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CN109836418A - Substituted pyrazolecarboxylic class compound and preparation method thereof and purposes as insecticidal/acaricidal agent - Google Patents

Substituted pyrazolecarboxylic class compound and preparation method thereof and purposes as insecticidal/acaricidal agent Download PDF

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Publication number
CN109836418A
CN109836418A CN201711223553.3A CN201711223553A CN109836418A CN 109836418 A CN109836418 A CN 109836418A CN 201711223553 A CN201711223553 A CN 201711223553A CN 109836418 A CN109836418 A CN 109836418A
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China
Prior art keywords
alkyl
halogenated
carbonyl
alkoxy
amino
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CN201711223553.3A
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Chinese (zh)
Inventor
李淼
杨吉春
常秀辉
孙金强
宋玉泉
许磊川
关爱莹
刘长令
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Application filed by Shenyang Sinochem Agrochemicals R&D Co Ltd filed Critical Shenyang Sinochem Agrochemicals R&D Co Ltd
Priority to CN201711223553.3A priority Critical patent/CN109836418A/en
Priority to US16/766,925 priority patent/US11457628B2/en
Priority to CN201880064173.6A priority patent/CN111263757A/en
Priority to PCT/CN2018/116938 priority patent/WO2019105275A1/en
Priority to BR112020010921-5A priority patent/BR112020010921B1/en
Priority to EP18882912.1A priority patent/EP3719015A4/en
Publication of CN109836418A publication Critical patent/CN109836418A/en
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Abstract

The invention discloses a kind of substituted pyrazolecarboxylic class compounds, and structure is as shown in general formula I: each substituent group is defined in the specification in formula.The compound of the present invention has broad spectrum disinfestation mite killing activity, has excellent control efficiency to aphid, Tetranychus cinnabarinus etc., good effect is obtained under very low dosage.

Description

Substituted pyrazolecarboxylic class compound and preparation method thereof and purposes as insecticidal/acaricidal agent
Technical field
The invention belongs to agricultural insecticidal acaricide fields, and in particular to a kind of novel substituted pyrazolecarboxylic class compound and its preparation Method and purposes as insecticidal/acaricidal agent.
Background technique
Patent WO9507278, WO2014063642A1 discloses the substituted pyrazolecarboxylic class compound containing pyrimidine and kills as agricultural The application of bacterium, Insecticidal and acaricidal agent etc., but structure substituted pyrazolecarboxylic class compound as shown in general formula I of the present invention differs greatly therewith, And have no document report.
Summary of the invention
The purpose of the present invention is to provide a kind of substituted pyrazolecarboxylic class compounds that can control various pests harmful mite, and its system The purposes of Preparation Method and the drug for preparing pest control harmful mite in agricultural or other field.
To achieve the above object, technical scheme is as follows:
The present invention provides a kind of substituted pyrazolecarboxylic class compound, and the substituted pyrazolecarboxylic class compound is the chemical combination as shown in general formula I Object,
In formula:
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C3-C12Cycloalkanes Base, C1-C12Alkoxy, halogenated C1-C12Alkoxy, C1-C12Alkylthio group, halogenated C1-C12Alkylthio group, C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphonyl, C2-C12Alkenyl, halogenated C2-C12Alkenyl, C2-C12Alkynyl, halogenated C2-C12Alkynyl, C3-C12Alkenyloxy group, Halogenated C3-C12Alkenyloxy group, C3-C12Alkynyloxy group, halogenated C3-C12Alkynyloxy group, C1-C12Alkyl amino, two (C1-C12Alkyl) amino, C1-C12Alkyl amino-carbonyl, halogenated C1-C12Alkyl amino-carbonyl, C1-C12Alkoxy carbonyl, halogenated C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl or C1-C2Alkylthio group C1-C12Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C1- C12Alkoxy or halogenated C1-C12Alkoxy；
R1And R2Also five yuan, hexa-atomic, seven yuan or octatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy, halogenated C1-C12Alkane Oxygroup, C3-C12Naphthenic base, C1-C12Alkylthio group, C2-C12Enylsulfanyl, C2-C12Alkenyl, C2-C12Alkynyl, halogenated C2-C12Alkenyl, Halogenated C2-C12Alkynyl, C1-C12Alkoxy C1-C12Alkyl, halogenated C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12 Alkyl, halogenated C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkyl sulphinyl, halogenated C1-C12Alkyl sulphinyl, C1-C12Alkane Base sulfonyl, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkyl amino sulfonyl, two (C1-C12Alkyl) amino-sulfonyl, C1- C12Alkylsulfonyl aminocarbonyl, C1-C12Alkyl-carbonyl-amino sulfonyl, C3-C12Cycloalkyloxycarbonyl, C1-C12Alkyl oxycarbonyl Base, halogenated C1-C12Alkyl-carbonyl, C1-C12Alkoxy carbonyl, halogenated C1-C12Alkoxy carbonyl, C1-C12Alkyl-carbonyl C1-C12 Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkyl amino-carbonyl, two (C1-C12Alkyl) amino carbonyl, C2-C12Alkene Epoxide carbonyl, C2-C12Alkynyloxycar bonyl, C1-C12Alkoxy C1-C12Alkoxy carbonyl, C1-C12Alkyl amino sulfenyl, two (C1- C12Alkyl) amino sulfenyl, the unsubstituted or aryl carbonyl C that are replaced by the following groups of 1-51-C6Alkyl, aryl carbonyl, virtue Epoxide carbonyl, aryl C1-C6Alkyloxycarbonyl, aryl C1-C6Alkyl, Heteroarylcarbonyl C1-C6It is alkyl, Heteroarylcarbonyl, miscellaneous Aryloxycarbonyl, heteroaryl C1-C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyl, following group are halogen, nitro, cyano, C1- C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy or Halogenated C1-C12Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C8Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy or Halogenated C1-C12Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C8Ring；
M is selected from 0 to 5 integer；
R8Selected from hydrogen, cyano, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy carbonyl, halogenated C1-C12 It is alkoxy carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxy group carbonyl Base, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C12Alkyl, C3-C8Naphthenic base, halogenated C1-C12Alkyl, C1-C12Alkyl-carbonyl, halogenated C1-C12 Alkyl-carbonyl, C1-C12Alkyl sulphonyl, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12 Alkyl, C1-C12Alkoxy carbonyl C1-C12It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, Arylmethyl carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy, halogen For C1-C12Alkoxy, C3-C12Naphthenic base, C1-C12Alkyl amino, halogenated C1-C12Alkyl amino, two (C1-C12Alkyl) amino, Halogenated two (C1-C12Alkyl) amino, C (=O) NR11R12、C1-C12Alkylthio group, halogenated C1-C12Alkylthio group, C2-C12Alkenyl, C2- C12Alkynyl, C2-C12Alkenyloxy group, halogenated C2-C12Alkenyloxy group, C2-C12Alkynyloxy group, halogenated C2-C12Alkynyloxy group, C1-C12Alkyl sulfonyl Base, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkyl-carbonyl, halogenated C1-C12Alkyl-carbonyl, C1-C12It is alkoxy carbonyl, halogenated C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl, halogenated C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1- C12Alkyl, halogenated C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, halogenated C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkylthiocarbonyl C1-C12Alkyl, halogenated C1-C12Alkylthiocarbonyl C1-C12Alkyl, C1-C12Alkyl oxycarbonyl Base oxygroup, halogenated C1-C12Alkyl carbonyl epoxide, C1-C12Alkoxy-carbonyl oxy, halogenated C1-C12Alkoxy-carbonyl oxy, C1- C12Alkyl sulphonyl oxygroup, halogenated C1-C12Alkyl sulphonyl oxygroup, C1-C12Alkoxy C1-C12Alkoxy or halogenated C1-C12Alkane Oxygroup C1-C12Alkoxy；
N is selected from 0 to 5 integer；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C3-C8Naphthenic base, C1-C12Alkoxy, C1-C12Alkane Sulfenyl or C1-C12Alkyl sulphonyl；
Or the salt of compound shown in general formula I.
In substituted pyrazolecarboxylic class compound of the present invention, optional compound includes: in shown general formula I:
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Naphthenic base, C1-C6Alkoxy, halogenated C1-C6Alkoxy, C1-C6Alkylthio group, C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halogenated C1- C6Alkylthio group, C2-C6Alkenyl, halogenated C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6Alkynyl, C3-C6Alkenyloxy group, halogenated C3-C6Alkene Oxygroup, C3-C6Alkynyloxy group, halogenated C3-C6Alkynyloxy group, C1-C6Alkyl amino, two (C1-C6Alkyl) amino, C1-C6Alkyl amino carbonyl Base, halogenated C1-C6Alkyl amino-carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkoxy C1-C6Alkane Base or C1-C6Alkylthio group C1-C6Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6 Alkoxy or halogenated C1-C6Alkoxy；
R1And R2Also five yuan or hexatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy, halogenated C1-C6Alcoxyl Base, C3-C6Naphthenic base, C1-C6Alkylthio group, C2-C6Enylsulfanyl, C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6It is alkenyl, halogenated C2-C6Alkynyl, C1-C6Alkoxy C1-C6Alkyl, halogenated C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group C1-C6It is alkyl, halogenated C1-C6Alkylthio group C1-C6Alkyl, C1-C6Alkyl sulphinyl, halogenated C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halogen For C1-C6Alkyl sulphonyl, C1-C6Alkyl amino sulfonyl, two (C1-C6Alkyl) amino-sulfonyl, C1-C6Alkyl sulphonyl ammonia Base carbonyl, C1-C6Alkyl-carbonyl-amino sulfonyl, C3-C6Cycloalkyloxycarbonyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl Carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkyl-carbonyl C1-C6Alkyl, C1-C6Alkoxy carbonyl C1-C6Alkyl, C1-C6Alkyl amino-carbonyl, two (C1-C6Alkyl) amino carbonyl, C2-C6Allyloxycarbonyl, C2-C6Alkynyloxy group carbonyl Base, C1-C6Alkoxy C1-C6Alkoxy carbonyl, C1-C6Alkyl amino sulfenyl, two (C1-C6Alkyl) amino sulfenyl, it is unsubstituted or The aryl carbonyl C being further substituted with by 1-5 following groups1-C6Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C6Alkane Base Epoxide carbonyl, aryl C1-C6Alkyl, Heteroarylcarbonyl C1-C6Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1- C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyl, following group are halogen, nitro, cyano, C1-C6Alkyl, halogenated C1-C6Alkane Base, C1-C6Alkoxy or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy or halogen For C1-C6Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C6Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy or halogen For C1-C6Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C6Ring；
M is selected from 0 to 4 integer；
R8Selected from hydrogen, cyano, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkane It is Epoxide carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, Heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C6Alkyl, C3-C6Naphthenic base, halogenated C1-C6Alkyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl Carbonyl, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkyl sulphonyl, C1-C6Alkoxy carbonyl, C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkoxy carbonyl C1-C6It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl Carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6It is alkoxy, halogenated C1-C6Alkoxy, C3-C6Naphthenic base, C1-C6Alkyl amino, halogenated C1-C6Alkyl amino, two (C1-C6Alkyl) amino, halogenated two (C1-C6Alkyl) amino, C (=O) NR11R12、C1-C6Alkylthio group, halogenated C1-C6Alkylthio group, C2-C6Alkenyl, C2-C6Alkynyl, C2- C6Alkenyloxy group, halogenated C2-C6Alkenyloxy group, C2-C6Alkynyloxy group, halogenated C2-C6Alkynyloxy group, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkane Base sulfonyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1- C6Alkoxy C1-C6Alkyl, halogenated C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group C1-C6Alkyl, halogenated C1-C6Alkylthio group C1-C6Alkyl, C1-C6Alkoxy carbonyl C1-C6Alkyl, halogenated C1-C6Alkoxy carbonyl C1-C6Alkyl, C1-C6Alkylthiocarbonyl C1-C6Alkyl, halogenated C1-C6Alkylthiocarbonyl C1-C6Alkyl, C1-C6Alkyl carbonyl epoxide, halogenated C1-C6Alkyl carbonyl epoxide, C1-C6Alkoxy-carbonyl oxy, halogenated C1-C6Alkoxy-carbonyl oxy, C1-C6Alkyl sulphonyl oxygroup, halogenated C1-C6Alkyl sulphur Acyloxy, C1-C6Alkoxy C1-C6Alkoxy or halogenated C1-C6Alkoxy C1-C6Alkoxy；
N is selected from 0 to 5 integer；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Naphthenic base, C1-C6Alkoxy, C1-C6Alkylthio group Or C1-C6Alkyl sulphonyl；
Or the salt of compound shown in general formula I.
In substituted pyrazolecarboxylic class compound of the present invention, more optional compound includes: in shown general formula I:
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, halogenated C1-C4Alkoxy, C1-C4Alkylthio group, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogenated C1- C4Alkylthio group, C2-C4Alkenyl, halogenated C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkynyl, C3-C4Alkenyloxy group, halogenated C3-C4Alkene Oxygroup, C3-C4Alkynyloxy group, halogenated C3-C4Alkynyloxy group, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl amino carbonyl Base, halogenated C1-C4Alkyl amino-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkane Base or C1-C4Alkylthio group C1-C4Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4 Alkoxy or halogenated C1-C4Alkoxy；
R1And R2Also five yuan or hexatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alcoxyl Base, C3-C4Naphthenic base, C1-C4Alkylthio group, C2-C4Enylsulfanyl, C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4It is alkenyl, halogenated C2-C4Alkynyl, C1-C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4It is alkyl, halogenated C1-C4Alkylthio group C1-C4Alkyl, C1-C4Alkyl sulphinyl, halogenated C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogen For C1-C4Alkyl sulphonyl, C1-C4Alkyl amino sulfonyl, two (C1-C4Alkyl) amino-sulfonyl, C1-C4Alkyl sulphonyl ammonia Base carbonyl, C1-C4Alkyl-carbonyl-amino sulfonyl, C3-C4Cycloalkyloxycarbonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl Carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, C2-C4Allyloxycarbonyl, C2-C4Alkynyloxy group carbonyl Base, C1-C4Alkoxy C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or The aryl carbonyl C being further substituted with by 1-5 following groups1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkane Base Epoxide carbonyl, aryl C1-C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1- C4Alkyloxycarbonyl, heteroaryl C1-C4Alkyl, following group are halogen, nitro, cyano, C1-C4Alkyl, halogenated C1-C4Alkane Base, C1-C4Alkoxy or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy or halogen For C1-C4Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C4Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy or halogen For C1-C4Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C4Ring；
M is selected from 0 to 3 integer；
R8Selected from hydrogen, cyano, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkane It is Epoxide carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, Heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C4Alkyl, C3-C4Naphthenic base, halogenated C1-C4Alkyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl Carbonyl, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkyl sulphonyl, C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkyl, C1- C4Alkoxy carbonyl C1-C4It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl Base, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4It is alkoxy, halogenated C1-C4Alkoxy, C3-C4Naphthenic base, C1-C4Alkyl amino, halogenated C1-C4Alkyl amino, two (C1-C4Alkyl) amino, halogenated two (C1-C4Alkyl) amino, C (=O) NR12R13、C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C2-C4Alkenyl, C2-C4Alkynyl, C2- C4Alkenyloxy group, halogenated C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halogenated C2-C4Alkynyloxy group, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkane Base sulfonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1- C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkylthio group C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, halogenated C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkylthiocarbonyl C1-C4Alkyl, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4Alkoxy-carbonyl oxy, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphur Acyloxy, C1-C4Alkoxy C1-C4Alkoxy or halogenated C1-C4Alkoxy C1-C4Alkoxy；
N is selected from 0 to 5 integer；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, C1-C4Alkylthio group Or C1-C4Alkyl sulphonyl；
Or the salt of compound shown in general formula I.
In substituted pyrazolecarboxylic class compound of the present invention, further alternative compound includes, compound shown in the general formula I Structure are as follows: I-A, I-B, I-C, I-D；
In formula:
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy or halogen For C1-C4Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C4Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy or halogen For C1-C4Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C4Ring；
M is selected from 0 to 3 integer；
R8、R9Identical or different is respectively selected from hydrogen, cyano, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alcoxyl Base carbonyl, halogenated C1-C4It is alkoxy carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, Fang Jia Base carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4It is alkoxy, halogenated C1-C4Alkoxy, C3-C4Naphthenic base, C1-C4Alkyl amino, halogenated C1-C4Alkyl amino, two (C1-C4Alkyl) amino, halogenated two (C1-C4Alkyl) amino, C (=O) NR11R12、C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C2-C4Alkenyl, C2-C4Alkynyl, C2- C4Alkenyloxy group, halogenated C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halogenated C2-C4Alkynyloxy group, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkane Base sulfonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1- C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkylthio group C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, halogenated C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkylthiocarbonyl C1-C4Alkyl, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4Alkoxy-carbonyl oxy, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphur Acyloxy, C1-C4Alkoxy C1-C4Alkoxy or halogenated C1-C4Alkoxy C1-C4Alkoxy；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It is identical or different；
R11、R12Identical or different is respectively selected from hydrogen, C1-C4Alkyl or halogenated C1-C4Alkyl；
W is selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, C1-C4Alkylthio group Or C1-C4Alkyl sulphonyl；
And when the compound is general formula I-D, X is O or S；
When the compound is general formula I-A and I-D,
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, halogenated C1-C4Alkoxy, C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C1-C4Alkyl sulphinyl, C1-C4Alkane Base sulfonyl, C2-C4Alkenyl, halogenated C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkynyl, C3-C4Alkenyloxy group, halogenated C3-C4Alkene Oxygroup, C3-C4Alkynyloxy group, halogenated C3-C4Alkynyloxy group, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl amino carbonyl Base, halogenated C1-C4Alkyl amino-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkane Base or C1-C4Alkylthio group C1-C4Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4 Alkoxy or halogenated C1-C4Alkoxy；
When the compound is general formula I-A, I-B and I-C,
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alcoxyl Base, C3-C4Naphthenic base, C1-C4Alkylthio group, C2-C4Enylsulfanyl, C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4It is alkenyl, halogenated C2-C4Alkynyl, C1-C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4It is alkyl, halogenated C1-C4Alkylthio group C1-C4Alkyl, C1-C4Alkyl sulphinyl, halogenated C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogen For C1-C4Alkyl sulphonyl, C1-C4Alkyl amino sulfonyl, two (C1-C4Alkyl) amino-sulfonyl, C1-C4Alkyl sulphonyl ammonia Base carbonyl, C1-C4Alkyl-carbonyl-amino sulfonyl, C3-C4Cycloalkyloxycarbonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl Carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, C2-C4Allyloxycarbonyl, C2-C4Alkynyloxy group carbonyl Base, C1-C4Alkoxy C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or The aryl carbonyl C being further substituted with by 1-5 following groups1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkane Base Epoxide carbonyl, aryl C1-C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1- C4Alkyloxycarbonyl, heteroaryl C1-C4Alkyl, following group are halogen, nitro, cyano, C1-C4Alkyl, halogenated C1-C4Alkane Base, C1-C4Alkoxy or halogenated C1-C4Alkoxy；
When the compound is general formula I-B,
R13、R14、R15Or R16Identical or different is respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4Alkane Base, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alkoxy or C3-C4Naphthenic base；
When the compound is general formula I-C,
R17、R18Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, Halogenated C1-C4Alkoxy, C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C3-C4It is naphthenic base, unsubstituted or by 1-5 R10Replace Aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroaryl Methyl carbonyl or Heteroaryloxycarbonyl；
Or the salt of compound shown in general formula I.
In substituted pyrazolecarboxylic class compound of the present invention, further optional compound includes, general formula I-A, I-B, I-C, I- In compound shown in D:
R4、R5Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, positive fourth It is base, sec-butyl, isobutyl group, tert-butyl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, different Butoxy or tert-butoxy；
R6、R7Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, positive fourth It is base, sec-butyl, isobutyl group, tert-butyl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, different Butoxy or tert-butoxy；
R8、R9Identical or different is respectively selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, normal-butyl, Zhong Ding Base, isobutyl group, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, one methyl fluoride of dichloro, methoxyl group, ethyoxyl, just Propoxyl group, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methyl mercapto, ethylmercapto group, trifluoromethoxy, Trifluoro ethoxy, methoxycarbonyl, ethoxy carbonyl, amino carbonyl, methylaminocarbonyl, ethyl aminocarbonyl or dimethylamino Carbonyl；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary fourth Base, a methyl fluoride, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, methyl mercapto, ethylmercapto group, Methyl sulphonyl or ethylsulfonyl；
And when the compound is general formula I-A and I-D,
R1Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, carboxyl, methyl, ethyl, n-propyl, isopropyl, positive fourth Base, sec-butyl, isobutyl group, tert-butyl, a methyl fluoride, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy methyl Base, ethoxyl methyl or trifluoroethoxy ylmethyl；
R2Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, carboxyl, formoxyl, methyl, ethyl, methoxyl group, ethoxy Base or trifluoro ethoxy；
When the compound is general formula I-A, I-B and I-C,
R3Selected from hydrogen, hydroxyl, formoxyl, acetyl group, propiono, bytyry, trifluoroacetyl group, benzoyl, methyl, second Base, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tert-butyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, Trifluoro ethoxy, cyclopropyl oxygroup, methyl mercapto, ethylmercapto group, allyl, propargyl, mesyl, ethylsulfonyl, trifluoroethyl Sulfonyl, aminosulfonyl, ethylamino sulfonyl, dimethylaminosulfonyl, lignocaine sulfonyl, methane sulfonylamino carbonyl Base, methoxycarbonyl, ethoxy carbonyl, propoxycarbonyl, isopropoxy carbonyl, amino-carbonyl, dimethyl-aminocarbonyl, ethylene Epoxide carbonyl, acetylene Epoxide carbonyl, methylamino sulfenyl, ethylamino sulfenyl or dimethylamino sulfenyl；
When the compound is general formula I-B,
R13、R14、R15Or R16It is identical or different be respectively selected from hydrogen, fluorine, chlorine, bromine, iodine, amino, cyano, nitro, methyl, Ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tert-butyl, trifluoromethyl, trichloromethyl, one chloromethane of difluoro Base, one methyl fluoride of dichloro, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, uncle Butoxy, trifluoromethoxy or trifluoro ethoxy；
When the compound is general formula I-C,
R17、R18Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, positive fourth Base, sec-butyl, isobutyl group, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, one methyl fluoride of dichloro, trifluoroethyl, Methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoro methoxy It is base, trifluoro ethoxy, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxy group Carbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
Or the salt of compound shown in general formula I.
In substituted pyrazolecarboxylic class compound of the present invention, further optional compound includes general formula I-A, I-B, I-C, I- In compound shown in D:
R4、R5Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine or methyl；
R6、R7It is selected from hydrogen；
R8For hydrogen or methyl；
R9Selected from hydrogen or methyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxyl group, methyl mercapto or fluoroform Oxygroup；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl；
And when the compound is general formula I-A and I-D,
R1Selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or difluoromethyl；
R2Selected from hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, formoxyl, methyl, ethyl, methoxy or ethoxy；
When the compound is general formula I-A, I-B and I-C,
R3Selected from hydrogen, methyl, acetyl group, trifluoroacetyl group, methoxyl group, methyl mercapto, allyl, mesyl, methylamino Sulfonyl, dimethylaminosulfonyl, methoxycarbonyl, amino-carbonyl, dimethyl-aminocarbonyl, methylamino sulfenyl or dimethylamino Sulfenyl；
When the compound is general formula I-B,
R13、R14、R15Or R16Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl；
When the compound is general formula I-C,
R17、R18Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine or iodine；
Or the salt of compound shown in general formula I.
In substituted pyrazolecarboxylic class compound of the present invention, more optional compound includes changing shown in general formula I-A, I-B, I-C, I-D It closes in object:
R4、R5It may be the same or different, be respectively selected from hydrogen or methyl；
R6、R7It is selected from hydrogen；
R8For hydrogen or methyl；
R9Selected from methyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxyl group, methyl mercapto or fluoroform Oxygroup；
N is selected from 1 to 5 integer, when n is greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine or iodine；
And when the compound is general formula I-A and I-D,
R1Selected from fluorine, chlorine, bromine, iodine, methyl, ethyl or difluoromethyl；
R2Selected from fluorine, chlorine, bromine, iodine, nitro, amino, formoxyl, methyl or methoxy；
When the compound is general formula I-A, I-B and I-C,
R3Selected from hydrogen, methyl, acetyl group, methoxyl group, allyl, mesyl, methoxycarbonyl, amino-carbonyl, two Amino-carbonyl or dimethylamino sulfenyl；
When the compound is general formula I-B,
R13、R14、R15、R16It is selected from hydrogen；
When the compound is general formula I-C,
R17Selected from hydrogen；
R18Selected from chlorine；
Or the salt of compound shown in general formula I.
In the definition of compound of Formula I given above, collects term used and is generally defined as follows:
Halogen: refer to fluorine, chlorine, bromine or iodine.Alkyl: linear or branched alkyl group, such as methyl, ethyl, propyl, isopropyl, just Butyl or tert-butyl.Naphthenic base: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopenta or cyclohexyl.Substituent group is such as Methyl, halogen etc..Halogenated alkyl: linear or branched alkyl group, the hydrogen atom on these alkyl can be partly or entirely by halogen atom It is replaced, for example, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl etc..Alkyl sulphinyl: Linear or branched alkyl group is connected in structure through sulfinyl (- SO-), such as methylsulfinyl.Alkylsulfinyl: straight Chain or branched alkyl sulfinyl, the hydrogen atom on alkyl can be partly or entirely replaced halogen atom.Halogenated alkyl sulphonyl Base: linear or branched alkyl group sulfonyl, the hydrogen atom on alkyl can be partly or entirely replaced halogen atom.Alkyl amino sulphur Base: such as CH3NHS-、C2H5NHS-.Dialkyl amido sulfenyl: such as (CH3)2NS-、(C2H5)2NS-.Alkyl amino sulfonyl: alkyl- NH-SO2-.Dialkyl amino sulfonyl: (alkyl)2-N-SO2-.Alkylsulfonyl aminocarbonyl: alkyl-SO2-NH-CO-.Alkane Base carbonylamino sulfonyl: alkyl-CO-NH-SO2-.Alkylcarbonylalkyl: alkyl-CO- alkyl-.Alkyl sulphonyl oxygroup: Alkyl-S (O)2-O-.Halogenated alkyl sulfonyl oxygroup: hydrogen atom on the alkyl of alkyl sulphonyl oxygroup can part or all of quilt Replaced halogen atom, such as CF3-SO2-O.Cycloalkyloxycarbonyl: such as cyclopropyl Epoxide carbonyl, cyclohexyloxy carbonyl.Alcoxyl Base: linear or branched alkyl group is keyed in structure through oxygen atom.Halogenated alkoxy: straight or branched alkoxyl, in these alkane Hydrogen atom in oxygroup can be partly or entirely replaced halogen atom.For example, chloromethane epoxide, dichloro methoxyl group, trichloromethoxy, Fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group, trifluoro ethoxy etc..Halo alkoxy carbonyl: alkoxy Hydrogen atom on the alkyl of carbonyl can be partly or entirely replaced halogen atom, such as ClCH2CH2OCO-、 CF3CH2OCO- etc..Alkane Oxygroup alkyl: alkyl-O- alkyl-, such as CH3OCH2-.Halogenated alkoxy alkyl: the hydrogen atom on the alkyl of alkoxyalkyl can Partly or entirely replaced halogen atom, such as ClCH2CH2OCH2-、 CF3CH2OCH2Etc..Alkoxy carbonyl alkyl: alkoxy carbonyl Base-alkyl-, such as CH3OCOCH2-.Halo alkoxy carbonyl alkyl: the hydrogen atom on the alkyl of alkoxy carbonyl alkyl can portion Point or all replaced halogen atom, such as CF3CH2OCOCH2-.Alkyl carbonyl epoxide: such as CH3COO- etc..Halogenated alkyl carbonyl Base oxygroup: the hydrogen atom of alkyl carbonyl epoxide can be partly or entirely replaced halogen atom, such as CF3COO- etc..Alkoxy carbonyl Oxygroup: alkoxy carbonyl-oxygroup-, such as CH3OCOO-.Halo alkoxy carbonyl oxygroup: on the alkyl of alkoxy-carbonyl oxy Hydrogen atom can be partly or entirely replaced halogen atom, such as CF3OCOO-.Alkylthiocarbonyl alkyl: alkylthiocarbonyl-alkane Base-, such as CH3SCOCH2-.Halogenated alkylthio carbonylic alkyl: the hydrogen atom on the alkyl of alkylthiocarbonyl alkyl can part or complete Portion is replaced halogen atom, such as CF3CH2SCOCH2-.Alkyloxy-alkoxy: such as CH3OCH2O- etc..Halogenated alkoxy alkoxy: Hydrogen atom on alkoxy can be partly or entirely replaced halogen atom, such as CF3OCH2O-.Alkoxyalkoxycarbonyl: such as CH3OCH2CH2OCO- etc..Alkylthio group: linear or branched alkyl group is keyed in structure through sulphur atom.Halogenated alkylthio: straight chain Or branched alkylthio, the hydrogen atom on these alkyl can be partly or entirely replaced halogen atom.For example, chloromethane sulfenyl, two Chloromethane sulfenyl, trichloro-methylthio, fluorine methyl mercapto, difluoro methyl mercapto, trifluoromethylthio, chlorine fluorine methyl mercapto etc..Alkylthio alkyl: alkane Base-S- alkyl-, such as CH3SCH2-.Haloalkylthioalkyl: the hydrogen atom on the alkyl of alkylthio alkyl can be part or all of Replaced halogen atom, such as ClCH2CH2SCH2-、 CF3CH2SCH2Etc..Alkyl amino: linear or branched alkyl group, through nitrogen-atoms It is keyed in structure.Haloalkylamino: linear or branched alkyl group amino, the hydrogen atom on these alkyl can part or complete Portion is replaced halogen atom.Dialkyl amido: such as (CH3)2N-, (CH3CH2)2N-.Halogenated dialkyl amido: the hydrogen on alkyl is former Son can be partly or entirely replaced halogen atom, such as (CF3)2N-, (CF3CH2)2N-.Alkenyl: linear chain or branched chain alkenes, such as second Alkenyl, 1- acrylic, 2- acrylic and different cyclobutenyls, pentenyl and hexenyl isomers.Alkenyl further includes polyenoid class, such as 1,2- allene base and 2,4- hexadienyl.Halogenated alkenyl: linear chain or branched chain alkenes, the hydrogen atom on these alkenyls can part Or all replaced halogen atom.Alkenyloxy group: linear chain or branched chain alkenes are keyed in structure through oxygen atom.Haloalkenyloxy: Linear chain or branched chain alkenyloxy group, the hydrogen atom in these alkenyloxy groups can be partly or entirely replaced halogen atom.Enylsulfanyl: straight Chain or branch chain alkene, are keyed in structure through sulphur atom.Such as CH2=CHCH2S-.Allyloxycarbonyl: such as CH2=CHCH2OCO- Deng.Alkynyl: linear chain or branched chain acetylenic, such as acetenyl, 1- propinyl, 2-propynyl and different butynyls, pentynyl and oneself Alkynyl isomers.Alkynyl further includes the group being made of multiple three keys, such as 2,5- adipic alkynyl.Halo alkynyl: linear chain or branched chain Acetylenic, the hydrogen atom on these alkynyls can be partly or entirely replaced halogen atom.Alkynyloxy group: linear chain or branched chain acetylenic, warp Oxygen atom is keyed in structure.Halogenated alkynyloxy group: linear chain or branched chain alkynyloxy group, the hydrogen atom on these alkynyloxy groups can part Or all replaced halogen atom.Alkynyloxycar bonyl: such as CH ≡ CCH2OCO- etc..Alkyl sulphonyl: linear or branched alkyl group warp Sulfonyl (- SO2) be connected in structure, such as methyl sulphonyl.Halogenated alkyl sulfonyl: linear or branched alkyl group sulfonyl, Hydrogen atom on alkyl can be partly or entirely replaced halogen atom.Alkyl-carbonyl: alkyl is connected in structure through carbonyl, such as CH3CO-, CH3CH2CO-.Halogenated alkyl carbonyl: the hydrogen atom on the alkyl of alkyl-carbonyl can partly or entirely be taken by halogen atom Generation, such as CF3CO-.Alkoxy carbonyl: alkoxy is connected in structure through carbonyl.Such as CH3OCO-, CH3CH2OCO-.Amino carbonyl: Such as NH2CO-.Alkyl amino-carbonyl: alkyl-NH-CO-, such as CH3NHCO-, CH3CH2NHCO-.Dialkyl amino carbonyl: such as (CH3)2NCO-, (CH3CH2)2NCO-.(miscellaneous) aryl, (miscellaneous) aryl alkyl, (miscellaneous) aryl carbonyl, (miscellaneous) arylmethyl carbonyl, (miscellaneous) aryl alkyl carbonyl, (miscellaneous) aryloxycarbonyl, the aryl moiety in (miscellaneous) aryl alkyl Epoxide carbonyl include phenyl or naphthalene Base etc..Heteroaryl is containing the heteroatomic five-membered ring of one or more N, O, S or hexatomic ring.Such as furyl, pyrazolyl, thiazolyl, Pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, quinolyl etc..(miscellaneous) aryl: such as phenyl.(miscellaneous) aryl alkyl: such as Benzyl, phenethyl, to chlorophenylmethyl, 2- chloropyridine -5- base, the chloro- thiazole -5- base of 2- etc..(miscellaneous) aryl carbonyl: such as benzoyl Base, 4- chlorobenzene formacyl etc..(miscellaneous) arylmethyl carbonyl: such as PhCH2CO-.(miscellaneous) aryl alkyl carbonyl: such as PhCOCH2-.(miscellaneous) Aryloxycarbonyl: such as phenyloxycarbonyl, 4- cHorophenoxycarbonyl, 4-nitrophenoxy carbonyl, naphthoxycarbonyl.Aryl alkyl Epoxide carbonyl: such as benzyloxycarbonyl, 4- chlorobenzyl Epoxide carbonyl, 4- trifluoromethyl benzyl Epoxide carbonyl.(miscellaneous) aryl alkane Base Epoxide carbonyl: such as PhCH2OCO-、4-Cl-PhCH2OCO- etc..
Table 1, table 2, table 3, table 4, table 5, table 6, table 7, table 8 list R in general formula I respectively1、R2、R3(X=NR3)、R4With R5、R6And R7、R8、R9, W the specific substituent group in part, but they are not limited only to these substituent groups.
Table 1R1Substituent group
Table 2R2Substituent group
R2 R2 R2 R2
H F Cl Br
I CN NO2 NH2
CHO CH3 C2H5 n-C3H7
i-C3H7 n-C4H9 s-C4H9 i-C4H9
t-C4H9 OCH3 OC2H5 OC3H7-n
OC3H7-i OC4H9-n OC4H9-i OC4H9-t
OCH2F OCHF2 OCF3 OCH2CF3
Table 3R3Substituent group
Table 4R4(R5) substituent group
Table 5R6(R7) substituent group
Table 6R8Substituent group
R8 R8 R8 R8
H CN CH3 C2H5
n-C3H7 i-C3H7 n-C4H9 s-C4H9
i-C4H9 t-C4H9 CF3 CCl3
CHF2 CH2F CH2Cl CH2CF3
CF2CF3 COOCH3 Ph Ph-4-Cl
Table 7R9Substituent group
Table 8W substituent group
Part of compounds of the invention can be illustrated with the particular compound listed in 9-table of table 32, but not limited The present invention.In general formula compound I-A, I-B, I-C involved in table, W=R6=R7=R13=R14=R15=R16=R17=H, R9=CH3。
In general formula I-A,
Work as R1=Cl, R2=Cl, R3=R4=R5=H, R8When=H, m=1, (R10)nSubstituent group is shown in Table 9, representation compound Number is followed successively by 9-1-9-279.
Table 9
Table 9-1: in general formula I-A, work as R1=Cl, R2=CH3、R3=R4=R5=H, R8When=H, m=1, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 9-1- 1—9-1-279。
Table 9-2: in general formula I-A, work as R1=Cl, R2=OCH3、R3=R4=R5=H, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 9- 2-1—9-2-279。
Table 9-3: in general formula I-A, work as R1=Cl, R2=CHO, R3=R4=R5=H, R8When=H, m=1, substituent group (R10)nConsistent with substituent group 9 shown in table, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 9- 3-1—9-3-279。
Table 9-4: in general formula I-A, work as R1=Cl, R2=Br, R3=R4=R5=H, R8When=H, m=1, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 9-4- 1—9-4-279。
10: in general formula I-A, working as R1=CH3、R2=Cl, R3=R4=R5=H, R8When=H, m=1, substituent group (R10)nWith Substituent group shown in table 9 is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 10-1- 10-279。
10-1: in general formula I-A, work as R1=CH3、R2=Cl, R3=R4=R5=H, R8=CH3, when m=1, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 10-1- 1—10-1-279。
10-2: in general formula I-A, work as R1=CH3、R2=Cl, R3=R4=R5=H, R8When=H, m=2, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 10-2- 1—10-2-279。
10-3: in general formula I-A, work as R1=CH3、R2=Cl, R3=R4=R5=H, R8=CH3, when m=2, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 10-3- 1—10-3-279。
10-4: in general formula I-A, work as R1=CH3、R2=Cl, R3=R4=H, R5=R8=CH3, when m=1, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 10-4- 1—10-4-279。
11: in general formula I-A, working as R1=C2H5、R2=Cl, R3=R4=R5=H, R8When=H, m=1, substituent group (R10)nWith Substituent group shown in table 9 is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 11-1- 11-279。
11-1: in general formula I-A, work as R1=C2H5、R2=Cl, R3=R4=R5=H, R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 11-1-1—11-1-279。
11-2: in general formula I-A, work as R1=C2H5、R2=Cl, R3=R4=R5=H, R8When=H, m=2, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 11-2- 1—11-2-279。
11-3: in general formula I-A, work as R1=C2H5、R2=Cl, R3=R4=R5=H, R8=CH3, when m=2, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 11-3-1—11-3-279。
11-4: in general formula I-A, work as R1=C2H5、R2=Cl, R3=R4=H, R5=R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 11-4-1—11-4-279。
12: in general formula I-A, working as R1=CHF2、R2=Cl, R3=R4=R5=H, R8When=H, m=1, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 12-1- 12-279。
12-1: in general formula I-A, work as R1=CHF2、R2=Cl, R3=R4=R5=H, R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 12-1-1—12-1-279。
12-2: in general formula I-A, work as R1=CHF2、R2=Cl, R3=R4=R5=H, R8When=H, m=2, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 12-2- 1—12-2-279。
12-3: in general formula I-A, work as R1=CHF2、R2=Cl, R3=R4=R5=H, R8=CH3, when m=2, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 12-3-1—12-3-279。
12-4: in general formula I-A, work as R1=CHF2、R2=Cl, R3=R4=H, R5=R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 12-4-1—12-4-279。
13: in general formula I-A, working as R1=CF3、R2=Cl, R3=R4=R5=H, R8When=H, m=1, substituent group (R10)nWith Substituent group shown in table 9 is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 13-1- 13-279。
14: in general formula I-A, working as R1=Cl, R2=Cl, R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 14-1- 14-279。
15: in general formula I-A, working as R1=CH3、R2=Cl, R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 15-1- 15-279。
16: in general formula I-A, working as R1=C2H5、R2=Cl, R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 16-1—16-279。
17: in general formula I-A, working as R1=CHF2、R2=Cl, R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 17-1—17-279。
18: in general formula I-A, working as R1=CF3、R2=Cl, R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 18-1- 18-279。
In general formula I-B
19: in general formula I-B, working as R3=R4=R5=H, R8When=H, m=1, substituent group (R10)nWith substituent group one shown in table 9 It causes, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 19-1-19-279.
19-1: in general formula I-B, work as R3=R4=R5=H, R8=CH3, when m=1, substituent group (R10)nReplace with shown in table 9 Base is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 19-1-1-19-1-279.
19-2: in general formula I-B, work as R3=R4=R5=H, R8When=H, m=2, substituent group (R10)nWith substituent group shown in table 9 Unanimously, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 19-2-1-19-2-279.
19-3: in general formula I-B, work as R3=R4=R5=H, R8=CH3, when m=2, substituent group (R10)nReplace with shown in table 9 Base is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 19-3-1-19-3-279.
19-4: in general formula I-B, work as R3=R4=H, R5=R8=CH3, when m=1, substituent group (R10)nReplace with shown in table 9 Base is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 19-4-1-19-4-279.
20: in general formula I-B, working as R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)nReplace with shown in table 9 Base is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 20-1-20-279.
In general formula I-C
21: in general formula I-C, working as R3=R4=R5=H, R18=Cl, R8When=H, m=1, substituent group (R10)nWith shown in table 9 Substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 21-1-21-279.
21-1: in general formula I-C, work as R3=R4=R5=H, R18=Cl, R8=CH3, when m=1, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 21-1-1-21- 1-279。
21-2: in general formula I-C, work as R3=R4=R5=H, R18=Cl, R8When=H, m=2, substituent group (R10)nWith 9 institute of table Show that substituent group is consistent, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 21-2-1-21-2- 279。
21-3: in general formula I-C, work as R3=R4=R5=H, R18=Cl, R8=CH3, when m=2, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 21-3-1-21- 3-279。
21-4: in general formula I-C, work as R3=R4=H, R18=Cl, R5=R8=CH3, when m=1, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 21-4-1-21- 4-279。
22: in general formula I-C, working as R3=R4=R5=H, R18=CH3, R8When=H, m=1, substituent group (R10)nWith shown in table 9 Substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 22-1-22-279.
23: in general formula I-C, working as R3=R4=H, R5=CH3, R18=Cl, R8When=H, m=1, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 23-1-23- 279。
24: in general formula I-C, working as R3=R4=H, R5=CH3, R18=CH3, R8When=H, m=1, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 24-1-24- 279。
In general formula I-D
25: in general formula I-D, working as R1=CH3、R2=Cl, R3=R4=R5=H, X=O, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 25-1—25-279。
26: in general formula I-D, working as R1=C2H5、R2=Cl, R3=R4=R5=H, X=O, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 26-1—26-279。
27: in general formula I-D, working as R1=CHF2、R2=Cl, R3=R4=R5=H, X=O, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 27-1—27-279。
28: in general formula I-D, working as R1=CH3、R2=Cl, R3=R4=R5=H, X=S, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 28-1—28-279。
29: in general formula I-D, working as R1=C2H5、R2=Cl, R3=R4=R5=H, X=S, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 29-1—29-279。
30: in general formula I-D, working as R1=CHF2、R2=Cl, R3=R4=R5=H, X=S, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 30-1—30-279。
In general formula I-A, work as R1=CH3、R2=Cl, R4=R5=H, (R10)n=4-CH3, R8When=H, m=1, substituent R3 When hydrogen (not for) is that different substituent groups is shown in Table 31, and representation compound number is followed successively by 31-1-31-140.
Table 31
The salt of part of compounds of the invention can illustrate with the salt for the particular compound listed in table 32, but and unlimited The fixed present invention.
32 part of compounds salt of table
The compounds of this invention is prepared in accordance with the following methods, and reaction equation is as follows, and each group unless otherwise stated defines together in formula Before:
The preparation of compound of Formula I is with the following method:
Reaction obtains compound of Formula I in suitable solvent under alkaline condition by intermediate II and III.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, Sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
React and carried out in suitable solvent, the optional tetrahydrofuran freely of suitable solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile, Toluene, dimethylbenzene, benzene, N,N-dimethylformamide, N-Methyl pyrrolidone, dimethyl sulfoxide, acetone or butanone etc..
Reaction temperature can be in room temperature between solvent boiling point temperature, and usually 20-100 DEG C.
Reaction time is 30 minutes to 20 hours, 1-10 hours usual.
Intermediate II part is commercially available, can also prepare by known method, referring for example to document JP2000007662, US4977264、US6090815、US20040092402、JP09124613、US5468751、US4985426、 US4845097、 Journal of the American Chemical Society(1957),79,1455、Journal of Chemical Society (1955), the method preparation p.3478-3481 described.
Intermediate III is the key intermediate for preparing compound of Formula I of the present invention, is prepared as follows:
Intermediate M1 and dimethyl carbonate at a suitable temperature, react 30 minutes to 20 hours in suitable solvent, Usually 1-10 hours, intermediate M2 is made, this step operation method reference Tetrahedron:Asymmetry, 24 (15-16), 925-936；2013 and Angewandte Chemie, International Edition, 53 (45), 12210-12213； 2014；M3 is made through electrophilic substitution reaction in M2, this step operation method reference Pest Management science, 66 (1), 2010,107-112；M3 is reacted with X1 again is made M4, this step operation method is referring to CN102584705A；Last M4 and corresponding Halide react III be made, this step operation method referring to US20100158860, WO2011133444 and Bioorganic&Medicinal Chemistry,20(20),6109-6122, 2012。
Although certain compounds disclosed in compound of Formula I and the prior art of the invention also belong to substituted pyrazolecarboxylic class Object is closed, but there are still dramatically different for structure feature.And due to the difference in these structures the compound of the present invention is had There is better pesticide and miticide actility.
Compound of Formula I shows excellent activity, therefore, this hair to the various pests harmful mite in agricultural or other field Bright technical solution includes that compound of Formula I is used as the purposes for preparing insecticidal/acaricidal agent in agricultural or other field.
Compound shown in general formula I can be used for preventing and treating following pest harmful mite:
Coleoptera (Coleoptera) (beetle): bean weevil belongs to kind of (Acanthoscelides spp.) (curculionid), acanthoscelides obtectus (Acanthoscelides obtectus) (common pea weevil), Emerald ash borer (Agrilus planipennis) (Fraxinus rhynchophylla It is narrow Ji fourth), acupuncture needle Eimeria kind (Agriotes spp.) (wireworm), anoplophora glabripennis (Anoplophora Glabripennis) (Asia psacotheahilaris), Anthonomusgrandis belong to kind of (Anthonomus spp.) (Culculionidae), Mexican anthonomusgrandis (Anthonomus grandis) (bollworm), cocoon bee belong to kind of (an Aphidius spp.), weevil belong to kind of (an Apion spp.) (as Worm), sugarcane cockchafer belong to kind of (Apogonia spp.) (grub), black suede cockchafer (Atacnius sprctulus) (black suede cockchafer Son), Atomaria linearis (Atomaria linearis) (small beet beetle (pygmy mangold beetle), cucumber beetle belong to kind (Aulacophore spp.), beet belong to kind as (Bothynoderes punctiventris) (beet root curculionid), bean weevil (Bruchus spp.) (curculionid), pea weevil (Bruchus pisorum) (pea weevil), Cacoesia belong to kind an of (Cacoesia Spp.), Callosobruchus maculatus (Callosobruchus maculatus) (southern cowpea curculionid), pineapple bug (Carpophilus Hemipteras) (dried-frait beetle), beet tortoise beetle (Cassida vittata), day Bos kind (Ccrostcrna spp.), Ccrotoma belongs to kind of (Ccrotoma spp.) (chrysomonad (chrysomcids)), chrysomelid (the Cerotoma trifur of beans Cata) (the chrysomelid worm of beans), ceutorhynchus kind (Ceutorhynchus spp.) (curculionid), Chinese cabbage seed tortoise are as (Ceutorhynchus Assimilis) (Chinese cabbage weevil (cabbage seedpod weevil)), turnip tortoise are as (Ceutorhynchus napi) (cabbage curculionid (cabbage curculio)), phyllotreta kind (Chaetocnema spp.) (chrysomonad), Colaspis belong to Kind (Colaspis spp.) (native beetle), Conoderus scalaris, Conoderus stigmosus, Li Xiang (Conotrachelus nenuphar) (plum bores weevil), Cotinus nitidis (Green june beetle (Green June Beetle)), asparagus scotellaris (Crioceris asparagi) (asparagus beetle), rusty grain beetle (Cryptolestes ferrugincus) (rust paddy beetle (rusty grainbeetle)), Cryptolestes pusillus (Cryptolestes pusillus) (flat ostomatid), Cryptolestes turcicus Grouville (Cryptolestes turcicus) (Turkey paddy Beetle (Turkish grain beetle)), Ctenicera belong to kind of (Ctenicera spp.) (nematode), Curculio kind (Curculio spp.) (curculionid), round end rhinoceros cockchafer belong to kind of (Cyclocephala spp.) (grub), close withe as (Cylindrocpturus adspersus) (sunflower grass curculionid (sunflower stem weevil)), mango leaf-cutting as (Deporaus marginatus) (mango leaf-cutting curculionid (mango leaf-cutting weevil)), lader beetle are stupid It is (Dermestes lardarius) (lader beetle is stupid), white abdomen skin stupid (Dermestes maculates) (white abdomen skin is stupid), chrysomelid Belong to kind of (Diabrotica spp.) (chrysomelid), mexican bean ladybird (Epilachna varivcstis) (Mexico beans beetle), Eat into stem weevil (raustinus cubae), pale rootstock as (Hylobius pales) (pales weevil (pales weevil)), Phytonomus kind (Hypera spp.) (curculionid), alfalfa leaf as (Hypera postica) (alfalfa weevil), It is small stupid that Hyperdoes belongs to kind (Hyperdoes spp.) (an Argentinian stem weevil (Hyperodes weevil)), coffee berry The small stupid category kind (Ips spp.) (spine shin is small stupid (engravers)) of (Hypothenemus hampei) (coffee berry beetle), tooth, Lasioderma serricorne (Lasioderma serricorne) (cigarette beetle), colorado potato bug (Leptinotarsa Decemlineata) (Colorado potato beetle), Liogenys fuscus, Liogenys suturalis, rice water weevil (Lissorhoptrus oryzophilus) (rice water weevil), powder stupid category kind (Lyctus spp.) (the stupid stupid beetle of moth/powder of wood (powder post beetles)), Maecolaspis joliveti, Megascelis belong to kind of (a Megascelis spp.), Corn click beetle (Melanotus communis), nitidulid belong to kind of (a Meligethes spp.), rape nitidulid (Meligethes aeneus) (brevitarsis (blossom beetle)), May beetle (Melolontha melolontha) (typical European chafer), Oberea brevis, linear cylinder longicorn (Oberea linearis), coconut palm eat into rhinoceros cockchafer (Oryctes Rhinoceros) (date palm beetle (date palm beetle)), (city trade saw-toothed grain beetle (Oryzaephilus mercator) Saw-toothed grain beetle (merchant grain beetle)), saw-toothed grain beetle (Oryzaephilus surinamensis) (sawtooth paddy first Worm (sawtoothcd grain bcctlc)), beak weevil belong to kind of (Otiorhynchus spp.) (curculionid), black angle scotellaris (Oulema melanopus) (cereal leaf beetle (cereal leafbeetle)), Oulema oryzae (Oulema oryzae), The short beak of rose is as belonging to kind of (Pantomorus spp.) (curculionid), food phyllobranchia cockchafer belong to kind of (a Phyllophaga spp.) (May/ June chafer), Phvllophaga cuyabana, striped flea beetle kind (Phyllotreta spp.) (chrysomonad), apple tiger It is stupid as belonging to kind (a Phynchites spp.), Japan popillia flavosellata fairmaire (Popillia japonica) (Japanese beetle), large space between muscles (Prostephanus truncates) (large space between muscles is long stupid (larger grain borer)), the stupid (Rhizopertha of paddy Dominica) (the small moth of paddy (lesser grain borer)), root gill cockchafer belong to kind of (a Rhizotrogus spp.) (Europe gold Tortoise (Eurpoean chafer)), Rhynchophorus kind (Rhynchophorus spp.) (curculionid), small stupid category kind (Scolytus spp.) (wood stupid moth), Shenophorus belong to kind of (Shenophorus spp.) (grain weevil), pea leaf as (Sitona lincatus) (pealeaf weevil (pca leaf weevil)), Sitophilus kind (Sitophilus spp.) (grain weevil First), grain weevil (Sitophilus granaries) (paddy worm (granary weevil)), rice weevil (Sitophilus oryzae) (rice weevil first (rice weevil)), medicinal material ostomatid (Stegobium paniceum) (Stegobium paniceum (drugstore beetle)), Tribolium kind (Tribolium spp.) (flour beetle), red flour beetle (Tribolium castaneum) (red flour beetle (red Flour beetle)), miscellaneous quasi- paddy moisten (Tribolium confusum) (confused flour beetle (confused flour beetle)), Piebald skin stupid (Trogoderma variabile) (warehouse skin is stupid (warehouse beetle)) and Zabrus tenebioides。
Dermaptera (Dcrmaptcra) (earwig).
Neuroptera (Dictyoptera) (cockroach): Groton bug (Blattella germanica) (Groton bug (German cockroach)), oriental cockroach (Blatta orientalis) (oriental cockoach), Pennsylvania wood Lian (Parcoblatta pennylvanica), American cockroach (Periplaneta americana) (America roach consumptive disease (American Cockroach)), Australian cockroach (Periplaneta australoasiae) (Australian cockroach (Australian Cockroach)), periplaneta brunnea (Pcriplancta brunnca) (periplaneta brunnea (brown cockroach)), smoke Perilpaneta americana (Periplaneta fuliginosa) (Peroplaneta fluligginosa (smokybrown cockroach)), the green blattaria (Pyncoselus of sugarcane Suninamensis) (sugarcane Lian (Surinam cockroach)) and long hair blattaria (Supella longipalpa) (brown band roach Lian (brownbanded cockroach)).
Diptera (Diptera) (fly): the latent fly (Agromyza of Aedes kind (Aedes spp.) (mosquito), alfalfa Frontella) ((Agromyza spp.) is (latent for (alfalfa dives fly (alfalfa blotch leafminer)), Hippelates kind Leaf fly), (add by trypetid (Anastrepha suspensa) by Anastrepha kind (Anastrepha spp.) (drosophila), Caribbean It strangles than by trypetid (Caribbean fruit fly)), Anopheles kind (Anopheles spp.) (mosquito), Bactrocera kind (Batrocera spp.) (drosophila), melonfly (Bactrocera cucurbitae) (melon fly), citrus fruit fly (Bactrocera dorsalis) (oriental fruit fly), small Anastrepha kind (Ceratitis spp.) (drosophila), the small item in Mediterranean are real Fly (Ceratitis capitata) (medfly), Chrysops kind (Chrysops spp.) (deer horsefly), Callitroga's kind (Cochliomyia spp.) (screw worm fly larva), Ying uranotaenia kind (Contarinia spp.) (Ying mosquito), Culex kind (Culex Spp.) (mosquito), Ye Ying uranotaenia kind (Dasineura spp.) (Ying mosquito), You Cai Ye Ying mosquito (Dasineura brassicae) (volume Xin Cai Ying mosquito), Delia kind (Delia spp.), delia platura (Delia platura) (root maggot (seedcorn Maggot)), Drosophila kind (Drosophila spp.) (vinegar fly), Fannia kind (Fannia spp.) (housefly), anthomyia canicularis (Fannia canicularis) (Fannia canicularis (little house fly)), anthomyia scalaris (Fannia scalaris) (grey abdomen Latrine fly), big horse botfly (Gasterophilus intestinalis) (horse botfly), Gracillia perseae, Haematobia irritans (Haematobia irritans) (horn fly), Hylemyia kind (Hylemyia spp.) (root maggot (root maggot)), heel fly (Hypoderma lineatum) (common heel fly (common cattle grub)), Liriomyza kind (Liriomyza Spp.) (Liriomyza), wild cabbage liriomyza bryoniae (Liriomyza brassica) (snake Liriomyza (serpentine Leafminer)), sheep hippoboscid (Melophagus ovinus) (sheepked), fly belong to kind of (Musca spp.) (housefly (muscid fly)), face fly (Musca autumnalis) (face fly (face fly)), housefly (Vusca Domestica) (housefly (house fly)), Oestrus ovis (Oestrus ovis) (sheep nose fly (sheep bot fly)), Europe Frit fly (Oscinella frit) (Oscinella frit), beet spring fly (Pegomyia betae) (spinach leaf miner (beet Leafminer)), wheat fly belongs to kind of (a Phorbia spp.), carrot fly (Psila rosae) (carrot rust fly (carrotrust fly)), cherry fruit fly (Rhagoletis cerasi) (cherry fruit fly (cherry fruit fly)), apple Fruit fly (Rhagoletis pomonella) (apple maggots (apple maggot)), wheat midge (Sitodiplosis Mosellana) (orange wheat flower mosquito (orange wheat blossom midge)), tatukira (stomoxys Calcitruns) (tatukira (stable fly)), the gadfly belong to kind of (Tahanus spp.) (horse botfly) and big uranotaenia kind (Tipula Spp.) (daddy-longlegs).
