CN109836417A - Substituted uracil compound and preparation method thereof and purposes as fungicide - Google Patents

Substituted uracil compound and preparation method thereof and purposes as fungicide Download PDF

Info

Publication number
CN109836417A
CN109836417A CN201711223040.2A CN201711223040A CN109836417A CN 109836417 A CN109836417 A CN 109836417A CN 201711223040 A CN201711223040 A CN 201711223040A CN 109836417 A CN109836417 A CN 109836417A
Authority
CN
China
Prior art keywords
alkyl
halogenated
carbonyl
alkoxy
amino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201711223040.2A
Other languages
Chinese (zh)
Inventor
关爱莹
李淼
王军锋
许磊川
孙芹
孙旭峰
孙金强
刘长令
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shenyang Sinochem Agrochemicals R&D Co Ltd
Original Assignee
Shenyang Sinochem Agrochemicals R&D Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shenyang Sinochem Agrochemicals R&D Co Ltd filed Critical Shenyang Sinochem Agrochemicals R&D Co Ltd
Priority to CN201711223040.2A priority Critical patent/CN109836417A/en
Priority to EP18882912.1A priority patent/EP3719015A4/en
Priority to CN201880064173.6A priority patent/CN111263757A/en
Priority to PCT/CN2018/116938 priority patent/WO2019105275A1/en
Priority to US16/766,925 priority patent/US11457628B2/en
Priority to BR112020010921A priority patent/BR112020010921A8/en
Publication of CN109836417A publication Critical patent/CN109836417A/en
Pending legal-status Critical Current

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of substituted uracil compounds, and structure is as shown in general formula I；Each substituent group is defined in the specification in formula.The compound of the present invention has broad spectrum antibacterial activity, has excellent control efficiency to cucumber downy mildew, powdery mildew, corn rust, anthracnose, rice blast etc..

