CN108570008A - Pyrazole analog derivative, preparation method and application - Google Patents

Pyrazole analog derivative, preparation method and application Download PDF

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Publication number
CN108570008A
CN108570008A CN201710306758.1A CN201710306758A CN108570008A CN 108570008 A CN108570008 A CN 108570008A CN 201710306758 A CN201710306758 A CN 201710306758A CN 108570008 A CN108570008 A CN 108570008A
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halogenated
alkyl
alkoxy
hydrogen
nitro
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CN108570008B (en
Inventor
许天明
袁静
钟良坤
郁季平
彭伟立
胡冬松
魏优昌
孔小林
郑志文
邢家华
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Zhejiang Chemical Industry Research Institute Co Ltd
Sinochem Corp
Sinochem Lantian Co Ltd
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Zhejiang Chemical Industry Research Institute Co Ltd
Sinochem Lantian Co Ltd
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    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

The invention discloses pyrazole derivatives shown in a kind of following general formula stru 1,The definition of each substituent group refers to specification.Pyrazole derivatives disclosed by the invention are suitable for pest control.

Description

Pyrazole analog derivative, preparation method and application
Technical field
The invention belongs to agricultural insecticidal, mite killing fields, and in particular to pyrazole analog derivative.
Background technology
Due to the long-time service of existing pesticide so that pest and disease damage produces resistance, so that Pesticide use amount significantly increases Add, serious destruction is caused to environment.Therefore it is required that constantly find the efficient novel pesticide with the new mechanism of action, such as to killing Worm, sterilization or mite killing have in higher active novel pesticide, such as existing acaricide pesticide species, and most of pesticide can only be prevented Control mite ovum, deutonymph, at the stage in mite three phases, if it is possible to which researching and developing all has mite three phases prevention effect The acaricide of the heart of fruit will be of great significance.
PCT Patent Application WO01/68589 discloses heterocycle acrylonitrile ether compound, and specification page 71 discloses down Compound 8-1,8-2,8-3 and 8-4 are stated,
Pyrazole derivatives described herein are not disclosed in the prior art.
Invention content
The present invention provides Set of Pyrazole Derivatives, has following general formula stru-1：
Wherein：
R1, R2, R3, R4, R5 are independently selected from hydrogen, halogen, nitro, itrile group, C1-C20Alkyl, C1-C20Halogenated alkyl, C2- C20Alkenyl, C2-C20Halogenated alkenyl, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1- C20Alkylthio group, C1-C20Halogenated alkylthio, C1-C20Alkane sulfoxide group, C1-C20Alkane sulfuryl, C1-C20Alkyl sulfonic acid ester group, C1-C20Alkane Yl carboxylic acid ester, C1-C20Alkyl acyl, C1-C20Halogenated alkyl acyl group；
R6 is selected from hydrogen, halogen, nitro, itrile group, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20It is halogenated Naphthenic base, C2-C20Alkenyl, C2-C20Halogenated alkenyl, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20It is halogenated Alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogen Substituted alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Haloalkoxy Base, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20Pyridyl group, pyrazolyl, the thiophene of at least one of alkane sulfuryl substitution Phenolic group, furyl or thiazolyl；
R7 is selected from hydrogen, halogen, nitro, itrile group, C1-C20Alkyl, C1-C20Halogenated alkyl, C1-C20Alcoxyl methylene；
R8 is selected from hydrogen, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkane Oxymethylene, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogen Substituted naphthene base, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20Alkane sulfuryl At least one of substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20 Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Alkyl halide sulphur Base and C1-C20Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of at least one of alkane sulfuryl substitution；
R9 is selected from hydrogen, halogen, nitro, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkanes Base, C2-C20Alkenyl, C2-C20Halogenated alkenyl, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Haloalkoxy Base, C1-C20Alkylthio group, C1-C20Halogenated alkylthio, C1-C20Alkane sulfuryl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkane Sulfenyl, C1-C20Halogenated alkylthio and C1-C20At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyanogen Base, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20It is halogenated Alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20Pyridyl group, the pyrazoles of at least one of alkane sulfuryl substitution Base, thiophene phenyl, furyl or thiazolyl；
L is selected from oxygen, sulphur, methylene, nitrogen；
Q is selected from oxygen, sulphur；
R10 is selected from hydrogen, halogen, nitro, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkanes Base, C2-C20Alkenyl, C2-C20Halogenated alkenyl, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Haloalkoxy Base, C1-C20Alkylthio group, C1-C20Halogenated alkylthio, C1-C20Alkyl carboxylic acid ester, by selected from hydrogen, halogen, nitro, cyano, C1-C20 Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group and C1-C20At least one of halogenated alkylthio substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Haloalkoxy Base, C1-C20Alkylthio group and C1-C20Pyridyl group, pyrazolyl, thiophene phenyl, the furyl of at least one of halogenated alkylthio substitution Or thiazolyl.
In pyrazole derivatives shown in general formula stru-1 provided by the invention, substituent R 1, R2, R3, R4, R5 are independently selected From hydrogen, halogen, nitro, itrile group, C1-C20Alkyl, C1-C20Halogenated alkyl, C2-C20Alkenyl, C2-C20Halogenated alkenyl, C2-C20Alkynes Base, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio, C1- C20Alkane sulfoxide group, C1-C20Alkane sulfuryl, C1-C20Alkyl sulfonic acid ester group, C1-C20Alkyl carboxylic acid ester, C1-C20Alkyl acyl, C1-C20 Halogenated alkyl acyl group.
Preferably, the substituent R 1, R2, R3, R4, R5 are independently selected from hydrogen, halogen, nitro, itrile group, C1-C10Alkane Base, C1-C10Halogenated alkyl, C2-C10Alkenyl, C2-C10Halogenated alkenyl, C2-C10Alkynyl, C2-C10Halo alkynyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio, C1-C10Alkane sulfoxide group, C1-C10Alkane sulfuryl, C1-C10Alkane Base sulfonate group, C1-C10Alkyl carboxylic acid ester, C1-C10Alkyl acyl, C1-C10Halogenated alkyl acyl group.
It may further be preferable that the substituent R 1, R2, R3, R4, R5 independently selected from hydrogen, halogen, nitro, itrile group, C1-C6Alkyl, C1-C6Halogenated alkyl, C2-C6Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alcoxyl Base, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, C1-C6Alkane sulfoxide group, C1-C6Alkane sulfuryl, C1-C6Alkane Base sulfonate group, C1-C6Alkyl carboxylic acid ester, C1-C6Alkyl acyl, C1-C6Halogenated alkyl acyl group.
Still further preferably, the substituent R 1, R2, R3, R4, R5 independently selected from hydrogen, fluorine, chlorine, bromine, nitro, Itrile group, methyl, ethyl, isopropyl, tertiary butyl, trifluoromethyl, methoxyl group, ethyoxyl, trifluoromethoxy, difluoro-methoxy, two Fluorine ethyoxyl, methyl mercapto, trifluoromethylthio, trifluoro ethylmercapto group, methylsulfonyl, methylsulphur base ester.
In pyrazole derivatives shown in general formula stru-1 provided by the invention, substituent R 6 is selected from hydrogen, halogen, nitro, nitrile Base, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C2-C20Alkenyl, C2-C20Haloalkene Base, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20It is halogenated Alkylthio group, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20It is halogenated Naphthenic base, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20In alkane sulfuryl At least one substituted phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Ring Alkyl, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio And C1-C20Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of at least one of alkane sulfuryl substitution.
Preferably, the substituent R 6 is selected from hydrogen, halogen, nitro, itrile group, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C2-C10Alkenyl, C2-C10Halogenated alkenyl, C2-C10Alkynyl, C2-C10Halo alkynyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio, by selected from hydrogen, halogen, nitro, cyanogen Base, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10It is halogenated Alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio and C1-C10At least one of alkane sulfuryl substitution phenyl, by selected from Hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkane Oxygroup, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio and C1-C10At least one of alkane sulfuryl replaces Pyridyl group, pyrazolyl, thiophene phenyl, furyl or thiazolyl.Shown compound can be that E formulas, Z formulas or E formulas and Z formulas mix Object；
It may further be preferable that the substituent R 6 is selected from hydrogen, halogen, nitro, itrile group, C1-C6Alkyl, C1-C6Alkyl halide Base, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C2-C6Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio and C1-C6At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitre Base, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6It is halogenated Alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio and C1-C6At least one of alkane sulfuryl substitution pyridyl group, pyrazolyl, Thiophene phenyl, furyl or thiazolyl.
Still further preferably, the substituent R 6 is selected from hydrogen, fluorine, chlorine, bromine, nitro, itrile group, methyl, ethyl, isopropyl Base, cyclopropyl, methoxyl group, ethyoxyl, trifluoromethyl, difluoromethyl, rubigan, p-fluorophenyl.
In pyrazole derivatives shown in general formula stru-1 provided by the invention, substituent R 7 is selected from hydrogen, halogen, nitro, nitrile Base, C1-C20Alkyl, C1-C20Halogenated alkyl, C1-C20Alcoxyl methylene.
Preferably, the substituent R 7 is selected from hydrogen, halogen, nitro, itrile group, C1-C10Alkyl, C1-C10Halogenated alkyl, C1-C10Alcoxyl methylene.
