CN1259118A - Organic compound - Google Patents

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CN1259118A
CN1259118A CN98805795A CN98805795A CN1259118A CN 1259118 A CN1259118 A CN 1259118A CN 98805795 A CN98805795 A CN 98805795A CN 98805795 A CN98805795 A CN 98805795A CN 1259118 A CN1259118 A CN 1259118A
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formula
alkyl
compound
hydrogen
alkoxy
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P·梅恩费什
T·高格
M·博格
T·皮特纳
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Novartis AG
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Novartis AG
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    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen 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
    • A01N37/16—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; 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
    • A01N37/18—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
    • A01N37/28—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
    • A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
    • C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
    • C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Abstract

The invention relates to fluoroalkene carboxylic acid derivatives of general formula (I), in which R1 and R2 are hydrogen (independently of each other), or alkyl, a group of formula (II), cycloalkyl, alkenyl or alkynyl, which are optionally substituted; R3 is hydrogen, fluorine, or methyl; m is 0, 1, 2, 3, 4 or 5; n is 0 or 1; X is oxygen or NR4 and R4 is hydrogen or C1-C6-alkyl or benzyl, which are optionally substituted. The invention also relates to a method for their production, to insecticides containing the new fluoroalkene carboxylic derivatives as active agent, and their use against harmful insects and acarians.

Description

Organic compound
Make the Pesticidal combination of reactive compound the present invention relates to new fluoro alkenyl carboxylic acid derivative, its preparation method and containing the new fluoro alkenyl carboxylic acid derivative, and be related to the new fluoro alkenyl carboxylic acid derivative in the harmful insect of preventing and treating and the purposes of acarid.
The present invention provides the compound of logical formula (I)Wherein：R1And R2It is hydrogen independently of one another；Or substituted or unsubstituted alkyl,
Figure A9880579500082
Aryl, cycloalkyl, alkenyl or alkynyl；R3It is hydrogen, fluorine or methyl；M is 0,1,2,3,4 or 5；N is 0 or 1；X is oxygen or NR4, and R4It is hydrogen or substituted or unsubstituted C1-C6Alkyl or benzyl, are such as suitably talked about, including its E/Z isomers, E/Z isomers mixture and/or dynamic isomer；And their free form and salt form.Condition is：If a) X is oxygen and R1And R2When being hydrogen or substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heteroaryl independently of one another, R3It is not hydrogen or fluorine and m and n can not be while be zero；If b) R4It is hydrogen and R1And R2When being hydrogen or substituted or unsubstituted alkyl, aryl or heteroaryl independently of one another, R3It is not hydrogen or fluorine and m and n can not be while be zero；If c) R1And R2One of be that when can be substituted or unsubstituted phenyl with or without the 4- alkylsulfonyloxyphenyls of other substituents, 4- haloalkylsulfonyloxys phenyl or 4- halogenated alkoxies oxyphenyl and another substituent, m be 0,1 or 2 and R4It is hydrogen, alkyl or haloalkyl；If d) R1And R2One of be that when can be substituted or unsubstituted phenyl with or without the 4- perhaloalkoxy groups phenyl and another substituent of other substituents, m be 0,1 or 2 and R4It is hydrogen, alkyl or haloalkyl and n is not zero.
The Preparation method and use of these compounds, its E/Z isomers and dynamic isomer；Contain these compounds, E/Z isomers and dynamic isomer as the agricultural chemicals of reactive compound；The preparation method and purposes of these compositions；Prepare the intermediate of the free or salt form of these compounds, and if appropriate, for, their possible E/Z isomers, E/Z isomers mixture and/or dynamic isomers；The preparation method and purposes of these intermediates and its dynamic isomer.
The preferred group of logical formula (I) compound is some groups for meeting conditions above,
Wherein R1And R2It is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, alkenyl or alkynyl, R independently of one another3It is hydrogen, fluorine or methyl, m is 0,1,2,3,4 or 5；N is 0 or 1, X are oxygen or NR4, and R4It is hydrogen, substituted or unsubstituted C1-C6Alkyl or benzyl；Wherein R1It is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl or cycloalkyl, R2It is hydrogen, substituted or unsubstituted aryl or heteroaryl, R3It is hydrogen, fluorine or methyl, m is 0,1,2,3,4 or 5；N is 0 or 1, X are oxygen or NR4, and R4It is hydrogen, substituted or unsubstituted C1-C6Alkyl or benzyl；And wherein R1And R2It is hydrogen, substituted or unsubstituted aryl, R independently of one another3It is hydrogen, fluorine or methyl, m is 0,1,2,3,4 or 5；N is 0 or 1, X are oxygen or NR4, and R4It is hydrogen or substituted or unsubstituted C1-C6Alkyl or benzyl.
Above R1, R2, R3And R4Generic term used in the definition of substituent is as defined below：
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, particularly fluorine or chlorine, especially chlorine.
Alkyl is the straight or branched alkyl with 1-20 carbon atom, and these alkyl can unsubstituted or single or multiple substitution.It is used as the R of alkyl1And R2Preferably there is 1-8 carbon atom, particularly preferably there is the straight or branched alkyl of 1-4 carbon atom.Alkyl R1And R2Suitable substituent be hydroxyl, halogen, alkoxy, halogenated alkoxy, alkyloxy-alkoxy; alkylthio group, halogenated alkylthio, alkyl sulphinyl, alkyl sulphonyl; alkylsulfonyloxy, alkyl-carbonyl, dialkylamino, pyrrolidin-1-yl; piperidino, morpholino, alkoxy carbonyl group, alkyl carbonyl oxy; cycloalkyl, aryl, aryloxy group, arylthio; aryl sulfonyl, aryl-sulfonyl oxygen, aryl carbonyl or heteroaryl, wherein aryl or heteroaryl can be by the single or multiple substitutions of following group：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, nitro, cyano group, phenoxy group, halogenated phenoxy, thiophenyl or halosphenylsulfanyl.In R1And R2Substituent in alkyl preferably there is 1-4 carbon atom.The particularly preferred methyl of these alkyl or ethyl.Alkyl R1And R2Example is methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, the tert-butyl group, n-pentyl, 1- methyl butyls, 2,2- dimethyl propyls, isopentyl, n-hexyl, 2- methyl amyls, 3- methyl amyls, 1,3- dimethylbutyl, 2- ethyl-butyls, n-heptyl, n-octyl, iso-octyl, nonyl, decyl, undecyl, lauryl, cetyl and octadecyl.It is used as the R of alkyl1And R2Preferred substituents be hydroxyl, halogen, alkoxy, halogenated alkoxy; alkyloxy-alkoxy, alkylthio group, halogenated alkylthio; alkyl sulphinyl, alkyl sulphonyl, alkylsulfonyloxy; alkyl-carbonyl, dialkylamino, pyrrolidin-1-yl; piperidino, morpholino, alkoxy carbonyl group; alkyl carbonyl oxy, cycloalkyl, wherein phenyl, phenoxy group, thiophenyl, benzenesulfonyl, phenylsulfonyloxy, benzoyl and pyridine radicals can be by following substituent groups：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, nitro or cyano group.
Group R1Or R2Single or multiple substitution refer in particular to 1-4 substitution, preferably 1-2 substitution, particularly preferably monosubstituted, wherein R1And R2, can be with perhalogeno, especially perfluoro in the case where being optionally substituted by halogen particularly such as methyl or the low alkyl group of ethyl.Each substituent can be with identical or different in the case of polysubstituted.
Aryl is phenyl or naphthyl, preferably phenyl.
Heteroaryl refers to 5 or 6 annular atoms and 1 or 2 heteroatomic aryl for being selected from nitrogen, oxygen and sulphur.The example of heteroaryl is pyrrole radicals, furyl, thienyl, imidazole radicals, pyrazolyl , oxazolyls, thiazolyl, pyridine radicals, pyridazinyl, pyrimidine radicals and pyrazinyl, in all cases, is used as the R of heteroaryl1And R2Group is connected by carbon atom, and if appropriate, phenyl ring can be fused on the group.It is preferred that heteroaryl be pyridine radicals, pyrimidine radicals, quinolyl, furyl and thienyl.
Aryl and heteroaryl can be unsubstituted or by the single or multiple substitution of following group：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, halogenated alkylthio, alkylsulfonyloxy, haloalkylsulfonyloxy, halogenated alkoxy sulfonyloxy, nitro, cyano group, benzoyl, phenyl, phenoxy group, thiophenyl, trialkylsilkl, benzyloxy, alkylamino, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino, phenylamino, cycloalkyl alkoxy or halocycloalkylalkoxy, heteroaryl or heteroaryloxy, here benzoyl, phenyl, phenoxy group, thiophenyl, benzyloxy, phenylamino, their part can be by the single or multiple substitution of following group as substituent for heteroaryl and heteroaryloxy：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, nitro, cyano group, phenoxy group, halogenated phenoxy, thiophenyl, halosphenylsulfanyl, cycloalkyl alkoxy or halocycloalkylalkoxy.It is used as aryl or heteroaryl, R1And R2Substituent or these substituents in alkyl preferably there is 1-4 carbon atom.These alkyl are particularly preferably methyl or ethyl.
Alkenyl refers to the straight or branched alkenyl with 3-20, preferably 3-8, particularly preferred 3-5 carbon atom, and the alkenyl can be unsubstituted or be replaced by one or more halogens.It is preferred that alkenyl refer to what is connected via saturated carbon atom, that is, have the alkenyl of a centre or terminal double bond.The example of alkenyl is pi-allyl, methylallyl, but-2-ene-1- bases, butyl- 3- alkene-1- bases, amyl- 2- alkene-1- bases, amyl- 3- alkene-1- bases, amyl- 4- alkene-1- bases, 2- methyl but-2-ene-1- bases, hex- 2- alkene-1- bases, hex- 3- alkene-1- bases, hex- 4- alkene-1- bases, hex- 5- alkene-1- bases, hept-2-ene"-1- bases, oct-2-ene-1- bases and 12-2- alkene-1- bases.Particularly preferred alkenyl is pi-allyl and methylallyl.
Alkynyl refers to the straight or branched alkynyl with 3-20, preferably 3-8, particularly preferred 3-5 carbon atom, and it can be unsubstituted or be replaced by one or more halogens.It is preferred that alkynyl refer to what is connected via saturated carbon atom, that is, the alkynyl with a centre or terminal triple link.The example of alkynyl is propargyl, butyl- 2- alkynes -1- bases, butyl- 3- alkynes -1- bases, amyl- 2-, -3- or -4- alkynes -1- bases, hex- 2-, -3-, -4- or -5- alkynes -1- bases, hept- 2-, -3-, -4-, -5- or -6- alkynes -1- bases and octyl- 2-, -3-, -4-, -5-, -6- or -7- alkynes -1- bases.Particularly preferred alkynyl is propargyl.
Cycloalkyl refers to the straight or branched cycloalkyl with 3-7 carbon atom, and it can be unsubstituted or by the single or multiple substitution of halogen, alkyl or haloalkyl, and alkyl and haloalkyl here preferably comprise 1-4, particularly preferred 1-2 carbon atom.The example of cycloalkyl is cyclopropyl, 2- methylcyclopropyl groups, cyclobutyl, cyclopenta, 2- methylcyclopentyls, 3,4- dimethylcyclopentyls, cyclohexyl, 2- methylcyclohexyls, 4- methylcyclohexyls, 3,4- Dimethylcyclohexyls, 2,4- Dimethylcyclohexyls and suberyl.
Above to the explanation implication of the generic term used in above-mentioned definition unless otherwise specified, it is adaptable to entire disclosure of the invention.
The present invention is more particularly directed to such formula (I) compound, meet the above-mentioned condition enumerated, wherein R1And R2It is hydrogen independently of one another；C1-C20Alkyl, the alkyl can be straight or branched and can be replaced by following group 1-4：Hydroxyl, halogen, alkoxy, halogenated alkoxy, alkyloxy-alkoxy, alkylthio group, halogenated alkylthio, alkyl sulphinyl, alkyl sulphonyl, alkylsulfonyloxy, alkyl-carbonyl, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino, alkoxy carbonyl group, alkyl carbonyl oxy, cycloalkyl, phenyl, naphthyl, phenoxy group, naphthoxy, thiophenyl, naphthalene sulfenyl, benzenesulfonyl, naphthalene sulfonyl base, phenylsulfonyloxy, naphthalene sulfonyl epoxide, benzoyl, naphthoyl, with 5-6 annular atom and 1-2 N, the heteroatomic heteroaryls of O or S or heteroaryloxy, aryl described here and heteroaryl can be replaced by following group list or two：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, nitro, cyano group, phenoxy group, halogenated phenoxy, thiophenyl or halosphenylsulfanyl；C3-C20- alkenyl, it can be straight or branched and can be replaced by halogen 1-4；C3-C20- alkynyl, it can be straight or branched and can be replaced by halogen 1-4；C3-C7- cycloalkyl, it can be replaced by halogen, alkyl or haloalkyl 1-4；The phenyl or naphthyl that can be replaced by following group 1-4：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, cycloalkyl alkoxy, halocycloalkylalkoxy, alkylthio group, halogenated alkylthio, alkylsulfonyloxy, haloalkylsulfonyloxy, halogenated alkoxy sulfonyloxy, alkylamino, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino, nitro, cyano group, trialkylsilkl, phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, with 5-6 annular atom and 1-2 N, the heteroatomic heteroaryls of O or S or heteroaryloxy, wherein described phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, heteroaryl and heteroaryloxy can be replaced as its part of substituent by following group list or two：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, nitro, cyano group, phenoxy group, thiophenyl or halosphenylsulfanyl, cycloalkyl alkoxy or halocycloalkylalkoxy；With 5-6 annular atom and 1-2 N, O or the heteroatomic heteroaryls of S, it can be replaced by following group 1-4：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, cycloalkyl alkoxy, halocycloalkylalkoxy, alkylthio group, halogenated alkylthio, alkylamino, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino, nitro, cyano group, trialkylsilkl, phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, with 5-6 annular atom and 1-2 N, the heteroatomic heteroaryls of O or S or heteroaryloxy, wherein described phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, heteroaryl and heteroaryloxy can be replaced as substituent by following group list or two：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, nitro, cyano group, phenoxy group, thiophenyl, halosphenylsulfanyl, cycloalkyl alkoxy or halocycloalkylalkoxy；R3It is hydrogen, fluorine or methyl；M is 0,1,2,3,4 or 5；N is 0 or 1；And X is oxygen or NR4, wherein R4Hydrogen, can be by the single or multiple substituted C of halogen1-C4Alkyl, C1-C4Alkoxy or two-C1-C4- alkylamino, or can be by the single or multiple substituted phenyl of following group：Halogen, C1-C4- alkyl, halo C1-C4- alkyl, C1-C4- alkoxy, nitro or cyano group.