Description

Substituted uracil compound and preparation method thereof and purposes as fungicide
Technical field
The invention belongs to chemical fields, and in particular to a kind of substituted uracil compound and preparation method thereof and as fungicide Purposes.
Background technique
Patent WO9507278 discloses substituted pyrazolecarboxylic class compound formula and materialization shown in following general formula containing pyrimidine Close object CK1 and CK2, the application as agricultural bactericidal, Insecticidal and acaricidal agent etc..
Through Scifinder online information retrieval to following compound CK3, CK4, CK5, but without particular reference.
But structure substituted uracil compound as shown in general formula I of the present invention has not been reported.
Summary of the invention
The purpose of the present invention is to provide a kind of substituted pyrazolecarboxylic class compounds containing pyrimidine that can control a variety of germs, and The purposes of preparation method and the drug for preparing 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 uracil compound, and the substituted uracil compound is the chemical combination as shown in general formula I Object,
In formula:
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C3-C12Cycloalkanes Base, C1-C12Alkoxy, halogenated C1-C12Alkoxy, C1-C12Alkylthio group, halogenated C1-C12Alkylthio group, C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphonyl, C2-C12Alkenyl, halogenated C2-C12Alkenyl, C2-C12Alkynyl, halogenated C2-C12Alkynyl, C3-C12Alkenyloxy group, Halogenated C3-C12Alkenyloxy group, C3-C12Alkynyloxy group, halogenated C3-C12Alkynyloxy group, C1-C12Alkyl amino, two (C1-C12Alkyl) amino, C1-C12Alkyl amino-carbonyl, halogenated C1-C12Alkyl amino-carbonyl, C1-C12Alkoxy carbonyl, halogenated C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl or C1-C2Alkylthio group C1-C12Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C1- C12Alkoxy or halogenated C1-C12Alkoxy；
R1And R2Also five yuan, hexa-atomic, seven yuan or octatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy, halogenated C1-C12Alkane Oxygroup, C3-C12Naphthenic base, C1-C12Alkylthio group, C2-C12Enylsulfanyl, C2-C12Alkenyl, C2-C12Alkynyl, halogenated C2-C12Alkenyl, Halogenated C2-C12Alkynyl, C1-C12Alkoxy C1-C12Alkyl, halogenated C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12 Alkyl, halogenated C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkyl sulphinyl, halogenated C1-C12Alkyl sulphinyl, C1-C12Alkane Base sulfonyl, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkyl amino sulfonyl, two (C1-C12Alkyl) amino-sulfonyl, C1- C12Alkylsulfonyl aminocarbonyl, C1-C12Alkyl-carbonyl-amino sulfonyl, C3-C12Cycloalkyloxycarbonyl, C1-C12Alkyl oxycarbonyl Base, halogenated C1-C12Alkyl-carbonyl, C1-C12Alkoxy carbonyl, halogenated C1-C12Alkoxy carbonyl, C1-C12Alkyl-carbonyl C1-C12 Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkyl amino-carbonyl, two (C1-C12Alkyl) amino carbonyl, C2-C12Alkene Epoxide carbonyl, C2-C12Alkynyloxycar bonyl, C1-C12Alkoxy C1-C12Alkoxy carbonyl, C1-C12Alkyl amino sulfenyl, two (C1- C12Alkyl) amino sulfenyl, the unsubstituted or aryl carbonyl C that are replaced by the following groups of 1-51-C6Alkyl, aryl carbonyl, virtue Epoxide carbonyl, aryl C1-C6Alkyloxycarbonyl, aryl C1-C6Alkyl, Heteroarylcarbonyl C1-C6It is alkyl, Heteroarylcarbonyl, miscellaneous Aryloxycarbonyl, heteroaryl C1-C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyl, following group are halogen, nitro, cyano, C1- C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy or Halogenated C1-C12Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C8Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy or Halogenated C1-C12Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C8Ring；
M is selected from 0 to 5 integer；
R8Selected from hydrogen, cyano, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy carbonyl, halogenated C1-C12 It is alkoxy carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxy group carbonyl Base, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C12Alkyl, C3-C8Naphthenic base, halogenated C1-C12Alkyl, C1-C12Alkyl-carbonyl, halogenated C1-C12 Alkyl-carbonyl, C1-C12Alkyl sulphonyl, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12 Alkyl, C1-C12Alkoxy carbonyl C1-C12It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, Arylmethyl carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy, halogen For C1-C12Alkoxy, C3-C12Naphthenic base, C1-C12Alkyl amino, halogenated C1-C12Alkyl amino, two (C1-C12Alkyl) amino, Halogenated two (C1-C12Alkyl) amino, C (=O) NR11R12、C1-C12Alkylthio group, halogenated C1-C12Alkylthio group, C2-C12Alkenyl, C2- C12Alkynyl, C2-C12Alkenyloxy group, halogenated C2-C12Alkenyloxy group, C2-C12Alkynyloxy group, halogenated C2-C12Alkynyloxy group, C1-C12Alkyl sulfonyl Base, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkyl-carbonyl, halogenated C1-C12Alkyl-carbonyl, C1-C12It is alkoxy carbonyl, halogenated C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl, halogenated C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1- C12Alkyl, halogenated C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, halogenated C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkylthiocarbonyl C1-C12Alkyl, halogenated C1-C12Alkylthiocarbonyl C1-C12Alkyl, C1-C12Alkyl oxycarbonyl Base oxygroup, halogenated C1-C12Alkyl carbonyl epoxide, C1-C12Alkoxy-carbonyl oxy, halogenated C1-C12Alkoxy-carbonyl oxy, C1- C12Alkyl sulphonyl oxygroup, halogenated C1-C12Alkyl sulphonyl oxygroup, C1-C12Alkoxy C1-C12Alkoxy or halogenated C1-C12Alkane Oxygroup C1-C12Alkoxy；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C3-C8Naphthenic base, C1-C12Alkoxy, C1-C12Alkane Sulfenyl or C1-C12Alkyl sulphonyl；
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.
In substituted uracil compound of the present invention, optional compound includes: in shown general formula I:
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Naphthenic base, C1-C6Alkoxy, halogenated C1-C6Alkoxy, C1-C6Alkylthio group, C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halogenated C1- C6Alkylthio group, C2-C6Alkenyl, halogenated C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6Alkynyl, C3-C6Alkenyloxy group, halogenated C3-C6Alkene Oxygroup, C3-C6Alkynyloxy group, halogenated C3-C6Alkynyloxy group, C1-C6Alkyl amino, two (C1-C6Alkyl) amino, C1-C6Alkyl amino carbonyl Base, halogenated C1-C6Alkyl amino-carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkoxy C1-C6Alkane Base or C1-C6Alkylthio group C1-C6Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6 Alkoxy or halogenated C1-C6Alkoxy；
R1And R2Also five yuan or hexatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy, halogenated C1-C6Alcoxyl Base, C3-C6Naphthenic base, C1-C6Alkylthio group, C2-C6Enylsulfanyl, C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6It is alkenyl, halogenated C2-C6Alkynyl, C1-C6Alkoxy C1-C6Alkyl, halogenated C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group C1-C6It is alkyl, halogenated C1-C6Alkylthio group C1-C6Alkyl, C1-C6Alkyl sulphinyl, halogenated C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halogen For C1-C6Alkyl sulphonyl, C1-C6Alkyl amino sulfonyl, two (C1-C6Alkyl) amino-sulfonyl, C1-C6Alkyl sulphonyl ammonia Base carbonyl, C1-C6Alkyl-carbonyl-amino sulfonyl, C3-C6Cycloalkyloxycarbonyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl Carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkyl-carbonyl C1-C6Alkyl, C1-C6Alkoxy carbonyl C1-C6Alkyl, C1-C6Alkyl amino-carbonyl, two (C1-C6Alkyl) amino carbonyl, C2-C6Allyloxycarbonyl, C2-C6Alkynyloxy group carbonyl Base, C1-C6Alkoxy C1-C6Alkoxy carbonyl, C1-C6Alkyl amino sulfenyl, two (C1-C6Alkyl) amino sulfenyl, it is unsubstituted or The aryl carbonyl C being further substituted with by 1-5 following groups1-C6Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C6Alkane Base Epoxide carbonyl, aryl C1-C6Alkyl, Heteroarylcarbonyl C1-C6Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1- C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyl, following group are halogen, nitro, cyano, C1-C6Alkyl, halogenated C1-C6Alkane Base, C1-C6Alkoxy or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy or halogen For C1-C6Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C6Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy or halogen For C1-C6Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C6Ring；
M is selected from 0 to 4 integer；
R8Selected from hydrogen, cyano, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkane It is Epoxide carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, Heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C6Alkyl, C3-C6Naphthenic base, halogenated C1-C6Alkyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl Carbonyl, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkyl sulphonyl, C1-C6Alkoxy carbonyl, C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkoxy carbonyl C1-C6It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl Carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6It is alkoxy, halogenated C1-C6Alkoxy, C3-C6Naphthenic base, C1-C6Alkyl amino, halogenated C1-C6Alkyl amino, two (C1-C6Alkyl) amino, halogenated two (C1-C6Alkyl) amino, C (=O) NR11R12、C1-C6Alkylthio group, halogenated C1-C6Alkylthio group, C2-C6Alkenyl, C2-C6Alkynyl, C2- C6Alkenyloxy group, halogenated C2-C6Alkenyloxy group, C2-C6Alkynyloxy group, halogenated C2-C6Alkynyloxy group, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkane Base sulfonyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1- C6Alkoxy C1-C6Alkyl, halogenated C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group C1-C6Alkyl, halogenated C1-C6Alkylthio group C1-C6Alkyl, C1-C6Alkoxy carbonyl C1-C6Alkyl, halogenated C1-C6Alkoxy carbonyl C1-C6Alkyl, C1-C6Alkylthiocarbonyl C1-C6Alkyl, halogenated C1-C6Alkylthiocarbonyl C1-C6Alkyl, C1-C6Alkyl carbonyl epoxide, halogenated C1-C6Alkyl carbonyl epoxide, C1-C6Alkoxy-carbonyl oxy, halogenated C1-C6Alkoxy-carbonyl oxy, C1-C6Alkyl sulphonyl oxygroup, halogenated C1-C6Alkyl sulphur Acyloxy, C1-C6Alkoxy C1-C6Alkoxy or halogenated C1-C6Alkoxy C1-C6Alkoxy；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Naphthenic base, C1-C6Alkoxy, C1-C6Alkylthio group Or C1-C6Alkyl sulphonyl；
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.
In substituted uracil compound of the present invention, more optional compound includes that Q is selected from unsubstituted in the general formula I Or by 1-5 R10Substituted aryl, the structural formula of compound formula I are further as shown in I-1；
In formula,
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, halogenated C1-C4Alkoxy, C1-C4Alkylthio group, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogenated C1- C4Alkylthio group, C2-C4Alkenyl, halogenated C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkynyl, C3-C4Alkenyloxy group, halogenated C3-C4Alkene Oxygroup, C3-C4Alkynyloxy group, halogenated C3-C4Alkynyloxy group, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl amino carbonyl Base, halogenated C1-C4Alkyl amino-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkane Base or C1-C4Alkylthio group C1-C4Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4 Alkoxy or halogenated C1-C4Alkoxy；
R1And R2Also five yuan or hexatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alcoxyl Base, C3-C4Naphthenic base, C1-C4Alkylthio group, C2-C4Enylsulfanyl, C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4It is alkenyl, halogenated C2-C4Alkynyl, C1-C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4It is alkyl, halogenated C1-C4Alkylthio group C1-C4Alkyl, C1-C4Alkyl sulphinyl, halogenated C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogen For C1-C4Alkyl sulphonyl, C1-C4Alkyl amino sulfonyl, two (C1-C4Alkyl) amino-sulfonyl, C1-C4Alkyl sulphonyl ammonia Base carbonyl, C1-C4Alkyl-carbonyl-amino sulfonyl, C3-C4Cycloalkyloxycarbonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl Carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, C2-C4Allyloxycarbonyl, C2-C4Alkynyloxy group carbonyl Base, C1-C4Alkoxy C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or The aryl carbonyl C being further substituted with by 1-5 following groups1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkane Base Epoxide carbonyl, aryl C1-C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1- C4Alkyloxycarbonyl, heteroaryl C1-C4Alkyl, following group are halogen, nitro, cyano, C1-C4Alkyl, halogenated C1-C4Alkane Base, C1-C4Alkoxy or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy or halogen For C1-C4Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C4Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy or halogen For C1-C4Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C4Ring；
M is selected from 0 to 3 integer；
R8Selected from hydrogen, cyano, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkane It is Epoxide carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, Heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C4Alkyl, C3-C4Naphthenic base, halogenated C1-C4Alkyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl Carbonyl, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkyl sulphonyl, C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl Carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4It is alkoxy, halogenated C1-C4Alkoxy, C3-C4Naphthenic base, C1-C4Alkyl amino, halogenated C1-C4Alkyl amino, two (C1-C4Alkyl) amino, halogenated two (C1-C4Alkyl) amino, C (=O) NR12R13、C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C2-C4Alkenyl, C2-C4Alkynyl, C2- C4Alkenyloxy group, halogenated C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halogenated C2-C4Alkynyloxy group, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkane Base sulfonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1- C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkylthio group C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, halogenated C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkylthiocarbonyl C1-C4Alkyl, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4Alkoxy-carbonyl oxy, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphur Acyloxy, C1-C4Alkoxy C1-C4Alkoxy or halogenated C1-C4Alkoxy C1-C4Alkoxy；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, C1-C4Alkylthio group Or C1-C4Alkyl sulphonyl.
Or the salt of compound shown in general formula I.
In substituted uracil compound of the present invention, further alternative compound includes compound shown in the general formula I-1 Structure are as follows: 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-C4Naphthenic base, C1-C4Alkyl amino, halogenated C1-C4Alkyl amino, two (C1-C4Alkyl) amino, halogenated two (C1-C4Alkyl) amino, C (=O) NR11R12、C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C2-C4Alkenyl, C2-C4Alkynyl, C2- C4Alkenyloxy group, halogenated C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halogenated C2-C4Alkynyloxy group, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkane Base sulfonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1- C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkylthio group C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, halogenated C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkylthiocarbonyl C1-C4Alkyl, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4Alkoxy-carbonyl oxy, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphur Acyloxy, C1-C4Alkoxy C1-C4Alkoxy or halogenated C1-C4Alkoxy C1-C4Alkoxy；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It is identical or different；
R11、R12Identical or different is respectively selected from hydrogen, C1-C4Alkyl or halogenated C1-C4Alkyl；
W is selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, C1-C4Alkylthio group Or C1-C4Alkyl sulphonyl；