It may further be preferable that the substituent R 7 is selected from hydrogen, halogen, nitro, itrile group, C1-C6Alkyl, C1-C6Alkyl halide Base, C1-C6Alcoxyl methylene.
Still further preferably, the substituent R 7 is selected from hydrogen, halogen, nitro, itrile group, C1-C5Alkyl, C1-C5It is halogenated Alkyl, C1-C5Alcoxyl methylene.
In pyrazole derivatives shown in general formula stru-1 provided by the invention, substituent R 8 is selected from hydrogen, C1-C20Alkyl, C1- C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alcoxyl methylene, by selected from hydrogen, halogen, nitro, cyanogen Base, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20It is halogenated Alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20At least one of alkane sulfuryl substitution phenyl, by selected from Hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkane Oxygroup, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20At least one of alkane sulfuryl replaces Pyridyl group, pyrazolyl, thiophene phenyl, furyl or thiazolyl.
Preferably, the substituent R 8 is selected from hydrogen, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10 Halogenated cycloalkyl, C1-C10Alcoxyl methylene, by selected from hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10It is halogenated Alkylthio group and C1-C10At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkane Sulfenyl, C1-C10Halogenated alkylthio and C1-C10Pyridyl group, pyrazolyl, thiophene phenyl, the furans of at least one of alkane sulfuryl substitution Base or thiazolyl.
It may further be preferable that the substituent R 8 is selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alcoxyl methylene, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Alkyl halide sulphur Base and C1-C6At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogen Substituted alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6 Halogenated alkylthio and C1-C6Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of at least one of alkane sulfuryl substitution.
Still further preferably, the substituent R 8 is selected from hydrogen, methyl, ethyl, a methyl fluoride, difluoromethyl, trifluoro Methyl, methoxymethylene, ethoxymeyhylene.
In pyrazole derivatives shown in general formula stru-1 provided by the invention, substituent R 9 is selected from hydrogen, halogen, nitro, C1- C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C2-C20Alkenyl, C2-C20Halogenated alkenyl, C2- C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio, C1-C20Alkane sulfuryl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20 Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20Alkane sulfone At least one of base substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3- C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Alkyl halide Sulfenyl and C1-C20Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of at least one of alkane sulfuryl substitution.
Preferably, the substituent R 9 is selected from hydrogen, halogen, nitro, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Ring Alkyl, C3-C10Halogenated cycloalkyl, C2-C10Alkenyl, C2-C10Halogenated alkenyl, C2-C10Alkynyl, C2-C10Halo alkynyl, C1-C10Alkane Oxygroup, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio, C1-C10Alkane sulfuryl, by selected from hydrogen, halogen, nitre Base, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10 Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio and C1-C10Phenyl, the quilt of at least one of alkane sulfuryl substitution Selected from hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1- C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio and C1-C10At least one of alkane sulfuryl Substituted pyridyl group, pyrazolyl, thiophene phenyl, furyl or thiazolyl.
It may further be preferable that the substituent R 9 is selected from hydrogen, halogen, nitro, C1-C6Alkyl, C1-C6Halogenated alkyl, C3- C6Naphthenic base, C3-C6Halogenated cycloalkyl, C2-C6Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkane Oxygroup, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, C1-C6Alkane sulfuryl, by selected from hydrogen, halogen, nitro, Cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Alkyl halide Oxygroup, C1-C6Alkylthio group, C1-C6Halogenated alkylthio and C1-C6At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen Element, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1- C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio and C1-C6The pyridyl group of at least one of alkane sulfuryl substitution, Pyrazolyl, thiophene phenyl, furyl or thiazolyl.
Still further preferably, the substituent R 9 is selected from hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, propyl, isopropyl Base, difluoromethyl, cyclopropyl, methylthiomethylene, phenyl, rubigan, p-fluorophenyl, benzyl.
In pyrazole derivatives shown in general formula stru-1 provided by the invention, substituent group L is selected from oxygen, sulphur, methylene, nitrogen.
Preferably, the substituent group L is selected from oxygen, sulphur, methylene.
In pyrazole derivatives shown in general formula stru-1 provided by the invention, substituent group Q is selected from oxygen, sulphur.
In pyrazole derivatives shown in general formula stru-1 provided by the invention, substituent R 10 be selected from hydrogen, halogen, nitro, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C2-C20Alkenyl, C2-C20Halogenated alkenyl, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Alkyl halide sulphur Base, C1-C20Alkyl carboxylic acid ester, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Cycloalkanes Base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group and C1-C20In halogenated alkylthio At least one substituted phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Ring Alkyl, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group and C1-C20Halogenated alkylthio At least one of substitution pyridyl group, pyrazolyl, thiophene phenyl, furyl or thiazolyl.
Preferably, the substituent R 10 is selected from hydrogen, halogen, nitro, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10 Naphthenic base, C3-C10Halogenated cycloalkyl, C2-C10Alkenyl, C2-C10Halogenated alkenyl, C2-C10Alkynyl, C2-C10Halo alkynyl, C1-C10 Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio, C1-C10Alkyl carboxylic acid ester, by selected from hydrogen, Halogen, nitro, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alcoxyl Base, C1-C10Halogenated alkoxy, C1-C10Alkylthio group and C1-C10At least one of halogenated alkylthio substitution phenyl, by selected from Hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkane Oxygroup, C1-C10Halogenated alkoxy, C1-C10Alkylthio group and C1-C10Pyridyl group, the pyrrole of at least one of halogenated alkylthio substitution Oxazolyl, thiophene phenyl, furyl or thiazolyl.
It may further be preferable that the substituent R 10 is selected from hydrogen, halogen, nitro, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C2-C6Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6 Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, C1-C6Alkyl carboxylic acid ester, by selected from hydrogen, halogen Element, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1- C6Halogenated alkoxy, C1-C6Alkylthio group and C1-C6At least one of halogenated alkylthio substitution phenyl, by selected from hydrogen, halogen, Nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogen For alkoxy, C1-C6Alkylthio group and C1-C6Pyridyl group, pyrazolyl, thiophene phenyl, the furan of at least one of halogenated alkylthio substitution It mutters base or thiazolyl.
Still further preferably, the substituent R 10 is selected from hydrogen, fluorine, chlorine, nitro, C1-C6Alkyl, C3-C6Naphthenic base, C3-C6Halogenated alkyl, C2-C6Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogen For alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, C1-C6Alkyl carboxylic acid methyl esters, C1-C6Alkyl carboxylic acid ethyl ester, by selected from In hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxyl group, ethyoxyl, trifluoro ethoxy and methyl mercapto extremely Lack the phenyl of a substitution, by selected from hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxyl group, ethoxy At least one substituted pyridyl group, pyrazolyl, thiophene phenyl, furyl or thiazolyl in base, trifluoro ethoxy and methyl mercapto.
Pyrazole derivatives shown in general formula stru-1 provided by the invention are described logical as a kind of than more preferably mode In formula stru-1：
R1, R2, R3, R4, R5 are independently selected from hydrogen, fluorine, chlorine, bromine, nitro, itrile group, methyl, ethyl, isopropyl, tertiary fourth Base, trifluoromethyl, methoxyl group, ethyoxyl, trifluoromethoxy, difluoro-methoxy, difluoroethoxy, methyl mercapto, trifluoromethylthio, Trifluoro ethylmercapto group, methylsulfonyl, methylsulphur base ester；
R6 is selected from hydrogen, fluorine, chlorine, bromine, nitro, itrile group, methyl, ethyl, isopropyl, cyclopropyl, trifluoromethyl, difluoro first Base, methoxyl group, ethyoxyl, rubigan, p-fluorophenyl；
R7 is selected from hydrogen, halogen, nitro, itrile group, C1-C5Alkyl, C1-C5Halogenated alkyl, C1-C5Alcoxyl methylene；
R8 is selected from methyl, ethyl；
It is sub- that R9 is selected from hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, propyl, isopropyl, difluoromethyl, cyclopropyl, methyl mercapto Methyl, phenyl, rubigan, p-fluorophenyl, benzyl；
L is selected from oxygen, sulphur, methylene；
Q is selected from oxygen, sulphur；
R10 is selected from hydrogen, fluorine, chlorine, nitro, C1-C6Alkyl, C3-C6Naphthenic base, C3-C6Halogenated alkyl, C2-C6Alkenyl, C2-C6 Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogen For alkylthio group, C1-C6Alkyl carboxylic acid methyl esters, C1-C6Alkyl carboxylic acid ethyl ester, by selected from hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, At least one substituted phenyl in ethyl, trifluoromethyl, methoxyl group, ethyoxyl, trifluoro ethoxy and methyl mercapto, by selected from hydrogen, In fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxyl group, ethyoxyl, trifluoro ethoxy and methyl mercapto at least Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of one substitution.
