CN104974136B - Pyrazol acid amide compounds and application thereof - Google Patents

Pyrazol acid amide compounds and application thereof Download PDF

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CN104974136B
CN104974136B CN201410131285.2A CN201410131285A CN104974136B CN 104974136 B CN104974136 B CN 104974136B CN 201410131285 A CN201410131285 A CN 201410131285A CN 104974136 B CN104974136 B CN 104974136B
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alkyl
hydrogen
halogen
formula
halo
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CN104974136A (en
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关爱莹
杨帆
王军锋
陈伟
李轲轲
孙旭峰
陈宣明
谢勇
宋玉泉
刘长令
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Abstract

The invention discloses pyrazol acid amide compounds, shown in compound structure below formula：

Description

Pyrazol acid amide compounds and application thereof
Technical field
The invention belongs to agricultural bactericidal, field of pesticides.More particularly to a kind of pyrazol acid amide compounds and application thereof.
Background technology
Patent US4950668A discloses tebufenpyrad（tebufenpyrad）Have Deng N- benzyl pyrazole acidamide derivatives Pesticide and miticide actility.Patent US5039693A discloses Tolfenpyrad（tolfenpyrad）The N- benzyl pyrroles replaced Deng phenoxy group Azoles amide derivatives have pesticide and miticide actility.Patent CN1927860A discloses the pyrazole amide analog derivative of benzene biaryl With pesticide and miticide actility.Reported without bactericidal activity.Patent WO02083647A1 discloses the pyrazol acid amide containing xenyl Derivative has sterilization, desinsection and acaricidal activity.
Patent US5039693 discloses the compound of below formula, with pesticide and miticide actility, but the patent is not disclosed It has bactericidal activity.
Patent EP0394043A1, US5264448A discloses the compound of below formula, with pesticide and miticide actility； JP2001064176 also discloses that the compound of below formula is only used as slimming agents.Wherein：A=pyrazole ring, B are pyridine Ring, it is identical with this logical formula (I) compound part, nevertheless, three patents do not have any bactericidal activity report.
Patent EP0365925A1 discloses the compound of below formula, with pesticide and miticide actility, although chemical combination in patent Thing is identical with this logical formula (I) compound part, but the patent is also reported without any bactericidal activity.
Patent WO2009024342A2 discloses the compound and particular compound CK1 of below formula（Numbering is in patent 1.581）, part of compounds is under 0.02% active constituent content to wheat powdery mildew, net blotch of barley, brown rust of wheat, wheat Balck shank preventive effect minimum 50%.
Patent WO02089583A1 discloses the compound and particular compound Tolfenpyrad of below formula（Numbered in patent For No.4）, CK2（Numbering is No.5 in patent）, CK3（Numbering is No.2 in patent）, CK4（Numbering is No.1 in patent）, tool There is bactericidal activity.
Patent WO02083647A1 discloses the compound and particular compound CK5 of below formula（Numbering is in patent No.18）, with sterilization, pesticide and miticide actility.
Following compound is also disclosed in patent WO2013064079, with bactericidal activity.
Patent US4968805（EP329020）Report following compound CK10 under 500ppm have good desinsection, Mite killing and bactericidal activity.Part of compounds also has good desinsection, mite killing and bactericidal activity under 50ppm.
The compound of above patent report belongs to Pyrazole Acyl benzylamine compound.
The patent CN103081916 of the present inventor's application（Numbering 169 (CK11), 519 (CK12) in patent）With CN103087041 (compound 98, CK13 in patent) discloses following compound, with good bactericidal activity.
In the prior art, compound of the structure as shown in formula of the present invention has no report.
The content of the invention
Modern agricultural production, which needs not turning off, sends structure novelty, the novel pesticide of excellent performance.It is an object of the invention to Offer is a kind of can just to control the pyrazol acid amide compounds of a variety of germs, insect under the dosage of very little, and it can be used for agricultural Or the medicine of anti-pathogen and insect evil mite is prepared in other field.
Technical scheme is as follows：
The present invention provides a kind of pyrazol acid amide compounds, and compound structure is as shown in formula：
Wherein：Q is selected fromOr
When Q (C=O) NAB- is connected to 5 of pyridine ring, compound is as shown in formula I；When Q (C=O) NAB- is connected to At 4 of pyridine ring, compound is as shown in formula II；When Q (C=O) NAB- is connected to 3 of pyridine ring, compound such as formula Shown in Ш：
In formula：
A is selected from hydrogen, hydroxyl, formoxyl, C1-C12Alkyl, halo C1-C12Alkyl, C1-C12Alkoxy, halo C1-C12Alcoxyl Base, C3-C12Cycloalkyl, C1-C12Alkylthio group, C2-C12Enylsulfanyl, C2-C12Alkenyl, C2-C12Alkynyl, halo C2-C12Alkenyl, halogen For C2-C12Alkynyl, C1-C12Alkoxy C1-C12Alkyl, halo C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12Alkane Base, halo C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl Sulfonyl, halo C1-C12Alkyl sulphonyl, C1-C12Alkyl amino sulfonyl, two (C1-C12Alkyl) amino-sulfonyl, C1-C12 Alkylsulfonyl aminocarbonyl, C1-C12Alkyl-carbonyl-amino sulfonyl, C3-C12Cycloalkyloxycarbonyl, C1-C12Alkyl-carbonyl, Halo C1-C12Alkyl-carbonyl, C1-C12Alkoxy carbonyl, halo 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) it is amino sulfenyl, unsubstituted or be further substituted with by the following groups of 1-5（It is miscellaneous）Aryl carbonyl C1-C6Alkyl,（It is miscellaneous）Virtue Base carbonyl,（It is miscellaneous）Aryloxycarbonyl,（It is miscellaneous）Aryl C1-C6Alkyloxycarbonyl or（It is miscellaneous）Aryl C1-C6Alkyl：Halogen, nitro, Cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxy or halo C1-C6Alkoxy；
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen is joined directly together with pyridine ring 3,4 or 5 carbon2CRaRb- or- CH2CRaRbCRaRb-；
Ra、RbIt may be the same or different, be respectively selected from hydrogen, C1-C12Alkyl, C3-C12Cycloalkyl, C2-C12Alkenyl, C2-C12Alkynes Base, halo C2-C12Alkenyl, halo C2-C12Alkynyl, C1-C12Alkoxy C1-C12It is alkyl, unsubstituted or by the following groups of 1-5 The aryl C being further substituted with1-C6Alkyl or heteroaryl C1-C6Alkyl：Halogen, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkane Epoxide or halo C1-C6Alkoxy, or Ra, RbC is constituted with the carbon being connected3-C8Ring；
X is selected from O or S；
R1、R2、R3、R4、R5It may be the same or different, be respectively selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C1- C12Alkyl, halo C1-C12Alkyl, C1-C12Alkoxy, halo C1-C12Alkoxy, C3-C12Cycloalkyl, C2-C12Alkenyl, C2-C12 Alkynyl, C2-C12Alkenyloxy group, halo C2-C12Alkenyloxy group, C2-C12Alkynyloxy group, halo C2-C12Alkynyloxy group, C1-C12Alkylthio group, halo C1-C12Alkylthio group, C1-C12Alkoxy C1-C12Alkyl, halo C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12Alkane Base, halo C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl Sulfonyl, halo C1-C12Alkyl sulphonyl, C1-C12Alkyl amino sulfonyl, C1-C12Alkyl amino, halo C1-C12Alkyl ammonia Base, two (C1-C12Alkyl) amino, C1-C12Alkoxy carbonyl, CONH2、C1-C12Alkyl amino-carbonyl, two (C1-C12Alkyl) ammonia Base carbonyl, cyano group C1-C12Alkoxy, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkyl amino-carbonyl C1-C12Alkyl or Two (C1-C12Alkyl) amino carbonyl C1-C12Alkyl；
R6、R6'、R7It may be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C12Alkyl, halo C1-C12Alkane Base, C3-C12Cycloalkyl, C1-C12Alkoxy, halo C1-C12Alkoxy, C1-C12Alkylthio group, halo C1-C12Alkylthio group, C2-C12 Alkenyl, halo C2-C12Alkenyl, C2-C12Alkynyl, halo C2-C12Alkynyl, C3-C12Alkenyloxy group, halo C3-C12Alkenyloxy group, C3-C12 Alkynyloxy group, halo C3-C12Alkynyloxy group, C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl sulfonyl Base, halo C1-C12Alkyl sulphonyl, C1-C12Alkyl-carbonyl, halo C1-C12Alkyl-carbonyl, C1-C12Alkyl carbonyl epoxide, C1- C12Alkyl-carbonyl-amino, C1-C12Alkyl sulphonyl epoxide, C1-C12Alkoxy carbonyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkoxycarbonyl amino, C1-C12Alkoxy C1-C12Alkoxy or C1-C12Alkoxy carbonyl C1-C12Alkoxy；
R8Selected from hydrogen, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxy C1-C8Alkyl, cyano group C1-C8Alkyl or C3- C6Cycloalkyl, aryl or heteroaryl unsubstituted or be further substituted with by 1-5 following groups：Halogen, cyano group, nitro, C1- C6Alkyl, C1-C6Alkoxy, C1-C6Alkylthio group, C3-C6Cycloalkyl, C2-C6Alkenyl, C2-C6Alkynyl, halo C1-C6Alkyl, halo C1-C6Alkoxy, halo C1-C6Alkylthio group, halo C3-C6Cycloalkyl, halo C2-C6Alkenyl, halo C2-C6Alkynyl, C1-C6Alkyl Sulfinyl, C1-C6Alkyl sulphonyl, C1-C6Alkyl amino, two (C1-C6Alkyl) amino, C1-C6Alkyl-carbonyl, C1-C6Alcoxyl Base carbonyl, C1-C6It is alkyl amino-carbonyl, unsubstituted or the aryl or miscellaneous that following group is further substituted with is independently selected from by 1-5 Aryl：Hydrogen, halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxy or halo C1-C6Alkoxy；
R9Selected from hydrogen, halogen, cyano group, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxy, halo C1-C8Alkoxy, Cyano group C1-C8Alkyl, cyano group C1-C8Alkoxy, C3-C8Alkenyloxy group, halo C3-C8Alkenyloxy group, C3-C8Alkynyloxy group, halo C3-C8Alkynes Epoxide, C1-C8Alkylthio group, halo C1-C8Alkylthio group, C1-C8Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C8Alkane Base sulfonyl, halo C1-C8It is alkyl sulphonyl, unsubstituted or the benzene that following group is further substituted with is independently selected from by 1-5 Base：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxy, halo C1-C8Alkane Epoxide, C1-C8Alkylthio group, C3-C8Cycloalkyl, C2-C8Alkenyl, C2-C8Alkynyl, halo C1-C8Alkylthio group, halo C3-C8Cycloalkyl, Halo C2-C8Alkenyl, halo C2-C8Alkynyl, C1-C8Alkyl sulphinyl, C1-C8Alkyl sulphonyl, C1-C8Alkyl amino, two (C1-C8Alkyl) amino, C1-C8Alkyl-carbonyl, C1-C8Alkoxy carbonyl or C1-C8Alkyl amino-carbonyl；
R10Selected from hydrogen, halogen, cyano group, nitro, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxy, halo C1-C8Alkane Epoxide, C1-C8Alkylthio group, halo C1-C8Alkylthio group, C1-C8Alkyl sulphinyl, halo C1-C8Alkyl sulphinyl, C1-C8Alkane Base sulfonyl or halo C1-C8Alkyl sulphonyl；
R10' it is selected from hydrogen, halogen, cyano group, C1-C8Alkyl, halo C1-C8Alkyl, cyano group C1-C8Alkyl or C3-C6Cycloalkyl；
And the present invention does not include following 3 compounds（Chemistry&Biology.2010,17:Chemical combination in 686-694 Compound A and B in thing 2 and WO9924404）：
Currently preferred compound as shown in formula I, II or III, wherein
A is selected from hydrogen, hydroxyl, formoxyl, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxy, halo C1-C8Alkoxy, C3-C8Cycloalkyl, C1-C8Alkylthio group, C2-C8Enylsulfanyl, C2-C8Alkenyl, C2-C8Alkynyl, halo C2-C8Alkenyl, halo C2-C8 Alkynyl, C1-C8Alkoxy C1-C8Alkyl, halo C1-C8Alkoxy C1-C8Alkyl, C1-C8Alkylthio group C1-C8Alkyl, halo C1-C8 Alkylthio group C1-C8Alkyl, C1-C8Alkyl sulphinyl, halo C1-C8Alkyl sulphinyl, C1-C8Alkyl sulphonyl, halo C1- C8Alkyl sulphonyl, C1-C8Alkyl amino sulfonyl, two (C1-C8Alkyl) amino-sulfonyl, C1-C8Alkyl sulfonyl-amino carbonyl Base, C1-C8Alkyl-carbonyl-amino sulfonyl, C3-C8Cycloalkyloxycarbonyl, C1-C8Alkyl-carbonyl, halo C1-C8Alkyl-carbonyl, C1-C8Alkoxy carbonyl, halo C1-C8Alkoxy carbonyl, C1-C8Alkyl-carbonyl C1-C8Alkyl, C1-C8Alkoxy carbonyl C1-C8Alkane Base, C1-C8Alkyl amino-carbonyl, two (C1-C8Alkyl) amino carbonyl, C2-C8Allyloxycarbonyl, C2-C8Alkynyloxycar bonyl, C1-C8 Alkoxy C1-C8Alkoxy carbonyl, C1-C8Alkyl amino sulfenyl, two（C1-C8Alkyl）It is amino sulfenyl, unsubstituted or by 1-3 What following group was further substituted with（It is miscellaneous）Aryl carbonyl C1-C6Alkyl,（It is miscellaneous）Aryl carbonyl,（It is miscellaneous）Aryloxycarbonyl,（It is miscellaneous）Aryl C1-C6Alkyloxycarbonyl or（It is miscellaneous）Aryl C1-C6Alkyl：Halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkyl, C1- C4Alkoxy or halo C1-C4Alkoxy；
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen is joined directly together with pyridine ring 3,4 or 5 carbon2CRaRb- or- CH2CRaRbCRaRb-；
Ra、RbIt may be the same or different, be respectively selected from hydrogen, C1-C8Alkyl, C3-C8Cycloalkyl, C2-C8Alkenyl, C2-C8Alkynyl, Halo C2-C8Alkenyl, halo C2-C8Alkynyl, C1-C8Alkoxy C1-C8It is alkyl, unsubstituted or further by the following groups of 1-3 Substituted aryl C1-C4Alkyl or heteroaryl C1-C4Alkyl：Halogen, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy or Halo C1-C4Alkoxy；Or Ra、RbC is constituted with the carbon being connected3-C8Ring；
X is selected from O or S；
R1、R2、R3、R4、R5It may be the same or different, be respectively selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C1- C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxy, halo C1-C8Alkoxy, C3-C8Cycloalkyl, C2-C8Alkenyl, C2-C8Alkynyl, C2-C8Alkenyloxy group, halo C2-C8Alkenyloxy group, C2-C8Alkynyloxy group, halo C2-C8Alkynyloxy group, C1-C8Alkylthio group, halo C1-C8Alkane sulphur Base, C1-C8Alkoxy C1-C8Alkyl, halo C1-C8Alkoxy C1-C8Alkyl, C1-C8Alkylthio group C1-C8Alkyl, halo C1-C8Alkane Sulfenyl C1-C8Alkyl, C1-C8Alkyl sulphinyl, halo C1-C8Alkyl sulphinyl, C1-C8Alkyl sulphonyl, halo C1-C8 Alkyl sulphonyl, C1-C8Alkyl amino sulfonyl, C1-C8Alkyl amino, halo C1-C8Alkyl amino, two (C1-C8Alkyl) ammonia Base, C1-C8Alkoxy carbonyl, CONH2、C1-C8Alkyl amino-carbonyl, two (C1-C8Alkyl) amino carbonyl, cyano group C1-C8Alcoxyl Base, C1-C8Alkoxy carbonyl C1-C8Alkyl, C1-C8Alkyl amino-carbonyl C1-C8Alkyl or two (C1-C8Alkyl) amino carbonyl C1- C8Alkyl；
R6、R6'、R7It may be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C8Alkyl, halo C1-C8Alkane Base, C3-C6Cycloalkyl, C1-C8Alkoxy, halo C1-C8Alkoxy, C1-C8Alkylthio group, halo C1-C8Alkylthio group, C2-C8Alkenyl, Halo C2-C8Alkenyl, C2-C8Alkynyl, halo C2-C8Alkynyl, C3-C8Alkenyloxy group, halo C3-C8Alkenyloxy group, C3-C8Alkynyloxy group, halogen For C3-C8Alkynyloxy group, C1-C8Alkyl sulphinyl, halo C1-C8Alkyl sulphinyl, C1-C8Alkyl sulphonyl, halo C1-C8 Alkyl sulphonyl, C1-C8Alkyl-carbonyl, halo C1-C8Alkyl-carbonyl, C1-C8Alkyl carbonyl epoxide, C1-C8Alkyl-carbonyl-amino, C1-C8Alkyl sulphonyl epoxide, C1-C8Alkoxy carbonyl, C1-C8Alkoxy carbonyl C1-C8Alkyl, C1-C8Alkoxy carbonyl ammonia Base, C1-C8Alkoxy C1-C8Alkoxy or C1-C8Alkoxy carbonyl C1-C8Alkoxy；
R8Selected from hydrogen, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxy C1-C3Alkyl, cyano group C1-C6Alkyl or C3- C6Cycloalkyl, aryl or heteroaryl unsubstituted or be further substituted with by 1-5 following groups：Halogen, cyano group, nitro, C1- C4Alkyl, C1-C4Alkoxy, C1-C4Alkylthio group, C3-C6Cycloalkyl, C2-C4Alkenyl, C2-C4Alkynyl, halo C1-C4Alkyl, halo C1-C4Alkoxy, halo C1-C4Alkylthio group, halo C3-C6Cycloalkyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkyl Sulfinyl, C1-C4Alkyl sulphonyl, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl-carbonyl, C1-C4Alcoxyl Base carbonyl, C1-C4It is alkyl amino-carbonyl, unsubstituted or phenyl or pyrrole that following group is further substituted with are independently selected from by 1-5 Piperidinyl：Hydrogen, halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy or halo C1-C4Alkoxy；
R9Selected from hydrogen, halogen, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxy, halo C1-C6Alkoxy, Cyano group C1-C6Alkyl, cyano group C1-C6Alkoxy, halo C1-C6Alkylthio group, halo C1-C6Alkyl sulphinyl, halo C1-C6Alkane It is base sulfonyl, unsubstituted or the phenyl that following group is further substituted with is independently selected from by 1-5：Halogen, cyano group, nitro, hydroxyl Base, amino, sulfydryl, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxy, halo C1-C6Alkoxy, C1-C6Alkylthio group, C3- C6Cycloalkyl, C2-C6Alkenyl, C2-C6Alkynyl, halo C1-C6Alkylthio group, halo C3-C6Cycloalkyl, halo C2-C6Alkenyl, halo C2-C6Alkynyl, C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, C1-C6Alkyl amino, two (C1-C6Alkyl) amino, C1-C6 Alkyl-carbonyl, C1-C6Alkoxy carbonyl or C1-C6Alkyl amino-carbonyl；
R10Selected from hydrogen, halogen, cyano group, nitro, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxy, halo C1-C6Alkane Epoxide, C1-C6Alkylthio group, halo C1-C6Alkylthio group, C1-C6Alkyl sulphinyl, halo C1-C6Alkyl sulphinyl, C1-C6Alkane Base sulfonyl or halo C1-C6Alkyl sulphonyl；
R10' it is selected from hydrogen, halogen, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, cyano group C1-C6Alkyl or C3-C6Cycloalkyl.
