2F5              205
Q27      27-440        3-I          H        i-Pr                  H        6-Me-2-NHCOC3F7-n
Q27      27-441        3-I          H        C(Me)2CH2SMe       H        6-Me-2-NHCOC3F7-n
Q27      27-442        3-I          H        C(Me)2CH2SMe       H        6-Me-2-NHCO-(2，4-Cl2-Ph)
Q27      27-443        3-I          H        i-Pr                  H        6-Me-2-NHCO-(4-CF3-Ph)
Q27      27-444        3-I          H        C(Me)2CH2SMe       H        6-Me-2-N(COC2F5)2
Q27      27-445        3-I          H        C(Me)2CH2SMe       H        6-Me-2-NHCH2CF3
Q27      27-446        3-I          H        C(Me)2CH2SMe       H        6-Me-2-NHCH2CF3
Q27      27-447        3-I          H        C(Me)2CH2SMe       H        6-Me-2-NHCH2C2F5
Q27      27-448        3-I          H        C(Me)2CH2SMe       H        6-Me-2-Cl                    173
Q27      27-449        3-CF3       H        C(Me)2CH2SMe       H        6-Me-2-i-C3F7                214
Q27      27-450        H            H        C(Me)2CH2SMe       H        6-Me-2-i-C3F7                155
Q27      27-451        3-F          H        C(Me)2CH2SMe       H        6-Me-2-i-C3F7                202
Q27      27-452        3-F          H        C(Me)2CH2SO2Me    H        6-Me-2-i-C3F7                197
Q27      27-453        3-Br         H        C(Me)2CH2SMe       H        6-Me-2-i-C3F7                206
Q27      27-454        3-Br         H        C(Me)2CH2SO2Me    H        6-Me-2-i-C3F7                225
Q27      27-455        3，4-Cl2    H        C(Me)2CH2SMe       H        6-Me-2-i-C3F7                259
Q27      27-456        3-CF3       H        i-Pr                  H        6-Me-2-i-C3F7                221
                        表7(续)
Q        No.         Xn          R1      R2                    R3     Ym                      mp(℃)
Q27      27-457      H           H        i-Pr                    H      6-Cl-2-i-C3F7         200
Q27      27-458      H           H        C(Me)2CH2SMe         H      6-Cl-2-i-C3F7         110
Q27      27-459      3-Cl        H        i-Pr                    H      6-Cl-2-i-C3F7         181
Q27      27-460      3-I         H        t-Eu                    H      6-Cl-2-i-C3F7         191
Q27      27-461      3-F         H        C(Me)2CH2SMe         H      6-Cl-2-i-C3F7         182
Q27      27-462      3-Cl        H        C(Me)2CH2SMe         H      6-Cl-2-i-C3F7         161
Q27      27-463      3，4-Cl2   H        C(Me)2CH2SMe         H      6-Cl-2-i-C3F7         153
Q27      27-464      3-CF3      H        C(Me)2CH2SMe         H      6-Cl-2-i-C3F7         165
Q27      27-465      3-NO2      H        C(Me)2CH2SMe         H      6-Cl-2-i-C3F7         235
Q27      27-466      3-I         H        i-Pr                    H      6-Me-2-O(4-CF3-Ph)     238
Q27      27-467      3-I         H        C(Me)2CH2SMe         H      6-Me-2-O(4-CF3-Ph)     111
Q27      27-468      3-I         H        C(Me)2CH2SOMe        H      6-Me-2-O(4-CF3-Ph)     106
Q27      27-469      3-I         H        C(Me)2CH2SO2Me      H      6-Me-2-O(4-CF3-Ph)     97
Q27      27-470      3-CF3      H        C(Me)2CH2SMe         H      6-Me-2-OCF2CHFOCF3
                                                                                                 无定形
Q27      27-471      3-I         H        i-Pr                    H      6-Me-2-OCF＝CFCF3      165
Q27      27-472      3-I         H        i-Pr                    H      6-Me-2-OCF2CHFOCF3    185
表7中，有些化合物是无定形或糊状的。这样的化合物的1H-NMR数据如下所示。
No            1H-NMR[δ(ppm/CDCl3)]
27-153        1.59(s.3H)，1.64(s.3H)，2.26(s.3H)，2.62(s.3H)，
              2.88(d.1H)，3.02(d.1H)，6.83(br.1H)，7.23(t.1H)，
              7.58(dd.1H)，7.78(d.1H)，8.00(dd.1H)，8.58(br.
              1H)，8.81(d.1H).
27-235        1.64(s.3H)，1.66(s.3H)，2.40(s.3H)，2.88(d.1H)，
              3.24(d.1H)，6.72(br.1H)，7.24(t.1H)，7.70(dd.1H)，
              7.74(d.1H)，8.03(dd.1H)，8.85(br.1H)，9.12(d.1H).
27-236        1.71(s.6H)，2.71(s.3H)，3.63(s.2H)，6.25(br.1H)，
              7.25(t.1H)，7.70(dd.1H)，7.75(dd.1H)，8.05(dd.
              1H)，8.81(br.1H)，9.11(d.1H).
27-238        1.68(s.3H)，1.72(s.3H)，2.49(s.3H)，2.99(d.1H)，
              3.21(d.1H)，6.76(br.1H)，7.21(t.1H)，7.50(dd.1H)，
              7.66(dd.1H)，7.84(dd.1H)，8.37(dd.1H)，8.68(d.
              1H)，9.75(br.1H).
27-239        1.80(s.6H)，2.87(s.3H)，3.73(s.2H)，6.23(br.1H)，
              7.23(t.1H)，7.43(dd.1H)，7.65(dd.1H)，7.82(dd.
              1H)，8.35(dd.1H)，8.64(d.1H)，9.88(br.1H).
27-244        1.60(s.3H)，1.63(s.3H)，2.41(s.3H)，2.84(d.1H)，
              3.31(d.1H)，4.02(s.1H)，6.59(br.1H)，7.21(t.1H)，
              7.34(dd.1H)，7.69(dd.1H)，7.99(dd.1H)，8.65(br.
              1H)，8.88(d.1H).
27-247        1.31(dd.6H)，3.50(s.3H)，4.33(m.1H)，5.60(d.1H)，
              7.19(t.1H)，7.68(d.1H)，7.74(dd.1H)，8.00(d.1H)，
              9.26(d.1H)，11.8(br.1H).
27-470        1.42(s.6H)，1.96(s.3H)，2.53(s.3H)，2.81(s.2H)，
              6.17(s.1H)，6.62(dt.1H)，6.90(d.1H)，7.66(t.1H)，
              7.85(d.1H)，8.03(d.1H)，8.63(d.1H)，8.71(s.1H).
Figure C0081000700781
                       表8(Z1＝Z2＝O)
Q          No.          Xn         R1      R2        R3      Ym                  mp(℃)
Q29        29-1         3-Cl       H        i-Pr        H        H
Q29        29-2         3-Cl       H        i-Pr        H        4-Me-6-C2F5
Q29        29-3         3-Br       H        i-Pr        H        4-Me-6-n-C3F7
Q29        29-4         3-NO2     H        i-Pr        H        4-Me-6-i-C3F7
Q29        29-5         3-I        H        i-Pr        H        H
Q29        29-6         3-I        H        i-Pr        H        6-Cl                136
Q29        29-7         3-I        H        i-Pr        H        6-C2F5
Q29        29-8         3-I        H        i-Pr        H        6-n-C3F7
Q29        29-9         3-I        H        i-Pr        H        6-i-C3F7
Q29        29-10        3-I        H        i-Pr        H        4-Me-6-C2F5
Q29        29-11        3-I        H        i-Pr        H        4-Me-6-n-C3F7
Q29        29-12        3-I        H        i-Pr        H        4-Me-6-i-C3F7
Q29        29-13        3-I        H        i-Pr        H        4-Me-5-C2F5
Q29        29-14        3-I        H        i-Pr        H        4-Me-5-n-C3F7
Q29        29-15        3-I        H        i-Pr        H        4-Me-5-i-C3F7
                                表8(续)
Q          No.          Xn         R1      R2                        R3      Ym            mp(℃)