Pyrazole derivatives shown in general formula stru-1 provided by the invention, it is described as another kind than more preferably mode In general formula stru-1：
R1, R2, R4, R5 are selected from hydrogen；
R3 is selected from tertiary butyl；
R6 is selected from hydrogen, fluorine, chlorine, bromine, nitro, itrile group, methyl, ethyl, isopropyl, cyclopropyl, trifluoromethyl, difluoro first Base, methoxyl group, ethyoxyl, rubigan, p-fluorophenyl；
R7 is selected from hydrogen, halogen, nitro, itrile group, C1-C5Alkyl, C1-C5Halogenated alkyl, C1-C5Alcoxyl methylene；
R8 is selected from methyl, ethyl；
It is sub- that R9 is selected from hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, propyl, isopropyl, difluoromethyl, cyclopropyl, methyl mercapto Methyl, phenyl, rubigan, p-fluorophenyl, benzyl；
L is selected from oxygen, sulphur, methylene；
Q is selected from oxygen, sulphur；
R10 is selected from hydrogen, fluorine, chlorine, nitro, C1-C6Alkyl, C3-C6Naphthenic base, C3-C6Halogenated alkyl, C2-C6Alkenyl, C2-C6 Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogen For alkylthio group, C1-C6Alkyl carboxylic acid methyl esters, C1-C6Alkyl carboxylic acid ethyl ester, by selected from hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, At least one substituted phenyl in ethyl, methoxyl group, ethyoxyl, trifluoromethyl, trifluoro ethoxy and methyl mercapto, by selected from hydrogen, In fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxyl group, ethyoxyl, trifluoromethyl, trifluoro ethoxy and methyl mercapto at least Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of one substitution.
Pyrazole derivatives shown in general formula stru-1 provided by the invention, as highly preferred mode, the pyrazoles spreads out Biology is selected from least one of compound shown in following structural formula：
The pyrazole derivatives that the above number indicates, it is preferred that the compound is E formula pyrazole derivatives, i.e. E formulas isomery Body.
Pyrazole derivatives shown in general formula stru-1 provided by the invention, the pyrazole derivatives include being selected from E formula pyrazoles At least one of derivative and Z formula pyrazole derivatives.When the pyrazole derivatives include E formulas pyrazole derivatives and Z formula pyrazoles When derivative, can exist in any proportion between the E formulas pyrazole derivatives and Z formula pyrazole derivatives.
Pyrazole derivatives shown in general formula stru-1 provided by the invention, when substituent R 1, R2, R4, R5 are hydrogen and Q is oxygen When, as an example, when the pyrazole derivatives shown in the general formula stru-1 are E formula compounds, shown in the general formula stru-1 Pyrazole derivatives can be compound shown in table 1.
Table 1
Pyrazole derivatives shown in general formula stru-1 provided by the invention, when substituent R 1, R2, R4, R5 are hydrogen and Q is oxygen When, as an example, when the pyrazole derivatives shown in the general formula stru-1 are Z formula compounds, shown in the general formula stru-1 Pyrazole derivatives can be compound shown in table 2.
Table 2
The physical data of part of compounds provided by the invention such as the following table 3.
Table 3
The present invention also provides the preparation method of pyrazole derivatives shown in general formula stru-1, the method includes：
The X is selected from halogen.
Preparation method provided by the invention, the alkali：Preferably, at least one of organic base and inorganic base are selected from； It may further be preferable that selected from sodium carbonate, potassium carbonate, sodium bicarbonate, saleratus, sodium hydroxide, potassium hydroxide, sodium hydride, At least one of sodium alkoxide and potassium alcoholate.
Preparation method provided by the invention, the acid：Preferably, at least one of organic acid and inorganic acid are selected from； It may further be preferable that selected from least one of hydrochloric acid, sulfuric acid and acetic acid.
Preparation method provided by the invention, the solvent：Preferably, independently selected from protonic solvent and aprotic At least one of solvent；It may further be preferable that independently selected from acetone, methyl ethyl ketone, tetrahydrofuran, acetonitrile, N, N- At least one of dimethylformamide, toluene and chlorobenzene.
Preparation method provided by the invention, the X are selected from halogen, it is preferred that the X is selected from chlorine, bromine or iodine.
Preparation method provided by the invention, the catalyst in potassium iodide, sodium iodide and phase transfer catalyst extremely Few one kind.
The present invention also provides a kind of agricultural insecticidal, acaricide, the Insecticidal and acaricidal agent contains 0.1~99% mass percentage Pyrazole derivatives shown in the general formula stru-1 of content.In the Insecticidal and acaricidal agent, except pyrazole derivatives shown in general formula stru-1 Outside, the common carrier of the industry and auxiliary agent be can further include.
Pyrazole derivatives shown in general formula stru-1 provided by the invention are suitable for pest control, particularly suitable for Prevent crop at least one of mite, deutonymph, mite ovum, aphid and plant hopper.The pyrazole derivatives are well suited for for preventing Control the animal pest in climbing plant, fruit, gardening, agricultural, animal health, forest, stored product and material and health field.
Preferably, the pyrazole derivatives are for preventing selected from Isopoda, times sufficient mesh, lip foot mesh, comprehensive mesh, tassel tail Mesh, Collembola, Orthoptera, Blattaria, Dermaptera, Isoptera, Anoplura, Thysanoptera, Heteroptera, Homoptera, Lepidoptera, elytrum At least one of mesh, Hymenoptera, Diptera, Siphonaptera, Arachnoidea and plant nematode.
The Isopoda (Isopoda), such as comb beach louse (Oniscus asellus), mouse (Armadillidium Vulgare), ball pillworm (Porcellio scaber).
Described times of sufficient mesh (Diplopoda), for example, Blaniulus guttulatus.
The lip foot mesh (Chilopoda), for example, Geophilus carpophagus, Scutigera spp..
The comprehensive mesh (Symphyla), for example, kahikatea worm (Scutigerella immaculata).
The Thysanoptera (Thysanura), for example, silverfish (Lepisma saccharina).
The Collembola (Collembola), for example, arms Onychiurus arcticus (Onychiurus armatus).
The Orthoptera (Orthoptera), for example, family Xi (Acheta domesticus), Gryllotalpa spp (Gryllotalpa spp.), African migratory locust (Locusta migratoria), black locust (Melanoplus spp.), desert locust (Schistocer cagregaria)。
The Blattaria (Blattaria), for example, Oriental cockroach (Blatta orientalis), America roach (Periplanet aamericana), Florida cockroach (Leucophae amaderae), Germany cockroach (Blattella germanica)。
The Dermaptera (Dermaptera), for example, European earwig (Forficula auricularia).
The Isoptera (Isoptera), for example, Reticulitermes (Reticulitermes spp.).
The Anoplura (Phthiraptera), for example, pediculus humanus corporis (Pediculus humanuscorporis), Haematopinus (Haematopinus spp.), Linognathus (Linognathus spp.), Trichodectes (Trichodectes spp.), Damalinia (Damalinia spp.)。
The Thysanoptera (Thysanoptera), for example, greenhouse hedge thrips (Hercinothrips femoralis), Onion thrips (Thrips tabaci), palm thrips (Thrips palmi), Frankliniella occidentalis (Frankliniella occidentalis)。
The Heteroptera (Heteroptera), for example, Eurygasterspp category (Eurygaster spp.), between two parties red cotton bug (Dysdercus intermedius), square butt stinkbug (Piesma quadrata), bed bug (Cimexlectularius), Long red triatome bug (Rhodnius prolixus), Triatoma (Triatoma spp.).
The Homoptera (Homoptera), for example, trialeurodes vaporariorum (Aleurodes brassicae), tobacco powder (Bemisia Tabaci), greenhouse whitefly (Trialeurodes vaporariorum), cotten aphid (Aphis gossypii), brevicoryne brassicae (Brevicoryne brassicae), the hidden tumor aphid of tea Fischer (Cryptomyzus ribis), black bean aphid (Aphis fabae), apple Fruit yellow aphids (Aphis pomi), eriosoma lanigerum (Eriosoma lanigerum), mealy plum aphid (Hyalopterus Arundinis), grape phylloxera (Phylloxera vastatrix), Pemphigus (Pemphigus spp.), grain aphid (Macrosiphum avenae), tumor aphid genus (Myzus spp.), phorodon aphid (Phorodon humuli), rhopalosiphum padi (Rhopalosiphum padi), Empoasca flavescens (Empoasca spp.), Euscelis bilobatus, green rice leafhopper (Nephotettix cincticeps), scale insect (Lecanium corni), olive pearl lecanium (Saissetia oleae), ash Plant hopper (Laodelphax striatellus), brown paddy plant hopper (Nilaparvatalugens), California red scale (Aonidiella Aurantii), ivy Aspidiotus (Aspidiotus hederae), mealybug belong to kind of (a Pseudococcus spp.), Psylla spp Kind (Psylla spp.).