The further preferred compound of the present invention as shown in formula I, II or III, wherein
A is selected from hydrogen, C1-C4Alkyl, C1-C4Alkoxy carbonyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl Base, C1-C4Alkyl-carbonyl C1-C4Alkyl；
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen is joined directly together with pyridine ring 3,4 or 5 carbon2CRaRb- or- CH2CRaRbCRaRb-；
Ra、RbIt may be the same or different, be respectively selected from hydrogen, methyl or ethyl；
X is selected from O or S；
R1、R2、R3、R4、R5It may be the same or different, be respectively selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C1- C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy, halo C1-C4Alkoxy, C3-C4Cycloalkyl, C2-C4Alkenyl, C2-C4Alkynyl, C2-C4Alkenyloxy group, halo C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halo C2-C4Alkynyloxy group, C1-C4Alkylthio group, halo C1-C4Alkane sulphur Base, C1-C4Alkoxy C1-C4Alkyl, halo C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkane Sulfenyl C1-C4Alkyl, C1-C4Alkyl sulphinyl, halo C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halo C1-C4 Alkyl sulphonyl, C1-C4Alkyl amino sulfonyl, C1-C4Alkyl amino, halo C1-C4Alkyl amino, two (C1-C4Alkyl) ammonia Base, C1-C4Alkoxy carbonyl, CONH2、C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, cyano group C1-C12Alcoxyl Base, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl C1-C4Alkyl or two (C1-C4Alkyl) amino carbonyl C1- C4Alkyl；
R6、R6'、R7It may be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkane Base, C3-C6Cycloalkyl, C1-C4Alkoxy, halo C1-C4Alkoxy, C1-C4Alkylthio group, halo C1-C4Alkylthio group, C2-C4Alkenyl, C2-C4Alkynyl, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, C1-C4Alkyl-carbonyl or C1-C4Alkoxy C1-C4Alcoxyl Base；
R8Selected from hydrogen, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy C1-C3Alkyl, cyano group C1-C4Alkyl, C3-C6 Cycloalkyl, aryl or heteroaryl unsubstituted or be further substituted with by 1-5 following groups：Halogen, cyano group, nitro, C1-C4 Alkyl, C1-C4Alkoxy, C1-C4Alkylthio group, C3-C6Cycloalkyl, C2-C4Alkenyl, C2-C4Alkynyl, halo C1-C4Alkyl, halo C1-C4Alkoxy, halo C1-C4Alkylthio group, halo C3-C6Cycloalkyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkyl Sulfinyl, C1-C4Alkyl sulphonyl, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl-carbonyl, C1-C4Alcoxyl Base carbonyl, C1-C4It is alkyl amino-carbonyl, unsubstituted or phenyl or pyrrole that following group is further substituted with are independently selected from by 1-5 Piperidinyl：Hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy or halo C1-C4Alkoxy；
R9Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy, halo C1-C4Alkoxy, Cyano group C1-C4Alkyl, cyano group C1-C4Alkoxy, halo C1-C4Alkylthio group, halo C1-C4Alkyl sulphinyl, halo C1-C4Alkane It is base sulfonyl, unsubstituted or the phenyl that following group is further substituted with is independently selected from by 1-5：Halogen, cyano group, nitro, hydroxyl Base, amino, sulfydryl, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy, halo C1-C4Alkoxy, C1-C4Alkylthio group, C3- C6Cycloalkyl, C2-C4Alkenyl, C2-C4Alkynyl, halo C1-C4Alkylthio group, halo C3-C6Cycloalkyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4 Alkyl-carbonyl, C1-C4Alkoxy carbonyl or C1-C4Alkyl amino-carbonyl；
R10Selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy, halo C1-C4Alkane Epoxide, C1-C4Alkylthio group, halo C1-C4Alkylthio group, C1-C4Alkyl sulphinyl, halo C1-C4Alkyl sulphinyl, C1-C4Alkane Base sulfonyl or halo C1-C4Alkyl sulphonyl；
R10' it is selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4Alkyl, cyano group C1-C4Alkyl or C3-C6Cycloalkyl.
Present invention compound still further preferably as shown in formula I, II or III, wherein
Link position of the fixed amide nitrogen atom through B and pyridine ring 3,4 or 5 carbon atoms, while further reducing Q substitutions R8 protection domain on base, respectively obtains six kinds of formulas such as I-A, I-B, I-C, I-D, II-A or Ш-A（Formula I-A, I- R8 is selected from hydrogen, C in B, II-A, Ш-A1-C4Alkyl or C3-C6Cycloalkyl, i.e. R8'；R8 is selected from unsubstituted in formula I-C, I-D Or the phenyl or pyridine radicals further independently replaced by 1-5 substituent）：
Therefore, the compound in the present invention still more preferably is：In formula I-A, I-B, I-C, I-D, II-A or Ш-A
A is selected from hydrogen；
Ra、RbIt may be the same or different, be respectively selected from hydrogen, methyl or ethyl；
R1、R2、R3、R4、R5It may be the same or different, be respectively selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4 Alkoxy or halo C1-C4Alkoxy；
R6、R6'、R7It may be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkane Base, C1-C4Alkoxy, halo C1-C4Alkoxy or C1-C4Alkyl-carbonyl；
R8' it is selected from hydrogen, C1-C4Alkyl or C3-C6Cycloalkyl；
R9Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy, halo C1-C4Alkoxy, Cyano group C1-C3Alkyl, cyano group C1-C3Alkoxy, halo C1-C3Alkylthio group, halo C1-C3Alkyl sulphinyl, halo C1-C3Alkane It is base sulfonyl, unsubstituted or the phenyl that following group is further substituted with is independently selected from by 1-3：Halogen, cyano group, nitro, C1- C4Alkyl, C1-C4Alkoxy, C1-C4Alkylthio group, C3-C6Cycloalkyl, C2-C4Alkenyl, C2-C4Alkynyl, halo C1-C4Alkyl, halo C1-C4Alkoxy, halo C1-C4Alkylthio group, halo C3-C6Cycloalkyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkyl Sulfinyl, C1-C4Alkyl sulphonyl, C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-C4Alkyl-carbonyl, C1-C4Alcoxyl Base carbonyl or C1-C4Alkyl amino-carbonyl；
R10Selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C4Alkyl, halo C1-C4Alkylthio group or halo C1-C4Alkyl sulphinyl；
R10' it is selected from hydrogen, halogen, cyano group, C1-C4Alkyl or halo C1-C4Alkyl；
R11、R12、R13、R14It may be the same or different, be respectively selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4Alkyl Or halo C1-C4Alkoxy；
Y is selected from N or CR15, wherein R15Selected from hydrogen, halogen, C1-C4Alkyl or halo C1-C4Alkyl.
Change in the compound of the present invention still more preferably shown in mutual-through type I-A, I-B, I-C, I-D, II-A or Ш-A Compound substituent is preferably:
A、Ra、Rb、R6、R6'、R7It is selected from hydrogen；
R1、R2、R3、R4、R5It may be the same or different, be respectively selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl or C1-C4 Alkoxy；
R8' it is selected from C1-C4Alkyl；
R9Selected from halogen, C1-C4Alkyl or halo C1-C4Alkyl；
R10Or R10' it is selected from hydrogen, halogen or C1-C4Alkyl；
R11、R12、R13、R14It may be the same or different, be respectively selected from hydrogen or halogen；
Y is selected from N.
Change in the compound of the present invention still more preferably shown in mutual-through type I-A, I-B, I-C, I-D, II-A or Ш-A Compound substituent more preferably：
A、Ra、Rb、R6、R6'、R7It is selected from hydrogen；
In formula I-A, R1、R10Selected from hydrogen or halogen；R2Selected from hydrogen, halogen or C1-C4Alkyl；R3Selected from hydrogen, halogen or halogen For C1-C4Alkyl；R4Selected from hydrogen, halogen, C1-C4Alkyl, C1-C4Alkoxy or halo C1-C4Alkyl；R5Selected from hydrogen；R8'、R9Choosing From C1-C4Alkyl；
In formula I-B, R1、R2、R3、R5Selected from hydrogen；R4Selected from halogen；R8' it is selected from C1-C4Alkyl；R9Selected from C1-C4Alkyl or Halo C1-C4Alkyl；R10' it is selected from hydrogen or C1-C4Alkyl；
In formula I-C, Y=N；R1Selected from hydrogen or halo C1-C4Alkyl；R2Selected from hydrogen or halogen；R3、R5、R10、R12、R13、H14 Selected from hydrogen；R4Selected from hydrogen, halogen, C1-C4Alkyl, C1-C4Alkoxy or halo C1-C4Alkyl；R9、R11Selected from halogen；
In formula I-D, Y=N；R1、R3、R5Selected from hydrogen or halogen；R2、R10、R12、R13、H14Selected from hydrogen；R4Selected from hydrogen or C1- C4Alkyl；R9、R11Selected from halogen；
In formula II-A, R1、R2、R3、R5Selected from hydrogen；R4、R10Selected from halogen；R8'、R9Selected from C1-C4Alkyl；
In general formula III-A, R1、R2、R3、R5Selected from hydrogen；R4Selected from hydrogen or halogen；R8'、R9Selected from C1-C4Alkyl；R10It is selected from Halogen.
Change in the compound of the present invention still more preferably shown in mutual-through type I-A, I-B, I-C, I-D, II-A or Ш-A Compound substituent much further preferably from：
A、Ra、Rb、R6、R6'、R7It is selected from hydrogen；
In formula I-A, R1、R10Selected from hydrogen or chlorine；R2Selected from hydrogen, chlorine or methyl；R3Selected from hydrogen, chlorine or trifluoromethyl；R4Choosing From hydrogen, chlorine, methyl, methoxyl group or trifluoromethyl；R5Selected from hydrogen；R8' it is selected from methyl；R9Selected from methyl or ethyl；
In formula I-B, R1、R2、R3、R5Selected from hydrogen；R4Selected from chlorine；R8' it is selected from methyl；R9Selected from methyl or trifluoromethyl； R10' it is selected from hydrogen or methyl；
In formula I-C, Y=N；R1Selected from hydrogen or trifluoromethyl；R2Selected from hydrogen or chlorine；R3、R5、R10、R12、R13、H14It is selected from Hydrogen；R4Selected from hydrogen, chlorine, methyl, methoxyl group or trifluoromethyl；R9Selected from bromine；R11Selected from chlorine；
In formula I-D, Y=N；R1、R3、R5Selected from hydrogen or chlorine；R2、R10、R12、R13、H14Selected from hydrogen；R4Selected from hydrogen or methyl； R9Selected from bromine；R11Selected from chlorine；
In formula II-A, R1、R2、R3、R5Selected from hydrogen；R4、R10Selected from chlorine；R8' it is selected from methyl；R9Selected from methyl or ethyl；
In general formula III-A, R1、R2、R3、R5Selected from hydrogen；R4Selected from hydrogen or chlorine；R8'、R9Selected from methyl；R10Selected from chlorine.
Compound substituent in the compound of the present invention still more preferably shown in mutual-through type I-A, I-B, I-C or I-D Be still more preferably：
A、Ra、Rb、R6、R6'、R7It is selected from hydrogen；
In formula I-A, R1、R10Selected from hydrogen or chlorine；R2Selected from hydrogen, chlorine or methyl；R3Selected from hydrogen, chlorine or trifluoromethyl；R4Choosing From hydrogen, chlorine, methyl, methoxyl group or trifluoromethyl；R5Selected from hydrogen；R8' it is selected from methyl；R9Selected from methyl or ethyl；
In formula I-B, R1、R2、R3、R5Selected from hydrogen；R4Selected from chlorine；R8'、R9、R10' it is selected from methyl；
In formula I-C, Y=N；R1Selected from hydrogen or trifluoromethyl；R2Selected from hydrogen or chlorine；R3、R5、R10、R12、R13、H14It is selected from Hydrogen；R4Selected from hydrogen, chlorine or methyl；R9Selected from bromine；R11Selected from chlorine；
In formula I-D, Y=N；R1、R3、R5Selected from hydrogen or chlorine；R2、R10、R12、R13、H14Selected from hydrogen；R4Selected from hydrogen or methyl； R9Selected from bromine；R11Selected from chlorine；
In general formula III-A, R1、R2、R3、R5Selected from hydrogen；R4Selected from hydrogen or chlorine；R8'、R9Selected from methyl；R10Selected from chlorine.
In the definition of formula I, II or Ш compound given above, collect the following substituent of term general proxy used：
Halogen：Refer to fluorine, chlorine, bromine or iodine.Alkyl：Straight or branched alkyl, such as methyl, ethyl, propyl group, isopropyl or uncle Butyl.Cycloalkyl：Substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopenta or cyclohexyl.Substituent such as methyl, halogen Element etc..Haloalkyl：Straight or branched alkyl, the hydrogen atom on these alkyl partly or entirely can be replaced by halogen atom, For example, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl etc..Alkoxy：Straight or branched alkane Base, is connected in structure through oxygen atom key.Halogenated alkoxy：Straight or branched alkoxyl, the hydrogen atom on these alkoxies Partly or entirely it can be replaced by halogen atom.For example, chloromethane epoxide, dichloro methoxyl group, trichloromethoxy, fluorine methoxyl group, difluoro Methoxyl group, trifluoromethoxy, chlorine fluorine methoxyl group, trifluoro ethoxy etc..Alkylthio group：Straight or branched alkyl, connects through sulphur atom key It is connected in structure.Halogenated alkylthio：Straight or branched alkylthio group, the hydrogen atom on these alkyl can be partly or entirely former by halogen Son is replaced, such as chloromethane sulfenyl, dichloro methyl mercapto, trichloro-methylthio, fluorine methyl mercapto, difluoro methyl mercapto, trifluoromethylthio, chlorine Fluorine methyl mercapto etc..Cyanoalkyl：CN- alkyl, such as CNCH3, CNC2H5.Cyano alkoxy：CN- alkoxies, such as CNCH3O, CNC2H5O.Alkenyl：Straight or branched alkenes, such as vinyl, 1- acrylic, 2- acrylic and different cyclobutenyls, pentenyl And hexenyl isomers.Alkenyl also includes many alkenes, such as 1,2- allene base and 2,4- hexadienyl.Haloalkenyl group：Straight chain or Branch chain alkene, the hydrogen atom on these alkenyls partly or entirely can be replaced by halogen atom.Alkynyl：Straight or branched acetylenic, Such as acetenyl, 1- propinyls, 2-propynyl and different butynyls, pentynyl and hexynyl isomers.Alkynyl also include by The group of multiple three keys compositions, such as 2,5- adipic alkynyls.Halo alkynyl：Straight or branched acetylenic, the hydrogen on these alkynyls is former Son partly or entirely can be replaced by halogen atom.Alkenyloxy group：Straight or branched alkenes, are connected in structure through oxygen atom key.Alkene Base sulfenyl：Straight or branched alkenes, are connected in structure through sulphur atom key.Such as CH2=CHCH2S-.Halo alkenyloxy group：Straight chain or branch Alkenyloxy, the hydrogen atom in these alkenyloxy groups partly or entirely can be replaced by halogen atom.Alkynyloxy group：Straight or branched alkynes Class, is connected in structure through oxygen atom key.Halo alkynyloxy group：Straight or branched alkynyloxy group, the hydrogen atom on these alkynyloxy groups Partly or entirely it can be replaced by halogen atom.Allyloxycarbonyl：Such as CH2=CHCH2OCO- etc..Alkynyloxycar bonyl：Such as CH ≡ CCH2OCO- etc..Alkyl amino：Straight or branched alkyl, is connected in structure through nitrogen-atoms key.Haloalkylamino：Straight chain or Branched alkyl amino, the hydrogen atom on these alkyl partly or entirely can be locked by halogen atom to be replaced.Alkyl sulphinyl：Straight chain Or branched alkyl is through sulfinyl（-SO-）It is connected in structure, such as methylsulfinyl.Alkylsulfinyl：Straight chain or Hydrogen atom on branched alkyl sulfinyl, its alkyl partly or entirely can be replaced by halogen atom.Alkyl sulphonyl：Straight chain or Branched alkyl is through sulfonyl（-SO2-）It is connected in structure, such as methyl sulphonyl.Halogenated alkyl sulfonyl：Straight or branched alkane Hydrogen atom on base sulfonyl, its alkyl partly or entirely can be replaced by halogen atom.Alkyl-carbonyl：Alkyl is connected to through carbonyl In structure, such as CH3CO-, CH3CH2CO-.Halogenated alkyl carbonyl：Hydrogen atom on the alkyl of alkyl-carbonyl can part or all of quilt Halogen atom is replaced, such as CF3CO-.Alkyl-carbonyl-amino：Such as CH3CONH-, CH3CH2NHCONH-.Alkyl sulphonyl epoxide：Alkane Base-S (O)2-O-.Alkoxy carbonyl：Alkyl-O-CO-, such as CH3OCO-, C2H5OCO-.Alkyl carbonyl epoxide：Such as CH3COO-, CH3CH2NHCOO-.Halo alkoxy carbonyl：Hydrogen atom on the alkyl of alkoxy carbonyl partly or entirely can be taken by halogen atom Generation, such as ClCH2CH2OCO-、CF3CH2OCO- etc..Alkoxy carbonyl alkyl：Alkoxy carbonyl-alkyl-, such as CH3OCOCH2-。 Alkoxycarbonyl amino：Alkyl-O-CO-NH-.Alkoxyalkyl：Alkyl-O- alkyl-, such as CH3OCH2-.Alkoxy alcoxyl Base：Alkyl-O- alkyl-O-, such as CH3OCH2O-.Dialkyl amido：Such as (CH3)2NH-, (C2H5)2NH-.Halogenated alkoxy Alkyl：Hydrogen atom on the alkyl of alkoxyalkyl partly or entirely can be replaced by halogen atom.Such as ClCH2CH2OCH2-.Alkane sulphur Base alkyl：Alkyl-S-alkyl-, such as CH3SCH2-.Haloalkylthioalkyl：Hydrogen atom on the alkyl of alkylthio alkyl can portion Divide or all replaced by halogen atom, such as ClCH2CH2SCH2-、CF3CH2SCH2- etc..Alkyl amino sulfonyl：Alkyl-NH- SO2-.Dialkyl amino sulfonyl：(alkyl)2-N-SO2-.Alkylsulfonyl aminocarbonyl：Alkyl-SO2-NH-CO-.Alkyl ammonia Base carbonylic alkyl：Such as CH3NH2COCH2-.Alkoxycarbonylalkoxy：Alkyl-O-CO- alkyl-O-.Alkyl-carbonyl-amino sulphur Acyl group：Alkyl-CO-NH-SO2-.Cycloalkyloxycarbonyl：Such as ring propoxycarbonyl, cyclohexyloxy carbonyl.Alkyl-carbonyl alkane Base：Alkyl-CO- alkyl-.Alkyl amino-carbonyl：Alkyl-NH-CO-, such as CH3NHCO-, (CH3)2NCO-.Dialkyl amido carbonyl Base：(alkyl)2- NH-CO-, such as (CH3)2-N-CO-、(C2H5)2-N-CO-.Alkoxyalkoxycarbonyl：Such as CH3O CH2CH2OCO- etc..Alkyl amino sulfenyl：Such as CH3NHS-、C2H5NHS-.Dialkyl amido sulfenyl：Such as (CH3)2NS-、(C2H5)2NS-.（It is miscellaneous）Aryl alkyl carbonyl,（It is miscellaneous）Aryl carbonyl,（It is miscellaneous）Aryloxycarbonyl,（It is miscellaneous）Aryl alkyl Epoxide carbonyl,（It is miscellaneous）Virtue Aryl moiety in base alkyl is including phenyl or naphthyl etc..Heteroaryl is to contain the heteroatomic five-membered ring of one or more N, O, S or six Yuan of rings.Such as furyl, pyrazolyl, thiazolyl, pyridine radicals, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, quinolyl. （It is miscellaneous）Aryl alkyl carbonyl：Such as PhCOCH2-.（It is miscellaneous）Aryl carbonyl：As benzoyl, 4- chlorobenzene formacyls, picolinoyl, Pyrimidine formoxyl, pyrazoyl etc..（It is miscellaneous）Aryloxycarbonyl：Such as phenyloxycarbonyl, 4- cHorophenoxycarbonyls, 4- nitrobenzene oxygen Base carbonyl, naphthoxycarbonyl, pyridine Epoxide carbonyl, 2-pyrimidinyl oxy carbonyl etc..（It is miscellaneous）Aryl alkyl Epoxide carbonyl：Such as benzyl epoxide Carbonyl, 4- chlorobenzyls Epoxide carbonyl, 4- trifluoromethyl benzyls Epoxide carbonyl, picolyl Epoxide carbonyl etc..（It is miscellaneous）Aryl alkyl： As benzyl, phenethyl, to chlorophenylmethyl,Deng.
Table 1 to table 4 lists R in formula I, II or Ш respectively8、R9、R10、Ra、RbThe specific substituent in part, but they It is not limited only in these substituents, formula I, II or Ш other substituents as previously described.