Semiptera (Hemiptera) (stinkbug): quasi- acrosternumhilare (Acrosternum hilare) (acrosternumhilare (green stink Bug)), america valley cinchbug (Blissus leucopterus) (chinch bug (chinch bug)), potato person of outstanding talent fleahopper (Calocoris norvegicus) (potato fleahopper (potato mirid)), cimex hemipterus (Cimex hemipterus) (cimex hemipterus (tropical bed bug)), bedbug (Cimex lectularius) (bedbug (bed hug)), Daghertus The black wing red stinkbug of fasciatus, Dichelops furcatus, cotton (Dysdercus suturellus) (red cotton bug (cotton Stainer)), Edessa meditabunda, Europe Eurygasterspp (Eurygaster maura) (paddy worm (cereal bug)), Euschistus heros, brown smelly stinkbug (Euschistus servus) (brown stinkbug (brown stink bug)), iS-One angle fleahopper (Helopeltis antonii), tea angle fleahopper (Helopeltis theivora) (tea blight plantbug), stinkbug category Kind (Lagynotomus spp.) (stinkbug), big Leptocorisa spp (Leptocorisa oratorius), different Leptocorisa spp (Leptocorisa varicornis), Lygus Hahn kind (Lygus spp.) (fleahopper (plant bug)), lygushesperus (Lygus hesperus) (western tarnished plant bug), the graceful powder stinkbug (Maconellicoccus of the rose of Sharon Hirsutus), Neurocolpus longirostris, green rice bug (Nezara viridula) (southern green Stink bug), Phytocoris kind (PhyLocoris spp.) (fleahopper), California plant fleahopper (Phytocoris Californicus), Phytocoris relativus, Piezodorus guildingi, four line fleahoppers (Poecilocapsus lineatus)(fourlined plant bug)、Psallus vaccinicola、Pseudacysta Perseae, Scaptocoris castanea and Triatoma kind (Triatoma spp.) (suck blood and bore nose worm (bloodsuckingconenose bug)/hunt stinkbug (kissing bug)).
Homoptera (Homoptera) (aphid, a red-spotted lizard, aleyrodid, leafhopper): acyrthosiphum pisim (Acrythosiphonpisum) (pea Aphid (pea aphid)), adelgid kind (Adelges spp.) (adelgids), wild cabbage aleyrodid (Aleurodes Proletella) (cabbage aleyrodid), Aleurodicus dispersus (Aleurodicus disperses), velvet aleyrodid (Aleurothrixus flccosus) (whitefly in bt cotton (woolly whitefly)), white wheel armored scale belong to kind an of (Aluacaspis Spp.), Amrasca bigutella bigutella, froghopper belong to kind of (Aphrophora spp.) (leafhopper (leafhopper)), California red scale (Aonidiella aurantii) (California red a red-spotted lizard (California red Scale)), Aphis kind (Aphis spp.) (aphid), cotten aphid (Aphis gossypii) (cotton aphid), apple aphid (Aphis pomi) (apple aphid), eggplant are without net aphid (Aulacorthitm solani) (digitalis aphid (foxglove Aphid)), Aleyrodes kind (Bemisia spp.) (aleyrodid), Bemisia argentifolii (Bemisia argentifolii), sweet potato whitefly (Bemisia tabaci) (sweetpotato whitefly), Diuraphis noxia (Brachycolus noxius) (Russian aphid (Russian aphid)), asparagus tubule aphid (Brachycorynclia asparagi) (asparagus aphid (asparagus Aphid)), Brevennia rehi, brevicoryne brassicae (Brevicoryne brassicae) (cabbage aphid), lecanium belong to kind (Ceroplastes spp.) (a red-spotted lizard), ceroplastes rubens (Ceroplastes rubens) (red wax scale), snow armored scale belong to kind (Chionaspis spp.) (a red-spotted lizard), Aspidiotus belong to kind of (Chrysomphalus spp.) (a red-spotted lizard), soft wax a red-spotted lizard belongs to kind an of (Coccus Spp.) (a red-spotted lizard), the pink bad aphid (Dysaphis plantaginea) (rosy apple aphid) of apple, green jassids belong to kind (Empoasca spp.) (leafhopper) apple aphid (Eriosoma lanigerum) (woolly apple aphid), blows cotton a red-spotted lizard (Icerya purchasi) (cottony cushion scale), mango yellow line leafhopper (Idioscopus nitidulus) (mango leafhopper), small brown rice planthopper (Laodelphax striatellus) (smaller brown planthopper), Lepidosaphes shimer kind (Lepidosaphes spp.), long tube Aphis kind (Macrosiphum spp.), root of Beijing euphorbia Macrosiphus spp (Macrosiphum euphorbiae) (potato aphid (potato aphid)), grain aphid (Macrosiphum Granarium) (Britain's wheat aphid (English grain aphid)), rose aphid (Macrosiphum rosae) (rose Aphid (rose aphid)), four line leafhopper (Macrosteles quadrilineatus) (Aster tataricus leafhopper (aster Leafhopper)), Mahanarva frimbiolata, Acyrthosiphon dirhodum (Metopolophium dirhodum) (rose Wheat aphid (rose grain aphid)), Midis longicornis, black peach aphid (Myzus persicae) (black peach aphid (green Peach aphid)), rice green leafhopper belong to kind of (Nephotettix spp.) (leafhopper), rice green leafhopper (Nephotettix Cinctipes) (greenery cicada (green leafhopper)), brown paddy plant hopper (Nilaparvata lugens) (brown Planthopper), chaff piece armored scale (Parlatoria pergandii) (chaff scale), ebony armored scale (Parlatoria Ziziphi) (ebony scale), popcorn wing plant hopper (Peregrinus maidis) (corn delphacid), froghopper category Kind (Philaenus spp.) (spittle insects), grape phylloxera (Phylloxera vitifoliae) (grape Phylloxera), Physokermes piceae (Physokermes piceae) (spruce bud scale), stern line mealybug belong to kind (Planococcus spp.) (mealybug), mealybug belong to kind of (Pseudococcus spp.) (mealybug), the clean mealybug of pineapple (Pscudococcus brcvipcs) (pinc apple mcalybug), theatre armored scale (Quadraspidiotus Perniciosus) (san jose scale (San Jose scale)), aphid a red-spotted lizard belong to kind of (Rhapalosiphum spp.) (aphid), jade Rice tree louse (Rhapalosiphum maida) (corn leaf aphids (corn leaf aphid)), rhopalosiphum padi (Rhapalosiphum Padi) (oatbird-cherry aphid), pearl lecanium belong to kind of (Saissetia spp.) (a red-spotted lizard), olive pearl lecanium (Saissetia Oleae) (black a red-spotted lizard), green bugs (Schizaphis graminum) (green bugs (gr eenbug)), grain aphid (Sitobion avenge) (Britain's wheat aphid), white backed planthopper (Sogatella furcifera) (white-backed Planthopper), variegation Aphis kind (Therioaphis spp.) (aphid), line lecanium belong to kind of (a Toumeyella spp.) (a red-spotted lizard), sound Aphis kind (Toxoptera spp.) (aphid), white powder Pediculus kind (Trialeurodes spp.) (aleyrodid), greenhouse Trialeurodes vaporariorum (Trialeurodes vaporariorum) (greenhouse whitefly (greenhouse whitefly)), knot wing trialeurodes vaporariorum (Trialeurodes abutiloneus) (bandedwing whitefly), sharp armored scale category kind (Unaspis spp.) (a red-spotted lizard), Swear sharp clam (Unaspis yanonensis) (arrow a red-spotted lizard (arrowhead scale)) and Zulia entreriana.
Hymenoptera (Hymenoptera) (ant, wasp and honeybee): Myrmecina kind (Acromyrrmex spp.), new Boundary cabbage sawfly (Athalia rosae), leaf ant belong to kind of (Atta spp.) (an Ieafcutting ants), black ant belongs to kind (Camponotus spp.) (carpented ant (carpenter ant)), Diprion kind (Diprion spp.) (sawfly (sawfly)), ant belongs to kind of (Formica spp.) (ant), Argentine ant (Iridomyrmex humilis) (Argentineant), Monomorium subspecies (Monomorium ssp.), MonomoriumMayr (Monomorium minumum) (little Black ant), kitchen ant (Monomorium pharaonis) (little red ant (Pharaoh ant)), Neodiprion kind (Neodiprion spp.) (sawfly), Pogonomyrmex kind (Pogonomyrmex spp.) (harvester ant), hornet belong to kind (Polistes spp.) (wasp (paper wasp)), Solenopsis kind (Solenopsis spp.) (fiery ant), odorous antenna (Tapoinoma sessile) (odorous antenna (odorous house ant)), Tetramorium kind (Tetranomorium spp.) (Pavement Ant (pavement ant)), Vespula kind (Vespula spp.) (yellow jacket (yellow jacket)) and carpenter bee Belong to kind of (Xylocopa spp.) (carpenter bee (a carpenter bee)).
Isoptera (Isoptera) (termite): formosanes belong to kind of (a Coptotcrmcs spp.), bent jaw termite (Coptotermes curvignathus), French termite (Coptotermes frenchii), coptotermes formosanus (Coptotermes Formosanus) (Formosan subterranean termite), angle Cryptotermes kind (Cornitermes spp.) (proboscis Termite (nasute termite)), sand Cryptotermes kind (Cryptotermes spp.) (dry-wood termite), different Cryptotermes kind (Heterotermes spp.) (desert Soil termites (desert subterranean termite)), golden yellow different termite ((IIeterotermes aureus), kalotermitid belong to kind of (Kalotermes spp.) (dry-wood termite), principal columns of a hall Cryptotermes kind (Incistitermes spp.) (dry-wood termite), Macrotermes kind (Macrotermes spp.) (cultivation termite (fungus Growing termite)), edge kalotermitid belong to kind ((Marginitermes spp.) (dry-wood termite), saw a Cryptotermes kind (Microcerotermes spp.) (careless termite (harvester termite)), the small termite (Microtermes of rice and kernel Obesi), former angle Cryptotermes kind (Procornitermes spp.), Reticulitermes kind (Reticulitermes spp.) (dwell by soil Termite), Reticulitermes banyulensis, meadow reticulitermes flavipe (Reticulitermes grassei), yellow limb dissipate it is white Ant (Reticulitermes flavipes) (east Soil termites), beauty little Huang reticulitermes flavipe (Reticulitermes Hageni), west reticulitermes flavipe (Reticulitermes hesperus) (west Soil termites), Sang Te reticulitermes flavipe (Reticulitermes santonensis), the northern reticulitermes flavipe that dwells (Reticulitermes speratus), the black shin of U.S. dissipate white Ant (Reticulitermes tibialis), the small black reticulitermes flavipe (Reticulitermes virginicus) of U.S., proboscis dissipate white Ant belongs to kind of (Schedorhinotermes spp.) and ancient Cryptotermes kind (Zootermopsis spp.) (rotten wood termite).
Lepidoptera (Lepidoptera) (moth and butterfly): Achoea janata, Adoxophyessp kind (Adoxophyes Spp.), adoxophyes moth (Adoxophyes orana), tiger belong to kind of (Agrotis spp.) (cutworm), small cutworm ((Agrotis ipsilon) (black cutworm), cotton leaf ripple noctuid (Alabama argillacea) (cotton leafworm (cotton leafworm))、Amorbia cuneana,Amyelosis transitella(navel orangeworm)、 Anacamptodes defectaria, sliver gelechiid (Anarsia lineatella) (peach twig borer), jute Bridge night high (Anomis sabulijera) (jute looper), Anticarsia (Anticarsia gemmatalis) (velvetbean caterpillar), fruittree leafroller (Archips argyrospila) (fruit tree Leafroller), rose leaf roller (Archips rosana) (rose leaf roller), volume moth belong to kind an of (Ar Gyrotaenia spp.) (tortricid moths), tangerine Argyrotaenia spp (Argyrotaenia citrana) (citrus leaf-roller (orange tortrix)), Autographa gamma, Bonagota cranaodcs, rice leaf roller (Borbo Cinnara) (rice leaf folder), cotton leaf lyonetid (Bucculatrix thurberiella) (cotton Leafperforator), thin moth belongs to kind of (Caloptilia spp.) (leaf miner), Capua reticulana, peach fruit moth (Carposina niponensis) (peach fruit moth (peach fruit moth)), straw borer spp kind (Chilo spp.), mango Chlumetia transversa (Chlumetia transversa) (mango shoot borer), rose Choristoneura spp (Choristoneura Rosaceana) (oblique banded leaf roller), Noctua kind (Chrysodeixis spp.), cnaphalocrocis are wild Snout moth's larva (Cnaphalocerus medinalis) (meadow leaf roller (grass leafroller)), beans Pier kind (Colias Spp.), lichee litchi (Conpomorpha cramerella), the stupid moth (Cossus cossus) of fragrance wood (the stupid moth of wood), Crambus Fabricius kind (Crambus spp.) (Sod webworms), Lee's Grapholita spp (Cydia funebrana) (Li Guoe (plum Fruit moth)), oriental fruit months (Cydia molesta) (east heart-eating worm (oriental fruit moth)), pea Eat into pod high (Cydia nignicana) (pea moth), the stupid moth of apple (Cydia pomonella) (codling moth (codling moth)), Darna diducta, Diaphania kind (Diaphania spp.) (stem borer (stem borer)), Snout moth's larva belongs to kind of (Diatr aea spp.) (stem borer (a stalk bor er)), small sugarcane borer (Diatraea saccharalis) (sugarcane borer), Diatraea grandiosella (Diatraea graniosella) (southwester corn Borer), Earias kind (Earias spp.) (bollworm), earias insulana (Earias insulata) (Egyptian Bollworm), earias fabia (Earias vit.ella) (rough northern bollworm), Ecdytopopha Aurantianum, South America maize seedling phycitid (Elasmopalpus lignosellus) (lesser cornstalk borer), Shallow brown apple moth (Epiphysias postruttana) (light brown apple moth), meal moth belong to kind (Ephestia spp.) (powder snout moth's larva), meal moth (Ephestia cautella) (almond moth), tobacco powder sp (Ephestia elutella) (tobacco snout moth's larva (tobbaco moth)), Mediterranean flour moth (Ephestia kuehniella) (Mediterranean flour moth), Epimeces belong to kind of (an Epimeces spp.), night steinernema (Epinotia Aporema), Erionota thorax (Linne) (Erionota thrax) (banana skipper), ligustrum fine tortricidae (Eupoecilia Ambiguella) (grape berry moth (grape berry moth)), original cutworm (Euxoa auxiliaris) (army Cutworm), Agrotis kind (Feltia spp.) (cutworm), angle sword Noctua kind (Gortyna spp.) (stem borer), Fruit moth (Grapholita molesta) (peach (apricot) sub- heart-eating worm (oriental fruit moth)), treble cut snout moth are eaten into east (Hedylepta indicata) (bean pyralid (bean leaf webber)), green Eimeria kind (Helicoverpa spp.) (noctuid), bollworm (Helicoverpa armigera) (cotton bollworm), paddy reality noctuid (Helicoverpa Zea) (corn borer ridge (snout moth's larva ridge worm/bollworm)), Heliothis kind (Heliothis spp.) (noctuid), tobacco budworm (Heliothis virescens) (tobacco budworm), Hellula undalis (Hellula undalis) (cabbage Webworm), Indarbela belongs to kind of (Indarbela spp.) (a root moth), the stupid moth (Keiferia of tomato Lycopersicella) (tomato pinworm), the white wing open country snout moth's larva of eggplant (Leucinodes orbonalis) (eggplant Fruit borer), pear leaf blister moth (Leucoptera malifoliella), thin moth belong to kind of (a Lithocollectis spp.), Grape olethreutid (Lobesia botrana) (grape fruit moth), Loxagrotis belong to kind an of (Loxagrotis Spp.) (noctuid), beans white line cutworm (Loxagrotis albicosta) (western bean cutworm), gypsymoth (Lymantria dispar) (gypsy moth), apple leaf miner (Lyonetiaclerkella) (apple leaf miner (apple Leafminer)), oil palm bag moth (Mahasena corbetti) (oil palm bagworm), Malacosoma kind (Malacosoma spp.) (tent caterpillars), lopper worm (Mamestra brassicae) (dish march moth (cabbage armyworm)), beanpod open country snout moth's larva (Maruca testulalis) (beans open country snout moth's larva), bag moth (Metisa plana) (knot Grass-and-insect painting), Mythimna unipuncta (true armyworm), Neoleucinodes elegantalis (small tomato moth (small tomato borer)), 3 water snout moth's larva (Nymphula depunctalis) (rice leaf roller (rice Caseworm)), winter looper (Operophthera brumata) (winter moth), European corn borer (Ostrinia Nubilalis) (European corn borer (European corn borer)), Oxydia vesulia, the brown volume moth (Pandemis of boundary Cerasana) (common glucose leaf roller (common currant tortrix)), apple brown bortrix (Pandemis heparana) (brown apple tortrix), African Bodhidharma swallowtail butterfly (Papilio demodocus), Pectinophora gossypiella (Pectinophora Gossypiella) (pink bollworm (pink bollworm)), boundary Noctua kind (Peridroma spp.) (cutworm), variegated Tiger (Peridroma saucia) (variegated cutworm), coffee leafminer (Perileucoptera Coffeella) (white coffee leafminer), phthorimaea operculella (Phthorimaea operculella) (potato tuber moth), citrus leaf lyonetid (Phyllocnisitis citrella), thin moth belong to kind (Phyllonorycter spp.) (leaf miner), cabbage butterfly (Pieris rapae) (external cabbage caterpillar (imported Cabbageworm)), head is by green noctuid (Plathypena scabra), India paddy spot moth (Plodia interpunctella) (Indian meal moth), diamond-back moth (Plutella xylostella) (diamondback moth), grape berry moth (Polychrosis viteana) (grape berry moth), tangerine fruit ermine moth (Prays endocarps), olive ermine moth (Prsys oleae) (olive moth), mythimna separata belong to kind of (Pseudaletia spp.) (noctuid), Pseudaletia Unipunctata (armyworm), soybean noctuid (Pseudoplusia includens) (soybean looper), looper (Rachiplusia nu), yellow rice borer (Scirpophaga incertulas), moth stem night high category kind (Sesamia spp.) (moth Stem worm), Sesamia inferens (Sesamia inferens) (pink rice stemborer), powder stems moth (Sesamia Nonagrioides), the brown slug moth of copper stain (Setora nitens), gelechiid (Sitotroga cerealella) (Angoumois Grain moth), pilleriana (Sparganothis pilleriana), Spodoptera kind (Spodoptera Spp.) night is coveted on (armyworm), beet armyworm (Spodoptera exigua) (beet armyworm (beet armyworm)), meadow Moth (Spodoptcra fugipcrda) (autumn armyworm (fall armyworm)), southern spodoptera (Spodoptera Oridania) (southern armyworm (southern armyworm)), emerging Noctua kind (Synanthedon spp.) (root moth Worm), Thecla basilides, Thermisia gemmatalis, casemaking clothes moth (Tineola bisselliella) (webbing Clothes moth), cabbage looper (Trichoplusia ni) (cabbage looper), Liriomyza brponiae (Tuts Absoluta), Yponomeuta kind (Yponomeuta spp.), the stupid moth of coffee leopard (Zeuzeracoffeae) (red branch ) and Zeuzera pyrina (the stupid moth of pears leopard (leopard moth)) borer.