Q29        29-16        3-I        H        t-Bu                        H        6-i-C3F7
Q29        29-17        3-I        H        t-Bu                        H        6-C2F5
Q29        29-18        3-I        H        t-Bu                        H        6-n-C3F7
Q29        29-19        3-I        H        t-Bu                        H        4-Me-6-i-C3F7
Q29        29-20        3-I        H        CH(CH3)CH2SCH3          H        4-Me-6-i-C3F7
Q29        29-21        3-I        H        CH(CH3)CH2SOCH3         H        4-Me-6-i-C3F7
Q29        29-22        3-I        H        CH(CH3)CH2SO2CH3       H        4-Me-6-i-C3F7
Q29        29-23        3-I        H        C(CH3)2CH2SCH3          H        4-Me-6-i-C3F7
Q29        29-24        3-I        H        C(CH3)2CH2SOCH3         H        4-Me-6-i-C3F7
Q29        29-25        3-I        H        C(CH3)2CH2SO2CH3     H        4-Me-6-i-C3F7
Q29        29-26        3-I        H        CH(CH3)CH2NHAc           H        4-Me-6-i-C3F7
Q29        29-27        3-I        H        C(CH3)2CH2NHAc          H        4-Me-6-i-C3F7
Q29        29-28        3-I        H        CH(CH3)CH2CH2OCH3     H        4-Me-6-i-C3F7
Q29        29-29        3-I        H        C(CH3)2CH2CH2OCH3    H        4-Me-6-i-C3F7
Q29        29-30        3-I        Et       Et                          H        H
Q29        29-31        3-I        Et       Et                          H        4-Me-6-C2F5
Q29        29-32        3-I        Et       Et                          H        4-Me-6-n-C3F7
Q29        29-33        3-I        Et       Et                          H        4-Me-6-i-C3F7
Q29        29-34        3-I        Et       Et                          H        6-Cl
Q29        29-35        3-I        Et       Et                          H        6-Br
Q29        29-36        3-I        Et       Et                          H        6-n-C3F7
Q29        29-37        3-CF3     H        i-Pr                        H        4-Me-6-C2F5
Q29        29-38        3-Ph       H        i-Pr                        H        4-Me-6-n-C3F7
                        表8(续)
Q          No.          Xn                R1      R2        R3      Ym                mp(℃)
Q29        29-39        3-SOCF3          H        i-Pr        H        4-Me-6-i-C3F7
Q29        29-40        3-C2F5          H        i-Pr        H        4-Me-6-C2F5
Q29        29-41        3-I-4-Cl          H        i-Pr        H        4-Me-6-n-C3F7
Q29        29-42        3-I-4-CF3        H        i-Pr        H        4-Me-6-i-C3F7
Q29        29-43        3-CF3-4-Cl       H        i-Pr        H        4-Me-6-C2F5
Q29        29-44        3-OCF2O-4        H        i-Pr        H        4-Me-6-n-C3F7
Q29        29-45        3-OCF2CF2O-4    H        i-Pr        H        4-Me-6-i-C3F7
                    表9(Z1＝Z2＝O)
Q        No.         Xn         R1      R2                        R3      Ym                    mp(℃)
Q32      32-1        3-Cl       H        i-Pr                        H        H
Q32      32-2        3-Cl       H        i-Pr                        H        4-Me-2-C2F5
Q32      32-3        3-Br       H        i-Pr                        H        4-Me-2-n-C3F7
Q32      32-4        3-NO2     H        i-Pr                        H        4-Me-2-i-C3F7
Q32      32-5        3-I        H        i-Pr                        H        2-C2F5
Q32      32-6        3-I        H        i-Pr                        H        2-n-C3F7
Q32      32-7        3-I        H        i-Pr                        H        2-i-C3F7
Q32      32-8        3-I        H        i-Pr                        H        4-Me-2-C2F5
Q32      32-9        3-I        H        i-Pr                        H        4-Me-2-n-C3F7
Q32      32-10       3-I        H        i-Pr                        H        4-Me-2-i-C3F7
Q32      32-11       3-I        H        i-Pr                        H        4，6-Cl2              257
Q32      32-12       3-I        H        t-Bu                        H        2-i-C3F7
Q32      32-13       3-I        H        t-Bu                        H        2-C2F5
Q32      32-14       3-I        H        t-Bu                        H        2-n-C3F7
Q32      32-15       3-I        H        t-Bu                        H        4-Me-2-i-C3F7
Q32      32-16       3-I        H        CH(CH3)CH2SCH3          H        4-Me-2-i-C3F7
Q32      32-17       3-I        H        CH(CH3)CH2SOCH3         H        4-Me-2-i-C3F7
Q32      32-18       3-I        H        CH(CH3)CH2SO2CH3       H        4-Me-2-i-C3F7
Q32      32-19       3-I        H        C(CH3)2CH2SCH3         H        4-Me-2-i-C3F7         202
Q32      32-20       3-I        H        C(CH3)2CH2SOCH3        H        4-Me-2-i-C3F7
Q32      32-21       3-I        H        C(CH3)2CH2SO2CH3      H        4-Me-2-i-C3F7
Q32      32-22       3-I        H        CH(CH3)CH2SEt             H        4-Me-2-i-C3F7
Q32      32-23       3-I        H        C(CH3)2CH2SEt            H        4-Me-2-i-C3F7
                        表9(续)
Q        No.          Xn                 R1      R2                         R3     Ym                  mp(℃)
Q32      32-24        3-I                H        CH(CH3)CH2CH2SCH3      H        4-Me-2-i-C3F7
Q32      32-25        3-I                H        C(CH3)2CH2CH2SCH3     H        4-Me-2-i-C3F7
Q32      32-26        3-I                Et       Et                           H        4-Me-2-C2F5
Q32      32-27        3-I                Et       Et                           H        4-Me-2-n-C3F7
Q32      32-28        3-I                Et       Et                           H        4-Me-2-i-C3F7
Q32      32-29        3-I                Et       Et                           H        2-Cl
Q32      32-30        3-I                Et       Et                           H        2-Br
Q32      32-31        3-I                Et       Et                           H        2-n-C3F7
Q32      32-32        3-CF3             H        i-Pr                         H        4-Me-2-C2F5
Q32      32-33        3-Ph               H        i-Pr                         H        4-Me-2-n-C3F7
Q32      32-34        3-SOCF3           H        i-Pr                         H        4-Me-2-i-C3F7
Q32      32-35        3-C2F5          H        i-Pr                         H        4-Me-2-C2F5
Q32      32-36        3-I-4-Cl           H        i-Pr                         H        4-Me-2-n-C3F7
Q32      32-37        3-I-4-CF3         H        i-Pr                         H        4-Me-2-i-C3F7