Table 1R8Substituent
Table 2R9Substituent
Table 3R10（R10'）Substituent
R10 R10
H CF3
Cl OCF3
Br NO2
CH3 CH2Cl
OCH3 CN
SCH3 SO2CH3
SCF3 SOCF3
Table 4Ra（Rb）Substituent
The part of compounds of the present invention can be with the particular compound listed in table 5- tables 116 to illustrate, but does not limit The present invention.In general formula compound I-A, I-B, I-C, I-D, II-A or Ш-A being related to, R6=R6'=H。
Formula I-A chemical formulas are as follows, and involved substituent is referring to table 5-19 in formula, and specific representation compound is referred to respectively Table,
Table 5：As A=H, R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=R7During=H, R1、R2、R3、R4、R5Substituent is shown in Table 5, according to The 1-180 of secondary corresponding table 5, representation compound numbering is 5-1-5-180.
Table 5
Numbering R1 R2 R3 R4 R5
1 H H H H H
2 H F H H H
3 H H F H H
4 H H H F H
5 H Cl H H H
6 H H Cl H H
7 H H H Cl H
8 H Br H H H
9 H H Br H H
10 H H H Br H
11 H I H H H
12 H H I H H
13 H H H I H
14 H CH3 H H H
15 H H CH3 H H
16 H H H CH3 H
17 H OCH3 H H H
18 H H OCH3 H H
19 H H H OCH3 H
20 H CF3 H H H
21 H H CF3 H H
22 H H H CF3 H
23 H OCF3 H H H
24 H H OCF3 H H
25 H H H OCF3 H
26 H NO2 H H H
27 H H NO2 H H
28 H H H NO2 H
29 H CN H H H
30 H H CN H H
31 H H H CN H
32 H CH(CH3)2 H H H
33 H H CH(CH3)2 H H
34 H H H CH(CH3)2 H
35 H H H t-Bu H
36 H SCH3 H H H
37 H H SCH3 H H
38 H H H SCH3 H
39 H SCF3 H H H
40 H H SCF3 H H
41 H H H SCF3 H
42 H COCH3 H H H
43 H H COCH3 H H
44 H H H COCH3 H
45 H SOCH3 H H H
46 H H SOCH3 H H
47 H H H SOCH3 H
48 H SO2CH3 H H H
49 H H SO2CH3 H H
50 H H H SO2CH3 H
51 H OCHF2 H H H
52 H H OCHF2 H H
53 H H H OCHF2 H
54 H CO2CH3 H H H
55 H H CO2CH3 H H
56 H H H CO2CH3 H
57 H N(CH3)2 H H H
58 H H N(CH3)2 H H
59 H H H N(CH3)2 H
60 H N(C2H5)2 H H H
61 H H N(C2H5)2 H H
62 H H H N(C2H5)2 H
63 H NHCOCH3 H H H
64 H H NHCOCH3 H H
65 H H H NHCOCH3 H
66 H NHSO2CH3 H H H
67 H H NHSO2CH3 H H
68 H H H NHSO2CH3 H
69 H OCH2CH=CH2 H H H
70 H H OCH2CH=CH2 H H
71 H H H OCH2CH=CH2 H
72 H OCH2C≡CH H H H
73 H H OCH2C≡CH H H
74 H H H OCH2C≡CH H
75 H F F H H
76 H F H F H
77 F F H H H
78 H F H H F
79 H H F F H
80 F H F H H
81 H Cl Cl H H
82 H Cl H Cl H
83 Cl Cl H H H
84 H Cl H H Cl
85 H H Cl Cl H
86 Cl H Cl H H
87 H NO2 H NO2 H
88 NO2 NO2 H H H
89 H NO2 H H NO2
90 NO2 H NO2 H H
91 H CN H CN H
92 CN CN H H H
93 H CN H H CN
94 CN H CN H H
95 H CH3 CH3 H H
96 H CH3 H CH3 H
97 CH3 CH3 H H H
98 H CH3 H H CH3
99 H H CH3 CH3 H
100 CH3 H CH3 H H
101 H CF3 H CF3 H
102 CF3 CF3 H H H
103 H CF3 H H CF3
104 CF3 H CF3 H H
105 H OCF3 H OCF3 H
106 OCF3 OCF3 H H H
107 H OCF3 H H OCF3
108 OCF3 H OCF3 H H
109 H CH3 Cl H H
110 H CH3 H Cl H
111 H H Cl CH3 H
112 H Cl H CH3 H
113 Cl CH3 H H H
114 H CH3 H H Cl
115 H Br CH3 H H
116 H H CH3 Cl H
117 H CH3 NO2 H H
118 H CH3 H NO2 H
119 H CH3 H OCH3 H
120 NO2 CH3 H H H
121 H Cl H CF3 H
122 CF3 Cl H H H
123 H Cl H NO2 H
124 NO2 Cl H H H
125 H CF3 H Br H
126 H CF3 H NO2 H
127 H H CF3 NO2 H
128 H H CF3 Cl H
129 H CF3 H CN H
130 H Cl H CN H
131 H NO2 H CN H
132 H NO2 H CH3 H
133 H NO2 H CF3 H
134 H NO2 H Cl H
135 Cl NO2 H H H
136 H H NO2 CH3 H
137 H H NO2 Cl H
138 H CN F H H
139 H CN H NO2 H
140 H CN H Cl H
141 CH3 CN H H H
142 H Cl Cl Cl H
143 Cl Cl Cl H H
144 Cl Cl H Cl H
145 H Cl H Cl Cl
146 Cl H Cl Cl H
147 H CH3 H CH3 CH3
148 H OCH3 H OCH3 OCH3
149 H Cl Cl Br H
150 H F H F Cl
151 H CH3 H Br Br
152 H CF3 H Cl Cl
153 H CF3 H Br Br
154 H F H Cl Br
155 H Cl H NO2 Cl
156 H Br H NO2 Br
157 H Cl H CN Cl
158 H Cl H CF3 Cl
159 H Br H CF3 Br
160 H Cl CH3 H Cl
161 H Cl H CONH2 Cl
162 H Cl H CO2CH3 Cl
163 H Cl H NHCOCH3 Cl
164 H Cl H OCF3 Cl
165 H Br H F Br
166 H Br H CH3 Br
167 H Cl H COCH3 Cl
168 Cl Cl H NO2 H
169 H F H F Cl
170 H Cl H CF3 Br
171 H CH3 H NO2 Cl
172 H CH3 H NO2 Br
173 H CH3 H Cl NO2
174 H CH3 H Br NO2
175 H NO2 H CF3 Cl
176 H NO2 H CF3 Br
177 H F H Br Br
178 H CN H Cl Cl
179 H CN H Br Br
180 F F F H F
Table 6：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 5 one Cause, be corresponding in turn to the 1-180 of table 5, representation compound numbering is 6-1-6-180.
Table 7：As A=H, R8'=CH3, R9=C2H5, R10=H, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 5 one Cause, be corresponding in turn to the 1-180 of table 5, representation compound numbering is 7-1-7-180.
Table 8：A=H, R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 5 one Cause, be corresponding in turn to the 1-180 of table 5, representation compound numbering is 8-1-8-180.
Table 9：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 5 Unanimously, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 9-1-9-180.
Table 10：As A=H, R8'=CH3, R9=C2H5, R10=H, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 5 Unanimously, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 10-1-10-180.
Table 11：A=H, R8'=CH3, R9=CH3, R10=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 5 Unanimously, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 11-1-11-180.
Table 12：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 12-1-12-180.
Table 13：As A=H, R8'=CH3, R9=C2H5, R10=H, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 13-1-13-180.
Table 14：As A=H, R8'=CH3, R9=CH3, R10=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5 It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 14-1-14-180.
Table 15：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5 It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 15-1-15-180.
Table 16：As A=H, R8'=CH3, R9=C2H5, R10=H, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5 It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 16-1-16-180.
Table 17：As A=H, R8'=CH3, R9=CH3, R10=Cl, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 17-1-17-180.
Table 18：As A=H, R8'=CH3, R9=C2H5, R10=Cl, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 18-1-18-180.
Table 19：As A=H, R8'=CH3, R9=C2H5, R10=H, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 19-1-19-180.
Formula I-B chemical formulas are as follows, and involved substituent is referring to table 20-34 in formula, and specific representation compound is referred to Each table,
Table 20：As A=H, R8'=CH3, R9=CF3, R10'=H, Ra=Rb=R7During=H, R1、R2、R3、R4、R5Substituent, is shown in Table 5, The 1-180 of table 5 is corresponding in turn to, representation compound numbering is 20-1-20-180.
Table 21：As A=H, R8'=CH3, R9=CHF2, R10'=H, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 5 one Cause, be corresponding in turn to the 1-180 of table 5, representation compound numbering is 21-1-21-180.
Table 22：As A=H, R8'=CH3, R9=CH3, R10'=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 5 Unanimously, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 22-1-22-180.
Table 23：As A=H, R8'=CH3, R9=CF3, R10'=H, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 5 Unanimously, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 23-1-23-180.
Table 24：As A=H, R8'=CH3, R9=CHF2, R10'=H, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 24-1-24-180.
Table 25：As A=H, R8'=CH3, R9=CH3, R10'=CH3, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 25-1-25-180.
Table 26：As A=H, R8'=CH3, R9=CF3, R10'=H, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 26-1-26-180.
Table 27：As A=H, R8'=CH3, R9=CHF2, R10'=H, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 27-1-27-180.
Table 28：As A=H, R8'=CH3, R9=CH3, R10'=CH3, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 28-1-28-180.
Table 29：As A=H, R8'=CH3, R9=CF3, R10'=H, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5 It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 29-1-29-180.
Table 30：As A=H, R8'=CH3, R9=CHF2, R10'=H, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5 It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 30-1-30-180.
Table 31：As A=H, R8'=CH3, R9=CH3, R10'=CH3, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、 R5It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 31-1-31-180.
Table 32：As A=H, R8'=CH3, R9=CF3, R10'=H, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 32-1-32-180.
Table 33：As A=H, R8'=CH3, R9=CHF2, R10'=H, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 33-1-33-180.
Table 34：As A=H, R8'=CH3, R9=CH3, R10'=CH3, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 34-1-34-180.
Formula I-C chemical formulas are as follows, and involved substituent is referring to table 35-59 in formula, and specific representation compound is referred to Each table,
Table 35：As A=H, R7=H, R1=R2=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R1435 are shown in Table, according to The 1-32 of secondary corresponding table 35, representation compound numbering is 35-1-35-32.
Table 35
Numbering Y R9 R10 R11 R12 R13 R14
1 N OCH2CF3 H Cl H H H
2 N OCH2CF3 H Br H H H
3 N OCHF2 H Cl H H H
4 N OCHF2 H Br H H H
5 N CF3 H Cl H H H
6 N CF3 H Br H H H
7 N Cl H Cl H H H
8 N Cl H Br H H H
9 N Cl H Cl H CF3 H
10 N Cl H Cl H CN H
11 N Cl H Cl H Cl H
12 N Cl H Cl H Cl Cl
13 N Br H Cl H H H
14 N Br H Br H H H
15 N Br H Cl H CF3 H
16 N Br H Cl H CN H
17 N Br H Cl H Cl H
18 N Br H Cl H Cl Cl
19 N CN H Cl H H H
20 N CN H Br H H H
21 N OCH3 H Cl H H H
22 N OCH3 H Br H H H
23 N CH3 H Cl H H H
24 N CH3 H Br H H H
25 N C2H5 H Cl H H H
26 N C2H5 H Br H H H
27 N OCH2CH=CH2 H Cl H H H
28 N Propynyloxy base H Cl H H H
29 N OCH2CN H Cl H H H
30 C-Cl CN CF3 Cl H CF3 H
31 C-Cl CN SCF3 Cl H CF3 H
32 CH CH3 H Cl H H H
Table 36：As A=H, R7=H, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 36-1-36-32.
Table 37：As A=H, R7=H, R4=CH3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 37-1-37-32.
Table 38：As A=H, R7=H, R4=NO2, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 38-1-38-32.
Table 39：As A=H, R7=H, R4=F, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 1 Cause, be corresponding in turn to the 1-32 of table 35, representation compound numbering is 39-1-39-32.
Table 40：As A=H, R7=H, R4=CF3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 40-1-40-32.
Table 41：As A=H, R7=H, R4=OCH3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 41-1-41-32.
Table 42：As A=H, R7=H, R4=t-Bu, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 42-1-42-32.
Table 43：As A=H, R7=H, R4=CN, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 43-1-43-32.
Table 44：As A=H, R7=H, R2=Cl, R1=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 44-1-44-32.
Table 45：As A=H, R7=H, R1=Cl, R2=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 45-1-45-32.
Table 46：As A=H, R7=H, R1=CF3, R2=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 46-1-46-32.
Table 47：As A=H, R7=H, R2=CH3, R4=Cl, R1=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With Table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 47-1-47-32.
Table 48：As A=H, R7=H, R2=R4=Cl, R1=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 48-1-48-32.
Table 49：As A=H, R7=H, R3=R5=Cl, R1=R2=R4During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 49-1-49-32.
Table 50：As A=H, R7=H, R1=R4=Cl, R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 50-1-50-32.
Table 51：As A=H, R7=H, R1=R3=Cl, R2=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 51-1-51-32.
Table 52：As A=H, R7=H, R2=R5=Cl, R1=R3=R4During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 52-1-52-32.
Table 53：As A=H, R7=H, R2=Cl, R4=CF3, R1=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With Table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 53-1-53-32.
Table 54：As A=H, R7=H, R2=Cl, R4=NO2,R1=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With Table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 54-1-54-32.
Table 55：As A=H, R7=H, R1=CF3,R2=Cl, R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With Table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 55-1-55-32.
Table 56：As A=H, R7=H, R2=R5=Cl, R4=CF3, R1=R3During=H, substituent Y, R9、R10、R11、R12、R13、R14With Table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 56-1-56-32.
Table 57：As A=H, R7=Cl, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 57-1-57-32.
Table 58：As A=CH3, R7=Cl, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 58-1-58-32.
Table 59：As A=CH2Ph, R7=Cl, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With Table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 59-1-59-32.
Formula I-D chemical formulas are as follows, and involved substituent is referring to table 60-94 in formula, and specific representation compound is referred to Each table,
Table 60：As A=H, Ra=Rb=R7=H, R1=R2=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 60-1-60-32.
Table 61：As A=H, Ra=Rb=R7=H, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 61-1-61-32.
Table 62：As A=H, Ra=Rb=R7=H, R4=CH3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 62-1-62-32.
Table 63：As A=H, Ra=Rb=R7=H, R4=NO2, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 63-1-63-32.
Table 64：As A=H, Ra=Rb=R7=H, R4=F, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14With Table 35 is consistent, is corresponding in turn to the 1-32 of table 35, representation compound numbering is 64-1-64-32.
Table 65：As A=H, Ra=Rb=R7=H, R4=CF3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 65-1-65-32.
Table 66：As A=H, Ra=Rb=R7=H, R4=OCH3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 66-1-66-32.
Table 67：As A=H, Ra=Rb=R7=H, R4=t-Bu, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 67-1-67-32.
Table 68：As A=H, Ra=Rb=R7=H, R4=CN, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 68-1-68-32.
Table 69：As A=H, Ra=Rb=R7=H, R2=Cl, R1=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 69-1-69-32.
Table 70：As A=H, Ra=Rb=R7=H, R1=Cl, R2=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 70-1-70-32.
Table 71：As A=H, Ra=Rb=R7=H, R1=CF3, R2=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 71-1-71-32.
Table 72：As A=H, Ra=Rb=R7=H, R2=R4=Cl, R1=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 Consistent with table 35, the 1-32 representation compounds numbering for being corresponding in turn to table 35 is 72-1-72-32,.
Table 73：As A=H, R7=H, R3=R5=Cl, R1=R2=R4During=H, substituent Y, R9、R10、R11、R12、R13、R14With table 35 Unanimously, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 73-1-73-32.
Table 74：As A=H, Ra=Rb=R7=H, R1=R4=Cl, R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 74-1-74-32.
Table 75：As A=H, Ra=Rb=R7=H, R1=R3=Cl, R2=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 75-1-75-32.
Table 76：As A=H, Ra=Rb=R7=H, R2=R5=Cl, R1=R3=R4During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 76-1-76-32.
Table 77：As A=H, Ra=Rb=R7=H, R2=Cl, R4=CF3, R1=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 77-1-77-32.
Table 78：As A=H, Ra=Rb=R7=H, R2=Cl, R4=NO2,R1=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 78-1-78-32.
Table 79：As A=H, Ra=Rb=R7=H, R2=CH3, R4=Cl, R1=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 79-1-79-32.
Table 80：As A=H, Ra=Rb=R7=H, R1=CF3,R2=Cl, R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 80-1-80-32.
Table 81：As A=H, Ra=Rb=R7=H, R2=R5=Cl, R4=CF3, R1=R3During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 81-1-81-32.
Table 82：As A=H, Ra=Rb=H, R7=Cl, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 82-1-82-32.
Table 83：As A=CH3, Ra=Rb=H, R7=Cl, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、 R13、R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 83-1-83-32.
Table 84：As A=CH2Ph, Ra=Rb=H, R7=Cl, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、 R13、R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 84-1-84-32.
Table 85：As A=H, Ra=CH3, Rb=R7=H, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 85-1-85-32.
Table 86：As A=H, Ra=CH3, Rb=R7=H, R1=R2=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 86-1-86-32.
Table 87：As A=H, Ra=CH3, Rb=R7=H, R4=CF3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、 R13、R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 87-1-87-32.
Table 88：As A=H, Ra=CH3, Rb=R7=H, R4=CH3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、 R13、R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 88-1-88-32.
Table 89：As A=H, Ra=Rb=CH3, R7=H, R4=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 89-1-89-32.
Table 90：As A=H, Ra=Rb=CH3, R7=H, R1=R2=R3=R4=R5During=H, substituent Y, R9、R10、R11、R12、R13、R14 It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 90-1-90-32.
Table 91：As A=H, Ra=Rb=CH3, R7=H, R4=CF3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、 R13、R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 91-1-91-32.
Table 92：As A=H, Ra=Rb=CH3, R7=H, R4=CH3, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、 R13、R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 92-1-92-32.
Table 93：As A=H, Ra=CH3, Rb=H, R4=R7=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 93-1-93-32.
Table 94：As A=H, Ra=Rb=CH3, R4=R7=Cl, R1=R2=R3=R5During=H, substituent Y, R9、R10、R11、R12、R13、 R14It is consistent with table 35, the 1-32 of table 35 is corresponding in turn to, representation compound numbering is 94-1-94-32.
Formula II-A chemical formulas are as follows, and involved substituent is referring to table 95-102 in formula, and specific representation compound is detailed See each table,
Table 95：As A=H, R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=R7During=H, R1、R2、R3、R4、R5Substituent, is shown in Table 5, The 1-180 of table 5 is corresponding in turn to, representation compound numbering is 95-1-95-180.
Table 96：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 5 one Cause, be corresponding in turn to the 1-180 of table 5, representation compound numbering is 96-1-96-180.
Table 97：A=H, R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 5 one Cause, be corresponding in turn to the 1-180 of table 5, representation compound numbering is 97-1-97-180.
Table 98：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 98-1-98-180.
Table 99：A=H, R8'=CH3, R9=CH3, R10=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 5 Unanimously, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 99-1-99-180.
Table 100：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 100-1-100-180.
Table 101：As A=H, R8'=CH3, R9=CH3, R10=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5 It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 101-1-101-180.
Table 102：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、 R5It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 102-1-102-180.
Formula Ш-A chemical formulas are as follows, and involved substituent is referring to table 103-116 in formula, and specific representation compound is detailed See each table,
Table 103：As A=H, R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=R7During=H, R1、R2、R3、R4、R5Substituent, is shown in Table 5, The 1-180 of table 5 is corresponding in turn to, representation compound numbering is 103-1-103-180.
Table 104：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 5 Unanimously, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 104-1-104-180.
Table 105：A=H, R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 5 Unanimously, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 105-1-105-180.
Table 106：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 106-1-106-180.
Table 107：A=H, R8'=CH3, R9=CH3, R10=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 5 Unanimously, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 107-1-107-180.
Table 108：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With Table 5 is consistent, is corresponding in turn to the 1-180 of table 5, representation compound numbering is 108-1-108-180.
Table 109：As A=H, R8'=CH3, R9=CH3, R10=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5 It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 109-1-109-180.
Table 110：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、 R5It is consistent with table 5, the 1-180 of table 5 is corresponding in turn to, representation compound numbering is 110-1-110-180.
Table 111：As A=H, R8'=CH3, R9=C2H5, R10=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、 R5It is consistent with table 111, the 1-140 of table 111 is corresponding in turn to, representation compound numbering is 111-1-111-140.
Table 111
Table 112：In formula I-A, work as R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=R7=R1=R2=R3=R5During=H, R4=Cl, takes 111 are shown in Table for base A, the 1-140 of table 111 is corresponding in turn to, representation compound numbering is 112-1-112-180.
Table 113：In formula I-A, work as R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=R7=R1=R2=R3=R5=H, R4During=H, substitution Base A is consistent with table 111, is corresponding in turn to the 1-140 of table 111, representation compound numbering is 113-1-113-180.
Table 114：In formula I-A, work as R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=R7=R1=R2=R3=R5=H, R4=CF3When, take It is consistent for base A and table 111, the 1-140 of table 111 is corresponding in turn to, representation compound numbering is 114-1-114-180.
Table 115：In formula I-B, work as R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=R7=R1=R2=R3=R5=H, R4=CH3When, take It is consistent for base A and table 111, the 1-140 of table 111 is corresponding in turn to, representation compound numbering is 115-1-115-180.
Table 116：In formula I-B, work as R8'=CH3, R9=CH3, R10=Cl, Ra=Rb=R7=R1=R2=R3=R5=H, R4=OCH3When, Substituent A is consistent with table 111, is corresponding in turn to the 1-140 of table 111, representation compound numbering is 116-1-116-180.
The preparation method of compound of Formula I of the present invention is as follows, and the preparation of formula II and III compound is referred to lead to Prepared by compound of formula I method, except that initiation material is replaced into 6- chlorine apellagrins（M-1）It is changed to substitution 2- chloroisonicotinic acids With substitution 2- chlorine apellagrins.
Compound of Formula I of the present invention is prepared in accordance with the following methods, and reaction equation is as follows, and each group is unless otherwise indicated fixed in formula It is adopted the same：
Reaction obtains compound of Formula I to intermediate H and L in the basic conditions in suitable solvent.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium acid carbonate, triethylamine, pyridine, Sodium methoxide, caustic alcohol, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
Reaction in suitable solvent carry out, the optional tetrahydrofuran freely of suitable solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile, Toluene, dimethylbenzene, benzene, N,N-dimethylformamide, 1-METHYLPYRROLIDONE, dimethyl sulfoxide, acetone or butanone etc..
Reaction temperature can be in room temperature between solvent boiling point temperature, usually 20-100 DEG C.
Reaction time is 30 minutes to 20 hours, usual 1-10 hours.
Intermediate L is commercially available or is prepared by known method, and specific prepare can refer to document Annalen der Chemie Justus Liebig ' s, 536,97（1938）、Bull.Soc.Chim.France,293(1966)、US4950668、 It is prepared by the method for the descriptions such as JP2292263, JP2053776, JP4069361 or JP4069379.
Intermediate H defines difference according to A, B, is divided into following three kinds of situations and prepares：
The first situation：
As A=H,
1）The carbon nitrogen singly-bound that B=amide nitrogen atoms are joined directly together with pyridine ring 3,4 or 5 carbon atoms, referring to patent It is prepared by the method described in WO9924404.
2）B=-CH2CRaRb- when, referring to the side described in patent WO9404527, US20110054173 or WO2011022 It is prepared by method.Or be prepared as follows：
In formula, U is leaving group, is halogen or hydroxyl etc..
Intermediate H-1 and H-2 is in the presence of suitable alkali, at suitable temperature, is reacted 30 minutes in suitable solvent It is usual 1-10 hours to 20 hours, intermediate H-3 is made；H-4 is made through red aluminium reducing in H-3, and this step operation method is referring to special Sharp EP1840128；H-5 is made with thionyl chloride reaction in H-4, and this is normal experiment method；H-5 reacts with Cymag, and H- is made 6, this step operation method is referring to patent WO2007045989, WO2009115257, according to Journal of Organic Chemistry,71(21),8023-8027;2006th, Synthesis, (24), 4242-4250,2010, Heterocycles, 56 (1-2), 443-455,2002 or ARKIVOC (Gainesville, FL, United States) [online computer File], H-7 is made by H-6 in (10), 40-51, the method described in 2002；Finally, H-7 appropriate catalyst as and ammoniacal liquor In the presence of hydrogenated reduction obtain intermediate H, specific prepare is referred to document J.Am.Chem.Soc, 70,3788 (1948); 82,681(1960);82,2386(1960)；Can.J.Chem, 49,2990（1971）；J.Org.Chem,37,335(1972)； Organic Syntheses, Coll.Vol.3, p.229, p.720 (1955), Vol.23, p.71 (1943) or Vol.27, p.18 (1947) method described in is carried out.Suitable catalyst may be selected from Raney's nickel, palladium carbon or platinum oxide etc..
Intermediate source is as follows：Intermediate H-1 and H-2 is commercially available, or is conventionally prepared.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium acid carbonate, triethylamine, pyridine, Sodium methoxide, caustic alcohol, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
Reaction in suitable solvent carry out, the optional tetrahydrofuran freely of suitable solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile, Toluene, dimethylbenzene, benzene, N,N-dimethylformamide, 1-METHYLPYRROLIDONE, dimethyl sulfoxide, acetone or butanone etc..
Reaction temperature can be in room temperature between solvent boiling point temperature, usually 20-100 DEG C.
Reaction time is 30 minutes to 20 hours, usual 1-10 hours.
3)B=-CH2CRaRbCRaRb- when, preparation method is as follows：
H-8 is prepared by H-7 and refers to Synthesis, (9), 727-9;1983 or Tetrahedron Letters, 39 (51), 9455-9456;Method described in 1998 is carried out；The same B=- CH of H-13 methods is prepared by H-82CRaRb- when corresponding steps.
Second of situation：
As A ≠ H, it is made by A=H intermediate for raw material, concrete operations are referring to the side described in WO2004093800A Method is carried out.
Formula I, II or Ш compound show excellent activity to a variety of germs in agricultural or other field, to insect Evil mite also shows that preferable activity.Therefore, technical scheme also include formula I, II or Ш compound agricultural or It is used as the purposes for preparing bactericide, insecticidal/acaricidal agent in other field.
The example of disease referenced below is only used for illustrating the present invention, but never limits the present invention.
Formula I, II or Ш compound can be used for preventing and treating following disease：Oomycetes diseases, such as downy mildew（Cucumber downy mildew, Oilseed rape downy mildew, downy mildew, beet downy mildew, downy mildew of sugarcane, tobacco downy mildew, pea downy mildew, sponge gourd downy mildew, Wax gourd downy mildew, 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 are continuous Maize ear rot）, epidemic disease（Broad bean epidemic disease, Cucumber Blight, pumpkin epidemic disease, wax gourd epidemic disease, watermelon epidemic disease, muskmelon blight, capsicum epidemic disease, fragrant-flowered garlic Dish epidemic disease, garlic epidemic disease, Cotton blight）, late blight（The late blight of potato, tomato late blight）Deng；Fungi Imperfecti disease, it is such as withered Disease（Sweet potato droop, cotton wilt, sesame droop, castor-oil plant droop, tomato wilt, Kidney bean droop, cucumber wither Disease, sponge gourd droop, pumpkin droop, wax gourd droop, watermelon blight, Muskmelon Fusarium wilt, capsicum wilt, broad bean are withered Disease, rape droop, soybean Fusariuming disease）, root rot（Fusarium solani, eggplant root rot, Kidney bean root rot, cucumber root rot, Balsam pear root rot, cotton black root rot, root rot of Vicia faba）, damping-off（Cotton seedling blight, sesame damping-off, capsicum damping-off, Huang Melon damping-off, Chinese cabbage damping-off）, anthracnose（Anthracnose of sorghum, cotton anthracnose, bluish dogbane anthracnose, jute anthracnose, flax Anthracnose, anthracnose of tobacco, mulberry anthracnose, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, balsam pear charcoal Subcutaneous ulcer disease, cucurbita pepo anthracnose, wax gourd anthracnose, watermelon anthrax, muskmelon anthracnose, lichee anthracnose）, verticillium wilt（Cotton yellow Wither disease, sunflower verticillium wilt, tomato verticillium wilt, capsicum verticillium wilt, eggplant verticillium wilt）, scab（Cucurbita pepo scab, wax gourd Scab, muskmelon scab）, gray mold（Cotton boll gray mold, bluish dogbane gray mold, graw mold of tomato, Botrytis cinerea, Kidney bean ash Mildew, celery gray mold, spinach gray mold, Kiwi berry gray mold）, brown spot（Cotton brown spot, jute brown spot, beet are brown Pinta, the cercospora brown spot of peanut, capsicum brown spot, wax gourd brown spot, soybean brown spot, septorial brown spot of sunflower, pea brown spot, broad bean Brown spot）, black spot（Flax vacation black spot, alternaria stem rot of colza, sesame black spot, sunflower black spot, castor-oil plant black spot, kind Eggplant black spot, capsicum black spot, eggplant black spot, Kidney bean black spot, cucumber black spot, celery black spot, carrot black rot, Black rot of carrot, 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（Early blight of tomato, capsicum early blight, eggplant early blight, target, early blight of celery）, ring spot（Soybean Ring spot, sesame ring spot, Kidney bean ring spot）, leaf blight（Sesame leaf blight, sunflower leaf rot, watermelon leaf blight, muskmelon Leaf blight）, base rot disease（Tomato base rot disease, Kidney bean base rot disease）, and other（Helminthosporium carbonum, bluish dogbane waist folding disease, rice blast Disease, the black sheath disease of chestnut, sugarcane eye spot, cotton boll aspergillosis, peanut crown rot, soybean stem wilt, soybean diplostomiasis, the big spot of muskmelon The red leaf spot of disease, Peanut Web Blotch Disease, tea, pepper white star disease, wax gourd leaf spot, celery black rot, spinach heartrot, bluish dogbane leaf mold Disease, bluish dogbane spot disease, jute stem blight, purple spot of soybean, Alternaria sesami, castor-oil plant graywall, dark brown leaf spot, eggplant are brown Color circle star disease, Kidney bean red spot disease, balsam pear Leucoplakia, watermelon spot disease, jute withered rotten disease, sunflower root stem rot, Kidney bean charcoal are rotten Disease, soybean target spot disease, eggplant rod spore leaf spot, Leaf Spot Caused by Corynespora cassiicola on Cucumber, leaf muld of tomato, eggplant leaf mold, broad bean red spot etc.） Deng；Load fungus diseases, such as rust（It is stripe rust of wheat, the stem rust of wheat, wheat leaf rust, Peanut Rust, rust of sunflower, sweet Sugarcane rust, leek rust, rust of onion, chestnut rust, soybean rust）, smut（Maize head smut, corn smut, sorghum silk Smut, sorghum loose smut, covered kernel smut of kaoliang, high beam column smut, chestnut kernel smut, smut of sugarcane, Bean rust disease） And other（Such as wheat sharp eyespot, rice sheath blight disease）Deng；Sac fungus disease, such as powdery mildew（Wheat powdery mildew, rape white powder Disease, sesame powdery mildew, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, powdery mildew of pea, sponge gourd powdery mildew, pumpkin are white Powder disease, Pumpkin powdery mildew, wax gourd powdery mildew, melon powdery mildew, uncinula necator, broad bean powdery mildew）, sclerotiniose（Flax bacterium Core disease, sclerotinia sclerotiorum, soybean sclerotinia crown rot, peanut sclerotiniose, tobacco sclerotiniose, capsicum sclerotiniose, eggplant sclerotiniose, Kidney bean bacterium Core disease, pea sclerotiniose, cucumber timberrot, balsam pear sclerotiniose, wax gourd sclerotinia, watermelon sclerotiniose, celery sclerotiniose）, black star Disease（Scab of apple, pear scab）Deng.Especially, to corn rust, rice blast, gray mold of cucumber and cucumber downy mildew Disease, still has good prevention effect at lower doses.
Formula I, II or Ш compound can be used for preventing and treating following insect：Coleoptera (Coleoptera) (beetle)：Bean weevil belongs to Kind of (Acanthoscelides spp.) (curculionid), acanthoscelides obtectus (Acanthoscelides obtectus) (common pea weevil), Emerald ash borer (Agrilus planipennis) (emerald ash borer, Agrilus planipennis), acupuncture needle Eimeria kind (Agriotes spp.) (acupuncture needle Worm), anoplophora glabripennis (Anoplophora glabripennis) (Asia psacotheahilaris), Anthonomusgrandis category kind an of (Anthonomus Spp.) (Culculionidae), Mexico's Anthonomusgrandis (Anthonomus grandis) (bollworm), cocoon honeybee category kind (Aphidius Spp.), weevil category kind (Apion spp.) (curculionid), sugarcane cockchafer category kind (Apogonia spp.) (grub), black suede cockchafer (Atacnius sprctulus) (smaller velvety chafer), Atomaria linearis (Atomaria linearis) (small beet beetle (pygmy mangold beetle), cucumber beetle category kind (Aulacophore spp.), beet are as (Bothynoderes Punctiventris) (beet root curculionid), bean weevil category kind (Bruchus spp.) (curculionid), pea weevil (Bruchus Pisorum) (pea weevil), Cacoesia category kind (Cacoesia spp.), Callosobruchus maculatus (Callosobruchus Maculatus) (southern cowpea curculionid), pineapple bug (Carpophilus hemipteras) (dried-frait beetle), beet tortoise First (Cassida vittata), day Bos kind (Ccrostcrna spp.), Ccrotoma category kind (Ccrotoma spp.) (gold Trichomonad (chrysomcids)), beans chrysomelid (Cerotoma trifur cata) (the chrysomelid worm of beans), ceutorhynchus kind (Ceutorhynchus spp.) (curculionid), Chinese cabbage seed tortoise are as (Ceutorhynchus assimilis) (Chinese cabbage weevil (cabbage seedpod weevil)), turnip tortoise is as (Ceutorhynchus napi) (cabbage curculionid (cabbage Curculio)), phyllotreta kind (Chaetocnema spp.)（Chrysomonad), Colaspis category kind of (a Colaspis spp.) (soil Beetle), Conoderus scalaris, Conoderus stigmosus, Lee is as (Conotrachelus nenuphar) (plum Bore weevil), Cotinus nitidis (Green june beetle (Green June beetle)), asparagus scotellaris (Crioceris Asparagi) (asparagus beetle), rusty grain beetle (Cryptolestes ferrugincus) (rust paddy beetle (rusty Grainbeetle)), Cryptolestes pusillus (Cryptolestes pusillus) (flat ostomatid), Cryptolestes turcicus Grouville (Cryptolestes turcicus) (Turkey paddy beetle (Turkish grain beetle)), Ctenicera category kind (Ctenicera spp.) (nematode), Curculio kind (Curculio spp.) (curculionid), round end rhinoceros cockchafer category kind (Cyclocephala spp.) (grub), close withe are as (Cylindrocpturus adspersus) (sunflower grass curculionid (sunflower stem weevil)), mango leaf-cutting is as (Deporaus marginatus) (mango leaf-cutting curculionid (mango Leaf-cutting weevil)), lader beetle stupid (Dermestes lardarius) (lader beetle is stupid), white abdomen skin it is stupid (Dermestes maculates) (white abdomen skin is stupid), chrysomelid category kind (Diabrotica spp.) (chrysomelid), mexican bean ladybird (Epilachna varivcstis) (Mexico beans beetle), moth stem weevil (raustinus cubae), pale neck as (Hylobius pales) (pales weevil (pales weevil)), Phytonomus kind (Hypera spp.) (curculionid), alfalfa leaf As (Hypera postica) (alfalfa weevil), Hyperdoes category kind (Hyperdoes spp.) (Argentinian stem weevils (Hyperodes weevil)), the small stupid category kind of coffee berry small stupid (Hypothenemus hampei) (coffee berry beetle), tooth (Ips spp.) (spine shin is small stupid (engravers)), lasioderma serricorne (Lasioderma serricorne) (cigarette beetle), Ma Ling Potato beetle (Leptinotarsa decemlineata) (Colorado potato beetle), Liogenys fuscus, The stupid category kind of Liogenys suturalis, rice water weevil (Lissorhoptrus oryzophilus) (rice water weevil), powder (Lyctus spp.) (the wooden stupid stupid beetle of moth/powder (powder post beetles)), Maecolaspis joliveti, Megascelis category kind (Megascelis spp.), corn click beetle (Melanotus communis), nitidulid category kind (Meligethes spp.), rape nitidulid (Meligethes aeneus) (brevitarsis (blossom beetle)), May Chafer (Melolontha melolontha) (typical European chafer), Oberea brevis, linear cylinder longicorn (Oberea Linearis), coconut palm moth rhinoceros cockchafer (Oryctes rhinoceros) (date palm beetle (date palm beetle)), trade saw paddy Steal (Oryzaephilus mercator) (market saw-toothed grain beetle (merchant grain beetle)), saw-toothed grain beetle (Oryzaephilus surinamensis) (sawtooth paddy beetle (sawtoothcd grain bcctlc)), beak weevil category kind (Otiorhynchus spp.) (curculionid), black angle scotellaris (Oulema melanopus) (cereal leaf beetle (cereal Leafbeetle)), Oulema oryzae (Oulema oryzae), the short beak of rose as category kind of (Pantomorus spp.) (curculionid), Phyllobranchia cockchafer category kind (a Phyllophaga spp.) (May/June chafer) is eaten, Phvllophaga cuyabana, yellow bar are jumped First category kind (Phyllotreta spp.) (chrysomonad), apple tiger are as category kind (Phynchites spp.), Japan popillia flavosellata fairmaire (large space between muscles length is stupid for (Popillia japonica) (Japanese beetle), large space between muscles stupid (Prostephanus truncates) (larger grain borer)), paddy stupid (Rhizopertha dominica) (the small moth of paddy (lesser grain Borer)), root gill cockchafer category kind (Rhizotrogus spp.) (European chafer (Eurpoean chafer)), Rhynchophorus Plant (Rhynchophorus spp.) (curculionid), small stupid category kind (Scolytus spp.) (a wooden stupid moth), Shenophorus category kind (Shenophorus spp.) (grain weevil), pea leaf are as (Sitona lincatus) (pealeaf weevil (pca leaf Weevil)), Sitophilus kind (Sitophilus spp.) (grain weevil first), grain weevil (Sitophilus granaries) (paddy worm (granary weevil)), rice weevil (Sitophilus oryzae) (rice weevil first (rice weevil)), medicinal material ostomatid (Stegobium paniceum) (Stegobium paniceum (drugstore beetle)), Tribolium kind (Tribolium spp.) (face Curculionid), red flour beetle (Tribolium castaneum) (red flour beetle (red flour beetle)), it is miscellaneous plan paddy moisten (Tribolium confusum) (confused flour beetle (confused flour beetle)), the stupid (Trogoderma of piebald skin Variabile) (warehouse skin is stupid (warehouse beetle)) and Zabrus tenebioides.
Dermaptera (Dcrmaptcra)（Earwig).
Neuroptera (Dictyoptera) (cockroach)：Groton bug (Blattella germanica) (Groton bug (German cockroach)), oriental cockroach (Blatta orientalis) (oriental cockoach), Pennsylvania wood Lian (Parcoblatta pennylvanica), American cockroach (Periplaneta americana) (America roach consumptive disease (American Cockroach)), Australian cockroach (Periplaneta australoasiae) (Australian cockroach (Australian Cockroach)), periplaneta brunnea (Pcriplancta brunnca) (periplaneta brunnea (brown cockroach)), smoke Perilpaneta americana （Periplaneta fuliginosa) (Peroplaneta fluligginosa (smokybrown cockroach)), the green blattaria of sugarcane（Pyncoselus Suninamensis) (sugarcane Lian (Surinam cockroach)) and long hair blattaria (Supella longipalpa) (brown band blattaria (brownbanded cockroach))。
Diptera (Diptera) (fly)：Latent fly (the Agromyza of Aedes kind (Aedes spp.) (mosquito), alfalfa Frontella) ((Agromyza spp.) is (latent for (alfalfa dive fly (alfalfa blotch leafminer)), Hippelates kind Leaf fly), by Anastrepha kind (Anastrepha spp.) (drosophila), Caribbean by trypetid (Anastrepha suspensa) (plus Strangle than press trypetid (Caribbean fruit fly)), Anopheles kind (Anopheles spp.) (mosquito), Bactrocera kind (Batrocera spp.) (drosophila), melonfly (Bactrocera cucurbitae) (melon fly), citrus fruit fly (Bactrocera dorsalis) (oriental fruit fly), small bar Anastrepha kind (Ceratitis spp.) (drosophila), the small bar in Mediterranean are real Fly（Ceratitis capitata）（Medfly）, Chrysops kind（Chrysops spp.）（Deer horsefly）, Callitroga's kind (Cochliomyia spp.) (screw worm fly larva), Ying uranotaenia kind（Contarinia spp.）（Ying mosquitos）, Culex kind (Culex Spp.) (mosquito), Ye Ying uranotaenia kinds（Dasineura spp.）（Ying mosquitos）, You Cai Ye Ying mosquitos（Dasineura brassicae）（Volume Xin Cai Ying mosquitos）, Delia kind (Delia spp.), delia platura (Delia platura) (root maggot (seedcorn Maggot)), Drosophila kind（Drosophila spp.）（Vinegar fly）, Fannia kind (Fannia spp.) (housefly), anthomyia canicularis (Fannia canicularis) (Fannia canicularis (little house fly)), anthomyia scalaris (Fannia scalaris) (grey abdomen Latrine fly), big horse botfly (Gasterophilus intestinalis) (horse botfly), Gracillia perseae, Haematobia irritans (Haematobia irritans) (horn fly), Hylemyia kind (Hylemyia spp.) (root maggot (root maggot)), heel fly (Hypoderma lineatum) (common heel fly (common cattle grub)), Liriomyza kind (Liriomyza Spp.) (Liriomyza), wild cabbage liriomyza bryoniae (Liriomyza brassica) (snake Liriomyza (serpentine Leafminer)), sheep hippoboscid (Melophagus ovinus) (sheepked), fly category kind (Musca spp.) (housefly (muscid fly)), face fly (Musca autumnalis) (face fly (face fly)), housefly (Vusca Domestica) (housefly (house fly)), Oestrus ovis (Oestrus ovis) (sheep nose fly (sheep bot fly)), Europe Frit fly (Oscinella frit) (Oscinella frit), beet spring fly (Pegomyia betae) (spinach leaf miner (beet Leafminer)), wheat fly category kind (Phorbia spp.), carrot fly (Psila rosae) (carrot rust fly (carrotrust fly)), cherry fruit fly (Rhagoletis cerasi) (cherry fruit fly (cherry fruit fly)), apple Fruit fly (Rhagoletis pomonella) (apple maggots (apple maggot)), wheat midge (Sitodiplosis Mosellana) (orange wheat flower mosquito (orange wheat blossom midge)), tatukira (stomoxys Calcitruns) (tatukira (stable fly)), gadfly category kind (Tahanus spp.) (horse botfly) and big uranotaenia kind (Tipula Spp.) (daddy-longlegs).
Semiptera (Hemiptera) (stinkbug)：Intend acrosternumhilare (Acrosternum hilare) (acrosternumhilare (green stink Bug)), the pretty fleahopper of america valley cinchbug (Blissus leucopterus) (chinch bug (chinch bug)), potato (Calocoris norvegicus) (potato fleahopper (potato mirid)), cimex hemipterus (Cimex hemipterus) (cimex hemipterus (tropical bed bug)), bedbug (Cimex lectularius) (bedbug (bed hug)), Daghertus The black wing red stinkbug of fasciatus, Dichelops furcatus, cotton (Dysdercus suturellus) (red cotton bug (cotton Stainer)), Edessa meditabunda, Europe Eurygasterspp (Eurygaster maura) (paddy worm (cereal bug)), Euschistus heros, brown smelly stinkbug (Euschistus servus) (brown stinkbug (brown stink bug)), iS-One angle fleahopper (Helopeltis antonii), tea angle fleahopper (Helopeltis theivora) (tea blight plantbug), stinkbug category Plant (Lagynotomus spp.)（Stinkbug), big Leptocorisa spp (Leptocorisa oratorius), different Leptocorisa spp (Leptocorisa Varicornis), Lygus Hahn kind (Lygus spp.) (fleahopper (plant bug)), lygushesperus (Lygus Hesperus) (western tarnished plant bug), the graceful powder stinkbug of the rose of Sharon (Maconellicoccus hirsutus), Neurocolpus longirostris, green rice bug (Nezara viridula) (southern green stink bug), plant Fleahopper category kind of (PhyLocoris spp.) (fleahopper), California plant fleahopper (Phytocoris californicus), Phytocoris relativus, Piezodorus guildingi, four line fleahoppers (Poecilocapsus lineatus) (fourlined plant bug)、Psallus vaccinicola、Pseudacysta perseae、Scaptocoris Castanea and Triatoma kind (Triatoma spp.) (cone nose worm (bloodsuckingconenose bug) of sucking blood/hunt stinkbug (kissing bug))。
Homoptera (Homoptera)（Aphid, a red-spotted lizard, aleyrodid, leafhopper)：Acyrthosiphum pisim (Acrythosiphonpisum)（Pea Aphid (pea aphid)), adelgid kind (Adelges spp.) (adelgids), wild cabbage aleyrodid (Aleurodes Proletella) (cabbage aleyrodid), Aleurodicus dispersus (Aleurodicus disperses), velvet aleyrodid (Aleurothrixus flccosus)（Whitefly in bt cotton (woolly whitefly)), a white wheel armored scale category kind (Aluacaspis Spp.), Amrasca bigutella bigutella, froghopper category kind (Aphrophora spp.) (leafhopper (leafhopper)), California red scale (Aonidiella aurantii) (California red a red-spotted lizard (California red Scale)), Aphis kind (Aphis spp.) (aphid), cotten aphid (Aphis gossypii) (cotton aphid), apple aphid (Aphis pomi) (apple aphid), eggplant are without net aphid (Aulacorthitm solani) (digitalis aphid (foxglove Aphid)), Aleyrodes kind (Bemisia spp.) (aleyrodid), Bemisia argentifolii (Bemisia argentifolii), sweet potato whitefly (Bemisia tabaci) (sweetpotato whitefly), Diuraphis noxia (Brachycolus noxius) (Russian aphid (Russian aphid)), asparagus tubule aphid (Brachycorynclia asparagi) (asparagus aphid (asparagus Aphid)), Brevennia rehi, brevicoryne brassicae (Brevicoryne brassicae) (cabbage aphid), lecanium category kind (Ceroplastes spp.) (a red-spotted lizard), ceroplastes rubens (Ceroplastes rubens) (red wax scale), snow armored scale category kind (Chionaspis spp.) (a red-spotted lizard), Aspidiotus category kind (Chrysomphalus spp.) (a red-spotted lizard), soft wax a red-spotted lizard category kind (Coccus Spp.) (a red-spotted lizard), the pink bad aphid (Dysaphis plantaginea) (rosy apple aphid) of apple, green jassids category kind (Empoasca spp.) (leafhopper), apple aphid (Eriosoma lanigerum) (woolly apple aphid), blow cotton a red-spotted lizard (Icerya purchasi) (cottony cushion scale), mango yellow line leafhopper (Idioscopus nitidulus) (mango leafhopper), small brown rice planthopper (Laodelphax striatellus) (smaller brown planthopper), Lepidosaphes shimer kind (Lepidosaphes spp.), long tube Aphis kind (Macrosiphum spp.), root of Beijing euphorbia Macrosiphus spp (Macrosiphum euphorbiae) (potato aphid (potato aphid)), grain aphid (Macrosiphum Granarium) (Britain's wheat aphid (English grain aphid)), rose aphid (Macrosiphum rosae) (rose Aphid (rose aphid)), four line leafhopper (Macrosteles quadrilineatus) (Aster tataricus leafhopper (aster Leafhopper)), Mahanarva frimbiolata, Acyrthosiphon dirhodum (Metopolophium dirhodum) (rose Wheat aphid (rose grain aphid)), Midis longicornis, black peach aphid (Myzus persicae) (black peach aphid (green Peach aphid)), rice green leafhopper category kind of (Nephotettix spp.) (leafhopper), rice green leafhopper (Nephotettix Cinctipes) (greenery cicada (green leafhopper)), brown paddy plant hopper (Nilaparvata lugens) (brown Planthopper), chaff piece armored scale (Parlatoria pergandii) (chaff scale), ebony armored scale（Parlatoria Ziziphi) (ebonyscale), popcorn wing plant hopper（Peregrinus maidis) (corn delphacid), froghopper category kind (Philaenus spp.) (spittle insects), grape phylloxera (Phylloxera vitifoliae) (grape phylloxera), Physokermes piceae (Physokermes piceae) (spruce bud scale), stern line mealybug category kind (Planococcus spp.) (mealybug), mealybug category kind (Pseudococcus spp.) (mealybug), the clean mealybug of pineapple (Pscudococcus brcvipcs) (pinc apple mcalybug), theatre armored scale (Quadraspidiotus perniciosus) (san jose scale (San Jose Scale)), aphid a red-spotted lizard category kind (Rhapalosiphum spp.) (aphid), corn tree louse (Rhapalosiphum maida) (corn Aphid (corn leaf aphid)), rhopalosiphum padi (Rhapalosiphum padi) (oatbird-cherry aphid), pearl Lecanium category kind (Saissetia spp.) (a red-spotted lizard), olive pearl lecanium (Saissetia oleae) (black a red-spotted lizard), green bugs (Schizaphis graminum) (green bugs (gr eenbug)), grain aphid (Sitobion avenge) (Britain wheat Aphid), white backed planthopper (Sogatella furcifera) (white-backed planthopper), variegation Aphis kind (Therioaphis spp.) (aphid), line lecanium category kind (Toumeyella spp.) (a red-spotted lizard), sound Aphis kind (Toxoptera Spp.) (aphid), white powder Pediculus kind (Trialeurodes spp.) (aleyrodid), Trialeurodes vaporariorum Westwood (Trialeurodes Vaporariorum) (greenhouse whitefly (greenhouse whitefly)), knot wing trialeurodes vaporariorum (Trialeurodes Abutiloneus) (bandedwing whitefly), sharp armored scale category kind (Unaspis spp.) (a red-spotted lizard), the sharp clam (Unaspis of arrow Yanonensis) (arrow a red-spotted lizard (arrowhead scale)) and Zulia entreriana.
Hymenoptera (Hymenoptera) (ant, wasp and honeybee)：It is Myrmecina kind (Acromyrrmex spp.), new Boundary cabbage sawfly (Athalia rosae), leaf ant category kind (Atta spp.) (Ieafcutting ants), black ant category kind (Camponotus spp.) (carpented ant (carpenter ant)), Diprion kind (Diprion spp.) (sawfly (sawfly)), ant category kind (Formica spp.) (ant), Argentine ant (Iridomyrmex humilis) (Argentineant), Monomorium subspecies (Monomorium ssp.), MonomoriumMayr (Monomorium minumum) (little Black ant), kitchen ant (Monomorium pharaonis) (little red ant (Pharaoh ant)), Neodiprion kind (Neodiprion spp.) (sawfly), Pogonomyrmex kind (Pogonomyrmex spp.) (harvester ant), hornet category kind (Polistes spp.) (wasp (paper wasp)), Solenopsis kind (Solenopsis spp.) (fiery ant), odorous antenna (Tapoinoma sessile) (odorous antenna (odorous house ant)), Tetramorium kind (Tetranomorium spp.) (Pavement Ant (pavement ant)), Vespula kind (Vespula spp.) (yellow jacket (yellow jacket)) and carpenter bee Category kind (Xylocopa spp.) (carpenter bee (carpenter bee)).
Isoptera (Isoptera) (termite)：Formosanes category kind (Coptotcrmcs spp.), bent jaw termite (Coptotermes curvignathus), French termite (Coptotermes frenchii), coptotermes formosanus (Coptotermes Formosanus) (Formosan subterranean termite), angle Cryptotermes kind (Cornitermes spp.) (proboscis Termite (nasute termite)), sand Cryptotermes kind (Cryptotermes spp.) (dry-wood termite), different Cryptotermes kind (Heterotermes spp.) (desert Soil termites (desert subterranean termite)), golden yellow different termite ((IIeterotermes aureus), kalotermitid category kind (Kalotermes spp.) (dry-wood termite), principal columns of a hall Cryptotermes kind (Incistitermes spp.) (dry-wood termite), Macrotermes kind (Macrotermes spp.) (cultivation termite (fungus Growing termite)), edge kalotermitid category kind ((Marginitermes spp.) (dry-wood termite), saw a Cryptotermes kind (Microcerotermes spp.) (careless termite (harvester termite)), the small termite (Microtermes of rice wheat Obesi), former angle Cryptotermes kind (Procornitermes spp.), Reticulitermes kind (Reticulitermes spp.) (dwell by soil Termite), Reticulitermes banyulensis, meadow reticulitermes flavipe (Reticulitermes grassei), yellow limb dissipate white Ant (Reticulitermes flavipes) (east Soil termites), U.S. little Huang reticulitermes flavipes (Reticulitermes Hageni), west reticulitermes flavipe (Reticulitermes hesperus) (west Soil termites), Sang Te reticulitermes flavipes (Reticulitermes santonensis), the northern reticulitermes flavipe that dwells (Reticulitermes speratus), U.S. black shin reticulitermes flavipe (Reticulitermes tibialis), U.S. small black reticulitermes flavipe (Reticulitermes virginicus), proboscis reticulitermes flavipe Category kind (Schedorhinotermes spp.) and ancient Cryptotermes kind (Zootermopsis spp.) (rotten wood termite).
Lepidoptera (Lepidoptera) (moth and butterfly)：Achoea janata, Adoxophyessp kind (Adoxophyes Spp.), adoxophyes moth (Adoxophyes orana), tiger category kind of (Agrotis spp.) (cutworm), small cutworm ((Agrotis ipsilon) (black cutworm), cotton leaf ripple noctuid (Alabama argillacea) (cotton leafworm (cotton leafworm))、Amorbia cuneana,Amyelosis transitella(navel orangeworm)、 Anacamptodes defectaria, sliver gelechiid (Anarsia lineatella) (peach twig borer), jute bridge Night high (Anomis sabulijera) (jute looper), Anticarsia (Anticarsia gemmatalis) (velvetbean caterpillar), fruittree leafroller (Archips argyrospila) (fruit tree Leafroller), rose leaf roller (Archips rosana) (rose leaf roller), volume moth category kind (Ar Gyrotaenia spp.) (tortricid moths), tangerine Argyrotaenia spp (Argyrotaenia citrana) (citrus leaf-roller (orange tortrix)), Autographa gamma, Bonagota cranaodcs, rice leaf roller (Borbo Cinnara) (rice leaf folder), cotton leaf lyonetid (Bucculatrix thurberiella) (cotton Leafperforator), thin moth category kind (Caloptilia spp.) (leaf miner), Capua reticulana, peach fruit moth (Carposina niponensis) (peach fruit moth (peach fruit moth)), straw borer spp kind (Chilo spp.), mango Chlumetia transversa (Chlumetia transversa) (mango shoot borer), rose Choristoneura spp (Choristoneura Rosaceana) (oblique banded leaf roller), Noctua kind (Chrysodeixis spp.), cnaphalocrocis are wild Snout moth's larva (Cnaphalocerus medinalis) (meadow leaf roller (grass leafroller)), beans Pier kind (Colias Spp.), lichee litchi (Conpomorpha cramerella), the wooden stupid moth (Cossus cossus) (wooden stupid moth) of fragrance, Crambus Fabricius kind (Crambus spp.) (Sod webworms), Lee's Grapholita spp (Cydia funebrana) (Li Guoe (plum Fruit moth)), oriental fruit months (Cydia molesta) (east heart-eating worm (oriental fruit moth)), pea Eat into pod high (Cydia nignicana) (pea moth), the stupid moth of apple (Cydia pomonella) (codling moth (codling moth)), Darna diducta, Diaphania kind (Diaphania spp.) (stem borer (stem borer)), Snout moth's larva category kind (Diatr aea spp.) (stem borer (stalk bor er)), small sugarcane borer (Diatraea saccharalis) (sugarcane borer), Diatraea grandiosella (Diatraea graniosella) (southwester corn Borer), Earias kind (Earias spp.) (bollworm), earias insulana (Earias insulata) (Egyptian Bollworm), earias fabia (Earias vit.ella) (rough northern bollworm), Ecdytopopha Aurantianum, South America maize seedling phycitid (Elasmopalpus lignosellus) (lesser cornstalk borer), Shallow brown apple moth (Epiphysias postruttana) (light brown apple moth), meal moth category kind (Ephestia spp.) (powder snout moth's larva), meal moth (Ephestia cautella) (almond moth), tobacco powder sp (Ephestia elutella) (tobacco snout moth's larva (tobbaco moth)), Mediterranean flour moth (Ephestia kuehniella) (Mediterranean flour moth), Epimeces category kind (Epimeces spp.), night steinernema (Epinotia Aporema), Erionota thorax (Linne) (Erionota thrax) (banana skipper), ligustrum fine tortricidae (Eupoecilia Ambiguella) (grape berry moth (grape berry moth)), original cutworm (Euxoa auxiliaris) (army Cutworm), Agrotis kind (Feltia spp.) (cutworm), angle sword Noctua kind (Gortyna spp.) (stem borer), East moth fruit moth (Grapholita molesta) (peach (apricot) sub- heart-eating worm (oriental fruit moth)), treble cut snout moth (Hedylepta indicata) (bean pyralid (bean leaf webber)), blue or green Eimeria kind (Helicoverpa spp.) (noctuid), bollworm (Helicoverpa armigera) (cotton bollworm), the real noctuid (Helicoverpa of paddy Zea) (corn borer ridge (snout moth's larva ridge worm/bollworm)), Heliothis kind (Heliothis spp.) (noctuid), tobacco budworm (Heliothis virescens) (tobacco budworm), Hellula undalis (Hellula undalis) (cabbage Webworm), Indarbela category kind (Indarbela spp.) (root moth), the stupid moth (Keiferia of tomato Lycopersicella) (tomato pinworm), white wing open country snout moth's larva (Leucinodes the orbonalis) (eggplant of eggplant Fruit borer), pear leaf blister moth (Leucoptera malifoliella), thin moth category kind of (a Lithocollectis spp.), Grape olethreutid (Lobesia botrana) (grape fruit moth), Loxagrotis category kind (Loxagrotis Spp.) (noctuid), beans white line cutworm (Loxagrotis albicosta) (western bean cutworm), gypsymoth (Lymantria dispar) (gypsy moth), apple leaf miner (Lyonetiaclerkella) (apple leaf miner (apple Leafminer)), oil palm bag moth (Mahasena corbetti) (oil palm bagworm), Malacosoma kind (Malacosoma spp.) (tent caterpillars), lopper worm (Mamestra brassicae) (dish march moth (cabbage armyworm)), the wild snout moth's larva (Maruca testulalis) of beanpod (beans open country snout moth's larva), bag moth (Metisa plana) (knot Grass-and-insect painting), Mythimna unipuncta (true armyworm), Neoleucinodes elegantalis (small tomato moths (small tomato borer)), 3 water snout moth's larva (Nymphula depunctalis) (rice leaf roller (rice Caseworm)), winter looper (Operophthera brumata) (winter moth), European corn borer (Ostrinia Nubilalis) (European corn borer (European corn borer)), Oxydia vesulia, the brown volume moth (Pandemis of boundary Cerasana) (common glucose leaf roller (common currant tortrix)), apple brown bortrix (Pandemis heparana) (brown apple tortrix), African Bodhidharma swallowtail butterfly (Papilio demodocus), Pectinophora gossypiella (Pectinophora Gossypiella) (pink bollworm (pink bollworm)), boundary Noctua kind (Peridroma spp.) (cutworm), variegated Tiger (Peridroma saucia) (variegated cutworm), coffee leafminer (Perileucoptera Coffeella) (white coffee leafminer), phthorimaea operculella (Phthorimaea operculella) (potato tuber moth), citrus leaf lyonetid (Phyllocnisitis citrella), thin moth category kind (Phyllonorycter spp.) (leaf miner), cabbage butterfly (Pieris rapae) (external cabbage caterpillar (imported Cabbageworm)), head is by green noctuid (Plathypena scabra), India paddy spot moth (Plodia interpunctella) (Indian meal moth), diamond-back moth (Plutella xylostella) (diamondback moth), grape berry moth (Polychrosis viteana) (grape berry moth), tangerine fruit ermine moth (Prays endocarps), olive ermine moth (Prsys oleae) (olive moth), mythimna separata category kind (Pseudaletia spp.) (noctuid), Pseudaletia Unipunctata (armyworm), soybean noctuid (Pseudoplusia includens) (soybean looper), looper (Rachiplusia nu), yellow rice borer (Scirpophaga incertulas), moth stem night high category kind (Sesamia spp.) (moth Stem worm), Sesamia inferens (Sesamia inferens) (pink rice stemborer), powder stem snout moth's larva (Sesamia Nonagrioides), the brown slug moth of copper stain (Setora nitens), gelechiid (Sitotroga cerealella) (Angoumois Grain moth), pilleriana (Sparganothis pilleriana), Spodoptera kind (Spodoptera Spp.) night is coveted on (armyworm), beet armyworm (Spodoptera exigua) (beet armyworm (beet armyworm)), meadow Moth (Spodoptcra fugipcrda) (autumn armyworm (fall armyworm)), southern spodoptera (Spodoptera Oridania) (root is eaten into for (southern armyworm (southern armyworm)), emerging Noctua kind (Synanthedon spp.) Worm), Thecla basilides, Thermisia gemmatalis, casemaking clothes moth (Tineola bisselliella) (webbing Clothes moth), cabbage looper (Trichoplusia ni) (cabbage looper), Liriomyza brponiae (Tuts Absoluta), Yponomeuta kind (Yponomeuta spp.), the stupid moth of coffee leopard (Zeuzeracoffeae) (red branch ) and Zeuzera pyrina (the stupid moth of pears leopard (leopard moth)) borer.