The Lepidoptera (Lepidoptera), for example, Pectinophora gossypiella (Pectinophora gossypiella), loose ruler Earwig (Bupalus piniarius), winter geometrid moth (Cheimatobia brumata), the thin moth (Lithocolletis of apple Blancardella), apple ermine moth (Hyponomeuta padella), diamond-back moth (Plutella xylostella), yellowish-brown day Curtain caterpillar (Malacosoma neustria), pornography and drug moth (Euproctis chrysorrhoea), Euproctis (Lymantria Spp.), cotton lyonetid (Bucculatrix thurberiella), tangerine lyonetid (Phyllocrnistis citrella), cutworm Belong to (Agrotis spp.), cutworm category (Euxoa spp.), dirty cut Noctua (Feltia spp.), earias insulana (Earias insulana), Heliothis (Heliothis spp.), lopper worm (Mamestra brassicae), ommatidium Noctuid (Panolis flammea), Spodoptera (Spodoptera spp.), cabbage looper (Trichoplusia ni), Codling moth (Carpocap sapomonella), Pieris spp (Pieris spp.), straw borer spp (Chilo spp.), Corn borer (Pyrausta nubilalis), Anagasta kuehniella (Ephestia kuehniella), greater wax moth (Galleria Mellonella), Tineolabisselliella (Tineola bisselliella), bag rain moth (Tinea pellionella), brown knit moth (Hofmannophilap seudospretella), flax Huang roll up moth (Cacoecia podana), spruce bunworm (Choristoneura fumiferana), grape codling moth (Clysia ambiguella) (Clysia ambiguella), Homonamagnanima (Homona Magnanima), the green volume moth of oak (Tortrix viridana), rice leaf roller belong to kind of (a Cnaphalocerus spp.), rice Scotellaris (Oulema oryzae).
The coleoptera (Coleoptera), for example, furniture death watch beetle (Anobium punctatum), lesser grain borer (Rhizopertha dominica), a bean weevil (Bruchidius obtectus), acanthoscelides obtectus (Acanthoscelides are disliked Obtectus), North America house longhorn beetle (Hylotrupes bajulus), willow firefly chrysomelid (Agelastica alni), potato first Worm (Leptinotarsa decemlineata), horseradish daikon leaf beetle (Phaedon cochleariae), chrysomelid category (Diabrotica spp.), rape golden head flea beetle (Psylliodes chrysocephala), mexican bean ladybird (Epilachna varivestis), Atomaria spp., saw-toothed grain beetle (Oryzaephilus surinamensis), flower genus Kind (Anthonomus spp.), grain weevil category (Sitophilus spp.), black grape ear image (Otiorrhynchus Sulcatus), banana bulb weevil (Cosmopolites sordidus), Chinese cabbage tortoise are as (Ceuthorrhynchus Assimilis), alfalfa leaf is as (Hypera postica), khapra beetle category (Dermestes spp.), spot khapra beetle category (Trogoderma spp.), Anthrenus (Anthrenus spp.), fur moth category (Attagenus spp.), powder moth category (Lyctus spp.), pollen beetle (Meligethes aeneus), Ptinus (Ptinus spp.), golden spider beetle (Niptus bololeucus), globose spider beetle (Gibbium psylloides), Tribolium (Tribolium spp.), bloom Worm (Tenebrio molitor), click beetle category (Agriotes spp.), wide chest Agriotes spp (Conoderus spp.), west The melolonthid in May (Melolontha melolontha), the potato melolonthid (Amphimallon solstitialis), Brown New Zealand's rib wing melolonthid (Costelytra zealandica), rice root weevil (Lissorhoptrus oryzophilus)。
The Hymenoptera (Hymenoptera), for example, Diprion (Diprion spp.), real tenthredinidae (Hoplocampa spp.), hair ant category (Lasius spp.), MonomoriumMayr (Monomorium pharaonis), Vespa (Vespa spp.)。
The Diptera (Diptera), for example, Aedes (Aedes spp.), Anopheles (Anopheles spp.), library Uranotaenia (Culex spp.), Drosophila melanogaster (Drosophila melanogaster), Musca (Musca spp.), Fannia (Fannia spp.), calliphora erythrocephala (Calliphora vicina), Lucilia (Lucilia spp.), Carysomyia (Chrysomyia spp.), Cuterebra (Cuterebra spp.), Gasterophilus (Gastrophilus spp.), Hippobosca (Hyppobosca spp.), Genus Stomoxys (Stomoxys spp.), Oestrus (Oestrus spp.), Hypoderma (Hypoderma Spp.), Gadfly (Tabanus spp.), garden march fly (Bibio hortulanus), Oscinella frit (Oscinella Frit), Phorbia (Phorbia spp.), lamb's-quarters spring fly (Pegomyia hyoscyami), Mediterranean Ceratitis spp (Ceratitis capitata), the big trypetid of olive (Dacus oleae), European daddy-longlegs (Tipula paludosa), Hylemyia (Hylemyia spp.), Liriomyza (Liriomyza spp.).
The Siphonaptera (Siphonaptera), for example, Xanthopsyllacheopis (Xenopsylla cheopis), Ceratophyllus (Ceratophyllus spp.)。
The Arachnoidea (Arachnida), for example, Middle East gold scorpion (Scorpio maurus), latrodectus mactans (Latrodectus mactans), Acarus siro (Acarus siro), Argas kind (Argas spp.), Ornithodoros (Ornithodoros spp.), Dermanyssus gallinae (Dermanyssus gallinae), tea Fischer goitre mite (Erio phyesribis), Tangerine rue rust mite (Phyllocoptruta oleivora), Boophilus (Boophilus spp.), Rhinpicephalus (Rhipicephalus spp.), Amblyomma (Amblyomma spp.), Hyalomma (Hyalomma spp.), Isodesspp (Ixodes spp.), Psoroptes (Psoroptes spp.), Chorioptes (Chorioptes spp.), Sarcoptesspp (Sarcoptes Spp.), Tarsonemus (Tarsonemus spp.), Bryobia praetiosa (Bryobia praetiosa), Panonychus citri category It is (Panonychus spp.), Tetranychus (Tetranychus spp.), half Tarsonemus (Hemitarsonemus spp.), short It must mite category (Brevipalpus spp.).
The plant nematode includes, for example, Pratylenchus (Pratylenchus spp.), Radopholus similis Throne (Radopholus similis), fuller's teasel Ditylenchus dipsaci (Ditylenchus dipsaci), Tylenchulus Semipenetrans (Tylenchulus Semipenetrans), Heterodera (Heterodera spp.), ball Heterodera (Globodera spp.), root knot Turbatrix (Meloidogyne spp.), Aphelenchoides (Aphelenchoides spp.), minute hand Turbatrix (Longidorus spp.), Xiphinema (Xiphinema spp.), burr Turbatrix (Trichodorus spp.), umbrella are slided Sword Turbatrix (Bursaphelenchus spp.).
Description of the drawings
Fig. 1 is the single crystal diffraction figure of compound 251.
Specific implementation mode
With reference to specific embodiment, invention is further explained, but does not limit the invention to these tools Body embodiment.One skilled in the art would recognize that present invention encompasses may include in Claims scope All alternatives, improvement project and equivalent scheme.
One, prepared by compound
It is prepared by embodiment 1, intermediate
(1) intermediate 1- ethyls -3- methyl -5- pyrazole carboxylic acid ethyl esters synthesize
154.1g (1mol) intermediate A is added in the flask of 1000ml, 500ml acetonitriles and 138g potassium carbonate is added, Then 1mol dithyl sulfates, system agitating and heating back flow reaction is added, plate layer chromatography tracks about 3hr reactions and completes, system mistake Filter, mother liquor are evaporated with Rotary Evaporators, and residue carries out the intermediate B for being evaporated under reduced pressure to 140g, yield 77.0%.
(2) the chloro- 5- pyrazole carboxylic acids ethyl ester synthesis of intermediate 1- ethyls -3- methyl -4-
18.2g (0.1mol) intermediate B is added in the flask of 100ml, 50ml dichloroethanes and 138g carbonic acid is added Then 0.11mol sulfonic acid chlorides, system agitating and heating back flow reaction is added in potassium, plate layer chromatography tracks about 2.5hr reactions and completes, female Liquid is evaporated, and residue does not handle to be directly used in react in next step.
(3) intermediate 1- ethyls -3- methyl -4- methyl -5- pyrazole carboxylic acid ethyl esters synthesize
Intermediate D is made with reference to JP2001342178A providing methods.
(4) intermediate 1- methyl -3- methyl -4- methyl -5- pyrazole carboxylic acid ethyl esters synthesize
Intermediate D-1 is made with reference to JP2001342178A providing methods.
(5) the chloro- 5- pyrazole carboxylic acids ethyl ester synthesis of intermediate 1- methyl -3- methyl -4-
Intermediate C-1 preparation methods are the same as intermediate C.
(6) prepared by intermediate F
Routine operation：Substitution aldehyde is stirred evenly in the reactor with catalytic amount zinc chloride, is slowly added dropwise takes under cooling Continue to stir 1-2hr at low temperature for acyl chlorides, after being added dropwise, then heat up, then the reaction was continued 5hr passes through vacuum distillation Mode purifies.
It is prepared by intermediate acetic acid chloro methyl esters：
50g (0.6mol) chloroacetic chloride is added drop-wise to 85g paraformaldehydes and 1.75g zinc chloride mixtures in the case where being cooled to 0 DEG C In, about 2hr is added dropwise, and then reaction system is warmed to room temperature, and reacts 1hr, is then heated to 90 DEG C the reaction was continued 10hr, cold But, filtering removal solid, is evaporated under reduced pressure to intermediate F-1 45g.
(7) prepared by intermediate H
Routine operation：Chloro-carbonic acid chloro ester is slowly dropped in substituted alcohols and triethylamine solution under cooling, is dripped Continue to stir 1-2hr at low temperature after finishing, then heat up, then room temperature the reaction was continued 1hr is filtered, steamed solvent, then pass through Vacuum distillation mode purifies to obtain intermediate H.
It is prepared by intermediate H-1：
71.5g (0.5mol) 1- chloroethylchloroformate esters are added drop-wise to 40g and 52.0g triethylamines in the case where being cooled to 0 DEG C In 250ml toluene solutions, about 2hr is added dropwise, and then reaction system is warmed to room temperature, and reacts 1hr, and filtering removal solid subtracts Pressure distill intermediate H-1 be 78.5g.
(8) prepared by intermediate TA-1
17.3g dissolves in the anhydrous THF of 70ml tert-butyl benzene acetonitrile, system is cooled to -5 DEG C of addition equimolar solid first Then sodium alkoxide instills equimolar intermediate B under stiring, 2hr is added dropwise, and continues to stir 1.5hr, is then raised to room temperature, after It is continuous to be stirred to react 2hr, THF is steamed after the completion of reaction, residue water dissolution, it is 4 or so that pH, which is neutralized with hydrochloric acid, with acetic acid second Ester extracts, and is dried with anhydrous sodium sulfate, steams ethyl acetate and obtain intermediate TA-1, is not required to purification and is directly used in reaction in next step.
(9) prepared by intermediate TA-2
17.3g dissolves in the anhydrous THF of 70ml tert-butyl benzene acetonitrile, system is cooled to -5 DEG C of addition equimolar solid uncles Butanol potassium, then instillation equimolar intermediate C, 2.5hr are added dropwise under stiring, continue to stir 2.0hr, are then raised to room Temperature continues to be stirred to react 2hr, THF is steamed after the completion of reaction, residue water dissolution, it is 4 or so that pH, which is neutralized with hydrochloric acid, is used Ethyl acetate extracts, and is dried with anhydrous sodium sulfate, steams ethyl acetate and obtain intermediate TA-2, is not required to purification and is directly used in next step Reaction.
(10) prepared by intermediate TA-3
17.3g dissolves in 70ml methyl tertiary butyl ether(MTBE)s tert-butyl benzene acetonitrile, system is cooled to -5 DEG C of addition equimolars Solid potassium tert-butoxide, then instillation equimolar intermediate D, 3.0hr are added dropwise under stiring, continue to stir 2.0hr, then rise To room temperature, continues to be stirred to react 2hr, steam methyl tertiary butyl ether(MTBE) after the completion of reaction, residue water dissolution is neutralized with hydrochloric acid PH is 4 or so, is extracted with ethyl acetate, is dried with anhydrous sodium sulfate, steams ethyl acetate and obtain intermediate TA-3, and it is straight to be not required to purification It connects for reacting in next step.
(11) prepared by intermediate TA-4
17.3g dissolves in the anhydrous THF of 70ml tert-butyl benzene acetonitrile, system is cooled to -5 DEG C of addition equimolar solid first Sodium alkoxide, then instillation equimolar intermediate M, 2hr are added dropwise under stiring, continue to stir 1.5hr, are then raised to room temperature, after It is continuous to be stirred to react 2hr, THF is steamed after the completion of reaction, residue water dissolution, it is 4 or so that pH, which is neutralized with hydrochloric acid, with acetic acid second Ester extracts, and is dried with anhydrous sodium sulfate, steams ethyl acetate and obtain intermediate TA-1, is not required to purification and is directly used in reaction in next step.
It is prepared by intermediate TA-5：
17.3g dissolves in the anhydrous THF of 70ml tert-butyl benzene acetonitrile, system is cooled to -5 DEG C of addition equimolar solid uncles Butanol potassium, then instillation equimolar intermediate C, 2.5hr are added dropwise under stiring, continue to stir 2.0hr, are then raised to room Temperature continues to be stirred to react 2hr, THF is steamed after the completion of reaction, residue water dissolution, it is 4 or so that pH, which is neutralized with hydrochloric acid, is used Ethyl acetate extracts, and is dried with anhydrous sodium sulfate, steams ethyl acetate and obtain intermediate TA-5, is not required to purification and is directly used in next step Reaction.
It is prepared by intermediate TA-6：
17.3g dissolves in 70mlTHF tert-butyl benzene acetonitrile, system is cooled to -5 DEG C of addition equimolar solid t-butyl alcohols Potassium, then instillation equimolar intermediate D-1,3.0hr are added dropwise under stiring, continue to stir 2.0hr, are then raised to room temperature, Continue to be stirred to react 2hr, methyl tertiary butyl ether(MTBE) is steamed after the completion of reaction, residue water dissolution, it is 4 left that pH, which is neutralized with hydrochloric acid, The right side is extracted with ethyl acetate, and is dried with anhydrous sodium sulfate, steams ethyl acetate and obtains intermediate TA-3, is not required to purification and is directly used in It reacts in next step.
It is prepared by embodiment 2, target compound
(1) target compound 226
By 0.31g (0.001mol) intermediate TA-1 and 0.12g (0.0011mol) intermediate F-1,0.15 sodium carbonate and Catalytic amount sodium iodide is added in 25ml acetonitriles, then heating reflux reaction 7hr, and plate layer chromatography tracking reaction is completed, reaction system It is cooled to room temperature, filters off solid, steams acetonitrile, residue column chromatography purifies to obtain product 0.32g, yield 84%.
(2) target compound 251
By 31g (0.1mol) intermediate TA-1 and 13g (0.11mol) intermediate F-2,15 sodium carbonate and catalytic amount iodate Sodium is added in 250ml acetonitriles, then heating reflux reaction 10hr, and plate layer chromatography tracking reaction is completed, and reaction system is cooled to room Temperature filters off solid, steams acetonitrile, and residue column chromatography purifies to obtain product 35.1g, yield 89%.
(3) target compound 259
By 0.31g (0.001mol) intermediate TA-1 and 0.13g (0.0011mol) intermediate F-3,0.15 sodium carbonate and Catalytic amount sodium iodide is added in 25ml acetone, then heating reflux reaction 12hr, and plate layer chromatography tracking reaction is completed, reaction system It is cooled to room temperature, filters off solid, steams acetonitrile, residue column chromatography purifies to obtain product 0.28g, yield 66%.
(4) target compound 326
By 0.34g (0.001mol) intermediate TA-2 and 0.13g (0.0011mol) intermediate F-2,0.15 sodium carbonate and Catalytic amount sodium iodide is added to 25N, in dinethylformamide, then heats 70 DEG C of reaction 4hr, plate layer chromatography tracking has been reacted At reaction system is cooled to room temperature, filters off solid, and decompression steams solvent, and residue column chromatography purifies to obtain product 0.24g, receives Rate is 56%.
(5) target compound 401
By 0.32g (0.001mol) intermediate TA-2 and 0.13g (0.0011mol) intermediate F-2,0.15 sodium carbonate and Catalytic amount sodium iodide is added in 25ml acetonitriles, then heating reflux reaction 11hr, and plate layer chromatography tracking reaction is completed, reaction system It is cooled to room temperature, filters off solid, decompression steams solvent, and residue column chromatography purifies to obtain product 0.29g, yield 71%.
(6) target compound 105
By 0.33g (0.1mol) intermediate TA-5 and 0.18g (0.11mol) intermediate F-4,0.15 sodium carbonate and catalysis Amount sodium iodide is added in 25ml acetonitriles, then heating reflux reaction 11hr, and plate layer chromatography tracking reaction is completed, reaction system cooling To room temperature, solid is filtered off, steams acetonitrile, residue column chromatography purifies to obtain product 0.25g, yield 55%.
(7) target compound 4
By 0.295g (0.1mol) intermediate TA-4 and 0.15g (0.11mol) intermediate F-6,0.15 sodium carbonate and urge Change amount sodium iodide is added in 25ml acetonitriles, then heating reflux reaction 5hr, and plate layer chromatography tracking reaction is completed, and reaction system is cold But room temperature is arrived, solid is filtered off, steams acetonitrile, residue column chromatography purifies to obtain product 0.31g, yield 78%.
(8) target compound 91
By 0.33g (0.1mol) intermediate TA-5 and 0.18g (0.11mol) intermediate F-4,0.15 sodium carbonate and catalysis Amount sodium iodide is added in 25ml acetonitriles, then heating reflux reaction 11hr, and plate layer chromatography tracking reaction is completed, reaction system cooling To room temperature, solid is filtered off, steams acetonitrile, residue column chromatography purifies to obtain product 0.25g, yield 55%.
(9) target compound 548
By 0.31g (0.001mol) intermediate TA-1 and 0.16g (0.0011mol) intermediate H-1,0.15 sodium carbonate and Catalytic amount sodium iodide is added in 25ml acetonitriles, then heating reflux reaction 6hr, and plate layer chromatography tracking reaction is completed, reaction system It is cooled to room temperature, filters off solid, steams acetonitrile, residue column chromatography purifies to obtain product 0.33g, yield 78%.
(10) target compound 739
By 0.34g (0.001mol) intermediate TA-2 and 0.13g (0.0011mol) intermediate H-2,0.15 potassium carbonate and Catalytic amount sodium iodide is added to 25N, in dinethylformamide, then heats 70 DEG C of reaction 5hr, plate layer chromatography tracking has been reacted At reaction system is cooled to room temperature, filters off solid, and decompression steams solvent, and residue column chromatography purifies to obtain product 0.28g, receives Rate is 65%.
(11) target compound 835
By 0.31g (0.001mol) intermediate TA-6 and 0.13g intermediate H-3,0.15 potassium carbonate and catalytic amount iodate Sodium is added in 25mlTHF, then heating reflux reaction 10hr, and plate layer chromatography tracking reaction is completed, and reaction system is cooled to room temperature, Solid is filtered off, acetonitrile is steamed, residue column chromatography purifies to obtain product 0.25g, yield 61%.
Two, preparation is prepared
Following embodiment is prepared according to quality proportioning.
Embodiment 3,30% suspending agent
Compound 251 and other components are fully mixed, thus obtained 30% suspending agent.It is outstanding to be diluted with water to obtain 30% The dilution of any required concentration can be obtained in floating agent.
Embodiment 4,30% missible oil
Phosphorous acid is dissolved in toluene, compound 548 and ethoxylated triglycerides are added, is obtained transparent molten Liquid, i.e. 30% missible oil.
Embodiment 5,60% wettable powder
Compound 91, dodecyl sodium naphthalene sulfonate, sodium lignin sulfonate and silicon bath soil are mixed, in pulverizer It crushes, up to 60% wettable powder after particle reaches standard.
Three, biological activity test
Embodiment 6, to Tetranychus cinnabarinus ovum determination of activity
According to the dissolubility of untested compound, active compound is dissolved with n,N-Dimethylformamide, then with containing 1 ‰ Tween 80 water Solution is configured to the prepare liquid of required concentration, and the content of n,N-Dimethylformamide in the solution is no more than 10%.
Using spray-on process.Broad Bean Leaves band handle is cut, is inserted in the bottle for adding water.Connect it is a certain number of female at mite, for 24 hours after Mite is removed into, removes and carries out spraying treatment afterwards for 24 hours at mite, experiment is repeated 3 times, and sets blank control, is placed in observation ward (26 ± 2 DEG C, humidity 70%~80%, 16h illumination/d) in culture, after blank control hatching after investigation result.It is not hatch when investigation It is dead.
According to the method described above, determination of activity find the following compound 1-17,26-72 of the present invention, 76-92,101-117, 151-167、176-192、226-242、251-267、301-317、326-342、376-392、401-417、451-454、456、 457、458、460、467、468、471、474、476、477、480、481、483-486、488、489、490、492、494、499、 500、503、506、508、509、512、513、574-548、549、550、552、553、554、556、558、563、564、567、 570、572、573、576、577、579-582、584、585、586、588、590、595、596、599、606、602、604、606、 608、609、643-646、648、649、650、652、654、659、660、663、666、668、669、972、673、675-678、 680、681、682、684、691、692、695、698、700、701、704、705、739-742、744、745、746、748、750、 755、757、759、762、764、765、768、769、771-774、776、777、778、780、782、787、788、791、794、 796、797、801、835-838、840、841、842、844、846、851、853、855、858、860、862、864、865、867- 870、872、873、874、876、878、883、884、887、890、892、894、896、897、931-934、936、937、938、 940、942、947、948、951、956、958、961、960、963-966、968、969、970、972、974、978、980、986、 988,983,989,992,993,1158,1172,1293,1318,1323,1468 it is parity with or superiority over 90% at concentration 5mg/L Ovicidal activity.Compared with PCT Patent Application WO01/68589, compound 8-1 disclosed in PCT Patent Application WO01/68589, 8-2,8-3, the 8-4 ovicidal activity at concentration 5mg/L are less than 30%.
According to the method described above, determination of activity find the following compound of the present invention 230,234,226,227,251,252,254, 255、259、301、302、305、309、326、327、401、402、409、405、547、548、549、550、553、570、579、 580,585,602,771,772,780,931,932,933,940,937,963,964 and 969 are equal to or excellent at concentration 2mg/L In 90% ovicidal activity.Compared with PCT Patent Application WO01/68589, chemical combination disclosed in PCT Patent Application WO01/68589 Object 8-1,8-2,8-3, the 8-4 ovicidal activity at concentration 2mg/L are 0%.
According to the method described above, choose compound 226,227,230,234,251,252,254,255,301,302,547, 585, compound 8-1,8-2,8-3 and 8-4 disclosed in 771,772,931,932 and 937 and PCT Patent Application WO01/68589 The parallel determination of ovicidal activity is carried out, test result is shown in Table 4；
Table 4
Embodiment 7, to Tetranychus cinnabarinus at the active measurement of mite
According to the dissolubility of untested compound, active compound is dissolved with n,N-Dimethylformamide, then with containing 1 ‰ Tween 80 water Solution is configured to the prepare liquid of required concentration, and the content of n,N-Dimethylformamide in the solution is no more than 10%.
Two panels true leaf Kidney bean seedling, inoculation Tetranychus cinnabarinus is taken to carry out whole strain spray with manual sprayer at mite and after investigating radix Mist processing, often handles 3 repetitions, and processing is placed on standard sight room, survival mite number is investigated after 48h, calculates the death rate.
According to the method described above, determination of activity finds the compounds of this invention 1-17,26-72,76-92,101-117,151- 167、176-192、226-242、251-267、301-317、326-342、376-392、401-417、451-454、456、457、 458、460、467、468、471、474、476、477、480、481、483-486、488、489、490、492、494、499、500、 503、506、508、509、512、513、574-548、549、550、552、553、554、556、558、563、564、567、570、 572、573、576、577、579-582、584、585、586、588、590、595、596、599、606、602、604、606、608、 609、643-646、648、649、650、652、654、659、660、663、666、668、669、972、673、675-678、680、 681、682、684、691、692、695、698、700、701、704、705、739-742、744、745、746、748、750、755、 757、759、762、764、765、768、769、771-774、776、777、778、780、782、787、788、791、794、796、 797、801、835-838、840、841、842、844、846、851、853、855、858、860、862、864、865、867-870、 872、873、874、876、878、883、884、887、890、892、894、896、897、931-934、936、937、938、940、 942、947、948、951、956、958、961、960、963-966、968、969、970、972、974、978、980、986、988、 983, it 989,992,993,1158,1172,1293,1318,1323,1468 it is parity with or superiority over 90% at concentration 2.5mg/L kills At mite activity.Compared with PCT Patent Application WO01/68589, compound 8-1 disclosed in PCT Patent Application WO01/68589, 8-2,8-3,8-4 are less than 80% at concentration 2.5mg/L at mite active.
According to the method described above, determination of activity find the compounds of this invention 230,234,226,227,251,252,254,255, 259、301、302、305、309、326、327、401、402、409、405、547、548、549、550、553、570、579、580、 585,602,771,772,780,931,932,933,940,937,963,964 and 969 are equal to or excellent at concentration 1.25mg/L Mite activity is killed into 90%.Compared with PCT Patent Application WO01/68589, change disclosed in PCT Patent Application WO01/68589 It closes object 8-1,8-2,8-3,8-4 and is less than 50% at mite activity at concentration 1.25mg/L.
According to the method described above, choose compound 226,227,230,234,251,252,254,255,301,302,547, 585, compound 8-1,8-2,8-3 and 8-4 disclosed in 771,772,931,932 and 937 and PCT Patent Application WO01/68589 The active parallel determination of mite is carried out into, test result is shown in Table 5.
Table 5
Embodiment 8, to the active measurement of Tetranychus cinnabarinus deutonymph
According to the dissolubility of untested compound, active compound is dissolved with n,N-Dimethylformamide, then with containing 1 ‰ Tween 80 water Solution is configured to the prepare liquid of required concentration, and the content of n,N-Dimethylformamide in the solution is no more than 10%.
Broad Bean Leaves band handle is cut, insert in plus the bottle of water in, to connect that certain amount body colour is bright-coloured, action is active female at Mite, for 24 hours after, removal removes the insufficient blade of ovum amount at mite.It waits for egg hatching, spraying treatment is carried out after length to deutonymph, experiment repeats 3 times, and set blank control, it is placed in culture in observation ward's (26 ± 2 DEG C, humidity 70%~80%, 16h illumination/d), is investigated after 48h As a result.Polypide is touched when investigation, is not reacted and is considered as dead worm.
According to the method described above, determination of activity finds the compounds of this invention 1-17,26-72,76-92,101-117,151- 167、176-192、226-242、251-267、301-317、326-342、376-392、401-417、451-454、456、457、 458、460、467、468、471、474、476、477、480、481、483-486、488、489、490、492、494、499、500、 503、506、508、509、512、513、574-548、549、550、552、553、554、556、558、563、564、567、570、 572、573、576、577、579-582、584、585、586、588、590、595、596、599、606、602、604、606、608、 609、643-646、648、649、650、652、654、659、660、663、666、668、669、972、673、675-678、680、 681、682、684、691、692、695、698、700、701、704、705、739-742、744、745、746、748、750、755、 757、759、762、764、765、768、769、771-774、776、777、778、780、782、787、788、791、794、796、 797、801、835-838、840、841、842、844、846、851、853、855、858、860、862、864、865、867-870、 872、873、874、876、878、883、884、887、890、892、894、896、897、931-934、936、937、938、940、 942、947、948、951、956、958、961、960、963-966、968、969、970、972、974、978、980、986、988、 983, it 989,992,993,1158,1172,1293,1318,1323,1468 it is parity with or superiority over 95% at concentration 2.5mg/L kills Deutonymph activity.Compared with PCT Patent Application WO01/68589, compound 8-1 disclosed in PCT Patent Application WO01/68589, 8-2,8-3,8-4 the deutonymph active at concentration 2.5mg/L are less than 80%.
