CN1234177A - 氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途 - Google Patents

氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途 Download PDF

Info

Publication number
CN1234177A
CN1234177A CN99105289A CN99105289A CN1234177A CN 1234177 A CN1234177 A CN 1234177A CN 99105289 A CN99105289 A CN 99105289A CN 99105289 A CN99105289 A CN 99105289A CN 1234177 A CN1234177 A CN 1234177A
Authority
CN
China
Prior art keywords
halo
alkyl
group
alkoxyl
different
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.)
Granted
Application number
CN99105289A
Other languages
English (en)
Other versions
CN1132516C (zh
Inventor
安藤亘治
三瓶修
坂田和之
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 CN1234177A publication Critical patent/CN1234177A/zh
Application granted granted Critical
Publication of CN1132516C publication Critical patent/CN1132516C/zh
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/26—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups, amino groups and singly-bound oxygen atoms bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C317/50—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

式(Ⅰ)所示的氨基乙腈衍生物,其中Ar1和Ar2表示苯基;具有至少一个取代基的取代苯基,其取代基如说明书中所述,(取代)吡啶基和(取代)萘基,Q表示－C(R1)(R2)－(其中R1和R2如说明书中所定义);－CH=CH－或－C≡C－,d是0或整数1,R3表示氢原子、(卤代)C1－C6烷基,R4、R5、R6、R7和R8表示氢原子、卤原子、(卤代)C1－C6烷基,W是－O－、－S－、－SO2－或－N(R9)－(其中R9是氢原子或C1－C6烷基),以及a和b是0或1—4的整数),含有所述衍生物作为活性成分的农业和园艺杀虫剂,以及该杀虫剂的使用方法。

Description

氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途
本发明涉及式(Ⅰ)所示的氨基乙腈衍生物和含有所述衍生物作为活性成分的农业和园艺杀虫剂。本发明也涉及使用该杀虫剂的方法。
日本专利申请公开特开平9-48750(1997)公开了作为农业和园艺杀菌剂的苯基链烷酸酰氨衍生物，日本专利申请公开特开平6-220004(1994)公开了作为产物中间体的N-苯基乙酰氨基腈，以及日本专利申请公开特开平6-263731(1994)、特开平6-271537(1994)和特开平7-252222(1995)公开了与本发明类似的式(Ⅰ)所示氨基乙腈衍生物。
为了开发新农业和园艺杀虫剂，本发明人进行了广泛的研究，结果发现式(Ⅰ)所示的氨基乙腈衍生物是一种新化合物并且具有显著的杀虫效果，以此完成了本发明。
本发明涉及式(Ⅰ)所示的氨基乙腈衍生物和含有所述衍生物体作为活性成分的农业和园艺杀虫剂：
Figure A9910528900111
(其中Ar1和Ar2可以相同或者不同，各表示苯基；
具有至少一个取代基的取代苯基，其取代基可以相同或者不同并选自下列取代基：
卤原子，硝基，氰基，
C1-C6烷基，卤代C1-C6烷基，
C1-C6烷氧基，卤代C1-C6烷氧基，
C2-C6链烯基，卤代C2-C6链烯基，
C2-C6炔基，C3-C6环烷基，
C2-C6链烯氧基，卤代C2-C6链烯氧基，
C1-C6烷硫基，卤代C1-C6烷硫基，
C1-C6烷基磺酰氧基，
卤代C1-C6烷基磺酰氧基，
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，
C2-C6链烯硫基，
卤代C2-C6链烯硫基，
C2-C6链烯基亚磺酰基，
卤代C2-C6链烯基亚磺酰基，
C2-C6链烯基磺酰基，
卤代C2-C6链烯基磺酰基，
C1-C6烷基氨基、二-C1-C6烷基氨基，
C1-C6烷基磺酰氨基，卤代C1-C6烷基磺酰氨基，
C1-C6烷基羰基，
卤代C1-C6烷基羰基，
C1-C6烷氧羰基，
苯基，
至少具有一个取代基的取代苯基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、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，
苯氧基，
在其环上具有至少一个取代基的取代苯氧基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、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，
苯乙炔基，
在其环上具有至少一个取代基的取代苯乙炔基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、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，
吡啶氧基和
在其环上具有至少一个取代基的取代吡啶氧基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、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；
吡啶基；
在其环上具有至少一个取代基的取代吡啶基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C2-C6链烯氧基、卤代C2-C6链烯氧基、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、C2-C6链烯硫基、卤代C2-C6链烯硫基、C2-C6链烯基亚磺酰基、卤代C2-C6链烯基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C2-C6链烯基磺酰基、卤代C2-C6链烯基磺酰基、C1-C6烷基氨基和二-C1-C6烷基氨基；
萘基；或
在其环上具有至少一个取代基的萘基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C2-C6链烯氧基、卤代C2-C6链烯氧基、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、C2-C6链烯硫基、卤代C2-C6链烯硫基、C2-C6链烯基亚磺酰基、卤代C2-C6链烯基亚磺酰基、C2-C6链烯基磺酰基、卤代C2-C6链烯基磺酰基、C1-C6烷基氨基和二-C1-C6烷基氨基；
Q表示基团(其中R1和R2可以相同或者不同，各表示氢原子，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，C3-C6环烷基或具有至少一个取代基的取代C3-C6环烷基，其取代基可以相同或者不同并选自卤原子和C1-C6烷基，并且R1和R2可以连在一起表示在其链上可具有至少一个取代基的C2-C6亚烷基，所述取代基选自卤原子、C1-C6烷基或C1-C6烷氧基)，-CH=CH-或-C≡C-；d是0或者整数1；
R3表示氢原子、C1-C6烷基、卤代C1-C6烷基、氰基C1-C6烷基、C1-C6烷硫基、卤代C1-C6烷硫基、C2-C6链烯基或C2-C6炔基；
R4、R5、R6、R7和R8可以相同或者不同并且各表示氢原子，卤原子，C1-C6烷基，卤代C1-C6烷基，C3-C6环烷基或具有至少一个取代基的取代C3-C6环烷基，所述取代基可以相同或者不同并选自卤原子和C1-C6烷基，苯基或具有至少一个取代基的取代苯基，所述取代基可以相同或者不同并选自卤原子、硝基、氰基、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、C1-C6烷基氨基和二-C1-C6烷基氨基，并且R4和R5一起可以形成C1-C6亚烷基；
W是-O-、-S-、-SO2-、或-N(R9)-(其中R9表示氢原子或C1-C6烷基)，及
a和b可以相同或者不同，表示0或1-4的整数))。
在本发明中，式(Ⅰ)所示氨基乙腈衍生物的优选取代基包括，例如，作为取代基Ar1和Ar2的苯基，作为Ar1和Ar2环上取代基的卤原子、卤代C1-C6烷基和卤代C1-C6烷氧基，作为取代基R1、R2、R3、R5和R6的氢原子，作为取代基R4的C1-C6烷基，作为取代基Q的-CH2-，作为取代基W的-O-，及a优选为整数1,b优选为0。
本发明式(Ⅰ)所示的氨基乙腈衍生物包括具有立体异构体的化合物，本发明也包括这些立体异构体。
本发明式(Ⅰ)所示的氨基乙腈衍生物例如可以通过下面的制备方法制备。其中R3、R4、R5、R6、R7、R8、Ar1、Ar2、Q、W、a、b和d的定义同上，M表示碱金属原子，Hal表示卤原子。)1．式(Ⅳ )→式(Ⅰ)
式(Ⅰ)所示的氨基乙腈衍生物，可以在碱(例如，三乙胺、吡啶等)的存在下，通过式(Ⅳ)所示的氨基乙腈衍生物与式(Ⅲ)所示的酰基卤反应制备。式(Ⅰ)所示的氨基乙腈衍生物，也可以使用缩合剂(例如，二环己基碳化二亚胺、碘化2-氯-1-甲基吡啶鎓等)，通过式(Ⅳ)所示的氨基乙腈化合物与式(Ⅱ)所示的酸的缩合反应制备。式(Ⅱ)所示的酸可以通过已知方法制备(例如，有机化学杂志(J.Org.Chem.)763,1948，有机合成(累积)(Organic SynthesisColl.)，第1卷，436，有机化学杂志(J.Org.Chem.)763,1948，有机合成(累积)(Organic Synthesis Coll.)，第1卷，336，拜尔斯坦手册(Beilsteins Handbuch)9,573，拜尔斯坦手册(Beilsteins Handbuch)9,633等)。2．式(Ⅷ)→式(Ⅳ)
制备式(Ⅳ)所示的氨基乙腈衍生物，例如，可以通过式(Ⅶ)所示的羰基化合物与式(Ⅵ)所示的金属氰化物(例如，***、***等)和式(Ⅴ)所示的胺反应。可以使用有机氰化物如三甲硅烷基腈和丙酮合氰化氢作为CN来源。这些反应被称为Strecker反应(例如，C-C键的形成(Formation of C-C Bonds)第1卷，Georg Thieme出版公司，1973年，有机合成(累积)(Organic Synthesis Coll.)，第3卷，88等)。
制备式(Ⅶ)所示的羰基化合物，也可以使用(例如)下面的制备方法。
Figure A9910528900161
其中R3、R4、R5、R6、R7、R8、Ar1、Ar2、a和b的定义同上，L表示离去基团如卤原子、甲磺酰氧基或对甲苯磺酰氧基，W’是OH、SH或NHR9(其中R9的定义同上，Rs是相同或不同的C1-C6烷基及表示C1-C4亚烷基，或者Rs一起形成C1-C4亚烷基。
制备式(Ⅷ)所示的羰基化合物，例如，可在碱的存在下，用具有离去基团L的式(Ⅷ-1)所示化合物与式(Ⅸ-1)所示化合物反应。
类似地，也可以通过式(Ⅷ-2)所示化合物与式(Ⅸ-2)所示化合物反应来制备制备式(Ⅶ)所示的羰基化合物。
而且，式(Ⅷ)所示的羰基化合物也可以在酸性条件下通过式(Ⅻ)所示化合物的去保护反应制备，式(Ⅻ)所示化合物是用式(Ⅹ-1)所示化合物(其羰基以缩醛、缩酮等形式被保护起来)与式(Ⅸ-1)所示化合物反应得到的。类似地，式(Ⅻ)所示化合物可以通过式(Ⅹ-2)所示化合物与式(Ⅸ-2)所示化合物反应来制备。此外，式(Ⅶ)所示羰基化合物可以通过使用合适的氧化剂(例如，高锰酸钾等)氧化式(ⅩⅢ)所示化合物来制备，式(ⅩⅢ)所示化合物是通过式(Ⅺ-1)所示醇化合物与式(Ⅸ-1)所示化合物反应得到的。类似地，式(ⅩⅢ)所示化合物可以通过式(Ⅺ-2)所示醇化合物与式(Ⅸ-2)所示化合物反应制备的。
本发明式(Ⅰ)所示氨基乙腈衍生物的典型化合物如表1、2和3中所示。式(Ⅰ)
Figure A9910528900181
表1(R6=R7=R8=H,Q=-C(R1)(R2)-,d=1,b=0(另有描述的除外)
    No.  Ar1  Ar2  R1 R2 R3  R4  R5  W  a
    12345678910111213141516171819  PhPhPhPhPhPhPhPhPh2-Cl-Ph2-Cl-Ph2-Cl-Ph2-Cl-Ph2-Cl-Ph2-Cl-Ph2-C1-Ph2-Cl-Ph2-Cl-Ph2-Cl-Ph  Ph4-Cl-Ph4-Cl-Ph4-CF3-Ph4-CHF2O-Ph4-CF3O-Ph4-CF3S-Ph4-CF-3SO2-Ph4-Cl-Ph2-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph     (CH2)2  HHHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3HCH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHCH3CH3n-C3H7n-C3H7n-C4H9n-C4H9  00000000000  11111111142
H H
    (CH2)2
 HHHHHCH3OHHHHHHHHHH  HHHHHHHHHHHHHHHH
    b=1
 00000000  11111111
表1(续)表1(续)
    No.    Ar1    Ar2    R1    R2  R3  R4  R5     W     a
    42434445464748495051525354555657585960616263  2-F-ph2-F-Ph3-Cl-Ph3-Cl-Ph3-Cl-Ph3-Cl-ph3-Cl-Ph3-Cl-Ph3-Cl-Ph3-Cl-Ph3-Cl-Ph3-Cl-Ph3-Cl-Ph3-Cl-Ph3-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph  4-Cl-Ph4-CF3-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-PhPhPhPh2-Cl-Ph2-Cl-Ph3-Cl-Ph4-Cl-Ph      (CH2)2  HHHHHHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3C2H5CH3CH3n-C3H7i-C3H7c-C3H5t-C4H9  HHCH3CH3n-C3H7n-C3H7HHHHHHH     0000000000000000SSO20000     1111111141111111111411
    HHHHHHHHHHHHH     HHHHHHHHHHHHH
          (CH2)4
     (CH2)2
 CH3CH3CH3CH3CH3CH3CH3H  HHHHHHHH
    HHHHHHH     HHHHHHH
表1(续)
Figure A9910528900221
表1(续)
    No.    Ar1    Ar2       R1  R2  R3  R4  R5  W  a
    858687888990919293949596979899100101102103104105  4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph  4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-I-Ph4-Br-Ph4-F-Ph3-CF3-Ph4-CF3-Ph4-C2F5-Ph4-i-C3F7-Ph4-CF3-Ph4-n-C3F7-Ph4-CH3-Ph4-t-C4H9-Ph4-(t-C4H9-C≡C)-Ph4-CH3O-ph4-CF3O-Ph     i-C3H7i-C3H7CF3  HHH  HHHHHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHHHHHHH  000000000000000000000  111111111111111111111
    (CH3)2
    (CH2)3
    (CH2)4
    FHHHHHHH  FHHHHHHH
    (CH2)2
    HHHHHH  HHHHHH
表1(续)
    No.    Ar1      Ar2  R1 R2 R3  R4  R5  W  a
    106107108109110111112113114115116117118119120121122123124125126  4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-C1-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph  4-CHF2O-Ph4-CF3SO2-Ph4-CH3S-Ph4-CH3SO2-Ph4-CF3S-Ph4-CF3SO2-Ph4-CHF2S-Ph4-CHF2SO2-Ph4-n-C3F7S-Ph4-i-C3F7S-Ph4-n-C3F7SO2-Ph4-n-C6F13S-Ph4-n-C6F13SO2-Ph4-CF3SO2NH-Ph4-(5-CF3-2-Pyr)O-Ph2,4-Cl2-Ph3,4-Cl2-Ph3-C1-4-F-Ph3-CF3-4-NO2-Ph3,5-(CH3)2-Ph2,3,4,5,6-F5-Ph  HHHHHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHHHHHHH  000000000000000000000  111111111111111111111
表1(续)
    No.       Ar1      Ar2  R1  R2  R3  R4  R5     W     a
    127128129130131132133134135136137138139140141142143144     4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-F-Ph4-F-Ph4-F-Ph4-F-Ph  4-(Cl2C=CH-CH2O)-Ph4-(Cl2C=CH-CH2S)-Ph4-(Cl2C=CH-CH2SO2)-Ph2,6-Cl2-4-(Cl2-C=CHCH2O)-Ph4-CN-Ph4-NO2-Ph4-(Ph-C≡C)Ph2-Naph6-Cl-2-Naph6-CF3-2-Naph5-Cl-2-Pyr6-Cl-3-Pyr5-NO2-2-Pyr5-CN-2-Pyr4-Cl-Ph4-Cl-Ph4-F-Ph4-I-Ph  HHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHHHH     000000000000000N-CH300     111111111111111111
表1(续)
    No.    Ar1      Ar2 R1 R2 R3  R4 R5     W  a
    145146147148149150151152153154155156157158159160161  4-F-Ph4-F-Ph4-F-Ph4-F-Ph4-F-Ph4-F-Ph4-F-Ph4-F-Ph4-Br-Ph2-I-Ph4-I-Ph4-I-Ph4-I-Ph2-CH3-Ph2-CH3-Ph3-CH3-Ph4-CH3-Ph  4-i-C3H7-Ph4-CF3O-Ph4-CF3-Ph4-CN-Ph4-NO2-Ph3-Cl-4-F-ph2,3,4,5,6-F5-Ph6-Cl-2-Pyr4-Cl-Ph4-CF3-Ph4-Cl-Ph4-I-Ph4-CF3-Ph3,5-(CH3)2-Ph4-CF3-Ph3,5-(CH3)2-Ph3,5-(CH3)2-Ph  HHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHHH     00000000000000000  11111111111111111
表1(续)
    No.        Ar1      Ar2  R1  R2  R3  R4  R5  W  a
    162163164165166167168169170171172173174175176177178179180     2-CH3O-Ph3-CF3-Ph4-CH3O-Ph4-CH3O-Ph4-CH3O-Ph4-CH3O-Ph4-CH3O-Ph4-CH3O-Ph4-CH3O-Ph4-CH3O-Ph4-CH3O-ph4-CH3O-Ph4-CH3O-Ph4-CH3O-Ph4-CH3O-Ph4-CF3O-Ph4-CHF2O-Ph4-CF3SO2O-Ph4-CHF2S-Ph  3,5-(CH3)2-Ph4-Cl-Ph3,5-(CH3)2-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-ph4-Cl-Ph4-Cl-Ph4-Cl-Ph  HHHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3C2H5n-C3H7i-C3H7c-C3H5t-C4H9  HHHHCH3n-C3H7n-C3H7n-C4H9HHHHHH  0000000000000000000  1111111141111111111
           (CH2)4
 CH3CH3CH3CH3  HHHH
表1(续)
    No.      Ar1    Ar2 R1 R2 R3  R4  R5  W  a
    181182183184185186187188189190191192193194195196197198199200201  4-CHF2SO2-Ph4-CF3S-Ph4-CF3SO2-Ph4-n-C3F7-Ph4-CF3SO2NH-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph  4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph2-Cl-Ph4-Cl-Ph4-F-Ph4-I-Ph2,4-Cl2-Ph2,4-F2-Ph2,6-F2-Ph4-I-2-CH3-Ph4-CH3-Ph4-CF3-Ph4-C2F5-Ph4-n-C3F7-Ph4-i-C3F7-Ph4-(PhO)-Ph4-CF3O-Ph4-CHF2O-Ph  HHHHHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHHHHHHH  000000000000000000000  111111111111111111111
表1(续)
    No.    Ar1      Ar2  R1  R2  R3  R4  R5  W  a
    202203204205206207208209210211212213214215216217  4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph  4-CF3SO2O-Ph4-CF3S-Ph4-CF3SO2-Ph4-CHF2S-Ph4-CHF2SO2-Ph4-n-C3F7S-Ph4-i-C3F7S-Ph4-n-C3F7SO2-Ph4-n-C6F13S-Ph4-n-C6F13SO2-Ph4-CF3SO2NH-Ph4-COOCH3-Ph2-(Cl2C=CH-CH2O)-Ph4-(Cl2C=CH-CH2S)-Ph4-(Cl2C=CH-CH2SO2)-Ph2,6-Cl2-4-(Cl2-C=CHCH2O)-Ph  HHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHH  0000000000000000  1111111111111111
表1(续)
    No.     Ar1     Ar2     R1  R2  R3  R4  R5  W  a
    218219220221222223224225226227228229230231232233234235236237  4-CF3-Ph4-CF3-Ph4-C2F5-Ph4-C2F5-Ph4-C2F5-Ph4-n-C3F7-Ph4-n-C3F7-Ph4-n-C3F7-Ph4-i-C3F7-Ph4-i-C3F7-Ph4-i-C3F7-Ph4-NO2-Ph4-Ph-Ph2,4-Cl2-Ph2,4-Cl2-Ph2,4-Cl2-Ph2,6-Cl2-Ph2,6-F2-Ph2,6-F2-Ph3,4-F2-Ph  4-(t-C4H9C≡C)-Ph4-(Ph-C≡C)-Ph4-Cl-Ph4-CF3-Ph4-i-C3F7-Ph4-Cl-Ph4-CF3-Ph4-i-C3F7-Ph4-Cl-Ph4-CF3-Ph4-i-C3F7-Ph4-F-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-CF3-Ph4-Cl-Ph4-Cl-Ph4-CF3-Ph4-F-Ph     HHHHHHHHHHHHHHCH3OHHHHH  HHHHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHHHHHH  00000000000000000000  11111111111111111111
表1(续)
    No.      Ar1      Ar2  R1  R2  R3  R4  R5  W  a
    238239240241242243244245246247248249250251252253254255  3,4-F2-Ph2,3-(CH3)2-Ph3,5-(CH3)2-Ph3,5-(CH3)2-Ph3,5-(CH3)2-Ph3,5-(CF3)2-ph2,4,6-(CH3)3-Ph2,3,4,5,6-F5-Ph5-Cl-2-Pyr5-Cl-2-Pyr5-Cl-2-Pyr5-Cl-2-Pyr6-Cl-3-Pyr6-Cl-3-Pyr5-CF3-2-Pyr5-CF3-2-Pyr5-CF3-2-Pyr5-CF3-2-Pyr  4-CF3-Ph3,5-(CH3)2-Ph4-CH3-Ph4-OCH3-Ph2,3-(CH3)2-Ph4-CF3-Ph4-Cl-Ph4-F-Ph4-Cl-Ph4-CF3-Ph5-Cl-2-Pyr5-CF3-2-Pyr4-Cl-Ph4-CF3-Ph4-Cl-Ph4-CF3-Ph4-Cl-2-Pyr4-CF3-2-Pyr  HHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHHHH  000000000000000000  111111111111111111
表1(续)
    No.         Ar1        Ar2     R1  R2  R3  R4  R5  W     a
    256257258259260261262263264265266267268269270271272273274275276277     6-CF3-3-Pyr6-CF3-3-Pyr5-CN-2-Pyr5-NO2-2-Pyr5-CF3O-2-Pyr5-CF3O-2-Pyr5-CF3S-2-Pyr5-CF3S-2-Pyr5-CF3SO2-2-pyr5-CF3SO2-2-Pyr3,5-Cl2-2-Pyr3,5-Cl2-2-Pyr5-CF3-3-Cl-2-Pyr5-CF3-3-Cl-2-Pyr2-Naph6-Cl-2-Naph6-Cl-2-Naph6-CF3-2-Naph6-CF3-2-Naph6-CF3O-2-Naph6-CF3S-2-Naph6-CF3SO2-2-Naph     4-Cl-Ph4-CF3-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-CF3-Ph4-Cl-Ph4-CF3-Ph4-Cl-Ph4-CF3-Ph4-Cl-ph4-CF3-Ph4-Cl-Ph4-CF3-ph4-Cl-Ph4-Cl-Ph4-CF3-Ph4-Cl-Ph4-CF3-Ph4-Cl-ph4-Cl-Ph4-Cl-Ph     HHHHHHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHHHHHH  HHHHHHHHHHHHHHHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHHHHHHHH  0000000000000000000000     1111111111111111l11111
表1(续)
    No.    Ar1    Ar2 R1 R2 R3  R4 R5  W  a
    278279280281282283284285286  4-CF3-Ph4-Cl-Ph4-Cl-Ph4-CF3-Ph4-CF3O-Ph2-F-4-Cl-Ph2-Cl-4-F-Ph2,4-F2-Ph4-(PhC≡C)Ph  4-Cl-Ph4-Cl-PhPhPh4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-Cl-Ph  HHHHHHHHH  HHHHHHHHH  HHHHHHHHH  CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHH  0  1
    b=1
 0  1
    b=1
 0  1
   R7=CH3,b=1
 H  0  1
   R7=CH3,b=1
 HHHHH  00000  11111
表2(R6=R7=R8=H,b=0)
    No.  Ar1   Ar2     (Q)d R3   R4  R5  W  a
    287288289290291  PhPhPh4-Cl-Ph4-Cl-Ph  4-Cl-Ph4-Cl-Ph4-CF3O-Ph4-Cl-Ph4-CF3-Ph     CH=CHC≡CC≡CCH=CHC≡C  HHHHH  CH3CH3CH3CH3CH3  HHHHH  00000  11111
表3(R6=R7=R8=H,b=0,d=0)
    No.    Ar1    Ar2  R3  R4  R5  W  a
    292293294295296297298299300  4-Cl-Ph4-CF3-Ph3-CF3-Ph2-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph  Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph4-Cl-Ph2-Cl-Ph  HHHHHHHHH  CH3CH3CH3CH3C2H5Ht-C4H9  HHHHHHH  000000000  111111114
     (CH2)4
 CH3  H
表3(续)
    No.    Ar1          Ar2 R3     R4 R5  W  a
    301302303304305306307308309310311312313314315316317  4-Cl-Ph4-CF3-Ph4-CF3-Ph3,5-(CH3)2-Ph4-CF3-Ph4-CF3O-Ph3-CF3O-Ph4-CF3-Ph4-F-Ph2,4-Cl2-Ph4-I-Ph4-NO2-Ph4-C2F5-Ph4-CF3-Ph4-CH3O-Ph4-CN-Ph2,6-Cl2-Ph  2,6-Cl2-4-(Cl2C=CHCH2O)-Ph4-(t-C4H9C≡C)-Ph4-(PhC≡C)-Ph4-Cl-Ph4-Cl-Ph4-CF3-Ph4-CF3-PhPh4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3O-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph  HHHHHHHHHHHHHHHHH     CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHH  00000000  11111b=1111
 R7=CH3,b=1
 HHHHHHHHH  000000000  111111111
表3(续)
    No.     Ar1     Ar2  R3     R4 R5  W  a
    318319320321322323324325326327328329330331332333334335336337338339  3,5-Cl2-Ph2-Cl-Ph3-Cl-Ph4-Cl-Ph2-Cl-4-NO2-Ph3-CH3O-Ph3,4-Cl2-Ph2-Cl-4-F-Ph4-CF3-Ph2,5-Cl2-Ph4-CF3S-Ph2-CH3-Ph3-CH3-Ph4-CH3-Ph2-CH3O-Ph2,4-F2-Ph5,6-Cl2-3-Pyr5,6-Cl2-3-Pyr2-Cl-3-Pyr6-Cl-3-Pyr2-Naph4-COOCH3-Ph  4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-Cl-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph  HHHHHHHHCH3HHHHHHHHHHHHH     CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3  HHHHHHHHHHHHHHHHHHHHHH  0000000000000000000000  1111111111111111111111
表3(续)
    No.     Ar1     Ar2  R3     R4     R5  W  a
    340341342343344345346347348349350351352353354355356357  3-Pyr2-Cl-6-CH3-3-Pyr2,6-Cl2-4-Pyr4-t-C4H9-Ph4-n-C4H9-Ph4-(CH3)2N-Ph4-CH3COO-Ph4-CN-Ph2-CHF2S-3-Pyr6-CHF2O-3-Pyr2-F-4-CF3-Ph4-CF3CONH-Ph4-(3-Cl-5-CF3-2-Pyr)O-Ph2,4-Cl2-Ph2,4-Cl2-Ph4-CN-Ph2,4-Cl2-Ph4-CN-Ph  4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph  HHHHHHHHHHHHHHHHHH     CH3CH3CH3CH3CH3CH3CH3t-C4H9CH3CH3CH3CH3CH3t-C4H9i-C3H7i-C3H7CH3CH3     HHHHHHHHHHHHHHHHCH3CH3  000000000000000000  111111111111111111
  Rf=H
表3(续)
    No.     Ar1     Ar2  R3     R4     R5  W  a
    358359360361362363364365366367368369  4-CN-Ph2-Pyr2-CH3S-3-Pyr2-CH3SO2-3-Pyr3,5-Cl2-2-Pyr3-C1-5-CF3-2-Pyr4-CF3SO2NH-Ph4-CN-Ph4-CF3SO2-Ph1-Naph4-n-C3H7S-Ph4-C2F5S-Ph  4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph4-CF3-Ph  HHHHHHHCH3HHHH     CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3    CH3HHHHHHHHHHH  0  1
   Rf=L
 00000000000  11111111111
在表1、表2和表3中，Ph表示苯基，Pyr表示吡啶基，Naph表示萘基及c-表示脂环烃。
表4显示的是表1、表2和表3中所列化合物的物理性质。表4
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    123910111213141516 m.p.101℃m.p.152℃m.p.121℃nD1.542(21℃)糊状NMR:1.65(s.3H),1.51-1.72(m.4H),1.80-2.12(m.4H),3.69(s.2H),3.95-4.03(m.2H),5.59(br.1H),6.8-6.9(m.2H),7.1-7.40(m.6H).糊状NMR:1.74(s.3H),2.06(m.2H), 3.61(m.2H),3.55-3.80(m.2H),4.28(m.2H),7.06(br.1H),7.12(d.2H),7.18-7.24(m.2H),7.25-7.40(m.4H).m.p.127-133℃m.p.138-139℃m.p.98-99℃(Rf=H)糊状(Rf=L)NMR:1.32(d.3H),1.75(s.3H),3.72(s.2H),4.60-4.70(m.1H),5.97(br.1H),6.76(d.2H),7.20-7.42(m.6H).糊状(Rf=L)NMR:0.83(t.3H),1.20-2.00(m.4H),3.66(s.2H),4.82(br.1H),5.87(br.1H),5.86(d.2H),7.15-7.30(m.6H).
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    17181920212223242526272829 糊状(Rf=H)NMR:0.89(t.3H),1.20-2.00(m.4H),3.40-3.57(m.2H),5.02(br.1H),5.70(br.1H),6.73(d.2H),7.05-7.30(m.6H).m.p.125-128℃(Rf=H)糊状(Rf=L)NMR:0.81(t.3H),1.10-1.80(m.6H),3.67(s.2H),4.75-4.82(m.1H),5.79(br.1H),6.85(d.2H),7.18-7.40(m.6H).m.p.97℃m.p.131℃m.p.107-110℃m.p.123-126℃m.p.125-126℃糊状NMR:1.08(s.9H),3.68-3.82(m.2H),4.36-4.47(m.2H),5.69(br.1H),6.75(d.2H),7.18-7.46(m.6H).m.p.78-84℃糊状NMR:1.94(s.3H),3.20(s.3H),3.83(m.2H),4.46(s.2H),6.82(d.2H),7.12-7.30(m.5H),7.37(d.1H).m.p.110-112℃m.p.118-120℃
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    3041424445464748495051 m.p.72-74℃m.p.132-133℃m.p.116-117℃m.p.134-143℃(Rf=H)糊状(Rf=L)NMR:1.31(d.3H),1.74(s.3H),3.54(s.2H),4.62-4.70(m.1H),6.12(br.1H),6.76(d.2H),7.06-7.30(m.6H).糊状(Rf=H)NMR:0.92(t.3H),1.20-2.00(m.4H),3.29(s.2H),5.02-5.12(s.1H),5.45(m.1H),6.75(d.2H),7.13-7.26(m.6H).糊状(Rf=L)NMR:0.85(t.3H),1.20-2.00(m.4H),3.49(s.2H),4.78-4.81(m.1H),5.81(br.1H),6.84(d.2H),7.15-7.30(m.6H).m.p.134-136℃m.p.103-104℃糊状NMR:1.65(s.3H),1.50-2.10(m.6H),3.54(s.2H),3.88-3.93(s.2H),5.52(br.1H),6.79(d.2H),7.10-7.30(m.6H).m.p.96-99℃
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    5253545556575859606162636465 m.p.121-122℃m.p.121-124℃糊状NMR:1.07(s.9H),3.52-3.66(m.2H),4.33-4.52(m.2H),5.55(br.1H),6.78(d.2H),7.10-7.33(m.6H).糊状NMR:1.20-2.00(m.8H),3.49(s)/3.52(s)(2H),4.35(br)/4.85(br)(1H),5.62(br)/5.95(br)(1H),6.70-6.80(m.2H),7.00-7.30(m.6H).m.p.113-114℃m.p.132-135℃m.p.142℃m.p.169℃m.p.126-127℃糊状NMR:1.64(s.3H),1.52-2.15(m.8H),3.53(s.3H),3.95-4.03(m.2H),5.59(br.1H),6.86-6.95(m.2H),7.12-7.40(m.6H).m.p.126-127℃m.p.122-128℃m.p.152℃m.p.87-89℃
表4(续)
    No. 物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    6667686970717374757677 m.p.95℃m.p.153℃糊状NMR:1.64(s.3H),1.50-2.10(m.6H),3.54(s.2H),3.87-3.93(m.2H),5.47(br.1H),6.80(d.2H),7.15-7.40(m.6H).m.p.124-141℃糊状NMR:0.85(t)/0.92(t)(3H),1.20-2.00(m.4H),3.21-3.36(m)/3.49(s)(2H),4.74-4.80(br)/5.04-5.12(br)(1H),5.41(br)/5.76(br)(1H),6.70-7.30(m.8H).m.p.124-130℃(Rf=H)m.p.126-127℃m.p.104-105℃m.p.140℃m.p.142℃糊状NMR:1.07(s.9H),3.52-3.66(m.2H),4.34-4.50(m.2H),5.57(br.1H),6.75(d.2H),7.12-7.37(m.6H).
表4(续)
    No. 物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    7980818283848586888990919294959697 糊状NMR:1.20-2.10(m.8H),3.48(s)/3.50(s)(2H),4.32(br)/4.84(br)(1H),5.60(br)/5.90(br)(1H),6.67-6.75(m.2H),7.00-7.30(m.6H).糊状NMR:1.91(s.3H),3.11(s.3H),3.70(s.2H),4.39-4.51(m.2H),6.78(d.2H),7.09(d.2H),7.22-7.26(m.4H).m.p.83-84℃m.p.57-63℃m.p.114-117℃m.p.105-108℃m.p.148-149℃(Rf=H)m.p.152-154℃(Rf=L)m.p.145-146℃m.p.123℃m.p.135-137℃m.p.96-97℃m.p.160-161℃m.p.127-130℃m.p.132-133℃m.p.120-121℃m.p.96-100℃
表4(续)
    No. 物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
     99100102103105108109114116117118120121 m.p.114-115℃m.p.126-127℃m.p.162℃m.p.159-163℃m.p.130℃m.p.85-86℃糊状NMR:1.80(s.3H),3.03(s.3H),3.58(s.2H),4.32(dd.2H),5.88(br.1H),6.96(d.2H),7.18(s.2H),7.32(d.2H),7.86(d.2H).m.p.91-92℃糊状NMR:1.81(s.3H),3.59(s.2H),4.36-4.45(m.2H),5.68(br.1H),7.03-7.10(m.2H),7.18(d.2H),7.33(d.2H),7.76(d.1H),7.99(d.1H).m.p.102-104℃糊状NMR:1.81(s.3H),3.59(s.2H),4.30-4.45(m.2H),5.66(br.1H),7.04-7.10(m.2H),7.17(d.2H),7.33(d.2H),7.75(d.1H),7.99(d.1H).m.p.160-161℃m.p.88-90℃
表4(续)
    No. 物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    122123124125126125128129130133134141142143144145146147148 m.p.125-126℃m.p.93-94℃m.p.141-142℃m.p.175-176℃nD1.511(26℃)m.p.88-89℃m.p.87-89℃糊状NMR:1.81(s.3H),3.59(s.2H),3.93(d.2H),4.35(dd.2H),5.80(br.1H),5.98(t.1H),6.98(d.2H),7.19(d.2H),7.33(d.2H),7.82(d.2H).m.p.127-128℃m.p.156-158℃m.p.146-147℃m.p.159-160℃m.p.156-157℃m.p.128-129℃m.p.144℃m.p.137-139℃m.p.107-109℃m.p.112-113℃m.p.138-140℃
表4(续)
    No. 物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    149150151152153154156157158160161163164165166167 m.p.108-110℃m.p.128-129℃m.p.108-110℃m.p.136℃m.p.146℃m.p.146-147℃m.p.142-143℃m.p.98-99℃m.p.123-124℃m.p.117-118℃m.p.110-112℃nD1.521(21℃)m.p.126-127℃m.p.115℃m.p.129-131℃糊状(Rf=H)NMR:0.91(t.3H),1.20-1.90(m.4H),3.18-3.38(m.2H),3.78(s.3H),5.04-5.12(m.1H),5.39(br.1H),6.70-6.82(m.6H),7.20(d.2H).
表4(续)
    No. 物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    168169170171172173174175 糊状(Rf=L)NBR:0.84(t.3H),1.20-1.90(m.4H),3.41-3.55(m.2H),3.79(s.3H),4.72-4.80(m.1H),5.72(br.1H),6.78-6.85(m.4H),7.05(d.2H),7.24(d.2H).m.p.121-126℃(Rf=H)糊状NMR:1.61(s.3H),1.45-2.10(m.6H),3.52(s.2H),3.78(s.3H),3.85-3.93(m.2H),5.44(br.1H),6.78(d.1H),6.87(d.2H),7.15(d.2H),7.28(d.2H).m.p.104-107℃糊状NMR:0.95(t.3H),1.35-1.55(m.2H),1.95-2.05(m.2H),3.53(s.2H),3.80(s.3H),4.19-4.33(m.2H),5.63(br.1H),6.74(d.2H),6.87(d.2H),7.11(d.2H),7.23(d.2H).m.p.114-117℃m.p.119-122℃糊状NMR:1.03(s.9H),3.49-3.64(m.2H),3.81(s.3H),4.32-4.50(m.2H),5.58(br.1H),6.77(d.2H),6.91(d.2H),7.13(d.2H),7.24(d.2H).
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    176184186187188189190191192193195196197199200207     糊状NMR:1.20-2.10(m.8H),3.43-3.55(m.2H),3.73(s)/3.87(s)(3H),4.26(br)/4.80(br)(1H),5.61(br)/5.86(br)(1H),6.65-7.25(m.8H).m.p.87-88℃m.p.130℃m.p.119℃m.p.128-130℃m.p.145-147℃m.p.80-81℃m.p.88-90℃m.p.112-113℃m.p.108-109℃m.p.95-96℃m.p.105-111℃m.p.82-85℃m.p.135-136℃m.p.85-87℃m.p.59-60℃
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    209210211213216218219220221223224229230231232233     糊状NMR:1.83(s.3H),3.67(s.3H),4.30-4.50(m.2H),5.82(br.1H),7.03-7.05(m.2H),7.37(d.2H),7.61(d.2H),7.74(d.1H),7.98(d.1H).m.p.90-91℃糊状NMR:1.83(s.3H),3.68(s.2H),4.30-4.46(m.2H),5.73(br.1H),7.03-7.10(m.2H),7.38(d.2H),7.61(d.2H),7.75(d.1H),7.98(d.1H).m.p.103-105℃m.p.87-88℃m.p.159-161℃m.p.177-178℃m.p.140-143℃m.p.133-137℃m.p.88-89℃m.p.86-88℃nD1.554(26℃)m.p.131-132℃m.p.100℃nD1.543(21℃)m.p.123-124℃
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    234235236237238243244245253269270278279280281282283284285286287 m.p.141℃m.p.130-131℃m.p.154-155℃m.p.94℃m.p.85℃m.p.104-106℃m.p.136℃m.p.87℃m.p.97-99℃m.p.137-139℃m.p.138℃m.p.71-73℃m.p.103-106℃m.p.106-108℃m.p.114-117℃m.p.121-125℃m.p.105-106℃m.p.141-143℃m.p.115-120℃m.p.162-164℃m.p.140-142℃
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    288289290291292293294295296297298299 糊状NMR:1.89(s.3H),4.27(s.2H),6.52(br.1H),7.26(d.2H),7.30-7.60(m.5H).糊状NMR:1.91(s.3H),4.31(s.2H),6.28(br.1H),6.96(d.2H),7.35-7.60(m.5H).m.p.163-164℃糊状NMR:1.92(s.3H),4.37(s.2H),6.33(br.1H),7.02(d.2H),7.35(d.2H),7.47(d.2H),7.59(d.2H),m.p.135-140℃m.p.135-136℃m.p.115℃m.p.128-130℃m.p.118-119℃m.p.134-140℃m.p.125-135℃糊状NMR:1.40-2.30(m.8H),4.62/4.99(br.s.1H),6.38/6.62(br.s.1H),6.99-6.97(m.2H),7.16-7.30(m.2H),7.62-7.82(m.4H)
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    300301302303304305306307308309310311312313314315316     糊状NMR:1.50-2.35(m.8H),1.84(s.3H),4.12(q.2H),6.31(br.s.1H),6.92(d.2H),7.21(dd.1H),7.34(dd.1H),7.66(d.2H),7.85(d.2H)m.p.135-136℃m.p.217-218℃m.p.195-198℃m.p.129-130℃m.p.106-108℃m.p.132-136℃m.p.92℃m.p.72-77℃m.p.135-137℃m.p.120-122℃m.p.155-160℃m.p.96-97℃m.p.127-129℃m.p.127-128℃m.p.161-166℃糊状NMR:1.98(s.3H),4.45(q.2H),6.65(br.s.1H),7.03(d.2H),7.58(d.2H),7.76(d.2H),7.88(d.2H)
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    317318319320321322323324325326327328329330331332333334     糊状NMR:1.98(s.3H),4.47(s.2H),6.33(br.s.1H),7.01(d.1H),7.32(m.4H),7.57(d.2H)糊状NMR:1.97(s.3H),4.44(q.2H),6.56(br.s.1H),7.02(d.2H),7.53(m.1H),7.61(d.2H),7.63(s.2H)m.p.122-123℃m.p.149-154℃m.p.144-145℃m.p.205-208℃m.p.142-144℃m.p.147-148℃m.p.130-132℃m.p.98-100℃m.p.118-121℃m.p.140-141℃m.p.137-140℃m.p.166-168℃m.p.187-190℃m.p.85-88℃m.p.127-128℃m.p.171-173℃
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    335336337338339340341342343344345346347348 m.p.158-159℃m.p.150-154℃m.p.137-140℃m.p.219-222℃m.p.126-130℃m.p.133-134℃糊状NMR:1.99(s.3H),2.50(s.3H),4.41(d.1H),4.49(d.1H),7.03(d.2H),7.25(d.2H),7.30(br.s.1H),7.59(d.2H),8.18(d.1H)m.p.119-123℃m.p.249-251℃m.p.184-187℃m.p.254-257℃m.p.170-173℃m.p.111-114℃糊状NMR:1.97(s.3H),4.40(d.1H),4.47(d.1H),6.65(br.s.1H),7.03(d.2H),7.19-7.23(m.1H),7.59(d.2H),7.62(t.1H),7.80-7.91(m.1H),8.55-8.57(m.1H)
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    349350351352353354355356357358359 糊状NBR:1.94(s.3H),4.41(dd.2H),6.71(br.s.1H),6.93(d.1H),7.00(d.2H),7.45(t.2H),7.55(d.2H),8.11-8.14(m.1H),8.56(d.1H)m.p.118-119℃m.p.161-163℃m.p.132-139℃m.p.149-151℃糊状NMR:1.22-1.29(m.6H),2.76(m.1H),4.60(q.2H),6.70(br.s.1H),6.99(d.2H),7.34(m.1H),7.43(m.1H),7.48(d.2H),7.70(d.2H)糊状NMR:1.20-1.32(m.6H),2.81(m.1H),4.60(q.2H),6.43(br.s.1H),6.98(d.2H),7.55(d.2H),7.76-7.86(m.4H),7.70(d.2H)糊状NMR:1.52-1.57(m.3H),1.91/1.93(s.3H),5.03/5.26(q.2H),6.76/6.96(br.s.1H),6.98-7.10(m.2H),7.26-7.79(m.5H)m.p.210-213℃(Rf=H)m.p.206-208℃(Rf=L)m.p.90-91℃
表4(续)
    No.     物理性质(熔点，折射率，NMR(CDCl3/TMS),δ值(ppm))