In view of condition enumerated above, the preferred compound of logical formula (I) is：Wherein, R1And R2It is hydrogen independently of one another；Straight or branched and can be by following group list or dibasic C1-C8- alkyl：Hydroxyl, halogen, C1-C4- alkoxy, halo-C1-C4- alkoxy, C1-C4- alkyloxy-alkoxy, C1-C4- alkylthio group, halo-C1-C4- alkylthio group, C1-C4- alkyl sulphinyl, C1-C4- alkyl sulphonyl, C1-C4- alkylsulfonyloxy, C1-C4- alkyl-carbonyl, two-C1-C4- alkylamino, pyrrolidin-1-yl, piperidino, morpholino, C1-C4- alkoxy carbonyl group, C1-C4- alkyl carbonyl oxy, C3-C6- cycloalkyl, phenyl, naphthyl; phenoxy group, naphthoxy, thiophenyl; naphthalene sulfenyl, benzenesulfonyl, naphthalene sulfonyl base; phenylsulfonyloxy, naphthalene sulfonyl epoxide, benzoyl; naphthoyl; with 5-6 annular atom and 1-2 N, O or the heteroatomic heteroaryls of S or heteroaryloxy, wherein described aryl or heteroaryl can be replaced by following group list or two：Halogen, C1-C4Alkyl, halo-C1-C4- alkyl, C1-C4- alkoxy, halo-C1-C4- alkoxy, C1-C4- alkylthio group, nitro, cyano group, phenoxy group, halogenated phenoxy, thiophenyl or halosphenylsulfanyl；Can be by halogen list or the C of dibasic straight or branched3-C8- alkenyl；Can be by halogen list or the C of dibasic straight or branched3-C8- alkynyl；Can be by halogen, C1-C4- alkyl or halo-C1-C4- alkyl-substituted C3-C7- cycloalkyl；Can be by following group list or dibasic phenyl or naphthyl：Halogen, C1-C4- alkyl, halo-C1-C4- alkyl, C1-C4- alkoxy, halo-C1-C4- alkoxy, C3-C6- cycloalkyl-C1-C4- alkoxy, halo-C1-C4- cycloalkyl-C1-C4- alkoxy, C1-C4- alkylthio group, halo-C1-C4- alkylthio group, C1-C4- alkylsulfonyloxy, halo-C1-C4- alkylsulfonyloxy, halo-C1-C4- alkoxy sulfonyloxy, C1-C4- alkylamino, two-C1-C4- alkylamino, pyrrolidin-1-yl, piperidino, morpholino, nitro, cyano group, three-C1-C4- aIkylsilyl groups; phenyl; phenoxy group; thiophenyl, benzoyl, benzyloxy; phenylamino; naphthyl, with 5-6 annular atom and the heteroatomic heteroaryl of 1-2 N, O or S or heteroaryloxy, wherein the phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, heteroaryl and heteroaryloxy can be replaced as substituent by following group list or two：Halogen, C1-C4- alkyl, halo-C1-C4- alkyl, C1-C4- alkoxy, halo-C1-C4- alkoxy, C1-C4- alkylthio group, nitro, cyano group, phenoxy group, thiophenyl or halosphenylsulfanyl, C3-C6- cycloalkyl-C1-C4- alkoxy or halo-C3-C6- cycloalkyl-C1-C4- alkoxy；With 5-6 annular atom and 1-2 N, O or the heteroatomic heteroaryls of S, it can be replaced by following group list or two：Halogen, C1-C4- alkyl, halo-C1-C4- alkyl, C1-C4- alkoxy, halo-C1-C4- alkoxy, C3-C6- cycloalkyl-C1-C4- alkoxy, halo-C3-C6- cycloalkyl-C1-C4- alkoxy, C1-C4Alkylthio group, halo-C1-C4- alkylthio group, C1-C4- alkylamino, two-C1-C4- alkylamino, pyrrolidin-1-yl, piperidino, morpholino, nitro, cyano group, three-C1-C4- aIkylsilyl groups; phenyl; phenoxy group; thiophenyl, benzoyl, benzyloxy; phenylamino; naphthyl, with 5-6 annular atom and the heteroatomic heteroaryl of 1-2 N, O or S or heteroaryloxy, wherein the phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, heteroaryl and heteroaryloxy can be replaced as substituent by following group list or two：Halogen, C1-C4- alkyl, halo-C1-C4- alkyl, C1-C4- alkoxy, halo-C1-C4- alkoxy, C1-C4- alkylthio group, nitro, cyano group, phenoxy group, thiophenyl, halosphenylsulfanyl, C3-C6- cycloalkyl-C1-C4- alkoxy or halo-C3-C6- cycloalkyl-C1-C4- alkoxy；
R3It is hydrogen, fluorine or methyl,
M is 0,1,2,3 or 4,
N is 0 or 1；And
X is oxygen or NR4, wherein
R4Hydrogen, can be by halogen, C1-C4- alkoxy or two-C1-C4The C of-alkylamino substitution1-C4- alkyl or be can be by halogen, C1-C4- alkyl, halo-C1-C4- alkyl, C1-C4The benzyl of-alkoxy, nitro or cyano group substitution.
R defined above1, R2, R3And R4Preferred meaning be similarly applicable for formula (I) compound subgroup.
In logical formula (I) compound, further preferred compound is：Wherein
a)R3It is hydrogen；
B) m is 0,1,2,3 or 4, particularly preferably 1 or 4；
C) n is 0；
d)R4It is hydrogen；
e)R1And R2It is as defined above, R3It is hydrogen；M is 0,1,2,3 or 4；N is 0 or 1；And X is oxygen or NH；
f)R1And R2It is as defined above；R3It is hydrogen；M is 1 or 4；N is 0；And X is oxygen or NH：
g)R1It is as defined above, R3It is hydrogen and R2It is following group
Figure A9880579500151
Wherein alk is methyl or ethyl and the phenyl ring is substituted or unsubstituted.
In formula (I) compound, particularly preferred single compound is：Wherein R3It is hydrogen, and
a)R1It is hydrogen, R2It is hydrogen, X is oxygen, and m is that 1 and n is 0；
b)R1It is methyl, R2It is methyl, X is oxygen, and m is that 1 and n is 0；
c)R1It is methyl, R2It is phenyl, X is oxygen, and m is that 1 and n is 0；
d)R1It is methyl, R2It is 4- trifluoromethyls, X is oxygen, and m is that 1 and n is 0；
e)R1It is methyl, R2It is 4- nitrobenzophenones, X is oxygen, and m is that 1 and n is 0；
f)R1It is methyl, R2It is 4- tert-butyl-phenyls, X is oxygen, and m is that 1 and n is 0；
g)R1It is phenyl, R2It is phenyl, X is oxygen, and m is that 1 and n is 0；
h)R1It is hydrogen, R2It is phenyl, X is oxygen, and m is that 1 and n is 0；
i)R1It is phenyl, R2It is benzyl, X is oxygen, and m is that 1 and n is 0；
j)R1It is ethyl, R2It is 4- chlorphenyls, X is oxygen, and m is that 1 and n is 0；
k)R1It is hydrogen, R2It is methyl, X is NH, and m is that 1 and n is 0；
l)R1It is methyl, R2It is methyl, X is NH, and m is that 1 and n is 0；
m)R1It is methyl, R2It is phenyl, X is NH, and m is that 1 and n is 0；
n)R1It is methyl, R2It is 3- trifluoromethyls, X is NH, and m is that 1 and n is 0；
O)R1It is methyl, R2It is 4- tert-butyl-phenyls, X is NH, and m is that 1 and n is 0；
p)R1It is phenyl, R2It is phenyl, X is NH, and m is that 1 and n is 0；
q)R1It is hydrogen, R2It is phenyl, X is oxygen, and m is that 1 and n is 0；
r)R1It is phenyl, R2Benzyl, X is NH, and m is that 1 and n is 0；
s)R1It is ethyl, R2It is 4- chlorphenyls, X is NH, and m is that 1 and n is 0；
t)R1It is hydrogen, R2It is hydrogen, X is NH, and m is that 1 and n is 1；
u)R1It is methyl, R2It is methyl, X is NH, and m is that 1 and n is 1；
v)R1It is methyl, R2It is phenyl, X is NH, and m is that 1 and n is 1；
w)R1It is methyl, R2It is 3- trifluoromethyls, X is NH, and m is that 1 and n is 1；
x)R1It is methyl, R2It is 4- tert-butyl-phenyls, X is NH, and m is that 1 and n is 1；
y)R1It is phenyl, R2It is phenyl, X is NH, and m is that 1 and n is 1；
z)R1It is hydrogen, R2It is phenyl, X is oxygen, and m is that 1 and n is 1；
aa)R1It is phenyl, R2It is benzyl, X is NH, and m is that 1 and n is 1；Or
bb)R1It is ethyl, R2It is 4- chlorphenyls, X is NH, and m is that 1 and n is 1.
The present invention further provides the preparation method of logical formula (I) compound, including
A) it is 0 and R to prepare wherein n1, R2, R3, the logical formula (I) compound of X and m as defined in formula (I) above, it is reacted by logical formula (II) compound with logical formula (III) compound, leads to R in formula (II)3With m as defined in formula (I), and Y2It is Cl, Br or OSO2- alkyl；R in logical formula (III)1, R2With X as defined in formula (I)；
Figure A9880579500171
B) it is 0 to prepare wherein n；X is NR4And R1, R2, R3With formula (I) compounds of m as defined in formula (I), it is to be reacted by logical formula (IV) compound with logical formula (V) compound, leads to R in formula (IV)3, R4With m as defined in logical formula (I), the R led in formula (V)1And R2As defined in logical formula (I)；And
Figure A9880579500172
C) it is 1 and R to prepare wherein n1, R2, R3, R4, X and m are as led to the logical formula (I) compound defined in formula (I), and it is reacted by logical formula (VI) compound with logical formula (VII) compound, leads to R in formula (VI)3With m as defined in logical formula (I), the Y led in formula (VII)1It is Cl, Br or OSO2- alkyl and R1, R2With X as defined in logical formula (I).
Figure A9880579500173
Figure A9880579500181
Logical formula (II) and (VI) initiation material are that the known or available method similar to known to is prepared.
The initiation material of logical formula (III) can be with the ketone shown in above-mentioned logical formula (V) and hydrazine, by R4Mono-substituted hydrazine (wherein R4It is as defined above) or azanol react obtain in a per se known way, the ketone shown in its formula of (V) can be obtained with the conventional method for preparing ketone.
The initiation material of logical formula (II) can be as the carboxylic acid halides (wherein Hal is chlorine or bromine) shown in below general formula and by R4(wherein R4It is as defined above) mono-substituted hydrazine reaction obtains.
The initiation material of logical formula (VII) can be obtained by chloroacetic halide (such as chloracetyl chloride) with logical formula (III) compound reaction defined above.
Method a) reaction is carried out preferably in the atent solvent without hydroxyl, in the presence of organic base, organic bases pyridine in this way, DMAP, 4- pyrollidinopyridines, lutidines, collidine, trialkylamine, N, N- dialkyl anilines, or bicyclic non-nucleophilic alkali, such as Isosorbide-5-Nitrae-diazabicyclo [2.2.2] octane (DABCO), 1,5- diazabicyclos [4.3.0] nonyl- 5- alkene (DBN) or the carbon -7- alkene (1,5-5) (DBU) of 1,8- diazabicyclo [5.4.0] 11.The reaction is general to be -30 DEG C~+70 DEG C, is preferably carried out at -10 DEG C~+50 DEG C in temperature.Reacted in the presence of to the inert solvent of reaction or solvent mixture than advantageous.Therefore, suitable solvent is, for example, aliphatic series and aromatic hydrocarbon, such as benzene, toluene, dimethylbenzene, petroleum ether, hexane；Halogenated hydrocarbons such as chlorobenzene, dichloromethane, dichloroethanes, chloroform, carbon tetrachloride, tetrachloro-ethylene；Ether and ether compound such as dialkyl ether (ether, diisopropyl ether, t-butyl methyl ether), methyl phenyl ethers anisole , dioxanes, tetrahydrofuran；Nitrile such as acetonitrile, propionitrile；Esters such as ethyl acetate, propyl acetate or butyl acetate；Ketone such as acetone, metacetone, MEK；And the mutual mixture of these solvents.And the reaction can be carried out in the case of one of above-mentioned alkali excess, or it can also be carried out using second of equivalent instead of alkali under the conditions of logical formula (I) compound is large excess of.And the reaction can be carried out in normal pressure or under elevated pressure or under reduced pressure.
Method b) reaction is carried out advantageously in atent solvent at a temperature of 20 DEG C -150 DEG C, preferably 40 DEG C -120 DEG C, if appropriate, can catalytic amount acid, carry out in the presence of such as acetic acid or p-methyl benzenesulfonic acid.It is preferred that atent solvent be low-level chain triacontanol, particularly methanol and ethanol.
Method c) reaction is carried out advantageously in atent solvent and in the presence of base, if appropriate, can be in catalyst, as carried out in the presence of NaI or CsF, atent solvent preferably is dipolar aprotic solvent such as DMF, dimethyl sulfoxide , dioxanes and tetrahydrofuran.Suitable alkali particularly pyridine, 4- dimethylamino yl pyridines, 4- pyrollidinopyridines, lutidines, Ma Keli, trialkylamine, N, N- dialkyl anilines, or bicyclic non-nucleophilic alkali such as Isosorbide-5-Nitrae-diazabicyclo [2.2.2] octane (DABCO), 1,5- diazabicyclos [4.3.0] nonyl- 5- alkene (DBN) or the carbon -7- alkene (1,5-5) (DBU) of 1,8- diazabicyclo [5.4.0] 11.
Reaction described above and below is all carried out in mode commonly known per se, for example not or it there may suitably be suitable solvent or diluent or its mixture, carried out as required in cooling, at room temperature or under heating condition, temperature range for example at about -80 DEG C to reaction mixture fusing point, carry out at preferably -20 DEG C to about+150 DEG C, and if desired, with closed vessel in superatmospheric pressure, carry out in inert atmosphere and/or in anhydrous conditions.Particularly preferred condition is as described embodiments.
The logical formula (I) compound of the present invention can be well tolerable by warm-blooded animal, fish and plant, and they are useful reactive compounds in pest control field.The reactive compound of the present invention is particularly active to the insect and Araneae run on the valuable plant of tool in agricultural and horticulture and ornamental plant particularly rice, cotton, vegetables and fruit and forestry.Logical formula (I) compound is especially suitable for the insect control of rice, fruits and vegetables, particularly damage the insect of plant, such as bean aphid (Aphis craccivora), brown plant-hopper (Nilaparvata lugens) and rice green leafhopper (Nephotettix cincticeps).The purposes of reactive compound other field of the present invention is to protect the product and material of storage and for toilet, particularly protection pet and useful animals.Logical formula (I) compound is respectively provided with activity to the insect with normal sensitivity and drug resistance of whole or individual development stages.Their effect, such as in terms of insect is destroyed, such as during cast off a skin immediately or merely through a period of time after, or in terms of spawning and/or reduction incubation rate is reduced all be apparent.
Above-mentioned animal pest is for example including those described in European Patent application EP-A-736252.Therefore the present invention is combined with reference to EP-A-736252.
Logical formula (I) compound is especially suitable for use as reactive compound preventing and treating Homoptera (Homoptem) and the insect of Akarina mesh.
Logical formula (I) compound is particularly suitable for preventing and treating the insect of the crops such as cotton, veterinary antibiotics and rice, such as spider mite (spider mites), the caterpillar (caterpillars) of aphid, butterfly and moth, and rice green leafhopper (rice leaf hoppers).It is primarily directed to the preventing and treating full melon mite of spider mite such as apple (panonychus ulmi), aphid such as bean aphid, the caterpillar of butterfly and moth, such as tobacco budworm (Heliothis virescens), and rice green leafhopper, such as brown plant-hopper or rice green leafhopper.
The good insecticidal action of the logical formula (I) compound of the present invention shows at least 50-60% killings rate (death rate) to the insect.
The logical formula (I) compound of the present invention can significantly widen insecticidal range by adding other insecticides and/or acaricide and adapt to specific environment with and containing their compositions.Suitable additive is, for example, the representative of following active ingredient species：Organic phosphorus compound, nitro class phenol and its derivative, formamidine urinate class, carbamates, pyrethroid, chlorohydrocarbon and bacillus thuringiensis class preparation.
Logical formula (I) compound can directly using or be preferably used together with the conven-tional adjuvants of formulation art.Therefore, they can be processed into a known manner such as missible oil, can Direct spraying or dilution solution, dilution emulsion, wettable powder, soluble powder, pulvis, granule or polymer capsule.The similar composition, application method is selected according to the target and current condition to be prevented and treated, is such as sprayed, is atomized, dusts, applies or is applied together with watering pours water.
The formulation (that is, preparation) includes the preparation or composition of reactive compound (I), or the mixture of these reactive compounds and other insecticides or acaricide and suitable solid or liquid additive is all prepared in a known manner, it is for example close to mix and/or grind reactive compound together with auxiliary agent, auxiliary agent such as solvent, solid carrier and appropriate surface active cpd (surfactant).
Suitable auxiliary agent used in the present invention as other auxiliary agents in solvent, solid carrier, surface active cpd, nonionic surface active agent, cationic surface active agent, anionic surfactant or composition be, for example, described in EP-A-736 ' 252.
The insecticidal preparation generally comprises 0.1-99%, particularly 0.1-95% formula (I) reactive compound or these reactive compounds and other insecticides and/or acaricidal mixture and 1-99.9%, particularly 5-99.9% solid or liquid adjuvants, and wherein surfactant typically constitutes from the 0-25%, particularly 0.1-20% of composition (percentage in the case of various is to refer both to percetage by weight).Generally preferably concentrate formulation is as commercially available prod, and terminal user is typically using the dilution preparation for significantly reducing activity compound concentration.Concentration is general between 0.1-1000ppm, preferably between 0.1-500ppm.Amount of application is generally per hectare 1-1000g reactive compounds, preferably per hectare 25-500g.