Q32      32-38        3-CF3-4-Cl        H        i-Pr                         H        4-Me-2-C2F5
Q32      32-39        3-OCF2O-4         H        i-Pr                         H        4-Me-2-n-C3F7
Q32      32-40        3-OCF2CF2O-4    H        i-Pr                         H        4-Me-2-i-C3F7
Q32      32-41        3-I                H        CH(Me)CH2SMe                H        4-Me-2-Cl            210
Q32      32-42        3-I                Et       Et                           H        4，6-(OCH2CF3)2
                                                                                                无定形
表9中，无定形化合物的1H-NMR数据如下所示。
No              1H-NMR[δ(ppm/CDCl3)]
32-42           1.04(s.3H)，1.31(t.3H)，3.10(m.3H)，3.42(m.1H)，
                3.80(m.1H)，4.96-4.74(m.4H)，7.22(t.1H)，7.87(d.
                1H)，8.04(dd.1H)，8.39(s.1H).
                        表10(Z1＝Z2＝O)
Q          No.         Xn         R1      R2                    R3    Ym                       mp(℃)，nD(℃)
Q33        33-1        H          H        i-Pr                    H      4，6-(OMe)2              61
Q33        33-2        3-Cl       H        i-Pr                    H      H
Q33        33-3        3-Cl       H        i-Pr                    H      5-C2F5
Q33        33-4        3-Br       H        i-Pr                    H      5-n-C3F7
Q33        33-5        3-NO2     H        i-Pr                    H      5-i-C3F7
Q33        33-6        3-I        H        i-Pr                    H      5-C2F5
Q33        33-7        3-I        H        i-Pr                    H      5-n-C3F7
Q33        33-8        3-I        H        i-Pr                    H      5-i-C3F7
Q33        33-9        3-I        H        i-Pr                    H      4，6-OMe2
                                                                                    nD 1.5672(20.9)
Q33        33-10       3-I        H        i-Pr                    H      4，6-OMe2-5-i-C3F7
                                                                                    nD 1.5045(21.9)
Q33        33-11       3-I        H        t-Bu                    H      5-i-C3F7
Q33        33-12       3-I        H        t-Bu                    H      5-C2F5
Q33        33-13       3-I        H        t-Bu                    H      5-n-C3F7
Q33        33-14       3-I        H        CH(CH3)CH2SCH3      H      5-i-C3F7
Q33        33-15       3-I        H        CH(CH3)CH2SOCH3     H      5-i-C3F7
                                表10(续)
Q          No.          Xn         R1      R2                          R3      Ym        mp(℃)，nD(℃)
Q33        33-16        3-I        H        CH(CH3)CH2SO2CH3        H        5-i-C3F7
Q33        33-17        3-I        H        C(CH3)2CH2SCH3          H        5-i-C3F
Q33        33-18        3-I        H        C(CH3)2CH2SOCH3         H        5-i-C3F7
Q33        33-19        3-I        H        C(CH3)2CH2SO2CH3       H        5-i-C3F7
Q33        33-20        3-I        H        CH(CH3)CH2SEt              H        5-i-C3F7
Q33        33-21        3-I        H        C(CH3)2CH2SEt             H        5-i-C3F7
Q33        33-22        3-I        H        CH(CH3)CH2CH2SCH3       H        5-i-C3F7
Q33        33-23        3-I        H        C(CH3)2CH2CH2SCH3      H        5-i-C3F7
Q33        33-24        3-I        Et       Et                            H        5-C2F5
Q33        33-25        3-I        Et       Et                            H        5-n-C3F7
Q33        33-26        3-I        Et       Et                            H        5-i-C3F7
Q33        33-27        3-I        Et       Et                            H        5-Cl
Q33        33-28        3-I        Et       Et                            H        5-Br
Q33        33-29        3-I        Et       Et                            H        5-n-C3F7
Figure C0081000700851
                        表11(Z1＝Z2＝O)
Q        No.          Xn         R1      R2                         R3      Ym                 mp(℃)
Q34      34-1         3-Cl       H        i-Pr                         H        H
Q34      34-2         3-Cl       H        i-Pr                         H        3-Me-5-C2F5
Q34      34-3         3-Br       H        i-Pr                         H        3-Me-5-n-C3F7
Q34      34-4         3-NO2     H        i-Pr                         H        3-Me-5-i-C3F7
Q34      34-5         3-I        H        i-Pr                         H        H                  185
Q34      34-6         3-I        H        i-Pr                         H        5-I                198
Q34      34-7         3-I        H        i-Pr                         H        5-C2F5
Q34      34-8         3-I        H        i-Pr                         H        5-n-C3F7
Q34      34-9         3-I        H        i-Pr                         H        5-i-C3F7
Q34      34-10        3-I        H        i-Pr                         H        3-Me-5-C2F5
Q34      34-11        3-I        H        i-Pr                         H        3-Me-5-n-C3F7
Q34      34-12        3-I        H        i-Pr                         H        3-Me-5-i-C3F7
Q34      34-13        3-I        H        i-Pr                         H        6-Me-5-C2F5
Q34      34-14        3-I        H        i-Pr                         H        6-Me-5-n-C3F7
Q34      34-15        3-I        H        i-Pr                         H        6-Me-5-i-C3F7
Q34      34-16        3-I        H        t-Bu                         H        5-i-C3F7
Q34      34-17        3-I        H        t-Bu                         H        5-C2F5
Q34      34-18        3-I        H        t-Bu                         H        5-n-C3F7
Q34      34-19        3-I        H        t-Bu                         H        3-Me-5-i-C3F7
Q34      34-20        3-I        H        CH(CH3)CH2SCH3           H        3-Me-5-i-C3F7
Q34      34-21        3-I        H        CH(CH3)CH2SOCH3          H        3-Me-5-i-C3F7
Q34      34-22        3-I        H        CH(CH3)CH2SO2CH3        H        3-Me-5-i-C3F7
Q34      34-23        3-I        H        C(CH3)2CH2SCH3          H        3-Me-5-i-C3F7
                            表11(续)
Q        No.        Xn               R1      R2                         R3     Ym                mp(℃)
Q34      34-24      3-I              H        C(CH3)2CH2SOCH3        H      3-Me-5-i-C3F7
Q34      34-25      3-I              H        C(CH3)2CH2SO2CH3      H      3-Me-5-i-C3F7
Q34      34-26      3-I              H        CH(CH3)CH2NHAc            H      3-Me-5-i-C3F7