And when the compound is general formula I-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-C4Naphthenic base, C1-C4Alkoxy, halogenated C1-C4Alkoxy, C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C1-C4Alkyl sulphinyl, C1-C4Alkane Base sulfonyl, C2-C4Alkenyl, halogenated C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkynyl, C3-C4Alkenyloxy group, halogenated C3-C4Alkene Oxygroup, C3-C4Alkynyloxy group, halogenated C3-C4Alkynyloxy group, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl amino carbonyl Base, halogenated C1-C4Alkyl amino-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkane Base or C1-C4Alkylthio group C1-C4Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4 Alkoxy or halogenated C1-C4Alkoxy；
When the compound is general formula I-1A, I-1B and I-1C,
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alcoxyl Base, C3-C4Naphthenic base, C1-C4Alkylthio group, C2-C4Enylsulfanyl, C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4It is alkenyl, halogenated C2-C4Alkynyl, C1-C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4It is alkyl, halogenated C1-C4Alkylthio group C1-C4Alkyl, C1-C4Alkyl sulphinyl, halogenated C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogen For C1-C4Alkyl sulphonyl, C1-C4Alkyl amino sulfonyl, two (C1-C4Alkyl) amino-sulfonyl, C1-C4Alkyl sulphonyl ammonia Base carbonyl, C1-C4Alkyl-carbonyl-amino sulfonyl, C3-C4Cycloalkyloxycarbonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl Carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, C2-C4Allyloxycarbonyl, C2-C4Alkynyloxy group carbonyl Base, C1-C4Alkoxy C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or The aryl carbonyl C being further substituted with by 1-5 following groups1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkane Base Epoxide carbonyl, aryl C1-C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1- C4Alkyloxycarbonyl, heteroaryl C1-C4Alkyl, following group are halogen, nitro, cyano, C1-C4Alkyl, halogenated C1-C4Alkane Base, C1-C4Alkoxy or halogenated C1-C4Alkoxy；
When the compound is general formula I-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-C4Naphthenic base；
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 naphthenic base, unsubstituted or by 1-5 R10Replace Aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroaryl Methyl carbonyl or Heteroaryloxycarbonyl；
When the compound is general formula I-1C,
X is O or S；
Or the salt of compound shown in general formula I.
In substituted pyrazolecarboxylic class compound of the present invention containing pyrimidine, further optional compound includes, general formula I-1A, In compound shown in I-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, tert-butyl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, different Butoxy or tert-butoxy；
R6、R7Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, positive fourth It is base, sec-butyl, isobutyl group, tert-butyl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, different Butoxy or tert-butoxy；
R8、R9Identical or different is respectively selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, normal-butyl, Zhong Ding Base, isobutyl group, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, one methyl fluoride of dichloro, methoxyl group, ethyoxyl, just Propoxyl group, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methyl mercapto, ethylmercapto group, trifluoromethoxy, Trifluoro ethoxy, methoxycarbonyl, ethoxy carbonyl, amino carbonyl, methylaminocarbonyl, ethyl aminocarbonyl or dimethylamino Carbonyl；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary fourth Base, a methyl fluoride, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, methyl mercapto, ethylmercapto group, Methyl sulphonyl or ethylsulfonyl；
And when the compound is general formula I-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, tert-butyl, a methyl fluoride, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy methyl Base, ethoxyl methyl or trifluoroethoxy ylmethyl；
R2Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, carboxyl, formoxyl, methyl, ethyl, methoxyl group, ethoxy Base or trifluoro ethoxy；
When the compound is general formula I-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, tert-butyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, Trifluoro ethoxy, cyclopropyl oxygroup, methyl mercapto, ethylmercapto group, allyl, propargyl, mesyl, ethylsulfonyl, trifluoroethyl Sulfonyl, aminosulfonyl, ethylamino sulfonyl, dimethylaminosulfonyl, lignocaine sulfonyl, methane sulfonylamino carbonyl Base, methoxycarbonyl, ethoxy carbonyl, propoxycarbonyl, isopropoxy carbonyl, amino-carbonyl, dimethyl-aminocarbonyl, ethylene Epoxide carbonyl, acetylene Epoxide carbonyl, methylamino sulfenyl, ethylamino sulfenyl or dimethylamino sulfenyl；
When the compound is general formula I-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, tert-butyl, trifluoromethyl, trichloromethyl, one chloromethane of difluoro Base, one methyl fluoride of dichloro, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, uncle Butoxy, trifluoromethoxy or trifluoro ethoxy；
When the compound is general formula I-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, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, one methyl fluoride of dichloro, trifluoroethyl, Methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoro methoxy It is base, trifluoro ethoxy, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxy group Carbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
Or the salt of compound shown in general formula I.
In substituted uracil compound of the present invention, further optional compound includes, general formula I-1A, I-1B, I-1C, In compound shown in 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 greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl；
And when the compound is general formula I-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, 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；
Or the salt of compound shown in general formula I.
In substituted uracil compound of the present invention, more optional compound includes: general formula I-1A, I-1B, I-1C, I-1D In shown compound:
R4、R5It may be the same or different, be respectively selected from hydrogen or methyl；
R6、R7It is selected from hydrogen；
R8For hydrogen or methyl；
R9Selected from methyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxyl group, methyl mercapto or fluoroform Oxygroup；
N is selected from 1 to 5 integer, when n is greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine or iodine；
And when the compound is general formula I-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, 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；
Or the salt of compound shown in general formula I.
A kind of preparation method of substituted uracil compound, compound shown in general formula I the preparation method comprises the following steps:
Substituted uracil compound shown in a kind of above-mentioned general formula I is used as in agricultural or other field prepares fungicide medicine The purposes of object.
A kind of bactericidal composition, composition is using substituted uracil compound shown in above-mentioned general formula I as active component；Its In, the weight percentage of active component is 0.1-99% in composition.
In the definition of compound of Formula I given above, collects term used and is generally defined as follows:
Halogen: refer to fluorine, chlorine, bromine or iodine.Alkyl: linear or branched alkyl group, such as methyl, ethyl, propyl, isopropyl, just Butyl or tert-butyl.Naphthenic base: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopenta or cyclohexyl.Substituent group is such as Methyl, halogen etc..Halogenated alkyl: linear or branched alkyl group, the hydrogen atom on these alkyl can be partly or entirely by halogen atom It is replaced, for example, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl etc..Alkyl sulphinyl: Linear or branched alkyl group is connected in structure through sulfinyl (- SO-), such as methylsulfinyl.Alkylsulfinyl: straight Chain or branched alkyl sulfinyl, the hydrogen atom on alkyl can be partly or entirely replaced halogen atom.Halogenated alkyl sulphonyl Base: linear or branched alkyl group sulfonyl, the hydrogen atom on alkyl can be partly or entirely replaced halogen atom.Alkyl amino sulphur Base: such as CH3NHS-、C2H5NHS-.Dialkyl amido sulfenyl: such as (CH3)2NS-、(C2H5)2NS-.Alkyl amino sulfonyl: alkyl- NH-SO2-.Dialkyl amino sulfonyl: (alkyl)2-N-SO2-.Alkylsulfonyl aminocarbonyl: alkyl-SO2-NH-CO-.Alkane Base carbonylamino sulfonyl: alkyl-CO-NH-SO2-.Alkylcarbonylalkyl: alkyl-CO- alkyl-.Alkyl sulphonyl oxygroup: Alkyl-S (O)2-O-.Halogenated alkyl sulfonyl oxygroup: hydrogen atom on the alkyl of alkyl sulphonyl oxygroup can part or all of quilt Replaced halogen atom, such as CF3-SO2-O.Cycloalkyloxycarbonyl: such as cyclopropyl Epoxide carbonyl, cyclohexyloxy carbonyl.Alcoxyl Base: linear or branched alkyl group is keyed in structure through oxygen atom.Halogenated alkoxy: straight or branched alkoxyl, in these alkane Hydrogen atom in oxygroup can be partly or entirely replaced halogen atom.For example, chloromethane epoxide, dichloro methoxyl group, trichloromethoxy, Fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group, trifluoro ethoxy etc..Halo alkoxy carbonyl: alkoxy Hydrogen atom on the alkyl of carbonyl can be partly or entirely replaced halogen atom, such as ClCH2CH2OCO-、 CF3CH2OCO- etc..Alkane Oxygroup alkyl: alkyl-O- alkyl-, such as CH3OCH2-.Halogenated alkoxy alkyl: the hydrogen atom on the alkyl of alkoxyalkyl can Partly or entirely replaced halogen atom, such as ClCH2CH2OCH2-、 CF3CH2OCH2Etc..Alkoxy carbonyl alkyl: alkoxy carbonyl Base-alkyl-, such as CH3OCOCH2-.Halo alkoxy carbonyl alkyl: the hydrogen atom on the alkyl of alkoxy carbonyl alkyl can portion Point or all replaced halogen atom, such as CF3CH2OCOCH2-.Alkyl carbonyl epoxide: such as CH3COO- etc..Halogenated alkyl carbonyl Base oxygroup: the hydrogen atom of alkyl carbonyl epoxide can be partly or entirely replaced halogen atom, such as CF3COO- etc..Alkoxy carbonyl Oxygroup: alkoxy carbonyl-oxygroup-, such as CH3OCOO-.Halo alkoxy carbonyl oxygroup: on the alkyl of alkoxy-carbonyl oxy Hydrogen atom can be partly or entirely replaced halogen atom, such as CF3OCOO-.Alkylthiocarbonyl alkyl: alkylthiocarbonyl-alkane Base-, such as CH3SCOCH2-.Halogenated alkylthio carbonylic alkyl: the hydrogen atom on the alkyl of alkylthiocarbonyl alkyl can part or complete Portion is replaced halogen atom, such as CF3CH2SCOCH2-.Alkyloxy-alkoxy: such as CH3OCH2O- etc..Halogenated alkoxy alkoxy: Hydrogen atom on alkoxy can be partly or entirely replaced halogen atom, such as CF3OCH2O-.Alkoxyalkoxycarbonyl: such as CH3OCH2CH2OCO- etc..Alkylthio group: linear or branched alkyl group is keyed in structure through sulphur atom.Halogenated alkylthio: straight chain Or branched alkylthio, the hydrogen atom on these alkyl can be partly or entirely replaced halogen atom.For example, chloromethane sulfenyl, two Chloromethane sulfenyl, trichloro-methylthio, fluorine methyl mercapto, difluoro methyl mercapto, trifluoromethylthio, chlorine fluorine methyl mercapto etc..Alkylthio alkyl: alkane Base-S- alkyl-, such as CH3SCH2-.Haloalkylthioalkyl: the hydrogen atom on the alkyl of alkylthio alkyl can be part or all of Replaced halogen atom, such as ClCH2CH2SCH2-、 CF3CH2SCH2Etc..Alkyl amino: linear or branched alkyl group, through nitrogen-atoms It is keyed in structure.Haloalkylamino: linear or branched alkyl group amino, the hydrogen atom on these alkyl can part or complete Portion is replaced halogen atom.Dialkyl amido: such as (CH3)2N-, (CH3CH2)2N-.Halogenated dialkyl amido: the hydrogen on alkyl is former Son can be partly or entirely replaced halogen atom, such as (CF3)2N-, (CF3CH2)2N-.Alkenyl: linear chain or branched chain alkenes, such as second Alkenyl, 1- acrylic, 2- acrylic and different cyclobutenyls, pentenyl and hexenyl isomers.Alkenyl further includes polyenoid class, such as 1,2- allene base and 2,4- hexadienyl.Halogenated alkenyl: linear chain or branched chain alkenes, the hydrogen atom on these alkenyls can part Or all replaced halogen atom.Alkenyloxy group: linear chain or branched chain alkenes are keyed in structure through oxygen atom.Haloalkenyloxy: Linear chain or branched chain alkenyloxy group, the hydrogen atom in these alkenyloxy groups can be partly or entirely replaced halogen atom.Enylsulfanyl: straight Chain or branch chain alkene, are keyed in structure through sulphur atom.Such as CH2=CHCH2S-.Allyloxycarbonyl: such as CH2=CHCH2OCO- Deng.Alkynyl: linear chain or branched chain acetylenic, such as acetenyl, 1- propinyl, 2-propynyl and different butynyls, pentynyl and oneself Alkynyl isomers.Alkynyl further includes the group being made of multiple three keys, such as 2,5- adipic alkynyl.Halo alkynyl: linear chain or branched chain Acetylenic, the hydrogen atom on these alkynyls can be partly or entirely replaced halogen atom.Alkynyloxy group: linear chain or branched chain acetylenic, warp Oxygen atom is keyed in structure.Halogenated alkynyloxy group: linear chain or branched chain alkynyloxy group, the hydrogen atom on these alkynyloxy groups can part Or all replaced halogen atom.Alkynyloxycar bonyl: such as CH ≡ CCH2OCO- etc..Alkyl sulphonyl: linear or branched alkyl group warp Sulfonyl (- SO2) be connected in structure, such as methyl sulphonyl.Halogenated alkyl sulfonyl: linear or branched alkyl group sulfonyl, Hydrogen atom on alkyl can be partly or entirely replaced halogen atom.Alkyl-carbonyl: alkyl is connected in structure through carbonyl, such as CH3CO-, CH3CH2CO-.Halogenated alkyl carbonyl: the hydrogen atom on the alkyl of alkyl-carbonyl can partly or entirely be taken by halogen atom Generation, such as CF3CO-.Alkoxy carbonyl: alkoxy is connected in structure through carbonyl.Such as CH3OCO-, CH3CH2OCO-.Amino carbonyl: Such as NH2CO-.Alkyl amino-carbonyl: alkyl-NH-CO-, such as CH3NHCO-, CH3CH2NHCO-.Dialkyl amino carbonyl: such as (CH3)2NCO-, (CH3CH2)2NCO-.(miscellaneous) aryl, (miscellaneous) aryl alkyl, (miscellaneous) aryl carbonyl, (miscellaneous) arylmethyl carbonyl, (miscellaneous) aryl alkyl carbonyl, (miscellaneous) aryloxycarbonyl, the aryl moiety in (miscellaneous) aryl alkyl Epoxide carbonyl include phenyl or naphthalene Base etc..Heteroaryl is containing the heteroatomic five-membered ring of one or more N, O, S or hexatomic ring.Such as furyl, pyrazolyl, thiazolyl, Pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, quinolyl etc..(miscellaneous) aryl: such as phenyl.(miscellaneous) aryl alkyl: such as Benzyl, phenethyl, to chlorophenylmethyl, 2- chloropyridine -5- base, the chloro- thiazole -5- base of 2- etc..(miscellaneous) aryl carbonyl: such as benzoyl Base, 4- chlorobenzene formacyl etc..(miscellaneous) arylmethyl carbonyl: such as PhCH2CO-.(miscellaneous) aryl alkyl carbonyl: such as PhCOCH2-.(miscellaneous) Aryloxycarbonyl: such as phenyloxycarbonyl, 4- cHorophenoxycarbonyl, 4-nitrophenoxy carbonyl, naphthoxycarbonyl.Aryl alkyl Epoxide carbonyl: such as benzyloxycarbonyl, 4- chlorobenzyl Epoxide carbonyl, 4- trifluoromethyl benzyl Epoxide carbonyl.(miscellaneous) aryl alkane Base Epoxide carbonyl: such as PhCH2OCO-、4-Cl-PhCH2OCO- etc..
Table 1, table 2, table 3, table 4, table 5, table 6, table 7, table 8 list R in general formula I respectively1、R2、R3(X=NR3)、R4With R5、R6And R7、R8、R9, W the specific substituent group in part, but they are not limited only to these substituent groups.
1 R of table1Substituent group
2 R of table2Substituent 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
3 R of table3Substituent group
4 R of table4(R5) substituent group
5 R of table6(R7) substituent group
6 R of table8Substituent group
R8 R8 R8 R8
H CN CH3 C2H5
n-C3H7 i-C3H7 n-C4H9 s-C4H9
i-C4H9 t-C4H9 CF3 CCl3
CHF2 CH2F CH2Cl CH2CF3
CF2CF3 COOCH3 Ph Ph-4-Cl
7 R of table9Substituent group
8 W substituent group of table
Part of compounds of the invention can be illustrated with the particular compound listed in 9-table of table 32, but not limited The present invention.In general formula compound I-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, and representation compound number is followed successively by 9-4- 1—9-4-279。
10: in general formula I-1A, working 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, and representation compound number is followed successively by 10-1- 10-279。