    360361362363364365366367368369 m.p.137-140℃m.p.132℃糊状NMR:1.99(s.3H),4.43(d.2H),4.49(d.1H),7.04(d.2H),7.57(d.2H),7.89(d.1H),8.25(br.s.1H),8.41(d.1H)糊状NMR:1.99(s.3H),2.61(s.3H),4.46(s.2H),7.02-7.09(m.4H),7.58(d.2H),7.92-7.96(m.1H),8.53-8.55(m.1H)m.p.200-202℃m.p.137-142℃m.p.130-133℃m.p.138-140℃m.p.141-142℃m.p.138-139℃
在表3或4中，Rf-H或Rf-L表示立体异构体；Rf-H表示在立体异构体中具有较高Rf值的异构体，Rf-L表示具有较低Rf值的异构体。
下面是本发明的典型实施例、制剂实施例和测试实施例。实施例实施例1第63号化合物的制备
将4-氯苯酚(2.56g)、溴代乙醛二甲基乙缩醛(3.4g)、无水碳酸钠(2.76g)和催化量的碘化钠加入DMF(二甲基甲酰胺)中并加热回流3小时。向反应混合物中加水，然后用乙酸乙酯萃取，有机层用无水硫酸钠干燥并蒸去溶剂。通过硅胶柱色谱法提纯残余物(乙酸乙酯-己烷)，得到4-氯苯氧基乙醛二甲基乙缩醛(2.37g)。
将4-氯苯氧基乙醛二甲基乙缩醛(1.0g)溶解在丙酮(10ml)中，加入2N盐酸(1.0g)，把混合物加热回流8小时。在浓缩反应混合物后，加入水并用乙酸乙酯萃取。用无水硫酸钠干燥萃取液。蒸去溶剂得到4-氯苯氧基乙醛粗产品。
将4-氯苯氧基乙醛粗品(0.5g)、***(0.17g)和氯化铵(0.27g)加入28％氨水(20ml)中并搅拌2天。向反应溶液中加入乙酸乙酯，用水洗涤反应混合物，用无水硫酸钠干燥并蒸去溶剂。把所得的油状物溶于THF(四氢呋喃)(5ml)中并加入4-氯苯乙酰氯(0.38g)和三乙胺(0.22g)。所得的混合物室温搅拌6小时。向反应混合物中加入水，用乙酸乙酯萃取，用无水硫酸钠干燥萃取液并蒸去溶剂。通过硅胶柱色谱法提纯残余物(乙酸乙酯-己烷)，得到目标化合物(0.21g；产率24％；熔点122-128℃)。实施例2第64号化合物的制备
将4-氯苯酚(10g)、氯代丙酮(10.8g)、无水碳酸钾(12.9g)和碘化钾(1.3g)加入丙酮(100ml)中并加热回流6小时。过滤反应混合物，浓缩滤液得到4-氯苯氧基丙酮(14g)。
将4-氯苯氧基丙酮(6.0g)、***(1.91g)和氯化铵(2.6g)加入28％氨水(20ml)中并剧烈搅拌24小时。向反应混合物中加入乙酸乙酯，用水洗涤反应混合物，用无水硫酸钠干燥并蒸去溶剂，得到2-氨基-2-甲基-3-(4-氯代苯氧基)丙腈(6.5g)。
将4-氯苯乙酸(0.4g)加入亚硫酰氯(1ml)中并加热回流1小时，减压蒸去过量的亚硫酰氯。在冰冷却下把所得的酰氯加入到到溶有2-氨基-2-甲基-3-(4-氯苯氧基)丙腈(0.49g)和三乙胺(0.26g)的THF溶液(5ml)中，并在室温下搅拌3小时。向反应混合物中加入水并用乙酸乙酯萃取。用无水硫酸钠干燥萃取液并蒸去溶剂。用己烷-醚洗涤固体残余物，得到目标化合物(0.56g；产率66％；熔点152℃)。实施例3第81号化合物的制备
将4-氯苯氧基丙酮(1.84g)、***(0.5g)、氯化铵(0.9g)溶于甲醇(10ml)中，向其中加入过量的乙胺水溶液。室温搅拌反应混合物2天。在反应结束后，蒸去溶剂并用乙酸乙酯萃取残余物，随后通过普通方法得到2-乙氨基-2-甲基-3-(4-氯苯氧基)丙腈(2.2g)。
将2-乙氨基-2-甲基-3-(4-氯苯氧基)丙腈(0.5g)和4-氯苯乙酰氯(0.38g)溶于THF(10ml)中，向其中加入吡啶(0.16g)，把反应混合物加热回流5小时。在冷却至室温后，滤去不溶物并蒸去溶剂。通过硅胶柱色谱法提纯所得的油状物(乙酸乙酯-己烷)，得到目标化合物(0.16g；产率20％；熔点83-84℃)。实施例4第166号化合物的制备
将4-甲氧基苯乙酸(0.67g)和碘化2-氯-1-甲基吡啶(1.10g)悬浮分散在THF(10ml)中，室温下向其中再室温滴加三乙胺(0.50g)。搅拌5分钟后，加入2-氨基-2-甲基-3-(4-氯苯氧基)丁腈(0.90g)并搅拌所得的混合物6小时。在反应结束后，滤去不溶物并蒸去溶剂。通过硅胶柱色谱法提纯残余物(乙酸乙酯-己烷)，得到目标化合物(0.78g；产率52％；熔点129-131℃)。实施例5第253号化合物的制备
将盐酸2-(5-三氟甲基-2-吡啶基)乙酸(0.74g)、2-氨基-2-甲基-3-(4-三氟甲基苯氧基)丙腈(0.65g)、碘化2-氯-1-甲基吡啶(1.17g)和三乙胺(0.93g)加入乙腈(10ml)中并加热回流6小时。向反应混合物中加入水并用乙酸乙酯萃取，用无水硫酸钠干燥。随后，蒸去溶剂。通过硅胶柱色谱法提纯残余物(乙酸乙酯-己烷)，得到目标化合物(0.34g；产率28％；熔点97-99℃)。实施例6第288号化合物的制备
将3-苯基丙炔酸(0.28g)、2-氨基-2-甲基-3-(4-氯苯氧基)丙腈(0.40g)和二环己基碳化二亚胺(0.41g)溶于二氯甲烷(5ml)中并把溶液加热回流8小时。过滤反应混合物，浓缩滤液。通过硅胶柱色谱法提纯残余物(乙酸乙酯-己烷)，得到目标化合物(0.11g；产率17％；糊状)。
包含本发明式(Ⅰ)所示的氨基乙腈衍生物作为活性成分的农业和园艺杀虫剂，适于防治农业、林业、园艺、储藏品中的各种害虫及对水稻、果树、蔬菜、其他作物和花卉有害的寄生虫或线虫。它对各种害虫具有很强的杀虫效果，例如，鳞翅目害虫如桔黄小卷叶蛾(Adoxophyes oranafasciata)、茶小卷叶蛾(Adoxophyes sp.)、苹小食心虫(Grapholita inopinata)、梨小食心虫(Grapholitamolesta)、大豆食心虫(Leguminivora glycinivorella)，桑卷叶蛾(0lethreutesmori)、茶叶细蛾(Caloptilia thevivora)、猛花细蛾Caloptilia zachrysa、窄翅潜叶蛾(Phyllonorycterringoniella)、梨潜叶细蛾(Spulerrina astaurota)、菜粉蝶(Piersrapae cruciyora)、棉铃虫(Heliothis sp.)、苹果小卷蛾(Laspeyresia pomonella)、菜蛾(Plutella xylostella)、苹果银蛾(Argyresthia conjugella)、桃小食心虫(Carposinaniponesis)、二化螟(Chilo suppressalis)、稻纵卷叶野螟(Cnaphalocrocis medinalis)、烟草粉斑螟(Ephestiaelutella)、桑螟(Glyphodes pyloalis)、三化螟(Scirpophagaincertulas)、稻苞虫(Parnara guttata)、眉纹夜蛾(Pseudaletiaseparata)、大螟(Sesamia inferens)、斜纹夜蛾(Spodopteralitura)、甜菜夜蛾(Spodoptera exigua)；半翅目害虫如紫箢叶蝉(Macrosteles fascifrons)、稻大白叶蝉(Nephotettixcincticeps)、稻褐飞虱(Nilaparvata lugens)、白背飞虱(Sogatella furcifera)、桔木虱(Diaphorina citri)、日本葡萄粉虱(Aleurolobus taonabae)、棉粉虱(Bemisia tabaci)、温室粉虱(Trialeurodes vaporariorum)、萝卜蚜(Lipaphiserysimi)、桃蚜(Myzus persicae)、角盘蚧(Ceroplastesceriferus)、桔绵蜡蚧(Pulyinaria aurantil)、樟圆蚧(Pseudaonidia duplex)、梨圆蚧(Comstockaspis perniciosa)、矢尖蚧(Unaspis yanonesis)；鞘翅目害虫如红铜丽金龟(Anomalarufocuprea)、日本丽金龟(Popillia japonica)、烟草甲(Lasioderma serricorne)、欧洲竹粉蠹(Lyctus brunneus)、马铃薯瓢虫(Epilachna vigintiotopunctata)、绿豆象(Callosobruchus chinensis)、蔬菜象甲(Listroderescostirostris)、玉米象(Sitophilus zeamais)、棉铃象(Anthonomus gradis gradis)、稻象甲(Lissorhoptrusoryzophilus)、黄守瓜(Aulacophora femoralis)、稻负泥虫(Oulema oryzae)、黄曲条跳甲(Phyllotreta striolata)、纵坑切梢小蠹(Tomicus piniperda)、马铃薯甲虫(Leptinotarsadecemlineata)、墨西哥豆瓢虫(Epilachna varivestis)、南瓜十二星叶甲(Diabrotica sp.)；双翅目害虫如瓜实蝇(Dacus(Zeugodacus)cucurbitae)、桔小实蝇(Dacus(Bactrocera)dorsalis)、日本稻潜蝇(Agromyza oryzae)、葱蝇(Deliaantiqua)、种蝇(Delia platura)、大豆荚瘿蚊(Asphondylia sp.)、家蝇(Musca domestica)、库蚊(Culex pipiens)；垫刃目害虫如根腐线虫(Pratylenchussp.)、马铃薯金线虫(Globoderarostochiensis)、根疣线虫属(Meloidogyne sp.)、半穿刺线虫(Tylenchulus semipenetrans)、Aphelenchus avenae，菊叶芽滑刃线虫(Aphelenchoides ritzemabosi)。
含有本发明式(Ⅰ)所示氨基乙腈衍生物的农业和园艺杀虫剂对上面提到的害虫具有显著的防治效果，这些害虫对稻田作物、农作物、果树、蔬菜和其他作物及花卉有害，在预计害虫会出现及害虫出现前或出现后，用本发明的农业和园艺杀虫剂适时地对诸如稻田水、茎和叶或者土壤、农场、果树、蔬菜、其他作物和花卉进行处理，会得到理想的效果。
根据农药在使用前惯用的调配方法，本发明农业和园艺杀虫剂通常被调配成适当的制剂以便于使用。
这就是，用适当量的式(Ⅰ)所示氨基乙腈衍生物与合适的惰性载体混合，若需要可加入辅助剂，进行溶解、分散、悬浮、混合、浸渍、吸收或者吸附，把混合物调配成悬浮液、乳液、液体、可湿性粉剂、颗粒剂、粉剂、片剂等。
在本发明中使用的惰性载体可以是任何固体或液体。使用的固体载体材料包括，例如，豆粉，谷物粉末，木粉，树皮粉末，锯屑，烟草梗粉末，胡桃壳粉，麦麸，纤维素纤维，植物提取残余物，合成聚合物如粉状合成树脂，粘土(例如，高岭土、膨润土、酸性粘土等)，滑石类(例如，滑石、叶蜡石等)，硅石(例如，硅藻土、石英砂、云母、白炭黑(细碎的水合二氧化硅，也称作水合硅酸，包含高分散性硅酸；一些产品是以硅酸钙为主要组分)，活性炭，硫粉，浮石，煅烧过的硅藻土，碎砖，飘尘和砂，无机矿物粉末如碳酸钙、磷酸钙，化肥或者硫酸铵、磷酸铵、硝酸铵、尿素、氯化铵的混合肥料。这些载体可以单独或以两种或多种混合物的形式使用。
液体载体包括本身具有溶解作用的物质和本身虽不具有溶解作用但借助于辅助剂能够分散活性成分的物质。典型实例包括下列载体，这些载体可以单独或以两种或多种混合物的形式使用，例如，水，醇类(例如，甲醇、乙醇、异丙醇、丁醇、1,2-亚乙基二醇等)，酮类(例如，丙酮、甲基乙基酮、甲基异丁基酮、二异丁基酮、环己酮等)，醚类(例如，***、二恶烷、乙二醇-***、二丙醚、四氢呋喃等)，脂族烃(例如，煤油、矿物油等)，芳族烃(例如，苯、甲苯、二甲苯、溶剂石脑油、烷基萘等)，卤代烃(例如，二氯乙烷、氯仿、四氯化碳、氯苯等)，酯类(例如，乙酸乙酯、邻苯二甲酸酯、邻苯二甲酸二异丙酯、邻苯二甲酸二丁酯、邻苯二甲酸二辛酯等)，酰胺类(例如，二甲基甲酰胺、二乙基甲酰胺、二甲基乙酰胺等)，腈类(例如，乙腈等)，二甲亚砜，等等。
其他辅助剂包括下面列举的这些具有代表性的辅助剂。依使用的目的而定，这些辅助剂可以单独使用，或者两种或多种结合起来使用。或者，在一些情况下也可以不用辅助剂。
使用表面活性剂的目的是为了乳化、分散、溶解和/或润湿活性成分。表面活性剂的实例包括，例如，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、聚氧乙烯脱水山梨糖醇一月桂酸酯、聚氧乙烯脱水山梨糖醇一油酸酯、烷芳基磺酸盐、萘磺酸缩合物、木素磺酸盐、高级醇硫酸盐，等等。
辅助剂也可以用于稳定活性成分化合物及粘合或束缚活性成分化合物。这样辅助剂的实例包括酪蛋白、明胶、淀粉、甲基纤维素、羧甲基纤维素、***树胶、聚乙烯醇、松节油、米糠油、膨润土、木素亚硫酸盐废液，等等。
辅助剂可以作来改善固体产物的流动性。这样辅助剂的实例是，例如，蜡、硬脂酸酯、磷酸烷基酯，等等。
辅助剂如萘磺酸缩合物、缩聚磷酸盐等可作为悬浮产物的抗絮凝剂使用。
辅助剂如硅油可作为消泡剂使用。
如果需要，可以调整活性成分化合物的量。例如，在粉剂和颗粒剂中，其合适的含量是0.01-50wt％。在乳剂和可湿性粉剂中，其合适的含量也是0.01-50wt％。
为了防治各种病害，对于预计会出现害虫的作物或不希望有害虫出现的场所，可以施用有效量的本发明农业和园艺杀虫剂(适当地用水等稀释或者悬浮在水或其类似物中)来预防虫害。
本发明农业和园艺杀虫剂施用量的变化，取决于诸如施用目的、被防治的害虫、作物生长状态、害虫出现趋势、天气、环境条件、制剂形式、施用场所、施用地点、施用时期等各种因素。然而，施用量若以活性成分化合物的量来表示，视目的而定应该适当地选择在0.1g-10kg/10acres范围内。
为了进一步扩展可防治的病害和害虫、最佳防治时间或者减少施用剂量，本发明的农业和园艺杀虫剂可以与其他农业和园艺病害虫害防治剂结合使用。
下面给出了本发明的典型实例和测试实例。然而，本发明决不受此限制。
在下面的制剂中，所有的份数是指重量份数。制剂实施例1
表1、2或3中所述化合物     50份
二甲苯                    40份
聚氧乙烯壬基苯基醚
和烷基苯磺酸钙的混合物    10份
将上面提到的各种组分均匀混合并溶解，制成乳剂。制剂实施例2
表1、2或3中所述化合物      3份
粘土粉                    82份
硅藻土粉                  15份
将上面提到的各种成分均匀混合并磨成粉状，制成粉剂。制剂实施例3
表1、2或3中所述化合物      5份
膨润土和粘土粉末          90份
木素磺酸钙                 5份
将上述各种成分均匀混合并与适量的水捏合，将所得的混合物造粒并干燥得到颗粒剂。制剂实施例4
表1、2或3中所述化合物     20份
高岭土和高分散性合成硅酸  75份
聚氧乙烯壬基苯基醚
和烷基苯磺酸钙的混合物     5份
将上面提到的各种成分均匀混合并磨成粉状，制成可湿性粉剂。测试实施例1对菜蛾(Plutella xylostella)的杀虫效果
将菜蛾(Plutella xylostella)成虫放置在白菜幼苗上喂养并使其产卵，在喂养开始2天后，把产有虫卵的白菜幼苗用化学液浸渍30秒，这种化学液是把包含有表1、表2或表3所述化合物的化学试剂稀释至500ppm制备而成的。风干后，把幼苗放置在温度25℃的温室里。在化学溶液中浸渍后再过6天，检查孵化的昆虫。通过下式计算昆虫死亡率并根据下面标准进行判定。l组，10只昆虫，3个系列体系。
Figure A9910528900651
评价标准：
A：昆虫死亡率  100％
B：昆虫死亡率99-90％
C：昆虫死亡率89-80％
D：昆虫死亡率79-50％
得到的结果如表5中所示。测试实施例2对茶小卷叶蛾(Adoxophyes sp.)的杀虫效果
将茶(品种：Yabukita)的叶子在化学液中浸渍30秒，这种化学液是把含有表1、表2或表3所述化合物的化学试剂稀释至500ppm制备而成的。风干后，将其放在直径9cm的塑料盘中，用第2龄的茶小卷叶蛾幼虫(Adoxophyes sp.)对其进行接种。此后，用盖子把塑料盘盖上并放置在温度25℃和湿度70％的温室里。接种8天后，检查昆虫的死亡数并根据测试实施例1进行评价。1组，10只昆虫，3个系列体系。
得到的结果如表5中所示。表5
  化合物序号   测试实施例1   测试实施例2  化合物序号   测试实施例1   测试实施例2
    231213142122232425262728293041424648     AAAAAAAAAAAAAA     AAAAAAAAAAAAAAAA     49525354555760626466676869737475767779     BAAAAAAAAAAAAA AAAAAAAAADAAAAAAAA
表5(续)
   化合物序号   测试实施例1   测试实施例2    化合物序号  测试实施例1  测试实施例2
    80818384919294959697100105108114116118121122123124126128     AAABAAAAAAAAAAAAAA     AAAAAAAAAAAAAACAAAAAA     141143146147148149150151153156157163165173174176184186188187189190     AAAAAAAAAAAAAAAAAA     AAAAAAAAAAAAAAAAAAAAAA
表5(续)
   化合物序号  测试实施例1  测试实施例2    化合物序号 测试实施例1  测试实施例2
    191195196197200207209220221223224229231232233234235236237238243244     AAAAAAAAAAAAAAAA     AAAAAAAAAAAAAAACAAAAAA     245253269270271278279280282283284285286293294296299306307309310311 AAAAAAAAAAAAAAA     AAAAAAAAACAAAAAAAAAAA
表5(续)
  化合物序号   测试实施例1   测试实施例2   化合物序号  测试实施例1   测试实施例2
    312313314316317318319320321322324325326327328333336337339342348349     AAAAAAAAA     AAAAAAAAAAAAAAAAAAAAAA     350351353354355356359362363366369 AA     AAAAAAAAAAA

Claims (5)

1．式(Ⅰ)所示的氨基乙腈衍生物：
Figure A9910528900021
(其中Ar1和Ar2可以相同或者不同，各表示苯基；
具有至少一个取代基的取代苯基，其取代基可以相同或者不同并选自
卤原子，硝基，氰基，
C1-C6烷基，卤代C1-C6烷基，
C1-C6烷氧基，卤代C1-C6烷氧基，
C2-C6链烯基，卤代C2-C6链烯基，
C2-C6链炔基，C3-C6环烷基，
C2-C6链烯氧基，卤代C2-C6链烯氧基，
C1-C6烷硫基，卤代C1-C6烷硫基，
C1-C6烷基磺酰氧基，
卤代C1-C6烷基磺酰氧基，
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，
C2-C6链烯硫基，
卤代C2-C6链烯硫基，
C2-C6链烯基亚磺酰基，
卤代C2-C6链烯基亚磺酰基，
C2-C6链烯基磺酰基，
卤代C2-C6链烯基磺酰基，
C1-C6烷基氨基、二-C1-C6烷基氨基，
C1-C6烷基磺酰氨基，卤代C1-C6烷基磺酰氨基，
C1-C6烷基羰基，
卤代C1-C6烷基羰基，
C1-C6烷氧羰基，
苯基，
具有至少一个取代基的取代苯基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、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，
苯氧基，
在其环上具有至少一个取代基的取代苯氧基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、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，
苯乙炔基，
在其环上具有至少一个取代基的取代苯乙炔基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、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，
吡啶氧基和
在其环上具有至少一个取代基的取代吡啶氧基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、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；
吡啶基；
在其环上具有至少一个取代基的取代吡啶基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C2-C6链烯氧基、卤代C2-C6链烯氧基、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、C2-C6链烯硫基、卤代C2-C6链烯硫基、C2-C6链烯基亚磺酰基、卤代C2-C6链烯基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C2-C6链烯基磺酰基、卤代C2-C6链烯基磺酰基、C1-C6烷基氨基和二-C1-C6烷基氨基；
萘基；或
在其环上具有至少一个取代基的萘基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C2-C6链烯氧基、卤代C2-C6链烯氧基、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、C2-C6链烯硫基、卤代C2-C6链烯硫基、C2-C6链烯基亚磺酰基、卤代C2-C6链烯基亚磺酰基、C2-C6链烯基磺酰基、卤代C2-C6链烯基磺酰基、C1-C6烷基氨基和二-C1-C6烷基氨基；
Q表示基团
Figure A9910528900041
(其中R1和R2可以相同或者不同，各表示氢原子，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，C3-C6环烷基，或具有至少一个取代基的取代C3-C6环烷基，所述取代基可以相同或者不同并选自卤原子和C1-C6烷基，并且R1和R2可以连在一起表示在其链上可具有至少一个取代基的C2-C6亚烷基，所述取代基选自卤原子、C1-C6烷基和C1-C6烷氧基)，-CH=CH-或-C=C-；d是0或者整数1；
R3表示氢原子、C1-C6烷基、卤代C1-C6烷基、氰基C1-C6烷基、C1-C6烷硫基、卤代C1-C6烷硫基、C2-C6链烯基或C2-C6链炔基；
R4、R5、R6、R7和R8可以相同或者不同并且各表示氢原子，卤原子，C1-C6烷基，卤代C1-C6烷基，C3-C6环烷基，具有至少一个取代基的取代C3-C6环烷基，其取代基可以相同或者不同并选自卤原子和C1-C6烷基，苯基或具有至少一个取代基的取代苯基，所述取代基可以相同或者不同并选自卤原子、硝基、氰基、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、C1-C6烷基氨基和二-C1-C6烷基氨基，并且R4和R5一起可以形成C1-C6亚烷基；
W是-O-、-S-、-SO2-或-N(R9)-(其中R9表示氢原子或C1-C6烷基)，及
a和b可以相同或者不同并表示0或1-4的整数))。
2． 根据权利要求1的氨基乙腈衍生物，其中Ar1和Ar2表示苯基；
具有至少一个取代基的取代苯基，其取代基可以相同或者不同并选自下列基团
卤原子，氰基，硝基，
C1-C6烷基，卤代C1-C6烷基，
C2-C6链烯基，卤代C2-C6链烯基，
C2-C6链炔基，C3-C6环烷基，
C1-C6烷氧基，卤代C1-C6烷氧基，
C2-C6链烯氧基，卤代C2-C6链烯氧基，
C1-C6烷基磺酰氧基，
卤代C1-C6烷基磺酰氧基，
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，
C2-C6链烯硫基，
卤代C2-C6链烯硫基，
C2-C6链烯基亚磺酰基，
卤代C2-C6链烯基亚磺酰基，
C2-C6链烯基磺酰基，
卤代C2-C6链烯基磺酰基，
C1-C6烷基氨基、二-C1-C6烷基氨基，
C1-C6烷基磺酰氨基，卤代C1-C6烷基磺酰氨基，
C1-C6烷基羰基，
卤代C1-C6烷基羰基，
C1-C6烷氧羰基，
苯基，
具有至少一个取代基的取代苯基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷基磺酰氧基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基，
苯氧基，
在其环上具有至少一个取代基的取代苯氧基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基，
苯乙炔基，
在其环上具有至少一个取代基的取代苯乙炔基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、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，
吡啶氧基和
在其环上具有至少一个取代基的取代吡啶氧基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基；
吡啶基；
在其环上具有至少一个取代基的取代吡啶基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基和卤代C1-C6烷基亚磺酰基、卤代C1-C6烷基磺酰基，
萘基；和
在其环上具有至少一个取代基的萘基，其取代基可以相同或者不同，选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基，
Q表示基团(其中R1和R2可以相同或者不同并且各表示氢原子，卤原子，C1-C6烷基，卤代C1-C6烷基和C1-C6烷氧基，以及R1和R2可以连在一起表示在其链上可具有至少一个取代基的C2-C6亚烷基，所述取代基选自卤原子、C1-C6烷基或C1-C6烷氧基)，-CH=CH-或-C≡C-；d是0或者整数1；
R3表示氢原子、C1-C6烷基、卤代C1-C6烷基、C2-C6链烯基或C2-C6链炔基；
R4、R5、R6、R7和R8可以相同或者不同并且各表示氢原子，C1-C6烷基，卤代C1-C6烷基，C3-C6环烷基或具有至少一个取代基的取代C3-C6环烷基，所述取代基可以相同或者不同并选自卤原子和C1-C6烷基，以及R4和R5一起可以形成C1-C6亚烷基；
W是-O-、-S-、-SO2-或-N(R9)-(其中R9表示氢原子或C1-C6烷基)，及
a和b可以相同或者不同并表示0或1-4的整数))。
3． 根据权利要求2的氨基乙腈衍生物，其中Ar1和Ar2表示苯基；
具有至少一个取代基的取代苯基，其取代基可以相同或者不同并选自下列基团
卤原子，氰基，硝基，
C1-C6烷基，卤代C1-C6烷基，
C1-C6烷氧基，卤代C1-C6烷氧基，
C2-C6链烯氧基，卤代C2-C6链烯氧基，
C1-C6烷硫基，卤代C1-C6烷硫基，
C1-C6烷基磺酰基，
卤代C1-C6烷基磺酰基，
C2-C6链烯硫基，
卤代C2-C6链烯硫基，
C2-C6链烯基磺酰基，
卤代C2-C6链烯基磺酰基，
C1-C6烷氧羰基，
苯基，
具有至少一个取代基的取代苯基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基和卤代C1-C6烷基磺酰基，
苯氧基，
在其环上具有至少一个取代基的取代苯氧基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基和卤代C1-C6烷基磺酰基，
苯乙炔基，
在其环上具有至少一个取代基的取代苯乙炔基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基和卤代C1-C6烷基磺酰基，
吡啶氧基和
在其环上具有至少一个取代基的取代吡啶氧基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基和卤代C1-C6烷基磺酰基；
吡啶基；
在其环上具有至少一个取代基的取代吡啶基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基和卤代C1-C6烷基亚磺酰基；
萘基；或
在其环上具有至少一个取代基的萘基，其取代基可以相同或者不同并选自卤原子、氰基、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基和卤代C1-C6烷基磺酰基；
Q表示基团
Figure A9910528900091
(其中R1和R2可以相同或者不同并且各表示氢原子，卤原子，C1-C6烷基，卤代C1-C6烷基或C1-C6烷氧基，并且R1和R2可以连在一起表示在其链上可具有至少一个取代基的C2-C6亚烷基，所述取代基选自卤原子、C1-C6烷基和C1-C6烷氧基)，-CH=CH-或-C≡C-；d是0或者整数1；
R3表示氢原子、C1-C6烷基、卤代C1-C6烷基、C2-C6链烯基或C2-C6链炔基；
R4、R5、R6、R7和R8可以相同或者不同并且各表示氢原子，C1-C6烷基，卤代C1-C6烷基，C3-C6环烷基或具有至少一个取代基的取代C3-C6环烷基，其取代基可以相同或者不同并选自卤原子和C1-C6烷基，并且R4和R5一起可以形成C1-C6亚烷基；
W是-O-、-S-、-SO2-或-N(R9)-(其中R9表示氢原子或C1-C6烷基)，及
a和b可以相同或者不同并表示0或卜4的整数))。
4．包含根据权利要求1-3任一项的氨基乙腈衍生物作为活性成份的农业和园艺农药。
5．所述农业和园艺农药的使用方法，该方法包括将有效量的如权利要求4所述的农业和园艺杀虫剂施用于有用植物以保护有用的植物。
CN99105289A 1998-05-01 1999-04-30 氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途 Expired - Lifetime CN1132516C (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP137806/98 1998-05-01
JP13780698 1998-05-01
JP137806/1998 1998-05-01

Publications (2)

Publication Number Publication Date
CN1234177A true CN1234177A (zh) 1999-11-10
CN1132516C CN1132516C (zh) 2003-12-31

Family

ID=15207294

Family Applications (1)

Application Number Title Priority Date Filing Date
CN99105289A Expired - Lifetime CN1132516C (zh) 1998-05-01 1999-04-30 氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途

Country Status (9)

Country Link
US (1) US6239077B1 (zh)
EP (2) EP1445251B1 (zh)
JP (1) JP4310717B2 (zh)
KR (1) KR100676111B1 (zh)
CN (1) CN1132516C (zh)
AU (1) AU752112B2 (zh)
DE (3) DE122010000014I1 (zh)
FR (1) FR10C0009I2 (zh)
TW (1) TW585849B (zh)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1293047C (zh) * 2001-12-06 2007-01-03 诺瓦提斯公司 适用于控制寄生虫的氨基乙腈衍生物
CN1304378C (zh) * 2001-11-14 2007-03-14 诺瓦提斯公司 用于控制寄生虫的苯并咪唑－或吲哚－氨基乙腈衍生物
CN1309715C (zh) * 2002-05-22 2007-04-11 诺瓦提斯公司 N－酰氨基乙腈衍生物及其用于制备控制寄生虫的药物中的用途
CN100347153C (zh) * 2002-06-06 2007-11-07 诺瓦提斯公司 酰氨基乙腈化合物及其作为杀虫剂的用途
CN100447130C (zh) * 2003-11-06 2008-12-31 诺瓦提斯公司 酰氨基乙腈衍生物
CN101857544A (zh) * 2010-06-03 2010-10-13 上海力智生化科技有限公司 一种除草剂2,4-二氯苯氧乙酸的合成方法
CN104837812A (zh) * 2012-08-06 2015-08-12 皮特尼制药股份有限公司 治疗mTOR通路相关的疾病的化合物
CN105492452A (zh) * 2013-07-01 2016-04-13 苏黎世大学 有机金属2-氰基-2-氨基苯甲酸基丙基衍生物及其作为抗蠕虫药的用途
CN105658056A (zh) * 2013-07-01 2016-06-08 苏黎世大学 用作杀线虫药物的n-(1-氰基-2-羟基-1-甲基-乙基)-4-(三氟甲基巯基)苯甲酰胺衍生物
CN105682464A (zh) * 2013-09-26 2016-06-15 苏黎世大学 用作抗蠕虫药的有机金属n-2-氰基-1-羟丙-2基
CN105683206A (zh) * 2013-09-26 2016-06-15 苏黎世大学 二有机金属2-氨基-3-羟基-2-甲基丙腈衍生物作为抗蠕虫药的用途

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2259804T3 (es) * 1996-04-02 2006-10-16 Bayer Cropscience Ag Fenilcetoenoles sustituidos como pesticidas y herbicidas.
KR100850252B1 (ko) * 2000-12-20 2008-08-04 노파르티스 아게 유기 화합물
AU2002224942A1 (en) * 2000-12-20 2002-07-01 Syngenta Participations Ag N-acyl aminoacetonitriles having pesticidal properties
AR035531A1 (es) * 2001-01-22 2004-06-02 Novartis Ag Composicion para el control de plagas endoparasiticas en ganados y animales domesticos, un metodo para su control y el uso de dicha composicion para la preparacion de medicamentos
EP1390344B1 (en) 2001-05-15 2006-12-27 Novartis AG Benzamidoacetonitrile derivatives and their use as antiparasitics
AR036054A1 (es) * 2001-06-15 2004-08-04 Novartis Ag Uso de compuestos de aminoacetonitrilo para el control de plagas, una composicion y un proceso para dicho control y una composicion farmaceutica contra parasitos
WO2003004474A1 (en) * 2001-07-06 2003-01-16 Syngenta Participations Ag Pesticidally active aminoacetonitriles
BR0213066A (pt) * 2001-10-04 2004-09-28 Novartis Ag Compostos de cianoacetila
CN1545500A (zh) 2001-10-04 2004-11-10 诺瓦提斯公司 作为抗寄生虫剂的羰氧基-氰基甲基化合物
AR038156A1 (es) * 2002-01-21 2004-12-29 Novartis Ag Compuestos de amidoacetonitrilo, proceso para su preparacion, composicion para controlar los parasitos, y uso de estos compuestos para preparar una composicion farmaceutica
AR039020A1 (es) * 2002-03-21 2005-02-02 Novartis Ag Compuestos de aminoacetonitrilo
TW200400931A (en) 2002-05-22 2004-01-16 Novartis Ag Organic compounds
AR040149A1 (es) * 2002-06-07 2005-03-16 Novartis Ag Compuestos de aminoacetonitrilo, un proceso para su preparacion, composicion, y uso del compuesto
TW200400932A (en) 2002-06-19 2004-01-16 Novartis Ag Organic compounds
US7022703B2 (en) * 2003-07-24 2006-04-04 Janssen Pharmaceutica, N.V. Acetylenic compound useful in treating inflammatory disorders
AR046757A1 (es) * 2003-12-10 2005-12-21 Novartis Ag Amidoacetonitrilos utiles como pesticidas
TW200613251A (en) 2004-06-10 2006-05-01 Novartis Ag Organic compounds
WO2006043654A1 (ja) * 2004-10-22 2006-04-27 Nihon Nohyaku Co., Ltd. アセトニトリル誘導体及び有害生物防除剤並びにその使用方法
AR051761A1 (es) * 2004-11-09 2007-02-07 Novartis Ag Compuestos organicos
JP2009502834A (ja) * 2005-07-25 2009-01-29 ノバルティス アクチエンゲゼルシャフト アミドニトリル化合物
EP1975148B1 (en) * 2006-01-20 2013-11-20 National University Corporation Yamaguchi University Aromatic compound gelatinizing agent having perfluoroalkyl group
DE102006018828A1 (de) * 2006-04-22 2007-10-25 Bayer Cropscience Ag Alkoxyalkyl-substituierte cyclische Ketoenole
WO2008062005A1 (en) * 2006-11-24 2008-05-29 Novartis Ag The use of aminoacetonitril compounds in the control of endoparasites in warm- blood animals.
RU2425825C2 (ru) 2007-02-09 2011-08-10 Пфайзер Лимитед Амидоацетонитрильные производные, содержащие их фармацевтические композиции и их применение в изготовлении лекарственного средства
CA2678149C (en) * 2007-02-21 2013-04-16 Pfizer Limited Benzofuran antiparasitic agents
PT3428148T (pt) 2007-05-15 2020-10-13 Aventis Agriculture Compostos de ariloazol-2-il-cianoetilamino, método de fabrico e seu método de utilização
DE102007028925A1 (de) * 2007-06-22 2008-12-24 Saltigo Gmbh Verfahren zur Herstellung von 2-Phenoxyacetalen und den daraus korrespondierenden 2-Phenoxycarbaldehyden
AU2009307736B2 (en) 2008-10-21 2015-02-05 Boehringer Ingelheim Animal Health USA Inc. Thioamide compounds, method of making and method of using thereof
LT3050874T (lt) 2008-11-14 2019-04-10 Merial Inc. Enantiomeriškai praturtinti arilazol-2-ilo cianetilamino paraziticidiniai junginiai
UY32992A (es) * 2009-11-23 2011-04-29 Novartis Ag Compuestos orgánicos
AR085073A1 (es) * 2012-01-11 2013-09-11 Richmond Sa Com Ind Y Financiera Lab Compuestos con actividad antibacteriana, un procedimiento para su obtencion y composiciones farmaceuticas que los comprenden
US8822689B2 (en) 2012-09-19 2014-09-02 Merial Limited Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof
AR094961A1 (es) 2013-03-15 2015-09-09 Lilly Co Eli 1-hidroxi-benzooxaboroles como agentes antiparasitarios
US9907778B2 (en) 2013-09-13 2018-03-06 Pitney Pharmaceuticals Pty Limited Anticancer agent comprising aminoacetonitrile compound as active ingredient
CN104651507B (zh) * 2015-02-10 2016-08-24 中国农业科学院棉花研究所 用于区分棉铃虫和烟青虫的特异性引物与方法
US10391076B2 (en) 2015-02-24 2019-08-27 Pitney Pharmaceuticals Pty Ltd. Anti-cancer agent comprising aminoacetonitrile compound as active ingredient
WO2020112374A1 (en) 2018-11-20 2020-06-04 Boehringer Ingelheim Animal Health USA Inc. Indazolylcyanoethylamino compound, compositions of same, method of making, and methods of using thereof
JPWO2021177334A1 (zh) * 2020-03-04 2021-09-10

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5589254A (en) * 1978-12-28 1980-07-05 Kuraray Co Ltd Substituted isovaleric acid derivative
US4804762A (en) * 1986-05-13 1989-02-14 Nippon Kayaku Kabushiki Kaisha N-cyanoalkylisonicotinamide derivatives
JPH04112872A (ja) * 1990-09-03 1992-04-14 Nippon Kayaku Co Ltd イソニコチン酸アミド誘導体を有効成分とする藻菌類による植物病害防除剤
JPH04198158A (ja) * 1990-11-29 1992-07-17 Hokko Chem Ind Co Ltd ベンズアミド誘導体および除草剤
AU666040B2 (en) 1992-10-28 1996-01-25 Bayer Aktiengesellschaft Substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives
DE4236400A1 (de) 1992-10-28 1994-05-05 Bayer Ag N-Phenylacetaminonitrile
DE4306259A1 (de) 1993-03-01 1994-09-08 Bayer Ag Dialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidin-2,4-dione, ihre Herstellung und ihre Verwendung
DE4431730A1 (de) 1994-02-09 1995-08-10 Bayer Ag Substituierte 1H-3-Aryl-pyrrolidin-2,4-dion-Derivate
RU2156235C2 (ru) 1995-05-31 2000-09-20 Кумиай Кемикал Индастри Ко., Лтд. Производные фенилалканамида, способы их получения и сельскохозяйственный или садовый фунгицид

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1304378C (zh) * 2001-11-14 2007-03-14 诺瓦提斯公司 用于控制寄生虫的苯并咪唑－或吲哚－氨基乙腈衍生物
CN1293047C (zh) * 2001-12-06 2007-01-03 诺瓦提斯公司 适用于控制寄生虫的氨基乙腈衍生物
CN1309715C (zh) * 2002-05-22 2007-04-11 诺瓦提斯公司 N－酰氨基乙腈衍生物及其用于制备控制寄生虫的药物中的用途
CN100347153C (zh) * 2002-06-06 2007-11-07 诺瓦提斯公司 酰氨基乙腈化合物及其作为杀虫剂的用途
CN100447130C (zh) * 2003-11-06 2008-12-31 诺瓦提斯公司 酰氨基乙腈衍生物
CN101857544B (zh) * 2010-06-03 2013-01-30 上海力智生化科技有限公司 一种除草剂2,4-二氯苯氧乙酸的合成方法
CN101857544A (zh) * 2010-06-03 2010-10-13 上海力智生化科技有限公司 一种除草剂2,4-二氯苯氧乙酸的合成方法
CN104837812A (zh) * 2012-08-06 2015-08-12 皮特尼制药股份有限公司 治疗mTOR通路相关的疾病的化合物
CN105496999A (zh) * 2012-08-06 2016-04-20 皮特尼制药股份有限公司 治疗mTOR通路相关的疾病的化合物
CN104837812B (zh) * 2012-08-06 2017-09-26 皮特尼制药股份有限公司 治疗mTOR通路相关的疾病的化合物
CN105492452A (zh) * 2013-07-01 2016-04-13 苏黎世大学 有机金属2-氰基-2-氨基苯甲酸基丙基衍生物及其作为抗蠕虫药的用途
CN105658056A (zh) * 2013-07-01 2016-06-08 苏黎世大学 用作杀线虫药物的n-(1-氰基-2-羟基-1-甲基-乙基)-4-(三氟甲基巯基)苯甲酰胺衍生物
CN105658056B (zh) * 2013-07-01 2018-03-06 苏黎世大学 用作杀线虫药物的n‑(1‑氰基‑2‑羟基‑1‑甲基‑乙基)‑4‑(三氟甲基巯基)苯甲酰胺衍生物
CN105682464A (zh) * 2013-09-26 2016-06-15 苏黎世大学 用作抗蠕虫药的有机金属n-2-氰基-1-羟丙-2基
CN105683206A (zh) * 2013-09-26 2016-06-15 苏黎世大学 二有机金属2-氨基-3-羟基-2-甲基丙腈衍生物作为抗蠕虫药的用途

Also Published As

Publication number Publication date
JP4310717B2 (ja) 2009-08-12
CN1132516C (zh) 2003-12-31
EP1445251A9 (en) 2004-11-03
US6239077B1 (en) 2001-05-29
FR10C0009I2 (fr) 2012-06-22
EP0953565A2 (en) 1999-11-03
DE122010000014I1 (de) 2010-07-01
EP0953565B1 (en) 2004-09-08
DE69919930D1 (de) 2004-10-14
EP1445251A1 (en) 2004-08-11
AU752112B2 (en) 2002-09-05
DE69919930T2 (de) 2005-09-08
EP0953565A3 (en) 2002-12-04
TW585849B (en) 2004-05-01
DE69934617D1 (de) 2007-02-08
EP1445251B1 (en) 2006-12-27
KR100676111B1 (ko) 2007-02-01
JP2000026392A (ja) 2000-01-25
AU2602799A (en) 1999-11-11
KR19990087988A (ko) 1999-12-27
FR10C0009I1 (zh) 2010-03-26
DE69934617T2 (de) 2007-11-15

Similar Documents

Publication Publication Date Title
CN1132516C (zh) 氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途
RU2751642C1 (ru) Соединение на основе м-диамида и способ его получения и его применение
CN102976984B (zh) 农园艺用杀虫剂的制备中间体
KR100904360B1 (ko) 아미드 유도체 및 그 제조 방법 및 그의 살충제로서의 사용방법
KR100582492B1 (ko) 프탈산디아미드유도체,농원예용살충제및살충제의사용방법
JP5149003B2 (ja) アミド誘導体ならびに該化合物を含有する殺虫剤
JP2006290883A (ja) 置換ヘテロ環カルボン酸アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
PL196644B1 (pl) Pochodne ftalamidu lub ich sól oraz rolniczo-ogrodniczy insektycyd
JP2004189738A (ja) 置換アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
KR20080017477A (ko) 아미드 유도체, 해당 화합물을 함유하는 살충제 및 그 사용 방법
WO2008075454A1 (ja) 有害生物防除組成物
JP4884072B2 (ja) 複素環誘導体ならびにその殺虫剤としての使用方法
KR20020016839A (ko) 복소환 디카르복실산 디아미드 유도체, 농원예용 살충제및 그것의 사용 방법
CN104703966B (zh) 酰亚胺化合物及其制备方法以及作为杀虫剂的应用
JP4853759B2 (ja) 置換ピラジンカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法
JPH054958A (ja) ヒドラジンカルボキサミド誘導体及びその製造方法、その用途並びにその使用方法
JP2007308470A (ja) 置換ピラゾールカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法
JP2004269515A (ja) 置換複素環アミド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
JP2879174B2 (ja) ヒドラゾン誘導体及びその製造方法、その用途並びにその使用方法
JP2003034672A (ja) フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CX01 Expiry of patent term
CX01 Expiry of patent term

Granted publication date: 20031231