Mallophaga ((Mallophaga) poultry louse (chewing lice)): sheep poultry louse (Bovicola ovis) (sheep Biting louse), fire menopon gallinae (Menacanthus stramineus) (chick poultry louse (chicken body )) and shaft louse (Menopon gallinea) (common henhouse (common hen house)) louse.
Orthoptera (Orthoptera) (grasshopper, locust and cricket): blackspot arna Zhong (Anabrus simplex) (Mo Men Katydid (Mormon cricket)), mole cricket (Gryllotalpidae) (mole cricket (mole cricket)), Asiatic migrotory locust (Locusta migratoria), grasshopper belong to kind of (Melanoplus spp.) (grasshopper), guiding principle wing spinelet Zhong (Microcentrum Retinerve) (angle wing katydid (angular winged katydid)), Pterophylla belong to kind an of (Pterophylla Spp.) (katydid), chistocerca gregaria, fork-tail katydid (Scudderia furcata) (fork-tail shrubbery tree Zhong (fork tailed bush katydid)) and black angle oncus locust (Valanga nigricorni).
Anoplura (Phthiraptera) (sucks lice (sucking louse)): Pediculus of sucking blood kind (Haematopinus Spp.) (ox louse and pig lice), sheep jaw lice (Linognathus ovillus) (sheep lice (sheep louse)), head louse (Pediculus humanus capitis) (body louse), pediculus humanus corporis (Pediculus humanus humanus) (body louse) and yin Lice (Pthirus pubis) (crab louse (crab louse)).
Siphonaptera (Siphonaptera) (flea): ctenocephalides canis (Ctenocephal ides canis) (dog flea), Ctenocephalides felis (Ctenocephalides felis) (cat flea) and Pulex irritans (Pulex irritans) (human flea).
Thysanoptera (thrips): cigarette brown thrip (Frankliniella fusca) (tobacco thrip), western classical architecture (Frankliniella occidentalis) (western flower thrips), Frankliniella shultzei, prestige Lian Si flower thrips (Frankliniella williamsi) (corn thrips (corn thrip)), greenhouse thrips (IIeliothrips haemorrhaidalis)(greenhouse thrip)、 Riphiphorothrips Cruentatus, hard Thrips kind (Scirtothrips spp), campanulaceae thrips (Scirtothrips cirri) (citrus Thrip), Scirothrips dorsalis (Scirtothrips dorsalis) (yellow tea thrips), Taeniothrips Rhopalantennalis and Thrips kind (Thrips spp.).
Thysanoptera (Thysanura) (moth (bristletail)): silverfish belongs to kind of (Lepisma spp.) (stupid worm (silverfish)) and special mess silverfish belongs to kind of (Thermobia spp.) (a special mess fish).
Acarina (Acarina) (mite (mite) and cicada (tick)): Wu Shi bee shield mite (Acarapsis woodi) (honeybee gas Pipe endoparasitism mite (tracheal mite of honeybee)), Tyroglyphus kind (Acarus spp.) (food mites), thick foot powder Mite (Acarus siro) (paddy mite (grain mite)), mango bud mite (Aceria mangiferae) (mango bud Mite), peronium Eriophyes kind (Aculops spp.), Aculops lycopersici (Aculops lycopersici) (tomato Russet mite), Aculops pelekasi, tangerine peronium goitre mite (Aculus pelekassi), Si Shi pierce goitre mite (Aculus Schlechtendali) (apple pierces goitre mite (apple rust mite)), lone star tick (Amblyomma amcricanum) (lone star tick), Boophilus kind (Boophilus spp.) (tick), oval short hairs tick (Brevipalpus Obovatus) (privet mite), purplish red short hairs mite (Brevipalpus phoenicis) (red and black flat Mite), rouge tick belongs to kind of (Demodex spp.) (a mange mites), Dermacentor kind (Dermacentorspp.) (hard tick), beauty Continent dog tick (Dermacentor variabilis) (american dog tick), dermatophagoides pteronyssinus (Dermatophagoides Pteronyssinus) (house dust mite), Eotetranychus kind (Eotetranycus spp.), Eotetranychus carpini (Eotetranychus carpini) (yellow spider mite (yellow spider mite)), Epitrimerus kind (Epitimerus Spp.), Eriophyes kind (Eriophyes spp.), Isodesspp kind (work；Odes spp.) (tick), Panonychus citri category kind ((Metatetranycus spp.), notoedres cati (Notoedres cati), Oligonychus kind (Oligonychus spp.), coffee Coffee unguiculus mite (Oligonychus coffee), ilex Oligonychus (Oligonychus ilicus) (southernred mi Te), Panonychus citri belongs to kind of (a Panonychus spp.), Jie-Li enzyme-SQ (Panonychus cirri) (orange spider (citrus Red mite)), panonychus ulmi (Panonychus ulmi) (European red spider (European red mite)), tangerine wrinkle leaf Pierce goitre (Phyllocoptruta oleivora) (citrus rust mite), Polyphagotarsonemus latus Banks (Polyphagotarsonemun latus) (broad mite (broad mite)), brown dog tick (Rhipicephalus Sanguineus) (brown dog tick (brown dog tick)), root mite belong to kind of (Rhizoglyphus spp.) (root mite (bulb Mite)), itch mite (Sarcoptes scabiei) (itch mite), avocado apical cap goitre mite (Tegolophus Perseaflorae), Tetranychus kind (Tetranychus spp.), (2 points of T.urticae Koch (Tetranychus urticae) Spider mite (twospotted spider mite)) and Di Shi watts of mite (Varroa destructor) (honeybee mite).
Nematoda (nematode): Aphelenchoides kind (Aphelenchoides spp.) (bud and leaf and Bursaphelenchus xylophilus (bud And leaf &pine wood nematode)), thorn Turbatrix kind (Belonolaimus spp.) (sting Nematodes), small loop wire Eimeria kind (Criconemella spp.) (ring nematodes), heart worm (Dirofilaria immitis) (dog heartworm), Ditylenchus kind (Ditylenchus spp.) (stem and bulb line Worm), spine rubber-insulated wire Eimeria kind (Heterodera spp.) (cyst nematode), corn cyst nematode (Heterodera Zeae) (corn cyst nematode), Hirschmanniella kind (Hirschmanniella spp.) (root nematodes), Tie Turbatrix kind (Hoplolaimus spp.) (lance nematodes), Meloidogyne kind (Meloidogyne Spp.) (root-knot nematode), Meloidogyne incognita ((Meloidogyne incognita) (root-knot nematode), Onchocerca caecutiens (Onchocerca volvulus) (hook-tail worm), Pratylenchus kind (PraLylenchus spp.) (rotten nematode (lesion nematode)), perforation line Eimeria kind (Radopholus spp.) (similes thorne (burrowing )) and banana reniform nematode (Rotylenchus reniformis) (kidney-shaped nematode) nematode.
Symphyla (comprehensive insects): kahikatea worm (Scutigerella immaculata).
Due to its positive characteristic, above compound is advantageously used for protection agricultural and the important crop of horticulture, family Injury of the environment that poultry and breeding stock and the mankind often go from pest harmful mite.
To obtain ideal effect, the dosage of compound changes because of various factors, such as compound used therefor, the work protected in advance Object, the type of harmful organism, gradient of infection, weather conditions, application method, the dosage form of use.
10 grams -5 kilograms of per hectare of compound dosage can provide sufficient prevention and treatment.
The invention also includes the insecticide acaricide compositions using compound shown in general formula I as active component.The Insecticiding-miticiding The weight percentage of active component is between 0.5-99% in composition.It further include agricultural, woods in the insecticide acaricide composition Acceptable carrier in industry, health.
Composition of the invention can be applied in the form of preparation.Compound shown in general formula I dissolves or divides as active component It is more readily dispersible when dissipating in carrier or being configured to preparation to use as sterilization, desinsection.Such as: these chemicals can quilt Wettable powder, oil suspending agent, aqueous suspension, aqueous emulsion, aqua or missible oil etc. is made.In these compositions, one kind is at least added Liquid or solid carrier, and surfactant appropriate can be added when needed.
Technical solution of the present invention further includes the method for pest control harmful mite: insecticide acaricide composition of the invention is imposed on In the pest harmful mite or its somatomedin.The more suitable effective amount generally selected is 10 grams to 1000 grams of per hectare, excellent Selecting effective quantity is 20 grams to 500 grams of per hectare.
For certain applications, for example, can be agriculturally added in insecticide acaricide composition of the invention it is one or more its Thus its fungicide, insecticidal/acaricidal agent, herbicide, plant growth regulator or fertilizer etc. can produce additional advantage and effect Fruit.
It should be appreciated that various transformation and change can be carried out in scope defined by the claims of the present invention.
Specific embodiment
Following specific embodiments be used to further illustrate the present invention, but the present invention is by no means limited to these examples (except as otherwise It is raw materials used to be commercially available outside indicating).
Synthetic example
Embodiment 1: the preparation of the chloro- 6- methylpyrimidine of intermediate 4,5- bis-
1) preparation of the chloro- 6- methylpyrimidine of 4- hydroxyl -5-
It is stirred at room temperature and lower 8.80g is slowly added dropwise into the 50ml methanol solution of 11.30g (0.11mol) formamidine acetate The methanol solution of (0.16mol) sodium methoxide drips complete room temperature and continues to stir 2h.It states then up and 11.17g is added dropwise in solution (0.068mol) intermediate 2- chloroacetyl acetacetic ester continues that reaction 5-7 hours is stirred at room temperature.TLC is monitored after completion of the reaction, is subtracted Solvent is evaporated off in pressure, with hydrochloric acid tune pH=5~6, filters to obtain orange/yellow solid, water phase is extracted with (3 × 50ml) ethyl acetate, anhydrous Magnesium sulfate is dry, filters, precipitation.Residue is dissolved in 50ml ethyl acetate, is stood overnight, and orange/yellow solid 6.48g is filtered to obtain. Yield 66%, 181~184 DEG C of fusing point.
2) preparation of the chloro- 6- methylpyrimidine of 4,5- bis-
The chloro- 6- methylpyrimidine of 14.5g (0.1mol) 4- hydroxyl -5- is dissolved in 50ml toluene solution, to reaction under stirring 50ml phosphorus oxychloride is instilled in bottle, is dripped and is finished temperature rising reflux reaction 5-7 hours.TLC monitor after completion of the reaction, remove under reduced pressure toluene and Reactant, is poured into ice water by excessive phosphorus oxychloride under stirring, and water phase is extracted with (3 × 50ml) ethyl acetate, merges organic Phase, anhydrous magnesium sulfate is dry, filters, precipitation.Residue column chromatography (eluant, eluent be ethyl acetate and petroleum ether, volume ratio 1: 5) yellow liquid 14.43g, yield 88.5% are separated to obtain.
The preparation of embodiment 2:4,5- dichloro-thiophene simultaneously [2,3-d] pyrimidine
Take 2- Amino 3 cyano -4- oxo -5,5- dihydro-thiophene and 250ml phosphorus oxychloride (POCl3) in reaction flask, 38ml n,N-Dimethylformamide is slowly added dropwise at room temperature, is added dropwise within about 30 minutes.Room temperature reaction 1 hour, then it is warming up to 75 DEG C reaction 3 hours.It is cooled to room temperature, reaction solution is poured into trash ice, filter to obtain dark gray solid 89.1g, yield 86.9% melts 160-161 DEG C of point.
Embodiment 3: the preparation of intermediate 4- chloro-quinazoline
1) preparation of quinazoline -4 (3H) -one
It takes 13.7g (0.1mol) ortho-aminobenzoic acid and 20ml formamide in 250ml there-necked flask, is warming up to 140 DEG C instead It answers 5-8 hours.TLC is monitored after completion of the reaction, and reaction solution is cooled to 100 DEG C, is stirred lower dropwise addition 80ml water, is cooled to room later Temperature filters and obtains rufous 10.96g, yield 75.1% with filter cake is washed with anhydrous ether.
2) preparation of 4- chloro-quinazoline
Take 14.6g (0.1mol) (3H) -one of quinazoline -4 in 250ml single port bottle, 50ml thionyl chloride makees solvent, heating To back flow reaction 4-6 hours.TLC is monitored after completion of the reaction, is poured into water reaction solution after cooling and is stirred 30min, filtering is used in combination Anhydrous ether washs to obtain red brown solid 10.96g, yield 92.7%.
Embodiment 4: the synthesis of intermediate 3- (5- p-fluorophenyl -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride
1) preparation of N-Boc-2- bromine propylamine
20.5g (0.1mol) bromine ethamine bromate is placed in 80ml tetrahydrofuran, 10.08g (0.12mol) is sequentially added Sodium bicarbonate, 50ml water, are stirred at room temperature lower dropwise addition 21.80g (0.1mol) di-tert-butyl dicarbonate, and drop finishes, the reaction was continued 4-10 Hour.After completion of the reaction, the extraction of (3 × 50ml) ethyl acetate, organic phase saturated salt solution 50ml is added in evaporating solvent under reduced pressure It washs, colourless oil liquid 21.1g, yield 94.% is obtained after precipitation.
2) preparation of N-Boc-2- (5- p-fluorophenyl -1- methyl pyrazole -3- oxygroup) ethamine
By 2.24g (0.01mol) N-Boc-2- bromine ethamine and 2.02g (0.01mol) 5- p-fluorophenyl -1- methyl -3- hydroxyl Base pyrazoles (preparation method refers to CN102584705) is added in 50ml butanone, 2.76g (0.02mol) potassium carbonate is added, under stirring It is heated to flowing back, react 4-10 hours, TLC is monitored after completion of the reaction, and (3 × 50ml) ethyl acetate is added in evaporating solvent under reduced pressure Extraction, organic phase wash with saturated salt solution 50ml, residue column chromatography after precipitation (eluant, eluent is ethyl acetate and petroleum ether, Volume ratio is 1:6) obtain yellow solid 2.81g, yield 81.4%.
3) preparation of 3- (5- p-fluorophenyl -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride
3.45g (0.01mol) N-Boc-2- (5- (2,4 dichloro benzene base) -1- methyl pyrazole -3- oxygroup) ethamine is added In 50ml ethyl acetate, lower dropwise addition 6ml concentrated hydrochloric acid is stirred at room temperature, solid dissolution continues stirring 4-5 hours, TLC monitoring reaction After, evaporating solvent under reduced pressure is added 10ml methylene chloride and stirs half an hour, filtering, and washs filter cake with methylene chloride and obtain 2.85g light yellow solid.
Embodiment 5: the synthesis of intermediate 1- methyl -2- (5- phenyl -1,4- dimethyl -3- oxygroup) ethamine
1) preparation of 1- (5- phenyl -1,4- Dimethyl-pyrazol -3- oxygroup) acetone
By 0.93g (0.01mol) chlroacetone and 1.88g (0.01mol) 5- phenyl -1,4- dimethyl -3- hydroxypyrazoles (system Preparation Method refers to CN102584705) it is added in 50ml DMF, 2.76g (0.02mol) potassium carbonate is added, is heated to back under stirring Stream reacts 4-10 hours, and TLC is monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, organic Mutually wash with saturated salt solution 50ml, after precipitation residue column chromatograph (eluant, eluent be ethyl acetate and petroleum ether, volume ratio 1: 5) red brown solid 3.15g, yield 79.5% are obtained.
2) preparation of 1- methyl -2- (5- phenyl -1,4- dimethyl -3- oxygroup) ethamine
By 2.44g (0.01mol) 1- (5- phenyl -1,4- Dimethyl-pyrazol -3- oxygroup) acetone and 11.5g (0.15mol) Ammonium acetate is added in 50ml methanol, and 1.26g (0.02mol) sodium cyanoborohydride is added portionwise, and 1ml glacial acetic acid is added dropwise after adding, It is stirred to react under ice valley 4-10 hours, TLC is monitored after completion of the reaction, and sodium hydrate aqueous solution is added dropwise into reaction solution to pH=8- 9, the extraction of (3 × 50ml) ethyl acetate is added, organic phase is washed with saturated salt solution 50ml, and yellow oil is obtained after precipitation 1.96g。
Embodiment 6: the preparation of compound 10-1-57
By the chloro- 6- methylpyrimidine of 1.63g (0.01mol) 4,5- bis- and 2.82g (0.01mol) 3- (5- p-methylphenyl -1,4- Dimethyl-pyrazol -3- oxygroup) propylamin hydrochloride be added 50ml toluene in.4.45g (0.022mol) triethylamine is added, is heated to Reflux is reacted 4-10 hours, and TLC is monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, has Machine is mutually washed with saturated salt solution 50ml, and (eluant, eluent is ethyl acetate and petroleum ether (boiling range 60- to residue column chromatography after precipitation 90 DEG C), volume ratio 1:2) faint yellow solid 2.08g, 154.6 DEG C of fusing point, yield 56.1%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.38(s,1H,Pyrimidine-H),7.28 (d, J=6Hz, 2H, Ph-2,6-2H), 7.19 (d, J=6Hz, 2H, Ph-3,5-2H), 6.48 (s, 1H, NH), 4.47 (t, J=6 Hz,2H,O-CH2),3.91(m,2H,NH-CH2),3.61(s,3H,N-CH3),2.46(s,3H,Pyrimidine-CH3), 2.42(s,3H,Ph-4-CH3),2.42(s,3H,Pyrazole-CH3).
Embodiment 7: the preparation of compound 19-21
By 1.65g (0.01mol) 4- chloro-quinazoline and 3.22g (0.01mol) 3- (5- (2,4 dichloro benzene base) -1- methyl - Pyrazoles -3- oxygroup) ethylamine hydrochloride be added 50ml toluene in.4.45g (0.022mol) triethylamine is added, is heated to flowing back, instead It answers 4-10 hours, TLC is monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, and organic phase is used Saturated salt solution 50ml washing, residue column chromatography after precipitation (eluant, eluent is ethyl acetate and petroleum ether (60-90 DEG C of boiling range), Volume ratio is 1:2) obtain brown oil 2.85g, yield 68.8%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.70(s,1H,Quinazoline-3-H), 7.88 (d, J=6Hz, 1H, Quinazoline-5-H), 7.77 (t, J=6Hz, 1H, Quinazoline-6-H), 7.74 (d, J =6 Hz, 1H, Quinazoline-8-H), 7.70 (d, J=12Hz, 1H, Ph-6-H), 7.49 (t, J=6Hz, 1H, ), Quinazoline-7-H 7.41 (s, 1H, Ph-3-H), 7.25 (d, J=12Hz, 1H, Ph-5-H), 6.19 (s, 1H, NH), 6.10 (s, 1H, Pyrazole-4-H), 4.42 (t, J=6Hz, 2H, O-CH2), 4.13-4.16 (q, J=6Hz, 2H, N-CH2), 3.72(s,3H,N-CH3).
Embodiment 8: the preparation of compound 21-1-72
By 2.05g (0.01mol) 4,5- dichloro-thiophene simultaneously [2,3-d] pyrimidine and 2.98g (0.01mol) 3- (5- (2,4- bis- Chlorphenyl) -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride be added 50ml toluene in.4.45g (0.022mol) three second is added Amine is heated to flowing back, and reacts 4-10 hours, and TLC is monitored after completion of the reaction, and (3 × 50ml) acetic acid is added in evaporating solvent under reduced pressure Ethyl ester extraction, organic phase are washed with saturated salt solution 50ml, and (eluant, eluent is ethyl acetate and petroleum to residue column chromatography after precipitation Ether (60-90 DEG C of boiling range), volume ratio 1:2) yellow solid 2.24g, 121.7 DEG C of fusing point, yield 52.1%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.47(s,1H,Pyrimidine-H),7.22 (d, J=6Hz, 2H, Ph-2,6-2H), 7.07 (s, 1H, NH), 7.06 (s, 1H, Thiophene-H), 6.99 (d, J=6Hz, 2H, Ph-3,5-2H), 4.50 (t, J=6Hz, 2H, O-CH2), 4.05-4.07 (q, J=6Hz, 2H, N-CH2),3.86(s,3H, N-CH3),3.58(s,3H,OCH3),1.86(s,3H,Pyrazole-4-CH3).
Embodiment 9: the preparation of compound 19-34
By 1.65g (0.01mol) 4- chloro-quinazoline and 3.33g (0.01mol) 3- (5- (4- bromophenyl) -1- methyl-pyrrole Azoles -3- oxygroup) ethylamine hydrochloride be added 50ml toluene in.4.45g (0.022mol) triethylamine is added, is heated to flowing back, reacts 4-10 hours, TLC was monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, and organic phase is used full It is washed with saline solution 50ml, (eluant, eluent is ethyl acetate and petroleum ether (60-90 DEG C of boiling range), body to residue column chromatography after precipitation Product than be 1:2) white solid 2.09g, 131.4 DEG C of fusing point, yield 49.4%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.66(s,1H,Quinazoline-3-H), 7.84 (d, J=6Hz, 2H, Quinazoline-5,8-2H), 7.73 (t, J=6Hz, 2H, Quinazoline-6,7-2H), 7.45 (d, J=6Hz, 2H, Ph-2,6-2H), 7.39 (d, J=6Hz, 2H, Ph-3,5-2H), 7.05 (s, 1H, NH), 5.87 (s, 1H, Pyrazole-4-H), 4.51 (t, J=6Hz, 2H, O-CH2),4.04-4.09(q,2H,N-CH2),3.77(s,3H, N-CH3).
Embodiment 10: the preparation of compound 11-4-1
By the chloro- 6- ethyl-pyrimidine of 1.77g (0.01mol) 4,5- bis- and 2.45g (0.01mol) 1- methyl -2- (5- phenyl - 1,4- dimethyl -3- oxygroup) ethamine be added 50ml toluene in.4.45g (0.022mol) triethylamine is added, is heated to flowing back, instead It answers 4-10 hours, TLC is monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, and organic phase is used Saturated salt solution 50ml washing, residue column chromatography after precipitation (eluant, eluent is ethyl acetate and petroleum ether (60-90 DEG C of boiling range), Volume ratio is 1:2) obtain yellow oil 1.05g, yield 27.2%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.42(s,1H,Pyrimidine-H),7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.30 (d, J=6Hz, 2H, Ph-2,6-2H), 6.22 (s, 1H, NH), 4.59-4.62 (m, 1H, N-CH), 4.35 (d, J=6Hz, 2H, O-CH2),3.61(s,3H, N-CH3), 2.76-2.80 (q, J=6Hz, 2H, CH2CH3),1.86(s,3H,Pyrazole-4-CH3), 1.41 (d, J=6Hz, 3H, CHCH3), 1.26 (t, J=6Hz, 3H, CH2CH3).
Other compounds of the invention are referred to above embodiments preparation.
Part of compounds physical data and nuclear magnetic data (1HNMR, 600MHz, internal standard TMS, ppm) as follows:
Compound 10-1: 118.2 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.72(m,2H, Ph-2,6-2H),7.37(m,2H,Ph-3,5-2H),7.29(m,1H,Ph-4-H),5.85(s,1H,Pyrazole-H),5.75 (s, 1H, NH), 4.30 (t, J=6Hz, 2H, O-CH2),3.98(m,2H,NH-CH2),3.71(s,3H,N-CH3).
Compound 10-21: 110.8 DEG C of fusing point.δ(CDCl3): 8.40 (s, 1H, Pyrimidine-H), 7.72 (d, J= 6Hz, 1H, Ph-6-H), 7.43 (s, 1H, Ph-3-H), 7.25 (dd, J=6Hz, 1H, Ph-5-H), 6.09 (s, Pyrazole- 4-H), 5.72 (s, 1H, NH), 4.30 (t, J=6Hz, 2H, O-CH2), 3.96-3.99 (q, J=6Hz, 2H, N-CH3),3.72 (s,3H, N-CH3),2.48(s,3H,CH3).
Compound 10-34: 112.9 DEG C of fusing point.δ(CDCl3): 8.41 (s, 1H, Pyrimidine-H), 7.59 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.49 (d, J=6Hz, 2H, Ph-3,5-2H), 5.82 (s, 1H, Pyrazole-H), 5.71 (s, 1H, NH), 4.29 (t, J=6Hz, 2H, O-CH2),3.98(m,2H),3.70(s,3H,NH-CH2),2.48(s,3H, Pyrimidine-CH3).
Compound 10-69: 145.3 DEG C of fusing point.δ(CDCl3): 8.41 (s, 1H, Pyrimidine-H), 7.82 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.62 (d, J=6Hz, 2H, Ph-3,5-2H), 5.89 (s, 1H, Pyrazole-4-H), 5.72 (s, 1H, NH), 4.31 (t, J=6Hz, 2H, O-CH2), 3.97-4.00 (q, J=6Hz, 2H, N-CH2),3.72(s,3H,N- CH3),2.48(s, 3H,Pyrimidine-CH3)。
Compound 10-1-19: 109.4 DEG C of fusing point.δ(CDCl3): 8.38 (s, 1H, Pyrimidine-H), 7.45 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.25 (d, J=6Hz, 2H, Ph-3,5-2H), 6.42 (s, 1H, NH), 4.47 (t, J=6Hz, 2H, O-CH2),3.91(m,2H,NH-CH2),3.61(s,3H,N-CH3),2.46(s,3H,Pyrimidine-CH3),1.86 (s, 3H,Pyrazole-4-CH3).
Compound 10-1-72: 110.6 DEG C of fusing point.δ(CDCl3): 8.37 (s, 1H, Pyrimidine-H), 7.23 (d, J= 6Hz, 2H, Ph-2,6-2H), 6.99 (d, J=6Hz, 2H, Ph-3,5-2H), 6.47 (s, 1H, NH), 4.47 (t, J=6Hz, 2H, O-CH2), 3.89-3.92 (q, J=6Hz, 2H, N-CH2),3.86(s,3H,N-CH3),3.60(s,3H,OCH3),2.46 (s, 3H,Pyrimidine-CH3),1.86(s,3H,Pyrazole-4-CH3).
Compound 10-3-1: grease.δ(CDCl3): 8.37 (s, 1H, Pyrimidine-H), 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 6.23 (s, 1H, NH), 4.39 (t, J=6Hz, 2H, O-CH2), 3.71-3.74 (q, J=6Hz, 2H, N-CH2),3.63(s,3H,N-CH3), 2.45(s, 3H,CH3),2.10-2.14(m,2H,CH2),1.89(s,3H,Pyrazole-4-CH3).
Compound 10-4-1: grease.δ(CDCl3): 8.37 (s, 1H, Pyrimidine-H), 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.30 (d, J=6Hz, 2H, Ph-2,6-2H), 6.22 (s, 1H, NH), 4.58-4.63 (m, 1H, N-CH), 4.35 (d, J=6Hz, 2H, O-CH2),3.61(s,3H,N-CH3),2.45(s, 3H, CH3),1.86(s,3H,Pyrazole-4-CH3), 1.41 (d, J=6Hz, 3H, CHCH3).
Compound 11-1: 128.4 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.29-7.45(m, 5H, Ph-5H),6.21(s,1H,NH),5.74(s,1H,Pyrazole-H),4.40(t,2H,O-CH2),3.90(m,2H,N- CH2), 3.72(s,3H,N-CH3),2.79(m,2H,CH2),1.27(t,3H,CH3)。
Compound 11-21: 135.9 DEG C of fusing point.δ(CDCl3): 8.45 (s, 1H, Pyrimidine-H), 7.72 (d, J= 6Hz, 1H, Ph-6-H), 7.43 (s, 1H, Ph-3-H), 7.25 (dd, J=6Hz, 1H, Ph-5-H), 6.09 (s, Pyrazole- 4-H), 5.73 (s, 1H, NH), 4.31 (t, J=6Hz, 2H, O-CH2), 3.96-3.99 (q, J=6Hz, 2H, N-CH2),3.72 (s,3H, N-CH3), 2.79-2.83 (m, J=6Hz, 2H, CH2CH3), 1.27 (t, J=6Hz, 3H, CH2CH3).
Compound 11-34: grease.δ(CDCl3):8.42(s,1H,Pyrimidine-H),7.58(m,2H,Ph-2,6- 2H), 7.26(t,2H,Ph-3,5-2H),6.16(s,1H,NH),5.73(s,1H,Pyrazole-H),4.39(t,2H,O- CH2),3.89 (m,2H,N-CH2),3.70(s,3H,N-CH3),2.80(m,2H,CH2),1.28(t,3H,CH3)。
Compound 11-69: 124.8 DEG C of fusing point.δ(CDCl3): 8.46 (s, 1H, Pyrimidine-H), 7.82 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.62 (d, J=6Hz, 2H, Ph-3,5-2H), 5.89 (s, 1H, Pyrazole-4-H), 5.73 (s, 1H, NH), 4.32 (t, J=6Hz, 2H, O-CH2), 3.97-4.00 (q, J=6Hz, 2H, N-CH2),3.72(s,3H,N- CH3), 2.79-2.83 (q, J=6Hz, 2H, CH2CH3), 1.27 (t, J=6Hz, 3H, CH2CH3).
Compound 11-1-1: 92.9 DEG C of fusing point.δ(CDCl3):8.42(s,1H,Pyrimidine-H),7.45-7.47(d, 2H, Ph-2,6-2H),7.43(t,1H,Ph-4-H),7.32(t,2H,Ph-3,5-2H),6.43(s,1H,NH),4.47(t, 2H, O-CH2),3.89-3.94(m,2H,N-CH2),3.62(s,3H,N-CH3),2.75-2.83(m,2H,CH2),1.88(s, 3H, Pyrazole-4-CH3),1.26(t,3H,CH3)。
Compound 11-1-4: grease.δ(CDCl3):8.43(s,1H,Pyrimidine-H),7.25-7.29(m,2H, Ph-2,6-2H),7.15-7.18(t,2H,Ph-3,5-2H),6.41(s,1H,NH),4.47(t,2H,O-CH2),3.91(m, 2H, N-CH2),3.60(s,3H,N-CH3),2.80(m,2H,CH2),1.85(s,3H,Pyrazole-4-CH3),1.26(t, 3H, CH3)。
Compound 11-1-19: 113.5 DEG C of fusing point.δ(CDCl3):8.43(s,1H,Pyrimidine-H),7.45(m,2H, Ph-2,6-2H),7.24(t,2H,Ph-3,5-2H),6.38(s,1H,NH),4.46(t,2H,O-CH2),3.91(m,2H, N- CH2),3.61(s,3H,N-CH3),2.79(m,2H,CH2),1.86(s,3H,Pyrazole-4-CH3),1.25(t,3H, CH3)。
Compound 11-1-57: 134.0 DEG C of fusing point.δ(CDCl3):8.43(s,1H,Pyrimidine-H),7.27(m,2H, Ph-2,6-2H),7.20(t,2H,Ph-3,5-2H),6.46(s,1H,NH),4.47(t,2H,O-CH2),3.91(m,2H, N- CH2),3.61(s,3H,N-CH3),2.81(m,2H,CH2),2.42(s,3H,Ph-CH3),1.87(s,3H, Pyrazole-4- CH3),1.28(t,3H,CH3)。
Compound 11-1-72: grease.δ(CDCl3): 8.42 (s, 1H, Pyrimidine-H), 7.23 (d, J=6Hz, 2H, Ph-2,6-2H), 6.99 (d, J=6Hz, 2H, Ph-3,5-2H), 6.47 (s, 1H, NH), 4.47 (t, J=6Hz, 2H, O- CH2), 3.90-3.92 (q, J=6Hz, 2H, N-CH2),3.86(s,3H,N-CH3),3.61(s,3H,OCH3),2.77-2.81 (q, J=6Hz, 2H, CH2CH3),1.86(s,3H,Pyrazole-4-CH3), 1.26 (t, J=6Hz, 3H, CH2CH3).
Compound 11-3-1: grease.δ(CDCl3): 8.42 (s, 1H, Pyrimidine-H), 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 6.23 (s, 1H, NH), 4.39 (t, J=6Hz, 2H, O-CH2), 3.71-3.74 (q, J=6Hz, 2H, N-CH2),3.63(s,3H,N-CH3), 2.77-2.80 (q, J=6Hz, 2H, CH2CH3),2.10-2.14(m,2H,CH2),1.90(s,3H,Pyrazole-4-CH3), 1.26 (t, J=6Hz, 3H, CH2CH3).
Compound 12-1: 91.6 DEG C of fusing point.δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.67-7.74(m, 2H, Ph-2,6-2H), 7.33-7.42 (m, 2H, Ph-3,5-2H), 7.25-7.31 (m, 1H, Ph-4-H), 6.73 (t, J= 54Hz,1H, CHF2), 6.06 (s, 1H, NH), 5.85 (s, 1H, Pyrazole-H), 4.31 (t, J=6Hz, 2H, O-CH2), 4.03(m,2H, NH-CH2),3.70(s,3H,N-CH3).
Compound 12-21: 105.4 DEG C of fusing point.δ(CDCl3): 8.59 (s, 1H, Pyrimidine-H), 7.72 (d, J= 6Hz, 1H, Ph-6-H), 7.43 (s, 1H, Ph-3-H), 7.26 (dd, J=6Hz, 1H, Ph-5-H), 6.73 (t, JHF=54Hz, 1H,CHF2), 6.10 (s, Pyrazole-4-H), 6.00 (s, 1H, NH), 4.33 (t, J=6Hz, 2H, O-CH2),4.02-4.05 (q, J=6Hz, 2H, N-CH2),3.72(s,3H,N-CH3).
Compound 12-34: 107.0 DEG C of fusing point.δ(CDCl3): 8.55 (s, 1H, Pyrimidine-H), 7.44 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.39 (d, J=6Hz, 2H, Ph-3,5-2H), 6.73 (t, JHF=54Hz, 1H, CHF2),6.70 (s, 1H, NH), 5.74 (s, 1H, Pyrazole-4-H), 4.44 (t, J=6Hz, 2H, O-CH2), 3.94-3.97 (q, J= 6Hz,2H,N-CH2), 3.73(s,3H,N-CH3).
Compound 12-69: 127.1 DEG C of fusing point.δ(CDCl3): 8.59 (s, 1H, Pyrimidine-H), 7.82 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.62 (d, J=6Hz, 2H, Ph-3,5-2H), 6.73 (t, JHF=54Hz, 1H, CHF2),6.01 (s, 1H, NH), 5.89 (s, 1H, Pyrazole-4-H), 4.33 (t, J=6Hz, 2H, O-CH2), 4.03-4.06 (q, J= 6Hz,2H, N-CH2),3.72(s,3H,N-CH3).
12-1-1: δ (CDCl of compound3):8.55(s,1H,Pyrimidine-H),7.45-7.48(d,2H,Ph-2,6- 2H), 7.44(t,1H,Ph-4-H),7.30(t,2H,Ph-3,5-2H),7.02(s,1H,NH),6.73(s,1H,CH),4.51 (t,2H, O-CH2),3.92-3.97(m,2H,N-CH2),3.62(s,3H,N-CH3),1.87(s,3H,Pyrazole-4- CH3)。
Compound 12-1-4: 88.8 DEG C of fusing point.δ(CDCl3):8.55(s,1H,Pyrimidine-H),7.28(m,2H, ), Ph-2,6-2H 7.14 (m, 2H, Ph-3,5-2H), 7.01 (s, 1H, NH), 6.75 (s, J=54Hz, 1H, CHF2),4.50(t, J=6Hz, 2H, O-CH2),3.95(m,2H,NH-CH2),3.60(s,3H,N-CH3),1.84(s,3H, Pyrazole-4- CH3).
Compound 12-1-19: 100.6 DEG C of fusing point.δ(CDCl3): 8.56 (s, 1H, Pyrimidine-H), 7.48 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.25 (d, J=6Hz, 2H, Ph-3,5-2H), 6.96 (s, 1H, NH), 6.73 (t, J=54Hz, 1H, CHF2), 4.49 (t, J=6Hz, 2H, O-CH2),3.95(m,2H,NH-CH2),3.61(s,3H,N-CH3),1.86(s, 3H, Pyrazole-4-CH3).
Compound 12-1-57: grease.δ(CDCl3): 8.55 (s, 1H, Pyrimidine-H), 7.27 (d, J=6Hz, 2H, Ph-2,6-2H), 7.19 (d, J=6Hz, 2H, Ph-3,5-2H), 7.06 (s, 1H, NH), 6.73 (t, JHF=54Hz, 1H, ), CH 4.51 (t, J=6Hz, 2H, O-CH2), 3.93-3.95 (q, J=6Hz, 2H, N-CH2),3.61(s,3H,N-CH3), 2.42(s, 3H,Ph-4-CH3),1.86(s,3H,Pyrazole-4-CH3).
Compound 12-1-72: grease.δ(CDCl3): 8.55 (s, 1H, Pyrimidine-H), 7.22 (d, J=6Hz, 2H, Ph-2,6-2H), 7.06 (s, 1H, NH), 6.99 (d, J=6Hz, 2H, Ph-3,5-2H), 6.73 (t, JHF=54Hz, 1H, CHF2), 4.50 (t, J=6Hz, 2H, O-CH2), 3.93-3.95 (q, J=6Hz, 2H, N-CH2),3.86(s,3H,N-CH3), 3.60(s, 3H,OCH3),1.86(s,3H,Pyrazole-4-CH3).
Compound 12-3-1: yellow oil.δ(CDCl3): 8.54 (s, 1H, Pyrimidine-H), 7.48 (t, J= 6Hz, 2H, Ph-3,5-2H), 7.42 (t, J=6Hz, 1H, Ph-4-H), 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 6.75 (s,1H,NH), 6.73(t,JHF=54Hz, 1H, CHF2), 4.41 (t, J=6Hz, 2H, O-CH2), 3.77-3.80 (q, J= 6Hz,2H, N-CH2),3.63(s,3H,N-CH3),2.10-2.14(m,2H,CH2),1.89(s,3H,Pyrazole-4-CH3).
Compound 12-4-1: grease.δ(CDCl3): 8.46 (s, 1H, Pyrimidine-H), 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 7.04 (s, 1H, Thiophene-H), 6.89 (s, 1H, NH), 4.40 (t, J=6Hz, 2H, O-CH2), 3.85-3.88 (q, J=6Hz, 2H, N-CH2),3.61(s,3H,N-CH3),2.19-2.23(m,2H,CH2),1.87(s,3H,Pyrazole-4-CH3).
Compound 19-69: 175.9 DEG C of fusing point.δ(CDCl3):8.71(s,1H,Quinazoline-3-H),7.89(d,J =6Hz, 1H, Quinazoline-5-H), 7.79 (d, J=6Hz, 2H, Ph-2,6-2H), 7.77 (t, J=6Hz, 1H, ), Quinazoline-6-H 7.72 (d, J=6Hz, 1H, Quinazoline-8-H), 7.61 (d, J=6Hz, 2H, Ph-3,5- 2H), 7.50 (t, J=6Hz, 1H, Quinazoline-7-H), 6.07 (s, 1H, NH), 5.91 (s, 1H, Pyrazole-4-H), 4.43 (t, J=6Hz, 2H, O-CH2), 4.15-4.18 (q, J=6Hz, 2H, N-CH2),3.73(s,3H,N-CH3).
Compound 19-1-72: grease.δ(CDCl3): 8.67 (s, 1H, Quinazoline-3-H), 7.88 (d, J= 12Hz, 1H, Quinazoline-5-H), 7.85 (d, J=6Hz, 1H, Quinazoline-8-H), 7.73 (m, 1H, ), Quinazoline-6-H 7.63 (s, 1H, NH), 7.44 (d, J=6Hz, 1H, Quinazoline-7-H), 7.23 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.01 (d, J=6Hz, 2H, Ph-3,5-2H), 4.60 (t, J=6Hz, 2H, O-CH2),4.03- 4.05 (q, J=6Hz, 2H, N-CH2),3.87(s,3H,N-CH3),3.69(s,3H,OCH3),1.87(s,3H,Pyrazole- 4-CH3).
Compound 19-3-1: 109.6 DEG C of fusing point.δ(CDCl3):8.66(s,1H,Quinazoline-3-H),7.88(d,J =6Hz, 1H, Quinazoline-5-H), 7.84 (d, J=6Hz, 1H, Quinazoline-8-H), 7.72 (t, J=6Hz, 1H, Quinazoline-6-H), 7.48 (t, J=6Hz, 2H, Ph-3,5-2H), 7.43 (m, 2H, Ph-4-H+ ), Quinazoline-7-H 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 7.12 (s, 1H, NH), 4.48 (t, J=6Hz, 2H, O-CH2),3.88-3.91(q, 2H,N-CH2),3.67(s,3H,N-CH3),2.19-2.23(m,2H,CH2),1.92(s,3H, Pyrazole-4-H).
Compound 19-4-1: grease.δ(CDCl3): 8.66 (s, 1H, Quinazoline-3-H), 7.84 (d, J= 6Hz, 1H, Quinazoline-5-H), 7.82 (d, J=6Hz, 1H, Quinazoline-8-H), 7.71 (t, J=6Hz, 1H, ), Quinazoline-6-H 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 2H, Ph-4-H, ), Quinazoline-7-H 7.40 (s, 1H, NH), 7.29 (d, J=6Hz, 2H, Ph-2,6-2H), 4.76-4.79 (m, 1H, N- ), CH 4.47 (d, J=6Hz, 2H, O-CH2),3.69(s,s,3H,N-CH3),1.87(s,3H,Pyrazole-4-CH3), 1.48 (d, J=6Hz, 3H, CHCH3).
Compound 21-1: 136.8 DEG C of fusing point.δ(CDCl3):8.50(s,1H,Pyrimidine-H),7.68-7.73(m, 2H, Ph-2,6-2H),7.37(m,2H,Ph-3,5-2H),7.26-7.30(m,1H,Ph-4-H),7.11(s,1H, ), Thiophene-H 6.91 (s, 1H, NH), 5.87 (s, 1H, Pyrazole-H), 4.37 (t, J=6Hz, 2H, O-CH2), 4.11(m,2H, NH-CH2),3.72(s,3H,N-CH3).
Compound 21-21: 123.8 DEG C of fusing point.δ(CDCl3): 8.49 (s, 1H, Pyrimidine-H), 7.72 (d, J= 6Hz, 1H, Ph-6-H), 7.43 (s, 1H, Ph-3-H), 7.26 (dd, J=6Hz, 1H, Ph-5-H), 7.11 (s, 1H, ), Thiophene-H 6.90 (s, 1H, NH), 6.11 (s, Pyrazole-4-H), 4.37 (t, J=6Hz, 2H, O-CH2), 4.09-4.12 (q, J=6Hz, 2H, N-CH2),3.72(s,3H,N-CH3).
Compound 21-34: grease.δ(CDCl3): 8.47 (s, 1H, Pyrimidine-H), 7.44 (d, J=6Hz, 2H, Ph-2,6-2H),7.39(d,2H,Ph-3,5-2H),7.07(s,1H,Thiophene-H),7.00(s,1H,NH),5.75(s, 1H, Pyrazole-4-H), 4.44 (t, J=6Hz, 2H, O-CH2), 4.03-4.08 (q, J=6Hz, 2H, N-CH2),3.72(s, 3H,N-CH3)。
Compound 21-69: 177.3 DEG C of fusing point.δ(CDCl3): 8.50 (s, 1H, Pyrimidine-H), 7.82 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.62 (d, J=6Hz, 2H, Ph-3,5-2H), 7.11 (s, 1H, Thiophene-H), 6.89 (s, 1H, NH), 5.91 (s, 1H, Pyrazole-4-H), 4.38 (t, J=6Hz, 2H, O-CH2), 4.10-4.13 (q, J=6Hz, 2H,N-CH2), 3.73(s,3H,N-CH3).
Compound 21-1-4: 148.2 DEG C of fusing point.δ(CDCl3):8.47(s,1H,Pyrimidine-H),7.30(m,2H, ), Ph-2,6-2H 7.16 (m, 2H, Ph-3,5-2H), 7.06 (s, 2H, Thiophene-H+NH), 4.50 (t, J=6Hz, 2H, O-CH2),4.06(m,2H,NH-CH2),3.58(s,3H,N-CH3),1.85(s,3H,Pyrazole-4-CH3).
Compound 21-1-19: 161.2 DEG C of fusing point.δ(CDCl3): 8.47 (s, 1H, Pyrimidine-H), 7.45 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.23 (d, J=6Hz, 2H, Ph-3,5-2H), 7.06 (s, 1H, Thiophene-H), 7.05 (s, 1H, NH), 4.50 (t, J=6Hz, 2H, O-CH2),4.06(m,2H,NH-CH2),3.58(s,3H,N-CH3),1.86(s,3H, Pyrazole-4-CH3).
Compound 21-1-57: 149.3 DEG C of fusing point.δ(CDCl3): 8.47 (s, 1H, Pyrimidine-H), 7.27 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.19 (d, J=6Hz, 2H, Ph-3,5-2H), 7.07 (s, 1H, NH), 7.05 (s, 1H, ), Pyrazole-H 4.50 (t, J=6Hz, 2H, O-CH2),4.06(m,2H,NH-CH2),3.59(s,3H,N-CH3),2.41 (s,3H, Ph-CH3),1.87(s,3H,Pyrazole-CH3).
Compound 21-3-1: 109.0 DEG C of fusing point.δ(CDCl3): 8.54 (s, 1H, Pyrimidine-H), 7.47 (t, J= 6Hz, 2H, Ph-3,5-2H), 7.420 (t, J=6Hz, 1H, Ph-4-H), 7.31 (d, J=6Hz, 2H, Ph-2,6-2H), 6.85 (s,1H, NH),6.72(t,JHF=54Hz, 1H, CHF2), 4.63-4.65 (m, 1H, N-CH), 4.38 (d, J=6Hz, 2H, O- CH2), 3.61(s,3H,N-CH3),1.86(s,3H,Pyrazole-4-CH3), 1.41 (d, J=6Hz, 3H, CHCH3).
Compound 21-4-1: 149.3 DEG C of fusing point.δ(CDCl3): 8.46 (s, 1H, Pyrimidine-H), 7.46 (t, J= 6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.29 (d, J=6Hz, 2H, Ph-2,6-2H), 7.04 (s, 1H, Thiophene-H), 6.91 (s, 1H, NH), 4.84-4.86 (m, 1H, N-CH), 4.39 (d, J=6Hz, 2H, O- CH2), 3.59(s,3H,N-CH3),1.87(s,3H,Pyrazole-4-CH3), 1.48 (d, J=6Hz, 3H, CHCH3).
Meanwhile corresponding raw material being replaced according to the content recorded in above-mentioned each synthetic example and can be obtained this hair Other compounds shown in bright general formula I.
In addition, above-mentioned acquisition compound is reacted with acid in a conventional manner, and then obtain corresponding salt.
Biological activity determination embodiment
Compound shown in above-mentioned acquisition general formula I of the present invention all shows well the various pests harmful mite in agriculture field Activity is specific:
Pesticide and miticide actility measurement
Insecticidal activity assay test has been carried out to several insects with the compounds of this invention.Measuring method is as follows:
Untested compound acetone/methanol (1:1 (v/v)) mixed solvent dissolution after, with contain 0.1% (wt) Tween 80 Water be diluted to required concentration.
Using black peach aphid, Tetranychus cinnabarinus as target, insecticidal activity assay is carried out using airbrush spray-on process.
(1) determination of activity of black peach aphid is killed
Measuring method: taking diameter 6cm culture dish, and one layer of filter paper is covered at ware bottom, and appropriate tap water moisturizing is added dropwise.From culture peach Clip suitable size (diameter about 3cm) and the cabbage leaves with 15~30 aphids on the cabbage plant of aphid remove alatae And the aphid of face of blade, blade back are placed in culture dish upwards.The pressure of airbrush spraying treatment is that 10 psi (are roughly equal to 0.7kg/cm2), spouting liquid 0.5ml, 3 repetitions of every processing.25 DEG C, 60~70% observation ward of relative humidity are put into after processing Interior culture, investigation survival borer population, calculates the death rate after 48 hours.
Under 600ppm dosage, there are 11-1-1,11-1-4,11-1- in 80% or more compound to the lethality of black peach aphid 19,11-1-57,12-1-57 etc.；
Under 100ppm dosage, there are 11-1-1,11-1-4,12-1- in 80% or more compound to the lethality of black peach aphid 57 etc.；
(2) determination of activity of Tetranychus cinnabarinus is killed
Measuring method: taking two panels true leaf Kidney bean seedling, spraying with airbrush after connecting Tetranychus cinnabarinus adult mite and investigating radix Device carries out whole strain processing, and pressure is that 10psi (is roughly equal to 0.7kg/cm2), spouting liquid 0.5ml.3 repetitions of every processing, after processing It is placed in standard sight room, investigation survival mite number, calculates the death rate after 72 hours.
It is as follows to the partial test result of Tetranychus cinnabarinus:
Under 600ppm dosage, there are 10-1,10-3-1,11- in 80% or more compound to the lethality of Tetranychus cinnabarinus 1、 11-34、11-1-1、11-1-4、11-1-19、11-1-57、11-1-72、11-3-1、12-1、12-1-4、12-1-19、 12-1-57,12-1-72,12-3-1,19-1-19,19-1-57,19-1-72,19-3-1,21-1,21-34,21-1-72 etc.；
Under 100ppm dosage, there are 11-1,11-34,11-1- in 80% or more compound to the lethality of Tetranychus cinnabarinus 1、 11-1-4、11-1-19、11-1-57、11-1-72、11-3-1、12-1-4、12-1-19、12-1-57、12-1-72、12-3- 1,19-1-19,19-1-57,19-1-72,19-3-1,21-1-72 etc.；
Under 10ppm dosage, to the lethality of Tetranychus cinnabarinus 80% or more compound have 11-1,11-1-4,11- 1-19,11-1-57,11-1-72,12-1-4,12-1-19,12-1-57,19-1-19,21-1-72 etc.；
Under 2.5ppm dosage, compound 11-1-4,11-1-19,11-1-57 and 11-1-72 are to the lethal of Tetranychus cinnabarinus Rate is greater than 80%.
Other compounds shown in general formula I of the present invention are surveyed accordingly according to the mode of above-mentioned biological activity determination Examination, can also have corresponding activity.

Claims (10)

1. a kind of substituted pyrazolecarboxylic class compound, it is characterised in that: substituted pyrazolecarboxylic class compound is compound shown in general formula I；
In formula:
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C3-C12Naphthenic base, C1- C12Alkoxy, halogenated C1-C12Alkoxy, C1-C12Alkylthio group, halogenated C1-C12Alkylthio group, C1-C12Alkyl sulphinyl, C1-C12 Alkyl sulphonyl, C2-C12Alkenyl, halogenated C2-C12Alkenyl, C2-C12Alkynyl, halogenated C2-C12Alkynyl, C3-C12It is alkenyloxy group, halogenated C3-C12Alkenyloxy group, C3-C12Alkynyloxy group, halogenated C3-C12Alkynyloxy group, C1-C12Alkyl amino, two (C1-C12Alkyl) amino, C1-C12 Alkyl amino-carbonyl, halogenated C1-C12Alkyl amino-carbonyl, C1-C12Alkoxy carbonyl, halogenated C1-C12Alkoxy carbonyl, C1-C12 Alkoxy C1-C12Alkyl or C1-C2Alkylthio group C1-C12Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alcoxyl Base or halogenated C1-C12Alkoxy；
R1And R2Also five yuan, hexa-atomic, seven yuan or octatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy, halogenated C1-C12Alkoxy, C3-C12Naphthenic base, C1-C12Alkylthio group, C2-C12Enylsulfanyl, C2-C12Alkenyl, C2-C12Alkynyl, halogenated C2-C12It is alkenyl, halogenated C2-C12Alkynyl, C1-C12Alkoxy C1-C12Alkyl, halogenated C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12Alkyl, Halogenated C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkyl sulphinyl, halogenated C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphur Acyl group, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkyl amino sulfonyl, two (C1-C12Alkyl) amino-sulfonyl, C1-C12Alkane Base sulfonyl amino carbonyl, C1-C12Alkyl-carbonyl-amino sulfonyl, C3-C12Cycloalkyloxycarbonyl, C1-C12Alkyl-carbonyl, halogen For C1-C12Alkyl-carbonyl, C1-C12Alkoxy carbonyl, halogenated C1-C12Alkoxy carbonyl, C1-C12Alkyl-carbonyl C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkyl amino-carbonyl, two (C1-C12Alkyl) amino carbonyl, C2-C12Alkenyloxy group Carbonyl, C2-C12Alkynyloxycar bonyl, C1-C12Alkoxy C1-C12Alkoxy carbonyl, C1-C12Alkyl amino sulfenyl, two (C1-C12Alkane Base) amino sulfenyl, the unsubstituted or aryl carbonyl C that are replaced by the following groups of 1-51-C6Alkyl, aryl carbonyl, aryloxy group carbonyl Base, aryl C1-C6Alkyloxycarbonyl, aryl C1-C6Alkyl, Heteroarylcarbonyl C1-C6Alkyl, Heteroarylcarbonyl, heteroaryloxy Carbonyl, heteroaryl C1-C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyl, following group are halogen, nitro, cyano, C1-C6Alkane Base, halogenated C1-C6Alkyl, C1-C6Alkoxy or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy is halogenated C1-C12Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C8Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy is halogenated C1-C12Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C8Ring；
M is selected from 0 to 5 integer；
R8Selected from hydrogen, cyano, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy carbonyl, halogenated C1-C12Alkoxy It is carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl Base, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C12Alkyl, C3-C8Naphthenic base, halogenated C1-C12Alkyl, C1-C12Alkyl-carbonyl, halogenated C1-C12Alkyl oxycarbonyl Base, C1-C12Alkyl sulphonyl, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl Carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12It is alkoxy, halogenated C1-C12Alkoxy, C3-C12Naphthenic base, C1-C12Alkyl amino, halogenated C1-C12Alkyl amino, two (C1-C12Alkyl) amino, halogen Two (C of generation1-C12Alkyl) amino, C (=O) NR11R12、C1-C12Alkylthio group, halogenated C1-C12Alkylthio group, C2-C12Alkenyl, C2-C12 Alkynyl, C2-C12Alkenyloxy group, halogenated C2-C12Alkenyloxy group, C2-C12Alkynyloxy group, halogenated C2-C12Alkynyloxy group, C1-C12Alkyl sulphonyl, Halogenated C1-C12Alkyl sulphonyl, C1-C12Alkyl-carbonyl, halogenated C1-C12Alkyl-carbonyl, C1-C12Alkoxy carbonyl, halogenated C1-C12 Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl, halogenated C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12Alkane Base, halogenated C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, halogenated C1-C12Alkoxy carbonyl C1-C12 Alkyl, C1-C12Alkylthiocarbonyl C1-C12Alkyl, halogenated C1-C12Alkylthiocarbonyl C1-C12Alkyl, C1-C12Alkyl carbonyl epoxide, Halogenated C1-C12Alkyl carbonyl epoxide, C1-C12Alkoxy-carbonyl oxy, halogenated C1-C12Alkoxy-carbonyl oxy, C1-C12Alkyl sulphur Acyloxy, halogenated C1-C12Alkyl sulphonyl oxygroup, C1-C12Alkoxy C1-C12Alkoxy or halogenated C1-C12Alkoxy C1-C12 Alkoxy；
N is selected from 0 to 5 integer；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C3-C8Naphthenic base, C1-C12Alkoxy, C1-C12Alkylthio group or C1-C12Alkyl sulphonyl；
Or the salt of compound shown in general formula I.