10-1: in general formula I-1A, work as R1=CH3、R2=Cl, R3=R4=R5=H, R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 10-1-1—10-1-279。
10-2: in general formula I-1A, work as R1=CH3、R2=Cl, R3=R4=R5=H, R8When=H, m=2, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 10-2- 1—10-2-279。
10-3: in general formula I-1A, work as R1=CH3、R2=Cl, R3=R4=R5=H, R8=CH3, when m=2, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 10-3-1—10-3-279。
10-4: in general formula I-1A, work as R1=CH3、R2=Cl, R3=R4=H, R5=R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 10-4-1—10-4-279。
11: in general formula I-1A, working 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, and representation compound number is followed successively by 11-1- 11-279。
11-1: in general formula I-1A, work as R1=C2H5、R2=Cl, R3=R4=R5=H, R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 11-1-1—11-1-279。
11-2: in general formula I-1A, work as R1=C2H5、R2=Cl, R3=R4=R5=H, R8When=H, m=2, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 11-2- 1—11-2-279。
11-3: in general formula I-1A, work as R1=C2H5、R2=Cl, R3=R4=R5=H, R8=CH3, when m=2, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 11-3-1—11-3-279。
11-4: in general formula I-1A, work as R1=C2H5、R2=Cl, R3=R4=H, R5=R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 11-4-1—11-4-279。
12: in general formula I-1A, working as R1=CHF2、R2=Cl, R3=R4=R5=H, R8When=H, m=1, substituent group (R10)n Consistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 12-1- 12-279。
12-1: in general formula I-1A, work as R1=CHF2、R2=Cl, R3=R4=R5=H, R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 12-1-1—12-1-279。
12-2: in general formula I-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。
12-3: in general formula I-1A, work as R1=CHF2、R2=Cl, R3=R4=R5=H, R8=CH3, when m=2, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 12-3-1—12-3-279。
12-4: in general formula I-1A, work as R1=CHF2、R2=Cl, R3=R4=H, R5=R8=CH3, when m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 12-4-1—12-4-279。
13: in general formula I-1A, working as R1=CF3、R2=Cl, R3=R4=R5=H, R8When=H, m=1, substituent group (R10)nWith Substituent group shown in table 9 is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 13-1- 13-279。
14: in general formula I-1A, working 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。
15: in general formula I-1A, working 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。
16: in general formula I-1A, working as R1=C2H5、R2=Cl, R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 16-1—16-279。
17: in general formula I-1A, working as R1=CHF2、R2=Cl, R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 17-1—17-279。
18: in general formula I-1A, working 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
19: in general formula I-1B, working as R3=R4=R5=H, R8When=H, m=1, substituent group (R10)nWith substituent group shown in table 9 Unanimously, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 19-1-19-279.
19-1: in general formula I-1B, work as R3=R4=R5=H, R8=CH3, when m=1, substituent group (R10)nReplace with shown in table 9 Base is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 19-1-1-19-1-279.
19-2: in general formula I-1B, work as R3=R4=R5=H, R8When=H, m=2, substituent group (R10)nReplace with shown in table 9 Base is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 19-2-1-19-2-279.
19-3: in general formula I-1B, work as R3=R4=R5=H, R8=CH3, when m=2, substituent group (R10)nReplace with shown in table 9 Base is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 19-3-1-19-3-279.
19-4: in general formula I-1B, work as R3=R4=H, R5=R8=CH3, when m=1, substituent group (R10)nIt is taken with 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 19-4-1-19-4-279.
20: in general formula I-1B, working as R3=R4=H, R5=CH3, R8When=H, m=1, substituent group (R10)nIt is taken with 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
21: in general formula I-1C, working 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.
21-1: in general formula I-1C, work as R3=R4=R5=H, R18=Cl, R8=CH3, when m=1, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 21-1-1-21- 1-279。
21-2: in general formula I-1C, work as R3=R4=R5=H, R18=Cl, R8When=H, m=2, substituent group (R10)nWith 9 institute of table Show that substituent group is consistent, substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 21-2-1-21-2- 279。
21-3: in general formula I-1C, work as R3=R4=R5=H, R18=Cl, R8=CH3, when m=2, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 21-3-1-21- 3-279。
21-4: in general formula I-1C, work as R3=R4=H, R18=Cl, R5=R8=CH3, when m=1, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 21-4-1-21- 4-279。
22: in general formula I-1C, working as R3=R4=R5=H, R18=CH3, 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 22-1-22-279.
23: in general formula I-1C, working as R3=R4=H, R5=CH3, R18=Cl, R8When=H, m=1, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 23-1-23- 279。
24: in general formula I-1C, working as R3=R4=H, R5=CH3, R18=CH3, R8When=H, m=1, substituent group (R10)nWith table 9 Shown substituent group is consistent, and substituent group is corresponding in turn to the 9-1-9-279 of table 9, and representation compound number is followed successively by 24-1-24- 279。
In general formula I-1D
25: in general formula I-1D, working as R1=CH3、R2=Cl, R3=R4=R5=H, X=O, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 25-1—25-279。
26: in general formula I-1D, working as R1=C2H5、R2=Cl, R3=R4=R5=H, X=O, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 26-1—26-279。
27: in general formula I-1D, working as R1=CHF2、R2=Cl, R3=R4=R5=H, X=O, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 27-1—27-279。
28: in general formula I-1D, working as R1=CH3、R2=Cl, R3=R4=R5=H, X=S, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 28-1—28-279。
29: in general formula I-1D, working as R1=C2H5、R2=Cl, R3=R4=R5=H, X=S, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 29-1—29-279。
30: in general formula I-1D, working as R1=CHF2、R2=Cl, R3=R4=R5=H, X=S, R8When=H, m=1, substituent group (R10)nConsistent with substituent group shown in table 9, substituent group is corresponding in turn to 9-1-9-279 of table 9, and representation compound number is followed successively by 30-1—30-279。
In general formula I-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 invention can illustrate with the salt for the particular compound listed in table 32, but and unlimited The fixed present invention.
32 part of compounds salt of table
The compounds of this invention is prepared in accordance with the following methods, and reaction equation is as follows, and each group unless otherwise stated defines together in formula Before:
The preparation of compound of Formula I is with the following method:
Reaction obtains compound of Formula I in suitable solvent under alkaline condition by intermediate II and III.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, Sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
React and carried out in suitable solvent, the optional tetrahydrofuran freely of suitable solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile, Toluene, dimethylbenzene, benzene, N,N-dimethylformamide, N-Methyl pyrrolidone, dimethyl sulfoxide, acetone or butanone etc..
Reaction temperature can be in room temperature between solvent boiling point temperature, and usually 20-100 DEG C.
Reaction time is 30 minutes to 20 hours, 1-10 hours usual.
Intermediate II part is commercially available, can also prepare by known method, referring for example to document JP2000007662, US4977264、US6090815、US20040092402、JP09124613、US5468751、US4985426、 US4845097、 Journal of the American Chemical Society(1957),79,1455、Journal of Chemical Society (1955), the method preparation p.3478-3481 described.
Intermediate III is the key intermediate for preparing compound of Formula I of the present invention, is prepared as follows:
Intermediate M1 and dimethyl carbonate at a suitable temperature, react 30 minutes to 20 hours in suitable solvent, Usually 1-10 hours, intermediate M2 is made, this step operation method reference Tetrahedron:Asymmetry, 24 (15-16), 925-936；2013 and Angewandte Chemie, International Edition, 53 (45), 12210-12213； 2014；M3 is made through electrophilic substitution reaction in M2, this step operation method reference Pest Management science, 66 (1), 2010,107-112；M3 is reacted with X1 again is made M4, this step operation method is referring to 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 preparation is logical The corresponding steps and relevant references of compound of formula I.
Reaction obtains general formula I-1 compound in suitable solvent under alkaline condition by intermediate II and III.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, Sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
React and carried out in suitable solvent, the optional tetrahydrofuran freely of suitable solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile, Toluene, dimethylbenzene, benzene, N,N-dimethylformamide, N-Methyl pyrrolidone, dimethyl sulfoxide, acetone or butanone etc..
Reaction temperature can be in room temperature between solvent boiling point temperature, and usually 20-100 DEG C.
Reaction time is 30 minutes to 20 hours, 1-10 hours usual.
Intermediate II part is commercially available, can also prepare by known method, referring for example to document JP2000007662, US4977264、US6090815、US20040092402、JP09124613、US5468751、US4985426、 US4845097、 Journal of the American Chemical Society(1957),79,1455、Journal of Chemical Society (1955), the method preparation p.3478-3481 described.
Intermediate III is the key intermediate for preparing general formula I-1 compound of the present invention, is prepared as follows:
Intermediate M1 and dimethyl carbonate at a suitable temperature, react 30 minutes to 20 hours in suitable solvent, Usually 1-10 hours, intermediate M2 is made, this step operation method reference Tetrahedron:Asymmetry, 24 (15-16), 925-936；2013 and Angewandte Chemie, International Edition, 53 (45), 12210-12213； 2014；M3 is made through electrophilic substitution reaction in M2, this step operation method reference Pest Management science, 66 (1), 2010,107-112；M3 is reacted with X1 again is made M4, this step operation method is referring to CN102584705A；Last M4 and corresponding Halide react III be made, this step operation method referring to US20100158860, WO2011133444 and Bioorganic&Medicinal Chemistry,20(20),6109-6122, 2012。
Although certain compounds disclosed in compound of Formula I and the prior art of the invention also belong to the substitution containing pyrimidine Pyrazole compound, but there are still dramatically different for structure feature.And made of the invention 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 harmful mite Show preferable activity.Therefore, technical solution of the present invention further includes that compound of Formula I 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 to illustrate the present invention, but never limits the present invention.
Compound of Formula I can be used for preventing and treating 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 (semen viciae fabae 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, as (sweet potato is withered for wilt disease Wither disease, cotton wilt, sesame wilt disease, castor-oil plant wilt disease, tomato wilt, Kidney bean wilt disease, cucumber fusarium axysporum, sponge gourd is withered Wither disease, pumpkin wilt disease, wax gourd wilt disease, 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, semen viciae fabae 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 carbonums, bluish dogbane waist folding disease, rice blast, the black sheath 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, semen viciae fabae 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, semen viciae fabae 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 compound 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 harmful mite.
To obtain ideal effect, the dosage of compound changes because of various factors, such as compound used therefor, the work protected in advance Object, the type of harmful organism, gradient of infection, weather conditions, application method, the dosage form of use.
10 grams -5 kilograms of per hectare of compound dosage can provide sufficient prevention and treatment.
The invention also includes the sterilizations using compound shown in general formula I as active component, 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.
Composition of the invention can be applied in the form of preparation.Compound shown in general formula I dissolves or divides as active component It is more readily dispersible when dissipating in carrier or being configured to preparation to use as sterilization, desinsection.Such as: these chemicals can quilt Wettable powder, oil suspending agent, aqueous suspension, aqueous emulsion, aqua or missible oil etc. is made.In these compositions, one kind is at least added Liquid or solid carrier, and surfactant appropriate can be added when needed.
Technical solution of the present invention further includes the method for anti-pathogen, pest harmful mite: by sterilization of the invention, Insecticiding-miticiding Composition imposes on the germ or its somatomedin.The more suitable effective amount generally selected is 10 grams of per hectare and arrives 1000 grams, preferably effective quantity is 20 grams to 500 grams of per hectare.
For certain applications, for example, can be agriculturally added in sterilization of the invention, 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 produce additional excellent Point and effect.
It should be appreciated that various transformation and change can be carried out in scope defined by the claims of the present invention.
Specific embodiment
Following specific embodiments be used to further illustrate the present invention, but the present invention is by no means limited to these examples (except as otherwise It is raw materials used to be commercially available outside indicating).
Synthetic example
Embodiment 1: the preparation of the chloro- 6- methylpyrimidine of intermediate 4,5- bis-
1) preparation of the chloro- 6- methylpyrimidine of 4- hydroxyl -5-
It is stirred at room temperature and lower 8.80g is slowly added dropwise into the 50ml methanol solution of 11.30g (0.11mol) formamidine acetate The methanol solution of (0.16mol) sodium methoxide drips complete room temperature and continues to stir 2h.It states then up and 11.17g is added dropwise in solution (0.068mol) intermediate 2- chloroacetyl acetacetic ester continues that reaction 5-7 hours is stirred at room temperature.TLC is monitored after completion of the reaction, is subtracted Solvent is evaporated off in pressure, with hydrochloric acid tune pH=5~6, filters to obtain orange/yellow solid, water phase is extracted with (3 × 50ml) ethyl acetate, anhydrous Magnesium sulfate is dry, filters, precipitation.Residue is dissolved in 50ml ethyl acetate, is stood overnight, and orange/yellow solid 6.48g is filtered to obtain. Yield 66%, 181~184 DEG C of fusing point.
2) preparation of the chloro- 6- methylpyrimidine of 4,5- bis-
The chloro- 6- methylpyrimidine of 14.5g (0.1mol) 4- hydroxyl -5- is dissolved in 50ml toluene solution, to reaction under stirring 50ml phosphorus oxychloride is instilled in bottle, is dripped and is finished temperature rising reflux reaction 5-7 hours.TLC monitor after completion of the reaction, remove under reduced pressure toluene and Reactant, is poured into ice water by excessive phosphorus oxychloride under stirring, and water phase is extracted with (3 × 50ml) ethyl acetate, merges organic Phase, anhydrous magnesium sulfate is dry, filters, precipitation.Residue column chromatography (eluant, eluent be ethyl acetate and petroleum ether, volume ratio 1: 5) yellow liquid 14.43g, yield 88.5% are separated to obtain.
The preparation of embodiment 2:4,5- dichloro-thiophene simultaneously [2,3-d] pyrimidine
