CN108059629A - Substituted pyrazolecarboxylic class compound containing pyrimidine and its preparation method and application - Google Patents

Substituted pyrazolecarboxylic class compound containing pyrimidine and its preparation method and application Download PDF

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CN108059629A
CN108059629A CN201610978801.4A CN201610978801A CN108059629A CN 108059629 A CN108059629 A CN 108059629A CN 201610978801 A CN201610978801 A CN 201610978801A CN 108059629 A CN108059629 A CN 108059629A
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alkyl
halogenated
carbonyl
alkoxy
amino
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CN108059629B (en
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关爱莹
杨金龙
李志念
许磊川
王军锋
孙旭峰
刘长令
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

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Abstract

The invention discloses a kind of substituted pyrazolecarboxylic class compounds containing pyrimidine, and structure is as shown in general formula I：

Description

Substituted pyrazolecarboxylic class compound containing pyrimidine and its preparation method and application
Technical field
The invention belongs to chemical fields, and in particular to a kind of substituted pyrazolecarboxylic class compound containing pyrimidine and preparation method thereof and use On the way.
Background technology
Patent WO9507278 discloses the substituted pyrazolecarboxylic class compound formula containing pyrimidine and materialization shown in below formula Close object CK1 and CK2, the application as agricultural bactericidal, Insecticidal and acaricidal agent etc..
Through Scifinder online information retrievals to following compound CK3, CK4, CK5, but without particular reference.
But substituted pyrazolecarboxylic class compound containing pyrimidine of the structure as shown in general formula I of the present invention has not been reported.
The content of the invention
It is an object of the invention to provide a kind of substituted pyrazolecarboxylic class compound containing pyrimidine that can control a variety of germs and Its preparation method and the purposes for preparing the drug of anti-pathogen 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 containing pyrimidine, and the substituted pyrazolecarboxylic class compound containing pyrimidine is The compound as shown in general formula I,
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 R2Five yuan, hexa-atomic, seven yuan or octatomic ring containing C, N, O or S can also 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-C12Cycloalkyl, 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-C12Alkane Base, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkyl amino-carbonyl, two (C1-C12Alkyl) amino carbonyl, C2-C12Alkene oxygen Base carbonyl, C2-C12Alkynyloxycar bonyl, C1-C12Alkoxy C1-C12Alkoxy carbonyl, C1-C12Alkyl amino sulfenyl, two (C1-C12 Alkyl) amino sulfenyl, the unsubstituted or aryl carbonyl C that are substituted by the following groups of 1-51-C6Alkyl, aryl carbonyl, aryloxy group Carbonyl, aryl C1-C6Alkyloxycarbonyl, aryl C1-C6Alkyl, Heteroarylcarbonyl C1-C6Alkyl, Heteroarylcarbonyl, heteroaryl oxygen Base carbonyl, heteroaryl C1-C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyl, following group is 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 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-C8Cycloalkyl, halogenated C1-C12Alkyl, C1-C12Alkyl-carbonyl, halogenated C1-C12Alkane Base carbonyl, C1-C12Alkyl sulphonyl, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkane Base, C1-C12Alkoxy carbonyl C1-C12It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, virtue Methyl 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-C12Cycloalkyl, 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-carbonyl Oxygroup, halogenated C1-C12Alkyl carbonyl epoxide, C1-C12Alkoxy-carbonyl oxy, halogenated C1-C12Alkoxy-carbonyl oxy, C1-C12 Alkyl sulphonyl oxygroup, halogenated C1-C12Alkyl sulphonyl oxygroup, C1-C12Alkoxy C1-C12Alkoxy or halogenated C1-C12Alcoxyl Base C1-C12Alkoxy；
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-C8Cycloalkyl, C1-C12Alkoxy, C1-C12Alkane sulphur Base or C1-C12Alkyl sulphonyl；
Q is selected from unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxy group carbonyl Base, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
Or the salt of compound shown in general formula I.
It is above-mentioned, R9With in Q compared with R10Substituent group selection it is each independent.
In substituted pyrazolecarboxylic class compound of the present invention containing pyrimidine, optional compound includes：In shown general formula I：
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Cycloalkyl, 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 R2Five yuan or hexatomic ring containing C, N, O or S can also 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-C6Cycloalkyl, 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 oxycarbonyl Base, 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-C6Alkoxy C1-C6Alkoxy carbonyl, C1-C6Alkyl amino sulfenyl, two (C1-C6Alkyl) amino sulfenyl, it is unsubstituted or by The aryl carbonyl C that 1-5 following groups are further substituted with1-C6Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C6Alkyl oxygen Base carbonyl, aryl C1-C6Alkyl, Heteroarylcarbonyl C1-C6Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C6Alkane Base Epoxide carbonyl, heteroaryl C1-C6Alkyl, following group is 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 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-C6Alcoxyl It is base carbonyl, unsubstituted or by 1-5 R10It is substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, miscellaneous Aryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C6Alkyl, C3-C6Cycloalkyl, 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 Base, 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-C6Cycloalkyl, 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-C6 Alkyl, halogenated C1-C6Alkylthiocarbonyl C1-C6Alkyl, C1-C6Alkyl carbonyl epoxide, halogenated C1-C6Alkyl carbonyl epoxide, C1-C6 Alkoxy-carbonyl oxy, halogenated C1-C6Alkoxy-carbonyl oxy, C1-C6Alkyl sulphonyl oxygroup, halogenated C1-C6Alkyl sulphonyl Oxygroup, C1-C6Alkoxy C1-C6Alkoxy or halogenated C1-C6Alkoxy C1-C6Alkoxy；
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-C6Cycloalkyl, C1-C6Alkoxy, C1-C6Alkylthio group Or C1-C6Alkyl sulphonyl；
Q is selected from unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxy group carbonyl Base, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl.
In substituted pyrazolecarboxylic class compound of the present invention containing pyrimidine, more optional compound includes, and Q is selected in the general formula I From unsubstituted or by 1-5 R10Substituted aryl, the structural formula of compound formula I is further as shown in I-1；
In formula,
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Cycloalkyl, 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 R2Five yuan or hexatomic ring containing C, N, O or S can also 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-C4Cycloalkyl, 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 oxycarbonyl Base, 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-C4Alkoxy C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or by The aryl carbonyl C that 1-5 following groups are further substituted with1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkyl oxygen Base carbonyl, aryl C1-C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C4Alkane Base Epoxide carbonyl, heteroaryl C1-C4Alkyl, following group is 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 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-C4Alcoxyl It is base carbonyl, unsubstituted or by 1-5 R10It is substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, miscellaneous Aryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C4Alkyl, C3-C4Cycloalkyl, 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-C4Cycloalkyl, 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-C4 Alkyl, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4 Alkoxy-carbonyl oxy, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphonyl Oxygroup, C1-C4Alkoxy C1-C4Alkoxy or halogenated C1-C4Alkoxy C1-C4Alkoxy；
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-C4Cycloalkyl, C1-C4Alkoxy, C1-C4Alkylthio group Or C1-C4Alkyl sulphonyl.
In substituted pyrazolecarboxylic class compound of the present invention containing pyrimidine, further alternative compound includes, the general formula I-1 institutes The structure for showing compound is：I-1A、I-1B、I-1C、I-1D；
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-C4Cycloalkyl, 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-C4 Alkyl, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4 Alkoxy-carbonyl oxy, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphonyl Oxygroup, 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 more 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-C4Cycloalkyl, C1-C4Alkoxy, C1-C4Alkylthio group Or C1-C4Alkyl sulphonyl；
And when the compound is general formula I-1D, X is O or S；
When the compound is general formula I-1A and I-1D,
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Cycloalkyl, 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-1A, I-1B and I-1C,
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alcoxyl Base, C3-C4Cycloalkyl, 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 oxycarbonyl Base, 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-C4Alkoxy C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or by The aryl carbonyl C that 1-5 following groups are further substituted with1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkyl oxygen Base carbonyl, aryl C1-C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C4Alkane Base Epoxide carbonyl, heteroaryl C1-C4Alkyl, following group is halogen, nitro, cyano, C1-C4Alkyl, halogenated C1-C4Alkyl, C1- C4Alkoxy or halogenated C1-C4Alkoxy；
When the compound is general formula I-1B,
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-C4Cycloalkyl；
When the compound is general formula I-1C,
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 cycloalkyl, unsubstituted or by 1-5 R10Substitution Aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroaryl Methyl carbonyl or Heteroaryloxycarbonyl；
In substituted pyrazolecarboxylic class compound of the present invention containing pyrimidine, further optional compound includes, general formula I-1A, I- In compound shown in 1B, I-1C, I-1D：
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, tertiary 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, tertiary 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, tertiary 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 more 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-1A and I-1D,
R1Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, carboxyl, methyl, ethyl, n-propyl, isopropyl, positive fourth Base, sec-butyl, isobutyl group, tertiary 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-1A, I-1B and I-1C,
R3Selected from hydrogen, hydroxyl, formoxyl, acetyl group, propiono, bytyry, trifluoroacetyl group, benzoyl, methyl, second Base, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, Trifluoro ethoxy, cyclopropyl oxygroup, methyl mercapto, ethylmercapto group, pi-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-1B,
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, tertiary 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-1C,
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, tertiary 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；
In substituted pyrazolecarboxylic class compound of the present invention containing pyrimidine, further optional compound includes, general formula I-1A, I- In compound shown in 1B, I-1C, I-1D：
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 more 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-1A and I-1D,
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-1A, I-1B and I-1C,
R3Selected from hydrogen, methyl, acetyl group, trifluoroacetyl group, methoxyl group, methyl mercapto, pi-allyl, mesyl, methylamino Sulfonyl, dimethylaminosulfonyl, methoxycarbonyl, amino-carbonyl, dimethyl-aminocarbonyl, methylamino sulfenyl or dimethylamino Sulfenyl；
When the compound is general formula I-1B,
R13、R14、R15Or R16Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl；
When the compound is general formula I-1C,
R17、R18Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine or iodine；
In substituted pyrazolecarboxylic class compound of the present invention containing pyrimidine, more optional compound includes,：General formula I-1A, I-1B, I- In compound shown in 1C, I-1D：
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 more 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-1A and I-1D,
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-1A, I-1B and I-1C,
R3Selected from hydrogen, methyl, acetyl group, methoxyl group, pi-allyl, mesyl, methoxycarbonyl, amino-carbonyl, two Amino-carbonyl or dimethylamino sulfenyl；
When the compound is general formula I-1B,
R13、R14、R15、R16It is selected from hydrogen；
When the compound is general formula I-1C,
R17Selected from hydrogen；
R18Selected from chlorine；
A kind of preparation method of the substituted pyrazolecarboxylic class compound containing pyrimidine, the preparation method of compound is shown in general formula I：
A kind of substituted pyrazolecarboxylic class compound containing pyrimidine shown in above-mentioned general formula I is used as preparing in agricultural or other field The purposes of fungicide drug.