According to the method described above, determination of activity find the compounds of this invention 230,234,226,227,251,252,254,255, 259、301、302、305、309、326、327、401、402、409、405、547、548、549、550、553、570、579、580、 585, it 602,771,772,780,931,932,933,940,937,963,964 and 969 is parity with or superiority at concentration 0.5mg/L 90% kills deutonymph activity.Compared with PCT Patent Application WO01/68589, chemical combination disclosed in PCT Patent Application WO01/68589 Object 8-1,8-2,8-3,8-4 the deutonymph activity at concentration 0.5mg/L are less than 30%.
According to the method described above, choose compound 226,227,230,234,251,252,254,255,301,302,547, 585, compound 8-1,8-2,8-3 and 8-4 disclosed in 771,772,931,932 and 937 and PCT Patent Application WO01/68589 The active parallel determination of deutonymph is carried out, test result is shown in Table 6.
Table 6

Claims (16)

1. Set of Pyrazole Derivatives has following general formula stru-1：
Wherein：
R1, R2, R3, R4, R5 are independently selected from hydrogen, halogen, nitro, itrile group, C1-C20Alkyl, C1-C20Halogenated alkyl, C2-C20Alkene Base, C2-C20Halogenated alkenyl, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkane Sulfenyl, C1-C20Halogenated alkylthio, C1-C20Alkane sulfoxide group, C1-C20Alkane sulfuryl, C1-C20Alkyl sulfonic acid ester group, C1-C20Alkyl carboxylic Acid esters, C1-C20Alkyl acyl, C1-C20Halogenated alkyl acyl group；
R6 is selected from hydrogen, halogen, nitro, itrile group, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkanes Base, C2-C20Alkenyl, C2-C20Halogenated alkenyl, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Haloalkoxy Base, C1-C20Alkylthio group, C1-C20Halogenated alkylthio, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Alkyl halide Base, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20 Halogenated alkylthio and C1-C20At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkane Base, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1- C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20At least one of alkane sulfuryl substitution pyridyl group, pyrazolyl, thiophene phenyl, Furyl or thiazolyl；
R7 is selected from hydrogen, halogen, nitro, itrile group, C1-C20Alkyl, C1-C20Halogenated alkyl, C1-C20Alcoxyl methylene；
R8 is selected from hydrogen, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alcoxyl is sub- Methyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated ring Alkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20In alkane sulfuryl At least one substituted phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Cycloalkanes Base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of at least one of alkane sulfuryl substitution；
R9 is selected from hydrogen, halogen, nitro, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C2- C20Alkenyl, C2-C20Halogenated alkenyl, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1- C20Alkylthio group, C1-C20Halogenated alkylthio, C1-C20Alkane sulfuryl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20 Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Haloalkoxy Base, C1-C20Alkylthio group, C1-C20Halogenated alkylthio and C1-C20Pyridyl group, pyrazolyl, the thiophene of at least one of alkane sulfuryl substitution Phenolic group, furyl or thiazolyl；
L is selected from oxygen, sulphur, methylene, nitrogen；
Q is selected from oxygen, sulphur；
R10 is selected from hydrogen, halogen, nitro, C1-C20Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C2-C20Alkenyl, C2-C20Halogenated alkenyl, C2-C20Alkynyl, C2-C20Halo alkynyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group, C1-C20Halogenated alkylthio, C1-C20Alkyl carboxylic acid ester, by selected from hydrogen, halogen, nitro, cyano, C1-C20Alkane Base, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1- C20Alkylthio group and C1-C20At least one of halogenated alkylthio substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C20 Alkyl, C1-C20Halogenated alkyl, C3-C20Naphthenic base, C3-C20Halogenated cycloalkyl, C1-C20Alkoxy, C1-C20Halogenated alkoxy, C1-C20Alkylthio group and C1-C20Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiophene of at least one of halogenated alkylthio substitution Oxazolyl.
2. pyrazole derivatives described in accordance with the claim 1, it is characterised in that in the general formula stru-1：
R1, R2, R3, R4, R5 are independently selected from hydrogen, halogen, nitro, itrile group, C1-C10Alkyl, C1-C10Halogenated alkyl, C2-C10Alkene Base, C2-C10Halogenated alkenyl, C2-C10Alkynyl, C2-C10Halo alkynyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkane Sulfenyl, C1-C10Halogenated alkylthio, C1-C10Alkane sulfoxide group, C1-C10Alkane sulfuryl, C1-C10Alkyl sulfonic acid ester group, C1-C10Alkyl carboxylic Acid esters, C1-C10Alkyl acyl, C1-C10Halogenated alkyl acyl group；
R6 is selected from hydrogen, halogen, nitro, itrile group, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkanes Base, C2-C10Alkenyl, C2-C10Halogenated alkenyl, C2-C10Alkynyl, C2-C10Halo alkynyl, C1-C10Alkoxy, C1-C10Haloalkoxy Base, C1-C10Alkylthio group, C1-C10Halogenated alkylthio, by selected from hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10Alkyl halide Base, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10 Halogenated alkylthio and C1-C10At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C10Alkane Base, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1- C10Alkylthio group, C1-C10Halogenated alkylthio and C1-C10At least one of alkane sulfuryl substitution pyridyl group, pyrazolyl, thiophene phenyl, Furyl or thiazolyl；
R7 is selected from hydrogen, halogen, nitro, itrile group, C1-C10Alkyl, C1-C10Halogenated alkyl, C1-C10Alcoxyl methylene；
R8 is selected from hydrogen, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alcoxyl is sub- Methyl, by selected from hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated ring Alkyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio and C1-C10In alkane sulfuryl At least one substituted phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Cycloalkanes Base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio and C1-C10Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of at least one of alkane sulfuryl substitution；
R9 is selected from hydrogen, halogen, nitro, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C2- C10Alkenyl, C2-C10Halogenated alkenyl, C2-C10Alkynyl, C2-C10Halo alkynyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1- C10Alkylthio group, C1-C10Halogenated alkylthio, C1-C10Alkane sulfuryl, by selected from hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10 Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio and C1-C10At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10Haloalkoxy Base, C1-C10Alkylthio group, C1-C10Halogenated alkylthio and C1-C10Pyridyl group, pyrazolyl, the thiophene of at least one of alkane sulfuryl substitution Phenolic group, furyl or thiazolyl；
L is selected from oxygen, sulphur, methylene, nitrogen；
Q is selected from oxygen, sulphur；
R10 is selected from hydrogen, halogen, nitro, C1-C10Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C2-C10Alkenyl, C2-C10Halogenated alkenyl, C2-C10Alkynyl, C2-C10Halo alkynyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group, C1-C10Halogenated alkylthio, C1-C10Alkyl carboxylic acid ester, by selected from hydrogen, halogen, nitro, cyano, C1-C10Alkane Base, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1- C10Alkylthio group and C1-C10At least one of halogenated alkylthio substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C10 Alkyl, C1-C10Halogenated alkyl, C3-C10Naphthenic base, C3-C10Halogenated cycloalkyl, C1-C10Alkoxy, C1-C10Halogenated alkoxy, C1-C10Alkylthio group and C1-C10Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiophene of at least one of halogenated alkylthio substitution Oxazolyl.
3. pyrazole derivatives according to claim 2, it is characterised in that in the general formula stru-1：
R1, R2, R3, R4, R5 are independently selected from hydrogen, halogen, nitro, itrile group, C1-C6Alkyl, C1-C6Halogenated alkyl, C2-C6Alkene Base, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, C1-C6Alkane sulfoxide group, C1-C6Alkane sulfuryl, C1-C6Alkyl sulfonic acid ester group, C1-C6Alkyl carboxylic acid ester, C1-C6 Alkyl acyl, C1-C6Halogenated alkyl acyl group；
R6 is selected from hydrogen, halogen, nitro, itrile group, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C2-C6Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6 Alkylthio group, C1-C6Halogenated alkylthio, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Cycloalkanes Base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio and C1-C6 At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Alkyl halide sulphur Base and C1-C6Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of at least one of alkane sulfuryl substitution；
R7 is selected from hydrogen, halogen, nitro, itrile group, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alcoxyl methylene；
R8 is selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alcoxyl methylene, By selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1- C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio and C1-C6At least one of alkane sulfuryl takes The phenyl in generation, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated ring Alkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio and C1-C6In alkane sulfuryl extremely Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of a few substitution；
R9 is selected from hydrogen, halogen, nitro, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C2-C6 Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkane sulphur Base, C1-C6Halogenated alkylthio, C1-C6Alkane sulfuryl, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Alkyl halide sulphur Base and C1-C6At least one of alkane sulfuryl substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogen Substituted alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6 Halogenated alkylthio and C1-C6Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of at least one of alkane sulfuryl substitution；
L is selected from oxygen, sulphur, methylene, nitrogen；
Q is selected from oxygen, sulphur；
R10 is selected from hydrogen, halogen, nitro, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C2-C6 Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkane sulphur Base, C1-C6Halogenated alkylthio, C1-C6Alkyl carboxylic acid ester, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Alkyl halide Base, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group and C1-C6It is halogenated At least one of alkylthio group substitution phenyl, by selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Naphthenic base, C3-C6Halogenated cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group and C1-C6Alkyl halide Pyridyl group, pyrazolyl, thiophene phenyl, furyl or the thiazolyl of at least one of sulfenyl substitution.