Take 2- Amino 3 cyano -4- oxo -5,5- dihydro-thiophene and 250ml phosphorus oxychloride (POCl3) in reaction flask, 38ml n,N-Dimethylformamide is slowly added dropwise at room temperature, is added dropwise within about 30 minutes.Room temperature reaction 1 hour, then it is warming up to 75 DEG C reaction 3 hours.It is cooled to room temperature, reaction solution is poured into trash ice, filter to obtain dark gray solid 89.1g, yield 86.9% melts 160-161 DEG C of point.
Embodiment 3: the preparation of intermediate 4- chloro-quinazoline
1) preparation of quinazoline -4 (3H) -one
It takes 13.7g (0.1mol) ortho-aminobenzoic acid and 20ml formamide in 250ml there-necked flask, is warming up to 140 DEG C instead It answers 5-8 hours.TLC is monitored after completion of the reaction, and reaction solution is cooled to 100 DEG C, is stirred lower dropwise addition 80ml water, is cooled to room later Temperature filters and obtains rufous 10.96g, yield 75.1% with filter cake is washed with anhydrous ether.
2) preparation of 4- chloro-quinazoline
Take 14.6g (0.1mol) (3H) -one of quinazoline -4 in 250ml single port bottle, 50ml thionyl chloride makees solvent, heating To back flow reaction 4-6 hours.TLC is monitored after completion of the reaction, is poured into water reaction solution after cooling and is stirred 30min, filtering is used in combination Anhydrous ether washs to obtain red brown solid 10.96g, yield 92.7%.
Embodiment 4: the synthesis of intermediate 3- (5- phenyl -1,4- Dimethyl-pyrazol -3- oxygroup) propylamin hydrochloride
1) preparation of N-Boc-2- bromine propylamine
21.6g (0.1mol) bromine ethamine bromate is placed in 80ml tetrahydrofuran, 10.08g (0.12mol) is sequentially added Sodium bicarbonate, 50ml water, are stirred at room temperature lower dropwise addition 21.80g (0.1mol) di-tert-butyl dicarbonate, and drop finishes, the reaction was continued 4-10 Hour.After completion of the reaction, the extraction of (3 × 50ml) ethyl acetate, organic phase saturated salt solution 50ml is added in evaporating solvent under reduced pressure It washs, colourless oil liquid 22.7g, yield 95.7% is obtained after precipitation.
2) preparation of N-Boc-3- (5- phenyl -1,4- Dimethyl-pyrazol -3- oxygroup) propylamine
By 2.38g (0.01mol) N-Boc-3- bromine propylamine and 1.88g (0.01mol) 5- phenyl -1,4- dimethyl -3- hydroxyl Base pyrazoles (preparation method refers to CN102584705) is added in 50ml butanone, 2.76g (0.02mol) potassium carbonate is added, under stirring It is heated to flowing back, react 4-10 hours, TLC is monitored after completion of the reaction, and (3 × 50ml) ethyl acetate is added in evaporating solvent under reduced pressure Extraction, organic phase wash with saturated salt solution 50ml, residue column chromatography after precipitation (eluant, eluent is ethyl acetate and petroleum ether, Volume ratio is 1:6) obtain yellow solid 2.94g, yield 85.2%.
3) preparation of 3- (5- phenyl -1,4- Dimethyl-pyrazol -3- oxygroup) propylamin hydrochloride
50ml second is added in 3.45g (0.01mol) N-Boc-3- (5- phenyl -1,4- Dimethyl-pyrazol -3- oxygroup) propylamine In acetoacetic ester, lower dropwise addition 6ml concentrated hydrochloric acid is stirred at room temperature, solid dissolution continues stirring 4-5 hours, and TLC is monitored after completion of the reaction, Evaporating solvent under reduced pressure is added 10ml methylene chloride and stirs half an hour, and evaporating solvent under reduced pressure obtains 2.68g yellow oil.
Embodiment 5: the synthesis of intermediate 3- (5- (2,4 dichloro benzene base) -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride
1) preparation of N-Boc-2- (5- (2,4 dichloro benzene base) -1- methyl pyrazole -3- oxygroup) ethamine
By 2.24g (0.01mol) N-Boc-2- bromine ethamine (1 in preparation method reference implementation example 4) step) and 2.43g 50ml is added in (0.01mol) 5- (2,4 dichloro benzene base) -1- methyl -3- hydroxypyrazoles (preparation method refers to CN102584705) In butanone, 2.76g (0.02mol) potassium carbonate is added, is heated to flowing back under stirring, react 4-10 hours, TLC monitors end of reaction Afterwards, the extraction of (3 × 50ml) ethyl acetate is added in evaporating solvent under reduced pressure, and organic phase is washed with saturated salt solution 50ml, after precipitation Residue column chromatography (eluant, eluent is ethyl acetate and petroleum ether, volume ratio 1:6) obtains yellow solid 3.12g, yield 80.8%.
2) preparation of 3- (5- (2,4 dichloro benzene base) -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride
3.86g (0.01mol) N-Boc-2- (5- (2,4 dichloro benzene base) -1- methyl pyrazole -3- oxygroup) ethamine is added In 50ml ethyl acetate, lower dropwise addition 6ml concentrated hydrochloric acid is stirred at room temperature, solid dissolution continues stirring 4-5 hours, TLC monitoring reaction After, evaporating solvent under reduced pressure is added 10ml methylene chloride and stirs half an hour, filtering, and washs filter cake with methylene chloride and obtain 3.05g light yellow solid.
Embodiment 6: the synthesis of intermediate 3- (5- (2,4 dichloro benzene base) -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride
1) preparation of N-Boc-2- (5- (4- methoxyphenyl) -1,4- Dimethyl-pyrazol -3- oxygroup) ethamine
By 2.24g (0.01mol) N-Boc-2- bromine ethamine and 2.18g (0.01mol) 5- (4- methoxyphenyl) -1,4- two Methyl -3- hydroxypyrazoles (preparation method refers to CN102584705) are added in 50ml butanone, and 2.76g (0.02mol) carbon is added Sour potassium is heated to flowing back under stirring, reacts 4-10 hours, and TLC is monitored after completion of the reaction, evaporating solvent under reduced pressure, be added (3 × 50ml) ethyl acetate extracts, and organic phase is washed with saturated salt solution 50ml, and (eluant, eluent is acetic acid to residue column chromatography after precipitation Ethyl ester and petroleum ether, volume ratio 1:6) obtain yellow solid 2.96g, yield 82.0%.
2) preparation of 3- (5- (2,4 dichloro benzene base) -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride
By 3.61g (0.01mol) N-Boc-2- (5- (4- methoxyphenyl) -1,4- Dimethyl-pyrazol -3- oxygroup) ethamine It is added in 50ml ethyl acetate, lower dropwise addition 6ml concentrated hydrochloric acid is stirred at room temperature, solid dissolution continues stirring 4-5 hours, TLC monitoring After completion of the reaction, evaporating solvent under reduced pressure is added 10ml methylene chloride and stirs half an hour, and evaporating solvent under reduced pressure obtains 2.33g yellow oil Shape object.
Embodiment 7: the synthesis of intermediate 3- (5- (4- bromophenyl) -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride
1) preparation of N-Boc-2- (5- (4- bromophenyl) -1- methyl pyrazole -3- oxygroup) ethamine
By 2.24g (0.01mol) N-Boc-2- bromine ethamine and 2.53g (0.01mol) 5- (4- bromophenyl) -1- methyl -3- Hydroxypyrazoles (preparation method refers to CN102584705) are added in 50ml butanone, and 2.76g (0.02mol) potassium carbonate, stirring is added Under be heated to flowing back, react 4-10 hour, TLC monitor after completion of the reaction, evaporating solvent under reduced pressure, addition (3 × 50ml) acetic acid second Ester extraction, organic phase are washed with saturated salt solution 50ml, and (eluant, eluent is ethyl acetate and petroleum to residue column chromatography after precipitation Ether, volume ratio 1:6) obtain red brown solid 3.15g, yield 79.5%.
2) preparation of 3- (5- (4- bromophenyl) -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride
50ml is added in 3.96g (0.01mol) N-Boc-2- (5- (4- bromophenyl) -1- methyl pyrazole -3- oxygroup) ethamine In ethyl acetate, lower dropwise addition 6ml concentrated hydrochloric acid is stirred at room temperature, solid dissolution continues stirring 4-5 hours, and TLC monitors end of reaction Afterwards, evaporating solvent under reduced pressure is added 10ml methylene chloride and stirs half an hour, filtering, and washs filter cake with methylene chloride and obtain 3.05g powder Red solid.
Embodiment 8: the synthesis of intermediate 1- methyl -2- (5- phenyl -1,4- dimethyl -3- oxygroup) ethamine
1) preparation of 1- (5- phenyl -1,4- Dimethyl-pyrazol -3- oxygroup) acetone
By 0.93g (0.01mol) chlroacetone and 1.88g (0.01mol) 5- phenyl -1,4- dimethyl -3- hydroxypyrazoles (system Preparation Method refers to CN102584705) it is added in 50ml DMF, 2.76g (0.02mol) potassium carbonate is added, is heated to back under stirring Stream reacts 4-10 hours, and TLC is monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, organic Mutually wash with saturated salt solution 50ml, after precipitation residue column chromatograph (eluant, eluent be ethyl acetate and petroleum ether, volume ratio 1: 5) red brown solid 3.15g, yield 79.5% are obtained.
2) preparation of 1- methyl -2- (5- phenyl -1,4- dimethyl -3- oxygroup) ethamine
By 2.44g (0.01mol) 1- (5- phenyl -1,4- Dimethyl-pyrazol -3- oxygroup) acetone and 11.5g (0.15mol) Ammonium acetate is added in 50ml methanol, and 1.26g (0.02mol) sodium cyanoborohydride is added portionwise, and 1ml glacial acetic acid is added dropwise after adding, It is stirred to react under ice valley 4-10 hours, TLC is monitored after completion of the reaction, and sodium hydrate aqueous solution is added dropwise into reaction solution to pH=8- 9, the extraction of (3 × 50ml) ethyl acetate is added, organic phase is washed with saturated salt solution 50ml, and yellow oil is obtained after precipitation 1.96g。
Embodiment 9: the preparation of compound 12-3-1
By the chloro- 6- difluoromethyl pyrimidin of 1.99g (0.01mol) 4,5- bis- and 2.82g (0.01mol) 3- (5- phenyl -1,4- Dimethyl-pyrazol -3- oxygroup) propylamin hydrochloride be added 50ml toluene in.4.45g (0.022mol) triethylamine is added, is heated to Reflux is reacted 4-10 hours, and TLC is monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, has Machine is mutually washed with saturated salt solution 50ml, and (eluant, eluent is ethyl acetate and petroleum ether (boiling range 60- to residue column chromatography after precipitation 90 DEG C), volume ratio 1:2) obtain yellow oil 1.95g, yield 47.9%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.54(s,1H,Pyrimidine-H),7.48 (t, J=6Hz, 2H, Ph-3,5-2H), 7.42 (t, J=6Hz, 1H, Ph-4-H), 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 6.75(s,1H,NH),6.73(t,JHF=54Hz, 1H, CHF2), 4.41 (t, J=6Hz, 2H, O-CH2),3.77-3.80(q, J =6Hz, 2H, N-CH2),3.63(s,3H,N-CH3),2.10-2.14(m,2H,CH2),1.89(s,3H, Pyrazole-4- CH3).
Embodiment 10: the preparation of compound 19-21
By 1.65g (0.01mol) 4- chloro-quinazoline and 3.22g (0.01mol) 3- (5- (2,4 dichloro benzene base) -1- methyl - Pyrazoles -3- oxygroup) ethylamine hydrochloride be added 50ml toluene in.4.45g (0.022mol) triethylamine is added, is heated to flowing back, instead It answers 4-10 hours, TLC is monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, and organic phase is used Saturated salt solution 50ml washing, residue column chromatography after precipitation (eluant, eluent is ethyl acetate and petroleum ether (60-90 DEG C of boiling range), Volume ratio is 1:2) obtain brown oil 2.85g, yield 68.8%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.70(s,1H,Quinazoline-3-H), 7.88 (d, J=6Hz, 1H, Quinazoline-5-H), 7.77 (t, J=6Hz, 1H, Quinazoline-6-H), 7.74 (d, J =6 Hz, 1H, Quinazoline-8-H), 7.70 (d, J=12Hz, 1H, Ph-6-H), 7.49 (t, J=6Hz, 1H, ), Quinazoline-7-H 7.41 (s, 1H, Ph-3-H), 7.25 (d, J=12Hz, 1H, Ph-5-H), 6.19 (s, 1H, NH), 6.10 (s, 1H, Pyrazole-4-H), 4.42 (t, J=6Hz, 2H, O-CH2), 4.13-4.16 (q, J=6Hz, 2H, N-CH2), 3.72(s, 3H,N-CH3).
Embodiment 11: the preparation of compound 21-1-72
By 2.05g (0.01mol) 4,5- dichloro-thiophene simultaneously [2,3-d] pyrimidine and 2.98g (0.01mol) 3- (5- (2,4- bis- Chlorphenyl) -1- methyl pyrazole -3- oxygroup) ethylamine hydrochloride be added 50ml toluene in.4.45g (0.022mol) three second is added Amine is heated to flowing back, and reacts 4-10 hours, and TLC is monitored after completion of the reaction, and (3 × 50ml) acetic acid is added in evaporating solvent under reduced pressure Ethyl ester extraction, organic phase are washed with saturated salt solution 50ml, and (eluant, eluent is ethyl acetate and petroleum to residue column chromatography after precipitation Ether (60-90 DEG C of boiling range), volume ratio 1:2) yellow solid 2.24g, 121.7 DEG C of fusing point, yield 52.2%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.47(s,1H,Pyrimidine-H),7.22 (d, J=6Hz, 2H, Ph-2,6-2H), 7.07 (s, 1H, NH), 7.06 (s, 1H, Thiophene-H), 6.99 (d, J=6Hz, 2H, Ph-3,5-2H), 4.50 (t, J=6Hz, 2H, O-CH2), 4.05-4.07 (q, J=6Hz, 2H, N-CH2),3.86(s,3H, N-CH3),3.58(s,3H,OCH3),1.86(s,3H,Pyrazole-4-CH3).
Embodiment 12: the preparation of compound 19-34
By 1.65g (0.01mol) 4- chloro-quinazoline and 3.33g (0.01mol) 3- (5- (4- bromophenyl) -1- methyl-pyrrole Azoles -3- oxygroup) ethylamine hydrochloride be added 50ml toluene in.4.45g (0.022mol) triethylamine is added, is heated to flowing back, reacts 4-10 hours, TLC was monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, and organic phase is used full It is washed with saline solution 50ml, (eluant, eluent is ethyl acetate and petroleum ether (60-90 DEG C of boiling range), body to residue column chromatography after precipitation Product is than being 1:2) obtain white solid 2.09g, yield 49.4%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.66(s,1H,Quinazoline-3-H), 7.84 (d, J=6Hz, 2H, Quinazoline-5,8-2H), 7.73 (t, J=6Hz, 2H, Quinazoline-6,7-2H), 7.45 (d, J=6Hz, 2H, Ph-2,6-2H), 7.39 (d, J=6Hz, 2H, Ph-3,5-2H), 7.05 (s, 1H, NH), 5.87 (s, 1H, Pyrazole-4-H), 4.51 (t, J=6Hz, 2H, O-CH2),4.04-4.09(q,2H,N-CH2),3.77(s,3H, N-CH3).
Embodiment 13: the preparation of compound 11-4-1
By the chloro- 6- ethyl-pyrimidine of 1.77g (0.01mol) 4,5- bis- and 2.45g (0.01mol) 1- methyl -2- (5- phenyl - 1,4- dimethyl -3- oxygroup) ethamine be added 50ml toluene in.4.45g (0.022mol) triethylamine is added, is heated to flowing back, instead It answers 4-10 hours, TLC is monitored after completion of the reaction, evaporating solvent under reduced pressure, and the extraction of (3 × 50ml) ethyl acetate is added, and organic phase is used Saturated salt solution 50ml washing, residue column chromatography after precipitation (eluant, eluent is ethyl acetate and petroleum ether (60-90 DEG C of boiling range), Volume ratio is 1:2) obtain yellow oil 1.05g, yield 28.8%.
1H-NMR (600MHz, internal standard TMS, solvent C DCl3)δ(ppm):8.42(s,1H,Pyrimidine-H),7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.30 (d, J=6Hz, 2H, Ph-2,6-2H), 6.22 (s, 1H, NH), 4.59-4.62 (m, 1H, N-CH), 4.35 (d, J=6Hz, 2H, O-CH2),3.61(s,3H,N-CH3), 2.76-2.80 (q, J=6Hz, 2H, CH2CH3),1.86(s,3H,Pyrazole-4-CH3),1.41(s,3H,CHCH3),1.26 (t, J=6Hz, 3H, CH2CH3).
Other compounds of the invention are referred to above embodiments preparation.
Part of compounds physical data and nuclear magnetic data (1HNMR, 600MHz, internal standard TMS, ppm) as follows:
Compound 10-1: 118.2 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.72(m,2H, Ph-2,6-2H),7.37(m,2H,Ph-3,5-2H),7.29(m,1H,Ph-4-H),5.85(s,1H,Pyrazole-H),5.75 (s, 1H, NH), 4.30 (t, J=6Hz, 2H, O-CH2),3.98(m,2H,NH-CH2),3.71(s,3H,N-CH3).
Compound 10-21: 110.8 DEG C of fusing point.δ(CDCl3): 8.40 (s, 1H, Pyrimidine-H), 7.72 (d, J= 6Hz, 1H, Ph-6-H), 7.43 (s, 1H, Ph-3-H), 7.25 (dd, J=6Hz, 1H, Ph-5-H), 6.09 (s, Pyrazole- 4-H), 5.72 (s, 1H, NH), 4.30 (t, J=6Hz, 2H, O-CH2), 3.96-3.99 (q, J=6Hz, 2H, N-CH3),3.72 (s,3H, N-CH3),2.48(s,3H,CH3).
Compound 10-34: 112.9 DEG C of fusing point.δ(CDCl3): 8.41 (s, 1H, Pyrimidine-H), 7.59 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.49 (d, J=6Hz, 2H, Ph-3,5-2H), 5.82 (s, 1H, Pyrazole-H), 5.71 (s, 1H, NH), 4.29 (t, J=6Hz, 2H, O-CH2),3.98(m,2H),3.70(s,3H,NH-CH2),2.48(s,3H, Pyrimidine-CH3).
Compound 10-69: 145.3 DEG C of fusing point.δ(CDCl3): 8.41 (s, 1H, Pyrimidine-H), 7.82 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.62 (d, J=6Hz, 2H, Ph-3,5-2H), 5.89 (s, 1H, Pyrazole-4-H), 5.72 (s, 1H, NH), 4.31 (t, J=6Hz, 2H, O-CH2), 3.97-4.00 (q, J=6Hz, 2H, N-CH2),3.72(s,3H,N- CH3),2.48(s, 3H,Pyrimidine-CH3)。