Q34      34-27      3-I              H        C(CH3)2CH2NHAc           H      3-Me-5-i-C3F7
Q34      34-28      3-I              H        CH(CH3)CH2CH2OCH3       H      3-Me-5-i-C3F7
Q34      34-29      3-I              H        C(CH3)2CH2CH2OCH3     H      3-Me-5-i-C3F7
Q34      34-30      3-I              Et       Et                           H      H                 144
Q34      34-31      3-I              Et       Et                           H      3-Me-5-C2F5
Q34      34-32      3-I              Et       Et                           H      3-Me-5-n-C3F7
Q34      34-33      3-I              Et       Et                           H      3-Me-5-i-C3F7
Q34      34-34      3-I              Et       Et                           H      5-Cl
Q34      34-35      3-I              Et       Et                           H      5-Br
Q34      34-36      3-I              Et       Et                           H      5-n-C3F7
Q34      34-37      3-CF3           H        i-Pr                         H      3-Me-5-C2F5
Q34      34-38      3-Ph             H        i-Pr                         H      3-Me-5-n-C3F7
Q34      34-39      3-SOCF3         H        i-Pr                         H      3-Me-5-i-C3F7
Q34      34-40      3-C2F5         H        i-Pr                         H      3-Me-5-C2F5
Q34      34-41      3-I-4-Cl         H        i-Pr                         H      3-Me-5-n-C3F7
Q34      34-42      3-I-4-CF3       H        i-Pr                         H      3-Me-5-i-C3F7
Q34      34-43      3-CF3-4-Cl      H        i-Pr                         H      3-Me-5-C2F5
Q34      34-44      3-OCF2O-4       H        i-Pr                         H      3-Me-5-n-C3F7
Q34      34-45      3-OCF2CF2O-4   H        i-Pr                         H      3-Me-5-i-C3F7
Q34      34-46      3-I              H        Et                           H      5-i-C3F7          175
                                表11(续)
Q          No.         Xn          R1      R2        R3      Ym        mp(℃)
Q3         3-1         3-I         H        i-Pr        H        H
Q7         7-1         3-I         H        i-Pr        H        H
Q11        11-1        3-I         H        i-Pr        H        H
Q14        14-1        3-I         H        i-Pr        H        H
Q15        15-1        3-I         H        i-Pr        H        H         185
Q18        18-1        3-I         H        i-Pr        H        H
Q20        20-1        3-I         H        i-Pr        H        H
Figure C0081000700881
                                表12  (Z1＝Z2＝O)
Q          No.         Xn          R1      R2        R3      W          Ym       性质，Mp(℃)
Q16        16-1        3-Cl        H        i-Pr        H        N-i-Pr     SMe      糊状
Q16        16-2        3-Cl        H        i-Pr        H        N-n-Pr     SMe      糊状
Q44        43-1        H           H        i-Pr        H        S          6-Cl     47
实施例
下面，本发明的典型实施例如下所示。本发明决不限于这些实施例。
制备例1
(1-1)N-(4-甲基-3-三氟甲基异噁唑-5-基)-3-碘邻苯二甲酰亚胺的制备
在20ml乙酸中，溶解0.6g 3-碘邻苯二甲酸酐和0.44g 5-氨基-4-甲基-3-三氟甲基异噁唑，在加热回流下反应9小时。反应完全后，在减压下蒸馏除去溶剂，将残余物溶于乙酸乙酯，用稀盐酸、饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗涤，然后在硫酸钠上干燥。在减压下蒸馏除去溶剂后，残余物经过硅胶柱色谱纯化，用己烷与乙酸乙酯的3/1混合物作为洗脱剂，得到0.71g目标产物。
性质：m.p.105℃；收率：69％
(1-2)N1-(4-甲基-3-三氟甲基异噁唑-5-基)-N2-异丙基-3-碘邻苯二甲酰胺(化合物No.Q6-8)的制备
在50ml二噁烷中溶解1.06g N-(4-甲基-3-三氟甲基异噁唑-5-基)-3-碘邻苯二甲酰亚胺。然后，向上述所得溶液中加入0.4g异丙胺，在室温下搅拌3小时。反应完全后，在减压下蒸馏除去溶剂，残余物经过硅胶柱色谱纯化，用己烷与乙酸乙酯的2/1混合物作为洗脱剂，得到0.32g目标产物。
性质：m.p.103℃；收率：26％
制备例2
(2-1)N1-[2-(1，1-二甲基乙基)-1，3，4-噻二唑-4-基]-N2，N2-二乙基-3-碘邻苯二甲酰胺(化合物No.Q19-34)的制备
在20ml四氢呋喃中溶解0.5g N，N-二乙基-3-碘邻苯二甲酸2-酰胺和0.27g 5-氨基-2-(1，1-二甲基乙基)-1，3，4-噻二唑。加入0.28g二乙基磷酰氰和0.18g三乙胺后，在加热回流下进行反应7小时。反应完全后，向反应混合物中加入乙酸乙酯，将所得乙酸乙酯溶液用稀盐酸、饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗涤，在硫酸钠上干燥。蒸馏除去溶剂后，残余物经过硅胶柱色谱纯化，用己烷与乙酸乙酯的3/1混合物洗脱，得到0.11g目标产物。
性质：m.p.59℃；收率：16％
制备例3
(3-1)N1-(4-甲基-2-七氟异丙基吡啶-5-基)-N2-(1-甲基-2-甲硫基乙基)-3-碘邻苯二甲酰胺(化合物No.Q27-144)的制备
在4ml乙腈中溶解0.37g N-(1-甲基-2-甲硫基乙基)-3-碘邻苯二甲酸异酰亚胺(isoimide)和0.28g 5-氨基-4-甲基-2-七氟异丙基吡啶。加入催化量的三氟乙酸后，将所得混合物在室温下搅拌30分钟。过滤收集所得晶体，得到0.28g目标产物。
性质：m.p.225℃；收率：44％
制备例4：2-氨基-3-甲基-6-五氟乙基吡啶(化合物No.IV-1)的制备
向20ml二甲基亚砜中加入2.34g(0.01mol)2-氨基-5-碘-3-甲基吡啶、2.5g金属铜粉和3.7g(0.015mol)碘代五氟乙烷。将混合物保持在110℃下，剧烈搅拌6小时。将反应混合物冷却至室温后，将混合物倒在500ml冰水中，充分搅拌。过滤除去不溶物，用300ml乙酸乙酯从滤液中萃取目标产物。将萃取溶液用水洗涤，在无水硫酸钠上干燥，在减压下浓缩。残余物经过柱色谱纯化，用乙酸乙酯与己烷的3/7混合物作为洗脱剂，得到1.1g目标产物(收率20％)。
1H-NMR[δ(CDCl3)]：2.17(s，3H)，4.82(br，2H)，7.42(d，1H)，8.16(s，1H)，
制备例5：3-氨基-2-甲氧基-6-(七氟丙-2-基)吡啶(化合物No.IV-15)的制备
向20ml甲基叔丁基醚中加入3.2g(0.026mol)3-氨基-2-甲氧基吡啶、0.6g氯化三乙基苄基铵、2.0g碳酸钠和10.0g(0.031mol)2-碘七氟丙烷。在30℃下搅拌混合物的同时，向其中滴加2.8g亚硫酸氢钠(sodium hydrosulfite)的10ml水溶液。滴加后，所得混合物在室温下反应20小时，然后分离有机层，用水洗涤，在无水硫酸钠上干燥，在减压下蒸馏除去溶剂。残余物经过柱色谱纯化，用乙酸乙酯与己烷的3/7混合物作为洗脱剂，得到2.0g目标产物(收率26％)。
1H-NMR[δ(CDCl3)]：3.96(s，3H)，4.03(br，2H)，6.91(d，1H)，7.10(dd，1H)
制备例6：3-氨基-6-(1，1，1，3，3，3-六氟异丙氧基)吡啶(化合物No.IV-27)的制备
在不超过5℃的温度下，将氢化钠(2.6g)分批加入到11.3g1，1，1，3，3，3-六氟-2-丙醇的50ml四氢呋喃溶液中，在上述相同温度下搅拌30分钟。然后，加入4.7g 2-氯-5-硝基吡啶，在室温下搅拌12小时。将反应混合物倒在200ml冰水中，用300ml乙酸乙酯萃取。将萃取溶液用水洗涤，在无水硫酸钠上干燥，浓缩。残余物经过柱色谱纯化，用乙酸乙酯与己烷的1/10混合物作为洗脱剂，得到6.2g 2-(1，1，1，3，3，3-六氟异丙氧基)-5-硝基苯(收率64％)。
向20ml乙酸中加入4.4g如上得到的2-(1，1，1，3，3，3-六氟异丙氧基)-5-硝基苯和4.2g电解铁。将所得混合物在60-65℃下搅拌30分钟。将反应混合物冷却，用6N氢氧化钠水溶液中和，过滤除去不溶物，将滤液用300ml叔丁基甲基醚萃取。将萃取溶液用氯化钠水溶液洗涤，在无水硫酸钠上干燥，浓缩。残余物经过柱色谱纯化，用乙酸乙酯与己烷的2/3混合物作为洗脱剂，得到3.6g 3-氨基-6-(1，1，1，3，3，3-六氟异丙氧基)吡啶(收率92％)。
含有本发明的式(I)的邻苯二甲酰胺衍生物作为活性成分的农艺杀虫剂适合于防治各种害虫，例如农业园艺害虫、储存谷物的害虫、卫生害虫、线虫等，它们对水稻、果树、蔬菜、其他作物、花卉、观赏植物等是有害的。它们具有显著的杀虫作用，例如鳞翅目，包括棉褐带卷蛾( Adoxophyes  orana  fasciata)、smaller teatortrix( Adoxophyes  sp.)、苹小食心虫( Grapholita inopinata)、梨小食心虫( Grapholita  molesta)、大豆食心虫( Leguminovora  glycinivorella)、桑小卷蛾( Olethreutes mori)、苯细蛾( Caloptilla  theivora)、猛花细蛾( Caloptilia zachrysa)、金纹小潜细蛾( Phyllonorycter  ringoniella)、梨潜皮细蛾( Spulerina  astaurota)、菜粉蝶日本亚种( Pieris  rapae crucivora)、烟芽夜蛾( Heliothis  sp.)、苹果皮小卷蛾( Laspey resia  pomonella)、小菜蛾( Plutella  xylostella)、苹果银蛾( Argyresthia  conjugella)、桃柱果蛾( Carposina  niponensis)、二化螟( Chilo  suppressalis)、稻纵卷叶野螟( Cnaphalocrocis medinalis)、烟草粉斑螟( Ephestia  elutella)、桑绢野螟( Glyphodes  pyloalis)、三化螟( Scirpophaga  incertulas)、直纹稻弄蝶( Parnara  guttata)、粘虫( Pseudaletia  separata)、稻蛀茎夜蛾( Sesamia  inferens)、斜纹贪夜蛾( Spodoptera  litura)、贪夜蛾( Spodoptera  exigua)等；半翅目，包括二点夜蝉( Macrosteles  fascifrons)、黑尾夜蝉( Nephotettix cincticepts)、褐飞虱( Nilaparvata  lugens)、白背飞虱( Sogatella  furcifera)、橘木虱( Diaphorina  citri)、日本葡萄粉虱( Aleurolobus  taonabae)、甘薯粉虱( Bemisia  tabaci)、温室粉虱( Trialeurodes  vaporariorum)、萝卜蚜( Lipaphis erysimi)、桃蚜( Myzus  persicae)、角蜡蚧( Ceroplastes ceriferus)、橘绵蚧( Pulvinaria  aurantii)、樟网盾蚧( Pseudaonidia  duplex)、圣琼斯康顿蚧( Comstockaspis perniciosa)、矢尖盾蚧( Unapsis  yanonensis)等；垫刃线虫科，包括多色异丽金龟( Anomala  rufocuprea)、日本弧丽金龟( Popillia  japonica)、烟草窃蠹( Lasioderma  serricorne)、褐粉蠹( Lyctus  brunneus)、马铃薯瓢虫( Epilachna vigintiotopunctata)、绿豆象( Callosobruchus  chinensis)、番茄象( Listroderes  costirostris)、玉米象( Sitophilus zeamais)、棉铃象( Anthonomus  gradis  gradis)、稻水象( Lissorhoptrus  oryzophilus)、黄守瓜( Aulacophora femoralis)、水稻负泥虫( Oulema  oryzae)、黄曲条菜跳甲( Phyllotreta  striolata)、纵坑切梢小蠹( Tomicus  piniperda)、马铃薯叶甲( Leptinotarsa  decemlineata)、Mexican bean beetle( Epilachna  varivestis)、corn rootworm( Diabrotica  sp.)