It is preferred that preparation especially have consisting of (%=percentage by weights)：
Missible oil：
Reactive compound 1-90%, preferably 5-20%
Surfactant 1-30%, preferably 10-20%
Liquid-carrier 5-94%, preferably 70-85%
Pulvis
Reactive compound 0.1-10%, preferably 0.1-1%
Solid carrier 99.9-90%, preferably 99.9-99%
Colloidal suspending agent
Reactive compound 5-75%, preferably 10-50%
Surfactant 1-40%, preferably 2-30%
Water 94-24%, preferably 88-30%
Wettable powder
Reactive compound 0.5-90%, preferably 1-80%
Surfactant 0.5-20%, preferably 1-15%
Solid carrier 5-95%, preferably 15-90%
Granule：
Reactive compound 0.5-30%, preferably 3-15%
Solid carrier 99.5-70%, preferably 97-85%
The preparation can also contain other auxiliary agents such as stabilizer, such as non-epoxidation or epoxidised vegetable oil (such as epoxidised coconut oil, rapeseed oil or soybean oil), defoamer such as silicone oil, preservative, viscosity modifier, adhesive and/or adhesive, and fertilizer or other reactive compounds of special-effect can be obtained.
Following examples only for the explanation present invention, are in no way limiting of the scope of the invention.The temperature for degree Celsius.
Embodiment H1：
Figure A9880579500221
0.73g (10mmol) acetoximes and 1.01g (10mmol) triethylamine are dissolved in 30ml anhydrous benzenes.Resulting solution is stirred about 30 minutes in 5-10 DEG C, 1.68g (10mmol) 6,6- difluoro hex- 5- alkene acyl chlorides (DAHSCI) is added under strong agitation, room temperature is stirred for the mixture 10 hours, then filtered by glass suction filter, rotary evaporator concentration filtrate.The separating obtained crude product of silica gel column chromatography (ethyl acetate: isohexane=20: 80).Obtain nD 20=1.6893 title compound.
Embodiment H2：
Figure A9880579500222
1.5g (7.6mmol) benzophenone hydrazones and 0.77g (7.6mmol) triethylamine are dissolved in 30ml anhydrous benzenes.Resulting solution is mixed about 30 minutes at 5-10 DEG C with 1.29g (7.6mmol) 6,6- difluoro hex- 5- alkene acyl chlorides (DAHSCI) stirring.Room temperature is stirred for the mixture 10 hours, is then filtered by glass suction filter, rotary evaporator concentration gained filtrate.Crude product (ethyl acetate: isohexane=20: 80) obtained by silica gel chromatography.Obtain the title compound that m.p. is 70-71 DEG C.
Embodiment H3：
Figure A9880579500231
0.5g (10mmol) hydrazine hydrate is added to 1.64g (10mmol) 6,6- difluoro hex- 5- e pioic acid methyl esters in the solution of 10ml methanol.Resulting solution is heated to reflux 10 minutes in water-bath, is then concentrated with rotary evaporator.Residue is suspended in 20ml dichloromethane, and the acetaldehyde with 0.445g (10mmol) at 0 DEG C is mixed, and room temperature is stirred for gained mixture 10 hours.Dichloromethane, the separating obtained crude product of silica gel column chromatography (methyl acetate: isohexane=20: 80) is evaporated off.Obtain the title compound that m.p. is 78-79 DEG C.
Embodiment H4：
3.6g (18.4mmol) benzophenone hydrazones and 1.85g (18.3mmol) triethylamine are dissolved in 50ml benzene, and gained mixture is cooled to 5 DEG C.It is sufficiently stirred for down, 2.06g (18.2mmol) chloracetyl chlorides is slowly added dropwise and temperature is always held at 5-10 DEG C.Add after chloracetyl chloride, room temperature continues to stir the mixture 14 hours.Mixture is filtered with glass suction filter and concentrates gained filtrate.With a small amount of isohexane: acetic acid=80: 20 mixture washs gained residue, filtering is simultaneously dried.Obtain the compound that m.p. is 92-93 DEG C.
1.7g (6.2mmol) chloracetyl benzophenone hydrazides, 0.93g (6.2mmol) 6,6- difluoro dissident -5- olefin(e) acids, the mixture of 0.63g (6.2mmol) triethylamines and 0.2g NaI in 10ml dimethylformamides are stirred 14 hours at room temperature.Reaction mixture is poured into ice, with the chloroform recovery mixture, sodium sulphate is dried after gained extract, boils off solvent, the separating obtained crude product of silica gel column chromatography (isohexane: ethyl acetate=80: 20).Obtain nD 20=1.5678 title compound.Embodiment H5：
Figure A9880579500241
0.5g (10mmol) hydrazine hydrate is added to 0.9g (10mmol) glycolic methyl esters in the solution of 10ml methanol.Resulting solution is heated to reflux 10 minutes in water-bath, is then concentrated with rotary evaporator.Gained residue is suspended in 10ml methanol and mixed with 0.58g (10mmol) acetone, the mixture is then stirred at room temperature 10 hours.Methanol is evaporated off, gained residue is suspended in 20ml dichloromethane/tetrahydrofuran.1.5g (10mmol) 6,6- difluoro hex- 5- olefin(e) acids, 406g (10mmol) DCC and 0.1g DMAP are added to the mixture, stirs 14 hours, is filtered by glass suction filter afterwards, gained filtrate is concentrated with rotary evaporator.Crude product (isohexane: ethyl acetate=80: 20) obtained by silica gel chromatography.Obtain nD 20=1.6768 title compound.
The logical formula (I) compound for being listed in table 1-20 can be prepared with similar embodiment H1-H5 mode.Table 1：Compound shown in following formula
Figure A9880579500251
Compound numbers R1     R2The H H1.02 H CH of physical data 1.0131.03            H       C2H51.04            H       C3H7-n1.05            H       C3H7-i1.06            H       C4H9-n1.07            H       C4H9-t1.08            H       C6H13-n1.09            H       C10H21-n1.10            H       CH2C(CH3)31.11            CH3    H1.12            CH3    CH31.13            CH3    C2H51.14            CH3    C3H7-n1.15            CH3    C3H7-i1.16            CH3    C4H9-n1.17            CH3    C4H9- t Compound numbers R1       R2The CH of physical data 1.183      C6H13-n1.19          CH3      C10H21-n1.20          CH3      CH2C(CH3)31.21          CH3      C6H51.22          CH3      C6H4-2-Cl1.23          CH3      C6H4-3-Cl1.24          CH3      C6H4-4-Cl1.25          CH3      C6H4-2-CF31.26          CH3      C6H4-3-CF31.27          CH3      C6H4-4-CF31.28          CH3      C6H4-2-CN1.29          CH3      C6H4-3-CN1.30          CH3      C6H4-4-CN1.31          CH3      C6H4-2-NO21.32          CH3      C6H4-3-NO21.33          CH3      C6H4-4-NO21.34          CH3      C6H4-4-C6H51.35          CH3      C6H4-4-OC6H51.36          CH3      C6H4-4-C(CH3)31.37          CH3      C6H4-4-OCF31.38          CH3      C6H4-4-COOC2H51.39          CH3      C6F51.40          CH3      -C6H2- 3,4,5- (OCH3)3Compound numbers R1       R2The CH of physical data 1.413      1.42            CH3   
Figure A9880579500272
1.43            CH3     
Figure A9880579500273
1.44            C6H5    CF31.45            C6H5    C2H51.46            C6H5    C3H7-n1.47            C6H5    C3H7-i1.48            C6H5    C4H9-t1.49            C6H5    C4H9-n1.50            C6H5The C of cyclopropyl 1.516H5The C of cyclopenta 1.526H5The C of cyclohexyl 1.536H5    C6H51.54            C6H5    C6H4-4-Cl1.55            C6H5    C6H4-4-CF31.56            C6H5    C6H4-4-CN1.57            C6H5    C6H4-4-NO21.58            C6H5    C6H4-4-C6H51.59            C6H5    C6H4-4-OC6H5Compound numbers R1            R2The C of physical data 1.606H5         C6H4-4-C(CH3)31.61             C6H5         C6H4-4-OCF31.62             C6H4-4-Cl    CF31.63             C6H4-4-Cl    C2H51.64             C6H4-4-Cl    C3H7-n1.65             C6H4-4-Cl    C3H7-i1.66             C6H4-4-Cl    C4H9-t1.67             C6H4-4-Cl    C4H9-n1.68             C6H4-4-Cl    CH2C6H51.69             C6H4-4-Cl    CH2C6H4-4-CH31.70             C6H4-4-Cl    C6H4-4-Cl1.71             C6H4-4-Cl    C6H4-4-OH1.72             C6H4-4-Cl    C6H4-2-CH31.73             C6H4-4-Cl    C6H4-2-Cl1.74             C6H4-4-Cl    C6H4-4-Br1.75             C6H4The C of -4-Cl 4- pyridine radicals 1.766H4-4-Cl    C6H4-4-OCH2-C6H4-3-CF31.77             C6H4-4-Cl   
Figure A9880579500281
1.78             H               C6H51.79             C6H5         CH2C6H51.80             C2H5         -C6H4- 4-Cl tables 2：Compound shown in following formula
Figure A9880579500291
Compound numbers R1         R2The H H2.02 H CH of physical data 2.0132.03             H           C2H52.04             H           C3H7-n2.05             H           C3H7-i2.06             H           C4H9-n2.07             H           C4H9-t2.08             H           C6H13-n2.09             H           C10H21-n2.10             H           CH2C(CH3)32.11             CH3        H2.12             CH3        CH32.13             CH3        C2H52.14             CH3        C3H7-n2.15             CH3        C3H7-i2.16             CH3        C4H9-n2.17             CH3        C4H9-t2.18             CH3        C6H13-n2.19             CH3        C10H21-n2.20             CH3        CH2C(CH3)3Compound numbers R1     R2The CH of physical data 2.213    C6H52.22          CH3    C6H4-2-Cl2.23          CH3    C6H4-3-Cl2.24          CH3    C6H4-4-Cl2.25          CH3    C6H4-2-CF32.26          CH3    C6H4-3-CF32.27          CH3    C6H4-4-CF32.28          CH3    C6H4-2-CN2.29          CH3    C6H4-3-CN2.30          CH3    C6H4-4-CN2.31          CH3    C6H4-2-NO22.32          CH3    C6H4-3-NO22.33          CH3    C6H4-4-NO22.34          CH3    C6H4-4-C6H52.35          CH3    C6H4-4-OC6H52.36          CH3    C6H4-4-C(CH3)32.37          CH3    C6H4-4-OCF32.38          CH3    C6H4-4-COOC2H52.39          CH3    C6F52.40          CH3    C6H2- 3,4,5- (OCH3)32.41          CH3   
Figure A9880579500301
Compound numbers R1       R2The CH of physical data 2.423      2.43          CH3     
Figure A9880579500312
2.44          C6H5    CF32.45          C6H5    C2H52.46          C6H5    C3H7-n2.47          C6H5    C3H7-i2.48          C6H5    C4H9-t2.49          C6H5    C4H9-n2.50          C6H5The C of cyclopropyl 2.516H5The C of cyclopenta 2.526H5The C of cyclohexyl 2.536H5    C6H52.54          C6H5    C6H4-4-Cl2.55          C6H5    C6H4-4-CF32.56          C6H5    C6H4-4-CN2.57          C6H5    C6H4-4-NO22.58          C6H5    C6H4-4-C6H52.59          C6H5    C6H4-4-OC6H52.60          C6H5    C6H4-4-C(CH3)32.61          C6H5    C6H4-4-OCF3Compound numbers R1            R2The C of physical data 2.626H4-4-Cl    CF32.63          C6H4-4-Cl    C2H52.64          C6H4-4-Cl    C3H7-n2.65          C6H4-4-Cl    C3H7-i2.66          C6H4-4-Cl    C4H9-t2.67          C6H4-4-Cl    C4H9-n2.68          C6H4-4-Cl    CH2C6H52.69          C6H4-4-Cl    CH2C6H4-4-CH32.70          C6H4-4-Cl    C6H4-4-Cl2.71          C6H4-4-Cl    C6H4-4-OH2.72          C6H4-4-Cl    C6H4-2-CH32.73          C6H4-4-Cl    C6H4-2-Cl2.74          C6H4-4-Cl    C6H4-4-Br2.75          C6H4The C of -4-Cl 4- pyridine radicals 2.766H4-4-Cl    -C6H4-4-OCH2-C6H4-3-CF32.77          C6H4-4-Cl    2.78          H               -C6H52.79          C6H5         CH2C6H52.80          C2H5         -C6H4- 4-Cl tables 3：Compound shown in following formula
Figure A9880579500331
Compound numbers R1      R2The H H3.02 H CH of physical data 3.0133.03             H        C2H53.04             H        C3H7-n3.05             H        C3H7-i3.06             H        C4H9-n3.07             H        C4H9-t3.08             H        C6H13-n3.09             H        C10H21-n3.10             H        CH2C(CH3)33.11             CH3     H3.12             CH3     CH33.13             CH3     C2H53.14             CH3     C3H7-n3.15             CH3     C3H7-i3.16             CH3     C4H9-n3.17             CH3     C4H9-t3.18             CH3     C6H13-n3.19             CH3     C10H21-n3.20             CH3     CH2C(CH3)3Compound numbers R1       R2The CH of physical data 3.213      C6H53.22              CH3      C6H4-2-Cl3.23              CH3      C6H4-3-Cl3.24              CH3      C6H4-4-Cl3.25              CH3      C6H4-2-CF33.26              CH3      C6H4-3-CF33.27              CH3      C6H4-4-CF33.28              CH3      C6H4-2-CN3.29              CH3      C6H4-3-CN3.30              CH3      C6H4-4-CN3.31              CH3      C6H4-2-NO23.32              CH3      C6H4-3-NO23.33              CH3      C6H4-4-NO23.34              CH3      C6H4-4-C6H53.35              CH3      C6H4-4-OC6H53.36              CH3      C6H4-4-C(CH3)33.37              CH3      C6H4-4-OCF33.38              CH3      C6H4-4-COOC2H53.39              CH3      C6F53.40              CH3      C6H2- 3,4,5- (OCH3)33.41              CH3      Compound numbers R1       R2The CH of physical data 3.423     
Figure A9880579500351
3.43              CH3     
Figure A9880579500352
3.44              C6H5    CF33.45              C6H5    C2H53.46              C6H5    C3H7-n3.47              C6H5    C3H7-i3.48              C6H5    C4H9-t3.49              C6H5    C4H9-n3.50              C6H5The C of cyclopropyl 3.516H5The C of cyclopenta 3.526H5The C of cyclohexyl 3.536H5    C6H53.54              C6H5    C6H4-4-Cl3.55              C6H5    C6H4-4-CF33.56              C6H5    C6H4-4-CN3.57              C6H5    C6H4-4-NO23.58              C6H5    C6H4-4-C6H53.59              C6H5    C6H4-4-OC6H53.60              C6H5    C6H4-4-C(CH3)33.61              C6H5    C6H4-4-OCF3Compound numbers R1            R2The C of physical data 3.626H4-4-Cl    CF33.63            C6H4-4-Cl    C2H53.64            C6H4-4-Cl    C3H7-n3.65            C6H4-4-Cl    C3H7-i3.66            C6H4-4-Cl    C4H9-t3.67            C6H4-4-Cl    C4H9-n3.68            C6H4-4-Cl    CH2C6H53.69            C6H4-4-Cl    CH2C6H4-4-CH33.70            C6H4-4-Cl    C6H4-4-Cl3.71            C6H4-4-Cl    C6H4-4-OH3.72            C6H4-4-Cl    C6H4-2-CH33.73            C6H4-4-Cl    C6H4-2-Cl3.74            C6H4-4-Cl    C6H4-4-Br3.75            C6H4The C of -4-Cl 4- pyridine radicals 3.766H4-4-Cl    C6H4-4-OCH2-C6H4-3-CF33.77            C6H4-4-Cl   
Figure A9880579500361