Compound 10-1-19: 109.4 DEG C of fusing point.δ(CDCl3): 8.38 (s, 1H, Pyrimidine-H), 7.45 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.25 (d, J=6Hz, 2H, Ph-3,5-2H), 6.42 (s, 1H, NH), 4.47 (t, J=6Hz, 2H, O-CH2),3.91(m,2H,NH-CH2),3.61(s,3H,N-CH3),2.46(s,3H,Pyrimidine-CH3),1.86 (s, 3H,Pyrazole-4-CH3).
Compound 10-1-57: 154.6 DEG C of fusing point.δ(CDCl3): 8.38 (s, 1H, Pyrimidine-H), 7.28 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.19 (d, J=6Hz, 2H, Ph-3,5-2H), 6.48 (s, 1H, NH), 4.47 (t, J=6Hz, 2H, O-CH2),3.91(m,2H,NH-CH2),3.61(s,3H,N-CH3),2.46(s,3H,Pyrimidine-CH3),2.42 (s, 3H,Ph-4-CH3),2.42(s,3H,Pyrazole-CH3).
Compound 10-1-72: 110.6 DEG C of fusing point.δ(CDCl3): 8.37 (s, 1H, Pyrimidine-H), 7.23 (d, J= 6Hz, 2H, Ph-2,6-2H), 6.99 (d, J=6Hz, 2H, Ph-3,5-2H), 6.47 (s, 1H, NH), 4.47 (t, J=6Hz, 2H, O-CH2), 3.89-3.92 (q, J=6Hz, 2H, N-CH2),3.86(s,3H,N-CH3),3.60(s,3H,OCH3),2.46 (s, 3H,Pyrimidine-CH3),1.86(s,3H,Pyrazole-4-CH3).
Compound 10-3-1: grease.δ(CDCl3): 8.37 (s, 1H, Pyrimidine-H), 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 6.23 (s, 1H, NH), 4.39 (t, J=6Hz, 2H, O-CH2), 3.71-3.74 (q, J=6Hz, 2H, N-CH2),3.63(s,3H,N-CH3), 2.45(s, 3H,CH3),2.10-2.14(m,2H,CH2),1.89(s,3H,Pyrazole-4-CH3).
Compound 10-4-1: grease.δ(CDCl3): 8.37 (s, 1H, Pyrimidine-H), 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.30 (d, J=6Hz, 2H, Ph-2,6-2H), 6.22 (s, 1H, NH), 4.58-4.63 (m, 1H, N-CH), 4.35 (d, J=6Hz, 2H, O-CH2),3.61(s,3H,N-CH3),2.45(s, 3H, CH3),1.86(s,3H,Pyrazole-4-CH3), 1.41 (d, J=6Hz, 3H, CHCH3).
Compound 11-1: 128.4 DEG C of fusing point.δ(CDCl3):8.41(s,1H,Pyrimidine-H),7.29-7.45(m, 5H, Ph-5H),6.21(s,1H,NH),5.74(s,1H,Pyrazole-H),4.40(t,2H,O-CH2),3.90(m,2H,N- CH2), 3.72(s,3H,N-CH3),2.79(m,2H,CH2),1.27(t,3H,CH3)。
Compound 11-21: 135.9 DEG C of fusing point.δ(CDCl3): 8.45 (s, 1H, Pyrimidine-H), 7.72 (d, J= 6Hz, 1H, Ph-6-H), 7.43 (s, 1H, Ph-3-H), 7.25 (dd, J=6Hz, 1H, Ph-5-H), 6.09 (s, Pyrazole- 4-H), 5.73 (s, 1H, NH), 4.31 (t, J=6Hz, 2H, O-CH2), 3.96-3.99 (q, J=6Hz, 2H, N-CH2),3.72 (s,3H, N-CH3), 2.79-2.83 (m, J=6Hz, 2H, CH2CH3), 1.27 (t, J=6Hz, 3H, CH2CH3).
Compound 11-34: grease.δ(CDCl3):8.42(s,1H,Pyrimidine-H),7.58(m,2H,Ph-2,6- 2H), 7.26(t,2H,Ph-3,5-2H),6.16(s,1H,NH),5.73(s,1H,Pyrazole-H),4.39(t,2H,O- CH2),3.89 (m,2H,N-CH2),3.70(s,3H,N-CH3),2.80(m,2H,CH2),1.28(t,3H,CH3)。
Compound 11-69: 124.8 DEG C of fusing point.δ(CDCl3): 8.46 (s, 1H, Pyrimidine-H), 7.82 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.62 (d, J=6Hz, 2H, Ph-3,5-2H), 5.89 (s, 1H, Pyrazole-4-H), 5.73 (s, 1H, NH), 4.32 (t, J=6Hz, 2H, O-CH2), 3.97-4.00 (q, J=6Hz, 2H, N-CH2),3.72(s,3H,N- CH3), 2.79-2.83 (q, J=6Hz, 2H, CH2CH3), 1.27 (t, J=6Hz, 3H, CH2CH3).
Compound 11-1-1: 92.9 DEG C of fusing point.δ(CDCl3):8.42(s,1H,Pyrimidine-H),7.45-7.47(d, 2H, Ph-2,6-2H),7.43(t,1H,Ph-4-H),7.32(t,2H,Ph-3,5-2H),6.43(s,1H,NH),4.47(t, 2H, O-CH2),3.89-3.94(m,2H,N-CH2),3.62(s,3H,N-CH3),2.75-2.83(m,2H,CH2),1.88(s, 3H, Pyrazole-4-CH3),1.26(t,3H,CH3)。
Compound 11-1-4: grease.δ(CDCl3):8.43(s,1H,Pyrimidine-H),7.25-7.29(m,2H, Ph-2,6-2H),7.15-7.18(t,2H,Ph-3,5-2H),6.41(s,1H,NH),4.47(t,2H,O-CH2),3.91(m, 2H, N-CH2),3.60(s,3H,N-CH3),2.80(m,2H,CH2),1.85(s,3H,Pyrazole-4-CH3),1.26(t, 3H, CH3)。
Compound 11-1-19: 113.5 DEG C of fusing point.δ(CDCl3):8.43(s,1H,Pyrimidine-H),7.45(m,2H, Ph-2,6-2H),7.24(t,2H,Ph-3,5-2H),6.38(s,1H,NH),4.46(t,2H,O-CH2),3.91(m,2H, N- CH2),3.61(s,3H,N-CH3),2.79(m,2H,CH2),1.86(s,3H,Pyrazole-4-CH3),1.25(t,3H, CH3)。
Compound 11-1-57: 134.0 DEG C of fusing point.δ(CDCl3):8.43(s,1H,Pyrimidine-H),7.27(m,2H, Ph-2,6-2H),7.20(t,2H,Ph-3,5-2H),6.46(s,1H,NH),4.47(t,2H,O-CH2),3.91(m,2H, N- CH2),3.61(s,3H,N-CH3),2.81(m,2H,CH2),2.42(s,3H,Ph-CH3),1.87(s,3H, Pyrazole-4- CH3),1.28(t,3H,CH3)。
Compound 11-1-72: grease.δ(CDCl3): 8.42 (s, 1H, Pyrimidine-H), 7.23 (d, J=6Hz, 2H, Ph-2,6-2H), 6.99 (d, J=6Hz, 2H, Ph-3,5-2H), 6.47 (s, 1H, NH), 4.47 (t, J=6Hz, 2H, O- CH2), 3.90-3.92 (q, J=6Hz, 2H, N-CH2),3.86(s,3H,N-CH3),3.61(s,3H,OCH3),2.77-2.81 (q, J=6Hz, 2H, CH2CH3),1.86(s,3H,Pyrazole-4-CH3), 1.26 (t, J=6Hz, 3H, CH2CH3).
Compound 11-3-1: grease.δ(CDCl3): 8.42 (s, 1H, Pyrimidine-H), 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 6.23 (s, 1H, NH), 4.39 (t, J=6Hz, 2H, O-CH2), 3.71-3.74 (q, J=6Hz, 2H, N-CH2),3.63(s,3H,N-CH3), 2.77-2.80 (q, J=6Hz, 2H, CH2CH3),2.10-2.14(m,2H,CH2),1.90(s,3H,Pyrazole-4-CH3), 1.26 (t, J=6Hz, 3H, CH2CH3).
Compound 12-1: 91.6 DEG C of fusing point.δ(CDCl3):8.59(s,1H,Pyrimidine-H),7.67-7.74(m, 2H, Ph-2,6-2H), 7.33-7.42 (m, 2H, Ph-3,5-2H), 7.25-7.31 (m, 1H, Ph-4-H), 6.73 (t, J= 54Hz,1H, CHF2), 6.06 (s, 1H, NH), 5.85 (s, 1H, Pyrazole-H), 4.31 (t, J=6Hz, 2H, O-CH2), 4.03(m,2H, NH-CH2),3.70(s,3H,N-CH3).
Compound 12-21: 105.4 DEG C of fusing point.δ(CDCl3): 8.59 (s, 1H, Pyrimidine-H), 7.72 (d, J= 6Hz, 1H, Ph-6-H), 7.43 (s, 1H, Ph-3-H), 7.26 (dd, J=6Hz, 1H, Ph-5-H), 6.73 (t, JHF=54Hz, 1H,CHF2), 6.10 (s, Pyrazole-4-H), 6.00 (s, 1H, NH), 4.33 (t, J=6Hz, 2H, O-CH2),4.02-4.05 (q, J=6Hz, 2H, N-CH2),3.72(s,3H,N-CH3).
Compound 12-34: 107.0 DEG C of fusing point.δ(CDCl3): 8.55 (s, 1H, Pyrimidine-H), 7.44 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.39 (d, J=6Hz, 2H, Ph-3,5-2H), 6.73 (t, JHF=54Hz, 1H, CHF2),6.70 (s, 1H, NH), 5.74 (s, 1H, Pyrazole-4-H), 4.44 (t, J=6Hz, 2H, O-CH2), 3.94-3.97 (q, J= 6Hz,2H,N-CH2), 3.73(s,3H,N-CH3).
Compound 12-69: 127.1 DEG C of fusing point.δ(CDCl3): 8.59 (s, 1H, Pyrimidine-H), 7.82 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.62 (d, J=6Hz, 2H, Ph-3,5-2H), 6.73 (t, JHF=54Hz, 1H, CHF2),6.01 (s, 1H, NH), 5.89 (s, 1H, Pyrazole-4-H), 4.33 (t, J=6Hz, 2H, O-CH2), 4.03-4.06 (q, J= 6Hz,2H, N-CH2),3.72(s,3H,N-CH3).
12-1-1: δ (CDCl of compound3):8.55(s,1H,Pyrimidine-H),7.45-7.48(d,2H,Ph-2,6- 2H), 7.44(t,1H,Ph-4-H),7.30(t,2H,Ph-3,5-2H),7.02(s,1H,NH),6.73(s,1H,CH),4.51 (t,2H, O-CH2),3.92-3.97(m,2H,N-CH2),3.62(s,3H,N-CH3),1.87(s,3H,Pyrazole-4- CH3)。
Compound 12-1-4: 88.8 DEG C of fusing point.δ(CDCl3):8.55(s,1H,Pyrimidine-H),7.28(m,2H, ), Ph-2,6-2H 7.14 (m, 2H, Ph-3,5-2H), 7.01 (s, 1H, NH), 6.75 (s, J=54Hz, 1H, CHF2),4.50(t, J=6Hz, 2H, O-CH2),3.95(m,2H,NH-CH2),3.60(s,3H,N-CH3),1.84(s,3H, Pyrazole-4- CH3).
Compound 12-1-19: 100.6 DEG C of fusing point.δ(CDCl3): 8.56 (s, 1H, Pyrimidine-H), 7.48 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.25 (d, J=6Hz, 2H, Ph-3,5-2H), 6.96 (s, 1H, NH), 6.73 (t, J=54Hz, 1H, CHF2), 4.49 (t, J=6Hz, 2H, O-CH2),3.95(m,2H,NH-CH2),3.61(s,3H,N-CH3),1.86(s, 3H, Pyrazole-4-CH3).
Compound 12-1-57: grease.δ(CDCl3): 8.55 (s, 1H, Pyrimidine-H), 7.27 (d, J=6Hz, 2H, Ph-2,6-2H), 7.19 (d, J=6Hz, 2H, Ph-3,5-2H), 7.06 (s, 1H, NH), 6.73 (t, JHF=54Hz, 1H, ), CH 4.51 (t, J=6Hz, 2H, O-CH2), 3.93-3.95 (q, J=6Hz, 2H, N-CH2),3.61(s,3H,N-CH3), 2.42(s, 3H,Ph-4-CH3),1.86(s,3H,Pyrazole-4-CH3).
Compound 12-1-72: grease.δ(CDCl3): 8.55 (s, 1H, Pyrimidine-H), 7.22 (d, J=6Hz, 2H, Ph-2,6-2H), 7.06 (s, 1H, NH), 6.99 (d, J=6Hz, 2H, Ph-3,5-2H), 6.73 (t, JHF=54Hz, 1H, CHF2), 4.50 (t, J=6Hz, 2H, O-CH2), 3.93-3.95 (q, J=6Hz, 2H, N-CH2),3.86(s,3H,N-CH3), 3.60(s, 3H,OCH3),1.86(s,3H,Pyrazole-4-CH3).
Compound 12-3-1: yellow oil.δ(CDCl3): 8.54 (s, 1H, Pyrimidine-H), 7.48 (t, J= 6Hz, 2H, Ph-3,5-2H), 7.42 (t, J=6Hz, 1H, Ph-4-H), 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 6.75 (s,1H,NH), 6.73(t,JHF=54Hz, 1H, CHF2), 4.41 (t, J=6Hz, 2H, O-CH2), 3.77-3.80 (q, J= 6Hz,2H, N-CH2),3.63(s,3H,N-CH3),2.10-2.14(m,2H,CH2),1.89(s,3H,Pyrazole-4-CH3).
Compound 12-4-1: grease.δ(CDCl3): 8.46 (s, 1H, Pyrimidine-H), 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 7.04 (s, 1H, Thiophene-H), 6.89 (s, 1H, NH), 4.40 (t, J=6Hz, 2H, O-CH2), 3.85-3.88 (q, J=6Hz, 2H, N-CH2),3.61(s,3H,N-CH3),2.19-2.23(m,2H,CH2),1.87(s,3H,Pyrazole-4-CH3).
Compound 19-69: 175.9 DEG C of fusing point.δ(CDCl3):8.71(s,1H,Quinazoline-3-H),7.89(d,J =6Hz, 1H, Quinazoline-5-H), 7.79 (d, J=6Hz, 2H, Ph-2,6-2H), 7.77 (t, J=6Hz, 1H, ), Quinazoline-6-H 7.72 (d, J=6Hz, 1H, Quinazoline-8-H), 7.61 (d, J=6Hz, 2H, Ph-3,5- 2H), 7.50 (t, J=6Hz, 1H, Quinazoline-7-H), 6.07 (s, 1H, NH), 5.91 (s, 1H, Pyrazole-4-H), 4.43 (t, J=6Hz, 2H, O-CH2), 4.15-4.18 (q, J=6Hz, 2H, N-CH2),3.73(s,3H,N-CH3).
Compound 19-1-72: grease.δ(CDCl3): 8.67 (s, 1H, Quinazoline-3-H), 7.88 (d, J= 12Hz, 1H, Quinazoline-5-H), 7.85 (d, J=6Hz, 1H, Quinazoline-8-H), 7.73 (m, 1H, ), Quinazoline-6-H 7.63 (s, 1H, NH), 7.44 (d, J=6Hz, 1H, Quinazoline-7-H), 7.23 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.01 (d, J=6Hz, 2H, Ph-3,5-2H), 4.60 (t, J=6Hz, 2H, O-CH2),4.03- 4.05 (q, J=6Hz, 2H, N-CH2),3.87(s,3H,N-CH3),3.69(s,3H,OCH3),1.87(s,3H,Pyrazole- 4-CH3).
Compound 19-3-1: 109.6 DEG C of fusing point.δ(CDCl3):8.66(s,1H,Quinazoline-3-H),7.88(d,J =6Hz, 1H, Quinazoline-5-H), 7.84 (d, J=6Hz, 1H, Quinazoline-8-H), 7.72 (t, J=6Hz, 1H, Quinazoline-6-H), 7.48 (t, J=6Hz, 2H, Ph-3,5-2H), 7.43 (m, 2H, Ph-4-H+ ), Quinazoline-7-H 7.32 (d, J=6Hz, 2H, Ph-2,6-2H), 7.12 (s, 1H, NH), 4.48 (t, J=6Hz, 2H, O-CH2),3.88-3.91(q, 2H,N-CH2),3.67(s,3H,N-CH3),2.19-2.23(m,2H,CH2),1.92(s,3H, Pyrazole-4-H).
Compound 19-4-1: grease.δ(CDCl3): 8.66 (s, 1H, Quinazoline-3-H), 7.84 (d, J= 6Hz, 1H, Quinazoline-5-H), 7.82 (d, J=6Hz, 1H, Quinazoline-8-H), 7.71 (t, J=6Hz, 1H, ), Quinazoline-6-H 7.47 (t, J=6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 2H, Ph-4-H, ), Quinazoline-7-H 7.40 (s, 1H, NH), 7.29 (d, J=6Hz, 2H, Ph-2,6-2H), 4.76-4.79 (m, 1H, N- ), CH 4.47 (d, J=6Hz, 2H, O-CH2),3.69(s,s,3H,N-CH3),1.87(s,3H,Pyrazole-4-CH3), 1.48 (d, J=6Hz, 3H, CHCH3).
Compound 21-1: 136.8 DEG C of fusing point.δ(CDCl3):8.50(s,1H,Pyrimidine-H),7.68-7.73(m, 2H, Ph-2,6-2H),7.37(m,2H,Ph-3,5-2H),7.26-7.30(m,1H,Ph-4-H),7.11(s,1H, ), Thiophene-H 6.91 (s, 1H, NH), 5.87 (s, 1H, Pyrazole-H), 4.37 (t, J=6Hz, 2H, O-CH2), 4.11(m,2H, NH-CH2),3.72(s,3H,N-CH3).
Compound 21-21: 123.8 DEG C of fusing point.δ(CDCl3): 8.49 (s, 1H, Pyrimidine-H), 7.72 (d, J= 6Hz, 1H, Ph-6-H), 7.43 (s, 1H, Ph-3-H), 7.26 (dd, J=6Hz, 1H, Ph-5-H), 7.11 (s, 1H, ), Thiophene-H 6.90 (s, 1H, NH), 6.11 (s, Pyrazole-4-H), 4.37 (t, J=6Hz, 2H, O-CH2), 4.09-4.12 (q, J=6Hz, 2H, N-CH2),3.72(s,3H,N-CH3).
Compound 21-34: grease.δ(CDCl3): 8.47 (s, 1H, Pyrimidine-H), 7.44 (d, J=6Hz, 2H, Ph-2,6-2H),7.39(d,2H,Ph-3,5-2H),7.07(s,1H,Thiophene-H),7.00(s,1H,NH),5.75(s, 1H, Pyrazole-4-H), 4.44 (t, J=6Hz, 2H, O-CH2), 4.03-4.08 (q, J=6Hz, 2H, N-CH2),3.72(s, 3H,N-CH3)。
Compound 21-69: 177.3 DEG C of fusing point.δ(CDCl3): 8.50 (s, 1H, Pyrimidine-H), 7.82 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.62 (d, J=6Hz, 2H, Ph-3,5-2H), 7.11 (s, 1H, Thiophene-H), 6.89 (s, 1H, NH), 5.91 (s, 1H, Pyrazole-4-H), 4.38 (t, J=6Hz, 2H, O-CH2), 4.10-4.13 (q, J=6Hz, 2H,N-CH2), 3.73(s,3H,N-CH3).
Compound 21-1-4: 148.2 DEG C of fusing point.δ(CDCl3):8.47(s,1H,Pyrimidine-H),7.30(m,2H, ), Ph-2,6-2H 7.16 (m, 2H, Ph-3,5-2H), 7.06 (s, 2H, Thiophene-H+NH), 4.50 (t, J=6Hz, 2H, O-CH2),4.06(m,2H,NH-CH2),3.58(s,3H,N-CH3),1.85(s,3H,Pyrazole-4-CH3).
Compound 21-1-19: 161.2 DEG C of fusing point.δ(CDCl3): 8.47 (s, 1H, Pyrimidine-H), 7.45 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.23 (d, J=6Hz, 2H, Ph-3,5-2H), 7.06 (s, 1H, Thiophene-H), 7.05 (s, 1H, NH), 4.50 (t, J=6Hz, 2H, O-CH2),4.06(m,2H,NH-CH2),3.58(s,3H,N-CH3),1.86(s,3H, Pyrazole-4-CH3).
Compound 21-1-57: 149.3 DEG C of fusing point.δ(CDCl3): 8.47 (s, 1H, Pyrimidine-H), 7.27 (d, J= 6Hz, 2H, Ph-2,6-2H), 7.19 (d, J=6Hz, 2H, Ph-3,5-2H), 7.07 (s, 1H, NH), 7.05 (s, 1H, ), Pyrazole-H 4.50 (t, J=6Hz, 2H, O-CH2),4.06(m,2H,NH-CH2),3.59(s,3H,N-CH3),2.41 (s,3H, Ph-CH3),1.87(s,3H,Pyrazole-CH3).
Compound 21-3-1: 109.0 DEG C of fusing point.δ(CDCl3): 8.54 (s, 1H, Pyrimidine-H), 7.47 (t, J= 6Hz, 2H, Ph-3,5-2H), 7.420 (t, J=6Hz, 1H, Ph-4-H), 7.31 (d, J=6Hz, 2H, Ph-2,6-2H), 6.85 (s,1H, NH),6.72(t,JHF=54Hz, 1H, CHF2), 4.63-4.65 (m, 1H, N-CH), 4.38 (d, J=6Hz, 2H, O- CH2), 3.61(s,3H,N-CH3),1.86(s,3H,Pyrazole-4-CH3), 1.41 (d, J=6Hz, 3H, CHCH3).
Compound 21-4-1: 149.3 DEG C of fusing point.δ(CDCl3): 8.46 (s, 1H, Pyrimidine-H), 7.46 (t, J= 6Hz, 2H, Ph-3,5-2H), 7.41 (t, J=6Hz, 1H, Ph-4-H), 7.29 (d, J=6Hz, 2H, Ph-2,6-2H), 7.04 (s, 1H, Thiophene-H), 6.91 (s, 1H, NH), 4.84-4.86 (m, 1H, N-CH), 4.39 (d, J=6Hz, 2H, O- CH2), 3.59(s,3H,N-CH3),1.87(s,3H,Pyrazole-4-CH3), 1.48 (d, J=6Hz, 3H, CHCH3).
Meanwhile corresponding raw material being replaced according to the content recorded in above-mentioned each synthetic example and can be obtained this hair Other compounds shown in bright general formula I.
In addition, above-mentioned acquisition compound is reacted with acid in a conventional manner, and then obtain corresponding salt.
Biological activity determination embodiment
Compound shown in above-mentioned acquisition general formula I of the present invention shows good activity to a variety of germs in agriculture field, It is specific:
The compound sample shown in general formula I of the present invention has carried out Antifungal Activity in Vitro or work to a variety of fungal diseases of plant The test of body protecting effect.Bactericidal activity measurement result is shown in following example.
(1) in vitro bactericidal activity measurement
Measuring method is as follows: using high-throughput screening method, i.e., the solvent being suitble to test compound sample use be (solvent Type such as acetone, methanol, DMF etc., and selected according to its solvability to sample) dissolution, it is configured to required concentration and waits for 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.It is investigated after 24 hours, when investigation estimates cause of disease Bacterium brood body sprouts or growing state, and according to the sprouting of control treatment or growing state, evaluates compound bacteriostatic activity.
Test result is as follows for the Antifungal Activity in Vitro (being indicated with inhibiting rate) of part of compounds:
To the inhibiting rate of Pyricularia oryzae:
Under 25ppm dosage,
Compound 10-1-72,10-3-1,11-1-1,11-1-72,11-3-1,12-1-1,12-3-1,12-1-57,12- 1-72,19-34,12-3-1,19-1-72,19-3-1,21-1-72,21-34 etc., to the inhibiting rate of rice blast 80% or more； Compound 10-1-72,10-3-1,11-1-72,12-1-72,12-3-1,19-3-1 are to the inhibiting rate of gray mold 80% or more； And comparison medicament CK1, CK2, CK3, CK4 and CK5 are 0 to the inhibiting rate of rice blast.
(2) living body protection activity measures
Measuring method is as follows: use living body potting measuring method, i.e., by test compound sample with a small amount of solvent (solvent Type such as acetone, methanol, DMF etc., and selected, the volume ratio of quantity of solvent and spouting liquid according to its solvability to sample Equal to or less than 0.05) dissolving, is diluted with the water containing 0.1% Tween 80, be configured to required concentration prepare liquid.It is spraying in crop On machine, prepare liquid is sprayed on disease host plant (host plant is the standard Potted orchard cultivated in greenhouse), 24 hours Disease inoculation is carried out afterwards.According to disease feature, phjytotron will be placed on after the disease plant inoculating for needing temperature control moisturizing culture Middle culture moves into hot-house culture, the disease plant for not needing moisturizing culture is directly inscribed in greenhouse after disease completion is infected It plants and cultivates.(usually week age) carries out the assessment of compound protection effect after the onset of compareing sufficiently.
Test result is as follows for the living body protection activity of part of compounds:
Under 400ppm dosage,
Compound 10-1,10-1-4,10-1-19,10-1-57,10-1-72,10-34,10-59,11-1-1,11-1-72, 11-59、12-1、12-1-1、12-1-4、12-1-19、12-1-57、12-1-72、12-34、12-59、19-1、19-1-4、 19- 1-19、19-1-57、19-1-72、19-34、19-59、21-1、21-1-4、21-1-19、21-1-57、21-1-72、 21-34、 21-59 etc., to cucumber downy mildew 80% or more；
Compound 10-1-72,10-3-1,11-1-72,11-3-1,12-1-57,12-1-72,12-3-1,12-34,19- 1-72,21-1-72,21-3-1 etc., to wheat powdery mildew preventive effect 80% or more；
Compound 10-1-72,10-3-1,11-1-1,11-1-72,11-3-1,12-1-1,12-1-57,12-1-72,12- 3-1,19-1-72,19-3-1,19-34,21-1-72,21-3-1 etc., to corn rust preventive effect 80% or more；
Compound has: 12-1-1 etc., to melon anthracnose preventive effect up to 100%.
Other compounds shown in general formula I of the present invention are surveyed accordingly according to the mode of above-mentioned biological activity determination Examination, also has corresponding activity.