4. pyrazole derivatives described in accordance with the claim 3, it is characterised in that in the general formula stru-1：
R1, R2, R3, R4, R5 are independently selected from hydrogen, fluorine, chlorine, bromine, nitro, itrile group, methyl, ethyl, isopropyl, tertiary butyl, three Methyl fluoride, methoxyl group, ethyoxyl, trifluoromethoxy, difluoro-methoxy, difluoroethoxy, methyl mercapto, trifluoromethylthio, trifluoro Ethylmercapto group, methylsulfonyl, methylsulphur base ester；
R6 is selected from hydrogen, fluorine, chlorine, bromine, nitro, itrile group, methyl, ethyl, isopropyl, cyclopropyl, methoxyl group, ethyoxyl, fluoroform Base, difluoromethyl, rubigan, p-fluorophenyl；
R7 is selected from hydrogen, halogen, nitro, itrile group, C1-C5Alkyl, C1-C5Halogenated alkyl, C1-C5Alcoxyl methylene；
R8 is selected from hydrogen, methyl, ethyl, a methyl fluoride, difluoromethyl, trifluoromethyl, methoxymethylene, ethoxymeyhylene；
R9 is selected from hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, propyl, isopropyl, difluoromethyl, cyclopropyl, methyl mercapto methylene Base, phenyl, rubigan, p-fluorophenyl, benzyl；
L is selected from oxygen, sulphur, methylene, nitrogen；
Q is selected from oxygen, sulphur；
R10 is selected from hydrogen, fluorine, chlorine, nitro, C1-C6Alkyl, C3-C6Naphthenic base, C3-C6Halogenated alkyl, C2-C6Alkenyl, C2-C6It is halogenated Alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Alkyl halide Sulfenyl, C1-C6Alkyl carboxylic acid methyl esters, C1-C6Alkyl carboxylic acid ethyl ester, by selected from hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, second At least one substituted phenyl in base, trifluoromethyl, methoxyl group, ethyoxyl, trifluoro ethoxy and methyl mercapto, by selected from hydrogen, fluorine, It is at least one in chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxyl group, ethyoxyl, trifluoro ethoxy and methyl mercapto Substituted pyridyl group, pyrazolyl, thiophene phenyl, furyl or thiazolyl.
5. pyrazole derivatives according to claim 4, it is characterised in that in the general formula stru-1：
R1, R2, R3, R4, R5 are independently selected from hydrogen, fluorine, chlorine, bromine, nitro, itrile group, methyl, ethyl, isopropyl, tertiary butyl, three Methyl fluoride, methoxyl group, ethyoxyl, trifluoromethoxy, difluoro-methoxy, difluoroethoxy, methyl mercapto, trifluoromethylthio, trifluoro Ethylmercapto group, methylsulfonyl, methylsulphur base ester；
R6 is selected from hydrogen, fluorine, chlorine, bromine, nitro, itrile group, methyl, ethyl, isopropyl, cyclopropyl, trifluoromethyl, difluoromethyl, first Oxygroup, ethyoxyl, rubigan, p-fluorophenyl；
R7 is selected from hydrogen, halogen, nitro, itrile group, C1-C5Alkyl, C1-C5Halogenated alkyl, C1-C5Alcoxyl methylene；
R8 is selected from methyl, ethyl；
R9 is selected from hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, propyl, isopropyl, difluoromethyl, cyclopropyl, methyl mercapto methylene Base, phenyl, rubigan, p-fluorophenyl, benzyl；
L is selected from oxygen, sulphur, methylene；
Q is selected from oxygen, sulphur；
R10 is selected from hydrogen, fluorine, chlorine, nitro, C1-C6Alkyl, C3-C6Naphthenic base, C3-C6Halogenated alkyl, C2-C6Alkenyl, C2-C6It is halogenated Alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Alkyl halide Sulfenyl, C1-C6Alkyl carboxylic acid methyl esters, C1-C6Alkyl carboxylic acid ethyl ester, by selected from hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, second At least one substituted phenyl in base, trifluoromethyl, methoxyl group, ethyoxyl, trifluoro ethoxy and methyl mercapto, by selected from hydrogen, fluorine, It is at least one in chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxyl group, ethyoxyl, trifluoro ethoxy and methyl mercapto Substituted pyridyl group, pyrazolyl, thiophene phenyl, furyl or thiazolyl.
6. pyrazole derivatives according to claim 4, it is characterised in that in the general formula stru-1：
R1, R2, R4, R5 are selected from hydrogen；
R3 is selected from tertiary butyl；
R6 is selected from hydrogen, fluorine, chlorine, bromine, nitro, itrile group, methyl, ethyl, isopropyl, cyclopropyl, trifluoromethyl, difluoromethyl, first Oxygroup, ethyoxyl, rubigan, p-fluorophenyl；
R7 is selected from hydrogen, halogen, nitro, itrile group, C1-C5Alkyl, C1-C5Halogenated alkyl, C1-C5Alcoxyl methylene；
R8 is selected from methyl, ethyl；
R9 is selected from hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, propyl, isopropyl, difluoromethyl, cyclopropyl, methyl mercapto methylene Base, phenyl, rubigan, p-fluorophenyl, benzyl；
L is selected from oxygen, sulphur, methylene；
Q is selected from oxygen, sulphur；
R10 is selected from hydrogen, fluorine, chlorine, nitro, C1-C6Alkyl, C3-C6Naphthenic base, C3-C6Halogenated alkyl, C2-C6Alkenyl, C2-C6It is halogenated Alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Alkyl halide Sulfenyl, C1-C6Alkyl carboxylic acid methyl esters, C1-C6Alkyl carboxylic acid ethyl ester, by selected from hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, second At least one substituted phenyl in base, methoxyl group, ethyoxyl, trifluoromethyl, trifluoro ethoxy and methyl mercapto, by selected from hydrogen, fluorine, It is at least one in chlorine, bromine, nitro, cyano, methyl, ethyl, methoxyl group, ethyoxyl, trifluoromethyl, trifluoro ethoxy and methyl mercapto Substituted pyridyl group, pyrazolyl, thiophene phenyl, furyl or thiazolyl.
7. pyrazole derivatives according to claim 4, it is characterised in that the pyrazole derivatives are selected from following structural formula institute Show at least one of compound：
8. according to the pyrazole derivatives described in one of claim 1 to 7, it is characterised in that pyrazoles spreads out shown in the general formula stru-1 Biology is selected from least one of E formulas pyrazole derivatives and Z formula pyrazole derivatives.
9. the preparation method of pyrazole derivatives shown in a kind of general formula stru-1, it is characterised in that the method includes：
The X is selected from halogen.
10. preparation method according to claim 9, it is characterised in that：
The alkali be selected from least one of organic base and inorganic base, it is described acid in organic acid and inorganic acid at least one Kind, the solvent is selected from potassium iodide, iodine independently selected from least one of protonic solvent and non-protonic solvent, catalyst Change at least one of sodium and phase transfer catalyst.
11. preparation method according to claim 10, it is characterised in that：
The X is selected from chlorine, bromine or iodine, and the alkali is selected from sodium carbonate, potassium carbonate, sodium bicarbonate, saleratus, sodium hydroxide, hydrogen At least one of potassium oxide, sodium hydride, sodium alkoxide and potassium alcoholate, the acid is selected from least one of hydrochloric acid, sulfuric acid and acetic acid, institute Solvent is stated in acetone, methyl ethyl ketone, tetrahydrofuran, acetonitrile, N, dinethylformamide, toluene and chlorobenzene It is at least one.
12. the application of pyrazole derivatives shown in a kind of general formula stru-1, it is characterised in that the pyrazole derivatives are for preventing Pest.
13. the application of pyrazole derivatives according to claim 12, it is characterised in that the pyrazole derivatives are for preventing Selected from Isopoda, times sufficient mesh, lip foot mesh, comprehensive mesh, Thysanoptera, Collembola, Orthoptera, Blattaria, Dermaptera, Isoptera, lice Mesh, Thysanoptera, Heteroptera, Homoptera, Lepidoptera, coleoptera, Hymenoptera, Diptera, Siphonaptera, Arachnoidea and plant nematode At least one of.
14. the application of pyrazole derivatives according to claim 13, it is characterised in that the plant nematode is selected from short Body Turbatrix, Radopholus similis Throne, fuller's teasel Ditylenchus dipsaci, Tylenchulus Semipenetrans, Heterodera, ball Heterodera, root knot line At least one of Eimeria, Aphelenchoides, minute hand Turbatrix, Xiphinema, burr Turbatrix and Bursaphelenchus.
15. the application of pyrazole derivatives according to claim 12, it is characterised in that the pyrazole derivatives are for preventing On crop at least one of mite, deutonymph, mite ovum, aphid and plant hopper.
16. a kind of agricultural insecticidal, acaricide, it is characterised in that the Insecticidal and acaricidal agent contains 0.1~99% mass percentage General formula stru-1 shown in compound.
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