Mallophaga ((Mallophaga) poultry louse (chewing lice))：Sheep poultry louse (Bovicola ovis) (sheep Biting louse), fire menopon gallinae (Menacanthus stramineus) (chick poultry louse (chicken body )) and shaft louse (Menopon gallinea) (common hen house (common hen house)) louse.
Orthoptera (Orthoptera) (grasshopper, locust and cricket)：Blackspot arna Zhong (Anabrus simplex) (Mo Men Katydid (Mormon cricket)), mole cricket (Gryllotalpidae) (mole cricket (mole cricket)), Asiatic migrotory locust (Locusta migratoria), grasshopper category kind (Melanoplus spp.) (grasshopper), guiding principle wing spinelet Zhong (Microcentrum Retinerve) (angle wing katydid (angular winged katydid)), Pterophylla category kind (Pterophylla Spp.) (katydid), chistocerca gregaria, fork-tail katydid (Scudderia furcata) (fork-tail shrubbery tree Zhong (fork tailed bush katydid)) and black angle oncus locust (Valanga nigricorni).
Anoplura (Phthiraptera) (sucks lice (sucking louse))：Pediculus of sucking blood kind (Haematopinus Spp.) (ox louse and pig lice), sheep jaw lice (Linognathus ovillus) (sheep lice (sheep louse)), head louse (Pediculus humanus capitis) (body louse), pediculus humanus corporis (Pediculus humanus humanus) (body louse) and the moon Lice (Pthirus pubis) (crab louse (crab louse)).
Siphonaptera (Siphonaptera) (flea)：Ctenocephalides canis (Ctenocephal ides canis) (dog flea), Ctenocephalides felis (Ctenocephalides felis) (cat flea) and Pulex irritans (Pulex irritans) (human flea).
Thysanoptera (thrips)：Cigarette brown thrip (Frankliniella fusca) (tobacco thrip), western classical architecture (Frankliniella occidentalis) (western flower thrips), Frankliniella shultzei, prestige Lian Si flower thrips (Frankliniella williamsi) (corn thrips (corn thrip)), greenhouse thrips (IIeliothrips haemorrhaidalis)(greenhouse thrip)、Riphiphorothrips cruentatus、 Hard Thrips kind (Scirtothrips spp), balloonflower root thrips (Scirtothrips cirri) (citrus thrip), tea are yellow Thrips (Scirtothrips dorsalis) (yellow tea thrips), Taeniothrips rhopalantennalis With Thrips kind (Thrips spp.).
Thysanoptera (Thysanura) (moth (bristletail))：Silverfish category kind (Lepisma spp.) (stupid worm (silverfish)) belong to kind of (Thermobia spp.) (a special mess fish) with special mess silverfish.
Acarina (Acarina)（Mite (mite) and cicada (tick))：Wu Shi honeybee shields mite (Acarapsis woodi) (honeybee gas Pipe endoparasitism mite (tracheal mite of honeybee)), Tyroglyphus kind (Acarus spp.) (food mites), Acarus siro (Acarus siro) (paddy mite (grain mite)), mango bud mite (Aceria mangiferae) (mango bud mite), Peronium Eriophyes kind (Aculops spp.), Aculops lycopersici (Aculops lycopersici) (tomato russet Mite), Aculops pelekasi, tangerine peronium goitre mite (Aculus pelekassi), Si Shi thorn goitre mites (Aculus Schlechtendali) (apple thorn goitre mite (apple rust mite)), lone star tick (Amblyomma amcricanum) (lone star tick), Boophilus kind (Boophilus spp.)（Tick), avette short hairs tick (Brevipalpus Obovatus) (privet mite), purplish red short hairs mite (Brevipalpus phoenicis) (red and black flat Mite), fat tick category kind (Demodex spp.) (mange mites), Dermacentor kind (Dermacentorspp.) (hard tick), U.S. Continent dog tick (Dermacentor variabilis) (american dog tick), dermatophagoides pteronyssinus (Dermatophagoides Pteronyssinus) (house dust mite), Eotetranychus kind (Eotetranycus spp.), Eotetranychus carpini (Eotetranychus carpini) (yellow spider mite (yellow spider mite)), Epitrimerus kind (Epitimerus Spp.), Eriophyes kind (Eriophyes spp.), Isodesspp kind (work;Odes spp.) (tick), Panonychus citri category kind ((Metatetranycus spp.), notoedres cati (Notoedres cati), Oligonychus kind (Oligonychus spp.), coffee Coffee unguiculus mite (Oligonychus coffee), ilex Oligonychus (Oligonychus ilicus) (southernred mi Te), Panonychus citri category kind (Panonychus spp.), Jie-Li enzyme-SQ (Panonychus cirri) (orange spider (citrus Red mite)), panonychus ulmi (Panonychus ulmi) (European red spider (European red mite)), tangerine wrinkle leaf Pierce goitre (Phyllocoptruta oleivora) (citrus rust mite), Polyphagotarsonemus latus Banks (Polyphagotarsonemun latus) (broad mite (broad mite)), brown dog tick (Rhipicephalus Sanguineus) (brown dog tick (brown dog tick)), root mite category kind (Rhizoglyphus spp.) (root mite (bulb Mite)), itch mite (Sarcoptes scabiei) (itch mite), avocado apical cap goitre mite (Tegolophus Perseaflorae), Tetranychus kind (Tetranychus spp.), T.urticae Koch (Tetranychus urticae) (2 spiders Spider mite (twospotted spider mite)) and Di Shi watts of mite (Varroa destructor) (honeybee mite).
Nematoda (nematode)：Aphelenchoides kind (Aphelenchoides spp.) (bud and leaf and pine wood nematode (bud And leaf＆pine wood nematode)), thorn Turbatrix kind (Belonolaimus spp.) (sting nematodes), Small loop wire Eimeria kind (Criconemella spp.) (ring nematodes), heart worm (Dirofilaria immitis) (dog heartworm), Ditylenchus kind (Ditylenchus spp.) (stem and bulb eelworm), spine rubber-insulated wire Eimeria kind (Heterodera spp.) (cyst nematode), corn SCN (Heterodera zeae) (corn cyst Nematode), Hirschmanniella kind (Hirschmanniella spp.) (root nematodes), tie Turbatrix kind (Hoplolaimus spp.) (lance nematodes), Meloidogyne kind (Meloidogyne spp.) (root-knot nematode), Meloidogyne incognita ((Meloidogyne incognita) (root-knot nematode), Onchocerca caecutiens (Onchocerca Volvulus) (hook-tail worm), Pratylenchus kind (PraLylenchus spp.) (rotten nematode (lesion Nematode)), perforation line Eimeria kind (Radopholus spp.) (similes thorne (burrowing nematode)) and banana Reniform nematode (Rotylenchus reniformis) (kidney-shaped nematode).
Symphyla (comprehensive insects)：Kahikatea worm (Scutigerella immaculata).
Especially, to diamondback moth, mythimna separata, aphid, Tetranychus cinnabarinus, still there is good prevention effect at lower doses.
Due to its positive characteristic, above-claimed cpd is advantageously used for protecting agriculture and the important crop of horticulture, family Poultry and breeding stock, and the environment that the mankind often go is from germ, the injury of insect evil mite.
To obtain ideal effect, the consumption of compound changes because of various factors, such as compound used therefor, the work protected in advance Thing, the type of harmful organism, gradient of infection, weather conditions, application method, the formulation used.
The compound dosage of 10 grams -5 kilograms of per hectare can provide sufficient preventing and treating.
Present invention additionally comprises the sterilization using formula I, II or Ш compound as active component, insecticide acaricide composition.Should The weight percentage of active component is between 0.5-99% in sterilization, insecticide acaricide composition.The sterilization, Insecticiding-miticiding combination Also including acceptable carrier in agricultural, forestry, health in thing.
The composition of the present invention can be applied in the form of preparation.Formula I, II or Ш compound as active component dissolve or It is more readily dispersible when being scattered in carrier or being configured to preparation to be used as sterilization, desinsection.For example：These chemicals can It is made into wettable powder, oil suspending agent, aqueous suspension, aqueous emulsion, aqua or missible oil etc..In these compositions, one is at least added Liquid or solid carrier is planted, and appropriate surfactant can be added when needed.
Technical scheme also includes anti-pathogen, the method for insect evil mite：By the sterilization of the present invention, Insecticiding-miticiding Composition is imposed on described germ, insect evil mite or its somatomedin.The more suitable effective amount generally selected is per hectare 10 grams to 1000 grams, preferably effective dose is 20 grams to 500 grams of per hectare.
For some applications, for example can agriculturally be added in the sterilization of the present invention, insecticide acaricide composition it is a kind of or A variety of other bactericide, Insecticides (tech) ＆ Herbicides (tech), plant growth regulator or fertilizer etc., thus can produce additional advantage and Effect.
It should be appreciated that, in scope defined by the claims of the present invention, various conversion and change can be carried out.
Embodiment
Specific examples below is used for further illustrating the present invention, but the present invention is limited to absolutely not these examples.（Except as otherwise note It is bright outer, it is raw materials used to be commercially available）
Synthetic example
Embodiment 1：The preparation of intermediate 2- (6- (4- chlorophenoxies) pyridin-3-yl) ethamine
1）The preparation of 6- (4- chlorophenoxies) methyl nicotinate
Into the 350ml DMF solution of 25.6g (0.2mol) parachlorophenol, 70% hydrogen is added portionwise Change sodium 103g (3.0mol), reaction 4h is stirred at room temperature, 34.2g (0.2mol) 6- chlorine apellagrin first is then added portionwise thereto Ester, is finished, and reactant mixture is warming up to 100 DEG C of reaction 10h, TLC monitorings after completion of the reaction, reaction solution is poured into water, acetic acid Ethyl ester is extracted, and organic phase is successively through washing, and saturated salt washing is dried, filtering, precipitation, after residue cooled and solidified, filtering, stone Oily ether washing, obtains brown solid 42.0g, i.e. 6- (4- chlorophenoxies) methyl nicotinate after drying.Fusing point：64-66℃.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.92(3H,s),6.75(1H,d),6.96(1H,d),7.11(2H,d), 7.37(2H,d),8.30(1H,d),8.81(1H,s)。
2）The preparation of (6- (4- chlorophenoxies) pyridin-3-yl) methanol
In at 0 DEG C, into the 500ml anhydrous ether solutions of 52.6g (0.2mol) 6- (4- chlorophenoxies) methyl nicotinate, drop The red aluminum toluene solution 74.5g (0.24mol) for plus 65%, is finished, and reaction 4h is stirred at room temperature, then at 0 DEG C, drips thereto Plus 10% sodium hydroxide solution prepared in advance, until reactant mixture becomes clarification, then heat to 35 DEG C of reaction 2h, TLC prisons Survey after completion of the reaction, reaction solution is poured into water, toluene extraction, organic phase is successively through washing, and saturated salt washing is dried, filtering, Precipitation, (eluant, eluent is ethyl acetate and petroleum ether to residue column chromatography（60-90 DEG C of boiling range）, volume ratio is 1:3) purifying to produce Product 42.2g, i.e. (6- (4- chlorophenoxies) pyridin-3-yl) methanol.White solid.Fusing point：100-102℃.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.20(1H,bs),4.56(2H,s),6.87(1H,d),7.04(2H, d),7.33(2H,d),7.69(1H,d),8.06(1H,s)。
3）The preparation of 5- chloromethyls -2- (4- chlorophenoxies) pyridine
In at 0 DEG C, the 350ml dichloromethane to 23.5g (0.1mol) (6- (4- chlorophenoxies) pyridin-3-yl) methanol is molten In liquid, 17.9g (0.15mol) thionyl chloride is added dropwise, finishes, reaction 4h, TLC monitoring is stirred at room temperature after completion of the reaction, decompression Excessive thionyl chloride is steamed, residue adds water, ethyl acetate extraction, organic phase is successively through washing, and saturated sodium bicarbonate is washed, and satisfies With salt washing, dry, filtering, precipitation obtains product 22.8g, i.e. 5- chloromethyls -2- (4- chlorophenoxies) pyridine.White solid.It is molten Point：78-80℃.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):4.55(2H,s),6.94(1H,d),7.09 (2H,d),7.36(2H,d),7.75(1H,d),8.15(1H,s)。
4）The preparation of 2- (6- (4- chlorophenoxies) pyridin-3-yl) acetonitrile
In at 40 DEG C, 2.69g (55mmol) Cymag is dissolved in 300ml dimethyl sulfoxide (DMSO)s, then added thereto 13.9g (50mmol) 5- chloromethyls -2- (4- chlorophenoxies) pyridine, adds the 18- crown-s 6 of catalytic amount, reactant mixture is warming up to 80 DEG C of reaction 2h, TLC monitorings after completion of the reaction, reaction solution are poured into water, toluene extraction, organic phase is successively through washing, saturation Salt is washed, and is dried, filtering, precipitation, and (eluant, eluent is ethyl acetate and petroleum ether to residue column chromatography（60-90 DEG C of boiling range）, volume Than for 1:3) product 11.2g, i.e. 2- (6- (4- chlorophenoxies) pyridin-3-yl) acetonitrile are purified to obtain.White solid.Fusing point：100- 102℃。1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.70(2H,s),6.97(1H,d),7.08(2H,d), 7.37(2H,d),7.71(1H,d),8.10(1H,s)。
5）2- (the preparations of 6- (4- chlorophenoxies pyridin-3-yl) ethamine
By 2.44g（0.01mol）2- (6- (4- chlorophenoxies) pyridin-3-yl) acetonitrile, Raney nickel (1.0g), 25% ammoniacal liquor 10ml and ethanol 50ml composition mixture in hydrogen atmosphere, stirring reaction 3-15 hour at room temperature, TLC monitoring after completion of the reaction, Raney nickel is filtered out, solvent is removed under reduced pressure and obtains pale green viscous shape liquid 2.30g, yield 95.0%.Colorless oil.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δppm1.46(2H,bs),2.70(2H,t),2.94(2H,t),6.87(1H,d), 7.07(2H,dd),7.34(2H,dd),7.55(1H,dd),8.02(1H,d)。
Embodiment 2：Compound 5-7 preparation
Into the 10ml acetonitrile solutions of 0.25g (1.0mmol) 2- (6- (4- chlorophenoxies) pyridin-3-yl) ethamine, add Triethylamine 0.15g (1.5mmol), lower addition 4- chloro- 1, the 3- dimethyl -4- pyrazol formyl chlorides 0.23g (1.2mmol) of stirring, plus 83 DEG C of reaction 2h, TLC monitorings are warming up to after complete after completion of the reaction, by reaction solution precipitation, (eluant, eluent is acetic acid to residue column chromatography Ethyl ester and petroleum ether（60-90 DEG C of boiling range）, volume ratio is 1:4) product 0.28g, i.e. compound 5-7 are purified to obtain.Faint yellow oily Thing.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):2.22(3H,s),2.90(2H,t),3.68(2H,m), 4.10(3H,s),6.89(1H,d),6.90(1H,d),7.07(2H,d),7.34(2H,d),7.62(1H,d),8.05(1H,s)。
Embodiment 3：Compound 7-7 preparation
Into the 10ml acetonitrile solutions of 0.25g (1.0mmol) 2- (6- (4- chlorophenoxies) pyridin-3-yl) ethamine, add Triethylamine 0.15g (1.5mmol), stirring is lower to add 3- ethyl -1- methyl -5- pyrazol formyl chlorides 0.21g (1.2mmol), adds After be warming up to 80 DEG C of reaction 2h, TLC is monitored after completion of the reaction, by reaction solution precipitation, and (eluant, eluent is acetic acid second to residue column chromatography Ester and petroleum ether（60-90 DEG C of boiling range）, volume ratio is 1:4) product 0.28g, i.e. compound 7-7 are purified to obtain.Colorless oil.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.02(2H,t),3.94(2H,m),6.58(1H,s),6.83 (1H,s),6.92(1H,d),7.07(2H,d),7.26(1H,s),7.35(2H,d),8.11(1H,dd),8.48(1H,s)。
Embodiment 4：Compound 37-13 preparation
To 0.23g (1.0mmol) 2- (6- (4- methylphenoxies) pyridin-3-yl) ethamine（Preparation method is with reference to as above real Example 3 is applied, except that initiation material parachlorophenol is replaced with into p-methyl phenol）10ml acetonitrile solutions in, add three second Amine 0.15g (1.5mmol), stirring is lower to add the bromo- 1- of 3-（3- chloropyridine -2- bases）- 1- pyrazoles -5- formyl chlorides 0.39g (1.2mmol), is warming up to 80 DEG C of reaction 2h, TLC monitorings after completion of the reaction, by reaction solution precipitation, residue column chromatography after adding (eluant, eluent is ethyl acetate and petroleum ether（60-90 DEG C of boiling range）, volume ratio is 1:4) product 0.30g, i.e. compound are purified to obtain 37-13.Colorless oil.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):2.36(3H,s),2.78(2H,t), 3.54(2H,m),6.64(1H,s),6.82(1H,d),7.01(2H,d),7.20(2H,d),7.48(2H,m),7.94(2H,d), 8.44(1H,s)。
Embodiment 5：The preparation of intermediate 2- (2- (4- chlorophenoxies) pyridin-3-yl) ethamine
1）The preparation of 2- (4- chlorophenoxies) methyl nicotinate