等；双翅目，包括瓜寡鬃实蝇( Dacus(Zeugodacus)  cucurbitae)、橘果实蝇( Dacus(Bactrocera)  dorsalis)、大麦毛眼水蝇( Agnomyza oryzae)、葱地种蝇( Delia  antiqua)、灰地种蝇( Delia  platura)、soybean pod gall midge( Asphondylia  sp.)、家蝇( Musca domestica)、尖音库蚊( Culex  pipiens  pipiens)等；和垫刃线虫科，包括短体线虫( Pratylenchus  sp.)、咖啡短体线虫( Pratylenchus  coffeae)、马铃薯金线虫( Globodera rostochiensis)、根结线虫( Meloidogyne  sp.)、半穿刺线虫( Tylenchulus  semipenetrans)、Aphelenchus sp.( Aphelenchus avenae)、菊叶芽滑刃线虫( Aphelenchoides  ritzemabosi)等。
含有本发明的由式(I)代表的邻苯二甲酰胺衍生物的农业园艺药剂、特别是农业园艺杀虫剂对上述例举的昆虫害虫、卫生害虫和/或线虫具有显著的防治作用，它们对稻田作物、旱田作物、果树、蔬菜和其他作物、花卉和观赏植物等是有害的。因此，在昆虫害虫、卫生害虫或线虫预期出现的季节、在它们出现之前或者在确认它们出现之时，将杀虫剂施用于稻田水、茎和叶或稻田土壤、旱田、果树、蔬菜、其他作物或花卉和观赏植物，可以表现出本发明的农业园艺杀虫剂的所需效果。
一般来说，在按照普通的农用化学品制备方法制成常用剂型之后，使用本发明的农业园艺药剂。
也就是说，将式(I)的邻苯二甲酰胺衍生物和适当载体以及可选的助剂按适当比例混合，通过溶解、分离、悬浮、混合、浸渍、吸附或附着作用，制成适合的剂型，例如悬浮液、乳油、可溶性浓缩物、可湿性粉剂、颗粒剂、粉剂或片剂。
用在本发明中的惰性载体既可以是固体也可以是液体。关于固体载体，可以提及大豆粉、谷物粉、木粉、树皮粉、锯屑、烟草茎粉、胡桃壳粉、糠、纤维素粉、植物提取残余物、合成聚合物或树脂粉、粘土(例如高岭土、膨润土和酸性粘土)、滑石(例如滑石和叶蜡石)、二氧化硅材料(例如硅藻土、硅沙、云母、白炭，即合成的高分散性硅酸，也称微细粉碎的水合二氧化硅或水合硅酸，有些商业上可得到的产品含有硅酸钙作为主要组分)、活性炭、硫粉、浮石、煅烧硅藻土、磨碎的砖、飞灰、沙子、碳酸钙、磷酸钙和其他无机或矿物粉末，化学肥料，例如硫酸铵、磷酸铵、硝酸铵、尿素、氯化铵等，和堆肥。这些载体既可以单独使用，也可以使用两种或多种载体的混合物。
液体载体本身具有溶解性，或者虽然没有溶解性但是能够借助助剂分散活性成分。下面是液体载体的典型实例，它们既可以单独使用，也可以使用其混合物：水；醇，例如甲醇、乙醇、异丙醇、丁醇和乙二醇；酮，例如丙酮、甲乙酮、甲基异丁基酮、二异丁酮和环己酮；醚，例如***、二噁烷、溶纤剂、二丙醚和四氢呋喃；脂族烃，例如煤油和矿物油；芳族烃，例如苯、甲苯、二甲苯、溶剂石脑油和烷基萘；卤代烃，例如二氯乙烷、氯仿、四氯化碳和氯苯；酯，例如乙酸乙酯、邻苯二甲酸二异丙基酯、邻苯二甲酸二丁基酯和邻苯二甲酸二辛基酯；酰胺，例如二甲基甲酰胺、二乙基甲酰胺和二甲基乙酰胺；腈，例如乙腈；和二甲基亚砜。
下面是助剂的典型实例，它们是根据目的而使用的，单独使用或者在有些情况下两种或多种助剂结合使用，或者根本不必使用。
为了乳化、分散、溶解和/或湿润活性成分，使用表面活性剂。关于表面活性剂，可以例举聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯高级脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脱水山梨醇单月桂酸酯、聚氧乙烯脱水山梨醇单油酸酯、烷基芳基磺酸盐、萘磺酸缩合产物、木素磺酸盐和高级醇硫酸酯盐。
进而，为了稳定活性成分的分散液，增粘之和/或粘合之，可以使用的助剂例如酪蛋白、明胶、淀粉、甲基纤维素、羧甲基纤维素、***胶、聚乙烯醇、松节油、米糠油、膨润土和木素磺酸盐。
为了提高固体产品的可流动性，可以使用的助剂例如蜡、硬脂酸酯和烷基磷酸酯。
诸如萘磺酸缩合产物和磷酸盐的缩聚物等助剂可以用作可分散产品的胶溶剂。
诸如硅酮油等助剂也可以用作消泡剂。
活性成分的含量可以因需要而异，每100重量份制剂含0.01至80重量份。在粉剂或颗粒剂中，其适合的含量为0.01至50重量％。在乳油和可流动的可湿性粉剂中，适合的含量也是0.01至50重量％。
本发明的农艺杀虫剂用于以下列方式防治各种害虫。也就是说，将其直接或者用水等适当稀释或悬浮后，施用于预期出现害虫的作物或者不希望出现害虫的场所，用量对抑制害虫来说是有效的。
本发明的农艺杀虫剂的施用剂量因各种因素而异，例如目的、所要防治的害虫、植物的生长状态、害虫出现的趋势、天气、环境条件、剂型、施药方法、施药场所和施药时间。根据目的，可以在每10公亩0.1g至10kg(以活性成分化合物计)的范围内加以适当选择。
本发明的农艺杀虫剂可以与其他农业和园艺病害或害虫防治剂混合使用，目的是扩大可防治病害和害虫种类的范围，延长有效施药时间或者减少剂量。
下面，介绍本发明的典型制剂例和试验例。本发明决不限于这些
实施例。
在制剂例中，术语“份”表示“重量份”。
制剂例1
表2至12所列各化合物                           50份
二甲苯                                        40份
聚氧乙烯壬基苯基醚与烷基苯磺酸钙的混合物      10份
将上述成分均匀混合进行溶解，制得乳油。
制剂例2
表2至12所列各化合物                          3份
粘土粉                                       82份
硅藻土粉                                     15份
将上述成分均匀混合并研磨，制得粉剂。
制剂例3
表2至12所列各化合物                          5份
膨润土与粘土的混合粉末                       90份
木素磺酸钙                                   5份
将上述成分均匀混合，将所得混合物与适量水一起捏和，然后造粒并干燥，制得颗粒剂。
制剂例4
表2至12所列各化合物                          20份
高岭土与合成高分散性硅酸的混合物             75份
聚氧乙烯壬基苯基醚与烷基苯磺酸钙的混合物     5份
将上述成分均匀混合并研磨，制成可湿性粉剂。
试验例1：对小菜蛾( Plutella  xylostella)的杀虫作用
释放成年小菜蛾，使其在中国卷心菜幼苗上产卵。释放后两天，将沉积有卵的幼苗浸入液体化学品达约30秒钟，所述液体化学品是这样制备的，即，稀释含有表2至12所列各化合物作为活性成分的制剂，调节浓度至1,000ppm。风干后，放置在恒温25℃的房间内。浸入后六天，统计孵化的昆虫。根据下列等式计算死亡率，根据如下所示标准判断杀虫作用。试验重复进行三组，每组10只昆虫。
Figure C0081000700961
标准：
A---死亡率100％
B---死亡率99-90％
C---死亡率89-80％
D---死亡率79-50％
在上述试验中，表现B级或以上活性的化合物如下：
Q1-12，Q1-41，Q1-42，Q4-6，Q4-8，Q4-12，Q4-45，Q6-6，
Q6-8，Q8-1，Q8-2，Q8-3，Q8-5，Q8-11，Q8-13，Q8-14，Q8-
15，Q8-53，Q9-15，Q10-7，Q15-1，Q26-1，Q26-11，Q26-29，
Q26-30，Q26-31，Q26-32，Q26-33，Q26-43，Q27-29，Q27-30，
Q27-31，Q27-32，Q27-81，Q27-98，Q27-124，Q27-125，Q27-
126，Q27-127，Q27-128，Q27-129，Q27-130，Q27-131，Q27-
132，Q27-133，Q27-134，Q27-135，Q27-136，Q27-137，Q27-
138，Q27-139，Q27-140，Q27-141，Q27-142，Q27-143，Q27-
144，Q27-145，Q27-150，Q27-151，Q27-153，Q27-155，Q27-
164，Q27-230， Q27-231，Q27-232，Q27-233，Q27-234，Q27-
235，Q27-236，Q27-238，Q27-239，Q27-240，Q27-241，Q27-
242，Q27-243，Q27-244，Q27-245，Q27-246，Q27-247，Q27-
248至Q27-265，Q27-267，Q27-268，Q27-270，Q27-273至
Q27-280，Q27-282至Q27-284，Q27-289，Q27-297，Q27-298，
Q27-305至Q27-309，Q27-316至Q27-318，Q27-323至Q27-
327，Q27-332，Q27-334，Q27-335，Q27-336至Q27-339，
Q27-347，Q27-352，Q27-353，Q27-354，Q27-355，Q27-359，
Q27-360，Q27-378，Q27-384，Q27-387，Q27-388，Q27-391，
Q27-393，Q27-396，Q27-397，Q27-402至Q27-405，Q27-407，
Q27-413，Q27-414，Q27-439，Q27-449至Q27-457，Q27-459
至Q27-469，Q32-11，Q32-19，Q33-1，Q33-10，Q34-30，Q34-
46和Q42-1。
试验例2：对斜纹贪夜蛾( Spodoptera  litura)的杀虫作用
将一片卷心菜叶(栽培品种；Shikidori)浸入液体化学品达约30秒钟，所述液体化学品是这样制备的，即，稀释含有表2至12所列各化合物作为活性成分的制剂，调节浓度至500ppm。风干后，将其放置在直径9cm的塑料陪替氏培养皿中，接种斜纹贪夜蛾的二龄幼虫，然后密封培养皿，放置在恒温25℃的房间内。接种后八天，统计死亡的和存活的数量。根据下列等式计算死亡率，根据试验例1所示标准判断杀虫作用。试验重复进行三组，每组10只昆虫。
Figure C0081000700981
在上述试验中，表现B级或以上活性的化合物如下：
Q26-1，Q26-11，Q2 6-29，Q26-30，Q26-31，Q26-32，Q26-33，
Q26-43，Q27-29，Q27-30，Q27-31，Q27-32，Q27-81，Q27-98，
Q27-124，Q27-125，Q27-126，Q27-127，Q27-128，Q27-129，
Q27-130，Q27-131，Q27-132，Q27-133，Q27-134，Q27-135，
Q27-136，Q27-137，Q27-138，Q27-139，Q27-140，Q27-141，
Q27-142，Q27-143，Q27-144，Q27-145，Q27-150，Q27-151，
Q27-152，Q27-153，Q27-155，Q27-164，Q27-230，Q27-231，
Q27-232，Q27-233，Q27-234，Q27-235，Q27-236，Q27-238，
Q27-239，Q27-240，Q27-241，Q27-242，Q27-243，Q27-244，
Q27-245，Q27-24 6，Q27-247，Q27-248至Q27-265，Q27-267，
Q27-268，Q27-270，Q27-273至Q27-280，Q27-282至Q27-
284，Q27-289， Q27-297，Q27-298，Q27-305至Q27-309，
Q27-316至Q27-318，Q27-323至Q27-327，Q27-332，Q27-
334，Q27-335， Q27-336至Q27-339，Q27-347，Q27-352，
Q27-353，Q27-354，Q27-355，Q27-359，Q27-360，Q27-378，
Q27-384，Q27-387，Q27-388，Q27-397，Q27-402至Q27-405，
Q27-407，Q27-413，Q27-414，Q27-439，Q27-459，Q27-466，
Q32-19和Q34-46。
试验例3：对稻纵卷叶野螟( Cnaphalocrosis  medinalis)的杀虫作用
将处于6至8叶期的稻植株叶片浸入液体化学品达约30秒钟，所述液体化学品是这样制备的，即，稀释含有表2至12所列各化合物作为活性成分的制剂，调节浓度至500ppm。风干后，将叶片放置在直径9cm的塑料陪替氏培养皿中，培养皿底部覆盖有湿润的滤纸。在叶片上接种稻纵卷叶野螟的三龄幼虫，然后将培养皿放置在恒温在25℃和湿度为70％的房间内。接种后四天，统计死亡的和存活的数量，根据试验例1所示标准判断杀虫作用。试验重复进行三组，每组10只昆虫。
在上述试验中，表现B级或以上活性的化合物如下：
Q26-1，Q26-29，Q26-30，Q26-31，Q26-32，Q26-33，Q27-29，
Q27-30，Q27-31，Q27-32，Q27-81，Q27-98，Q27-124，Q27-
125，Q27-126，Q27-127，Q27-128，Q27-129，Q27-130，Q27-
131，Q27-132，Q27-133，Q27-134，Q27-135，Q27-136，Q27-
137，Q27-138， Q27-139，Q27-140，Q27-141，Q27-142，Q27-
143，Q27-144，Q27-145和Q27-164。