3.78            H               C6H53.79            C6H5         CH2C6H53.80            C2H5         -C6H4- 4-Cl tables 4：Compound shown in following formula
Figure A9880579500371
Compound numbers R1   R2The H H4.2 H CH of physical data 4.13         nD 20=1.68694.3 H C2H54.4           H     C3H7-n4.5           H     C3H7-i4.6           H     C4H9-n4.7           H     C4H9-t4.8           H     C6H13-n4.9           H     C10H21-n4.10          H     CH2C(CH3)34.11          CH3  H4.12          CH3  CH3          nD 20=1.68934.13 CH3  C2H54.14          CH3  C3H7-n4.15          CH3  C3H7-i4.16          CH3  C4H9-n4.17          CH3  C4H9-t4.18          CH3  C6H13-n4.19          CH3  C10H21- n Compound numbers R1     R2The CH of physical data 4.203    CH2C(CH3)34.21          CH3    C6H5                   nD 20=1.507314.22 CH3    C6H4The CH of -2-C1 grease 4.233    C6H4-3-Cl              nD 20=1.68834.24 CH3    C6H4The CH of -4-Cl grease 4.253    C6H4-2-CF3            nD 20=1.46674.26 CH3    C6H4-3-CF3            nD 20=1.67654.27 CH3    C6H4-4-CF34.28          CH3    C6H4-2-CN4.29          CH3    C6H4Amorphous 4.30 CH of -3-CN3    C6H4-4-CN              m.p.：
                                            121-128℃4.31          CH3    C6H4-2-NO2            nD 20=1.68884.32 CH3    C6H4-3-NO2            nD 20=1.68974.33 CH3    C6H4-4-NO2            nD 20=1.68534.34 CH3    C6H4-4-C6H5          m.p.：51-52℃4.35          CH3    C6H4-4-OC6H5The CH of grease 4.363    C6H4-4-C(CH3)3       nD 20=1.67544.37 CH3    C6H4-4-OCF3           nD 20=1.68434.38 CH3    C6H4-4-COOC2H5Amorphous 4.39 CH3    C6F5The CH of grease 4.403    C6H2- 3,4,5- (OCH3)3 nD 20=1.52074.41 CH3   
Figure A9880579500381
Amorphous Compound sequence number R1       R2The CH of physical data 4.423     
Figure A9880579500391
4.43           CH3     
Figure A9880579500392
                                          m.p.：79-81℃4.44           C6H5     CF34.45           C6H5     C2H54.46           C6H5     C3H7-n4.47           C6H5     C3H7The C of-i grease 4.486H5     C4H9-t           nD 20=1.48504.49 C6H5     C4H9-n4.50           C6H5Cyclopropyl nD 20=1.51324.51 C6H5The C of cyclopenta 4.526H5The C of cyclohexyl 4.536H5     C6H5             nD 20=1.55034.54 C6H5     C6H4The C of -4-Cl grease 4.556H5     C6H4-4-CF3      nD 22=1.51304.56 C6H5     C6H4-4-CN4.57           C6H5     C6H4-4-NO2Amorphous 4.58 C6H5     C6H4-4-C6H54.59           C6H5     C6H4-4-OC6H54.60           C6H5     C6H4-4-C(CH3)34.61           C6H5     C6H4-4-OCF3Compound numbers R1            R2The C of physical data 4.626H4-4-Cl    CF3                     nD 20=1.47094.63 C6H4-4-Cl    C2H54.64          C6H4-4-Cl    C3H7-n4.65          C6H4-4-Cl    C3H7-i4.66          C6H4-4-Cl    C4H9-t4.67          C6H4-4-Cl    C4H9-n4.68          C6H4-4-Cl    CH2C6H54.69          C6H4-4-Cl    CH2C6H4-4-CH34.70          C6H4-4-Cl    C6H4-4-Cl              m.p.：66-67℃4.71          C6H4-4-Cl    C6H4-4-OH4.72          C6H4-4-Cl    C6H4-2-CH34.73          C6H4-4-Cl    C6H4-2-Cl4.74          C6H4-4-Cl    C6H4-4-Br4.75          C6H4- 4-Cl 4- pyridine radicals nD 20=1.55754.76 C6H4-4-Cl    C6H4-4-OCH2-C6H4-3-CF34.77          C6H4-4-Cl    4.78          H               C6H5                   nD 20=1.51314.79 C6H5         CH2C6H5               nD 20=1.67444.80 C2H5         -C6H4-4-Cl             nD 20=1.67684.81 CH3            C6H3- 3,5- (CF3)2    nD 20=1.45094.82 cyclopropyl-C6H3-4-Cl             nD 20=1.6820 Compound numbers R1        R2The CH of physical data 4.833                m.p.：
                                                           138-140℃4.84              CH3       
Figure A9880579500412
          nD 23=1.53504.85 CH3       
Figure A9880579500413
         nD 20=1.55684.86 CH3       
Figure A9880579500414
           nD 23=1.47704.87 C2H5     
Figure A9880579500415
          nD 20=1.47684.88 C2H5     
Figure A9880579500416
     nD 23=1.51134.89 CH3       
Figure A9880579500417
         nD 23=1.55104.90 CH3       
Figure A9880579500418
            nD 23=1.5282 Compound numbers R1             R2The CH of physical data 4.913                nD 23=1.51104.92 CH3          
Figure A9880579500422
         m.p.：36-37℃4.93           CH3                        nD 23=1.51754.94-C6H5        C6H4-2-F                    nD 26=1.53904.95-C6H5        C6H3- 2,4-F2               nD 26=1.52674.96-C6H5        C6H4-4-F                    nD 25=1.53434.97-C6H4-4-F    C6H4-4-F                    m.p.：55-57℃4.98           -C6H5        C6H4-3-CF3                 nD 22=1.51434.99-C6H4-3-CF3 C6H4-3-CF3                 nD 22=1.48314.100-C6H5        C6H4-2-Cl                    nD 22=1.55234.101
Figure A9880579500424
                             m.p.：52-54℃4.102          
Figure A9880579500425
                   m.p.：
                                                           136-138℃4.103          -C6H5        -C6H3-4-Cl-3-NO2            m.p.：72-75℃4.104          -C6H5        -C6H4-3-NO2                 nD 22=1.56154.105-C6H5        -C6H4- 2,4-Cl2              nD 22=1.5490 Compound numbers R1         R2- the C of physical data 4.1066H5      -C6H4-4-S-C6H4-4-Cl              nD 23=1.57574.107-C6H5    
Figure A9880579500431
               nD 23=1.50584.108-C6H4-4-   -C6H4-4-O-CH3                      nD 24=1.5578
              OCH34.109             -C6H5                      m.p.：44-46℃4.110             -C6H5                           nD 23=1.50454.111-C6H4-4-F 
Figure A9880579500434
       nD 23=1.50004.112
Figure A9880579500435
                        nD 24=1.6060 tables 5：Compound shown in following formulaCompound numbers R1     R2The H H5.2 H CH of physical data 5.13             m.p.：78-79℃5.3              H       C2H55.4              H       C3H7-n5.5              H       C3H7-i5.6              H       C4H9-n5.7              H       C4H9-t5.8              H       C6H13-n5.9              H       C10H21-n5.10             H       CH2C(CH3)35.11             CH3    H5.12             CH3    CH3              nD 20=1.75895.13 CH3    C2H55.14             CH3    C3H7-n5.15             CH3    C3H7-i5.16             CH3    C4H9-n5.17             CH3    C4H9-t5.18             CH3    C6H13- n Compound numbers R1     R2The CH of physical data 5.193    C10H21-n5.20          CH3    CH2C(CH3)35.21          CH3    C6H5                    m.p.：64-66℃5.22          CH3    C6H4-2-Cl               m.p.：79-82℃5.23          CH3    C6H4-3-Cl               m.p.：75-78℃5.24          CH3    C6H4-4-Cl               m.p.：104-106℃5.25          CH3    C6H4-2-CF3             nD 20=1.49415.26 CH3    C6H4-3-CF3             m.p.：82-83℃5.27          CH3    C6H4-4-CF3             m.p.：68-69℃5.28          CH3    C6H4-2-CN5.29          CH3    C6H4-3-CN               m.p.：123-124℃5.30          CH3    C6H4-4-CN5.31          CH3    C6H4-2-NO2             m.p.：80-84℃5.32          CH3    C6H4-3-NO2             m.p.：129-130℃5.33          CH3    C6H4-4-NO2             m.p.：159-161℃5.34          CH3    C6H4-4-C6H5           m.p.：193-195℃5.35          CH3    C6H4-4-OC6H5          m.p.：108-109℃5.36          CH3    C6H4-4-C(CH3)3        m.p.：106-108℃5.37          CH3    C6H4-4-OCF3            m.p.：93-94℃5.38          CH3    C6H4-4-COOC2H5        m.p.：98-101℃5.39          CH3    C6F5                     m.p.：119-124℃5.40          CH3    C6H2- 3,4,5- (OCH3)3  m.p.：106-108℃5.41          CH3   
Figure A9880579500451
        m.p.：145-146 DEG C of Compound numbers R1          R2The CH of physical data 5.423        
Figure A9880579500461
m.p.：138-140℃5.43             CH3        
Figure A9880579500462
 m.p.：132-133℃5.44             -C6H5      CF35.45             -C6H5      C2H55.46             -C6H5      C3H7-n5.47             -C6H5      C3H7-i5.48             -C6H5      C4H9-t         m.p.：38-39℃5.49             -C6H5      C4H9-n5.50             -C6H5Cyclopropyl nD 20=1.59625.51-C6H5- the C of cyclopenta 5.526H5- the C of cyclohexyl 5.536H5      C6H5           m.p.：70-71℃5.54             -C6H5      C6H4-4-Cl      m.p.：129-131℃5.55             -C6H5      C6H4-4-CF3    m.p.：119-120℃5.56             -C6H5      C6H4-4-CN5.57             -C6H5      C6H4-4-NO2    m.p.：88-90℃5.58             -C6H5      C6H4-4-C6H5  m.p.：130-132℃5.59             -C6H5      C6H4-4-OC6H55.60             -C6H5      C6H4-4-C(CH3)35.61             -C6H5      C6H4-4-OCF3Compound numbers R1                   R2- the C of physical data 5.626H4-4-Cl          CF35.63          -C6H4-4-Cl          C2H55.64          -C6H4-4-Cl          C3H7-n5.65          -C6H4-4-Cl          C3H7-i5.66          -C6H4-4-Cl          C4H9-t5.67          -C6H4-4-Cl          C4H9-n5.68          -C6H4-4-Cl          CH2C6H55.69          -C6H4-4-Cl          CH2C6H4-4-CH35.70          -C6H4-4-Cl          -C6H4-4-Cl                      m.p.：114-116℃5.71          -C6H4-4-Cl          -C6H4-4-OH5.72          -C6H4-4-Cl          -C6H4-2-CH35.73          -C6H4-4-Cl          -C6H4-2-Cl5.74          -C6H4-4-Cl          -C6H4-4-Br5.75          -C6H4- 4-Cl 4- pyridine radicals m.p.：144-148℃5.76          -C6H4-4-Cl          -C6H4-4-OCH2-C6H4-3-CF3- the C of resin-like 5.776H4-4-Cl         
Figure A9880579500471
H-the C of resin-like 5.786H5                           m.p.：60-63℃5.79          -C6H5               -CH2C6H5                       m.p.：95-96℃5.80          -C2H5               -C6H4-4-Cl                      m.p.：106-107℃5.81          -C6H4-4-Cl          -C6H4-4-OSO2N(CH3)2         m.p.：105-115℃5.82         
Figure A9880579500472
                                m.p.：151-155 DEG C of Compound numbers R1                 R2- the C of physical data 5.836H5Cyclopropyl m.p.：80-82℃5.84          -CH3               -C6H3- 3,5- (CF3)2     m.p.：103-105℃5.85          -C6H5             -C6H4-4-F               m.p.：77-78℃5.86          -C6H5             -C6H3- 2,4-F2          m.p.：109-110℃5.87          -C6H5             -C6H4-4-F               m.p.：99-101℃5.88          -C6H4-4-F         -C6H4-4-F               m.p.：76-77℃5.89         
Figure A9880579500481
                             m.p.：130-132℃5.90          -C6H5             -C6H4-3-NO2            m.p.：102-106℃5.91          -C6H5             -C6H4-3-CF3            m.p.：49-50℃5.92          -C6H5            
Figure A9880579500482
                m.p.：81-82℃5.93          -C6H4-3-CF3      -C6H4-3-CF3            m.p.：62-63℃5.94          -C6H4-4-OCH3     -C6H4-4-OCH3           m.p.：82-83℃5.95          -C6H4-4-OCH3     -CH2-C6H4-4-OCH3      m.p.：123-124℃5.96          -C6H5             -C6H4-2-Cl               m.p.：69-70℃5.97          -C6H5             -C6H3- 2,4-Cl2          m.p.：117-118℃5.98          -C6H4-4-N(CH3)2 -C6H4-4-N(CH3)2       m.p.：93-94℃5.99          -C6H5             -C6H4-4-S-C6H4-4-CH3 m.p.：112-113℃5.100         -C6H5                             nD 20=1.5510 Compound numbers R1             R2- the C of physical data 5.1016H5        
Figure A9880579500491
           nD 20=1.5355 tables 6：Compound shown in following formulaComp.No.       R1           R2      phys.data6.1            H             H6.2            H             CH3      nD 20=1,68156.3 H C2H56.4            H             C3H7-n6.5            H             C3H7-i6.6            H             C4H9-n6.7            H             C4H9-t6.8            H             C6H13-n6.9            H             C10H21-n6.10           H             CH2C(CH3)36.11           CH3          H6.12           CH3          CH3Amorphous 6.13 CH3          C2H56.14           CH3          C3H7- n Compound numbers R1     R2The CH of physical data 6.153    C3H7-i6.16          CH3    C4H9-n6.17          CH3    C4H9-t6.18          CH3    C6H13-n6.19          CH3    C10H21-n6.20          CH3    CH2C(CH3)36.21          CH3    C6H5             m.p.：92-94℃6.22          CH3    C6H4-2-Cl        m.p.：58-60℃6.23          CH3    C6H4-3-Cl        m.p.：126-127℃6.24          CH3    C6H4-4-Cl        m.p.：125-127℃6.25          CH3    C6H4-2-CF3      m.p.：62-64℃6.26          CH3    C6H4-3-CF3      m.p.：148-149℃6.27          CH3    C6H4-4-CF3      m.p.：103-104℃6.28          CH3    C6H4-2-CN6.29          CH3    C6H4-3-CN        m.p.：130-131℃6.30          CH3    C6H4-4-CN        m.p.：141-142℃6.31          CH3    C6H4-2-NO2      m.p.：81-84℃6.32          CH3    C6H4-3-NO2      m.p.：150-152℃6.33          CH3    C6H4-4-NO2      m.p.：147-149℃6.34          CH3    C6H4-4-C6H5    m.p.：166-167℃6.35          CH3    C6H4-4-OC6H5   m.p.：100-110℃6.36          CH3    C6H4-4-C(CH3)3 m.p.：157-158℃6.37          CH3    C6H4-4-OCF3     m.p.：114-116℃6.38          CH3    C6H4-4-COOC2H5 m.p.：127-129 DEG C of Compound numbers R1           R2The CH of physical data 6.393          C6F5                     m.p.：73-76℃6.40           CH3          C6H2- 3,4,5- (OCH3)3  m.p.：139-141℃6.41           CH3                 m.p.：142-144℃6.42           CH3                    m.p.：146-148℃6.43           CH3         
Figure A9880579500513
           m.p.：168-170℃6.44           C6H5        CF36.45           C6H5        C2H56.46           C6H5        C3H7-n6.47           C6H5        C3H7-i                   nD 20=1.69786.48 C6H5        C4H9-t                   nD 20=1.69886.49 C6H5        C4H9-n6.50           C6H5Cyclopropyl m.p.：60-62℃6.51           C6H5The C of cyclopenta 6.526H5The C of cyclohexyl 6.536H5        C6H5                     m.p.：.50-53℃6.54           C6H5        C6H4-4-Cl                m.p.：102-102℃6.55           C6H5        C6H4-4-CF36.56           C6H5        C6H4-4-CN6.57           C6H5        C6H4-4-NO2Compound numbers R1                R2The C of physical data 6.586H5             C6H4-4-C6H56.59          C6H5             C6H4-4-OC6H56.60          C6H5             C6H4-4-C(CH3)36.61          C6H5             C6H4-4-OCF36.62          C6H4-4-Cl        CF36.63          C6H4-4-Cl        C2H56.64          C6H4-4-Cl        C3H7-n6.65          C6H4-4-Cl        C3H7-i6.66          C6H4-4-Cl        C4H9-t6.67          C6H4-4-Cl        C4H9-n6.68          C6H4-4-Cl        CH2C6H56.69          C6H4-4-Cl        CH2C6H4-4-CH36.70          C6H4-4-Cl        C6H4-4-Cl             m.p.：73-75℃6.71          C6H4-4-Cl        C6H4-4-OH6.72          C6H4-4-Cl        C6H4-2-CH36.73          C6H4-4-Cl        C6H4-2-Cl6.74          C6H4-4-Cl        C6H4-4-Br6.75          C6H4The C of -4-Cl 4- pyridine radicals 6.766H4-4-Cl        C6H4-4-OCH2-C6H4-3-
                              CF36.77          C6H4-4-Cl       
Figure A9880579500521
6.78          H                   -C6H5                 m.p.：72-75℃6.79          C6H5             -CH2C6H5             m.p.：104-106 DEG C of Compound numbers R1            R2The C of physical data 6.802H5         -C6H4-4-Cl           m.p.：79-80℃6.81          CH3           -C6H3- 3,5- (CF3)2  m.p.：148-150℃6.82          C2H5         -C6H4-4-Cl           m.p.：79-80 DEG C of table 7：Compound shown in following formula
Figure A9880579500531
Compound numbers R1          R2The H H7.02 H CH of physical data 7.0137.03          H            C2H57.04          H            C3H7-n7.05          H            C3H7-i7.06          H            C4H9-n7.07          H            C4H9-t7.08          H            C6H13-n7.09          H            C10H21-n7.10          H            CH2C(CH3)37.11          CH3         H7.12          CH3         CH37.13          CH3         C2H57.14          CH3         C3H7- n Compound numbers R1         R2The CH of physical data 7.153        C3H7-i7.16          CH3        C4H9-n7.17          CH3        C4H9-t7.18          CH3        C6H13-n7.19          CH3        C10H21-n7.20          CH3        CH2C(CH3)37.21          CH3        C6H57.22          CH3        C6H4-2-Cl7.23          CH3        C6H4-3-Cl7.24          CH3        C6H4-4-Cl7.25          CH3        C6H4-2-CF37.26          CH3        C6H4-3-CF37.27          CH3        C6H4-4-CF37.28          CH3        C6H4-2-CN7.29          CH3        C6H4-3-CN7.30          CH3        C6H4-4-CN7.31          CH3        C6H4-2-NO27.32          CH3        C6H4-3-NO27.33          CH3        C6H4-4-NO27.34          CH3        C6H4-4-C6H57.35          CH3        C6H4-4-OC6H57.36          CH3        C6H4-4-C(CH3)37.37          CH3        C6H4-4-OCF37.38          CH3        C6H4-4-COOC2H5Compound numbers R1           R2The CH of physical data 7.393          C6F57.40          CH3          C6H2- 3,4,5- (OCH3)37.41          CH3         
Figure A9880579500551
7.42          CH3          7.43          CH3          7.44          C6H5        CF37.45          C6H5        C2H57.46          C6H5        C3H7-n7.47          C6H5        C3H7-i7.48          C6H5        C4H9-t7.49          C6H5        C4H9-n7.50          C6H5The C of cyclopropyl 7.516H5The C of cyclopenta 7.526H5The C of cyclohexyl 7.536H5        C6H57.54          C6H5        C6H4-4-Cl7.55          C6H5        C6H4-4-CF37.56          C6H5        C6H4-4-CN7.57          C6H5        C6H4-4-NO2Compound numbers R1            R2The C of physical data 7.586H5         C6H4-4-C6H57.59          C6H5         C6H4-4-OC6H57.60          C6H5         C6H4-4-C(CH3)37.61          C6H5         C6H4-4-OCF37.62          C6H4-4-Cl    CF37.63          C6H4-4-Cl    C2H57.64          C6H4-4-Cl    C3H7-n7.65          C6H4-4-Cl    C3H7-i7.66          C6H4-4-Cl    C4H9-t7.67          C6H4-4-Cl    C4H9-n7.68          C6H4-4-Cl    CH2C6H57.69          C6H4-4-Cl    CH2C6H4-4-CH37.70          C6H4-4-Cl    C6H4-4-Cl7.71          C6H4-4-Cl    C6H4-4-OH7.72          C6H4-4-Cl    C6H4-2-CH37.73          C6H4-4-Cl    C6H4-2-Cl7.74          C6H4-4-Cl    C6H4-4-Br7.75          C6H4The C of -4-Cl 4- pyridine radicals 7.766H4-4-Cl    C6H4-4-OCH2-C6H4-3-
                          CF37.77          C6H4-4-Cl   
Figure A9880579500561
7.78          H               C6H57.79          C6H5         CH2C6H5Compound numbers R1      R2The C of physical data 7.802H5   -C6H4- 4-Cl tables 8：Compound shown in following formulaCompound numbers R1    R2The H H8.02 H CH of physical data 8.0138.03          H      C2H58.04          H      C3H7-n8.05          H      C3H7-i8.06          H      C4H9-n8.07          H      C4H9-t8.08          H      C6H13-n8.09          H      C10H21-n8.10          H      CH2C(CH3)38.11          CH3   H8.12          CH3   CH38.13          CH3   C2H58.14          CH3   C3H7-n8.15          CH3   C3H7-i8.16          CH3   C4H9- n Compound numbers R1          R2The CH of physical data 8.173         C4H9-t8.18          CH3         C6H13-n8.19          CH3         C10H21-n8.20          CH3         CH2C(CH3)38.21          CH3         C6H58.22          CH3         C6H4-2-Cl8.23          CH3         C6H4-3-Cl8.24          CH3         C6H4-4-Cl8.25          CH3         C6H4-2-CF38.26          CH3         C6H4-3-CF38.27          CH3         C6H4-4-CF38.28          CH3         C6H4-2-CN8.29          CH3         C6H4-3-CN8.30          CH3         C6H4-4-CN8.31          CH3         C6H4-2-NO28.32          CH3         C6H4-3-NO28.33          CH3         C6H4-4-NO28.34          CH3         C6H4-4-C6H58.35          CH3         C6H4-4-OC6H58.36          CH3         C6H4-4-C(CH3)38.37          CH3         C6H4-4-OCF38.38          CH3         C6H4-4-COOC2H58.39          CH3         C6F58.40          CH3         C6H2- 3,4,3,5- (OCH3)3Compound numbers R1          R2The CH of physical data 8.413        
Figure A9880579500591
8.42          CH3        
Figure A9880579500592
8.43          CH3        
Figure A9880579500593
8.44          C6H5       CF38.45          C6H5       C2H58.46          C6H5       C3H7-n8.47          C6H5       C3H7-i8.48          C6H5       C4H9-t8.49          C6H5       C4H9-n8.50          C6H5The C of cyclopropyl 8.516H5The C of cyclopenta 8.526H5The C of cyclohexyl 8.536H5       C6H58.54          C6H5       C6H4-4-Cl8.55          C6H5       C6H4-4-CF38.56          C6H5       C6H4-4-CN8.57          C6H5       C6H4-4-NO28.58          C6H5       C6H4-4-C6H58.59          C6H5       C6H4-4-OC6H5Compound numbers R1            R2The C of physical data 8.606H5         C6H4-4-C(CH3)38.61          C6H5         C6H4-4-OCF38.62          C6H4-4-Cl    CF38.63          C6H4-4-Cl    C2H58.64          C6H4-4-Cl    C3H7-n8.65          C6H4-4-Cl    C3H7-i8.66          C6H4-4-Cl    C4H9-t8.67          C6H4-4-Cl    C4H9-n8.68          C6H4-4-Cl    CH2C6H58.69          C6H4-4-Cl    CH2C6H4-4-CH38.70          C6H4-4-Cl    C6H4-4-Cl8.71          C6H4-4-Cl    C6H4-4-OH8.72          C6H4-4-Cl    C6H4-2-CH38.73          C6H4-4-Cl    C6H4-2-Cl8.74          C6H4-4-Cl    C6H4-4-Br8.75          C6H4The C of -4-Cl 4- pyridine radicals 8.766H4-4-Cl    C6H4-4-OCH2-C6H4-3-CF38.77          C6H4-4-Cl   
Figure A9880579500601
8.78          H               -C6H58.79          C6H5         -CH2C6H58.80          C2H5         -C6H4- 4-Cl- tables 9：Compound shown in following formula
Figure A9880579500611
Compound numbers R1     R2The H H9.02 H CH of physical data 9.0139.03          H       C2H59.04          H       C3H7-n9.05          H       C3H7-i9.06          H       C4H9-n9.07          H       C4H9-t9.08          H       C6H13-n9.09          H       C10H21-n9.10          H       CH2C(CH3)39.11          CH3    H9.12          CH3    CH39.13          CH3    C2H59.14          CH3    C3H7-n9.15          CH3    C3H7-i9.16          CH3    C4H9-n9.17          CH3    C4H9-t9.18          CH3    C6H13-n9.19          CH3    C10H21-n9.20          CH3    CH2C(CH3)3Compound numbers R1        R2The CH of physical data 9.213       C6H59.22          CH3       C6H4-2-Cl9.23          CH3       C6H4-3-Cl9.24          CH3       C6H4-4-Cl9.25          CH3       C6H4-2-CF39.26          CH3       C6H4-3-CF39.27          CH3       C6H4-4-CF39.28          CH3       C6H4-2-CN9.29          CH3       C6H4-3-CN9.30          CH3       C6H4-4-CN9.31          CH3       C6H4-2-NO29.32          CH3       C6H4-3-NO29.33          CH3       C6H4-4-NO29.34          CH3       C6H4-4-C6H59.35          CH3       C6H4-4-OC6H59.36          CH3       C6H4-4-C(CH3)39.37          CH3       C6H4-4-OCF39.38          CH3       C6H4-4-COOC2H59.39          CH3       C6F59.40          CH3       C6H2- 3,4,5- (OCH3)39.41          CH3      
Figure A9880579500621
Compound numbers R1       R2The CH of physical data 9.423     
Figure A9880579500631
9.43           CH3     
Figure A9880579500632
9.44           C6H5    CF39.45           C6H5    C2H59.46           C6H5    C3H7-n9.47           C6H5    C3H7-i9.48           C6H5    C4H9-t9.49           C6H5    C4H9-n9.50           C6H5The C of cyclopropyl 9.516H5The C of cyclopenta 9.526H5The C of cyclohexyl 9.536H5    C6H59.54           C6H5    C6H4-4-Cl9.55           C6H5    C6H4-4-CF39.56           C6H5    C6H4-4-CN9.57           C6H5    C6H4-4-NO29.58           C6H5    C6H4-4-C6H59.59           C6H5    C6H4-4-OC6H59.60           C6H5    C6H4-4-C(CH3)39.61           C6H5    C6H4-4-OCF3Compound numbers R1                R2The C of physical data 9.626H4-4-Cl        CF39.63          C6H4-4-Cl        C2H59.64          C6H4-4-Cl        C3H7-n9.65          C6H4-4-Cl        C3H7-i9.66          C6H4-4-Cl        C4H9-t9.67          C6H4-4-Cl        C4H9-n9.68          C6H4-4-Cl        CH2C6H59.69          C6H4-4-Cl        CH2C6H4-4-CH39.70          C6H4-4-Cl        C6H4-4-Cl9.71          C6H4-4-Cl        C6H4-4-OH9.72          C6H4-4-Cl        C6H4-2-CH39.73          C6H4-4-Cl        C6H4-2-Cl9.74          C6H4-4-Cl        C6H4-4-Br9.75          C6H4The C of -4-Cl 4- pyridine radicals 9.766H4-4-Cl        -C6H4-4-OCH2-C6H4-3-
                              CF39.77          C6H4-4-Cl       
Figure A9880579500641
9.78          H                   C6H59.79          C6H5             CH2C6H59.80          C2H5             -C6H4- 4-Cl tables 10：Compound shown in following formula
Figure A9880579500651
Compound numbers R1    R2The H H10.02 H CH of physical data 10.01310.03            H      C2H510.04            H      C3H7-n10.05            H      C3H7-i10.06            H      C4H9-n10.07            H      C4H9-t10.08            H      C6H13-n10.09            H      C10H21-n10.10            H      CH2C(CH3)310.11            CH3   H10.12            CH3   CH310.13            CH3   C2H510.14            CH3   C3H7-n10.15            CH3   C3H7-i10.16            CH3   C4H9-n10.17            CH3   C4H9-t10.18            CH3   C6H13-n10.19            CH3   C10H21- n Compound numbers R1     R2The CH of physical data 10.203    CH2C(CH3)310.21       CH3    C6H510.22       CH3    C6H4-2-Cl10.23       CH3    C6H4-3-Cl10.24       CH3    C6H4-4-Cl10.25       CH3    C6H4-2-CF310.26       CH3    C6H4-3-CF310.27       CH3    C6H4-4-CF310.28       CH3    C6H4-2-CN10.29       CH3    C6H4-3-CN10.30       CH3    C6H4-4-CN10.31       CH3    C6H4-2-NO210.32       CH3    C6H4-3-NO210.33       CH3    C6H4-4-NO210.34       CH3    C6H4-4-C6H510.35       CH3    C6H4-4-OC6H510.36       CH3    C6H4-4-C(CH3)310.37       CH3    C6H4-4-OCF310.38       CH3    C6H4-4-COOC2H510.39       CH3    C6F510.40       CH3    C6H2- 3,4,5- (OCH3)310.41       CH3   
Figure A9880579500661
Compound numbers R1            R2The CH of physical data 10.423          
Figure A9880579500671
10.43         CH3          
Figure A9880579500672
10.44         C6H5         CF310.45         C6H5         C2H510.46         C6H5         C3H7-n10.47         C6H5         C3H7-i10.48         C6H5         C4H9-t10.49         C6H5         C4H9-n10.50         C6H5The C of cyclopropyl 10.516H5The C of cyclopenta 10.526H5The C of cyclohexyl 10.536H5         C6H510.54         C6H5         C6H4-4-Cl10.55         C6H5         C6H4-4-CF310.56         C6H5         C6H4-4-CN10.57         C6H5         C6H4-4-NO210.58         C6H5         C6H4-4-C6H510.59         C6H5         C6H4-4-OC6H510.60         C6H5         C6H4-4-C(CH3)310.61         C6H5         C6H4-4-OCF3Compound numbers R1             R2The C of physical data 10.626H4-4-Cl     CF310.63       C6H4-4-Cl     C2H510.64       C6H4-4-Cl     C3H7-n10.65       C6H4-4-Cl     C3H7-i10.66       C6H4-4-Cl     C4H9-t10.67       C6H4-4-Cl     C4H9-n10.68       C6H4-4-Cl     CH2C6H510.69       C6H4-4-Cl     CH2C6H4-4-CH310.70       C6H4-4-Cl     C6H4-4-Cl10.71       C6H4-4-Cl     C6H4-4-OH10.72       C6H4-4-Cl     C6H4-2-CH310.73       C6H4-4-Cl     C6H4-2-Cl10.74       C6H4-4-Cl     C6H4-4-Br10.75       C6H4The C of -4-Cl 4- pyridine radicals 10.766H4-4-Cl     C6H4-4-OCH2-C6H4-3-CF310.77       C6H4-4-Cl    
Figure A9880579500681
10.78       H                C6H510.79       C6H5          CH2C6H510.80       C2H5          -C6H4- 4-Cl tables 11：Compound shown in following formulaCompound numbers R1     R2The H H11.02 H-CH of physical data 11.01311.03         H       -C2H511.04         H       -C3H7-n11.05         H       -C3H7-i11.06         H       -C4H9-n11.07         H       -C4H9-t11.08         H       -C6H13-n11.09         H       -C10H21-n11.10         H       -CH2C(CH3)311.11         CH3    H11.12         CH3    -CH311.13         CH3    -C2H511.14         CH3    -C3H7-n11.15         CH3    -C3H7-i11.16         CH3    -C4H9-n11.17         CH3    -C4H9-t11.18         CH3    -C6H13-n11.19         CH3    -C10H21- n Compound numbers R1          R2The CH of physical data 11.203         -CH2C(CH3)311.21         CH3         -C6H511.22         CH3         -C6H4-2-Cl11.23         CH3         -C6H4-3-Cl11.24         CH3         -C6H4-4-Cl11.25         CH3         -C6H4-2-CF311.26         CH3         -C6H4-3-CF311.27         CH3         -C6H4-4-CF311.28         CH3         -C6H4-2-CN11.29         CH3         -C6H4-3-CN11.30         CH3         -C6H4-4-CN11.31         CH3         -C6H4-2-NO211.32         CH3         -C6H4-3-NO211.33         CH3         -C6H4-4-NO211.34         CH3         -C6H4-4-C6H511.35         CH3         -C6H4-4-OC6H511.36         CH3         -C6H4-4-C(CH3)311.37         CH3         -C6H4-4-OCF311.38         CH3         -C6H4-4-COOC2H511.39         CH3         C6F511.40         CH3         -C6H2- 3,4,5- (OCH3)311.41         CH3         Compound numbers R1            R2The CH of physical data 11.423           11.43         CH3          