Into the 350ml DMF solution of 25.6g (0.2mol) parachlorophenol, 70% hydrogen is added portionwise Change sodium 103g (3.0mol), reaction 4h is stirred at room temperature, 34.2g (0.2mol) 2- chlorine apellagrin first is then added portionwise thereto Ester, is finished, and reactant mixture is warming up to 100 DEG C of reaction 10h, TLC monitorings after completion of the reaction, reaction solution is poured into water, acetic acid Ethyl ester is extracted, and organic phase is successively through washing, and saturated salt washing is dried, filtering, precipitation, after residue cooled and solidified, filtering, stone Oily ether washing, obtains brown solid 42.0g, i.e. 2- (4- chlorophenoxies) methyl nicotinate after drying.White solid.Fusing point：125.8 ℃。1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.95(3H,s),7.10(2H,d),7.37(2H,d), 8.26(2H,d)。
2）The preparation of (2- (4- chlorophenoxies) pyridin-3-yl) methanol
In at 0 DEG C, into the 500ml anhydrous ether solutions of 52.6g (0.2mol) 2- (4- chlorophenoxies) methyl nicotinate, drop The red aluminum toluene solution 74.5g (0.24mol) for plus 65%, is finished, and reaction 4h is stirred at room temperature, then at 0 DEG C, drips thereto Plus 10% sodium hydroxide solution prepared in advance, until reactant mixture becomes clarification, then heat to 35 DEG C of reaction 2h, TLC prisons Survey after completion of the reaction, reaction solution is poured into water, toluene extraction, organic phase is successively through washing, and saturated salt washing is dried, filtering, Precipitation, (eluant, eluent is ethyl acetate and petroleum ether to residue column chromatography（60-90 DEG C of boiling range）, volume ratio is 1:3) purifying to produce Product 42.2g, i.e. (2- (4- chlorophenoxies) pyridin-3-yl) methanol.Brown solid.Fusing point：95.1℃.1H-NMR (300MHz, it is interior Mark TMS, solvent C DCl3)δ(ppm):2.21(1H,bs),4.83(2H,s),7.04(1H,d),7.08(2H,d),7.37(2H, d),7.79(1H,t),8.07(1H,d)。
3）The preparation of 3- chloromethyls -2- (4- chlorophenoxies) pyridine
In at 0 DEG C, the 350ml dichloromethane to 23.5g (0.1mol) (6- (4- chlorophenoxies) pyridine -2- bases) methanol is molten In liquid, 17.9g (0.15mol) thionyl chloride is added dropwise, finishes, reaction 4h, TLC monitoring is stirred at room temperature after completion of the reaction, decompression Excessive thionyl chloride is steamed, residue adds water, ethyl acetate extraction, organic phase is successively through washing, and saturated sodium bicarbonate is washed, and satisfies With salt washing, dry, filtering, precipitation obtains product 22.8g, i.e. 3- chloromethyls -2- (4- chlorophenoxies) pyridine.Faint yellow solid. Fusing point：51.1℃.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):4.74(2H,s),7.04(2H,dd),7.10 (1H,d),7.37(2H,d),7.80(1H,d),8.10(1H,d)。
4）The preparation of 2- (2- (4- chlorophenoxies) pyridin-3-yl) acetonitrile
In at 40 DEG C, 2.69g (55mmol) Cymag is dissolved in 300ml dimethyl sulfoxide (DMSO)s, then added thereto 13.9g (50mmol) 6- chloromethyls -2- (4- chlorophenoxies) pyridine, adds the 18- crown-s 6 of catalytic amount, reactant mixture is warming up to 80 DEG C of reaction 2h, TLC monitorings after completion of the reaction, reaction solution are poured into water, toluene extraction, organic phase is successively through washing, saturation Salt is washed, and is dried, filtering, precipitation, and (eluant, eluent is ethyl acetate and petroleum ether to residue column chromatography（60-90 DEG C of boiling range）, volume Than for 1:3) product 11.2g, i.e. 2- (2- (4- chlorophenoxies) pyridin-3-yl) acetonitrile are purified to obtain.White solid.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.86(2H,s),7.05(1H,d),7.08(2H,d),7.38(2H,d), 7.82(1H,d),8.11(1H,d)。
5）The preparation of 2- (2- (4- chlorophenoxies) pyridin-3-yl) ethamine
By 2.44g（0.01mol）2- (2- (4- chlorophenoxies) pyridin-3-yl) acetonitrile, Raney nickel (1.0g), 25% ammoniacal liquor 10ml and ethanol 50ml composition mixture in hydrogen atmosphere, stirring reaction 3-15 hour at room temperature, TLC monitoring after completion of the reaction, Raney nickel is filtered out, solvent is removed under reduced pressure and obtains pale green viscous shape liquid 2.30g, yield 95.0%.Light green oil.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δppm1.46(2H,bs),2.94(2H,t),3.08(2H,t),6.53(1H,d), 7.35(1H,d),7.40(1H,dd),7.48(2H,dd),7.61(2H,dd)。
Embodiment 6：Compound 103-1 preparation
Into the 10ml acetonitriles of 0.25g (1.0mmol) 2- (2- (4- chlorophenoxies) pyridin-3-yl) ethamine, three second are added Amine 0.15g (1.5mmol), stirring is lower to add 4- chloro- 1,3- dimethyl -5- pyrazol formyl chlorides 0.23g (1.2mmol), after adding It is warming up to 80 DEG C of reaction 2h, TLC monitorings after completion of the reaction, by reaction solution precipitation, (eluant, eluent is ethyl acetate to residue column chromatography With petroleum ether（60-90 DEG C of boiling range）, volume ratio is 1:4) product 0.28g is purified to obtain.That is compound 103-1.White solid.1H- NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):2.21(3H,s),3.06(2H,t),3.81(2H,m),4.07(1H, s),6.77(1H,s),6.97(1H,d),7.03(1H,d),7.35(2H,d),7.59(1H,d),8.05(1H,s)。
Embodiment 7：The preparation of intermediate 2- (4- (4- chlorophenoxies) pyridin-4-yl) ethamine
1）The preparation of 2- (4- chlorophenoxies) iso methyl nicotinate
Into the 350ml DMF solution of 25.6g (0.2mol) parachlorophenol, 70% hydrogen is added portionwise Change sodium 103g (3.0mol), reaction 4h is stirred at room temperature, 34.2g (0.2mol) 2- chloroisonicotinic acid first is then added portionwise thereto Ester, is finished, and reactant mixture is warming up to 100 DEG C of reaction 10h, TLC monitorings after completion of the reaction, reaction solution is poured into water, acetic acid Ethyl ester is extracted, and organic phase is successively through washing, and saturated salt washing is dried, filtering, precipitation, after residue cooled and solidified, filtering, stone Oily ether washing, obtains brown solid 42.0g, i.e. 2- (4- chlorophenoxies) iso methyl nicotinate after drying.Fusing point：64-66℃.1H- NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):1.41(3H,t),4.43(2H,q),7.08(2H,d),7.15(2H, d),7.37(1H,d),7.56(1H,d),8.29(1H,d)。
2）The preparation of (2- (4- chlorophenoxies) pyridin-4-yl) methanol
In at 0 DEG C, into the 500ml anhydrous ether solutions of 52.6g (0.2mol) 2- (4- chlorophenoxies) iso methyl nicotinate, 65% red aluminum toluene solution 74.5g (0.24mol) is added dropwise, finishes, reaction 4h is stirred at room temperature, then at 0 DEG C, thereto 10% sodium hydroxide solution prepared in advance is added dropwise, until reactant mixture becomes clarification, 35 DEG C of reactions 2h, TLC are then heated to After completion of the reaction, reaction solution is poured into water for monitoring, toluene extraction, and organic phase is successively through washing, and saturated salt washing is dried, mistake Filter, precipitation, (eluant, eluent is ethyl acetate and petroleum ether to residue column chromatography（60-90 DEG C of boiling range）, volume ratio is 1:3) purify Product 42.2g, i.e. (2- (4- chlorophenoxies) pyridin-4-yl) methanol.Yellow liquid.1H-NMR (300MHz, internal standard TMS, solvent CDCl3)δ(ppm):3.95(1H,bs),4.70(2H,s),6.87(1H,d),6.98(1H,d),7.14(2H,d),7.34(2H, d),8.11(1H,d)。
3）The preparation of 4- chloromethyls -2- (4- chlorophenoxies) pyridine
In at 0 DEG C, the 350ml dichloromethane to 23.5g (0.1mol) (2- (4- chlorophenoxies) pyridin-4-yl) methanol is molten In liquid, 17.9g (0.15mol) thionyl chloride is added dropwise, finishes, reaction 4h, TLC monitoring is stirred at room temperature after completion of the reaction, decompression Excessive thionyl chloride is steamed, residue adds water, ethyl acetate extraction, organic phase is successively through washing, and saturated sodium bicarbonate is washed, and satisfies With salt washing, dry, filtering, precipitation obtains product 22.8g, i.e. 4- chloromethyls -2- (4- chlorophenoxies) pyridine.White solid.It is molten Point：78-80℃.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):4.59(2H,s),6.96(1H,d),7.17 (2H,d),7.33(1H,d),7.46(2H,d),8.40(1H,s)。
4）The preparation of 2- (2- (4- chlorophenoxies) pyridin-4-yl) acetonitrile
In at 40 DEG C, 2.69g (55mmol) Cymag is dissolved in 300ml dimethyl sulfoxide (DMSO)s, then added thereto 13.9g (50mmol) 4- chloromethyls -2- (4- chlorophenoxies) pyridine, adds the 18- crown-s 6 of catalytic amount, reactant mixture is warming up to 80 DEG C of reaction 2h, TLC monitorings after completion of the reaction, reaction solution are poured into water, toluene extraction, organic phase is successively through washing, saturation Salt is washed, and is dried, filtering, precipitation, and (eluant, eluent is ethyl acetate and petroleum ether to residue column chromatography（60-90 DEG C of boiling range）, volume Than for 1:3) product 11.2g, i.e. 2- (2- (4- chlorophenoxies) pyridin-4-yl) acetonitrile are purified to obtain.White solid.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.77(2H,s),6.94(1H,d),7.01(1H,d),7.09(2H,d), 7.38(2H,d),8.17(1H,s)。
5）2- (the preparations of 2- (4- chlorophenoxies pyridin-4-yl) ethamine
By 2.44g（0.01mol）2- (2- (4- chlorophenoxies) pyridin-4-yl) acetonitrile, Raney nickel (1.0g), 25% ammoniacal liquor 10ml and ethanol 50ml composition mixture in hydrogen atmosphere, stirring reaction 3-15 hour at room temperature, TLC monitoring after completion of the reaction, Raney nickel is filtered out, solvent is removed under reduced pressure and obtains rufous viscous liquid 2.30g, yield 95.0%.Brown oil.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δppm1.46(2H,bs),2.70(2H,t),2.94(2H,t),6.87(1H,d), 7.07(2H,dd),7.34(2H,dd),7.55(1H,dd),8.02(1H,d)。
Embodiment 8：Compound 95-7 preparation
Into the 10ml acetonitriles of 0.25g (1.0mmol) 2- (2- (4- chlorophenoxies) pyridin-4-yl) ethamine, three second are added Amine 0.15g (1.5mmol), stirring is lower to add 4- chloro- 1,3- dimethyl -5- pyrazol formyl chlorides 0.23g (1.2mmol), after adding It is warming up to 80 DEG C of reaction 2h, TLC monitorings after completion of the reaction, by reaction solution precipitation, (eluant, eluent is ethyl acetate to residue column chromatography With petroleum ether（60-90 DEG C of boiling range）, volume ratio is 1:4) product 0.28g is purified to obtain.That is compound 95-7.White solid.1H- NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):2.07(3H,s),3.00(2H,s),3.74(2H,s),4.09(3H, s),6.81(2H,d),7.09(3H,d),7.03(1H,d),7.36(2H,d),8.21(1H,s)。
Embodiment 9：The preparation of intermediate 6- (4- 4-trifluoromethylphenopendants) -3- aminopyridines
1）The preparation of 6- (4- 4-trifluoromethylphenopendants) -3- nitropyridines
10g (0.062mol) p-trifluoromethyl-phenol is added in 250mL there-necked flask, adding 50mL DMF makes its molten Solution, stirs 10min at room temperature, then adds 2.3g (0.095mol) NaH, continues that 3h is stirred at room temperature.After the completion of to be mixed, 10g (0.062mol) 2- chloro-5-nitropyridines are added, are to slowly warm up to after the completion of 80 DEG C, TLC question responses (about 3h), be cooled to Room temperature, adds 1000mL water, has a large amount of solids to separate out, and suction filtration is dried, obtains pale solid product 16.8g, yield：94%.1H NMR(300MHz,CDCl3)δ8.90(d,J=2.8Hz,1H),8.41(dd,J=9.0,2.8Hz,1H),7.60(d,J= 8.5Hz,2H),7.20(d,J=8.4Hz,2H),7.02(d,J=9.0Hz,1H).
2）The preparation of 6- (4- 4-trifluoromethylphenopendants) -3- aminopyridines
2.0g (7.0mmol) 6- (4- 4-trifluoromethylphenopendants) -3- nitropyridines are added in 150mL there-necked flask, 20mL AcOH are added, 1.37g (0.021mol) zinc powder is then added portionwise, reacts after the completion of 3h, TLC question responses, hangs at room temperature Solvent is evaporated off, NaOH is added dropwise（5%）The aqueous solution is adjusted to the aobvious neutrality of PH, is extracted with 3 × 20mL ethyl acetate, organic phase nothing Water MgSO4Dry, light red oil product 1.3g, yield 81% are obtained through column chromatography after outstanding steaming.
Embodiment 10：Compound 40-13 preparation
1.3g6- (4- 4-trifluoromethylphenopendants) -3- amidos pyridines (5.16mmol) are dissolved in 10mL CH2Cl2In, plus Enter and 10min is stirred under 1mL triethylamines, normal temperature, 1.66g (5.16mmol) 3- bromo- 1- (3- chloropyridine -2- bases) -1H- is then added dropwise The CH of pyrazoles -5- formyl chlorides2Cl2Solution, reacts 2h at room temperature.It is outstanding that solvent, plus 30mL water is evaporated off after the completion of TLC question responses, Extracted with 3 × 10mL ethyl acetate, the anhydrous MgSO of organic phase4Dry, pale red solid is obtained through column chromatography after outstanding steaming 2.17g, m.p.193-195 DEG C, yield 78%.1H NMR(400MHz,CDCl3)δ8.49(dd,J=4.7,1.5Hz,1H),8.42 (s,1H),8.14(d,J=11.6Hz,2H),7.94(dd,J=8.1,1.5Hz,1H),7.64(d,J=8.5Hz,2H),7.45 (dd,J=8.1,4.7Hz,1H),7.20(d,J=8.5Hz,2H),6.99–6.94(m,2H).
Other compounds of the present invention are referred to above example preparation.
Part of compounds physical data and nuclear magnetic data (1HNMR, 300MHz, internal standard TMS, ppm) it is as follows：
5-1：Colorless oil.δ(CDCl3):2.20(s,3H),2.92(t,2H),3.69(dd,2H),4.15(s,3H), 6.65(s,1H),6.95(d,1H),7.09–7.05(m,2H),7.33–7.26(m,3H),7.67(dd,1H),8.02(d,1H).
5-6：Colorless oil.δ(CDCl3):2.23(s,3H),2.92(t,2H),3.70(dd,2H),4.11(s,3H), 6.74(s,1H),6.92(d,1H),7.02(dd,1H),7.21–7.12(m,2H),7.32(t,1H),7.63(dd,1H),8.08 (d,1H).
5-7：Colorless oil.δ(CDCl3):3.02(2H,t),3.94(2H,m),6.58(1H,s),6.83(1H,s), 6.92(1H,d),7.07(2H,d),7.26(1H,s),7.35(2H,d),8.11(1H,dd),8.48(1H,s)。
5-16：δ(CDCl3):2.23(s,3H).2.36(s,3H),2.89(t,2H),3.69(dd,2H),4.11(s, 3H),6.74(s,1H),6.86(d,1H),7.02(d,2H),7.20(d,2H),7.58(dd,1H),8.06(d,1H).
5-19：Colorless oil.δ(CDCl3):2.21(s,3H),2.88(t,2H),3.67(dd,2H),3.81(s, 3H),4.10(s,3H),6.72(s,1H),6.83(d,1H),6.95–6.89(m,2H),7.09–7.01(m,2H),7.56(dd, 1H),8.04(d,1H).
5-21：Colorless oil.δ(CDCl3):2.22(s,3H),2.92(t,2H),3.70(dd,2H),4.11(s, 3H),6.74(s,1H),6.95(d,1H),7.32(d,1H),7.39(s,1H),7.48(dt,2H),7.65(dd,1H),8.07 (d,1H).
5-22：White solid.δ(CDCl3):2.23(s,3H),2.94(t,2H),3.71(dd,2H),4.11(d,3H), 6.76(s,1H),6.98(d,1H),7.35–7.14(m,2H),7.66(d,3H),8.10(s,1H).
5-83：White solid.δ(CDCl3):2.22(s,3H),2.91(t,2H),3.73–3.66(dd,2H),4.11(s, 3H),6.73(s,1H),6.98(d,1H),7.23–7.15(m,2H),7.40(d,1H),7.65(d,1H),8.02(s,1H).
5-110：Colorless oil.δ(CDCl3):2.14(s,3H),2.21(s,3H),2.88(t,2H),3.68(dd, 2H),4.11(d,3H),6.72(s,1H),6.87(d,1H),6.97(d,1H),7.18(dd,1H),7.25(dd,1H),7.59 (dd,1H),8.01(d,1H).
7-7：Colorless oil.δ(CDCl3):3.02(2H,t),3.94(2H,m),6.58(1H,s),6.83(1H,s), 6.92(1H,d),7.07(2H,d),7.26(1H,s),7.35(2H,d),8.11(1H,dd),8.48(1H,s)。
7-21：Colorless oil.δ(CDCl3):1.22(t,3H),2.61(q,2H),2.87(t,2H),3.61(q,2H), 4.09(s,3H),6.05(s,1H),6.20(s,1H),6.90(d,1H),7.07(d,2H),7.35(d,2H),7.59(dd, 1H),8.02(s,1H).
20-7：Colorless oil.δ(CDCl3):2.87(t,2H),3.65(dd,2H),3.95(s,3H),6.07(s, 1H),6.89(d,1H),7.06(d,2H),7.35(d,2H),7.59(dd,1H),7.94(s,1H),8.03(s,1H).
22-7：White solid.δ(CDCl3):2.26(s,3H),2.43(s,3H),2.87(t,2H),3.63(d,2H), 3.70(s,3H),5.60(s,1H),6.88(d,1H),7.10–6.99(m,2H),7.39–7.29(m,2H),7.60(d,1H), 8.02(d,1H).
35-13：White solid.δ(CDCl3):6.87(d,1H),6.93(s,1H),7.09(d,2H),7.20(t,1H), 7.38(d,2H),7.44(dd,1H),7.93(dd,1H),8.06(d,1H),8.10(s,1H),8.26(s,1H),8.48(dd, 1H).
36-13：Khaki solid.δ(CDCl3):6.86(d,1H),6.95(s,1H),7.06–7.00(m,2H),7.36– 7.30(m,2H),7.43(dd,1H),7.93(dd,1H),8.07(dd,1H),8.12(d,1H),8.46(dd,1H),8.65(s, 1H).
37-13：White solid.δ(CDCl3):6.97(dd,3H),2.30(s,3H),7.19(d,2H),7.42(s,1H), 7.65(dd,1H),8.02(dd,1H),8.23(d,1H),8.29(d,1H),8.52(d,1H),10.71(s,1H).
40-13：Pale red solid.δ(CDCl3):6.99–6.94(m,2H),7.20(d,2H),7.45(dd,1H),7.64 (d,2H),7.94(dd,1H),8.14(d,2H),8.42(s,1H),8.49(dd,1H).
41-13：Khaki solid.δ(CDCl3):3.80(s,3H),6.82(d,1H),6.91(d,3H),7.03(d, 2H),7.43(dd,1H),7.93(dd,1H),8.02(d,1H),8.06(s,1H),8.30(s,1H),8.47(dd,1H).
46-13：White solid.δ(CDCl3):6.93–6.88(m,2H),7.28(d,1H),7.36(s,1H),7.44 (dd,2H),7.48(d,1H),7.94(dd,1H),8.04(dd,1H),8.08(d,1H),8.47(dd,1H),8.58(s,1H).
48-13：Faint yellow solid.δ(CDCl3):6.98–6.94(m,2H),7.12(d,1H),7.29(d,1H),7.44 (dd,1H),7.47(d,1H),7.93(dd,1H),8.06(d,1H),8.11(d,1H),8.35(s,1H),8.48(dd,1H).
62-13：Yellow oil.δ(CDCl3):2.36(s,3H),2.78(t,2H),3.53(q,2H),6.32(s, 1H),6.64(s,1H),6.82(d,1H),7.01(d,2H),7.21(d,2H),7.47(dd,2H),7.91(dd,2H),8.45 (d,1H).
70-13：Yellow oil.δ(CDCl3):2.80(t,2H),3.54(dd,2H),6.37(s,1H),6.66(s, 1H),6.88(d,1H),7.03(d,1H),7.16(dd,2H),7.32(t,1H),7.41(dd,1H),7.53(dd,1H), 7.93–7.87(m,1H),7.98(d,1H),8.45(d,1H).
73-13：White solid.δ(CDCl3):2.80(t,2H),3.55(dd,2H),6.28(s,1H),6.65(s,1H), 6.95(d,1H),7.23–7.16(m,1H),7.42(d,1H),7.56(d,2H),7.74–7.70(m,1H),7.96–7.88(m, 2H),8.44(d,1H).
95-7：Yellow solid.δ(CDCl3):2.07(3H,s),3.00(2H,s),3.74(2H,s),4.09(3H,s), 6.81(2H,d),7.09(3H,d),7.03(1H,d),7.36(2H,d),8.21(1H,s).
96-7：White solid.δ(CDCl3):2.07(3H,s),3.00(2H,s),3.74(2H,s),4.09(3H,s), 6.81(2H,d),7.09(3H,d),7.03(1H,d),7.36(2H,d),8.21(1H,s).
103-1：White solid.δ2.21(s,3H),3.07(t,2H),3.82(q,2H),4.11(s,3H),6.79(bs, 1H),6.95(t,1H),7.09(d,2H),7.17(d,1H),7.38(t,2H),7.59(dd,1H),8.05(dd,1H).
103-7：White solid.δ2.21(s,3H),3.06(t,2H),3.81(q,2H),4.07(s,3H),6.77(bs, 1H),6.96(q,1H),7.06(t,2H),7.34(dd,2H),7.60(d,1H),8.04(dd,1H).
Biological activity determination
The compounds of this invention all shows good activity to a variety of germs in agriculture field, also shows and preferably kills Worm acaricidal activity.And carried out contrast test with comparison medicament.Control compound includes the CK1 of background section to CK13, Tolfenpyrad, and following KC14 to KC23 has been synthesized with reference to prior art document, structure is shown in Table 117：
The control compound table of table 117
Embodiment 11：Bactericidal activity is determined
With the compounds of this invention sample a variety of fungal diseases of plant have been carried out with Antifungal Activity in Vitro or live body protection effect Fruit is tested.Bactericidal activity measurement result is shown in following example.
(1) Antifungal Activity in Vitro is determined
Assay method is as follows：Using high-throughput screening method, i.e., by the test compound sample solvent being adapted to（Solvent Species such as acetone, methanol, DMF etc., and the Selective dissolution according to its solvability to sample, concentration needed for being configured to are to be measured Liquid.Under ultra-clean working environment, in the micropore that prepare liquid is added to 96 well culture plates, then by pathogen breeding liquid suspension add Enter wherein, the culture plate after processing is placed in constant incubator and cultivated.Investigated after 24 hours, pathogen is estimated during investigation Brood body sprouts or growing state, and the sprouting according to control treatment or growing state, evaluates compound bacteriostatic activity.
The Antifungal Activity in Vitro of part of compounds（Represented with inhibiting rate）Test result is as follows：
To the inhibiting rate of rice blast fungus：
Liquor strength be 25mg/L when, compound 5-1,5-6,5-7,5-16,5-19,5-21,5-22,5-110,73-13, 103-7 etc. inhibiting rate is 80%.
The active contrast test of part of compounds and comparison medicament is carried out, test result is shown in Table 118（"/" is represented in table Do not test）.
Antifungal Activity in Vitro of the table 118 to rice blast
Compound 25ppm Compound 25ppm Compound 25ppm Compound 25ppm
5-110 80 5-19 80 CK1 0 CK17 0
5-16 80 5-21 80 CK10 0 CK21 0
5-22 80 5-1 80 CK11 0 CK23 0
5-7 80 73-13 80 CK14 0
5-6 80 103-7 80 CK16 0
To the inhibiting rate of botrytis cinerea pers：
When liquor strength is 25mg/L, compound 5-19,5-21,5-22 etc. inhibiting rate are 50%.
The active contrast test of part of compounds and comparison medicament is carried out, test result is shown in Table 119（"/" is represented in table Do not test）.
Antifungal Activity in Vitro of the table 119 to gray mold of cucumber
Compound 25ppm Compound 25ppm Compound 25ppm Compound 25ppm
5-22 50 CK4 0 CK14 0 CK19 0
5-19 50 CK7 0 CK15 0 CK20 0
5-21 50 CK9 0 CK16 0 CK21 0
CK1 0 CK10 0 CK17 0 CK23 0
CK3 0 CK11 0 CK18 0
(2) live body protection activity is determined
Assay method is as follows：Using the potted plant assay method of live body, i.e., by a small amount of solvent of test compound sample（Solvent Species such as acetone, methanol, DMF etc., and selected, the volume ratio of quantity of solvent and spouting liquid according to its solvability to sample Equal to or less than 0.05）Dissolving, is diluted with the water containing 0.1% Tween 80, concentration prepare liquid needed for being configured to.In crop spraying 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, it would be desirable to be placed on phjytotron after the disease plant inoculating of temperature control moisturizing culture Middle culture, after disease completes to infect, moves into hot-house culture, the disease plant for not needing moisturizing culture is directly inscribed in greenhouse Plant and cultivate.After fully morbidity is compareed（Usually week age）Carry out compound protection effect assessment.
The live body protection activity test result of part of compounds is as follows：
To the live body preventive effect of cucumber downy mildew：
Liquor strength be 400mg/L when, compound 5-1,5-7,5-22,5-83,22-7,35-13,36-13,40-13, 41-13,46-13,48-13,62-13,70-13,73-13 etc. preventive effect are 100%；
When liquor strength is 100mg/L, the preventive effect of compound 5-1,5-7 etc. reaches 100%, compound 5-22,5-83, 70-13,73-13 etc. preventive effect are 90-99%；Compound 62-13 etc. preventive effect is 80-89%；
When liquor strength is 50mg/L, the preventive effect of compound 5-1,5-7 etc. reaches 100%, compound 5-22,5-83 etc. Preventive effect be 90-99%, compound 73-13 etc. preventive effect is 80-89%；
When liquor strength is 25mg/L, compound 5-1 etc. preventive effect reaches 100%, the preventive effect of compound 5-7,5-22 etc. For 90-99%；
When liquor strength is 12.5mg/L, compound 5-1 etc. preventive effect is 80-89%.
The active contrast test of part of compounds and comparison medicament is carried out, test result is shown in Table 120（"/" is represented in table Do not test）.
Live body protection activity of the table 120 to cucumber downy mildew
Compound 400mg/L 100mg/L 50mg/L 25mg/L 12.5mg/L
5-22 100 98 98 98 70
5-7 100 100 100 98 10
5-83 100 95 90 70 /
5-1 100 100 100 100 85
62-13 100 80 60 40 /
70-13 100 98 70 50 /
73-13 100 95 80 40 /
CK1 0 / / / /
CK6 0 / / / /
CK7 0 / / / /
CK8 85 / / / /
CK9 100 30 20 0 /
CK13 0 / / / /
CK17 0 / / / /
CK18 0 / / / /
CK19 0 / / / /
CK23 0 / / / /
To the live body preventive effect of corn rust：
When liquor strength is 400mg/L, compound 5-1,5-6,5-22,5-110,7-7,36-13,48-13,70-13 etc. Preventive effect be 100%, compound 5-7,103-1,103-7 etc. preventive effect is 90-99%, compound 5-16,5-19,5-21, 5-83,7-21,46-13,96-7 etc. preventive effect are 80-89%；
When liquor strength is 100mg/L, compound 5-1,36-13,48-13 etc. preventive effect are 80-89%.
The active contrast test of part of compounds and comparison medicament is carried out, test result is shown in Table 121（"/" is represented in table Do not test）.
Live body protection activity of the table 121 to corn rust
Compound 400mg/L 100mg/L 25mg/L Compound 400mg/L 100mg/L 25mg/L
5-7 98 30 0 CK10 60 / /
5-6 100 40 0 CK11 100 0 /
5-1 100 80 60 CK13 100 0 /
36-13 100 85 60 CK14 100 0 /
48-13 100 80 70 CK15 0 / /
70-13 100 50 0 CK16 100 0 /
103-7 98 70 60 CK17 0 / /
CK1 0 / / CK18 0 / /
CK6 0 / / CK19 0 / /
CK7 0 / / CK20 95 0 /
CK8 0 / / CK21 100 0 /
CK9 100 0 / CK23 0 / /
To the live body preventive effect of wheat powdery mildew：
When liquor strength is 400mg/L, compound 5-16,5-110,36-13 etc. preventive effect are 100%, compound 5-1,5- 6th, 5-7,5-22,5-83 etc. preventive effect are 80%；
When liquor strength is 100mg/L, compound 5-83 etc. preventive effect is 100%；
When liquor strength is 25mg/L, compound 5-83 etc. preventive effect is 100%；
When liquor strength is 6.25mg/L, compound 5-83 etc. preventive effect is 100%.
The active contrast test of part of compounds and comparison medicament is carried out, test result is shown in Table 122（"/" is represented in table Do not test）.
Live body protection activity of the table 122 to wheat powdery mildew
Compound 400mg/L 100mg/L 25mg/L Compound 400mg/L 100mg/L 25mg/L
5-110 100 0 / CK9 0 / /
5-16 100 0 / CK10 0 / /
5-22 80 / / CK11 0 / /
5-7 80 / / CK13 0 / /
5-6 80 / / CK14 0 / /
5-83 80 / / CK15 40 / /
5-1 80 / / CK16 0 / /
36-13 100 100 100 CK17 0 / /
CK1 0 / / CK18 0 / /
CK3 0 / / CK19 0 / /
CK4 0 / / CK20 0 / /
CK6 0 / / CK21 0 / /
CK7 0 / / CK22 0 / /
CK8 0 / / CK23 0 / /
Embodiment 12：Pesticide and miticide actility is determined
Insecticidal activity assay experiment has been carried out to several insects with the compounds of this invention.Assay method is as follows：
Testing compound acetone/methanol（1：1）Mixed solvent dissolving after, with containing 0.1%（wt）The water of Tween 80 is dilute Release to required concentration.
Using diamondback moth, black peach aphid, Tetranychus cinnabarinus as target, insecticidal activity assay is carried out using airbrush spray-on processes.
(1) determination of activity of diamondback moth, is killed
Assay method：Cabbage leaves are broken into diameter 2cm leaf dish with card punch, the pressure of airbrush spraying treatments is 10psi (is roughly equal to 0.7kg/cm2), per the spraying of leaf dish positive and negative, spouting liquid is 0.5ml.The first 2 age examination of often processing access 10 after drying in the shade Worm, often handles 3 repetitions.25 DEG C are put into after processing, is cultivated in the observation ward of relative humidity 60~70%, survival is investigated after 72 hours Borer population, calculates the death rate.
Partial test result to diamondback moth is as follows：
When liquor strength is 600mg/L, compound 5-16 etc. is 100% to diamondback moth fatal rate.
The active contrast test of part of compounds and comparison medicament is carried out, test result is shown in Table 123（"/" is represented in table Do not test）.
Preventive effect of the table 123 to diamondback moth
(2) determination of activity of black peach aphid, is killed
Assay method：Diameter 6cm culture dishes are taken, a metafiltration paper is covered at ware bottom, and appropriate running water moisturizing is added dropwise.From culture peach Clip suitable size on the cabbage plant of aphid（Diameter about 3cm）And with the cabbage leaves of 15~30 aphids, remove alatae And the aphid of face of blade, blade back is placed in culture dish upwards.The pressure of airbrush spraying treatments is that 10psi (is roughly equal to 0.7kg/cm2), spouting liquid is 0.5ml, often handles 3 repetitions.25 DEG C are put into after processing, in the observation ward of relative humidity 60~70% Culture, investigation survival borer population, calculates the death rate after 48 hours.
Partial test result to black peach aphid is as follows：
When liquor strength is 600mg/L, compound 5-6,5-7,5-16,5-19,5-22,5-110,7-7,7-21 etc. are to peach The fatal rate of aphid is 100%, and compound 5-83,37-13 etc. is 80-89%, compound 36-13,48-13 etc. to the fatal rate of black peach aphid It is 70-79% to the fatal rate of black peach aphid, compound 22-7,35-13,70-13,103-7 etc. are 60-69% to the fatal rate of black peach aphid.
The active contrast test of part of compounds and comparison medicament is carried out, test result is shown in Table 124（"/" is represented in table Do not test）.
Preventive effect of the table 124 to black peach aphid
Compound 600mg/L 100mg/L Compound 600mg/L 100mg/L Compound 600mg/L 100mg/L
5-110 100 64 36-13 71 / CK9 0 /
5-16 100 11 37-13 83 73 CK11 0 /
5-22 100 38 48-13 71 / CK12 0 /
5-7 100 0 70-13 67 / CK13 0 /
5-6 100 0 103-1 59 / CK14 28 /
5-83 81 45 103-7 67 / CK16 0 /
5-19 100 12 CK1 0 / CK17 0 /
7-7 100 69 CK5 0 / CK18 0 /
7-21 100 56 CK6 0 / CK19 0 /
22-7 67 / CK7 0 / CK21 24 /
35-13 68 / CK8 0 / CK23 0 /
(3) determination of activity of Tetranychus cinnabarinus, is killed
Assay method：Two panels true leaf Kidney bean seedling is taken, Tetranychus cinnabarinus is connected into mite and investigates after radix, sprayed with airbrush Device carries out whole strain processing, and pressure is that 10psi (is roughly equal to 0.7kg/cm2), spouting liquid is 0.5ml.3 repetitions are often handled, after processing Standard sight room is placed in, investigation survival mite number, calculates the death rate after 72 hours.
Partial test result to Tetranychus cinnabarinus is as follows：
When liquor strength is 600mg/L, compound 7-21,103-1 etc. is 100%, compound 5- to Tetranychus cinnabarinus fatal rate 16 grades are 60-69% to Tetranychus cinnabarinus fatal rate.
The active contrast test of part of compounds and comparison medicament is carried out, test result is shown in Table 125（"/" is represented in table Do not test）.Preventive effect of the table 125 to Tetranychus cinnabarinus
Compound 600mg/L 100mg/L 10mg/L Compound 600mg/L 100mg/L 10mg/L
5-110 55 / / CK9 0 / /
5-16 67 / / CK11 7 / /
7-21 100 51 28 CK13 0 / /
46-13 50 / / CK15 0 / /
103-1 100 67 63 CK16 7 / /
CK1 0 / / CK17 0 / /
CK6 0 / / CK19 0 / /
CK7 0 / / CK22 12 / /
CK8 0 / / CK23 0 / /

Claims (9)

1. a kind of pyrazol acid amide compounds, shown in compound structure below formula：
Wherein：Q is selected from
When Q (C=O) NAB- is connected to 5 of pyridine ring, compound is as shown in formula I；When Q (C=O) NAB- is connected to pyrrole At 3 of pyridine ring, compound is as shown in formula Ш：
In formula：
A is selected from hydrogen；
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen is joined directly together with pyridine ring 3 or 5 carbon2CRaRb-；
Ra、RbIt is respectively selected from hydrogen；
X is selected from O or S；
R1、R2、R3、R4、R5It is respectively selected from hydrogen, halogen, C1-C12Alkyl, halo C1-C12Alkyl；
R6、R6'、R7It is respectively selected from hydrogen；
R8Selected from C1-C8Alkyl, the pyridine radicals that following group is further substituted with is independently selected from by 1-5：Hydrogen, halogen；
R9Selected from halogen, C1-C8Alkyl；
R10Selected from hydrogen, halogen；
R10' it is selected from C1-C8Alkyl；
And the present invention does not include following 3 compounds：
2. compound according to claim 1, it is characterised in that：The compound is as shown in formula I or Ш, its formula of In I or Ш,
A is selected from hydrogen；
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen is joined directly together with pyridine ring 3 or 5 carbon2CRaRb-；
Ra、RbIt is respectively selected from hydrogen；
X is selected from O or S；
R1、R2、R3、R4、R5Selected from hydrogen, halogen, C1-C8Alkyl, halo C1-C8Alkyl；
R6、R6'、R7Selected from hydrogen；
R8Selected from C1-C6Alkyl is independently selected from the pyridine radicals that following group is further substituted with by 1-5：Hydrogen, halogen；
R9Selected from halogen, C1-C6Alkyl；
R10Selected from hydrogen, halogen；
R10' it is selected from C1-C6Alkyl.
3. compound according to claim 2, it is characterised in that：The compound is as shown in formula I or Ш, its formula of In I or Ш,
A is selected from hydrogen；
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen is joined directly together with pyridine ring 3,5 carbon2CRaRb-；
Ra、RbIt is respectively selected from hydrogen；
X is selected from O or S；
R1、R2、R3、R4、R5Selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl；
R6、R6'、R7Selected from hydrogen；
R8Selected from C1-C4Alkyl is independently selected from the pyridine radicals that following group is further substituted with by 1-5：Hydrogen, halogen；
R9Selected from halogen, C1-C4Alkyl；
R10Selected from hydrogen, halogen；
R10' it is selected from C1-C4Alkyl.
4. compound according to claim 3, it is characterised in that：The compound such as formula I-A, I-B, I-C, I-D or Shown in Ш-A：
In formula：
A、Ra、Rb、R6、R6'、R7It is selected from hydrogen；
R1、R2、R3、R4、R5It is respectively selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl；
R8' it is selected from C1-C4Alkyl；
R9Selected from halogen, C1-C4Alkyl；
R10Or R10' it is selected from hydrogen, halogen or C1-C4Alkyl；
R11、R12、R13、R14It may be the same or different, be respectively selected from hydrogen or halogen；
Y is selected from N.
5. compound according to claim 4, it is characterised in that：The compound such as formula I-A, I-B, I-C, I-D or In Ш-A,
A、Ra、Rb、R6、R6'、R7It is selected from hydrogen；
In its formula of I-A, R1、R10Selected from hydrogen or halogen；R2Selected from hydrogen, halogen or C1-C4Alkyl；R3Selected from hydrogen, halogen or halogen For C1-C4Alkyl；R4Selected from hydrogen, halogen, C1-C4Alkyl, C1-C4Alkoxy or halo C1-C4Alkyl；R5Selected from hydrogen；R8'、R9Choosing From C1-C4Alkyl；
In formula I-B, R1、R2、R3、R5Selected from hydrogen；R4Selected from halogen；R8' it is selected from C1-C4Alkyl；R9Selected from C1-C4Alkyl；R10' choosing From hydrogen or C1-C4Alkyl；
In formula I-C, Y=N；R1Selected from hydrogen or halo C1-C4Alkyl；R2Selected from hydrogen or halogen；R3、R5、R10、R12、R13、H14Choosing From hydrogen；R4Selected from hydrogen, halogen, C1-C4Alkyl, C1-C4Alkoxy or halo C1-C4Alkyl；R9、R11Selected from halogen；
In formula I-D, Y=N；R1、R3、R5Selected from hydrogen or halogen；R2、R10、R12、R13、H14Selected from hydrogen；R4Selected from hydrogen or C1-C4Alkane Base；R9、R11Selected from halogen；
In general formula III-A, R1、R2、R3、R5Selected from hydrogen；R4Selected from hydrogen or halogen；R8'、R9Selected from C1-C4Alkyl；R10Selected from halogen.
6. compound according to claim 5, it is characterised in that：The compound such as formula I-A, I-B, I-C, I-D or In Ш-A,
A、Ra、Rb、R6、R6'、R7It is selected from hydrogen；
In formula I-A, R1、R10Selected from hydrogen or chlorine；R2Selected from hydrogen, chlorine or methyl；R3Selected from hydrogen, chlorine or trifluoromethyl；R4It is selected from Hydrogen, chlorine, methyl or trifluoromethyl；R5Selected from hydrogen；R8' it is selected from methyl；R9Selected from methyl or ethyl；
In formula I-B, R1、R2、R3、R5Selected from hydrogen；R4Selected from chlorine；R8' it is selected from methyl；R9Selected from methyl；R10' it is selected from hydrogen or first Base；
In formula I-C, Y=N；R1Selected from hydrogen or trifluoromethyl；R2Selected from hydrogen or chlorine；R3、R5、R10、R12、R13、H14Selected from hydrogen；R4 Selected from hydrogen, chlorine, methyl, methoxyl group or trifluoromethyl；R9Selected from bromine；R11Selected from chlorine；
In formula I-D, Y=N；R1、R3、R5Selected from hydrogen or chlorine；R2、R10、R12、R13、H14Selected from hydrogen；R4Selected from hydrogen or methyl；R9Choosing From bromine；R11Selected from chlorine；
In general formula III-A, R1、R2、R3、R5Selected from hydrogen；R4Selected from hydrogen or chlorine；R8'、R9Selected from methyl；R10Selected from chlorine.
Killed 7. a kind of formula I, Ш compound according to claim 1 is used as preparation in agricultural, forestry or health field The purposes of microbial inoculum, insecticidal/acaricidal agent medicine.
8. a kind of sterilization and disinsection miticide composition, it is characterised in that：Make containing formula I, Ш compound as claimed in claim 1 For active component, the weight percentage of active component is 0.5-99% in composition.
9. a kind of anti-pathogen, the method for insect evil mite, it is characterised in that：The claim 8 by effective dose of non-treatment purpose Described composition is imposed on described germ, insect evil mite or its somatomedin.
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