2. substituted pyrazolecarboxylic class compound according to claim 1, it is characterised in that: in compound of Formula I
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Naphthenic base, C1-C6 Alkoxy, halogenated C1-C6Alkoxy, C1-C6Alkylthio group, C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkane Sulfenyl, C2-C6Alkenyl, halogenated C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6Alkynyl, C3-C6Alkenyloxy group, halogenated C3-C6Alkenyloxy group, C3-C6Alkynyloxy group, halogenated C3-C6Alkynyloxy group, C1-C6Alkyl amino, two (C1-C6Alkyl) amino, C1-C6Alkyl amino-carbonyl, halogen For C1-C6Alkyl amino-carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkoxy C1-C6Alkyl or C1- C6Alkylthio group C1-C6Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy Or halogenated C1-C6Alkoxy；
R1And R2Also five yuan or hexatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy, halogenated C1-C6Alkoxy, C3- C6Naphthenic base, C1-C6Alkylthio group, C2-C6Enylsulfanyl, C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6Alkenyl, halogenated C2-C6Alkynes Base, C1-C6Alkoxy C1-C6Alkyl, halogenated C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group C1-C6Alkyl, halogenated C1-C6Alkane Sulfenyl C1-C6Alkyl, C1-C6Alkyl sulphinyl, halogenated C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halogenated C1-C6 Alkyl sulphonyl, C1-C6Alkyl amino sulfonyl, two (C1-C6Alkyl) amino-sulfonyl, C1-C6Alkylsulfonyl aminocarbonyl, C1-C6Alkyl-carbonyl-amino sulfonyl, C3-C6Cycloalkyloxycarbonyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl-carbonyl, C1- C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkyl-carbonyl C1-C6Alkyl, C1-C6Alkoxy carbonyl C1-C6Alkyl, C1-C6Alkyl amino-carbonyl, two (C1-C6Alkyl) amino carbonyl, C2-C6Allyloxycarbonyl, C2-C6Alkynyloxycar bonyl, C1-C6Alkane Oxygroup C1-C6Alkoxy carbonyl, C1-C6Alkyl amino sulfenyl, two (C1-C6Alkyl) amino sulfenyl, it is unsubstituted or by 1-5 such as The aryl carbonyl C that lower group is further substituted with1-C6Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C6Alkyloxycarbonyl, Aryl C1-C6Alkyl, Heteroarylcarbonyl C1-C6Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C6Alkyl oxy carbonyl Base, heteroaryl C1-C6Alkyl, following group are halogen, nitro, cyano, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy Or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy is halogenated C1-C6Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C6Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy is halogenated C1-C6Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C6Ring；
M is selected from 0 to 4 integer；
R8Selected from hydrogen, cyano, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl It is base, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl Base, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C6Alkyl, C3-C6Naphthenic base, halogenated C1-C6Alkyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl-carbonyl, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkyl sulphonyl, C1-C6Alkoxy carbonyl, C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkane Epoxide carbonyl C1-C6It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, virtue Epoxide carbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy, halogenated C1-C6 Alkoxy, C3-C6Naphthenic base, C1-C6Alkyl amino, halogenated C1-C6Alkyl amino, two (C1-C6Alkyl) amino, halogenated two (C1- C6Alkyl) amino, C (=O) NR11R12、C1-C6Alkylthio group, halogenated C1-C6Alkylthio group, C2-C6Alkenyl, C2-C6Alkynyl, C2-C6Alkene Oxygroup, halogenated C2-C6Alkenyloxy group, C2-C6Alkynyloxy group, halogenated C2-C6Alkynyloxy group, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkyl sulphur Acyl group, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkane Oxygroup C1-C6Alkyl, halogenated C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group C1-C6Alkyl, halogenated C1-C6Alkylthio group C1-C6Alkane Base, C1-C6Alkoxy carbonyl C1-C6Alkyl, halogenated C1-C6Alkoxy carbonyl C1-C6Alkyl, C1-C6Alkylthiocarbonyl C1-C6Alkane Base, halogenated C1-C6Alkylthiocarbonyl C1-C6Alkyl, C1-C6Alkyl carbonyl epoxide, halogenated C1-C6Alkyl carbonyl epoxide, C1-C6Alkane Epoxide carbonyl oxygroup, halogenated C1-C6Alkoxy-carbonyl oxy, C1-C6Alkyl sulphonyl oxygroup, halogenated C1-C6Alkyl sulphonyl oxygen Base, C1-C6Alkoxy C1-C6Alkoxy or halogenated C1-C6Alkoxy C1-C6Alkoxy；
N is selected from 0 to 5 integer；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Naphthenic base, C1-C6Alkoxy, C1-C6Alkylthio group or C1- C6Alkyl sulphonyl.
3. in substituted pyrazolecarboxylic class compound according to claim 2, it is characterised in that: in general formula I
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4 Alkoxy, halogenated C1-C4Alkoxy, C1-C4Alkylthio group, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkane Sulfenyl, C2-C4Alkenyl, halogenated C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkynyl, C3-C4Alkenyloxy group, halogenated C3-C4Alkenyloxy group, C3-C4Alkynyloxy group, halogenated C3-C4Alkynyloxy group, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl amino-carbonyl, halogen For C1-C4Alkyl amino-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkyl or C1- C4Alkylthio group C1-C4Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy Or halogenated C1-C4Alkoxy；
R1And R2Also five yuan or hexatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alkoxy, C3- C4Naphthenic base, C1-C4Alkylthio group, C2-C4Enylsulfanyl, C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkenyl, halogenated C2-C4Alkynes Base, C1-C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkane Sulfenyl C1-C4Alkyl, C1-C4Alkyl sulphinyl, halogenated C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogenated C1-C4 Alkyl sulphonyl, C1-C4Alkyl amino sulfonyl, two (C1-C4Alkyl) amino-sulfonyl, C1-C4Alkylsulfonyl aminocarbonyl, C1-C4Alkyl-carbonyl-amino sulfonyl, C3-C4Cycloalkyloxycarbonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1- C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, C2-C4Allyloxycarbonyl, C2-C4Alkynyloxycar bonyl, C1-C4Alkane Oxygroup C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or by 1-5 such as The aryl carbonyl C that lower group is further substituted with1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkyloxycarbonyl, Aryl C1-C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C4Alkyl oxy carbonyl Base, heteroaryl C1-C4Alkyl, following group are halogen, nitro, cyano, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy Or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy is halogenated C1-C4Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C4Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy is halogenated C1-C4Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C4Ring；
M is selected from 0 to 3 integer；
R8Selected from hydrogen, cyano, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl It is base, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl Base, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C4Alkyl, C3-C4Naphthenic base, halogenated C1-C4Alkyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkyl sulphonyl, C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkane Epoxide carbonyl C1-C4It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, virtue Epoxide carbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4 Alkoxy, C3-C4Naphthenic base, C1-C4Alkyl amino, halogenated C1-C4Alkyl amino, two (C1-C4Alkyl) amino, halogenated two (C1- C4Alkyl) amino, C (=O) NR12R13、C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C2-C4Alkenyl, C2-C4Alkynyl, C2-C4Alkene Oxygroup, halogenated C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halogenated C2-C4Alkynyloxy group, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkyl sulphur Acyl group, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkane Oxygroup C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkylthio group C1-C4Alkane Base, C1-C4Alkoxy carbonyl C1-C4Alkyl, halogenated C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkylthiocarbonyl C1-C4Alkane Base, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4Alkane Epoxide carbonyl oxygroup, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphonyl oxygen Base, C1-C4Alkoxy C1-C4Alkoxy or halogenated C1-C4Alkoxy C1-C4Alkoxy；
N is selected from 0 to 5 integer；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, C1-C4Alkylthio group or C1- C4Alkyl sulphonyl.
4. substituted pyrazolecarboxylic class compound according to claim 3, it is characterised in that: compound shown in the general formula I-1 Structure are as follows: I-A, I-B, I-C, I-D；
In formula:
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy is halogenated C1-C4Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C4Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy is halogenated C1-C4Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C4Ring；
M is selected from 0 to 3 integer；
R8、R9Identical or different is respectively selected from hydrogen, cyano, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy carbonyl Base, halogenated C1-C4It is alkoxy carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl Base, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4 Alkoxy, C3-C4Naphthenic base, C1-C4Alkyl amino, halogenated C1-C4Alkyl amino, two (C1-C4Alkyl) amino, halogenated two (C1- C4Alkyl) amino, C (=O) NR11R12、C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C2-C4Alkenyl, C2-C4Alkynyl, C2-C4Alkene Oxygroup, halogenated C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halogenated C2-C4Alkynyloxy group, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkyl sulphur Acyl group, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkane Oxygroup C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkylthio group C1-C4Alkane Base, C1-C4Alkoxy carbonyl C1-C4Alkyl, halogenated C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkylthiocarbonyl C1-C4Alkane Base, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4Alkane Epoxide carbonyl oxygroup, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphonyl oxygen Base, C1-C4Alkoxy C1-C4Alkoxy or halogenated C1-C4Alkoxy C1-C4Alkoxy；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It is identical or different；
R11、R12Identical or different is respectively selected from hydrogen, C1-C4Alkyl or halogenated C1-C4Alkyl；
W is selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, C1-C4Alkylthio group or C1- C4Alkyl sulphonyl；
And when the compound is general formula I-D, X is O or S；
When the compound is general formula I-A and I-D,
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4 Alkoxy, halogenated C1-C4Alkoxy, C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphur Acyl group, C2-C4Alkenyl, halogenated C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkynyl, C3-C4Alkenyloxy group, halogenated C3-C4Alkenyloxy group, C3-C4Alkynyloxy group, halogenated C3-C4Alkynyloxy group, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl amino-carbonyl, halogen For C1-C4Alkyl amino-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkyl or C1- C4Alkylthio group C1-C4Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy Or halogenated C1-C4Alkoxy；
When the compound is general formula I-A, I-B and I-C,
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alkoxy, C3- C4Naphthenic base, C1-C4Alkylthio group, C2-C4Enylsulfanyl, C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkenyl, halogenated C2-C4Alkynes Base, C1-C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkane Sulfenyl C1-C4Alkyl, C1-C4Alkyl sulphinyl, halogenated C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogenated C1-C4 Alkyl sulphonyl, C1-C4Alkyl amino sulfonyl, two (C1-C4Alkyl) amino-sulfonyl, C1-C4Alkylsulfonyl aminocarbonyl, C1-C4Alkyl-carbonyl-amino sulfonyl, C3-C4Cycloalkyloxycarbonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1- C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, C2-C4Allyloxycarbonyl, C2-C4Alkynyloxycar bonyl, C1-C4Alkane Oxygroup C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or by 1-5 such as The aryl carbonyl C that lower group is further substituted with1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkyloxycarbonyl, Aryl C1-C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C4Alkyl oxy carbonyl Base, heteroaryl C1-C4Alkyl, following group are halogen, nitro, cyano, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy Or halogenated C1-C4Alkoxy；
When the compound is general formula I-B,
R13、R14、R15Or R16Identical or different is respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4Alkyl, halogen For C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alkoxy or C3-C4Naphthenic base；
When the compound is general formula I-C,
R17、R18Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4It is alkoxy, halogenated C1-C4Alkoxy, C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C3-C4It is naphthenic base, unsubstituted or by 1-5 R10Substituted virtue Base, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl Carbonyl or Heteroaryloxycarbonyl.
5. substituted pyrazolecarboxylic class compound according to claim 4, it is characterised in that: shown in general formula I-A, I-B, I-C, I-D In compound:
R4、R5The identical or different hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, normal-butyl, secondary of being respectively selected from Butyl, isobutyl group, tert-butyl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy Or tert-butoxy；
R6、R7The identical or different hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, normal-butyl, secondary of being respectively selected from Butyl, isobutyl group, tert-butyl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy Or tert-butoxy；
R8、R9Identical or different is respectively selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, different Butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, one methyl fluoride of dichloro, methoxyl group, ethyoxyl, positive third oxygen Base, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methyl mercapto, ethylmercapto group, trifluoromethoxy, trifluoro Ethyoxyl, methoxycarbonyl, ethoxy carbonyl, amino carbonyl, methylaminocarbonyl, ethyl aminocarbonyl or dimethylamino carbonyl Base；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It may be the same or different；
W be selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tert-butyl, One methyl fluoride, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, methyl mercapto, ethylmercapto group, methyl Sulfonyl or ethylsulfonyl；
And when the compound is general formula I-A and I-D,
R1Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, carboxyl, methyl, ethyl, n-propyl, isopropyl, normal-butyl, secondary Butyl, isobutyl group, tert-butyl, a methyl fluoride, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy, second Oxygroup methyl or trifluoroethoxy ylmethyl；
R2Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, carboxyl, formoxyl, methyl, ethyl, methoxyl group, ethyoxyl or Trifluoro ethoxy；
When the compound is general formula I-A, I-B and I-C,
R3Selected from hydrogen, hydroxyl, formoxyl, acetyl group, propiono, bytyry, trifluoroacetyl group, benzoyl, methyl, ethyl, just Propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tert-butyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, trifluoro Ethyoxyl, cyclopropyl oxygroup, methyl mercapto, ethylmercapto group, allyl, propargyl, mesyl, ethylsulfonyl, trifluoroethyl sulphonyl Base, aminosulfonyl, ethylamino sulfonyl, dimethylaminosulfonyl, lignocaine sulfonyl, methane sulfonylamino carbonyl, Methoxycarbonyl, ethoxy carbonyl, propoxycarbonyl, isopropoxy carbonyl, amino-carbonyl, dimethyl-aminocarbonyl, ethylene oxy Base carbonyl, acetylene Epoxide carbonyl, methylamino sulfenyl, ethylamino sulfenyl or dimethylamino sulfenyl；
When the compound is general formula I-B,
R13、R14、R15Or R16It is identical or different be respectively selected from hydrogen, fluorine, chlorine, bromine, iodine, amino, cyano, nitro, methyl, ethyl, N-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, dichloro One methyl fluoride, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, Trifluoromethoxy or trifluoro ethoxy；
When the compound is general formula I-C,
R17、R18The identical or different hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, normal-butyl, secondary of being respectively selected from Butyl, isobutyl group, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, one methyl fluoride of dichloro, trifluoroethyl, methoxy Base, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, three It is fluorine ethyoxyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, Heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl.
6. substituted pyrazolecarboxylic class compound according to claim 5, it is characterised in that: shown in general formula I-A, I-B, I-C, I-D In compound:
R4、R5Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine or methyl；
R6、R7It is selected from hydrogen；
R8For hydrogen or methyl；
R9Selected from hydrogen or methyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxyl group, methyl mercapto or trifluoromethoxy；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl；
And when the compound is general formula I-A and I-D,
R1Selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or difluoromethyl；
R2Selected from hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, formoxyl, methyl, ethyl, methoxy or ethoxy；
When the compound is general formula I-A, I-B and I-C,
R3Selected from hydrogen, methyl, acetyl group, trifluoroacetyl group, methoxyl group, methyl mercapto, allyl, mesyl, methylamino sulphonyl Base, dimethylaminosulfonyl, methoxycarbonyl, amino-carbonyl, dimethyl-aminocarbonyl, methylamino sulfenyl or dimethylamino sulphur Base；
When the compound is general formula I-B,
R13、R14、R15Or R16Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl；
When the compound is general formula I-C,
R17、R18Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine or iodine.
7. substituted pyrazolecarboxylic class compound according to claim 6, it is characterised in that: shown in general formula I-A, I-B, I-C, I-D In compound:
R4、R5It may be the same or different, be respectively selected from hydrogen or methyl；
R6、R7It is selected from hydrogen；
R8For hydrogen or methyl；
R9Selected from methyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxyl group, methyl mercapto or trifluoromethoxy；
N is selected from 1 to 5 integer, when n is greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine or iodine；
And when the compound is general formula I-A and I-D,
R1Selected from fluorine, chlorine, bromine, iodine, methyl, ethyl or difluoromethyl；
R2Selected from fluorine, chlorine, bromine, iodine, nitro, amino, formoxyl, methyl or methoxy；
When the compound is general formula I-A, I-B and I-C,
R3Selected from hydrogen, methyl, acetyl group, methoxyl group, allyl, mesyl, methoxycarbonyl, amino-carbonyl, dimethylamino Carbonyl or dimethylamino sulfenyl；
When the compound is general formula I-B,
R13、R14、R15、R16It is selected from hydrogen；
When the compound is general formula I-C,
R17Selected from hydrogen；
R18Selected from chlorine.
8. one kind is by substituted pyrazolecarboxylic class compound described in claim 1, it is characterised in that: the preparation side of compound shown in general formula I Method are as follows:
9. a kind of use in agricultural or other field according to substituted pyrazolecarboxylic class compound described in any one of claim 1-7 Prepare the purposes of insecticidal/acaricidal agent drug.
10. a kind of insecticide acaricide composition, it is characterised in that: contain the substitution pyrrole as described in any one of claim 1-7 Azole compounds are as active component；Wherein, the weight percentage of active component is 0.1-99% in composition.
CN201711223553.3A 2017-11-29 2017-11-29 Substituted pyrazolecarboxylic class compound and preparation method thereof and purposes as insecticidal/acaricidal agent Pending CN109836418A (en)

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US16/766,925 US11457628B2 (en) 2017-11-29 2018-11-22 Substituted pyrimidine compound and preparation method and use thereof
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PCT/CN2018/116938 WO2019105275A1 (en) 2017-11-29 2018-11-22 Substituted pyrimidine compound and preparation method therefor and use thereof
BR112020010921-5A BR112020010921B1 (en) 2017-11-29 2018-11-22 SUBSTITUTED PYRIMIDINE COMPOUND AND METHOD OF PREPARATION FOR IT AND ITS USE
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