Figure A9880579500712
11.44         C6H5         -CF311.45         C6H5         -C2H511.46         C6H5         -C3H7-n11.47         C6H5         -C3H7-i11.48         C6H5         -C4H9-t11.49         C6H5         -C4H9-n11.50         C6H5The C of cyclopropyl 11.516H5The C of cyclopenta 11.526H5The C of cyclohexyl 11.536H5         -C6H511.54         C6H5         -C6H4-4-Cl11.55         C6H5         -C6H4-4-CF311.56         C6H5         -C6H4-4-CN11.57         C6H5         -C6H4-4-NO211.58         C6H5         -C6H4-4-C6H511.59         C6H5         -C6H4-4-OC6H511.60         C6H5         -C6H4-4-C(CH3)311.61         C6H5         -C6H4-4-OCF3Compound numbers R1               R2The C of physical data 11.626H4-4-Cl       -CF311.63         C6H4-4-Cl       -C2H511.64         C6H4-4-Cl       -C3H7-n11.65         C6H4-4-Cl       -C3H7-i11.66         C6H4-4-Cl       -C4H9-t11.67         C6H4-4-Cl       -C4H9-n11.68         C6H4-4-Cl       -CH2C6H511.69         C6H4-4-Cl       -CH2C6H4-4-CH311.70         C6H4-4-Cl       -C6H4-4-Cl11.71         C6H4-4-Cl       -C6H4-4-OH11.72         C6H4-4-Cl       -C6H4-2-CH311.73         C6H4-4-Cl       -C6H4-2-Cl11.74         C6H4-4-Cl       -C6H4-4-Br11.75         C6H4The C of -4-Cl 4- pyridine radicals 11.766H4-4-Cl       -C6H4-4-OCH2-C6H4-3-
                             CF311.77         C6H4-4-Cl      
Figure A9880579500721
11.78         H                  -C6H511.79         C6H5            -CH2C6H511.80         C2H5            -C6H4- 4-Cl tables 12：Compound shown in following formula
Figure A9880579500731
Compound numbers R1    R2The H H12.02 H CH of physical data 12.01312.03         H      C2H512.04         H      C3H7-n12.05         H      C3H7-i12.06         H      C4H9-n12.07         H      C4H9-t12.08         H      C6H13-n12.09         H      C10H21-n12.10         H      CH2C(CH3)312.11         CH3   H12.12         CH3   CH312.13         CH3   C2H512.14         CH3   C3H7-n12.15         CH3   C3H7-i12.16         CH3   C4H9-n12.17         CH3   C4H9-t12.16         CH3   C6H13-n12.19         CH3   C10H21-n12.20         CH3   CH2C(CH3)3Compound numbers R1     R2The CH of physical data 12.213    C6H512.22         CH3    C6H4-2-Cl12.23         CH3    C6H4-3-Cl12.24         CH3    C6H4-4-Cl12.25         CH3    C6H4-2-CF312.26         CH3    C6H4-3-CF312.27         CH3    C6H4-4-CF312.28         CH3    C6H4-2-CN12.29         CH3    C6H4-3-CN12.30         CH3    C6H4-4-CN12.31         CH3    C6H4-2-NO212.32         CH3    C6H4-3-NO212.33         CH3    C6H4-4-NO212.34         CH3    C6H4-4-C6H512.35         CH3    C6H4-4-OC6H512.36         CH3    C6H4-4-C(CH3)312.37         CH3    C6H4-4-OCF312.38         CH3    C6H4-4-COOC2H512.39         CH3    C6F512.40         CH3    C6H2- 3,4,5- (OCH3)312.41         CH3    Compound numbers R1       R2The CH of physical data 12.423     
Figure A9880579500751
12.43         CH3     
Figure A9880579500752
12.44         C6H5    CF312.45         C6H5    C2H512.46         C6H5    C3H7-n12.47         C6H5    C3H7-i12.48         C6H5    C4H9-t12.49         C6H5    C4H9-n12.50         C6H5The C of cyclopropyl 12.516H5The C of cyclopenta 12.526H5The C of cyclohexyl 12.536H5    C6H512.54         C6H5    C6H4-4-Cl12.55         C6H5    C6H4-4-CF312.56         C6H5    C6H4-4-CN12.57         C6H5    C6H4-4-NO212.58         C6H5    C6H4-4-C6H512.59         C6H5    C6H4-4-OC6H512.60         C6H5    C6H4-4-C(CH3)312.61         C6H5    C6H4-4-OCF3Compound numbers R1                R2The C of physical data 12.626H4-4-Cl        CF312.63       C6H4-4-Cl        C2H512.64       C6H4-4-Cl        C3H7-n12.65       C6H4-4-Cl        C3H7-i12.66       C6H4-4-Cl        C4H9-t12.67       C6H4-4-Cl        C4H9-n12.68       C6H4-4-Cl        CH2C6H512.69       C6H4-4-Cl        CH2C6H4-4-CH312.70       C6H4-4-Cl        C6H4-4-Cl12.71       C6H4-4-Cl        C6H4-4-OH12.72       C6H4-4-Cl        C6H4-2-CH312.73       C6H4-4-Cl        C6H4-2-Cl12.74       C6H4-4-Cl        C6H4-4-Br12.75       C6H4The C of -4-Cl 4- pyridine radicals 12.766H4-4-Cl        C6H4-4-OCH2-C6H4-3-
                            CF312.77       C6H4-4-Cl       
Figure A9880579500761
12.78       H                   C6H512.79       C6H5             CH2C6H512.80       C2H5             -C6H4- 4-Cl tables 13：Compound shown in following formulaCompound numbers R1   R2The H H13.02 H CH of physical data 13.01313.03         H      C2H513.04         H      C3H7-n13.05         H      C3H7-i13.06         H      C4H9-n13.07         H      C4H9-t13.08         H      C6H13-n13.09         H      C10H21-n13.10         H      CH2C(CH3)313.11         CH3   H13.12         CH3   CH313.13         CH3   C2H513.14         CH3   C3H7-n13.15         CH3   C3H7-i13.16         CH3   C4H9-n13.17         CH3   C4H9-t13.18         CH3   C6H13-n13.19         CH3   C10H21- n Compound numbers R1         R2The CH of physical data 13.203        CH2C(CH3)313.21          CH3        C6H513.22          CH3        C6H4-2-Cl13.23          CH3        C6H4-3-Cl13.24          CH3        C6H4-4-Cl13.25          CH3        C6H4-2-CF313.26          CH3        C6H4-3-CF313.27          CH3        C6H4-4-CF313.28          CH3        C6H4-2-CN13.29          CH3        C6H4-3-CN13.30          CH3        C6H4-4-CN13.31          CH3        C6H4-2-NO213.32          CH3        C6H4-3-NO213.33          CH3        C6H4-4-NO213.34          CH3        C6H4-4-C6H513.35          CH3        C6H4-4-OC6H513.36          CH3        C6H4-4-C(CH3)313.37          CH3        C6H4-4-OCF313.38          CH3        C6H4-4-COOC2H513.39          CH3        C6F513.40          CH3        C6H2- 3,4,5- (OCH3)313.41          CH3       
Figure A9880579500781
Compound numbers R1           R2The CH of physical data 13.423         
Figure A9880579500791
13.43           CH3          13.44           C6H5        CF313.45           C6H5        C2H513.46           C6H5        C3H7-n13.47           C6H5        C3H7-i13.48           C6H5        C4H9-t13.49           C6H5        C4H9-n13.50           C6H5The C of cyclopropyl 13.516H5The C of cyclopenta 13.526H5The C of cyclohexyl 13.536H5        C6H513.54           C6H5        C6H4-4-Cl13.55           C6H5        C6H4-4-CF313.56           C6H5        C6H4-4-CN13.57           C6H5        C6H4-4-NO213.58           C6H5        C6H4-4-C6H513.59           C6H5        C6H4-4-OC6H513.60           C6H5        C6H4-4-C(CH3)313.61           C6H5        C6H4-4-OCF3Compound numbers R1              R2The C of physical data 13.626H4-4-Cl      CF313.63          C6H4-4-Cl      C2H513.64          C6H4-4-Cl      C3H7-n13.65          C6H4-4-Cl      C3H7-i13.66          C6H4-4-Cl      C4H9-t13.67          C6H4-4-Cl      C4H9-n13.68          C6H4-4-Cl      CH2C6H513.69          C6H4-4-Cl      CH2C6H4-4-CH313.70          C6H4-4-Cl      C6H4-4-Cl13.71          C6H4-4-Cl      C6H4-4-OH13.72          C6H4-4-Cl      C6H4-2-CH313.73          C6H4-4-Cl      C6H4-2-Cl13.74          C6H4-4-Cl      C6H4-4-Br13.75          C6H4The C of -4-Cl 4- pyridine radicals 13.766H4-4-Cl      C6H4-4-OCH2-C6H4-3-
                             CF313.77          C6H4-4-Cl      13.78          H                 C6H513.79          C6H5           CH2C6H513.80          C2H5           -C6H4- 4-Cl tables 14：Compound shown in following formula
Figure A9880579500811
Compound numbers R1        R2The H H14.02 H CH of physical data 14.01314.03         H          C2H514.04         H          C3H7-n14.05         H          C3H7-i14.06         H          C4H9-n14.07         H          C4H9-t14.08         H          C6H13-n14.09         H          C10H21-n14.10         H          CH2C(CH3)314.11         CH3       H14.12         CH3       CH314.13         CH3       C2H514.14         CH3       C3H7-n14.15         CH3       C3H7-i14.16         CH3       C4H9-n14.17         CH3       C4H9-t14.18         CH3       C6H13-n14.19         CH3       C10H21- n Compound numbers R1         R2The CH of physical data 14.203        CH2C(CH3)314.21          CH3        C6H514.22          CH3        C6H4-2-Cl14.23          CH3        C6H4-3-Cl14.24          CH3        C6H4-4-Cl14.25          CH3        C6H4-2-CF314.26          CH3        C6H4-3-CF314.27          CH3        C6H4-4-CF314.28          CH3        C6H4-2-CN14.29          CH3        C6H4-3-CN14.30          CH3        C6H4-4-CN14.31          CH3        C6H4-2-NO214.32          CH3        C6H4-3-NO214.33          CH3        C6H4-4-NO214.34          CH3        C6H4-4-C6H514.35          CH3        C6H4-4-OC6H514.36          CH3        C6H4-4-C(CH3)314.37          CH3        C6H4-4-OCF314.38          CH3        C6H4-4-COOC2H514.39          CH3        C6F514.40          CH3        C6H2- 3,4,5- (OCH3)314.41          CH3       
Figure A9880579500821
Compound numbers R1         R2The CH of physical data 14.423       
Figure A9880579500831
14.43          CH3       14.44          C6H5      CF314.45          C6H5      C2H514.46          C6H5      C3H7-n14.47          C6H5      C3H7-i14.48          C6H5      C4H9-t14.49          C6H5      C4H9-n14.50          C6H5The C of cyclopropyl 14.516H5The C of cyclopenta 14.526H5The C of cyclohexyl 14.536H5      C6H514.54          C6H5      C6H4-4-Cl14.55          C6H5      C6H4-4-CF314.56          C6H5      C6H4-4-CN14.57          C6H5      C6H4-4-NO214.58          C6H5      C6H4-4-C6H514.59          C6H5      C6H4-4-OC6H514.60          C6H5      C6H4-4-C(CH3)314.61          C6H5      C6H4-4-OCF3Compound numbers R1               R2The C of physical data 14.626H4-4-Cl       CF314.63          C6H4-4-Cl       C2H514.64          C6H4-4-Cl       C3H7-n14.65          C6H4-4-Cl       C3H7-i14.66          C6H4-4-Cl       C4H9-t14.67          C6H4-4-Cl       C4H9-n14.68          C6H4-4-Cl       CH2C6H514.69          C6H4-4-Cl       CH2C6H4-4-CH314.70          C6H4-4-Cl       C6H4-4-Cl14.71          C6H4-4-Cl       C6H4-4-OH14.72          C6H4-4-Cl       C6H4-2-CH314.73          C6H4-4-Cl       C6H4-2-Cl14.74          C6H4-4-Cl       C6H4-4-Br14.75          C5H4The C of -4-Cl 4- pyridine radicals 14.766H4-4-Cl       C6H4-4-OCH2-C6H4-3-
                              CF314.77          C6H4-4-Cl       14.78          H                  C6H514.79          C6H5            CH2C6H514.80          C2H5            -C6H4- 4-Cl tables 15：Compound shown in following formula
Figure A9880579500851
Compound numbers R1       R2The H H15.02 H CH of physical data 15.01315.03           H         C2H515.04           H         C3H7-n15.05           H         C3H7-i15.06           H         C4H9-n15.07           H         C4H9-t15.08           H         C6H13-n15.09           H         C10H21-n15.10           H         CH2C(CH3)315.11           CH3      H15.12           CH3      CH315.13           CH3      C2H515.14           CH3      C3H7-n15.15           CH3      C3H7-i15.16           CH3      C4H9-n15.17           CH3      C4H9-t15.18           CH3      C6H13-n15.19           CH3      C10H21-n15.20           CH3      CH2C(CH3)3Compound numbers R1         R2The CH of physical data 15.213        C6H515.22           CH3        C6H4-2-Cl15.23           CH3        C6H4-3-Cl15.24           CH3        C6H4-4-Cl15.25           CH3        C6H4-2-CF315.26           CH3        C6H4-3-CF315.27           CH3        C6H4-4-CF315.28           CH3        C6H4-2-CN15.29           CH3        C6H4-3-CN15.30           CH3        C6H4-4-CN15.31           CH3        C6H4-2-NO215.32           CH3        C6H4-3-NO215.33           CH3        C6H4-4-NO215.34           CH3        C6H4-4-C6H515.35           CH3        C6H4-4-OC6H515.36           CH3        C6H4-4-C(CH3)315.37           CH3        C6H4-4-OCF315.38           CH3        C6H4-4-COOC2H515.39           CH3        C6F515.40           CH3        C6H2- 3,4,5- (OCH3)315.41           CH3       
Figure A9880579500861
Compound numbers R1       R2The CH of physical data 15.423     
Figure A9880579500871
15.43         CH3     
Figure A9880579500872
15.44         C6H5    CF315.45         C6H5    C2H515.46         C6H5    C3H7-n15.47         C6H5    C3H7-i15.48         C6H5    C4H9-t15.49         C6H5    C4H9-n15.50         C6H5The C of cyclopropyl 15.516H5The C of cyclopenta 15.526H5The C of cyclohexyl 15.536H5    C6H515.54         C6H5    C6H4-4-Cl15.55         C6H5    C6H4-4-CF315.56         C6H5    C6H4-4-CN15.57         C6H5    C6H4-4-NO215.58         C6H5    C6H4-4-C6H515.59         C6H5    C6H4-4-OC6H515.60         C6H5    C6H4-4-C(CH3)315.61         C6H5    C6H4-4-OCF3Compound numbers R1               R2The C of physical data 15.626H4-4-Cl       CF315.63         C6H4-4-Cl       C2H515.64         C6H4-4-Cl       C3H7-n15.65         C6H4-4-Cl       C3H7-i15.66         C6H4-4-Cl       C4H9-t15.67         C6H4-4-Cl       C4H9-n15.68         C6H4-4-Cl       CH2C6H515.69         C6H4-4-Cl       CH2C6H4-4-CH315.70         C6H4-4-Cl       C6H4-4-Cl15.71         C6H4-4-Cl       C6H4-4-OH15.72         C6H4-4-Cl       C6H4-2-CH315.73         C6H4-4-Cl       C6H4-2-Cl15.74         C6H4-4-Cl       C6H4-4-Br15.75         C6H4The C of -4-Cl 4- pyridine radicals 15.766H4-4-Cl       C6H4-4-OCH2-C6H4-3-
                             CF315.77         C6H4-4-Cl       15.78         H                  -C6H515.79         C6H5            CH2C6H515.80         C2H5            -C6H44-Cl tables 16：Compound shown in following formula
Figure A9880579500891
Compound numbers R1      R2The H H16.02 H CH of physical data 16.01316.03           H        C2H516.04           H        C3H7-n16.05           H        C3H7-i16.06           H        C4H9-n16.07           H        C4H9-t16.08           H        C6H13-n16.09           H        C10H21-n16.10           H        CH2C(CH3)316.11           CH3     H16.12           CH3     CH316.13           CH3     C2H516.14           CH3     C3H7-n16.15           CH3     C3H7-i16.16           CH3     C4H9-n16.17           CH3     C4H9-t16.18           CH3     C6H13-n16.19           CH3     C10H21- n Compound numbers R1        R2The CH of physical data 16.203       CH2C(CH3)316.21           CH3       C6H516.22           CH3       C6H4-2-Cl16.23           CH3       C6H4-3-Cl16.24           CH3       C6H4-4-Cl16.25           CH3       C6H4-2-CF316.26           CH3       C6H4-3-CF316.27           CH3       C6H4-4-CF316.28           CH3       C6H4-2-CN16.29           CH3       C6H4-3-CN16.30           CH3       C6H4-4-CN16.31           CH3       C6H4-2-NO216.32           CH3       C6H4-3-NO216.33           CH3       C6H4-4-NO216.34           CH3       C6H4-4-C6H516.35           CH3       C6H4-4-OC6H516.36           CH3       C6H4-4-C(CH3)316.37           CH3       C6H4-4-OCF316.38           CH3       C6H4-4-COOC2H516.39           CH3       C6F516.40           CH3       C6H2- 3,4,5- (OCH3)316.41           CH3      
Figure A9880579500901
Compound numbers R1           R2The CH of physical data 16.423         
Figure A9880579500911
16.43           CH3          16.44           C6H5        CF316.45           C6H5        C2H516.46           C6H5        C3H7-n16.47           C6H5        C3H7-i16.48           C6H5        C4H9-t16.49           C6H5        C4H9-n16.50           C6H5The C of cyclopropyl 16.516H5The C of cyclopenta 16.526H5The C of cyclohexyl 16.536H5        C6H516.54           C6H5        C6H4-4-Cl16.55           C6H5        C6H4-4-CF316.56           C6H5        C6H4-4-CN16.57           C6H5        C6H4-4-NO216.58           C6H5        C6H4-4-C6H516.59           C6H5        C6H4-4-OC6H516.60           C6H5        C6H4-4-C(CH3)316.61           C6H5        C6H4-4-OCF3Compound numbers R1              R2The C of physical data 16.626H4-4-Cl      CF316.63          C6H4-4-Cl      C2H516.64          C6H4-4-Cl      C3H7-n16.65          C6H4-4-Cl      C3H7-i16.66          C6H4-4-Cl      C4H9-t16.67          C6H4-4-Cl      C4H9-n16.68          C6H4-4-Cl      CH2C6H516.69          C6H4-4-Cl      CH2C6H4-4-CH316.70          C6H4-4-Cl      C6H4-4-Cl16.71          C6H4-4-Cl      C6H4-4-OH16.72          C6H4-4-Cl      C6H4-2-CH316.73          C6H4-4-Cl      C6H4-2-Cl16.74          C6H4-4-Cl      C6H4-4-Br16.75          C6H4The C of -4-Cl 4- pyridine radicals 16.766H4-4-Cl      C6H4-4-OCH2-C6H4-3-
                             CF316.77          C6H4-4-Cl     
Figure A9880579500921
16.78          H                 C6H516.79          C6H5           CH2C6H516.80          C2H5           -C6H4- 4-Cl tables 17：Compound shown in following formulaCompound numbers R1    R2The H H17.02 H CH of physical data 17.01317.03          H      C2H517.04          H      C3H7-n17.05          H      C3H7-i17.06          H      C4H9-n17.07          H      C4H9-t17.08          H      C6H13-n17.09          H      C10H21-n17.10          H      CH2C(CH3)317.11          CH3   H17.12          CH3   CH317.13          CH3   C2H517.14          CH3   C3H7-n17.15          CH3   C3H7-i17.16          CH3   C4H9-n17.17          CH3   C4H9-t17.18          CH3   C6H13-n17.19          CH3   C10H21- n Compound numbers R1     R2The CH of physical data 17.203    CH2C(CH3)317.21          CH3    C6H517.22          CH3    C6H4-2-Cl17.23          CH3    C6H4-3-Cl17.24          CH3    C6H4-4-Cl17.25          CH3    C6H4-2-CF317.26          CH3    C6H4-3-CF317.27          CH3    C6H4-4-CF317.28          CH3    C6H4-2-CN17.29          CH3    C6H4-3-CN17.30          CH3    C6H4-4-CN17.31          CH3    C6H4-2-NO217.32          CH3    C6H4-3-NO217.33          CH3    C6H4-4-NO217.34          CH3    C6H4-4-C6H517.35          CH3    C6H4-4-OC6H517.36          CH3    C6H4-4-C(CH3)317.37          CH3    C6H4-4-OCF317.38          CH3    C6H4-4-COOC2H517.39          CH3    C6F517.40          CH3    -C6H2- 3,4,5- (OCH3)317.41          CH3   
Figure A9880579500941
Compound numbers R1          R2The CH of physical data 17.423         17.43          CH3         17.44          C6H5       CF317.45          C6H5       C2H517.46          C6H5       C3H7-n17.47          C6H5       C3H7-i17.48          C6H5       C4H9-t17.49          C6H5       C4H9-n17.50          C6H5The C of cyclopropyl 17.516H5The C of cyclopenta 17.526H5The C of cyclohexyl 17.536H5       C6H517.54          C6H5       C6H4-4-Cl17.55          C6H5       C6H4-4-CF317.56          C6H5       C6H4-4-CN17.57          C6H5       C6H4-4-NO217.58          C6H5       C6H4-4-C6H517.59          C6H5       C6H4-4-OC6H517.60          C6H5       C6H4-4-C(CH3)317.61          C6H5       C6H4-4-OCF3Compound numbers R1            R2The C of physical data 17.626H4-4-Cl    CF317.63          C6H4-4-Cl    C2H517.64          C6H4-4-Cl    C3H7-n17.65          C6H4-4-Cl    C3H7-i17.66          C6H4-4-Cl    C4H9-t17.67          C6H4-4-Cl    C4H9-n17.68          C6H4-4-Cl    CH2C6H517.69          C6H4-4-Cl    CH2C6H4-4-CH317.70          C6H4-4-Cl    C6H4-4-Cl17.71          C6H4-4-Cl    C6H4-4-OH17.72          C6H4-4-Cl    C6H4-2-CH317.73          C6H4-4-Cl    C6H4-2-Cl17.74          C6H4-4-Cl    C6H4-4-Br17.75          C6H4The C of -4-Cl 4- pyridine radicals 17.766H4-4-Cl    C6H4-4-OCH2-C6H4-3-CF317.77          C6H4-4-Cl   
Figure A9880579500961
17.78          H               C6H517.79          C6H5         CH2C6H517.80          C2H5         -C6H4- 4-Cl tables 18：Compound shown in following formula
Figure A9880579500971
Compound numbers R1    R2The H H18.02 H CH of physical data 18.01318.03           H      C2H518.04           H      C3H7-n18.05           H      C3H7-i18.06           H      C4H9-n18.07           H      C4H9-t18.08           H      C6H13-n18.09           H      C10H21-n18.10           H      CH2C(CH3)318.11           CH3   H18.12           CH3   CH318.13           CH3   C2H518.14           CH3   C3H7-n18.15           CH3   C3H7-i18.16           CH3   C4H9-n18.17           CH3   C4H9-t18.18           CH3   C6H13-n18.19           CH3   C10H21- n Compound numbers R1       R2The CH of physical data 18.203      CH2C(CH3)318.21           CH3      C6H518.22           CH3      C6H4-2-Cl18.23           CH3      C6H4-3-Cl18.24           CH3      C6H4-4-Cl18.25           CH3      C6H4-2-CF318.26           CH3      C6H4-3-CF318.27           CH3      C6H4-4-CF318.28           CH3      C6H4-2-CN18.29           CH3      C6H4-3-CN18.30           CH3      C6H4-4-CN18.31           CH3      C6H4-2-NO218.32           CH3      C6H4-3-NO218.33           CH3      C6H4-4-NO218.34           CH3      C6H4-4-C6H518.35           CH3      C6H4-4-OC6H518.36           CH3      C6H4-4-C(CH3)318.37           CH3      C6H4-4-OCF318.38           CH3      C6H4-4-COOC2H518.39           CH3      C6F518.40           CH3      C6H2- 3,4,5- (OCH3)318.41           CH3     
Figure A9880579500981
Compound numbers R1          R2The CH of physical data 18.423        
Figure A9880579500991
18.43          CH3        
Figure A9880579500992
18.44          C6H5       CF318.45          C6H5       C2H518.46          C6H5       C3H7-n18.47          C6H5       C3H7-i18.48          C6H5       C4H9-t18.49          C6H5       C4H9-n18.50          C6H5The C of cyclopropyl 18.516H5The C of cyclopenta 18.526H5The C of cyclohexyl 18.536H5       C6H518.54          C6H5       C6H4-4-Cl18.55          C6H5       C6H4-4-CF318.56          C6H5       C6H4-4-CN18.57          C6H5       C6H4-4-NO218.58          C6H5       C6H4-4-C6H518.59          C6H5       C6H4-4-OC6H518.60          C6H5       C6H4-4-C(CH3)3Compound numbers R1             R2The C of physical data 18.616H5          C6H4-4-OCF318.62           C6H4-4-Cl     CF318.63           C6H4-4-Cl     C2H518.64           C6H4-4-Cl     C3H7-n18.65           C6H4-4-Cl     C3H7-i18.66           C6H4-4-Cl     C4H9-t18.67           C6H4-4-Cl     C4H9-n18.68           C6H4-4-Cl     CH2C6H518.69           C6H4-4-Cl     CH2C6H4-4-CH318.70           C6H4-4-Cl     C6H4-4-Cl18.71           C6H4-4-Cl     C6H4-4-OH18.72           C6H4-4-Cl     C6H4-2-CH318.73           C6H4-4-Cl     C6H4-2-Cl18.74           C6H4-4-Cl     C6H4-4-Br18.75           C6H4The C of -4-Cl 4- pyridine radicals 18.766H4-4-Cl     C6H4-4-OCH2-C6H4-3-
                             CF318.77           C6H4-4-Cl    
Figure A9880579501001
18.78           H                C6H518.79           C6H5          CH2C6H518.80           C2H5          -C6H4- 4-Cl tables 19：Compound shown in following formula
Figure A9880579501011
Compound numbers R1           R2- the C of X n physical datas 19.16H5       -C6H5         NH   019.2            -C6H5       -C6H5         NH   1     m.p.：92-93℃19.3            -C6H5       -C6H5         NH   219.4            -C6H5       -C6H5         NH   319.5            -C6H5       -C6H5         NH   419.6            -C6H5       -C6H5         NH   519.7            -C6H5       -C6H5         O    019.8            -C6H5       -C6H5Amorphous 19.9-the C of O 16H5       -C6H5         O    219.10           -C6H5       -C6H5         O    319.11           -C6H5       -C6H5         O    419.12           -C6H5       -C6H4-4-Cl    O    519.13           CH3          -C6H4-4-Cl    NH   019.14           CH3          -C6H4-4-Cl    NH   119.15           CH3          -C6H4-4-Cl    NH   219.16           CH3          -C6H4-4-Cl    NH   319.17           CH3          -C6H4-4-Cl    NH   419.18           CH3          -C6H4-4-Cl    NH   519.19           CH3          -C6H4The Compound numbers R of -4-Cl O 01            R2The CH of X n physical datas 19.203           -C6H4-4-Cl    O    119.21          CH3           -C6H4-4-Cl    O    219.22          CH3           -C6H4-4-Cl    O    319.23          CH3           -C6H4-4-Cl    O    419.24          CH3           -C6H4-4-Cl    O    519.25          -C6H4-4-Cl   -C6H4-4-Cl    NH   119.26          -C6H4-4-Cl   -C6H4The tables 20 of -4-Cl O 1：Compound shown in following formula
Figure A9880579501021
Compound numbers R1             R2- the C of X n physical datas 20.16H5         -C6H5    NH    020.2           -C6H5         -C6H5    NH    1    m.p.：89-100℃20.3           -C6H5         -C6H5    NH    220.4           -C6H5         -C6H5    NH    320.5           -C6H5         -C6H5    NH    420.6           -C6H5         -C6H5    NH    520.7           -C6H5         -C6H5    O     020.8           -C6H5         -C6H5    O     1     nD 20=1.553020.9-C6H5         -C6H5    O     220.10          -C6H5         -C6H5The Compound numbers R of O 31            R2- the C of X n physical datas 20.116H5        -C6H5         O    420.12         -C6H5        -C6H4-4-Cl    O    520.13         CH3           -C6H4-4-Cl    NH   020.14         CH3           -C6H4-4-Cl    NH   120.15         CH3           -C6H4-4-Cl    NH   220.16         CH3           -C6H4-4-Cl    NH   320.17         CH3           -C6H4-4-Cl    NH   420.18         CH3           -C6H4-4-Cl    NH   520.19         CH3           -C6H4-4-Cl    O    020.20         CH3           -C6H4-4-Cl    O    120.21         CH3           -C6H4-4-Cl    O    220.22         CH3           -C6H4-4-Cl    O    320.23         CH3           -C6H4-4-Cl    O    420.24         CH3           -C6H4-4-Cl    O    520.25         -C6H4-4-Cl   -C6H4-4-Cl    NH   120.26         -C6H4-4-Cl   -C6H4-4-Cl    O    1
Biological test example
Embodiment B1：To tobacco budworm (Heliothis virescens) ovicidal action
The tobacco budworm ovum produced on filter paper is simply immersed in the acetone/water testing liquid containing 400ppm reactive compounds to be measured.Hatch ovum in Petri dish after testing liquid airing.The incubation rate percentage for assessing these ovum is compared after 6 days with untreated compare (hatching reduces %).
In this experiment, table 1-20 compound is highly effective to tobacco budworm.Particularly compound 4.80,4.53,4.78,4.12,4,21,4.79,4.02,4.36,4.26,5.76,5.77,5.53,5.21,5.78,5.02,5.12,5.79,5.36,5.26,5.80,6.53,6.21,6.78,6.79,6.12,6.02,6.36,6.26 and 6.80, exhibit more than 80% activity.
Embodiment B2：To brown plant-hopper (Nilaparvata lugens) activity
Rice plants are handled with the aqueous emulsifying spray liquid containing 400ppm reactive compounds of the present invention.After layer of spraying is dried, the second of brown plant-hopper and third-instar larvae are migrated into (populated) to rice plants.After 21 days, the experiment is assessed.The reduction percentage (active %) of colony is determined by comparing leafhopper (loeaf hoppers) number of the processing with being survived on untreated plant.
In this experiment, table 1-20 compound is highly effective to brown plant-hopper.Particularly compound 4.80,4.53,4.78,4.12,4.21,4.79,4.02,4.36,4.26,5.76,5.77,5.53,5.21,5.78,5.02,5.12,5.79,5.36,5.26,5.80,6.53,6.21,6.78,6.79,6.12,6.02,6.36,6.26 and 6.80, exhibit more than 80% activity.
Embodiment B3：To the activity with chrysomelid (Diabrotica balteata) larva of spot cucumber
Corn seedling is handled with the aqueous emulsifying spray liquid containing 400ppm reactive compounds of the present invention.After layer of spraying is dried, 10 are lived in concentrated communities on corn seedling with the second chrysomelid instar larvae of spot cucumber and is put into plastic containers.After 6 days, the experiment is assessed.The reduction percentage (active %) of colony is determined by comparing the quantity of processing and dead larvae on untreated plant.
In this experiment, table 1-20 compound is chrysomelid highly effective to band spot cucumber.Particularly compound 4.80,4.53,4.78,4.12,4.21,4.79,4.02,4.36,4.26,5.76,5.77,5.53,5.21,5.78,5.02,5.12,5.79,5.36,5.26,6.53,6.21,6.78,6.79,6.12,6.02,6.26 and 6.80, exhibit more than 80% activity.