A kind of bactericidal composition, the substituted pyrazolecarboxylic class compound containing pyrimidine shown in composition using above-mentioned general formula I is as living Property component；Wherein, the weight percentage of active component is 0.1-99% in composition.
In the definition of compound of Formula I given above, collect term used and be generally defined as follows：
Halogen：Refer to fluorine, chlorine, bromine or iodine.Alkyl：Straight or branched alkyl, such as methyl, ethyl, propyl, isopropyl, just Butyl or tertiary butyl.Cycloalkyl：Substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopenta or cyclohexyl.Substituent group is such as Methyl, halogen etc..Halogenated alkyl：Straight or branched alkyl, the hydrogen atom on these alkyl can be partly or entirely by halogen atom Substituted, for example, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl etc..Alkyl sulphinyl： Straight or branched alkyl is connected to through sulfinyl (- SO-) in structure, such as methylsulfinyl.Alkylsulfinyl：Directly Chain or branched alkyl sulfinyl, the hydrogen atom on alkyl can partly or entirely be substituted by halogen atom.Halogenated alkyl sulphonyl Base：Straight or branched alkyl sulfonyl, the hydrogen atom on alkyl can partly or entirely be substituted by 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：Alkane Base-S (O)2-O-.Halogenated alkyl sulfonyl oxygroup：Hydrogen atom on the alkyl of alkyl sulphonyl oxygroup can be partly or entirely by halogen Atom is substituted, such as CF3-SO2-O.Cycloalkyloxycarbonyl：Such as ring propoxycarbonyl, cyclohexyloxy carbonyl.Alkoxy： Straight or branched alkyl, through in oxygen atom key connection to structure.Halogenated alkoxy：Straight or branched alkoxyl, in these alcoxyls Hydrogen atom on base can partly or entirely be substituted by halogen atom.For example, chloromethane oxygroup, dichloro methoxyl group, trichloromethoxy, fluorine Methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group, trifluoro ethoxy etc..Halo alkoxy carbonyl：Alkoxy carbonyl Hydrogen atom on the alkyl of base can partly or entirely be substituted by halogen atom, such as ClCH2CH2OCO-、CF3CH2OCO- etc..Alcoxyl Base alkyl：Alkyl-O- alkyl-, such as CH3OCH2-.Halogenated alkoxy alkyl：Hydrogen atom on the alkyl of alkoxyalkyl can portion Divide or all substituted by halogen atom, such as ClCH2CH2OCH2-、CF3CH2OCH2- etc..Alkoxy carbonyl alkyl：Alkoxy carbonyl- Alkyl-, such as CH3OCOCH2-.Halo alkoxy carbonyl alkyl：Hydrogen atom on the alkyl of alkoxy carbonyl alkyl can part or All substituted by halogen atom, such as CF3CH2OCOCH2-.Alkyl carbonyl epoxide：Such as CH3COO- etc..Halogenated alkyl carbonyl oxygen Base：The hydrogen atom of alkyl carbonyl epoxide can partly or entirely be substituted by halogen atom, such as CF3COO- etc..Alkoxy-carbonyl oxy： Alkoxy carbonyl-oxygroup-, such as CH3OCOO-.Halo alkoxy carbonyl oxygroup：Hydrogen on the alkyl of alkoxy-carbonyl oxy is former Son can partly or entirely be substituted by halogen atom, such as CF3OCOO-.Alkylthiocarbonyl alkyl：Alkylthiocarbonyl-alkyl-, example Such as CH3SCOCH2-.Halogenated alkylthio carbonylic alkyl：Hydrogen atom on the alkyl of alkylthiocarbonyl alkyl can be partly or entirely by halogen Atom is substituted, such as CF3CH2SCOCH2-.Alkyloxy-alkoxy：Such as CH3OCH2O- etc..Halogenated alkoxy alkoxy：Alkoxy On hydrogen atom can partly or entirely be substituted by halogen atom, such as CF3OCH2O-.Alkoxyalkoxycarbonyl：Such as CH3OCH2CH2OCO- etc..Alkylthio group：Straight or branched alkyl, through in sulphur atom key connection to structure.Halogenated alkylthio：Straight chain Or branched alkylthio, the hydrogen atom on these alkyl can partly or entirely be substituted by 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：Hydrogen atom on the alkyl of alkylthio alkyl can be part or all of Substituted by halogen atom, such as ClCH2CH2SCH2-、CF3CH2SCH2- etc..Alkyl amino：Straight or branched alkyl, through nitrogen-atoms key It is connected in structure.Haloalkylamino：Straight or branched alkyl amino, the hydrogen atom on these alkyl can be part or all of Substituted by halogen atom.Dialkyl amido：Such as (CH3)2N-, (CH3CH2)2N-.Halogenated dialkyl amido：Hydrogen atom on alkyl Can partly or entirely it be substituted by halogen atom, such as (CF3)2N-, (CF3CH2)2N-.Alkenyl：Linear chain or branch chain alkenes, such as ethylene Base, 1- acrylic, 2- acrylic and different cyclobutenyls, pentenyl and hexenyl isomers.Alkenyl further includes polyenoid class, and such as 1, 2- allene base and 2,4- hexadienyls.Halogenated alkenyl：Linear chain or branch chain alkenes, hydrogen atom on these alkenyls can part or All substituted by halogen atom.Alkenyloxy group：Linear chain or branch chain alkenes, through in oxygen atom key connection to structure.Haloalkenyloxy：Directly Chain or branch alkenyloxy, the hydrogen atom in these alkenyloxy groups can partly or entirely be substituted by halogen atom.Enylsulfanyl：Straight chain Or branch chain alkene, through in sulphur atom key connection to structure.Such as CH2=CHCH2S-.Allyloxycarbonyl：Such as CH2=CHCH2OCO- Deng.Alkynyl：Linear chain or branch chain acetylenic, for example, acetenyl, 1- propinyls, 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 alkynyls.Halo alkynyl：Linear chain or branch chain Acetylenic, the hydrogen atom on these alkynyls can partly or entirely be substituted by halogen atom.Alkynyloxy group：Linear chain or branch chain acetylenic, warp Oxygen atom key connection is in structure.Halogenated alkynyloxy group：Linear chain or branch chain alkynyloxy group, the hydrogen atom on these alkynyloxy groups can part Or all substituted by halogen atom.Alkynyloxycar bonyl：Such as CH ≡ CCH2OCO- etc..Alkyl sulphonyl：Straight or branched alkyl passes through Sulfonyl (- SO2-) be connected in structure, such as methyl sulphonyl.Halogenated alkyl sulfonyl：Straight or branched alkyl sulfonyl, Hydrogen atom on alkyl can partly or entirely be substituted by halogen atom.Alkyl-carbonyl：Alkyl is connected to through carbonyl in structure, such as CH3CO-, CH3CH2CO-.Halogenated alkyl carbonyl：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 to through carbonyl in structure.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 moiety in aryl alkyl carbonyl, (miscellaneous) aryloxycarbonyl, (miscellaneous) aryl alkyl Epoxide carbonyl is including phenyl or naphthyl etc.. Heteroaryl is containing the heteroatomic five-membered ring of one or more N, O, S or hexatomic ring.Such as furyl, pyrazolyl, thiazolyl, pyridine Base, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, quinolyl etc..(miscellaneous) aryl：Such as phenyl.(miscellaneous) aryl alkyl：Such as benzene first Base, phenethyl, to chlorophenylmethyl, 2- chloropyridine -5- bases, the chloro- thiazole -5- bases of 2- etc..(miscellaneous) aryl carbonyl：As benzoyl, 4- chlorobenzene formacyls etc..(miscellaneous) arylmethyl carbonyl：Such as PhCH2CO-.(miscellaneous) aryl alkyl carbonyl：Such as PhCOCH2-.(miscellaneous) virtue oxygen Base carbonyl：Such as phenyloxycarbonyl, 4- cHorophenoxycarbonyls, 4-nitrophenoxy carbonyl, naphthoxycarbonyl.Aryl alkyl oxygroup Carbonyl：Such as benzyloxycarbonyl, 4- chlorobenzyls Epoxide carbonyl, 4- trifluoromethyl benzyl Epoxide carbonyls.(miscellaneous) aryl alkyl oxygen Base 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
Table 7R9Substituent group
Table 8W substituent groups
The part of compounds of the present 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-1A, I-1B, I-1C involved in table, W=R6=R7=R13=R14=R15=R16=R17= H, R9=CH3。
In general formula I-1A,
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-1A, work as R1=Cl, R2=CH3、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- 1-1—9-1-279。
Table 9-2：In general formula I-1A, 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-1A, 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-1A, 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, representation compound number be followed successively by 9-4-1- 9-4-279。
Table 10：In general formula I-1A, work as R1=CH3、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, representation compound number be followed successively by 10-1- 10-279。
Table 10-1：In general formula I-1A, work as R1=CH3、R2=Cl, R3=R4=R5=H, R8=CH3, during 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 10-1-1—10-1-279。
Table 10-2：In general formula I-1A, work as R1=CH3、R2=Cl, R3=R4=R5=H, R8When=H, 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 10-2-1—10-2-279。
Table 10-3：In general formula I-1A, work as R1=CH3、R2=Cl, R3=R4=R5=H, R8=CH3, during 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 10-3-1—10-3-279。
Table 11：In general formula I-1A, work as R1=C2H5、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, representation compound number be followed successively by 11-1- 11-279。
Table 11-1：In general formula I-1A, work as R1=C2H5、R2=Cl, R3=R4=R5=H, R8=CH3, during 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。
Table 11-2：In general formula I-1A, work as R1=C2H5、R2=Cl, R3=R4=R5=H, R8When=H, 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 11-2-1—11-2-279。
Table 11-3：In general formula I-1A, work as R1=C2H5、R2=Cl, R3=R4=R5=H, R8=CH3, during 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。
Table 12：In general formula I-1A, work as R1=CHF2、R2=Cl, 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 12-1—12-279。
Table 12-1：In general formula I-1A, work as R1=CHF2、R2=Cl, R3=R4=R5=H, R8=CH3, during 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。
Table 12-2：In general formula I-1A, work as R1=CHF2、R2=Cl, R3=R4=R5=H, R8When=H, 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 12-2-1—12-2-279。
Table 12-3：In general formula I-1A, work as R1=CHF2、R2=Cl, R3=R4=R5=H, R8=CH3, during 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。
Table 13：In general formula I-1A, work as R1=CF3、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, representation compound number be followed successively by 13-1- 13-279。
Table 14：In general formula I-1A, work as R1=Cl, 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 14-1—14-279。
Table 15：In general formula I-1A, work as R1=CH3、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 15-1—15-279。
Table 16：In general formula I-1A, work 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。
Table 17：In general formula I-1A, work 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。
Table 18：In general formula I-1A, work as R1=CF3、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 18-1—18-279。
In general formula I-1B
Table 19：In general formula I-1B, work as R3=R4=R5=H, R8When=H, m=1, substituent group (R10)nWith substituting table 9 Suo Shi 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 19-1-19-279.
Table 19-1：In general formula I-1B, work as R3=R4=R5=H, R8=CH3, during m=1, substituent group (R10)nWith being taken shown in table 9 Consistent for base, 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.
Table 19-2：In general formula I-1B, work as R3=R4=R5=H, R8When=H, m=2, substituent group (R10)nWith being taken shown in table 9 Consistent for base, 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.
Table 19-3：In general formula I-1B, work as R3=R4=R5=H, R8=CH3, during m=2, substituent group (R10)nWith being taken shown in table 9 Consistent for base, 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.
Table 20：In general formula I-1B, work as R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)nWith being taken shown in table 9 Consistent for base, 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-1C
Table 21：In general formula I-1C, work as R3=R4=R5=H, R18=Cl, R8When=H, m=1, 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 21-1-21-279.
Table 21-1：In general formula I-1C, work as R3=R4=R5=H, R18=Cl, R8=CH3, during 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, representation compound number be followed successively by 21-1-1- 21-1-279。
Table 21-2：In general formula I-1C, work as R3=R4=R5=H, R18=Cl, R8When=H, 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 21-2-1-21- 2-279。
Table 21-3：In general formula I-1C, work as R3=R4=R5=H, R18=Cl, R8=CH3, during m=2, 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, representation compound number be followed successively by 21-3-1- 21-3-279。
Table 22：In general formula I-1C, work as R3=R4=R5=H, 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 22-1-22- 279。
Table 23：In general formula I-1C, work as R3=R4=H, R5=CH3, R18=Cl, 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 23-1-23- 279。
Table 24：In general formula I-1C, work as R3=R4=H, R5=CH3, R18=CH3, 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 24-1-24- 279。
In general formula I-1D
Table 25：In general formula I-1D, work 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。
Table 26：In general formula I-1D, work 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。
Table 27：In general formula I-1D, work as R1=CHF2、R2=Cl, R3=R4=R5=H, X=O, R8When=H, m=1, substitution Base (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。
Table 28：In general formula I-1D, work 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。
Table 29：In general formula I-1D, work 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。
Table 30：In general formula I-1D, work as R1=CHF2、R2=Cl, R3=R4=R5=H, X=S, R8When=H, m=1, substitution Base (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-1A, 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 present 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：
Compound of Formula I is obtained by the reaction in suitable solvent in alkaline conditions in intermediate II and III.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium acid carbonate, triethylamine, pyridine, Sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
Reaction 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 usually 20-100 DEG C in room temperature between solvent boiling point temperature.
Reaction time for 30 minutes to 20 it is small when, when usual 1-10 is small.
Intermediate II part is commercially available, can also be prepared 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 It is prepared by Society (1955), the method 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, reacted in suitable solvent 30 minutes to 20 it is small when, When usually 1-10 is small, intermediate M2 is made, this step operation method is with reference to 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 reacts again with X1 is made M4, this step operation method is with reference to Pest Management science, and 66 (1),2010,107-112；Last M4 is reacted with corresponding halide is made III, this step operation method reference US20100158860, WO2011133444 and Bioorganic＆Medicinal Chemistry, 20 (20), 6109-6122, 2012。
Further, the preparation of general formula compound I-1 is with the following method：Specific each step reaction conditioned reference prepares logical The corresponding steps and relevant references of compound of formula I.
General formula I-1 compounds are obtained by the reaction in intermediate II and III in suitable solvent in alkaline conditions.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium acid carbonate, triethylamine, pyridine, Sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
Reaction 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 usually 20-100 DEG C in room temperature between solvent boiling point temperature.
Reaction time for 30 minutes to 20 it is small when, when usual 1-10 is small.
Intermediate II part is commercially available, can also be prepared 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 It is prepared by Society (1955), the method p.3478-3481 described.
Intermediate III is the key intermediate for preparing general formula I-1 compounds of the present invention, is prepared as follows：
Intermediate M1 and dimethyl carbonate at a suitable temperature, reacted in suitable solvent 30 minutes to 20 it is small when, When usually 1-10 is small, intermediate M2 is made, this step operation method is with reference to 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 reacts again with X1 is made M4, this step operation method is with reference to Pest Management science, and 66 (1),2010,107-112；Last M4 is reacted with corresponding halide is made III, this step operation method reference US20100158860, WO2011133444 and Bioorganic＆Medicinal Chemistry, 20 (20), 6109-6122, 2012。
Although the compound of Formula I of the present invention falls within the substitution containing pyrimidine with disclosed some compounds in the prior art Pyrazole compound, but there are still dramatically different for structure feature.And cause the present invention's due to the difference in these structures Compound has preferably sterilization and pesticide and miticide actility.
Compound of Formula I shows excellent activity to a variety of germs in agricultural or other field, to pest evil mite Show preferable activity.Therefore, technical scheme further includes compound of Formula I and is used as in agricultural or other field Prepare the purposes of fungicide, insecticidal/acaricidal agent.
The example of disease referenced below is only used for illustrating the present invention, but never limits the present invention.
Compound of Formula I can be used for preventing following disease：Oomycetes diseases, such as downy mildew (cucumber downy mildew, rape downy mildew Disease, downy mildew, beet downy mildew, downy mildew of sugarcane, tobacco downy mildew, pea downy mildew, sponge gourd downy mildew, wax gourd downy mildew Disease, muskmelon downy mildew, cabbage downy mildew, downy mildew of spinach, radish downy mildew, downy mildew of garpe, onion mildew), white rust (white rust of colza, cabbage white blister), samping off (rape samping off, Tobacco seedling diseases, tomato samping off, capsicum samping off, Eggplant samping off, cucumber samping off, cotton seedling samping off), pythium rot (capsicum pythium rot, sponge gourd pythium rot, wax gourd pythium rot), epidemic disease Disease is (broad bean epidemic disease, Cucumber Blight, pumpkin epidemic disease, wax gourd epidemic disease, watermelon epidemic disease, muskmelon blight, capsicum epidemic disease, leek epidemic disease, big Garlic epidemic disease, Cotton blight), late blight (late blight of potato, tomato late blight) etc.；Fungi Imperfecti disease, such as droop, (sweet potato is withered Wither disease, cotton wilt, sesame droop, castor-oil plant droop, tomato wilt, Kidney bean droop, cucumber fusarium axysporum, sponge gourd is withered Wither disease, pumpkin droop, wax gourd droop, watermelon blight, Muskmelon Fusarium wilt, capsicum wilt, faba bean Fusarium wilt, rape is withered Wither disease, soybean Fusariuming disease), root rot (Fusarium solani, eggplant root rot, Kidney bean root rot, cucumber root rot, balsam pear root-rot Disease, cotton black root rot, root rot of Vicia faba), damping-off (cotton seedling blight, sesame damping-off, capsicum damping-off, cucumber rhizoctonia rot, Chinese cabbage damping-off), anthracnose (anthracnose of sorghum, cotton anthracnose, bluish dogbane anthracnose, jute anthracnose, anthracnose of flax, cigarette Careless anthracnose, mulberry anthracnose, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, balsam pear anthracnose, western calabash Reed anthracnose, wax gourd anthracnose, watermelon anthrax, muskmelon anthracnose, lichee anthracnose), verticillium wilt (cotton verticillium wilt, Xiang Certain herbaceous plants with big flowers verticillium wilt, tomato verticillium wilt, capsicum verticillium wilt, eggplant verticillium wilt), scab (cucurbita pepo scab, wax gourd scab, sweet tea Melon scab), gray mold (cotton boll gray mold, bluish dogbane gray mold, graw mold of tomato, Botrytis cinerea, Kidney bean gray mold, celery Gray mold, spinach gray mold, Kiwi berry gray mold), brown spot (cotton brown spot, jute brown spot, beet cercospora leaf spot, peanut Brown spot, capsicum brown spot, wax gourd brown spot, soybean brown spot, septorial brown spot of sunflower, pea brown spot, broad bean brown spot), Black spot (flax vacation black spot, alternaria stem rot of colza, sesame black spot, sunflower black spot, castor-oil plant black spot, tomato black spot, Capsicum black spot, eggplant black spot, Kidney bean black spot, cucumber black spot, celery black spot, carrot black rot, carrot blackspot Disease, melanose or canker of apple, the cercospora black spot of peanut), spot blight (spotted wilt of tomato, capsicum spot blight, celery septoria disease), early blight (kind Eggplant early blight, capsicum early blight, eggplant early blight, target, early blight of celery), ring spot (soybean ring spot, sesame Numb ring spot, Kidney bean ring spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon leaf blight, muskmelon leaf blight), stem Basal stem rot (tomato base rot disease, Kidney bean base rot disease) and other (Helminthosporium carbonum, bluish dogbane waist folding disease, rice blast, the black sheaths of chestnut Disease, sugarcane eye spot, cotton boll aspergillosis, peanut crown rot, soybean stem wilt, soybean diplostomiasis, muskmelon leaf blight, peanut filigree Disease, the red leaf spot of tea, pepper white star disease, wax gourd leaf spot, celery black rot, spinach heartrot, bluish dogbane leaf mold, bluish dogbane spot Disease, jute stem blight, purple spot of soybean, Alternaria sesami, castor-oil plant graywall, dark brown leaf spot, cercospora leaf spot of egg plant, dish Bean red pinta, balsam pear Leucoplakia, watermelon spot disease, jute withered rotten disease, sunflower root stem rot, Kidney bean charcoal rot, soybean target spot Disease, eggplant stick spore leaf spot, Leaf Spot Caused by Corynespora cassiicola on Cucumber, leaf muld of tomato, eggplant leaf mold, broad bean red spot etc.) etc.；Basidiomycetes disease Evil, such as rust (stripe rust of wheat, the stem rust of wheat, wheat leaf rust, Peanut Rust, rust of sunflower, sugarcane rust, leek Rust, rust of onion, chestnut rust, soybean rust), smut (maize head smut, corn smut, head smut of sorghum, sorghum Smut, covered kernel smut of kaoliang, high beam column smut, chestnut kernel smut, smut of sugarcane, Bean rust disease) and other are (such as small Wheat banded sclerotial blight, rice sheath blight disease etc.) etc.；Sac fungus disease, such as powdery mildew (wheat powdery mildew, rape powdery mildew, sesame white powder Disease, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, powdery mildew of pea, sponge gourd powdery mildew, squash marble dust, cucurbita pepo Powdery mildew, wax gourd powdery mildew, melon powdery mildew, uncinula necator, broad bean powdery mildew), sclerotiniose (flax sclerotiniose, Sclerotina Sclerotiorum in Winter Rape Core disease, soybean sclerotinia crown rot, peanut sclerotiniose, tobacco sclerotiniose, capsicum sclerotiniose, eggplant sclerotiniose, bean sclerotinia rot, asparagus pea Core disease, cucumber timberrot, balsam pear sclerotiniose, wax gourd sclerotinia, watermelon sclerotiniose, celery sclerotiniose), scab (the black star of apple Disease, pear scab) etc..
Due to its positive characteristic, above-claimed cpd is advantageously used for protection agricultural and the important crop of horticulture, family The environment that poultry and breeding stock and the mankind often go is from germ, the injury of pest evil mite.
To obtain ideal effect, the dosage of compound changes due to 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 used.
The compound dosage of 10 grams -5 kilograms of per hectare can provide sufficient prevention.
Present invention additionally comprises using compound shown in general formula I as active component sterilization, insecticide acaricide composition.This is killed The weight percentage of active component is between 0.5-99% in bacterium, insecticide acaricide composition.The sterilization, insecticide acaricide composition In further include agricultural, forestry, acceptable carrier in health.
The composition of the present invention can be applied in the form of preparation.Compound shown in general formula I is dissolved or divided as active component It is more readily dispersible when dissipating in carrier or being configured to preparation to be used 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, at least add in a kind of Liquid or solid carrier, and appropriate surfactant can be added in when needed.
Technical scheme further includes anti-pathogen, the method for pest evil mite：By the sterilization of the present invention, Insecticiding-miticiding Composition is imposed on the germ or its growth medium.The more suitable effective amount generally selected is per hectare 10 grams to 1000 Gram, preferably effective quantity is 20 grams to 500 grams of per hectare.
For some applications, for example, agriculturally can the sterilization of the present invention, add in insecticide acaricide composition it is a kind of or A variety of others fungicide, insecticidal/acaricidal agent, herbicide, plant growth regulator or fertilizer etc., thus can generate additional excellent Point and effect.
It should be appreciated that in scope defined by the claims of the present invention, various conversion and change can be carried out.
Specific embodiment
Specific examples below is used for further illustrating the present invention, but the present invention be only limitted to absolutely not these examples (except as otherwise It is raw materials used to be commercially available outside indicating).
Synthetic example
Embodiment 1：The preparation of bis- chloro- 6- methylpyrimidines of intermediate 4,5-
1) preparation of the chloro- 6- methylpyrimidines of 4- hydroxyls -5-
It is stirred at room temperature and lower 8.80g is slowly added dropwise into the 50ml methanol solutions 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 esters, continue to be stirred at room temperature reaction 5-7 it is small when.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 is mutually extracted with (3 × 50ml) ethyl acetate, anhydrous Magnesium sulfate is dry, filters, precipitation.Residue is dissolved in 50ml ethyl acetate, is stood overnight, and filters to obtain orange/yellow solid 6.48g. Yield 66%, 181~184 DEG C of fusing point.
2) preparation of bis- chloro- 6- methylpyrimidines of 4,5-
The chloro- 6- methylpyrimidines of 14.5g (0.1mol) 4- hydroxyls -5- are dissolved in 50ml toluene solutions, to reaction under stirring 50ml phosphorus oxychloride is instilled in bottle, when the complete temperature rising reflux reaction 5-7 of drop is small.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 is mutually 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.
Embodiment 2：The preparation of 4,5- dichloro-thiophenes simultaneously [2,3-d] pyrimidine
Take 2- Amino 3 cyano -4- oxo -5,5- dihydro-thiophenes and 250ml phosphorus oxychloride (POCl3) in reaction bulb, 38ml n,N-Dimethylformamide is slowly added dropwise at room temperature, is added dropwise within about 30 minutes.React at room temperature 1 it is small when, then be warming up to 75 DEG C reaction 3 it is small when.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-quinazolines
1) preparation of quinazoline -4 (3H) -one
It takes 13.7g (0.1mol) ortho-aminobenzoic acids with 20ml formamides in 250ml there-necked flasks, is warming up to 140 DEG C instead When answering 5-8 small.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 afterwards Temperature filters and obtains rufous 10.96g, yield 75.1% with filter cake is washed with anhydrous ether.
2) preparation of 4- chloro-quinazolines
Taking 14.6g (0.1mol) (3H) -one of quinazoline -4,50ml thionyl chlorides make solvent in 250ml single port bottles, heating To back flow reaction 4-6 it is small when.TLC is monitored after completion of the reaction, and reaction solution is poured into water stirring 30min after cooling, and filtering is used in combination Anhydrous ether washs to obtain red brown solid 10.96g, yield 92.7%.
Embodiment 4：The synthesis of intermediate 2- (1- (4- chlorphenyls) -1H- pyrazoles -3- oxygroups) ethylamine hydrochloride
1) preparation of N-Boc-2- bromines ethamine
20.5g (0.1mol) bromine ethamine bromate is placed in 80ml tetrahydrofurans, sequentially adds 10.08g (0.12mol) Lower dropwise addition 21.80g (0.1mol) di-tert-butyl dicarbonate is stirred at room temperature in sodium acid carbonate, 50ml water, and drop finishes, the reaction was continued 4-10 Hour.After completion of the reaction, remove solvent under reduced pressure, add in the extraction of (3 × 50ml) ethyl acetate, organic phase saturated salt solution 50ml It washs, colourless oil liquid 21.68g, yield 96.8% is obtained after precipitation.
2) preparation of N-Boc-2- (3- (4- chlorphenyls) -1- methyl pyrazole -5- oxygroups) ethamine
By 2.24g (0.01mol) N-Boc-2- bromines ethamine and 2.09g (0.01mol) 2- (3- (4- chlorphenyls) -1- methyl - 5- hydroxypyrazoles (preparation method refers to Pest Manag Sci (2010), 66 (1), p.107-112) are added in 50ml butanone, are added Enter 2.76g (0.02mol) potassium carbonate, be heated to flowing back under stirring, when reaction 4-10 is small, TLC is monitored after completion of the reaction, and decompression is steamed Except solvent, the extraction of (3 × 50ml) ethyl acetate is added in, organic phase is washed with saturated salt solution 50ml, residue column layer after precipitation Analysis (eluant, eluent be ethyl acetate and petroleum ether, volume ratio 1:6) yellow solid 2.96g, yield 83.8% are obtained.
3) preparation of 2- (1- (4- chlorphenyls) -1H- pyrazoles -3- oxygroups) ethylamine hydrochloride
3.51g (0.01mol) N-Boc-2- (3- (4- chlorphenyls) -1- methyl pyrazole -5- oxygroups) ethamine is added in into 50ml In ethyl acetate, be stirred at room temperature it is lower dropwise addition 6ml concentrated hydrochloric acids, solid dissolving, continue stir 4-5 it is small when, TLC monitoring reaction finishes Afterwards, remove solvent under reduced pressure, add in 10ml dichloromethane stirring half an hour, filtering, and with dichloromethane wash filter cake to obtain 2.33g white Color solid.
Embodiment 5：The preparation of compound 11-19
By bis- chloro- 6- ethyl-pyrimidines of 1.77g (0.01mol) 4,5- and 2.88g (0.01mol) 2- (3- (4- chlorphenyls) -1- Methyl pyrazole -5- oxygroups) ethylamine hydrochloride add in 50ml toluene in.4.45g (0.022mol) triethylamine is added in, is heated to back Stream, when reaction 4-10 is small, TLC is monitored after completion of the reaction, removes solvent under reduced pressure, adds in the extraction of (3 × 50ml) ethyl acetate, organic It is mutually washed with saturated salt solution 50ml, (eluant, eluent is ethyl acetate and petroleum ether (boiling range 60-90 to residue column chromatography after precipitation DEG C), volume ratio 1:4) white solid 3.12g, yield 79.6% are obtained.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.46(s,1H,Pyrimidine-H),7.64- 7.65(d,2H,Ph-2,6-2H),7.32-7.34(d,2H,Ph-3,5-2H),5.82(s,1H,Pyrazole-4-H),5.77 (s,1H,NH),4.30((t,2H,O-CH2),3.97-4.00(m,2H,N-CH2),3.70(s,3H,N-CH3),2.80-2.84 (m,2H,CH2),1.27(t,3H,CH3).
Embodiment 6：The preparation of compound 19-19
By 1.64g (0.01mol) 4- chloro-quinazolines and 2.88g (0.01mol) 2- (3- (4- chlorphenyls) -1- methyl-pyrrole Azoles -5- oxygroups) ethylamine hydrochloride add in 50ml toluene in.4.45g (0.022mol) triethylamine is added in, is heated to flowing back, is reacted When 4-10 is small, TLC is monitored after completion of the reaction, removes solvent under reduced pressure, adds in the extraction of (3 × 50ml) ethyl acetate, 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 for residue column chromatography after precipitation Product is than being 1:4) 2.98g white solids, yield 78.6%, 197.2 DEG C of fusing point are obtained.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.65(s,1H,Quinazoline-3-H),7.73 (d, J=2.4Hz, 1H, Pyrazole-5-H), 7.40-7.72 (m, 5H, Ph-3,4,5,6-5H), 7.40-7.72 (m, 4H, ), Quinazoline-5,6,7,8-4H 5.97 (d, J=2.4Hz, 1H, Pyrazole-4-H), 5.90 (s, 1H, NH), 4.63 (t,2H,O-CH2),4.06(m,2H,N-CH2)。
Embodiment 7：The preparation of compound 21-19
By 0.41g (0.002mol) 4,5- dichloro-thiophenes simultaneously [2,3-d] pyrimidine and 0.58g (0.002mol) 2- (3- (4- chlorine Phenyl) -1- methyl pyrazole -5- oxygroups) ethylamine hydrochloride add in 50ml toluene in.0.45g (0.0022mol) triethylamine is added in, It is heated to flowing back, when reaction 4-10 is small, TLC is monitored after completion of the reaction, removes solvent under reduced pressure, adds in (3 × 50ml) ethyl acetate Extraction, organic phase are washed with saturated salt solution 50ml, and (eluant, eluent is ethyl acetate and petroleum ether to residue column chromatography after precipitation (60-90 DEG C), volume ratio 1:4) white solid 0.64g, yield 75.8%, 167.9 DEG C of fusing point are obtained.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.46(s,1H,Pyrimidine-H),8.22- 8.24(d,2H,Ph-2,6-2H),7.85-7.88(d,2H,Ph-3,5-2H),5.94(s,1H,Pyrazole-4-H),5.71 (s,1H,NH),4.33(t,2H,O-CH2),3.97-4.02(m,2H,N-CH2),3.74(s,3H,N-CH3),2.79-2.82(m, 2H,CH2),1.27(t,3H,CH3).
Other compounds of the present invention are referred to above example preparation.
Part of compounds physical data and nuclear magnetic data (1HNMR, 600MHz, internal standard TMS, ppm) it is as follows：
Compound 10-1:117.8 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.70-7.73(d, 2H,Ph-2,6-2H),7.37(t,2H,Ph-3,5-2H),7.28(t,1H,Ph-4-H),5.85(s,1H,Pyrazole-4-H), 5.75(s,1H,NH),4.30(t,2H,O-CH2),3.95-4.00(m,2H,N-CH2),3.71(s,3H,N-CH3),2.48(s, 3H,CH3)。
Compound 10-4:δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.67(t,2H,Ph-2,6-2H),7.06 (t,2H,Ph-3,5-2H),5.80(s,1H,Pyrazole-4-H),5.79(s,1H,NH),4.30((t,2H,O-CH2), 3.95-4.00(m,2H,N-CH2),3.70(s,3H,N-CH3),2.48(s,3H,CH3)。
Compound 10-17:Grease δ (CDCl3):8.40(s,1H,Pyrimidine-H),7.74(dd,1H,Ph-6- 1H),7.40(dd,1H,Ph-3-1H),7.28(td,1H,Ph-5-1H),7.23(td,1H,Ph-4-1H),6.09(s,1H, Pyrazole-4-H),5.74(s,1H,NH),4.31(t,2H,O-CH2),3.96-3.99(m,2H,N-CH2),3.72(s,3H, N-CH3),2.48(s,3H,CH3).
Compound 10-19:Grease δ (CDCl3):8.41(s,1H,Pyrimidine-H),7.64-7.66(d,2H, Ph-2,6-2H),7.32-7.35(d,2H,Ph-3,5-2H),5.82(s,1H,Pyrazole-4-H),5.77(s,1H,NH), 4.30(t,2H,O-CH2),3.95-4.00(m,2H,N-CH2),3.68(s,3H,N-CH3),2.48(s,3H,CH3)。
Compound 10-21:87.8 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.72(d,1H,Ph- 6-1H),7.43(s,1H,Ph-3-1H),7.26(dd,1H,Ph-5-1H),6.09(s,1H,Pyrazole-4-H),5.73(s, 1H,NH),4.31(t,2H,O-CH2),3.96-3.99(m,2H,N-CH2),3.72(s,3H,N-CH3),2.49(s,3H,CH3).
Compound 10-34:155.0 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.58-7.60(d, 2H,Ph-2,6-2H),7.48-7.50(d,2H,Ph-3,5-2H),5.82(s,1H,Pyrazole-4-H),5.77(s,1H, NH),4.29(t,2H,O-CH2),3.95-4.00(m,2H,N-CH2),3.70(s,3H,N-CH3),2.48(s,3H,CH3).
Compound 10-52:192.0 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),8.22-8.24(d, 2H,Ph-2,6-2H),7.85-7.88(d,2H,Ph-3,5-2H),5.94(s,1H,Pyrazole-4-H),5.71(s,1H, NH),4.32(t,2H,O-CH2),3.97-4.02(m,2H,N-CH2),3.74(s,3H,N-CH3),2.48(s,3H,CH3).
Compound 10-57:δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.59-7.62(d,2H,Ph-2,6- 2H),7.16-7.19(d,2H,Ph-3,5-2H),5.82(s,1H,Pyrazole-4-H),5.78(s,1H,NH),4.30(t, 2H,O-CH2),3.95-4.00(m,2H,N-CH2),3.70(s,3H,N-CH3),2.48(s,3H,Pyrimidine-CH3), 2.88(s,3H,Ph-CH3).
Compound 10-68:120.6 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.97(s,1H, Ph-2-1H),7.89(d,1H,Ph-6-1H),7.53(d,1H,Ph-4-1H),7.48(t,1H,Ph-5-1H),5.90(s,1H, Pyrazole-4-H),5.73(s,1H,NH),4.31(t,2H,O-CH2),3.97-4.00(m,2H,N-CH2),3.72(s,3H, N-CH3),2.48(s,3H,CH3).
Compound 11-1:Grease δ (CDCl3):8.46(s,1H,Pyrimidine-H),7.70-7.73(d,2H,Ph- 2,6-2H),7.37(t,2H,Ph-3,5-2H),7.28(t,1H,Ph-4-H),5.85(s,1H,Pyrazole-4-H),5.75 (s,1H,NH),4.30(t,2H,O-CH2),3.96-4.00(m,2H,N-CH2),3.65(s,3H,N-CH3),2.79-2.82(m, 2H,CH2),1.27(t,3H,CH3)。
Compound 11-1-1: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 11-4:δ(CDCl3):8.46(s,1H,Pyrimidine-H),7.67(d,2H,Ph-2,6-2H),7.05 (d,2H,Ph-3,5-2H),5.80(s,1H,Pyrazole-4-H),5.79(s,1H,NH),4.30((t,2H,O-CH2), 3.95-4.00(m,2H,N-CH2),3.70(s,3H,N-CH3),2.79-2.82(m,2H,CH2),1.27(t,3H,CH3).
Compound 11-17:Grease δ (CDCl3):8.44(s,1H,Pyrimidine-H),7.74(dd,1H,Ph-6- 1H),7.40(dd,1H,Ph-3-1H),7.28(td,1H,Ph-5-1H),7.23(td,1H,Ph-4-1H),6.09(s,1H, Pyrazole-4-H),5.75(s,1H,NH),4.30(t,2H,O-CH2),3.96-3.99(m,2H,N-CH2),3.72(s,3H, N-CH3),2.78-2.82(m,2H,CH2),1.26(t,3H,CH3).
Compound 11-21:138.9 DEG C of fusing point.δ(CDCl3):8.45(s,1H,Pyrimidine-H),7.72(d,1H, Ph-6-1H),7.43(s,1H,Ph-3-1H),7.27(dd,1H,Ph-5-1H),7.73(t,1H,CH),6.09(s,1H, Pyrazole-4-H),5.73(s,1H,NH),4.31(t,2H,O-CH2),4.02-4.05(m,2H,N-CH2),3.72(s,3H, N-CH3),2.79-2.83(m,2H,CH2),1.27(t,3H,CH3).
Compound 11-34:133.3 DEG C of fusing point.δ(CDCl3):8.45(s,1H,Pyrimidine-H),7.58-7.60(d, 2H,Ph-2,6-2H),7.47-7.49(d,2H,Ph-3,5-2H),5.82(s,1H,Pyrazole-4-H),5.77(s,1H, NH),4.30(t,2H,O-CH2),3.95-4.00(m,2H,N-CH2),3.70(s,3H,N-CH3),2.79-2.82(m,2H, CH2),1.27(t,3H,CH3)。
Compound 11-52:166.8 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),8.22-8.24(d, 2H,Ph-2,6-2H),7.85-7.88(d,2H,Ph-3,5-2H),5.94(s,1H,Pyrazole-4-H),5.71(s,1H, NH),4.32(t,2H,O-CH2),3.97-4.02(m,2H,N-CH2),3.74(s,3H,N-CH3),2.79-2.83(m,2H, CH2),1.27(t,3H,CH3).
Compound 11-57:δ(CDCl3):8.45(s,1H,Pyrimidine-H),7.59-7.62(d,2H,Ph-2,6- 2H),7.16-7.19(d,2H,Ph-3,5-2H),5.82(s,1H,Pyrazole-4-H),5.74(s,1H,NH),4.30(t, 2H,O-CH2),3.95-4.00(m,2H,N-CH2),3.70(s,3H,N-CH3),2.77-2.84(m,2H,Pyrimidine- CH2),2.31(s,3H,Ph-CH3),1.24(t,3H,-CH2CH3)。
Compound 11-68:99.8 DEG C of fusing point.δ(CDCl3):8.46(s,1H,Pyrimidine-H),7.97(s,1H,Ph- 2-1H),7.89(d,1H,Ph-6-1H),7.53(d,1H,Ph-4-1H),7.48(t,1H,Ph-5-1H),5.90(s,1H, Pyrazole-4-H),5.73(s,1H,NH),4.32(t,2H,O-CH2),3.97-4.00(m,2H,N-CH2),3.73(s,3H, N-CH3),2.79-2.83(m,2H,CH2),1.27(t,3H,CH3).
Compound 11-75:127.8 DEG C of fusing point.δ(CDCl3):8.45(s,1H,Pyrimidine-H),7.63-7.64(d, 2H,Ph-2,6-2H),7.25-7.26(d,2H,Ph-3,5-2H),5.82(s,1H,Pyrazole-4-H),5.73(s,1H, NH),4.30(t,2H,O-CH2),3.97-3.99(m,2H,N-CH2),3.70(s,3H,N-CH3),2.79-2.83(m,2H, CH2),2.50(s,3H,S-CH3),1.27(t,3H,CH3).
Compound 11-78:δ(CDCl3):8.50(s,1H,Pyrimidine-H),7.71-7.74(d,2H,Ph-2,6- 2H),7.20-7.23(d,2H,Ph-3,5-2H),5.83(s,1H,Pyrazole-4-H),5.74(s,1H,NH),4.31(t, 2H,O-CH2),3.95-4.01(m,2H,N-CH2),3.71(s,3H,N-CH3),2.77-2.84(m,2H,CH2),1.26(t, 3H,CH3)。
Compound 12-1:115.4 DEG C of fusing point.δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.70-7.73(d, 2H,Ph-2,6-2H),7.37(t,2H,Ph-3,5-2H),7.28(t,1H,Ph-4-H),6.73(t,1H,CH),6.00(s,1H, NH),5.85(s,1H,Pyrazole-4-H),4.32(t,2H,O-CH2),4.01-4.06(m,2H,N-CH2),3.71(s,3H, N-CH3).
Compound 12-1-1:δ(CDCl3):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 12-4:δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.67(t,2H,Ph-2,6-2H),7.06 (t,2H,Ph-3,5-2H),6.73(t,1H,CH),6.00(s,1H,NH),5.80(s,1H,Pyrazole-4-H),4.32(t, 2H,O-CH2),4.02-4.05(m,2H,N-CH2),3.70(s,3H,N-CH3).
Compound 12-17:Grease δ (CDCl3):8.59(s,1H,Pyrimidine-H),7.75(dd,1H,Ph-6- 1H),7.41(dd,1H,Ph-3-1H),7.28(td,1H,Ph-5-1H),7.24(td,1H,Ph-4-1H),6.73(t,1H, CH),6.10(s,1H,Pyrazole-4-H),6.01(s,1H,NH),4.33(t,2H,O-CH2),4.02-4.05(m,2H,N- CH2),3.73(s,3H,N-CH3).
Compound 12-19:143.2 DEG C of fusing point.δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.63-7.66(d, 2H,Ph-2,6-2H),7.32-7.35(d,2H,Ph-3,5-2H),6.73(t,1H,CH),6.00(s,1H,NH),5.82(s, 1H,Pyrazole-4-H),4.32(t,2H,O-CH2),4.01-4.06(m,2H,N-CH2),3.70(s,3H,N-CH3).
Compound 12-21:116.3 DEG C of fusing point.δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.72(d,1H, Ph-6-1H),7.43(s,1H,Ph-3-1H),7.26(dd,1H,Ph-5-1H),7.73(t,1H,CH),6.10(s,1H, Pyrazole-4-H),6.00(s,1H,NH),4.33(t,2H,O-CH2),4.02-4.05(m,2H,N-CH2),3.72(s,3H, N-CH3).
Compound 12-34:149.5 DEG C of fusing point.δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.57-7.60(d, 2H,Ph-2,6-2H),7.47-7.50(d,2H,Ph-3,5-2H),6.73(t,1H,CH),6.00(s,1H,NH),5.82(s, 1H,Pyrazole-4-H),4.32(t,2H,O-CH2),4.01-4.06(m,2H,N-CH2),3.70(s,3H,N-CH3)。
Compound 12-52:215.1 DEG C of fusing point.δ(CDCl3):8.60(s,1H,Pyrimidine-H),8.22-8.24(d, 2H,Ph-2,6-2H),7.85-7.88(d,2H,Ph-3,5-2H),6.72(t,1H,CH),6.00(s,1H,NH),5.94(s, 1H,Pyrazole-4-H),4.33(t,2H,O-CH2),4.04-4.07(m,2H,N-CH2),3.74(s,3H,N-CH3).
Compound 12-57:δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.59-7.62(d,2H,Ph-2,6- 2H),7.16-7.19(d,2H,Ph-3,5-2H),6.73(t,1H,CH),6.02(s,1H,NH),5.82(s,1H,Pyrazole- 4-H),4.32(t,2H,O-CH2),4.00-4.06(m,2H,N-CH2),3.70(s,3H,N-CH3),2.88(s,3H,Ph- CH3)。
Compound 12-66:Grease δ (CDCl3):8.59(s,1H,Pyrimidine-H),7.63-7.64(d,2H, Ph-2,6-2H),7.20-7.22(d,2H,Ph-3,5-2H),6.73(t,1H,CH),6.03(s,1H,NH),5.82(s,1H, Pyrazole-4-H),4.31(t,2H,O-CH2),4.02-4.04(m,2H,N-CH2),3.70(s,3H,N-CH3),2.64- 2.68(m,2H,CH2),1.25(t,3H,CH3).
Compound 12-68:118.3 DEG C of fusing point.δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.97(s,1H, Ph-2-1H),7.89(d,1H,Ph-6-1H),7.53(d,1H,Ph-4-1H),7.48(t,1H,Ph-5-1H),6.73(t,1H, CH),6.02(s,1H,NH),5.90(s,1H,Pyrazole-4-H),4.33(t,2H,O-CH2),4.03-4.06(m,2H,N- CH2),3.72(s,3H,N-CH3).
Compound 12-75:130.4 DEG C of fusing point.δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.63-7.64(d, 2H,Ph-2,6-2H),7.25-7.26(d,2H,Ph-3,5-2H),6.75(t,1H,CH),6.00(s,1H,NH),5.82(s, 1H,Pyrazole-4-H),4.30(t,2H,O-CH2),3.97-4.00(m,2H,N-CH2),3.70(s,3H,N-CH3),2.50 (s,3H,S-CH3).
Compound 12-78:δ(CDCl3):8.60(s,1H,Pyrimidine-H),7.72-7.74(d,2H,Ph-2,6- 2H),7.20-7.23(d,2H,Ph-3,5-2H),6.73(t,1H,CH),6.00(s,1H,NH),5.83(s,1H,Pyrazole- 4-H),4.32(t,2H,O-CH2),4.01-4.06(m,2H,N-CH2),3.71(s,3H,N-CH3)。
Compound 19-1:δ(CDCl3):8.71(s,1H,Quinazoline-3-H),7.88-7.91(d,1H, Quinazoline-5-H),7.77-7.80(d,2H,Ph-2,6-2H),7.71(t,2H,Quinazoline-6,7-2H),7.49 (t,1H,Ph-4-H),7.36(d,2H,Ph-3,5-2H),7.28-7.30(d,1H,Quinazoline-7-H),6.38(s,1H, NH),5.85(s,1H,Pyrazole-4-H),4.40(t,2H,O-CH2),4.12-4.16(m,2H,N-CH2),3.70(s,3H, N-CH3)。
Compound 19-17:δ(CDCl3):8.71(s,1H,Quinazoline-3-H),8.31-8.32(d,1H, Quinazoline-5-H),7.88-7.90(d,1H,Ph-6-H),7.55(t,2H,Quinazoline-6,7-2H),7.50(t, 1H,Ph-3-H),7.40-7.41(d,1H,Ph-5-H),7.28-7.29(d,1H,Quinazoline-8-H),7.23(t,1H, Ph-4-H),6.12(s,1H,Pyrazole-4-H),6.09(s,1H,NH),4.43(t,2H,O-CH2),4.15-4.17(m, 2H,N-CH2),3.74(s,3H,N-CH3)。
Compound 19-21:160.8 DEG C of fusing point.δ(CDCl3):8.68(s,1H,Quinazoline-2-H),7.77(d, 1H,Quinazoline-5-H),7.74(d,1H,Ph-6-H),7.86(d,1H,Quinazoline-8-H),7.77(t,1H, Ph-5-H),7.72(d,1H,Ph-6-H),7.52(t,1H,Quinazoline-6-H),7.51(d,1H,Ph-4-H),7.47 (t,1H,Quinazoline-7-H),6.07(s,1H,NH),5.91(s,1H,Pyrazole-4-H),4.43(t,2H,O- CH2),4.15-4.18(m,2H,N-CH2),3.73(s,3H,N-CH3).
Compound 19-68:154.9 DEG C of fusing point.δ(CDCl3):8.71(s,1H,Quinazoline-2-H),7.96(s, 1H,Ph-6-H),7.89(d,1H,Quinazoline-5-H),7.86(d,1H,Quinazoline-8-H),7.77(t,1H, Ph-5-H),7.72(d,1H,Ph-6-H),7.52(t,1H,Quinazoline-6-H),7.51(d,1H,Ph-4-H),7.47 (t,1H,Quinazoline-7-H),6.07(s,1H,NH),5.91(s,1H,Pyrazole-4-H),4.43(t,2H,O- CH2),4.15-4.18(m,2H,N-CH2),3.73(s,3H,N-CH3).
Compound 21-1:146.4 DEG C of fusing point.δ(CDCl3):8.50(s,1H,Pyrimidine-H),7.70-7.73(d, 2H,Ph-2,6-2H),7.37(t,2H,Ph-3,5-2H),7.28(t,1H,Ph-4-H),7.11(s,1H,Pyrazole-4-H), 6.90(s,1H,NH),5.87(s,1H,Thiophene-H),4.37(t,2H,O-CH2),3.09-4.12(m,2H,N-CH2), 3.72(s,3H,N-CH3).
Compound 21-4:δ(CDCl3):8.49(s,1H,Pyrimidine-H),7.67(d,2H,Ph-2,6-2H),7.11 (s,1H,Pyrazole-4-H),7.05(d,2H,Ph-3,5-2H),6.89(s,1H,NH),5.82(s,1H,Thiophene- H),4.37(t,2H,O-CH2),4.08-4.13(m,2H,N-CH2),3.71(s,3H,N-CH3).
Compound 21-17:114.7 DEG C of fusing point.δ(CDCl3):8.50(s,1H,Pyrimidine-H),7.75(dd,1H, Ph-6-1H),7.41(dd,1H,Ph-3-1H),7.28(td,1H,Ph-5-1H),7.24(td,1H,Ph-4-1H),7.12(s, 1H,Pyrazole-4-H),6.91(s,1H,NH),6.12(s,1H,Thionphene-H),4.38(t,2H,O-CH2),4.10- 4.12(m,2H,N-CH2),3.74(s,3H,N-CH3).
Compound 21-21:127.3 DEG C of fusing point.δ(CDCl3):8.49(s,1H,Pyrimidine-H),7.72(d,1H, Ph-6-1H),7.43(s,1H,Ph-3-1H),7.26(dd,1H,Ph-5-1H),7.12(s,1H,Pyrazole-4-H),6.90 (s,1H,NH),6.11(s,1H,Thiophene-H),4.38(t,2H,O-CH2),4.09-4.12(m,2H,N-CH2),3.73 (s,3H,N-CH3).
Compound 21-34:168.0 DEG C of fusing point.δ(CDCl3):8.49(s,1H,Pyrimidine-H),7.57-7.59(d, 2H,Ph-2,6-2H),7.47-7.50(d,2H,Ph-3,5-2H),7.11(s,1H,Pyrazole-4-H),6.89(s,1H, NH),5.84(s,1H,Thiophene-H),4.36(t,2H,O-CH2),4.08-4.13(m,2H,N-CH2),3.68(s,3H,N- CH3)。
Compound 21-52:214.3 DEG C of fusing point.δ(CDCl3):8.38(s,1H,Pyrimidine-H),8.20-8.23(d, 2H,Ph-2,6-2H),7.92-7.95(d,2H,Ph-3,5-2H),7.56(s,1H,Pyrazole-4-H),7.40(s,1H, NH),6.36(s,1H,Thiophene-H),4.38((t,2H,O-CH2),4.00-4.03(m,2H,N-CH2),3.64(s,3H, N-CH3).
Compound 21-68:160.0 DEG C of fusing point.δ(CDCl3):8.50(s,1H,Pyrimidine-H),7.97(s,1H, Ph-2-1H),7.89(d,1H,Ph-6-1H),7.53(d,1H,Ph-4-1H),7.48(t,1H,Ph-5-1H),7.11(s,1H, Pyrazole-4-H),6.89(s,1H,NH),5.91(s,1H,Thiophene-H),4.38(t,2H,O-CH2),4.10-4.13 (m,2H,N-CH2),3.73(s,3H,N-CH3).
Compound 21-78:δ(CDCl3):8.50(s,1H,Pyrimidine-H),7.71-7.73(d,2H,Ph-2,6- 2H),7.20-7.23(d,2H,Ph-3,5-2H),7.11(s,1H,Pyrazole-4-H),6.89(s,1H,NH),5.84(s, 1H,Thiophene-H),4.37(t,2H,O-CH2),4.09-4.12(m,2H,N-CH2),3.72(s,3H,N-CH3).
Meanwhile it corresponding raw material is replaced according to the content described in above-mentioned each synthetic example can obtain this hair Other compounds shown in bright general formula I.
In addition, above-mentioned acquisition compound is reacted in a conventional manner with acid, and then obtain corresponding salt.
Biological activity determination embodiment
The compounds of this invention shows good activity to a variety of germs in agriculture field.
Embodiment 8：Bactericidal activity measures
With the compounds of this invention sample a variety of fungal diseases of plant have been carried out with Antifungal Activity in Vitro or live body protection effect Fruit is tested.Bactericidal activity measurement result is shown in following embodiment.
(1) in vitro bactericidal activity measures
Assay method is as follows：Using high-throughput screening method, i.e., by test compound sample with suitable solvent (solvent Species such as acetone, methanol, DMF etc., and selected according to its solvability to sample) dissolving, it is configured to required concentration and treats Survey liquid.Under ultra-clean working environment, prepare liquid is added in the micropore of 96 well culture plates, then pathogen is bred into liquid suspension It is added thereto, treated, and culture plate is placed in constant incubator cultivates.24 it is small when after investigated, when investigation, estimates cause of disease Bacterium brood body sprouts or growing state, and the sprouting according to control treatment or growing state, evaluates compound bacteriostatic activity.
The Antifungal Activity in Vitro of part of compounds (represents) that test result is as follows with inhibiting rate：
To the inhibiting rate of Pyricularia oryzae：
Under 25ppm dosage, compound 10-19,11-19,19-19,21-19,11-1-1,12-1-1 etc., to rice blast Inhibiting rate more than 80%；And comparison medicament CK1, CK2, CK3, CK4 and CK5 are 0 to the inhibiting rate of rice blast.
(2) live body protection activity measures
Assay method is as follows：Using live body potting assay method, i.e., by test compound sample with a small amount of solvent (solvent Species such as acetone, methanol, DMF etc., and selected, the volume ratio of quantity of solvent and spouting liquid according to its solvability to sample It equal to or less than 0.05) dissolving, is diluted with the water containing 0.1% Tween 80, is configured to required concentration prepare liquid.It sprays in crop On machine, prepare liquid is sprayed on disease host plant (host plant is the standard Potted orchard cultivated in greenhouse), 24 it is small when Disease inoculation is carried out afterwards.According to disease feature, it would be desirable to be placed on phjytotron after the disease plant inoculating of temperature control moisturizing culture Middle culture after disease completion is infected, moves into hot-house culture, the disease plant that moisturizing culture is not required directly is inscribed in greenhouse It plants and cultivates.(being usually week age) carries out compound protection effect assessment after fully morbidity is compareed.
The live body protection activity test result of part of compounds is as follows：
To the live body protection activity of cucumber downy mildew：
Under 400ppm dosage, compound 11-19,11-1-1,12-1-1 etc., to cucumber downy mildew 80% with
On；Under 100ppm dosage, compound 11-1-1,12-1-1 etc., to cucumber downy mildew more than 80%.
To the live body protection activity of corn rust：
Under 400ppm dosage, compound has：10-19,11-19,11-1-1,12-1-1 etc. exist to corn rust preventive effect More than 80%.
Mode according to above-mentioned biological activity determination surveys other compounds shown in general formula I of the present invention accordingly Examination can also have corresponding activity.

Claims (10)

1. a kind of substituted pyrazolecarboxylic class compound containing pyrimidine, it is characterised in that：Substituted pyrazolecarboxylic class compound containing pyrimidine is general formula I Shown compound；
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C3-C12Cycloalkyl, 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-C12Alkylthio 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 R2Five yuan, hexa-atomic, seven yuan or octatomic ring containing C, N, O or S can also 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-C12Cycloalkyl, 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 substituted 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 is 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-C8Cycloalkyl, 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-C12Cycloalkyl, 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；
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-C8Cycloalkyl, C1-C12Alkoxy, C1-C12Alkylthio group or C1-C12Alkyl sulphonyl；
Q is selected from unsubstituted or by 1-5 R10It is substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, miscellaneous Aryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
Or the salt of compound shown in general formula I.
2. the substituted pyrazolecarboxylic class compound according to claim 1 containing pyrimidine, it is characterised in that：The compound of Formula I In：
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Cycloalkyl, 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 R2Five yuan or hexatomic ring containing C, N, O or S can also 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- C6Cycloalkyl, 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 of lower group substitution1-C6Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C6Alkyloxycarbonyl, aryl C1- C6Alkyl, Heteroarylcarbonyl C1-C6Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C6Alkyloxycarbonyl, heteroaryl Base C1-C6Alkyl, following group is halogen, nitro, cyano, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy is 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-C6Cycloalkyl, 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-C6Cycloalkyl, 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；
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-C6Cycloalkyl, C1-C6Alkoxy, C1-C6Alkylthio group or C1- C6Alkyl sulphonyl；
Q is selected from unsubstituted or by 1-5 R10It is substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, miscellaneous Aryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl.
3. the substituted pyrazolecarboxylic class compound according to claim 2 containing pyrimidine, it is characterised in that：Q is selected from the general formula I It is unsubstituted or by 1-5 R10Substituted aryl, the structural formula of compound formula I is as shown in I-1；
In formula,
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Cycloalkyl, 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 R2Five yuan or hexatomic ring containing C, N, O or S can also 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- C4Cycloalkyl, 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 of lower group substitution1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkyloxycarbonyl, aryl C1- C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C4Alkyloxycarbonyl, heteroaryl Base C1-C4Alkyl, following group is halogen, nitro, cyano, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy is 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-C4Cycloalkyl, 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-C4Cycloalkyl, 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；
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-C4Cycloalkyl, C1-C4Alkoxy, C1-C4Alkylthio group or C1- C4Alkyl sulphonyl.
4. the substituted pyrazolecarboxylic class compound according to claim 3 containing pyrimidine, it is characterised in that：Shown in the general formula I-1 The structure of compound is：I-1A, I-1B, I-1C or I-1D；
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-C4Cycloalkyl, 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 more 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-C4Cycloalkyl, C1-C4Alkoxy, C1-C4Alkylthio group or C1- C4Alkyl sulphonyl；
And when the compound is general formula I-1D, X is O or S；
When the compound is general formula I-1A and I-1D,
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Cycloalkyl, 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-1A, I-1B and I-1C,
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alkoxy, C3- C4Cycloalkyl, 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 of lower group substitution1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkyloxycarbonyl, aryl C1- C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C4Alkyloxycarbonyl, heteroaryl Base C1-C4Alkyl, following group is halogen, nitro, cyano, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy is halogenated C1-C4Alkoxy；
When the compound is general formula I-1B,
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-C4Cycloalkyl；
When the compound is general formula I-1C,
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 cycloalkyl, unsubstituted or by 1-5 R10Substituted virtue Base, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl Carbonyl or Heteroaryloxycarbonyl.
5. the substituted pyrazolecarboxylic class compound according to claim 4 containing pyrimidine, it is characterised in that：General formula I-1A, I-1B, I- In compound shown in 1C, I-1D：
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, tertiary 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, tertiary 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, tertiary 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 more 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, tertiary 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-1A and I-1D,
R1Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, carboxyl, methyl, ethyl, n-propyl, isopropyl, normal-butyl, secondary Butyl, isobutyl group, tertiary 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-1A, I-1B and I-1C,
R3Selected from hydrogen, hydroxyl, formoxyl, acetyl group, propiono, bytyry, trifluoroacetyl group, benzoyl, methyl, ethyl, just Propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, trifluoro Ethyoxyl, cyclopropyl oxygroup, methyl mercapto, ethylmercapto group, pi-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-1B,
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, tertiary 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-1C,
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, tertiary 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. the substituted pyrazolecarboxylic class compound according to claim 5 containing pyrimidine, it is characterised in that：General formula I-1A, I-1B, I- In compound shown in 1C, I-1D：
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 more 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-1A and I-1D,
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-1A, I-1B and I-1C,
R3Selected from hydrogen, methyl, acetyl group, trifluoroacetyl group, methoxyl group, methyl mercapto, pi-allyl, mesyl, methylamino sulphonyl Base, dimethylaminosulfonyl, methoxycarbonyl, amino-carbonyl, dimethyl-aminocarbonyl, methylamino sulfenyl or dimethylamino sulphur Base；
When the compound is general formula I-1B,
R13、R14、R15Or R16Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl；
When the compound is general formula I-1C,
R17、R18Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine or iodine.
7. the substituted pyrazolecarboxylic class compound according to claim 6 containing pyrimidine, it is characterised in that：General formula I-1A, I-1B, I- In compound shown in 1C, I-1D：
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 more 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-1A and I-1D,
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-1A, I-1B and I-1C,
R3Selected from hydrogen, methyl, acetyl group, methoxyl group, pi-allyl, mesyl, methoxycarbonyl, amino-carbonyl, dimethylamino Carbonyl or dimethylamino sulfenyl；
When the compound is general formula I-1B,
R13、R14、R15、R16It is selected from hydrogen；
When the compound is general formula I-1C,
R17Selected from hydrogen；
R18Selected from chlorine.
8. a kind of preparation method by the substituted pyrazolecarboxylic class compound described in claim 1 containing pyrimidine, it is characterised in that：General formula The preparation method of compound shown in I is：
9. a kind of substituted pyrazolecarboxylic class compound described in accordance with the claim 1 containing pyrimidine is used as making in agricultural or other field The purposes of standby fungicide drug.
10. a kind of bactericidal composition, it is characterised in that：Composition is with the substituted pyrazolecarboxylic class described in claim 1 containing pyrimidine Object is closed as active component；Wherein, the weight percentage of active component is 0.1-99% in composition.
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