Claims (10)

1. a kind of substituted uracil compound, it is characterised in that: substituted uracil compound is compound 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-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 R2Also five yuan, hexa-atomic, seven yuan or octatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy, halogenated C1-C12Alkoxy, C3-C12Naphthenic base, C1-C12Alkylthio group, C2-C12Enylsulfanyl, C2-C12Alkenyl, C2-C12Alkynyl, halogenated C2-C12It is alkenyl, halogenated C2-C12Alkynyl, C1-C12Alkoxy C1-C12Alkyl, halogenated C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12Alkyl, Halogenated C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkyl sulphinyl, halogenated C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphur Acyl group, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkyl amino sulfonyl, two (C1-C12Alkyl) amino-sulfonyl, C1-C12Alkane Base sulfonyl amino carbonyl, C1-C12Alkyl-carbonyl-amino sulfonyl, C3-C12Cycloalkyloxycarbonyl, C1-C12Alkyl-carbonyl, halogen For C1-C12Alkyl-carbonyl, C1-C12Alkoxy carbonyl, halogenated C1-C12Alkoxy carbonyl, C1-C12Alkyl-carbonyl C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkyl amino-carbonyl, two (C1-C12Alkyl) amino carbonyl, C2-C12Alkenyloxy group Carbonyl, C2-C12Alkynyloxycar bonyl, C1-C12Alkoxy C1-C12Alkoxy carbonyl, C1-C12Alkyl amino sulfenyl, two (C1-C12Alkane Base) amino sulfenyl, the unsubstituted or aryl carbonyl C that are replaced by the following groups of 1-51-C6Alkyl, aryl carbonyl, aryloxy group carbonyl Base, aryl C1-C6Alkyloxycarbonyl, aryl C1-C6Alkyl, Heteroarylcarbonyl C1-C6Alkyl, Heteroarylcarbonyl, heteroaryloxy Carbonyl, heteroaryl C1-C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyl, following group are halogen, nitro, cyano, C1-C6Alkane Base, halogenated C1-C6Alkyl, C1-C6Alkoxy or halogenated C1-C6Alkoxy；
R4、R5Identical or different is respectively selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy is halogenated C1-C12Alkoxy；
Wherein, R4、R5Coupled C can also form C3-C8Ring；
R6、R7Identical or different is respectively selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy is halogenated C1-C12Alkoxy；
Wherein, R6、R7Coupled C can also form C3-C8Ring；
M is selected from 0 to 5 integer；
R8Selected from hydrogen, cyano, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12Alkoxy carbonyl, halogenated C1-C12Alkoxy It is carbonyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl Base, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R9Selected from hydrogen, C1-C12Alkyl, C3-C8Naphthenic base, halogenated C1-C12Alkyl, C1-C12Alkyl-carbonyl, halogenated C1-C12Alkyl oxycarbonyl Base, C1-C12Alkyl sulphonyl, halogenated C1-C12Alkyl sulphonyl, C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl Carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C12Alkyl, halogenated C1-C12Alkyl, C1-C12It is alkoxy, halogenated C1-C12Alkoxy, C3-C12Naphthenic base, C1-C12Alkyl amino, halogenated C1-C12Alkyl amino, two (C1-C12Alkyl) amino, halogen Two (C of generation1-C12Alkyl) amino, C (=O) NR11R12、C1-C12Alkylthio group, halogenated C1-C12Alkylthio group, C2-C12Alkenyl, C2-C12 Alkynyl, C2-C12Alkenyloxy group, halogenated C2-C12Alkenyloxy group, C2-C12Alkynyloxy group, halogenated C2-C12Alkynyloxy group, C1-C12Alkyl sulphonyl, Halogenated C1-C12Alkyl sulphonyl, C1-C12Alkyl-carbonyl, halogenated C1-C12Alkyl-carbonyl, C1-C12Alkoxy carbonyl, halogenated C1-C12 Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl, halogenated C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12Alkane Base, halogenated C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, halogenated C1-C12Alkoxy carbonyl C1-C12 Alkyl, C1-C12Alkylthiocarbonyl C1-C12Alkyl, halogenated C1-C12Alkylthiocarbonyl C1-C12Alkyl, C1-C12Alkyl carbonyl epoxide, Halogenated C1-C12Alkyl carbonyl epoxide, C1-C12Alkoxy-carbonyl oxy, halogenated C1-C12Alkoxy-carbonyl oxy, C1-C12Alkyl sulphur Acyloxy, halogenated C1-C12Alkyl sulphonyl oxygroup, C1-C12Alkoxy C1-C12Alkoxy or halogenated C1-C12Alkoxy C1-C12 Alkoxy；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C12Alkyl, halogenated C1-C12Alkyl, C3-C8Naphthenic base, C1-C12Alkoxy, C1-C12Alkylthio group or C1-C12Alkyl sulphonyl；
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. substituted uracil compound according to claim 1, it is characterised in that: in the compound of Formula I:
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Naphthenic base, C1-C6 Alkoxy, halogenated C1-C6Alkoxy, C1-C6Alkylthio group, C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkane Sulfenyl, C2-C6Alkenyl, halogenated C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6Alkynyl, C3-C6Alkenyloxy group, halogenated C3-C6Alkenyloxy group, C3-C6Alkynyloxy group, halogenated C3-C6Alkynyloxy group, C1-C6Alkyl amino, two (C1-C6Alkyl) amino, C1-C6Alkyl amino-carbonyl, halogen For C1-C6Alkyl amino-carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkoxy C1-C6Alkyl or C1- C6Alkylthio group C1-C6Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy Or halogenated C1-C6Alkoxy；
R1And R2Also five yuan or hexatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy, halogenated C1-C6Alkoxy, C3- C6Naphthenic base, C1-C6Alkylthio group, C2-C6Enylsulfanyl, C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6Alkenyl, halogenated C2-C6Alkynes Base, C1-C6Alkoxy C1-C6Alkyl, halogenated C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group C1-C6Alkyl, halogenated C1-C6Alkane Sulfenyl C1-C6Alkyl, C1-C6Alkyl sulphinyl, halogenated C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halogenated C1-C6 Alkyl sulphonyl, C1-C6Alkyl amino sulfonyl, two (C1-C6Alkyl) amino-sulfonyl, C1-C6Alkylsulfonyl aminocarbonyl, C1-C6Alkyl-carbonyl-amino sulfonyl, C3-C6Cycloalkyloxycarbonyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl-carbonyl, C1- C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkyl-carbonyl C1-C6Alkyl, C1-C6Alkoxy carbonyl C1-C6Alkyl, C1-C6Alkyl amino-carbonyl, two (C1-C6Alkyl) amino carbonyl, C2-C6Allyloxycarbonyl, C2-C6Alkynyloxycar bonyl, C1-C6Alkane Oxygroup C1-C6Alkoxy carbonyl, C1-C6Alkyl amino sulfenyl, two (C1-C6Alkyl) amino sulfenyl, it is unsubstituted or by 1-5 such as The aryl carbonyl C that lower group replaces1-C6Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C6Alkyloxycarbonyl, aryl C1- C6Alkyl, Heteroarylcarbonyl C1-C6Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C6Alkyloxycarbonyl, heteroaryl Base C1-C6Alkyl, following group are 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-C6Naphthenic base, halogenated C1-C6Alkyl, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl-carbonyl, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkyl sulphonyl, C1-C6Alkoxy carbonyl, C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkane Epoxide carbonyl C1-C6It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, virtue Epoxide carbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy, halogenated C1-C6 Alkoxy, C3-C6Naphthenic base, C1-C6Alkyl amino, halogenated C1-C6Alkyl amino, two (C1-C6Alkyl) amino, halogenated two (C1- C6Alkyl) amino, C (=O) NR11R12、C1-C6Alkylthio group, halogenated C1-C6Alkylthio group, C2-C6Alkenyl, C2-C6Alkynyl, C2-C6Alkene Oxygroup, halogenated C2-C6Alkenyloxy group, C2-C6Alkynyloxy group, halogenated C2-C6Alkynyloxy group, C1-C6Alkyl sulphonyl, halogenated C1-C6Alkyl sulphur Acyl group, C1-C6Alkyl-carbonyl, halogenated C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl, halogenated C1-C6Alkoxy carbonyl, C1-C6Alkane Oxygroup C1-C6Alkyl, halogenated C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group C1-C6Alkyl, halogenated C1-C6Alkylthio group C1-C6Alkane Base, C1-C6Alkoxy carbonyl C1-C6Alkyl, halogenated C1-C6Alkoxy carbonyl C1-C6Alkyl, C1-C6Alkylthiocarbonyl C1-C6Alkane Base, halogenated C1-C6Alkylthiocarbonyl C1-C6Alkyl, C1-C6Alkyl carbonyl epoxide, halogenated C1-C6Alkyl carbonyl epoxide, C1-C6Alkane Epoxide carbonyl oxygroup, halogenated C1-C6Alkoxy-carbonyl oxy, C1-C6Alkyl sulphonyl oxygroup, halogenated C1-C6Alkyl sulphonyl oxygen Base, C1-C6Alkoxy C1-C6Alkoxy or halogenated C1-C6Alkoxy C1-C6Alkoxy；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C6Alkyl, halogenated C1-C6Alkyl, C3-C6Naphthenic base, C1-C6Alkoxy, C1-C6Alkylthio group or C1- C6Alkyl sulphonyl；
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. substituted uracil compound according to claim 2, it is characterised in that: in the general formula I Q be selected from it is unsubstituted or By 1-5 R10Substituted aryl, the structural formula of compound formula I are as shown in I-1；
In formula,
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4 Alkoxy, halogenated C1-C4Alkoxy, C1-C4Alkylthio group, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkane Sulfenyl, C2-C4Alkenyl, halogenated C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkynyl, C3-C4Alkenyloxy group, halogenated C3-C4Alkenyloxy group, C3-C4Alkynyloxy group, halogenated C3-C4Alkynyloxy group, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl amino-carbonyl, halogen For C1-C4Alkyl amino-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkyl or C1- C4Alkylthio group C1-C4Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy Or halogenated C1-C4Alkoxy；
R1And R2Also five yuan or hexatomic ring containing C, N, O or S can be formed with the pyrimidine ring being connected；
X is selected from NR3, O or S；
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alkoxy, C3- C4Naphthenic base, C1-C4Alkylthio group, C2-C4Enylsulfanyl, C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkenyl, halogenated C2-C4Alkynes Base, C1-C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkane Sulfenyl C1-C4Alkyl, C1-C4Alkyl sulphinyl, halogenated C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogenated C1-C4 Alkyl sulphonyl, C1-C4Alkyl amino sulfonyl, two (C1-C4Alkyl) amino-sulfonyl, C1-C4Alkylsulfonyl aminocarbonyl, C1-C4Alkyl-carbonyl-amino sulfonyl, C3-C4Cycloalkyloxycarbonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1- C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, C2-C4Allyloxycarbonyl, C2-C4Alkynyloxycar bonyl, C1-C4Alkane Oxygroup C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or by 1-5 such as The aryl carbonyl C that lower group replaces1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkyloxycarbonyl, aryl C1- C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C4Alkyloxycarbonyl, heteroaryl Base C1-C4Alkyl, following group are 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-C4Naphthenic base, halogenated C1-C4Alkyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkyl sulphonyl, C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkane Epoxide carbonyl C1-C4It is alkyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, virtue Epoxide carbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl；
R10Selected from halogen, hydroxyl, amino, cyano, nitro, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4 Alkoxy, C3-C4Naphthenic base, C1-C4Alkyl amino, halogenated C1-C4Alkyl amino, two (C1-C4Alkyl) amino, halogenated two (C1- C4Alkyl) amino, C (=O) NR12R13、C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C2-C4Alkenyl, C2-C4Alkynyl, C2-C4Alkene Oxygroup, halogenated C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halogenated C2-C4Alkynyloxy group, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkyl sulphur Acyl group, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkane Oxygroup C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkylthio group C1-C4Alkane Base, C1-C4Alkoxy carbonyl C1-C4Alkyl, halogenated C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkylthiocarbonyl C1-C4Alkane Base, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4Alkane Epoxide carbonyl oxygroup, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphonyl oxygen Base, C1-C4Alkoxy C1-C4Alkoxy or halogenated C1-C4Alkoxy C1-C4Alkoxy；
R11、R12Identical or different is respectively selected from hydrogen, C1-C12Alkyl or halogenated C1-C12Alkyl；
W is selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, C1-C4Alkylthio group or C1- C4Alkyl sulphonyl.
4. substituted uracil compound according to claim 3, it is characterised in that: compound shown in the general formula I-1 Structure are as follows: 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-C4Naphthenic base, C1-C4Alkyl amino, halogenated C1-C4Alkyl amino, two (C1-C4Alkyl) amino, halogenated two (C1- C4Alkyl) amino, C (=O) NR11R12、C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C2-C4Alkenyl, C2-C4Alkynyl, C2-C4Alkene Oxygroup, halogenated C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halogenated C2-C4Alkynyloxy group, C1-C4Alkyl sulphonyl, halogenated C1-C4Alkyl sulphur Acyl group, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkane Oxygroup C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkylthio group C1-C4Alkane Base, C1-C4Alkoxy carbonyl C1-C4Alkyl, halogenated C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkylthiocarbonyl C1-C4Alkane Base, halogenated C1-C4Alkylthiocarbonyl C1-C4Alkyl, C1-C4Alkyl carbonyl epoxide, halogenated C1-C4Alkyl carbonyl epoxide, C1-C4Alkane Epoxide carbonyl oxygroup, halogenated C1-C4Alkoxy-carbonyl oxy, C1-C4Alkyl sulphonyl oxygroup, halogenated C1-C4Alkyl sulphonyl oxygen Base, C1-C4Alkoxy C1-C4Alkoxy or halogenated C1-C4Alkoxy C1-C4Alkoxy；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It is identical or different；
R11、R12Identical or different is respectively selected from hydrogen, C1-C4Alkyl or halogenated C1-C4Alkyl；
W is selected from hydrogen, halogen, C1-C4Alkyl, halogenated C1-C4Alkyl, C3-C4Naphthenic base, C1-C4Alkoxy, C1-C4Alkylthio group or C1- C4Alkyl sulphonyl；
And when the compound is general formula I-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-C4Naphthenic base, C1-C4 Alkoxy, halogenated C1-C4Alkoxy, C1-C4Alkylthio group, halogenated C1-C4Alkylthio group, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphur Acyl group, C2-C4Alkenyl, halogenated C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkynyl, C3-C4Alkenyloxy group, halogenated C3-C4Alkenyloxy group, C3-C4Alkynyloxy group, halogenated C3-C4Alkynyloxy group, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl amino-carbonyl, halogen For C1-C4Alkyl amino-carbonyl, C1-C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkoxy C1-C4Alkyl or C1- C4Alkylthio group C1-C4Alkyl；
R2Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy Or halogenated C1-C4Alkoxy；
When the compound is general formula I-1A, I-1B and I-1C,
R3Selected from hydrogen, hydroxyl, formoxyl, C1-C4Alkyl, halogenated C1-C4Alkyl, C1-C4Alkoxy, halogenated C1-C4Alkoxy, C3- C4Naphthenic base, C1-C4Alkylthio group, C2-C4Enylsulfanyl, C2-C4Alkenyl, C2-C4Alkynyl, halogenated C2-C4Alkenyl, halogenated C2-C4Alkynes Base, C1-C4Alkoxy C1-C4Alkyl, halogenated C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halogenated C1-C4Alkane Sulfenyl C1-C4Alkyl, C1-C4Alkyl sulphinyl, halogenated C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halogenated C1-C4 Alkyl sulphonyl, C1-C4Alkyl amino sulfonyl, two (C1-C4Alkyl) amino-sulfonyl, C1-C4Alkylsulfonyl aminocarbonyl, C1-C4Alkyl-carbonyl-amino sulfonyl, C3-C4Cycloalkyloxycarbonyl, C1-C4Alkyl-carbonyl, halogenated C1-C4Alkyl-carbonyl, C1- C4Alkoxy carbonyl, halogenated C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, C2-C4Allyloxycarbonyl, C2-C4Alkynyloxycar bonyl, C1-C4Alkane Oxygroup C1-C4Alkoxy carbonyl, C1-C4Alkyl amino sulfenyl, two (C1-C4Alkyl) amino sulfenyl, it is unsubstituted or by 1-5 such as The aryl carbonyl C that lower group replaces1-C4Alkyl, aryl carbonyl, aryloxycarbonyl, aryl C1-C4Alkyloxycarbonyl, aryl C1- C4Alkyl, Heteroarylcarbonyl C1-C4Alkyl, Heteroarylcarbonyl, Heteroaryloxycarbonyl, heteroaryl C1-C4Alkyloxycarbonyl, heteroaryl Base C1-C4Alkyl, following group are 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-C4Naphthenic base；
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 naphthenic base, unsubstituted or by 1-5 R10Substituted virtue Base, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl Carbonyl or Heteroaryloxycarbonyl.
5. substituted uracil compound according to claim 4, it is characterised in that: general formula I-1A, I-1B, I-1C, I-1D In shown compound:
R4、R5The identical or different hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, normal-butyl, secondary of being respectively selected from Butyl, isobutyl group, tert-butyl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy Or tert-butoxy；
R6、R7The identical or different hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, normal-butyl, secondary of being respectively selected from Butyl, isobutyl group, tert-butyl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy Or tert-butoxy；
R8、R9Identical or different is respectively selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, different Butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, one methyl fluoride of dichloro, methoxyl group, ethyoxyl, positive third oxygen Base, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methyl mercapto, ethylmercapto group, trifluoromethoxy, trifluoro Ethyoxyl, methoxycarbonyl, ethoxy carbonyl, amino carbonyl, methylaminocarbonyl, ethyl aminocarbonyl or dimethylamino carbonyl Base；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It may be the same or different；
W be selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tert-butyl, One methyl fluoride, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, methyl mercapto, ethylmercapto group, methyl Sulfonyl or ethylsulfonyl；
And when the compound is general formula I-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, tert-butyl, a methyl fluoride, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy, second Oxygroup methyl or trifluoroethoxy ylmethyl；
R2Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, carboxyl, formoxyl, methyl, ethyl, methoxyl group, ethyoxyl or Trifluoro ethoxy；
When the compound is general formula I-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, tert-butyl, trifluoromethyl, trifluoroethyl, methoxyl group, ethyoxyl, trifluoro Ethyoxyl, cyclopropyl oxygroup, methyl mercapto, ethylmercapto group, allyl, propargyl, mesyl, ethylsulfonyl, trifluoroethyl sulphonyl Base, aminosulfonyl, ethylamino sulfonyl, dimethylaminosulfonyl, lignocaine sulfonyl, methane sulfonylamino carbonyl, Methoxycarbonyl, ethoxy carbonyl, propoxycarbonyl, isopropoxy carbonyl, amino-carbonyl, dimethyl-aminocarbonyl, ethylene oxy Base carbonyl, acetylene Epoxide carbonyl, methylamino sulfenyl, ethylamino sulfenyl or dimethylamino sulfenyl；
When the compound is general formula I-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, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, dichloro One methyl fluoride, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, Trifluoromethoxy or trifluoro ethoxy；
When the compound is general formula I-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, tert-butyl, trifluoromethyl, trichloromethyl, difluoro chloromethyl, one methyl fluoride of dichloro, trifluoroethyl, methoxy Base, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, three It is fluorine ethyoxyl, unsubstituted or by 1-5 R10Substituted aryl, arylmethyl, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, Heteroaryl, heteroarylmethyl, Heteroarylcarbonyl, heteroarylmethyl carbonyl or Heteroaryloxycarbonyl.
6. substituted uracil compound according to claim 5, it is characterised in that: general formula I-1A, I-1B, I-1C, I-1D In shown compound:
R4、R5Identical or different is respectively selected from hydrogen, fluorine, chlorine, bromine or methyl；
R6、R7It is selected from hydrogen；
R8For hydrogen or methyl；
R9Selected from hydrogen or methyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxyl group, methyl mercapto or trifluoromethoxy；
N is selected from 0 to 5 integer, when n is 0, unsubstituted on phenyl ring；When n is greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl；
And when the compound is general formula I-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, 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. substituted uracil compound according to claim 6, it is characterised in that: general formula I-1A, I-1B, I-1C, I-1D In shown compound:
R4、R5It may be the same or different, be respectively selected from hydrogen or methyl；
R6、R7It is selected from hydrogen；
R8For hydrogen or methyl；
R9Selected from methyl；
R10Selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxyl group, methyl mercapto or trifluoromethoxy；
N is selected from 1 to 5 integer, when n is greater than 1, R10It may be the same or different；
W is selected from hydrogen, fluorine, chlorine, bromine or iodine；
And when the compound is general formula I-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, 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 of substituted uracil compound according to claim 1, it is characterised in that: general formula I shownization Close object the preparation method comprises the following steps:
9. a kind of substituted uracil compound described in accordance with the claim 1 is used as in agricultural or other field prepares fungicide The purposes of drug.
10. a kind of bactericidal composition, it is characterised in that: composition using substituted uracil compound described in claim 1 as Active component；Wherein, the weight percentage of active component is 0.1-99% in composition.
CN201711223040.2A 2017-11-29 2017-11-29 Substituted uracil compound and preparation method thereof and purposes as fungicide Pending CN109836417A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CN201711223040.2A CN109836417A (en) 2017-11-29 2017-11-29 Substituted uracil compound and preparation method thereof and purposes as fungicide
EP18882912.1A EP3719015A4 (en) 2017-11-29 2018-11-22 Substituted pyrimidine compound and preparation method therefor and use thereof
CN201880064173.6A CN111263757A (en) 2017-11-29 2018-11-22 Substituted pyrimidine compound and preparation method and application thereof
PCT/CN2018/116938 WO2019105275A1 (en) 2017-11-29 2018-11-22 Substituted pyrimidine compound and preparation method therefor and use thereof
US16/766,925 US11457628B2 (en) 2017-11-29 2018-11-22 Substituted pyrimidine compound and preparation method and use thereof
BR112020010921A BR112020010921A8 (en) 2017-11-29 2018-11-22 SUBSTITUTED PYRIMIDINE COMPOUND AND METHOD OF PREPARATION FOR IT AND ITS USE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201711223040.2A CN109836417A (en) 2017-11-29 2017-11-29 Substituted uracil compound and preparation method thereof and purposes as fungicide