Embodiment B4：To two-spotted spider mite (Tetranychus urticae) activity
Tolerance of Kidney Bean Seedlings is lived in concentrated communities behind the hybrid colony of two-spotted spider mite, 1 day with the aqueous emulsifying spray liquid sprinkling containing 400ppm reactive compounds of the present invention.Then plant is hatched 6 days at 25 DEG C, is estimated afterwards.The reduction percentage (active %) of colony is determined by comparing processing with ovum, larva and the quantity of adult dead on untreated plant.
In this experiment, table 1-20 compound is highly effective to two-spotted spider mite.Particularly compound 4.80,4.53,4.78,4.12,4.21,4.79,4.02,4.36,4.26,5.76,5.77,5.53,5.21,5.78,5.02,5.12,5.79,5.36,5.26,5.80,6.53,6.21,6.78,6.12,6.02,6.36,6.26 and 6.80, exhibit more than 80% activity.
Embodiment B5：To the activity of extra large spodoptera (Spodoptera littoralis) caterpillar
Soya bean seedling plants are sprayed with the aqueous emulsifying spray liquid containing 400ppm reactive compounds of the present invention.After layer of spraying is dried, the 3rd age caterpillar of 10 extra large spodopteras is lived in concentrated communities on soybean plant strain and is put into plastic containers.After 3 days, the experiment is assessed.The reduction percentage (active %) of colony and feeding damage is determined by being respectively compared processing with the quantity and feeding damage (feeding damage) of the dead caterpillars on untreated plant.
In this experiment, table 1-20 compound is highly effective to extra large spodoptera.Particularly compound 4.80,4.53,4.12,4.21,4.36,5.77,5.53,5.21,5.78,5.79,5.36,5.26,5.80,6.53,6.21,6.12,6.02,6.36,6.26 and 6.80, exhibit more than 80% activity.
Embodiment B6：To diamond-back moth caterpillar (Plutella xylostella) activity
Broccoli seedling plants are sprayed with the aqueous emulsifying spray liquid containing 400ppm reactive compounds of the present invention.After layer of spraying is dried, the 3rd age caterpillar of 10 diamond-back moths is lived in concentrated communities on broccoli plant and is put into plastic containers.After 3 days, the experiment is assessed.The reduction percentage (active %) of colony and feeding damage is determined by being respectively compared processing with the quantity and feeding damage of the dead caterpillars on untreated plant.
In this experiment, table 1-20 compound is highly effective to diamond-back moth.Particularly compound 4.80,4.53,4.78,4.12,4.21,4.79,4.02,4.36,4.26,5.77,5.53,5.78,5.36,5.26,5.80,6.53,6.21,6.78,6.12,6.02 and 6.80, shows the activity more than 80%.
Embodiment B7：To bean aphid (Aphis craccivora) activity
Pea seedling is infected with bean aphid, is then sprayed with the spray liquid containing 400ppm inventive compounds, and in 20 DEG C of hatchings.Respectively after 3 and 6 days, the experiment is assessed.Determine that colony reduces percentage (active %) by the quantity for comparing processing and the dead leaf stalk (leaf spars) on untreated plant.
In this experiment, table 1-20 compound is highly effective to bean aphid.Particularly compound 4.80,4.53,4.78,4.12,4.21,4.79,4.36,4.26,5.77,5.53,5.21,5.78,5.26,5.80,6.53,6.21,6.78,6.12,6.02 and 6.80, shows the activity more than 80%.
Embodiment B8：To black peach aphid (Mvzus persicae) activity
Pea seedling is infected with black peach aphid, is then sprayed with the spray liquid containing 400ppm inventive compounds, and in 20 DEG C of hatchings.Respectively after 3 and 6 days, the experiment is assessed.Determine that colony reduces percentage (active %) by comparing the quantity of processing and the dead aphid on untreated plant.
In this experiment, table 1-20 compound is highly effective to black peach aphid.Particularly compound 4.80,4.53,4.78,4.12,4.21,4.79,4.36,4.26,5.21,5.78,5.26,5.80,6.53,6.21,6.78,6.12,6.02 and 6.80, shows the activity more than 80%.
Embodiment B9：To black peach aphid (Myzus persicae) systemic action
Pea seedling is infected with black peach aphid, then its root is placed in the spray liquid containing 400ppm reactive compounds of the present invention, and seedling is cultivated at 20 DEG C.Respectively after 3 and 6 days, the experiment is assessed.Determine that colony reduces percentage (active %) by the quantity of the dead aphid in control treatment and untreated plant.
In this experiment, table 1-20 compound is highly effective to black peach aphid.Particularly compound 4.80,4.53,4.78,4.12,4.21,4.79,4.02,4.36,5.21,5.78,5.02,5.12,6.21,6.78,6.79 and 6.80, shows the activity more than 80%.
Embodiment B10：Ovicidal/larva effect to tobacco budworm (Heliothis viresens)
The tobacco budworm ovum produced on cotton is sprayed with the aqueous emulsifying spray liquid containing 400ppm reactive compounds of the present invention.After 8 days, batch compare with untreated compare, assess the incubation rate and caterpillar survival rate percentage of ovum (colony reduces %).
In this experiment, table 1-20 compound is highly effective to tobacco budworm.Particularly compound 4.80,4.53,4.78,4.12,4.21,4.79,4.02,4.36,4.26,5.76,5.77,5.53,5.21,5.78,5.02,5.12,5.79,5.36,5.26,5.80,6.53,6.21,6.78,6.79,6.12,6.02,6.36,6.26 and 6.80, exhibit more than 80% activity.
Embodiment B11：To two-spotted spider mite (Tetranychus urticae) ovicidal action
Female two-spotted spider mite is lived in concentrated communities on soybean seedling plant and is removed in after 24 hours.The plant for living in concentrated communities ovum is sprayed with the aqueous emulsifying spray liquid containing 400ppm reactive compounds of the present invention.Then by the hatching 6 days of 25 DEG C of plant.Then, it is estimated.Compare ovum, larva and the quantity of adult dead on the plant of untreated plant and processing to determine the percentage (active %) of colony's reduction.
In this experiment, table 1-20 compound is highly effective to two-spotted spider mite.Particularly compound 4.53,4.78,4.12,4.21,4.79,4.02,4.36,4.26,5.76,5.77,5.53,5.21,5.78,5.12,5.79,5.36,5.26,5.80,6.53,6.21,6.78,6.12,6.02,6.36,6.26 and 6.80, show the activity more than 80%.
Embodiment B12：To the activity (anti-organic phosphates (OP) and carbamates (Carb.)) of the full melon mite of apple (Panonychus ulmi)
The full melon mite adult of female apple is lived in concentrated communities on apple seedling.After 7 days, infected plant is sprayed to dropping liquid with the aqueous emulsifying spray liquid containing the compounds of this invention to be measured 400ppm.The experiment is assessed after 14 days.Compare the quantity of dead spider mite on untreated plant and processing plant to determine that colony reduces percentage (active %).
In this experiment, table 1-20 compound is highly effective.Particularly compound 4.53,4.78,4.12,4.21,4.79,4.36,4.26,5.76,5.77,5.53,5.21,5.78,5.12,5.79,5.36,5.26,5.80,6.53,6.21,6.78,6.12,6.02,6.36,6.26 and 6.80, shows the activity more than 80%.

Claims (19)

1. the compound shown in the free or logical formula (I) of salt form：
Figure A9880579500021
Wherein R1And R2It is hydrogen independently of one another；Or substituted or unsubstituted alkyl,
Figure A9880579500022
Aryl, cycloalkyl, alkenyl or alkynyl；R3It is hydrogen, fluorine or methyl；M is 0,1,2,3,4 or 5；N is 0 or 1；X is oxygen or NR4；And R4It is hydrogen, or substituted or unsubstituted C1-C6Alkyl or benzyl, and if appropriate, E/Z isomers, E/Z isomers mixture and/or the dynamic isomer of its possible free or salt form, condition is：If a) X is oxygen and R1And R2When being hydrogen or substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heteroaryl independently of one another, R3It is not hydrogen or fluorine and m and n can not be while be zero；If b) R4It is hydrogen and R1And R2When being hydrogen or substituted or unsubstituted alkyl, aryl or heteroaryl independently of one another, R3It is not hydrogen or fluorine and m and n can not be while be zero；If c) R1And R2One of be that when can be substituted or unsubstituted phenyl with or without the 4- alkylsulfonyloxyphenyls of other substituents, 4- haloalkylsulfonyloxys phenyl or 4- halogenated alkoxies oxyphenyl and another substituent, m be 0,1 or 2 and R4It is hydrogen, alkyl or haloalkyl；If d) R1And R2One of be that when can be substitution or unsubstituted phenyl with or without the 4- perhaloalkoxy groups phenyl and another substituent of other substituents, m be 0,1 or 2 and R4It is not hydrogen, alkyl or haloalkyl and n is not zero.
2. compound according to claim 1, the compound is free form.
3. compound according to claim 1, wherein R1And R2It is hydrogen independently of one another；Straight or branched and the C that can be replaced by following group 1-41-C20- alkyl：Hydroxyl, halogen, alkoxy, halogenated alkoxy, alkyloxy-alkoxy, alkylthio group, halogenated alkylthio, alkyl sulphinyl, alkyl sulphonyl, alkylsulfonyloxy, alkyl-carbonyl, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino, alkoxy carbonyl group, alkyl carbonyl oxy, cycloalkyl, phenyl, naphthyl, phenoxy group, naphthoxy, thiophenyl, naphthalene sulfenyl, benzenesulfonyl, naphthalene sulfonyl base, phenylsulfonyloxy, naphthalene sulfonyl epoxide, benzoyl, naphthoyl, with 5-6 annular atom and 1-2 N, the heteroatomic heteroaryls of O or S or heteroaryloxy, aryl described here and heteroaryl can be replaced by following group list or two：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, nitro, cyano group, phenoxy group, halogenated phenoxy, thiophenyl or halosphenylsulfanyl；Straight or branched and the C that can be replaced by halogen 1-43-C20- alkenyl；Straight or branched and the C that can be replaced by halogen 1-43-C20- alkynyl；The C that can be replaced by halogen, alkyl or haloalkyl 1-43-C7- cycloalkyl；The phenyl or naphthyl that can be replaced by following group 1-4：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, cycloalkyl alkoxy, halocycloalkylalkoxy, alkylthio group, halogenated alkylthio, alkylsulfonyloxy, haloalkylsulfonyloxy, halogenated alkoxy sulfonyloxy, alkylamino, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino, nitro, cyano group, trialkylsilkl, phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, with 5-6 annular atom and 1-2 N, the heteroatomic heteroaryls of O or S or heteroaryloxy, wherein described phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, heteroaryl and heteroaryloxy can be replaced as its part of substituent by following group list or two：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, nitro, cyano group, phenoxy group, thiophenyl, halosphenylsulfanyl, cycloalkyl alkoxy or halocycloalkylalkoxy；What can be replaced by following group 1-4 has 5-6 annular atom and 1-2 N, O or the heteroatomic heteroaryls of S：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, cycloalkyl alkoxy, halocycloalkylalkoxy, alkylthio group, halogenated alkylthio, alkylamino, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino, nitro, cyano group, trialkylsilkl, phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, with 5-6 annular atom and 1-2 N, the heteroatomic heteroaryls of O or S or heteroaryloxy, wherein described phenyl, phenoxy group, thiophenyl, benzoyl, benzyloxy, phenylamino, naphthyl, heteroaryl and heteroaryloxy can be replaced as its part of substituent by following group list or two：Halogen, alkyl, haloalkyl, alkoxy, halogenated alkoxy, alkylthio group, nitro, cyano group, phenoxy group, thiophenyl, halosphenylsulfanyl, cycloalkyl alkoxy, halocycloalkylalkoxy；R3It is hydrogen, fluorine or methyl；M is 0,1,2,3,4 or 5；N is 0 or 1；It is oxygen or NR with X4, wherein R4It is hydrogen, can be by the single or multiple substituted C of following group1-C4- alkyl：Halogen, C1-C4- alkoxy or two-C1-C4- alkyl amino, or can be by the single or multiple substituted benzyl of following group：Halogen, C1-C4- alkyl, halo-C1-C4- alkyl, C1-C4- alkoxy, nitro or cyano group.
4. according to formula (I) compound of claim 1 or 2, wherein R1And R2It is hydrogen independently of one another, or substituted or unsubstituted alkyl, cycloalkyl, alkenyl or alkynyl, R3Hydrogen, fluorine or methyl, m be 0,1,2,3,4 or 5n be 0 or 1, X be oxygen or NR4, and R4It is hydrogen, or substituted or unsubstituted C1-C6- alkyl or benzyl.
5. according to formula (I) compound of claim 1 or 2, wherein R1It is hydrogen or substituted or unsubstituted alkyl, alkenyl, alkynyl or cycloalkyl, R2It is hydrogen or substituted or unsubstituted aryl or heteroaryl, R3Hydrogen, fluorine or methyl, m is 0,1,2,3,4 or 5, and n be 0 or 1, X be oxygen or NR4, and R4It is hydrogen or substituted or unsubstituted C1-C6- alkyl or benzyl.
6. according to formula (I) compound of claim 1 or 2, wherein R1And R2It is hydrogen or substituted or unsubstituted aryl, R independently of one another3Hydrogen, fluorine or methyl, m is 0,1,2,3,4 or 5, and n be 0 or 1, X be oxygen or NR4, and R4It is hydrogen or substituted or unsubstituted C1-C6- alkyl or benzyl.
7. formula (I) compound according to claim any one of 1-5, wherein R3It is hydrogen and R1, R2, R4, m, n and X are as defined above.
8. formula (I) compound according to claim any one of 1-5, wherein m is 0,1,2,3 or 4 and R1, R2, R3, R4, n and X are as defined above.
9. formula (I) compound according to claim any one of 1-5, wherein m is 1 or 4 and R1, R2, R3, R4, n and X are as defined above.
10. formula (I) compound according to claim any one of 1-5, wherein n is 0 and R1, R2, R3, R4, m and X are as defined above.
11. formula (I) compound according to claim any one of 1-5, wherein n is that 0, m is 1 or 4 and R1, R2, R3, R4It is as defined above with X.
12. formula (I) compound according to claim any one of 1-5, wherein R3Hydrogen, n be 0, m be 1 or 4, X be NH or oxygen and R1And R2It is as defined above.
13. the preparation method of formula (I) compound according to claim 1, this method includes
A) it is 0 and R to prepare wherein n1, R2, R3, the logical formula (I) compound of X and m as defined in formula (I) above, it is reacted by logical formula (II) compound with logical formula (III) compound, the R led in formula (II)3With m as defined in formula (I), Y2It is Cl, Br or OSO2- alkyl.R in logical formula (III)1, R2With X as defined in formula (I)；
Figure A9880579500051
B) it is that 0 and X is NR to prepare wherein n4And R1, R2, R3With logical formula (I) compounds of the m as defined in formula (I), it is to be reacted by logical formula (IV) compound with logical formula (V) compound, leads to R in formula (IV)3, R4With m as defined in formula (I), the R led in formula (V)1And R2As defined in formula (I)；
C) it is 1 and R to prepare wherein n1, R2, R3, R4, the logical formula (I) compound of X and m as defined in formula (I), it is to be reacted by logical formula (VI) compound with logical formula (VII) compound, the R led in formula (VI)3With m as defined in formula (I), the Y led in formula (VII)1It is Cl, Br or OSO2- alkyl and R1, R2With X as defined in formula (I),
14. a kind of agricultural chemicals, agricultural chemicals formula (I) compound comprising at least one claim 1 in addition to inert additive and carrier is used as active material.
15. the preparation method of agricultural chemicals according to claim 14, this method includes mixing formula (I) compound of claim 1 and inert additive and carrier.
16. a kind of method of pest control, this method includes applying formula (I) compound described in claim 1 or the composition described in claim 14 to insect or its habitat.
17. formula (I) compound of the free or agricultural salt form described in claim 1 or if appropriate, the purposes of its isomers or dynamic isomer on the composition described in preparation claim 14.
18. the method according to claim 16 for protecting plant propagation original seed, this method includes the place of processing breeding original seed or processing plantation breeding original seed.
19. purposes of the composition described in formula (I) compound or claim 14 on pest control described in claim 1.
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