Claims (4)

1.由下述通式(I)代表的邻苯二甲酰胺衍生物：
Figure C008100070002C1
其中R1、R2和R3可以是相同或不同的，各自代表氢原子、C1-6烷基、C1-6烷硫基C1-6烷基、C1-6烷基亚磺酰基C1-6烷基、C1-6烷基磺酰基C1-6烷基，
X代表氢原子、卤原子、硝基、CF3、C1-6烷基，
n代表0-4的整数，
Z1和Z2代表氧原子，
Q代表选自由下式Q1、Q2、Q4、Q5、Q6、Q8、Q9、Q10、Q13、Q15、Q16、Q19、Q26、Q27、Q29、Q32、Q33、Q34、Q43组成的组的杂环基：
Figure C008100070003C1
Y代表氢原子、卤原子、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷氧基羰基、苯基、苯氧基、卤代苯氧基、C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷硫基、卤代C1-6烷基磺酰基、卤代C1-6烷氧基卤代C1-6烷氧基、卤代C1-6烷酰基氨基，
m代表0-4的整数，
W代表O、S或N-R13，其中R13代表氢原子、C1-6烷基或卤代C1-6烷基；
条件是(1)若X、R1和R3同时代表氢原子，Z1和Z2同时代表氧原子，Q代表Q27，Y是2-位的氯原子，则R2不是1，2，2-三甲基丙基；
(2)若X、R1和R3同时代表氢原子，Z1和Z2同时代表氧原子，Q代表Q27，且m是0，则R2不是1，2，2-三甲基丙基；和
(3)若X、R1和R3同时代表氢原子，Z1和Z2同时代表氧原子，Q代表Q16，且Y代表甲硫基，则R2不是氢原子和甲基。
2.农业园艺杀虫剂，含有由下述通式(I)代表的邻苯二甲酰胺衍生物作为其活性成分：
其中R1、R2和R3可以是相同或不同的，各自代表氢原子、C1-6烷基、C1-6烷硫基C1-6烷基、C1-6烷基亚磺酰基C1-6烷基、C1-6烷基磺酰基C1-6烷基，
X代表氢原子、卤原子、硝基、CF3、C1-6烷基，
n代表0-4的整数，
Z1和Z2代表氧原子，
Q代表选自由下式Q1、Q2、Q4、Q5、Q6、Q8、Q9、Q10、Q13、Q15、Q16、Q19、Q26、Q27、Q29、Q32、Q33、Q34、Q43组成的组的杂环基：
Y代表氢原子、卤原子、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷氧基羰基、苯基、苯氧基、卤代苯氧基、C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷硫基、卤代C1-6烷基磺酰基、卤代C1-6烷氧基卤代C1-6烷氧基、卤代C1-6烷酰基氨基，
m代表0-4的整数，
W代表O、S或N-R13，其中R13代表氢原子、C1-6烷基或卤代C1-6烷基；
条件是若X、R1和R3同时代表氢原子，Z1和Z2同时代表氧原子，Q代表Q27，Y是2-位的氯原子，则R2不是1，2，2-三甲基丙基。
3.使用农业园艺杀虫剂的方法，其特征在于为了防治对有用作物有害的生物，用有效量的根据权利要求2的农业园艺杀虫剂处理目标农作物或施用于土壤。
4.由下述通式(IV，)代表的杂环胺衍生物：
         Q’-NH2                    (IV’)
其中：
(1)在Q’代表Q26、Q32和Q34之一的情况下，
Y可以是相同或不同的，代表卤原子、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基或卤代C1-6烷硫基，m代表1-4的整数，总数为m的Y中至少有一个是全氟C2-6烷基；和
(2)在Q，代表Q27的情况下，
Y可以是相同或不同的，代表卤原子、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基，m代表1-4的整数，总数为m的Y中至少有一个是全氟C2-6烷基、卤代C1-6烷氧基或卤代C1-6烷硫基，
其条件是Y不是2，2，2-三氟乙氧基。
CNB008100071A 1999-07-05 2000-07-04 邻苯二甲酰胺衍生物、其制备中的中间体和农业/园艺杀虫剂及其使用方法 Expired - Fee Related CN1195734C (zh)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP190746/1999 1999-07-05
JP19074699 1999-07-05
JP190746/99 1999-07-05
JP2000080991 2000-03-22
JP080991/2000 2000-03-22
JP080991/00 2000-03-22

Publications (2)

Publication Number Publication Date
CN1360573A CN1360573A (zh) 2002-07-24
CN1195734C true CN1195734C (zh) 2005-04-06

Family

ID=26506279

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB008100071A Expired - Fee Related CN1195734C (zh) 1999-07-05 2000-07-04 邻苯二甲酰胺衍生物、其制备中的中间体和农业/园艺杀虫剂及其使用方法

Country Status (16)

Country Link
US (1) US6875768B1 (zh)
EP (1) EP1193254A4 (zh)
JP (1) JP5311072B2 (zh)
KR (1) KR100429276B1 (zh)
CN (1) CN1195734C (zh)
AR (1) AR030154A1 (zh)
AU (1) AU773377B2 (zh)
BR (1) BR0012224B1 (zh)
CO (1) CO5221024A1 (zh)
CZ (1) CZ200239A3 (zh)
EG (1) EG22172A (zh)
HU (1) HUP0202190A3 (zh)
IL (1) IL147228A0 (zh)
PL (1) PL353389A1 (zh)
TR (1) TR200200210T2 (zh)
WO (1) WO2001002354A1 (zh)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
JP2004515547A (ja) * 2000-12-11 2004-05-27 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 置換複素環式フタル酸ジアミド殺節足動物剤
DE10133665A1 (de) * 2001-07-11 2003-01-30 Boehringer Ingelheim Pharma Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung
MY142967A (en) 2001-08-13 2011-01-31 Du Pont Method for controlling particular insect pests by applying anthranilamide compounds
AR036872A1 (es) 2001-08-13 2004-10-13 Du Pont Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados
CN1865258A (zh) 2001-08-15 2006-11-22 纳幕尔杜邦公司 用于控制无脊椎害虫的邻位取代的芳基酰胺化合物
EP1417204B1 (en) 2001-08-15 2006-01-18 E. I. du Pont de Nemours and Company Ortho-heterocyclic substituted aryl amides for controlling invertebrate pests
WO2003016284A1 (en) 2001-08-16 2003-02-27 E. I. Du Pont De Nemours And Company Substituted anthranilamides for controlling invertebrate pests
BR0212695A (pt) 2001-09-21 2004-10-19 Du Pont Composto, composição artropodicida e método para o controle de artrópodes
TW200724033A (en) 2001-09-21 2007-07-01 Du Pont Anthranilamide arthropodicide treatment
ES2319972T3 (es) 2001-10-15 2009-05-18 E.I. Du Pont De Nemours And Company Iminobenzoxazinas, iminobenzotiazinas e iminoquinazolinas para controlar plagas de invertebrados.
US7205307B2 (en) * 2002-02-14 2007-04-17 Icagen, Inc. Pyrimidines as novel openers of potassium ion channels
BR0309767A (pt) * 2002-05-02 2005-02-22 Bayer Cropscience Ag Derivado de ftalamida, inseticida agrìcola ou hortìcola, e método de uso deste
JP2004018506A (ja) * 2002-06-20 2004-01-22 Bayer Ag 殺虫性フタラミド誘導体
DE10330723A1 (de) * 2003-07-08 2005-02-03 Bayer Cropscience Ag Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
DE10330724A1 (de) 2003-07-08 2005-01-27 Bayer Cropscience Ag Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
JP2006076990A (ja) 2004-03-12 2006-03-23 Bayer Cropscience Ag 殺虫性ベンゼンジカルボキサミド類
DE102004035134A1 (de) * 2004-07-20 2006-02-16 Bayer Cropscience Ag Selektive Insektizide auf Basis von Halogenalkylnicotinsäurederivaten, Anthranilsäureamiden oder Phthalsäurediamiden und Safenern
US20080051457A1 (en) * 2004-08-23 2008-02-28 Hayami Nakao Optically Active Phthalamide Derivative, Agricultural or Horticultural Insecticide, and Method of Using the Same
US20080045727A1 (en) * 2004-08-31 2008-02-21 Harry Blaschke Chiral 3-Halophthalic Acid Derivatives
DE102004055582A1 (de) 2004-11-18 2006-05-24 Bayer Cropscience Ag N-Heterocyclyl-phthalsäurediamide
KR20080018891A (ko) * 2005-05-19 2008-02-28 바이엘 크롭사이언스 아게 살충성을 가지는 치환된 벤질아미노 헤테로사이클릭 및헤테로아릴 유도체
US7574570B2 (en) * 2005-09-30 2009-08-11 Cleversafe Inc Billing system for information dispersal system
DE102005059466A1 (de) * 2005-12-13 2007-06-14 Bayer Cropscience Ag Insektizide Zusammensetzungen mit verbesserter Wirkung
DE102006016641A1 (de) * 2006-04-08 2007-10-11 Bayer Cropscience Ag Verwendung von 3-(2,4,6-Trimethylphenyl)-4-neopentylcarbonyloxy-5,5-tetramethylen-Δ3-dihydrofuran-2-on zur Bekämpfung von Dipteren aus der Familie der Cecidomyiidae
CN101522024A (zh) * 2006-09-30 2009-09-02 拜尔农作物科学股份公司 施用于栽培基质时农化组合物的生物学作用改善、合适的制剂及其用途
JP5238172B2 (ja) * 2007-03-22 2013-07-17 公益財団法人相模中央化学研究所 パーフルオロアルキル基を有する含窒素六員環化合物およびその製造方法
AU2012259335B2 (en) * 2011-05-23 2017-03-16 Merck Patent Gmbh Thiazole derivatives
JP2015027951A (ja) * 2011-11-02 2015-02-12 日本農薬株式会社 フタルアミド誘導体及び該誘導体を含有する農園芸用殺虫剤並びにその使用方法
EP2871179A4 (en) 2012-07-03 2016-03-16 Ono Pharmaceutical Co CONNECTION WITH AGONISTIC EFFECT ON THE SOMATOSTATIN RECEPTOR AND ITS USE FOR MEDICAL PURPOSES
WO2017144402A1 (de) * 2016-02-24 2017-08-31 Bayer Cropscience Aktiengesellschaft N-(5-halogen-1,3,4-oxadiazol-2-yl)arylcarbonsäureamide und ihre verwendung als herbizide

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4173639A (en) * 1978-08-31 1979-11-06 Eli Lilly And Company 1-Benzoyl-3-(alkoxy- or alkylthiopyridinyl)ureas
CA1128044A (en) * 1978-08-31 1982-07-20 Robert G. Suhr 1-benzoyl-3-(aryloxy-or arylthiopyridinyl) ureas compounds
DE3305569A1 (de) * 1983-02-18 1984-08-23 Bayer Ag, 5090 Leverkusen Biscarboxamide zur bekaempfung von erkrankungen sowie verfahren zu ihrer herstellung
PH21918A (en) * 1983-07-25 1988-04-08 Ciba Geigy Ag N-(2-nitrophenyl)-5-aminopyrimidine derivatives,the preparation and use thereof
US4694016A (en) * 1985-10-18 1987-09-15 International Minerals & Chemical Corp. Phthalamide derivatives with anthelmintic activity
JP3253727B2 (ja) * 1992-01-30 2002-02-04 中外製薬株式会社 新規なトリアゾール誘導体
JP3235317B2 (ja) * 1993-12-28 2001-12-04 日本メクトロン株式会社 新規ピリミジン誘導体類およびそれらの製造法
AUPO709497A0 (en) * 1997-05-30 1997-06-26 Commonwealth Scientific And Industrial Research Organisation Terminal connection to double layer capacitors
TW515786B (en) 1997-11-25 2003-01-01 Nihon Nohyaku Co Ltd Phthalic acid diamide derivatives, agricultural and horticultural insecticides, and a method for application of the insecticides
GB9823871D0 (en) * 1998-10-30 1998-12-23 Pharmacia & Upjohn Spa 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents
CZ299375B6 (cs) 1998-11-30 2008-07-09 Nihon Nohyaku Co., Ltd. Ftalamidové deriváty nebo jejich soli, zemedelsko-zahradnický insekticid je obsahující a jeho použití

Also Published As

Publication number Publication date
HUP0202190A3 (en) 2003-01-28
PL353389A1 (en) 2003-11-17
CO5221024A1 (es) 2002-11-28
AU5709300A (en) 2001-01-22
HUP0202190A2 (en) 2002-09-28
AU773377B2 (en) 2004-05-20
KR100429276B1 (ko) 2004-04-29
TR200200210T2 (tr) 2002-06-21
EP1193254A4 (en) 2007-09-19
CZ200239A3 (cs) 2002-05-15
EG22172A (en) 2002-10-31
BR0012224B1 (pt) 2010-12-28
CN1360573A (zh) 2002-07-24
JP5311072B2 (ja) 2013-10-09
EP1193254A1 (en) 2002-04-03
IL147228A0 (en) 2002-08-14
BR0012224A (pt) 2002-05-28
KR20020063154A (ko) 2002-08-01
US6875768B1 (en) 2005-04-05
AR030154A1 (es) 2003-08-13
JP2011074077A (ja) 2011-04-14
WO2001002354A1 (fr) 2001-01-11

Similar Documents

Publication Publication Date Title
CN1195734C (zh) 邻苯二甲酰胺衍生物、其制备中的中间体和农业/园艺杀虫剂及其使用方法
CN1068584C (zh) 邻苯二甲酰胺衍生物、农用和园艺用杀虫剂和施用这些杀虫剂的方法
CN1294121C (zh) 取代的酰基苯胺衍生物、其中间体、农业与园艺化学品及其用途
CN1249020C (zh) 芳族二酰胺衍生物、农业与园艺化学药品及其用途
CN1046275C (zh) 2－甲氧亚氨基苯基-n-甲基乙酰胺衍生物、其制备方法和用途及含有它的组合物
CN1423632A (zh) 芳族二酰胺衍生物或其盐、农艺组合物及其使用方法
CN1028143C (zh) 噁唑烷酮杀菌组合物
CN1255491A (zh) 邻苯二酰胺衍生物或其盐,农业园艺用杀虫剂及其使用方法
CN1871209A (zh) 农园艺用杀虫剂及其使用方法
CN1910156A (zh) 作为杀虫剂的丙二腈化合物
CN1026698C (zh) 3-(取代苯基)吡唑衍生物及其盐的制备方法
CN101039922A (zh) 3－***基苯基硫醚衍生物及含其作为有效成分的杀虫·杀螨·杀线虫剂
CN1358173A (zh) 杂环二羧酸二酰胺衍生物,农业和园艺杀虫剂以及使用它们的方法
CN1112556A (zh) 呋喃基杀虫剂
CN1087342A (zh) 新的取代的吡唑衍生物及其制备方法和作为除草剂的应用
CN1509268A (zh) 取代的芳族酰胺衍生物、它们的中间体、含有它们的农艺杀虫剂和它们的使用方法
CN1231663A (zh) 杀节肢动物剂和杀真菌剂环酰胺
CN1028476C (zh) 含有尿嘧啶衍生物的除草剂组合物
CN1142152C (zh) 苯甲酰胺衍生物、农业与园艺用杀虫剂及其用途
CN1282331A (zh) 除草的3－(吲哚－4－基)嘧啶二酮衍生物
JP2001335563A (ja) フタラミド誘導体、その中間体及び農園芸用殺虫剤並びにその使用方法
CN1113232A (zh) 二硫代碳酰亚胺衍生物，其中间体、制备方法和用途
CN1016661B (zh) 含吡啶磺酰胺的除草组合物
CN1045590C (zh) 肼衍生物和含有它的农业和园艺杀虫剂组合物
CN1251575A (zh) 肟醚化合物,其用途和制备肟醚化合物的中间体

Legal Events

Date Code Title Description
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C06 Publication
PB01 Publication
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20050406

Termination date: 20150704

EXPY Termination of patent right or utility model