Publications (1)

Publication Number Publication Date
CN109836417A true CN109836417A (en) 2019-06-04

Family

ID=66881788

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201711223040.2A Pending CN109836417A (en) 2017-11-29 2017-11-29 Substituted uracil compound and preparation method thereof and purposes as fungicide

Country Status (1)

Country Link
CN (1) CN109836417A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111263757A (en) * 2017-11-29 2020-06-09 沈阳中化农药化工研发有限公司 Substituted pyrimidine compound and preparation method and application thereof
WO2021104171A1 (en) * 2019-11-25 2021-06-03 沈阳中化农药化工研发有限公司 Bactericidal composition and use thereof
CN114304164A (en) * 2020-09-29 2022-04-12 沈阳中化农药化工研发有限公司 Bactericidal preparation and application thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104710409A (en) * 2013-12-13 2015-06-17 中国中化股份有限公司 Pyrazolyl pyrimidinamine compounds and application thereof
CN104710436A (en) * 2013-12-13 2015-06-17 中国中化股份有限公司 Pyrazolyl pyrilamine compound and use thereof
CN105777717A (en) * 2014-12-19 2016-07-20 沈阳中化农药化工研发有限公司 Pyrazolyl pyrimidinyl ether compound and use thereof
CN106167484A (en) * 2015-05-18 2016-11-30 沈阳中化农药化工研发有限公司 Substituted pyrazolecarboxylic compounds containing pyrimidine and its production and use
CN108069984A (en) * 2016-11-18 2018-05-25 沈阳中化农药化工研发有限公司 Substituted five-membered heterocycle compound of the ring containing pyrimido and its preparation method and application

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104710409A (en) * 2013-12-13 2015-06-17 中国中化股份有限公司 Pyrazolyl pyrimidinamine compounds and application thereof
CN104710436A (en) * 2013-12-13 2015-06-17 中国中化股份有限公司 Pyrazolyl pyrilamine compound and use thereof
CN105777717A (en) * 2014-12-19 2016-07-20 沈阳中化农药化工研发有限公司 Pyrazolyl pyrimidinyl ether compound and use thereof
CN106167484A (en) * 2015-05-18 2016-11-30 沈阳中化农药化工研发有限公司 Substituted pyrazolecarboxylic compounds containing pyrimidine and its production and use
CN108069984A (en) * 2016-11-18 2018-05-25 沈阳中化农药化工研发有限公司 Substituted five-membered heterocycle compound of the ring containing pyrimido and its preparation method and application

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111263757A (en) * 2017-11-29 2020-06-09 沈阳中化农药化工研发有限公司 Substituted pyrimidine compound and preparation method and application thereof
WO2021104171A1 (en) * 2019-11-25 2021-06-03 沈阳中化农药化工研发有限公司 Bactericidal composition and use thereof
CN114304164A (en) * 2020-09-29 2022-04-12 沈阳中化农药化工研发有限公司 Bactericidal preparation and application thereof

Similar Documents

Publication Publication Date Title
CN104710436B (en) A kind of pyrazolyl pyrimidines aminated compounds and purposes
RU2664576C1 (en) Mixtures of fungicidal pyrazole
DE60036290T2 (en) PYRAZOL DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF AND PESTICIDES CONTAINING THESE AS ACTIVE INGREDIENTS
CN107074779B (en) Pyridazine compounds
RU2451681C2 (en) Method of producing amide compound
CN111662269B (en) 1-pyridyl pyrazole amide compound and preparation method and application thereof
CN103781357A (en) Use of compound of pyrazole amides as agricultural fungicide
CN103467380B (en) Substituted phenyl pyrazole amide derivative and preparation method and application thereof
PL193231B1 (en) Pesticidal 1-aryl pyrazoles
ES2582330T3 (en) 4-Methylanilino-fungicidal pyrazoles
CN108059629A (en) Substituted pyrazolecarboxylic class compound containing pyrimidine and its preparation method and application
CN109836417A (en) Substituted uracil compound and preparation method thereof and purposes as fungicide
UA125313C2 (en) Pesticidal compounds
CN108069984A (en) Substituted five-membered heterocycle compound of the ring containing pyrimido and its preparation method and application
CN105777717B (en) Pyrazolyl pyrimidines ether compound and purposes
JP2006527172A (en) Use of isoindolinone derivatives as insecticides
EP1263734B1 (en) 3-thiomethylpyrazoles as pesticides
CN103772357B (en) Substituted pyrimidines compounds and uses thereof
CN1048035A (en) The N-phenylpyrazole derivatives
SK285808B6 (en) 1-Arylpyrazoles, pesticidal composition containing the same, method of controlling pests, and process for the preparation the same
CN105254625B (en) One kind class compound of yl-benzamide containing chloro-thiazole and its application
CN105777727B (en) 2- thiophene pyridine compounds and their and application thereof
CN104206385B (en) Use of amine compound as bactericide
CN108117528B (en) 2, 5-substituent-1, 3, 4-oxadiazole sulfone derivative, preparation method and application thereof
CN105541794A (en) Heptafluoroisopropyl-containing pyridyl pyrazole amide derivative and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination