CN106543167A - A kind of different thiazoles compound and application thereof - Google Patents
A kind of different thiazoles compound and application thereof Download PDFInfo
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- CN106543167A CN106543167A CN201510592095.5A CN201510592095A CN106543167A CN 106543167 A CN106543167 A CN 106543167A CN 201510592095 A CN201510592095 A CN 201510592095A CN 106543167 A CN106543167 A CN 106543167A
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- Prior art keywords
- alkyl
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- carbonyl
- alkoxyl
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- 0 Cc1c(*)c(*)c(*)c(C)c1* Chemical compound Cc1c(*)c(*)c(*)c(C)c1* 0.000 description 4
- HHBNDVGBHOTNQL-UHFFFAOYSA-N NCCc1cc([U]c(cc2)ccc2Cl)ncc1 Chemical compound NCCc1cc([U]c(cc2)ccc2Cl)ncc1 HHBNDVGBHOTNQL-UHFFFAOYSA-N 0.000 description 1
- DWJDJWPQWACROX-UHFFFAOYSA-N NCc1cc([U]c(cc2)ccc2Cl)ncc1 Chemical compound NCc1cc([U]c(cc2)ccc2Cl)ncc1 DWJDJWPQWACROX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Abstract
The invention belongs to agricultural bactericidal, acaricide field.More particularly to a kind of different thiazoles compound and application thereof.Shown in compound structure below formula：In formula, each substituent group is defined in the specification.The general formula compound sterilization with wide spectrum, insecticidal activity in agriculture field, have good preventive effect to various pathogenic bacterias such as corn rust, rice blast, cucumber downy mildew, cucumber anthracnose.Especially, still there is good prevention effect at lower doses to cucumber downy mildew, cucumber anthracnose.Meanwhile, the part of compounds of the present invention also has preferable acaricidal activity, can be used to prevent and treat Tetranychus cinnabarinus etc..
Description
Technical field
The invention belongs to agricultural bactericidal, acaricide field.More particularly to a kind of different thiazoles compound and application thereof.
Background technology
Patent JP2000336080 discloses the compound shown in below formula and has certain bactericidal activity, wherein chemical combination
Thing KC1 (numbering is 83 in patent) is mentioned, but no any biological activity report；
Patent WO9924413 discloses the compound shown in below formula and has certain bactericidal activity, wherein compound
KC2 (in patent numbering be 5) is 96% to scab of apple preventive effect under the conditions of 100g/ha；
Patent CN102942565 discloses the compound shown in below formula and has certain sterilization, insecticidal activity, wherein
Compound K C3 (in patent numbering be Mt005-17-1) is 40.54% to cucumber downy mildew under the conditions of 50ppm；
Under the conditions of 100ppm to aphid fatality rate be 3.67%, under the conditions of 40ppm to diamondback moth fatality rate be 42.73%；
WO2013076230 discloses following particular compound KC4 and the KC5 (19- in patent in numbering respectively table 19
24 and 19-66), but have no any concrete activity report；
WO2004046140 discloses following particular compound KC6 (numbering is II-47 in patent), but has no any concrete
Active reporter；
In 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 needs not turning off and sends structure novelty, the novel pesticide of excellent performance.It is an object of the invention to
A kind of various pathogenic bacterias of control, different thiazoles compound of insect and application thereof are provided.
Technical scheme is as follows：
The present invention provides a kind of different thiazoles compound, shown in compound structure below formula：
In formula：
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C1-
C12Alkyl, halo C1-C12Alkyl, C1-C12Alkoxyl, halo C1-C12Alkoxyl, C3-C12Cycloalkyl, C2-C12Thiazolinyl, 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-C12Alkoxyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkyl amino-carbonyl C1-C12Alkyl or
Two (C1-C12Alkyl) amino carbonyl C1-C12Alkyl；
X is selected from O or S；
R6、R6'、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C12Alkyl, halo C1-C12Alkane
Base, C3-C12Cycloalkyl, C1-C12Alkoxyl, halo C1-C12Alkoxyl, C1-C12Alkylthio group, halo C1-C12Alkylthio group, C2-
C12Thiazolinyl, halo C2-C12Thiazolinyl, C2-C12Alkynyl, halo C2-C12Alkynyl, C3-C12Alkenyloxy group, halo C3-C12Alkenyloxy group, C3-
C12Alkynyloxy group, halo C3-C12Alkynyloxy group, C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphur
Acyl group, 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-C12Alkane
Base, C1-C12Alkoxycarbonyl amino, C1-C12Alkoxy C1-C12Alkoxyl or C1-C12Alkoxy carbonyl C1-C12Alkoxyl；
R8Selected from hydrogen, halogen, cyano group, C1-C8Alkyl, halo C1-C8It is alkyl, unsubstituted or entered by the following group of 1-5
The phenyl that one step replaces：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alcoxyl
Base or halo C1-C8Alkoxyl；
R9Selected from hydrogen, halogen, cyano group, C1-C8Alkyl, benzene that is unsubstituted or being further substituted with by 1-5 following group
Base：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxyl or halo C1-C8
Alkoxyl；
A is selected from hydrogen, hydroxyl, formoxyl, C1-C12Alkyl, halo C1-C12Alkyl, C1-C12Alkoxyl, halo C1-C12Alcoxyl
Base, C3-C12Cycloalkyl, C2-C12Thiazolinyl, C2-C12Alkynyl, halo C2-C12Thiazolinyl, halo C2-C12Alkynyl, C1-C12Alkoxy C1-
C12Alkyl, halo C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkane
Base, C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphonyl, halo C1-C12Alkyl sulfonyl
Base, C1-C12Alkyl amino sulfonyl, two (C1-C12Alkyl) amino-sulfonyl, C1-C12Alkylsulfonyl aminocarbonyl, C1-C12
Alkyl-carbonyl-amino sulfonyl, C3-C12Cycloalkyloxycarbonyl, C1-C12Alkyl-carbonyl, halo C1-C12Alkyl-carbonyl, C1-C12
Alkoxy carbonyl, halo C1-C12Alkoxy carbonyl, C1-C12Alkyl-carbonyl C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkane
Base, C1-C12Alkyl amino-carbonyl, two (C1-C12Alkyl) amino carbonyl, C2-C12Allyloxycarbonyl, C2-C12Alkynyloxycar bonyl,
C1-C12Alkoxy C1-C12Alkoxy carbonyl, (miscellaneous) aryl carbonyl that is unsubstituted or being further substituted with by 1-5 following group
C1-C6Alkyl, (miscellaneous) aryl carbonyl, (miscellaneous) aryloxycarbonyl, (miscellaneous) aryl C1-C6Alkyloxycarbonyl or (miscellaneous) aryl C1-C6
Alkyl：Halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl or halo C1-C6Alkoxyl；
B is the substituent group being joined directly together by 3,4 or 5 carbon atoms of amide nitrogen atom and hexa-atomic aromatic rings ,-CRaRb、-
CH2CRaRb- or-CH2CRaRbCRaRb-；Ra、RbMay be the same or different, be respectively selected from hydrogen, C1-C12Alkyl, C3-C12Cycloalkyl, C2-
C12Thiazolinyl, C2-C12Alkynyl, halo C2-C12Thiazolinyl, halo C2-C12Alkynyl, C1-C12Alkoxy C1-C12Alkyl, it is unsubstituted or
The aryl C being further substituted with by 1-5 following group1-C6Alkyl or heteroaryl C1-C6Alkyl：Halogen, C1-C6Alkyl, halo
C1-C6Alkyl, C1-C6Alkoxyl or halo C1-C6Alkoxyl or Ra, RbWith the carbon composition C being connected3-C8Ring；
W is selected from CH or N.
The more preferred compound of the present invention is：In formula
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C1-
C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxyl, halo C1-C8Alkoxyl, C3-C8Cycloalkyl, C2-C8Thiazolinyl, C2-C8Alkynyl,
C2-C8Alkenyloxy group, halo C2-C8Alkenyloxy group, C2-C8Alkynyloxy group, halo C2-C8Alkynyloxy group, C1-C8Alkylthio group, halo C1-C8Alkane sulfur
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；
X is selected from O or S；
R6、R6'、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C8Alkyl, halo C1-C8Alkane
Base, C3-C6Cycloalkyl, C1-C8Alkoxyl, halo C1-C8Alkoxyl, C1-C8Alkylthio group, halo C1-C8Alkylthio group, C2-C8Alkene
Base, halo C2-C8Thiazolinyl, C2-C8Alkynyl, halo C2-C8Alkynyl, C3-C8Alkenyloxy group, halo C3-C8Alkenyloxy group, C3-C8Alkynyloxy group,
Halo C3-C8Alkynyloxy group, C1-C8Alkyl sulphinyl, halo C1-C8Alkyl sulphinyl, C1-C8Alkyl sulphonyl, halo C1-
C8Alkyl sulphonyl, C1-C8Alkyl-carbonyl, halo C1-C8Alkyl-carbonyl, C1-C8Alkyl carbonyl epoxide, C1-C8Alkyl-carbonyl ammonia
Base, C1-C8Alkyl sulphonyl epoxide, C1-C8Alkoxy carbonyl, C1-C8Alkoxy carbonyl C1-C8Alkyl, C1-C8Alkoxy carbonyl
Amino, C1-C8Alkoxy C1-C8Alkoxyl or C1-C8Alkoxy carbonyl C1-C8Alkoxyl；
R8Selected from hydrogen, halogen, cyano group, C1-C6Alkyl, halo C1-C6It is alkyl, unsubstituted or entered by the following group of 1-5
The phenyl that one step replaces：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alcoxyl
Base or halo C1-C6Alkoxyl；
R9Selected from hydrogen, halogen, cyano group, C1-C6Alkyl, benzene that is unsubstituted or being further substituted with by 1-5 following group
Base：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl or halo C1-C6
Alkoxyl；
A is selected from hydrogen, hydroxyl, formoxyl, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxyl, halo C1-C8Alkoxyl,
C3-C8Cycloalkyl, C2-C8Thiazolinyl, C2-C8Alkynyl, halo C2-C8Thiazolinyl, halo C2-C8Alkynyl, C1-C8Alkoxy C1-C8Alkyl,
Halo C1-C8Alkoxy C1-C8Alkyl, C1-C8Alkylthio group C1-C8Alkyl, halo C1-C8Alkylthio group C1-C8Alkyl, C1-C8Alkyl is sub-
Sulfonyl, halo C1-C8Alkyl sulphinyl, C1-C8Alkyl sulphonyl, halo C1-C8Alkyl sulphonyl, C1-C8Alkyl amino sulphur
Acyl group, two (C1-C8Alkyl) amino-sulfonyl, C1-C8Alkylsulfonyl aminocarbonyl, C1-C8Alkyl-carbonyl-amino sulfonyl,
C3-C8Cycloalkyloxycarbonyl, C1-C8Alkyl-carbonyl, halo C1-C8Alkyl-carbonyl, C1-C8Alkoxy carbonyl, halo C1-C8Alkane
Epoxide carbonyl, C1-C8Alkyl-carbonyl C1-C8Alkyl, C1-C8Alkoxy carbonyl C1-C8Alkyl, C1-C8Alkyl amino-carbonyl, two (C1-
C8Alkyl) amino carbonyl, C2-C8Allyloxycarbonyl, C2-C8Alkynyloxycar bonyl, C1-C8Alkoxy C1-C8Alkoxy carbonyl, do not take
(miscellaneous) aryl carbonyl C that is generation or being further substituted with by 1-3 following group1-C6Alkyl, (miscellaneous) aryl carbonyl, (miscellaneous) aryloxy group
Carbonyl, (miscellaneous) aryl C1-C6Alkyloxycarbonyl or (miscellaneous) aryl C1-C6Alkyl：Halogen, nitro, cyano group, C1-C4Alkyl, halo
C1-C4Alkyl, C1-C4Alkoxyl or halo C1-C4Alkoxyl；
B is the substituent group being joined directly together by 3,4 or 5 carbon atoms of amide nitrogen atom and hexa-atomic aromatic rings ,-CRaRb、-
CH2CRaRb- or-CH2CRaRbCRaRb-；Ra、RbMay be the same or different, be respectively selected from hydrogen, C1-C8Alkyl, C3-C8Cycloalkyl, C2-
C8Thiazolinyl, C2-C8Alkynyl, halo C2-C8Thiazolinyl, halo C2-C8Alkynyl, C1-C8Alkoxy C1-C8It is alkyl, unsubstituted or by 1-3
The aryl C that individual following group is further substituted with1-C4Alkyl or heteroaryl C1-C4Alkyl：Halogen, C1-C4Alkyl, halo C1-C4Alkane
Base, C1-C4Alkoxyl or halo C1-C4Alkoxyl；Or Ra、RbWith the carbon composition C being connected3-C8Ring；
W is selected from CH or N.
Further preferred compound is：In formula
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C1-
C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxyl, halo C1-C4Alkoxyl, C3-C4Cycloalkyl, C2-C4Thiazolinyl, C2-C4Alkynyl,
C2-C4Alkenyloxy group, halo C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halo C2-C4Alkynyloxy group, C1-C4Alkylthio group, halo C1-C4Alkane sulfur
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；
X is selected from O or S；
R6、R6'、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkane
Base, C3-C6Cycloalkyl, C1-C4Alkoxyl, halo C1-C4Alkoxyl, C1-C4Alkylthio group, halo C1-C4Alkylthio group, C2-C4Alkene
Base, C2-C4Alkynyl, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, C1-C4Alkyl-carbonyl or C1-C4Alkoxy C1-C4Alkane
Epoxide；
R8Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4It is alkyl, unsubstituted or entered by the following group of 1-5
The phenyl that one step replaces：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alcoxyl
Base or halo C1-C6Alkoxyl；
R9Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, benzene that is unsubstituted or being further substituted with by 1-5 following group
Base：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxyl or halo C1-C4
Alkoxyl；
A is selected from hydrogen, C1-C4Alkyl, C1-C4Alkoxy carbonyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkoxyl carbonyl
Base, C1-C4Alkyl-carbonyl C1-C4Alkyl；
B is the substituent group being joined directly together by 3,4 or 5 carbon atoms of amide nitrogen atom and hexa-atomic aromatic rings ,-CRaRb、-
CH2CRaRb- or-CH2CRaRbCRaRb-；Ra、RbMay be the same or different, be respectively selected from hydrogen, methyl or ethyl；
W is selected from CH or N.
Compound still more preferably is：
Compound of the structure as shown in I-A, I-B, I-C, I-D, I-E, II-A, III-A and III-B：
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C4
Alkyl, C1-C4Alkoxyl or halo C1-C4Alkoxyl；
R6、R6'、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkane
Base, C1-C4Alkoxyl, halo C1-C4Alkoxyl, C1-C4Alkyl-carbonyl；
R8Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4Alkyl；
R9Selected from hydrogen, halogen, cyano group, C1-C4Alkyl；
A is selected from hydrogen；
Ra、RbMay be the same or different, be respectively selected from hydrogen, methyl or ethyl.
Compound still further preferably is：
In formula I-A, I-B, I-C, I-D, I-E, II-A, III-A or III-B
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C4
Alkyl, C1-C4Alkoxyl or halo C1-C4Alkoxyl；
R6、R6'、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C4Alkyl；
R8Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4Alkyl；
R9Selected from hydrogen, halogen, cyano group, C1-C4Alkyl；
A is selected from hydrogen；
Ra、RbSelected from hydrogen.
Compound in the present invention still more preferably is：
In formula I-A, I-B, I-C, I-D, I-E, II-A, III-A or III-B
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C2
Alkyl, C1-C4Alkoxyl or halo C1-C2Alkoxyl；
R6、R6'、R7May be the same or different, be respectively selected from hydrogen, halogen, C1-C4Alkyl；
R8Selected from hydrogen, halogen, cyano group, C1-C2Alkyl, halo C1-C2Alkyl；
R9Selected from hydrogen, halogen, cyano group, C1-C2Alkyl；
A is selected from hydrogen；
Ra、RbSelected from hydrogen.
Currently preferred particular compound is：
In formula I-A, I-B, I-C, I-D, I-E, II-A, III-A or III-B
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C2
Alkyl, C1-C4Alkoxyl；
R6、R6'、R7Selected from hydrogen；
R8Selected from halogen；
R9Selected from halogen；
A is selected from hydrogen；
Ra、RbSelected from hydrogen.
In the definition of general formula compound given above, collect the following substituent group 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 group 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..Alkoxyl：Straight or branched alkane
Base, Jing oxygen atoms are bonded and are connected in structure.Halogenated alkoxy：Straight or branched alkoxyl, the hydrogen atom on these alkoxyls
Partly or entirely 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, Jing sulphur atoms are bonded
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..Thiazolinyl：Straight or branched alkenes, such as vinyl, 1- acrylic, 2- acrylic and different cyclobutenyls, penta
Thiazolinyl and hexenyl isomers.Thiazolinyl also includes many alkenes, such as 1,2- allene base and 2,4- hexadienyl.Haloalkenyl group：Directly
Chain or a chain alkene, the hydrogen atom on these thiazolinyls partly or entirely can be replaced by halogen atom.Alkynyl：Straight or branched alkynes
Class, such as acetenyl, 1- propinyls, 2-propynyl and different butynyls, pentynyl and hexynyl isomers.Alkynyl also includes
The group being made up of multiple three keys, such as 2,5- adipic alkynyls.Halo alkynyl：Straight or branched acetylenic, the hydrogen on these alkynyls
Atom partly or entirely can be replaced by halogen atom.Alkenyloxy group：Straight or branched alkenes, Jing oxygen atoms are bonded and are connected in structure.
Halo alkenyloxy group：Straight or branched alkenyloxy group, the hydrogen atom in these alkenyloxy groups partly or entirely can be replaced by halogen atom.
Alkynyloxy group：Straight or branched acetylenic, Jing oxygen atoms are bonded and are connected in structure.Halo alkynyloxy group：Straight or branched alkynyloxy group, at this
Hydrogen atom on a little alkynyloxy groups partly or entirely can be replaced by halogen atom.Allyloxycarbonyl：Such as CH2=CHCH2OCO- etc..Alkynes
Epoxide carbonyl：Such as CH ≡ CCH2OCO- etc..Alkyl amino：Straight or branched alkyl, Jing nitrogen-atoms are bonded and are connected in structure.
Haloalkylamino：Straight or branched alkyl amino, the hydrogen atom on these alkyl can partly or entirely by halogen
Atomic lock replaces.Dialkyl amido：Such as (CH3) 2NH-, (C2H5) 2NH-.Alkyl sulphinyl：Straight or branched alkyl Jing
Sulfinyl (- SO-) is connected in structure, such as methylsulfinyl.Cyano alkoxy：CN- alkoxyls, such as CNCH3O,
CNC2H5O.Alkyl sulphinyl：Straight or branched alkyl Jing sulfinyl (- SO-) is connected in structure, such as methylsulfinyl
Base.Alkylsulfinyl：Straight or branched alkyl sulfinyl, the hydrogen atom on its alkyl can be partly or entirely former by halogen
Son is replaced.Alkyl sulphonyl：Straight or branched alkyl Jing sulfonyl (- SO2-) is connected in structure, such as methyl sulphonyl.Halogen
Substituted alkyl sulfonyl：Straight or branched alkyl sulfonyl, the hydrogen atom on its alkyl partly or entirely can be replaced by halogen atom.
Alkyl-carbonyl：Alkyl Jing carbonyls are connected in structure, such as CH3CO-, CH3CH2CO-.Halogenated alkyl carbonyl：The alkane of alkyl-carbonyl
Hydrogen atom on base partly or entirely can be replaced by halogen atom, such as CF3CO-.Alkyl carbonyl epoxide：Such as CH3COO-,
CH3CH2NHCOO-.Alkyl sulphonyl epoxide：Alkyl-S (O) 2-O-.Alkoxy carbonyl：Alkyl-O-CO-, such as CH3OCO-,
C2H5OCO-.Halo alkoxy carbonyl：Hydrogen atom on the alkyl of alkoxy carbonyl partly or entirely can be replaced by halogen atom,
Such as ClCH2CH2OCO-, CF3CH2OCO- etc..Alkoxy carbonyl alkyl：Alkoxy carbonyl-alkyl-, such as CH3OCOCH2-.Alkane
Epoxide carbonyl alkoxyl：Alkyl-O-CO- alkyl-O-.Alkoxycarbonyl amino：Alkyl-O-CO-NH-.Alkoxyalkyl：Alkane
Base-O- alkyl-, such as CH3OCH2-.Halogenated alkoxy alkyl：Hydrogen atom on the alkyl of alkoxyalkyl can be part or all of
Replaced by halogen atom.Such as ClCH2CH2OCH2-.Alkylthio alkyl：Alkyl-S-alkyl-, such as CH3SCH2-.Alkyl halide sulfur
Base alkyl：Hydrogen atom on the alkyl of alkylthio alkyl partly or entirely can be replaced by halogen atom, such as ClCH2CH2SCH2-,
CF3CH2SCH2- etc..Alkyloxy-alkoxy：Alkyl-O- alkyl-O-, such as CH3OCH2O-.Alkyl amino sulfonyl：Alkyl-
NH-SO2-.Dialkyl amino sulfonyl：(alkyl) 2-N-SO2-.Alkylsulfonyl aminocarbonyl：Alkyl-SO2-NH-CO-.Alkane
Base carbonylamino sulfonyl：Alkyl-CO-NH-SO2-.Cycloalkyloxycarbonyl：Such as ring propoxycarbonyl, cyclohexyloxy carbonyl
Deng.Alkylcarbonylalkyl：Alkyl-CO- alkyl-.Alkyl amino-carbonyl：Alkyl-NH-CO-, such as CH3NHCO-, (CH3)
2NCO-.Dialkyl amino carbonyl：(alkyl) 2-NH-CO-, such as (CH3) 2-N-CO-, (C2H5) 2-N-CO-.Alkoxyl alcoxyl
Base carbonyl：Such as CH3O CH2CH2OCO- etc..Alkyl amino alkyl carbonyl：Such as CH3NH2COCH2-.Dialkyl amino carbonyl alkane
Base：Such as (CH3) 2NH2COCH2-.Aryl：Including phenyl or naphthyl etc..Heteroaryl：Refer to containing one or more N, O, S hetero atoms
Five-membered ring or hexatomic ring.Such as pyrrole radicals, furyl, thienyl, imidazole radicals, pyrazolyl, oxazolyl, thiazolyl, isoxazole
Base, isothiazolyl, pyridine radicals, pyrimidine radicals, pyridazinyl, pyridazine ketone group, indyl, benzofuranyl, benzoxazolyl, benzo thiophene
Fen base, benzothiazolyl, benzo isoxazolyl, benzisothia oxazolyl, benzimidazolyl, benzopyrazoles base, quinoxalinyl etc..
(miscellaneous) aryl carbonyl：Such as benzoyl, 4- chlorobenzene formacyls, picolinoyl, pyrimidine formoxyl, pyrazoyl etc..(miscellaneous)
Aryloxycarbonyl：Such as phenyloxycarbonyl, 4- cHorophenoxycarbonyls, 4-nitrophenoxy carbonyl, naphthoxycarbonyl, pyridyloxy carbonyl
Base, 2-pyrimidinyl oxy carbonyl etc..(miscellaneous) aryl alkyl carbonyl：Such as PhCOCH2-.(miscellaneous) aryl alkyl Epoxide carbonyl：Such as benzyl epoxide
Carbonyl, 4- chlorobenzyl Epoxide carbonyls, 4- trifluoromethyl benzyl Epoxide carbonyls, picolyl Epoxide carbonyl etc..(miscellaneous) aryl alkyl：
As benzyl, phenethyl, to chlorophenylmethyl,Deng.
Table 1 lists R in formula I, II or Ш respectively to table 38、R9、Ra、RbThe concrete substituent group in part, but they are not
These substituent groups are only limitted to, in formula I, II or Ш other substituent groups are as previously mentioned.
1 R of table8Substituent group
| R8 | R8 | R8 |
| H | F | Cl |
| Br | I | CN |
| CH3 | C2H5 | CHF2 |
| CFH2 | CF3 | CH2CHF2 |
2 R of table9Substituent group
| R9 | R9 | R9 |
| H | F | Cl |
| Br | I | CN |
| CH3 | C2H5 |
3 R of tablea(Rb) substituent group
The part of compounds of the present invention can be illustrated with the particular compound listed in table 4- tables 146, but is not limited
The present invention.In general formula compound I-A, I-B, I-C, I-D, I-E, II-A, III-A or III-B for being related in table, R6=R6'=H.
In formula I-A
Work as A=H, R8=R9=Cl, R7During=H, R1、R2、R3、R4、R5Substituent group, is shown in Table 4, and representation compound numbering is 4-
1---4-180。
Table 4
Table 5：Work as A=H, R8=Cl, R9=CH3, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4, represent chemical combination
Thing numbering is 5-1---5-180, is corresponding in turn to the 1-180 of table 4.
Table 6：Work as A=H, R8=CH3, R9=H, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4, represent chemical combination
Thing numbering is 6-1---6-180, is corresponding in turn to the 1-180 of table 4.
Table 7：Work as A=H, R8=H, R9=CH3, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4, represent chemical combination
Thing numbering is 7-1---7-180, is corresponding in turn to the 1-180 of table 4.
Table 8：Work as A=H, R8=H, R9=CN, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4, representation compound
Numbering is 8-1---8-180, is corresponding in turn to the 1-180 of table 4.
Table 9：Work as A=H, R8=H, R9=CH2Cl, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4, representativeization
Compound numbering is 9-1---9-180, is corresponding in turn to the 1-180 of table 4.
Table 10：A=H, R8=R9=Cl, R7During=Cl, substituent R1、R2、R3、R4、R5Consistent with table 4, representation compound is compiled
Number be 10-1---10-180, be corresponding in turn to the 1-180 of table 4.
Table 11：Work as A=H, R8=Cl, R9=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 4, representativeization
Compound numbering is 11-1---11-180, is corresponding in turn to the 1-180 of table 4.
Table 12：Work as A=H, R8=CH3, R9=H, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 4, representativeization
Compound numbering is 12-1---12-180, is corresponding in turn to the 1-180 of table 4.
Table 13：Work as A=H, R8=H, R9=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 4, representativeization
Compound numbering is 13-1---13-180, is corresponding in turn to the 1-180 of table 4.
Table 14：Work as A=H, R8=H, R9=CN, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 4, represent chemical combination
Thing numbering is 14-1---14-180, is corresponding in turn to the 1-180 of table 4.
Table 15：Work as A=H, R8=H, R9=CH2Cl, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 4, represent
Compound number is 15-1---15-180, is corresponding in turn to the 1-180 of table 4.
In formula I-B,
Table 16：Work as A=H, R8=R9=Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4, generation
Table compound number is 16-1---16-180, is corresponding in turn to the 1-180 of table 4.
Table 17：Work as A=H, R8=Cl, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4,
Representation compound numbering is 17-1---17-180, is corresponding in turn to the 1-180 of table 4.
Table 18：Work as A=H, R8=CH3, R9=H, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4,
Representation compound numbering is 18-1---18-180, is corresponding in turn to the 1-180 of table 4.
Table 19：Work as A=H, R8=H, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4,
Representation compound numbering is 19-1---19-180, is corresponding in turn to the 1-180 of table 4.
Table 20：Work as A=H, R8=H, R9=CN, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 4,
Representation compound numbering is 20-1---20-180, is corresponding in turn to the 1-180 of table 4.
Table 21：Work as A=H, R8=H, R9=CH2Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 21-1---21-180, is corresponding in turn to the 1-180 of table 4.
Table 22：Work as A=H, R8=R9=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 4,
Representation compound numbering is 22-1---22-180, is corresponding in turn to the 1-180 of table 4.
Table 23：Work as A=H, R8=Cl, R9=CH3, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 23-1---23-180, is corresponding in turn to the 1-180 of table 4.
Table 24：Work as A=H, R8=CH3, R9=H, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 24-1---24-180, is corresponding in turn to the 1-180 of table 4.
Table 25：Work as A=H, R8=H, R9=CH3, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 25-1---25-180, is corresponding in turn to the 1-180 of table 4.
Table 26：Work as A=H, R8=H, R9=CN, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 26-1---26-180, is corresponding in turn to the 1-180 of table 4.
Table 27：Work as A=H, R8=H, R9=CH2Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 4
Unanimously, representation compound numbering is 27-1---27-180, is corresponding in turn to the 1-180 of table 4.
Table 28：Work as A=H, R8=R9=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5It is consistent with table 4,
Representation compound numbering is 28-1---28-180, is corresponding in turn to the 1-180 of table 4.
Table 29：Work as A=H, R8=Cl, R9=CH3, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 4
Unanimously, representation compound numbering is 29-1---29-180, is corresponding in turn to the 1-180 of table 4.
Table 30：Work as A=H, R8=CH3, R9=H, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 30-1---30-180, is corresponding in turn to the 1-180 of table 4.
Table 31：Work as A=H, R8=H, R9=CH3, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 31-1---31-180, is corresponding in turn to the 1-180 of table 4.
Table 32：Work as A=H, R8=H, R9=CN, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 32-1---32-180, is corresponding in turn to the 1-180 of table 4.
Table 33：Work as A=H, R8=H, R9=CH2Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 4
Unanimously, representation compound numbering is 33-1---33-180, is corresponding in turn to the 1-180 of table 4.
Table 34：Work as A=H, R8=R9=Cl, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5It is consistent with table 4,
Representation compound numbering is 34-1---34-180, is corresponding in turn to the 1-180 of table 4.
Table 35：Work as A=H, R8=Cl, R9=CH3, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 4
Unanimously, representation compound numbering is 35-1--35-180, is corresponding in turn to the 1-180 of table 4.
Table 36：Work as A=H, R8=CH3, R9=H, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 36-1---36-180, is corresponding in turn to the 1-180 of table 4.
Table 37：Work as A=H, R8=H, R9=CH3, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 37-1---37-180, is corresponding in turn to the 1-180 of table 4.
Table 38：Work as A=H, R8=H, R9=CN, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 38-1---38-180, is corresponding in turn to the 1-180 of table 4.
Table 39：Work as A=H, R8=H, R9=CH2Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 4
Unanimously, representation compound numbering is 39-1---39-180, is corresponding in turn to the 1-180 of table 4.
Table 40：Work as A=H, R8=R9=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table 4 one
Cause, representation compound numbering is 40-1---40-180, is corresponding in turn to the 1-180 of table 4.
Table 41：Work as A=H, R8=Cl, R9=CH3, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With
Table 4 is consistent, and representation compound numbering is 41-1---41-180, is corresponding in turn to the 1-180 of table 4.
Table 42：Work as A=H, R8=CH3, R9=H, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table
4 is consistent, and representation compound numbering is 42-1---42-180, is corresponding in turn to the 1-180 of table 4.
Table 43：Work as A=H, R8=H, R9=CH3, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table
4 is consistent, and representation compound numbering is 43-1---43-180, is corresponding in turn to the 1-180 of table 4.
Table 44：Work as A=H, R8=H, R9=CN, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table 4
Unanimously, representation compound numbering is 44-1---44-180, is corresponding in turn to the 1-180 of table 4.
Table 45：Work as A=H, R8=H, R9=CH2Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With
Table 4 is consistent, and representation compound numbering is 45-1---45-180, is corresponding in turn to the 1-180 of table 4.
In formula I-C,
Work as A=H, R8=R9=Cl, Ra=Rb=R7During=H, R1、R2、R3、R4、R5For different substituent groups, 46 are shown in Table, generation
Table compound number is 46-1---46-16.
Table 46
| Numbering | R1 | R2 | R3 | R4 | R5 |
| 1 | H | H | H | H | H |
| 2 | H | H | H | Cl | H |
| 3 | H | H | H | CF3 | H |
| 4 | H | H | H | OCH3 | H |
| 5 | H | H | H | CH3 | H |
| 6 | H | H | H | NO2 | H |
| 7 | H | H | H | F | H |
| 8 | CF3 | H | H | H | H |
| 9 | Cl | H | H | H | H |
| 10 | H | H | H | H | Cl |
| 11 | H | Cl | H | Cl | H |
| 12 | H | Cl | H | CF3 | H |
| 13 | H | F | H | CN | H |
| 14 | H | H | Cl | H | Cl |
| 15 | H | CH3 | H | H | H |
| 16 | F | H | H | F | H |
Table 47：Work as A=H, R8=Cl, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 47-1---47-16, is corresponding in turn to the 1-16 of table 46.
Table 48：Work as A=H, R8=CH3, R9=H, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 48-1---48-16, is corresponding in turn to the 1-16 of table 46.
Table 49：Work as A=H, R8=H, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 49-1---49-16, is corresponding in turn to the 1-16 of table 46.
Table 50：Work as A=H, R8=H, R9=CN, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46,
Representation compound numbering is 50-1---50-16, is corresponding in turn to the 1-16 of table 46.
Table 51：Work as A=H, R8=H, R9=CH2Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 51-1---51-16, is corresponding in turn to the 1-16 of table 46.
Table 52：Work as A=H, R8=R9=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 52-1---52-16, is corresponding in turn to the 1-16 of table 46.
Table 53：Work as A=H, R8=Cl, R9=CH3, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 53-1---53-16, is corresponding in turn to the 1-16 of table 46.
Table 54：Work as A=H, R8=CH3, R9=H, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 55-1---54-16, is corresponding in turn to the 1-16 of table 46.
Table 55：Work as A=H, R8=H, R9=CH3, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 55-1---55-16, is corresponding in turn to the 1-16 of table 46.
Table 56：Work as A=H, R8=H, R9=CN, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 56-1---56-16, is corresponding in turn to the 1-16 of table 46.
Table 57：Work as A=H, R8=H, R9=CH2Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 57-1---57-16, is corresponding in turn to the 1-16 of table 46.
Table 58：Work as A=H, R8=R9=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 58-1---58-16, is corresponding in turn to the 1-16 of table 46.
Table 59：Work as A=H, R8=Cl, R9=CH3, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 59-1---59-16, is corresponding in turn to the 1-16 of table 46.
Table 60：Work as A=H, R8=CH3, R9=H, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 60-1---60-16, is corresponding in turn to the 1-16 of table 46.
Table 61：Work as A=H, R8=H, R9=CH3, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 61-1---61-16, is corresponding in turn to the 1-16 of table 46.
Table 62：Work as A=H, R8=H, R9=CN, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 62-1---62-16, is corresponding in turn to the 1-16 of table 46.
Table 63：Work as A=H, R8=H, R9=CH2Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table
46 is consistent, and representation compound numbering is 63-1---63-16, is corresponding in turn to the 1-16 of table 46.
Table 64：Work as A=H, R8=R9=Cl, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 64-1---64-16, is corresponding in turn to the 1-16 of table 46.
Table 65：Work as A=H, R8=Cl, R9=CH3, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 65-1---65-16, is corresponding in turn to the 1-16 of table 46.
Table 66：Work as A=H, R8=CH3, R9=H, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 66-1---66-16, is corresponding in turn to the 1-16 of table 46.
Table 67：Work as A=H, R8=H, R9=CH3, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 67-1---67-16, is corresponding in turn to the 1-16 of table 46.
Table 68：Work as A=H, R8=H, R9=CN, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 68-1---68-16, is corresponding in turn to the 1-16 of table 46.
Table 69：Work as A=H, R8=H, R9=CH2Cl, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table
46 is consistent, and representation compound numbering is 69-1---69-16, is corresponding in turn to the 1-16 of table 46.
Table 70：Work as A=H, R8=R9=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 70-1---70-16, is corresponding in turn to the 1-16 of table 46.
Table 71：Work as A=H, R8=Cl, R9=CH3, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With
Table 46 is consistent, and representation compound numbering is 71-1---71-16, is corresponding in turn to the 1-16 of table 46.
Table 72：Work as A=H, R8=CH3, R9=H, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table
46 is consistent, and representation compound numbering is 72-1---72-16, is corresponding in turn to the 1-16 of table 46.
Table 73：Work as A=H, R8=H, R9=CH3, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table
46 is consistent, and representation compound numbering is 73-1---73-16, is corresponding in turn to the 1-16 of table 46.
Table 74：Work as A=H, R8=H, R9=CN, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table
46 is consistent, and representation compound numbering is 74-1---74-16, is corresponding in turn to the 1-16 of table 46.
Table 75：Work as A=H, R8=H, R9=CH2Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With
Table 46 is consistent, and representation compound numbering is 75-1---75-16, is corresponding in turn to the 1-16 of table 46.
In formula I-D,
Table 76：Work as A=H, R8=R9=Cl, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46, representation compound
Numbering is 76-1---76-16, is corresponding in turn to the 1-16 of table 46.
Table 77：Work as A=H, R8=Cl, R9=CH3, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46, representativeization
Compound numbering is 77-1---77-16, is corresponding in turn to the 1-16 of table 46.
Table 78：Work as A=H, R8=CH3, R9=H, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46, representativeization
Compound numbering is 78-1---78-16, is corresponding in turn to the 1-16 of table 46.
Table 79：Work as A=H, R8=H, R9=CH3, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46, representativeization
Compound numbering is 79-1---79-16, is corresponding in turn to the 1-16 of table 46.
Table 80：Work as A=H, R8=H, R9=CN, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46, represent chemical combination
Thing numbering is 80-1---80-16, is corresponding in turn to the 1-16 of table 46.
Table 81：Work as A=H, R8=H, R9=CH2Cl, R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46, represent
Compound number is 81-1---81-16, is corresponding in turn to the 1-16 of table 46.
Table 82：Work as A=H, R8=R9=Cl, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 46, represent chemical combination
Thing numbering is 82-1---82-16, is corresponding in turn to the 1-16 of table 46.
Table 83：Work as A=H, R8=Cl, R9=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 46, represent
Compound number is 83-1---83-16, is corresponding in turn to the 1-16 of table 46.
Table 84：Work as A=H, R8=CH3, R9=H, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 46, representativeization
Compound numbering is 84-1---84-16, is corresponding in turn to the 1-16 of table 46.
Table 85：Work as A=H, R8=H, R9=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 46, representativeization
Compound numbering is 85-1---85-16, is corresponding in turn to the 1-16 of table 46.
Table 86：Work as A=H, R8=H, R9=CN, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 46, representativeization
Compound numbering is 86-1---86-16, is corresponding in turn to the 1-16 of table 46.
Table 87：Work as A=H, R8=H, R9=CH2Cl, R7During=Cl, substituent R1、R2、R3、R4、R5It is consistent with table 46, represent
Compound number is 87-1---87-16, is corresponding in turn to the 1-16 of table 46.
In formula I-E,
Table 88：Work as A=H, R8=R9=Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46, generation
Table compound number is 88-1---88-16, is corresponding in turn to the 1-16 of table 46.
Table 89：Work as A=H, R8=Cl, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 89-1---89-16, is corresponding in turn to the 1-16 of table 46.
Table 90：Work as A=H, R8=CH3, R9=H, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 90-1---90-16, is corresponding in turn to the 1-16 of table 46.
Table 91：Work as A=H, R8=H, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 91-1---91-16, is corresponding in turn to the 1-16 of table 46.
Table 92：Work as A=H, R8=H, R9=CN, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46,
Representation compound numbering is 92-1---92-16, is corresponding in turn to the 1-16 of table 46.
Table 93：Work as A=H, R8=H, R9=CH2Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 93-1---93-16, is corresponding in turn to the 1-16 of table 46.
Table 94：Work as A=H, R8=R9=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 94-1---94-16, is corresponding in turn to the 1-16 of table 46.
Table 95：Work as A=H, R8=R9=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 95-1---95-16, is corresponding in turn to the 1-16 of table 46.
Table 96：Work as A=H, R8=Cl, R9=CH3, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 96-1---96-16, is corresponding in turn to the 1-16 of table 46.
Table 97：Work as A=H, R8=CH3, R9=H, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 97-1---97-16, is corresponding in turn to the 1-16 of table 46.
Table 98：Work as A=H, R8=H, R9=CH3, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 98-1---98-16, is corresponding in turn to the 1-16 of table 46.
Table 99：Work as A=H, R8=H, R9=CN, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 99-1---99-16, is corresponding in turn to the 1-16 of table 46.
Table 100：Work as A=H, R8=H, R9=CH2Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table
46 is consistent, and representation compound numbering is 100-1---100-16, is corresponding in turn to the 1-16 of table 46.
Table 101：Work as A=H, R8=R9=Cl, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 101-1---101-16, is corresponding in turn to the 1-16 of table 46.
Table 102：Work as A=H, R8=R9=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 102-1---102-16, is corresponding in turn to the 1-16 of table 46.
In formula II-A,
Table 103：Work as A=H, R8=R9=Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46,
Representation compound numbering is 103-1---103-16, is corresponding in turn to the 1-16 of table 46.
Table 104：Work as A=H, R8=Cl, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 104-1---104-16, is corresponding in turn to the 1-16 of table 46.
Table 105：Work as A=H, R8=CH3, R9=H, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 105-1---105-16, is corresponding in turn to the 1-16 of table 46.
Table 106：Work as A=H, R8=H, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 106-1---106-16, is corresponding in turn to the 1-16 of table 46.
Table 107：Work as A=H, R8=H, R9=CN, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 107-1---107-16, is corresponding in turn to the 1-16 of table 46.
Table 108：Work as A=H, R8=H, R9=CH2Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 108-1---108-16, is corresponding in turn to the 1-16 of table 46.
Table 109：Work as A=H, R8=R9=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 109-1---109-16, is corresponding in turn to the 1-16 of table 46.
Table 110：Work as A=H, R8=R9=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 110-1---110-16, is corresponding in turn to the 1-16 of table 46.
Table 111：Work as A=H, R8=R9=Cl, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 111-1---111-16, is corresponding in turn to the 1-16 of table 46.
Table 112：Work as A=H, R8=R9=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 112-1---112-16, is corresponding in turn to the 1-16 of table 46.
In general formula III-A,
Table 113：Work as A=H, R8=R9=Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46,
Representation compound numbering is 113-1---113-16, is corresponding in turn to the 1-16 of table 46.
Table 114：Work as A=H, R8=Cl, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 114-1---114-16, is corresponding in turn to the 1-16 of table 46.
Table 115：Work as A=H, R8=CH3, R9=H, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 115-1---115-16, is corresponding in turn to the 1-16 of table 46.
Table 116：Work as A=H, R8=H, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 116-1---116-16, is corresponding in turn to the 1-16 of table 46.
Table 117：Work as A=H, R8=H, R9=CN, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 117-1---117-16, is corresponding in turn to the 1-16 of table 46.
Table 118：Work as A=H, R8=H, R9=CH2Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 118-1---118-16, is corresponding in turn to the 1-16 of table 46.
Table 119：Work as A=H, R8=R9=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 119-1---119-16, is corresponding in turn to the 1-16 of table 46.
Table 120：Work as A=H, R8=R9=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 120-1---120-16, is corresponding in turn to the 1-16 of table 46.
Table 121：Work as A=H, R8=R9=Cl, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 47 1
Cause, representation compound numbering is 121-1---121-16, is corresponding in turn to the 1-16 of table 46.
Table 122：Work as A=H, R8=R9=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table 47
Unanimously, representation compound numbering is 122-1---122-16, is corresponding in turn to the 1-16 of table 46.
In general formula III-B,
Table 123：Work as A=H, R8=R9=Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5It is consistent with table 46,
Representation compound numbering is 123-1---123-16, is corresponding in turn to the 1-16 of table 46.
Table 124：Work as A=H, R8=Cl, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 124-1---124-16, is corresponding in turn to the 1-16 of table 46.
Table 125：Work as A=H, R8=CH3, R9=H, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 125-1---125-16, is corresponding in turn to the 1-16 of table 46.
Table 126：Work as A=H, R8=H, R9=CH3, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 126-1---126-16, is corresponding in turn to the 1-16 of table 46.
Table 127：Work as A=H, R8=H, R9=CN, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 127-1---127-16, is corresponding in turn to the 1-16 of table 46.
Table 128：Work as A=H, R8=H, R9=CH2Cl, Ra=Rb=R7During=H, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 128-1---128-16, is corresponding in turn to the 1-16 of table 46.
Table 129：Work as A=H, R8=R9=Cl, Ra=Rb=H, R7During=Cl, substituent R1、R2、R3、R4、R5With table 47 1
Cause, representation compound numbering is 129-1---129-16, is corresponding in turn to the 1-16 of table 46.
Table 130：Work as A=H, R8=R9=Cl, Rb=R7=H, Ra=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 130-1---130-16, is corresponding in turn to the 1-16 of table 46.
Table 131：Work as A=H, R8=R9=Cl, R7=H, Ra=Rb=CH3When, substituent R1、R2、R3、R4、R5With table 46 1
Cause, representation compound numbering is 131-1---131-16, is corresponding in turn to the 1-16 of table 46.
Table 132：Work as A=H, R8=R9=Cl, Rb=H, Ra=CH3, R7During=Cl, substituent R1、R2、R3、R4、R5With table 46
Unanimously, representation compound numbering is 132-1---132-16, is corresponding in turn to the 1-16 of table 46.
Table 133：In formula I-A, work as R8=Cl, R9=Cl, R7=R1=R2=R3=R5During=H, R4=Cl, substituent A are shown in
Table 133, representation compound numbering is 133-1---133-140.
Table 133
Table 134：In formula I-A, work as R8=Cl, R9=Cl, R7=R1=R2=R3=R5=H, R4During=H, substituent A with
Table 133 is consistent, and representation compound numbering is 134-1---134-140, is corresponding in turn to the 1-140 of table 133.
Table 135：In formula I-A, work as R8=Cl, R9=Cl, R7=R1=R3=R5=H, R2=Cl, R4=CF3When, replace
Base A is consistent with table 133, and representation compound numbering is 135-1---135-140, is corresponding in turn to the 1-140 of table 133.
Table 136：In formula I-A, work as R8=Cl, R9=Cl, R7=R1=R2=R3=R5=H, R4=CF3When, substituent A
Consistent with table 133, representation compound numbering is 136-1---136-140, is corresponding in turn to the 1-140 of table 133.
Table 137：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R1=R2=R3=R5During=H, R4=Cl,
Substituent A is shown in Table 133, and representation compound numbering is 137-1---137-140, is corresponding in turn to the 1-140 of table 133.
Table 138：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R1=R2=R3=R5=H, R4During=H, take
Consistent with table 133 for base A, representation compound numbering is 138-1---138-140, according to the 1-140 for being corresponding in turn to table 133.
Table 139：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R1=R3=R5=H, R2=Cl, R4=CF3
When, substituent A is consistent with table 133, and representation compound numbering is 139-1---139-140, is corresponding in turn to the 1-140 of table 133.
Table 140：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R1=R2=R3=R5=H, R4=CF3When,
Substituent A is consistent with table 133, and representation compound numbering is 140-1---140-140, is corresponding in turn to the 1-140 of table 133.
Table 141：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R1=R2=R3=R5=H, R4During=F, take
Consistent with table 133 for base A, representation compound numbering is 141-1---141-140, is corresponding in turn to the 1-140 of table 133.
Table 142：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R1=R3=R5=H, R2=R4During=Cl,
Substituent A is consistent with table 133, and representation compound numbering is 142-1---142-140, is corresponding in turn to the 1-140 of table 133.
Table 143：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R2=R3=R4=R5=H, R1=CF3When,
Substituent A is consistent with table 133, and representation compound numbering is 143-1---143-140, is corresponding in turn to the 1-140 of table 133.
Table 144：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R2=R3=R4=R5=H, R1During=Cl,
Substituent A is consistent with table 133, and representation compound numbering is 144-1---144-140, is corresponding in turn to the 1-140 of table 133.
Table 145：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R1=R2=R3=R4=H, R5=CH3When,
Substituent A is consistent with table 133, and representation compound numbering is 145-1---145-140, is corresponding in turn to the 1-140 of table 133.
Table 146：In formula I-B, work as R8=Cl, R9=Cl, Ra=Rb=R7=R1=R2=R5=H, R3=R4During=F, take
Consistent with table 133 for base A, representation compound numbering is 146-1---146-140, is corresponding in turn to the 1-140 of table 133.
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
Compound of formula I method is prepared, except that replacing 6- chlorine apellagrins (M-1) to be changed to replacement 2- chloroisonicotinic acids initiation material
With replacement 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 in formula, each group is unless otherwise indicated fixed
It is adopted the same：
Intermediate H and L react in the basic conditions and obtain compound of Formula I.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine,
Feldalat NM, Sodium ethylate, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
Reaction carry out in suitable solvent, the optional tetrahydrofuran freely of suitable solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile,
Toluene, dimethylbenzene, benzene, N,N-dimethylformamide, N-Methyl pyrrolidone, dimethyl sulfoxide, acetone or butanone etc..
Reaction temperature can be in room temperature between solvent boiling point temperature, usually 20-100 DEG C.
Response time is 30 minutes to 20 hours, usual 1-10 hours.
Intermediate L portion is commercially available, it is also possible to prepare by known method, referring for example to document DE102005031348 or
It is prepared by the method for the descriptions such as CN102942565.
Intermediate H is different with X definition according to A, B, is divided into following three kinds of situations and prepares：
The first situation：
As A=H,
1) 5 carbon atoms of B=amide nitrogen atoms and hexa-atomic aromatic rings are joined directly together, referring to patent WO9948871,
WO2108649 Journal of organometallic chemistry,677(1-2),57-72；2003、CN101028598
Or Tetrahadron Letters, 53 (35), 4665-4668；It is prepared by the method described in 2012, or as follows
Prepare.
Intermediate H-A1 and H-A2 at suitable temperature, reacts 30 points in suitable solvent in the presence of suitable alkali
To 20 hours, usual 1-10 hours were obtained intermediate H-A3 to clock；H-A3 Jing zinc powder reductions are obtained intermediate H-A, this step operation
Method is referring to patent WO9948871, WO2108649.
Intermediate source is as follows：Intermediate H-A1 and H-A2 is commercially available, or conventionally prepares.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine,
Feldalat NM, Sodium ethylate, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
Reaction carry out in suitable solvent, the optional tetrahydrofuran freely of suitable solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile,
Toluene, dimethylbenzene, benzene, N,N-dimethylformamide, N-Methyl pyrrolidone, dimethyl sulfoxide, acetone or butanone etc..
Reaction temperature can be in room temperature between solvent boiling point temperature, usually 20-100 DEG C.
Response time is 30 minutes to 20 hours, usual 1-10 hours.
2) B=CRaRbWhen, described in referenced patent WO 2013111864, WO 2013089212 or WO 2013042139
Method prepare, it is as follows：
In formula, U is leaving group, is halogen or hydroxyl etc..
Intermediate H-B1 and H-B2 at suitable temperature, reacts 30 points in suitable solvent in the presence of suitable alkali
To 20 hours, usual 1-10 hours were obtained intermediate H-B3 to clock；H-B3 appropriate catalyst as and ammonia in the presence of it is hydrogenated
Reduction obtains intermediate H-B4；Concrete preparation is referred to document J.Am.Chem.Soc, and 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 in (1947)
The method of description 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-B1 and H-B2 is commercially available, or conventionally prepares.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine,
Feldalat NM, Sodium ethylate, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
Reaction carry out in suitable solvent, the optional tetrahydrofuran freely of suitable solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile,
Toluene, dimethylbenzene, benzene, N,N-dimethylformamide, N-Methyl pyrrolidone, dimethyl sulfoxide, acetone or butanone etc..
Reaction temperature can be in room temperature between solvent boiling point temperature, usually 20-100 DEG C.
Response time is 30 minutes to 20 hours, usual 1-10 hours.
3) B=-CH2CRaRbWhen, referring to the side described in patent WO9404527, US20110054173 or WO2011022
Prepared by method, as follows：
In formula, U is leaving group, is halogen or hydroxyl etc..
Intermediate H-C1 and H-C2 at suitable temperature, reacts 30 points in suitable solvent in the presence of suitable alkali
To 20 hours, usual 1-10 hours were obtained intermediate H-C3 to clock；H-C3 Jing red aluminium reducings are obtained H-C4, this step operation method
Referring to patent EP1840128；H-C4 is obtained H-C5 with thionyl chloride reaction, and this is normal experiment method；H-C5 is anti-with Cyanogran.
Should, H-C6 is obtained, 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], (10), 40-51, the method described in 2002 are obtained H-C7 by H-C7；Finally, H-C7 exists
Appropriate catalyst is such as and hydrogenated reduction obtains intermediate H-C in the presence of ammonia, and concrete preparation 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 the method described in (1947) carry out.Suitable catalyst is optional
From Raney's nickel, palladium carbon or platinum oxide etc..
Intermediate source is as follows：Intermediate H-C1 and H-C2 is commercially available, or conventionally prepares.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine,
Feldalat NM, Sodium ethylate, sodium hydride, potassium tert-butoxide or sodium tert-butoxide etc..
Reaction carry out in suitable solvent, the optional tetrahydrofuran freely of suitable solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile,
Toluene, dimethylbenzene, benzene, N,N-dimethylformamide, N-Methyl pyrrolidone, dimethyl sulfoxide, acetone or butanone etc..
Reaction temperature can be in room temperature between solvent boiling point temperature, usually 20-100 DEG C.
Response time is 30 minutes to 20 hours, usual 1-10 hours.
4) B=-CH2CRaRbCRaRbWhen, preparation method is as follows：
H-D1 is prepared by H-C7 and refers to Synthesis, (9), 727-9；1983 or Tetrahedron Letters, 39
(51),9455-9456；Method described in 1998 is carried out；H-D2 methods are prepared with corresponding steps during B=-CH2- by H-D1.
Second situation：As A ≠ H, be obtained for raw material by the intermediate of A=H, concrete operations referring to
Method described in WO2004093800A is carried out.
The third situation：Method as A=O or S, described in preparation method referenced patent WO 2012075917.
Although some compounds disclosed in formula I, II or Ш compound of the present invention and prior art belong to different thiophene
Azole compounds, but architectural feature still suffer from it is dramatically different.And the change of the present invention is caused due to the difference in these structures
Compound has preferably sterilization and/or pesticide and miticide actility, and can sterilize under the dosage of very little and/or Insecticiding-miticiding work
Property.
Formula I, II or III compound shows excellent activity to agricultural or the various pathogenic bacterias in other field, to evil
Insect pest demodicid mite also shows that preferable activity.Therefore, technical scheme also includes formula I, II or III compound in agricultural
Or be used as to prepare the purposes of antibacterial, 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 III compound can be used to prevent and treat following disease：Oomycetes diseases, such as downy mildew (cucumber downy mildew,
Oilseed rape downy mildew, downy mildew, Radix Betae downy mildew, downy mildew of sugarcane, tobacco downy mildew, Semen Pisi sativi downy mildew, Fructus Luffae downy mildew,
Fructus Benincasae downy mildew, muskmelon downy mildew, cabbage downy mildew, downy mildew of spinach, Radix Raphani downy mildew, downy mildew of garpe, onion mildew),
White rust (white rust of colza, cabbage white blister), damping off (Brassica campestris L damping off, Tobacco seedling diseases, Fructus Lycopersici esculenti damping off, Fructus Capsici
Damping off, Fructus Solani melongenae damping off, Fructus Cucumidis sativi damping off, cotton Seedling damping off), (Fructus Capsici pythium rot, Fructus Luffae pythium rot, Fructus Benincasae are continuous for pythium rot
Maize ear rot), epidemic disease (Semen Viciae fabae epidemic disease, Cucumber Blight, Fructus Cucurbitae moschatae epidemic disease, Fructus Benincasae epidemic disease, Citrullus vulgariss epidemic disease, muskmelon blight, capsicum epidemic disease, fragrant-flowered garlic
Dish epidemic disease, Bulbus Allii epidemic disease, Cotton blight), late blight (late blight of potato, tomato late blight) etc.；Fungi Imperfecti disease, it is such as withered
(Rhizoma Dioscoreae esculentae droop, cotton wilt, Semen Sesami droop, Semen Ricini droop, tomato wilt, Kidney bean droop, Fructus Cucumidis sativi wither disease
Disease, Fructus Luffae droop, Fructus Cucurbitae moschatae droop, Fructus Benincasae droop, watermelon blight, Muskmelon Fusarium wilt, capsicum wilt, Semen Viciae fabae are withered
Disease, Brassica campestris L droop, soybean Fusariuming disease), root rot (Fusarium solani, Fructus Solani melongenae root rot, Kidney bean root rot, cucumber root rot,
Fructus Momordicae charantiae root rot, cotton black root rot, root rot of Vicia faba), damping-off (cotton seedling blight, Semen Sesami damping-off, Fructus Capsici damping-off, Huang
Melon damping-off, Chinese cabbage damping-off), anthrax (anthracnose of sorghum, cotton anthracnose, ambary anthrax, Corchorus olitorius L. anthrax, Caulis et Folium Lini
Anthrax, anthracnose of tobacco, Mulberry anthrax, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, Fructus Momordicae charantiae charcoal
Cellulitis disease, Cucurbita pepo L. anthrax, Fructus Benincasae anthrax, watermelon anthrax, Fructus Melo anthrax, Fructus Litchi anthrax), verticillium wilt (cotton yellow
Wither disease, Helianthi verticillium wilt, Fructus Lycopersici esculenti verticillium wilt, Fructus Capsici verticillium wilt, eggplant verticillium wilt), scab (Cucurbita pepo L. scab, Fructus Benincasae
Scab, Fructus Melo scab), gray mold (cotton boll gray mold, ambary gray mold, graw mold of tomato, Botrytis cinerea, Kidney bean ash
Mildew, Herba Apii graveolentis gray mold, Herba Spinaciae gray mold, Fructus actinidiae chinensiss gray mold), (Cotton Gossypii brown spot, Corchorus olitorius L. brown spot, Radix Betae are brown for brown spot
Pinta, the cercospora brown spot of peanut, Fructus Capsici brown spot, Fructus Benincasae brown spot, Semen sojae atricolor brown spot, septorial brown spot of sunflower, Semen Pisi sativi brown spot, Semen Viciae fabae
Brown spot), melasma (Caulis et Folium Lini vacation melasma, alternaria stem rot of colza, Semen Sesami melasma, Helianthi melasma, Semen Ricini melasma, kind
Eggplant melasma, Fructus Capsici melasma, Fructus Solani melongenae melasma, Kidney bean melasma, Fructus Cucumidis sativi melasma, Herba Apii graveolentis melasma, carrot black rot,
Black rot of carrot, melanose or canker of apple, the cercospora black spot of peanut), spot blight (spotted wilt of tomato, Fructus Capsici spot blight, celery septoria disease),
Early blight (early blight of tomato, Fructus Capsici early blight, Fructus Solani melongenae early blight, target, early blight of celery), ring spot (Semen sojae atricolor
Ring spot, Semen Sesami ring spot, Kidney bean ring spot), leaf blight (Semen Sesami leaf blight, Folium Helianthi rot, Citrullus vulgariss leaf blight, Fructus Melo
Leaf blight), base rot disease (Fructus Lycopersici esculenti base rot disease, Kidney bean base rot disease), and other (Helminthosporium carbonum, ambary waist folding disease, rice blasts
Disease, the black sheath disease of chestnut, Caulis Sacchari sinensis eye spot, cotton boll aspergillosis, Semen arachidis hypogaeae crown rot, Semen sojae atricolor stem wilt, Semen sojae atricolor diplostomiasis, the big speckle of Fructus Melo
The red leaf spot of disease, Peanut Web Blotch Disease, tea, pepper white star disease, Fructus Benincasae leaf spot, Herba Apii graveolentis black rot, Herba Spinaciae heartrot, ambary leaf mold
Disease, ambary spot disease, Corchorus olitorius L. stem blight, purple spot of soybean, Alternaria sesami, Semen Ricini graywall, dark brown leaf spot, Fructus Solani melongenae are brown
Color circle star disease, Kidney bean red spot disease, Fructus Momordicae charantiae leukoderma, Citrullus vulgariss spot disease, Corchorus olitorius L. withered rotten disease, Radix Helianthi stem rot, Kidney bean charcoal are rotten
Disease, Semen sojae atricolor target spot disease, Fructus Solani melongenae rod spore leaf spot, Leaf Spot Caused by Corynespora cassiicola on Cucumber, leaf muld of tomato, Fructus Solani melongenae leaf mold, Semen Viciae fabae reddish macules etc.)
Deng；Load fungus diseases, such as rust are (stripe rust of wheat, the stem rust of wheat, wheat leaf rust, Peanut Rust, rust of sunflower, sweet
Sugarcane rust, Folium Allii tuberosi rust, rust of onion, chestnut rust, soybean rust), smut (maize head smut, corn smut, Sorghum vulgare Pers. 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 diseases etc.) etc.；Ascomycetess disease, such as powdery mildew (wheat powdery mildew, Brassica campestris L white lead
Disease, Semen Sesami powdery mildew, Helianthi powdery mildew, beet powdery mildew, Fructus Solani melongenae powdery mildew, powdery mildew of pea, Fructus Luffae powdery mildew, Fructus Cucurbitae moschatae are white
Powder disease, Pumpkin powdery mildew, Fructus Benincasae powdery mildew, melon powdery mildew, uncinula necator, Semen Viciae fabae powdery mildew), sclerotiniose (Caulis et Folium Lini bacterium
Core disease, sclerotinia rot of colza, soybean sclerotinia crown rot, Semen arachidis hypogaeae sclerotiniose, Nicotiana tabacum L. sclerotiniose, Fructus Capsici sclerotiniose, Fructus Solani melongenae sclerotiniose, Kidney bean bacterium
Core disease, Semen Pisi sativi sclerotiniose, cucumber timberrot, Fructus Momordicae charantiae sclerotiniose, wax gourd sclerotinia, Citrullus vulgariss sclerotiniose, Herba Apii graveolentis sclerotiniose), black star
Sick (scab of apple, pear scab) etc..Especially, to corn rust, rice blast, gray mold of cucumber and Fructus Cucumidis sativi downy mildew
Disease, still has good prevention effect at lower doses.
Formula I, II or III compound can be used to prevent and treat following insect pest：Diamondback moth, mythimna separata, aphid, Tetranychus cinnabarinus, compared with
Still there is under low dosage good prevention effect.
Due to its positive characteristic, above-claimed cpd is advantageously used for the important crop of protecting agriculture and horticulture, family
Raise and breeding stock, and the environment that the mankind often go avoids pathogenic bacteria, 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 of pre- protection
Thing, the type of harmful organism, gradient of infection, weather conditions, application method, the dosage form for adopting.
The compound dosage of 10 grams -5 kilograms of per hectare can provide sufficiently preventing and treating.
Present invention additionally comprises using formula I, II or III compound as the sterilization of active component, insecticide acaricide composition.Should
In sterilization, insecticide acaricide composition, the weight percentage of active component is between 0.5-99%.The sterilization, Insecticiding-miticiding combination
Also including acceptable carrier in agricultural, forestry, health in thing.
The compositionss of the present invention can be applied in the form of preparation.Formula I, II or III compound is dissolved as active component
Or in being scattered in carrier or preparation is configured to so as to more readily dispersible when using as sterilization, parasite killing.For example：These chemicals
Wettable powder, oil suspending agent, aqueous suspension, aqueous emulsion, water preparation or cream etc. can be made into.In these compositionss, at least add
A kind of liquid or solid carrier, 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
Compositionss are imposed on described pathogenic bacteria or its somatomedin.The more suitable effective amount for generally selecting is 10 grams of per hectare to 1000
Gram, preferred effective dose is 20 grams to 500 grams of per hectare.
For some applications, for example agriculturally can the sterilization of the present invention, add in insecticide acaricide composition it is a kind of or
Various other antibacterial, 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.
Specific 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, raw materials used to be commercially available)
Synthetic example
Embodiment 1：The preparation of intermediate 6- (4- chlorophenoxies) -3- aminopyridines
1) preparation of 6- (4- chlorophenoxies) -3- nitropyridines
10.0g (7.8mmol) parachlorophenol is added in the there-necked flask of 250mL, adds 50mL DMF to dissolve which, room
The lower stirring 10min of temperature, is subsequently adding 2.3g (9.5mmol) NaH, continues 3h is stirred at room temperature.After the completion of to be mixed, add
12.3g (7.8mmol) 2- chloro-5-nitropyridines, are to slowly warm up to 80 DEG C, after the completion of TLC question responses (about 3h), are cooled to room
Temperature, adds 1000mL water, has a large amount of solids to separate out, and sucking filtration is dried, obtains pale solid product 16.8g, yield：94%.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):7.02(d,1H),7.20(d,2H),7.60(d,2H),.8.41
(dd,1H),8.90(d,1H).
2) preparation of 6- (4- chlorophenoxies) -3- aminopyridines
2.0g (8.0mmol) 6- (4- chlorophenoxies) -3- nitropyridines are added in the there-necked flask of 150mL, are added
20mLAcOH, is then dividedly in some parts 1.37g (2.1mmol) zinc powder, and 3h is reacted under room temperature, after the completion of TLC question responses, outstanding to be evaporated off
Solvent, Deca NaOH (5%) aqueous solution are adjusted to the aobvious neutrality of PH, are extracted with the ethyl acetate of 3 × 20mL, and organic faciess are with anhydrous
MgSO4It is dried, after revolving, Jing column chromatographies obtain light red oil product 1.3g, yield 81%.
Embodiment 2：The preparation of compound 4-7
0.5g (2.0mmol) 6- (4- chlorophenoxies) -3- aminopyridines are added in the there-necked flask of 100mL, are added
20mL acetonitriles and 0.2g (2.4mmol) triethylamine, are then dividedly in some parts 0.5g (2.3mmol) 3,4- dichloro isothiazolo acyl chlorides, rise
Warm back flow reaction, after the completion of TLC question responses, revolving removes solvent, and Jing column chromatographies obtain faint yellow solid product 0.7g, i.e. chemical combination
Thing 4-7.Yield 86%.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):7.01(d,1H), 7.09(d,2H),
7.37(d,2H),8.16(dd,1H),8.31(s,1H),8.47(bs,1H).
Embodiment 3：The preparation of intermediate (6- (4- 4-trifluoromethylphenopendants) pyridin-3-yl) methylamine
1) preparation of 6- (4- 4-trifluoromethylphenopendants) nicotinic acid nitrile
To in the 350ml DMF solution of 32.4g (0.2mol) p-trifluoromethyl-phenol, it is dividedly in some parts
70% sodium hydride 103g (3.0mol), is stirred at room temperature reaction 4h, is then dividedly in some parts 27.7g (0.2mol) 6- chlorine thereto
Nicotinic acid nitrile, finishes, and reactant mixture is warming up to 100 DEG C of reaction 10h, and TLC is monitored after completion of the reaction, reactant liquor is poured into water, second
Acetoacetic ester is extracted, and organic faciess Jing washings successively, saturated salt washing are dried, filter, precipitation, after residue cooled and solidified, filter,
Petroleum ether, obtains brown solid 42.0g, i.e. 6- (4- 4-trifluoromethylphenopendants) nicotinic acid nitrile after drying.
2) preparation of (6- (4- 4-trifluoromethylphenopendants) pyridin-3-yl) methylamine
By 2.64g (0.01mol) 6- (4- 4-trifluoromethylphenopendants) nicotinic acid nitrile, Raney nickel (1.0g), 25% ammonia 10ml and
The mixture of ethanol 50ml compositions stirring reaction 3-15h under hydrogen atmosphere, room temperature, TLC are monitored after completion of the reaction, filter Raney
Nickel, removes solvent under reduced pressure and obtains pale green viscous shape liquid 2.6g, yield 95.0%.Colorless oil.
Embodiment 4：The preparation of compound 16-22
0.5g (2.0mmol) (6- (4- 4-trifluoromethylphenopendants) pyridin-3-yl) methylamine is added to into the there-necked flask of 100mL
In, 20mL acetonitriles and 0.2g (2.4mmol) triethylamine are added, bis- chloroisothiazoles of 0.5g (2.3mmol) 3,4- are then dividedly in some parts
Acyl chlorides, temperature rising reflux reaction, after the completion of TLC question responses, revolving removes solvent, and Jing column chromatographies obtain faint yellow solid product
0.7g, i.e. compound 16-22, yellow solid, 123.8 DEG C of fusing point.Yield 86%.1H-NMR (300MHz, internal standard TMS, solvent
CDCl3)δ(ppm):4.63(d,2H),7.00(d,1H),7.26(d,3H),7.66(d,2H),87.79(dd,1H),18(d,
1H).
Embodiment 5：The preparation of compound 46-2
To 0.3g (1.0mmol) 2- (6- (4- chlorophenoxies) pyridin-3-yl) ethamine (concrete synthetic method referring to
WO2014063642A1 in 10ml acetonitrile solutions), triethylamine 0.2g (1.5mmol) is added, stirring is lower to add 3,4- dichloros different
Thiazole acyl chlorides 0.3g (1.2mmol), is warming up to 80 DEG C of reaction 2h after adding, TLC is monitored after completion of the reaction, precipitation, residue post
(eluant is ethyl acetate and petroleum ether (boiling range 60-90 DEG C) to chromatography, and volume ratio is 1：2) purification obtains product 0.4g, i.e. chemical combination
Thing 46-2, yellow oily liquid.Yield 91.0%, colorless oil.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ
(ppm):3.10(t,2H),3.85(q,2H),6.91(bs,1H),6.99(t,1H),7.05(dd,2H),7.33(d,2H),
7.57(d,1H),8.08(d,1H).
Embodiment 6：The preparation of intermediate 4- (4- amino-benzene oxygens) -3- fluorobenzonitriles
1) preparation of the fluoro- 4- of 3- (4-nitrophenoxy) cyanophenyl
10.8g (78mmol) paranitrophenol is added in the there-necked flask of 250mL, adds 50mL DMF to dissolve which,
10min is stirred under room temperature, 2.3g (95mmol) NaH is subsequently adding, is continued 3h is stirred at room temperature.After the completion of to be mixed, add
10.8g (78mmol) 3,4- difluorobenzonilyiles, are to slowly warm up to 80 DEG C, after the completion of TLC question responses (about 3h), are cooled to room temperature, plus
Enter 1000mL water, there are a large amount of solids to separate out, sucking filtration is dried, obtains gray solid product 18.5g, yield：92%.1H-NMR
(300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.71(bs,1H),6.72(d,2H),6.89(m,3H),.7.30(dd,
1H),7.44(d,1H).
2) preparation of intermediate 4- (4- amino-benzene oxygens) -3- fluorobenzonitriles
2.1g (8.0mmol) 3- fluoro- 4- (4-nitrophenoxy) cyanophenyl is added in the there-necked flask of 150mL, is added
20mLAcOH, is then dividedly in some parts 1.37g (2.1mmol) zinc powder, and 3h is reacted under room temperature, after the completion of TLC question responses, outstanding to be evaporated off
Solvent, Deca NaOH (5%) aqueous solution are adjusted to the aobvious neutrality of PH, are extracted with the ethyl acetate of 3 × 20mL, and organic faciess are with anhydrous
MgSO4It is dried, after revolving, Jing column chromatographies obtain light red oil product 1.5g, yield 83%.
Embodiment 7：The preparation of compound 76-13
To in the 10ml acetonitrile solutions of 0.2g (1.0mmol) 4- (4- amino-benzene oxygens) -3- fluorobenzonitriles, triethylamine is added
0.2g (1.5mmol), stirring is lower to add 3,4- dichloros isothiazolo acyl chloride 0.3g (1.2mmol), and 80 DEG C of reactions are warming up to after adding
2h, TLC are monitored after completion of the reaction, precipitation, residue column chromatography (eluant is ethyl acetate and petroleum ether (boiling range 60-90 DEG C),
Volume ratio is 1：2) purification obtains product 0.3g, i.e. compound 76-13, yellow solid, 122.6 DEG C.Yield 91.0%, colorless oil
Thing.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):7.01(t,1H),7.11(d,2H),7.41(d,2H),
7.69(d,2H),8.55(bs,1H).
Embodiment 8：The preparation of 1- (4- (2- chloro- 4- (trifluoromethyl) phenoxy groups) phenyl) ethamine
1) preparation of 1- (4- (2- chloro- 4- (trifluoromethyl) phenoxy groups) phenyl) ethyl ketone
To in the 250ml DMF solution of the chloro- 4- trifloro methyl phenols of 19.6g (0.1mol) 2-, in batches
70% sodium hydride 103g (3.0mol) is added, reaction 4h is stirred at room temperature, 30.8g (0.2mol) is then dividedly in some parts thereto
4- chloro-acetophenones, finish, and reactant mixture is warming up to 100 DEG C of reaction 10h, and TLC is monitored after completion of the reaction, reactant liquor is poured into
In water, ethyl acetate extraction, organic faciess Jing washings successively, saturated salt washing are dried, filter, precipitation, residue cooled and solidified
Afterwards, filter, petroleum ether, after drying, obtain brown solid 41.0g, i.e. 1- (4- (2- chloro- 4- (trifluoromethyl) phenoxy groups) benzene
Base) ethyl ketone.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):2.48(s,3H),6.75(d,1H),7.01(d,
2H),7.38(d,1H),7.48(d,2H),7.95(d,2H).
2) preparation of 1- (4- (2- chloro- 4- (trifluoromethyl) phenoxy groups) phenyl) ethamine
To the 10ml methanol solutions of 0.3g (1.0mmol) 1- (4- (2- chloro- 4- (trifluoromethyl) phenoxy groups) phenyl) ethyl ketone
In, Ammoniom-Acetate 0.4g (5mmol) is added, stirring under ice bath adds NaBH3CN 0.3g (5mmol), add anti-under the conditions of rear room temperature
8h, TLC is answered to monitor after completion of the reaction, precipitation, (eluant is ethyl acetate and petroleum ether (boiling range 60-90 to residue column chromatography
DEG C), volume ratio is 1：1) purification obtains product 0.2g, colorless oil.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ
(ppm):,1.36(s,3H),3.98(q,1H),6.71(d,1H),6.78(d,2H),7.26(d,2H),7.29(d,1H),7.39
(d,1H).
Embodiment 9：The preparation of compound 95-12
To the 10ml acetonitrile solutions of 0.3g (1.0mmol) 1- (4- (2- chloro- 4- (trifluoromethyl) phenoxy groups) phenyl) ethamine
In, triethylamine 0.2g (1.5mmol) is added, stirring is lower to add 3,4- dichloros isothiazolo acyl chloride 0.3g (1.2mmol), rises after adding
Temperature is monitored after completion of the reaction to 80 DEG C of reaction 2h, TLC, precipitation, and (eluant is ethyl acetate and petroleum ether to residue column chromatography
(boiling range 60-90 DEG C), volume ratio are 1：2) purification obtains product 0.4g, i.e. compound 95-12, white solid, 98.6 DEG C.Yield
91.0%, colorless oil.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):1.60(s,3H),5.29(q,
1H),6.93(d,1H),7.03(d,2H),7.09(d,3H),7.72(d,1H),8.21(bs,1H).
Embodiment 10：The preparation of intermediate (2- (3- 4-trifluoromethylphenopendants) pyridin-3-yl) methylamine
1) preparation of 2- (3- 4-trifluoromethylphenopendants) nicotinic acid nitrile
To in the 350ml DMF solution of 32.4g (0.2mol) m-trifluoromethyl phenol, it is dividedly in some parts
70% sodium hydride 103g (3.0mol), is stirred at room temperature reaction 4h, is then dividedly in some parts 27.7g (0.2mol) 2- chlorine thereto
Nicotinic acid nitrile, finishes, and reactant mixture is warming up to 100 DEG C of reaction 10h, and TLC is monitored after completion of the reaction, reactant liquor is poured into water, second
Acetoacetic ester is extracted, and organic faciess Jing washings successively, saturated salt washing are dried, filter, precipitation, after residue cooled and solidified, filter,
Petroleum ether, obtains brown solid 42.0g, i.e. 2- (3- 4-trifluoromethylphenopendants) nicotinic acid nitrile after drying.
2) preparation of (2- (3- 4-trifluoromethylphenopendants) pyridin-3-yl) methylamine
By 2.64g (0.01mol) 2- (3- 4-trifluoromethylphenopendants) nicotinic acid nitrile, Raney nickel (1.0g), 25% ammonia 10ml and
The mixture of ethanol 50ml compositions stirring reaction 3-15h under hydrogen atmosphere, room temperature, TLC are monitored after completion of the reaction, filter Raney
Nickel, removes solvent under reduced pressure and obtains pale green viscous shape liquid 2.6g, yield 95.0%.Colorless oil.
Embodiment 11：The preparation of compound 113-8
0.5g (2.0mmol) (2- (3- 4-trifluoromethylphenopendants) pyridin-3-yl) methylamine is added to into the there-necked flask of 100mL
In, 20mL acetonitriles and 0.2g (2.4mmol) triethylamine are added, bis- chloroisothiazoles of 0.5g (2.3mmol) 3,4- are then dividedly in some parts
Acyl chlorides, temperature rising reflux reaction, after the completion of TLC question responses, revolving removes solvent, and Jing column chromatographies obtain faint yellow solid product
0.7g, i.e. compound 113-8, white solid, 105.7 DEG C.Yield 86%.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ
(ppm):4.60(d,2H),7.02(d,1H),7.27(d,3H),7.68(d,2H),7.80(dd,1H),8.17(d,1H).
Embodiment 12：The preparation of intermediate 2- (6- (4- chlorophenoxies) pyridine -2- bases) ethamine
1) preparation of 2- (4- chlorophenoxies) methyl nicotinate
To in the 350ml DMF solution of 25.6g (0.2mol) parachlorophenol, 70% is dividedly in some parts
Sodium hydride 103g (3.0mol), is stirred at room temperature reaction 4h, is then dividedly in some parts 34.2g (0.2mol) 2- chlorine apellagrin first thereto
Ester, finishes, and reactant mixture is warming up to 100 DEG C of reaction 10h, and TLC is monitored after completion of the reaction, reactant liquor is poured into water, acetic acid
Ethyl ester is extracted, and organic faciess Jing washings successively, saturated salt washing are dried, filter, precipitation, after residue cooled and solidified, filter, 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) preparation of (2- (4- chlorophenoxies) pyridin-3-yl) methanol
At 0 DEG C, in the 500ml anhydrous ether solutions of 52.6g (0.2mol) 2- (4- chlorophenoxies) methyl nicotinate, drop
Red aluminum toluene solution 74.5g (0.24mol) for plus 65%, finishes, and reaction 4h is stirred at room temperature, then at 0 DEG C, drips thereto
Plus 10% sodium hydroxide solution for preparing in advance, until reactant mixture becomes clarification, then heat to 35 DEG C of reactions 2h, TLC
Monitoring after completion of the reaction, reactant liquor is poured into water, toluene extraction, and organic faciess Jing washings successively, saturated salt washing are dried, mistake
Filter, precipitation, (eluant is ethyl acetate and petroleum ether (boiling range 60-90 DEG C) to residue column chromatography, and volume ratio is 1:3) purification is obtained
Product 42.2g, i.e. (2- (4- chlorophenoxies) pyridin-3-yl) methanol.Brown solid.Fusing point：95.1℃.1H-NMR (300MHz,
Internal standard 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) preparation of 3- chloromethyls -2- (4- chlorophenoxies) pyridine
At 0 DEG C, the 350ml dichloromethane to 23.5g (0.1mol) (6- (4- chlorophenoxies) pyridine -2- bases) methanol is molten
In liquid, Deca 17.9g (0.2mol) thionyl chloride is finished, and reaction 4h is stirred at room temperature, and TLC is monitored after completion of the reaction, and decompression is steamed
Go out excessive thionyl chloride, residue adds water, ethyl acetate extraction, organic faciess Jing washings successively, saturated sodium bicarbonate are washed, saturation
Salt is washed, and is dried, and is filtered, and precipitation obtains product 22.8g, i.e. 3- chloromethyls -2- (4- chlorophenoxies) pyridine.Faint yellow solid.It is molten
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) preparation of 2- (2- (4- chlorophenoxies) pyridin-3-yl) acetonitrile
At 40 DEG C, 2.7g (55mmol) Cyanogran. is dissolved in 300ml dimethyl sulfoxide, is then added thereto to
13.9g (50mmol) 6- chloromethyl -2- (4- chlorophenoxies) pyridines, add the 18- crown-s 6 of catalytic amount, and reactant mixture is warming up to
80 DEG C of reaction 2h, TLC are monitored after completion of the reaction, reactant liquor are poured into water, toluene extraction, organic faciess Jing washings successively, saturation
Salt is washed, and is dried, and is filtered, precipitation, and (eluant is ethyl acetate and petroleum ether (boiling range 60-90 DEG C), volume to residue column chromatography
Than for 1:3) purification obtains product 11.2g, i.e. 2- (2- (4- chlorophenoxies) pyridin-3-yl) acetonitrile.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) preparation of 2- (2- (4- chlorophenoxies) pyridin-3-yl) ethamine
By 2.4g (0.01mol) 2- (2- (4- chlorophenoxies) pyridin-3-yl) acetonitrile, Raney nickel (1.0g), 25% ammonia
The mixture of 10ml and ethanol 50ml compositions stirring reaction 3-15h under hydrogen atmosphere, room temperature, TLC are monitored after completion of the reaction, are filtered
Raney nickel, removes solvent under reduced pressure and obtains pale green viscous shape liquid 2.3g, yield 95.0%.Light green oil.1H-NMR
(300MHz, internal standard TMS, solvent C DCl3)δ(ppm):1.46(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 13：The preparation of compound 123-2
To in the 10ml acetonitrile solutions of 0.3g (1.0mmol) 2- (2- (4- chlorophenoxies) pyridin-3-yl) ethamine, three are added
Ethamine 0.2g (1.5mmol), stirring is lower to add 3,4- dichloros isothiazolo acyl chloride 0.3g (1.2mmol), and 80 DEG C are warming up to after adding
Reaction 2h, TLC are monitored after completion of the reaction, precipitation, and (eluant is ethyl acetate and petroleum ether (boiling range 60-90 to residue column chromatography
DEG C), volume ratio is 1：2) purification obtains product 0.4g, i.e. compound 123-2, white solid, 113.6 DEG C.Yield 91.0%, it is colourless
Grease.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.08(t,2H),3.86(q,2H),6.91(bs,
1H),6.99(t,1H),7.04(d,2H),7.35(d,2H),7.59(d,1H),8.06(d,1H).
Embodiment 14：The preparation of intermediate 2- (4- (4- chlorophenoxies) pyridin-4-yl) ethamine
1) preparation of 2- (4- chlorophenoxies) iso methyl nicotinate
To in the 350ml DMF solution of 25.6g (0.2mol) parachlorophenol, 70% is dividedly in some parts
Sodium hydride 103g (3.0mol), is stirred at room temperature reaction 4h, is then dividedly in some parts 34.2g (0.2mol) 2- chloroisonicotinic acids thereto
Methyl ester, finishes, and reactant mixture is warming up to 100 DEG C of reaction 10h, and TLC is monitored after completion of the reaction, reactant liquor is poured into water, second
Acetoacetic ester is extracted, and organic faciess Jing washings successively, saturated salt washing are dried, filter, precipitation, after residue cooled and solidified, filter,
Petroleum ether, 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) preparation of (2- (4- chlorophenoxies) pyridin-4-yl) methanol
At 0 DEG C, in the 500ml anhydrous ether solutions of 52.6g (0.2mol) 2- (4- chlorophenoxies) iso methyl nicotinate,
Red aluminum toluene solution 74.5g (0.24mol) of Deca 65%, finishes, and reaction 4h is stirred at room temperature, then at 0 DEG C, thereto
10% sodium hydroxide solution that Deca is prepared in advance, until reactant mixture becomes clarification, then heats to 35 DEG C of reaction 2h,
TLC is monitored after completion of the reaction, and reactant liquor is poured into water, toluene extraction, and organic faciess Jing washings successively, saturated salt washing are dried,
Filter, precipitation, (eluant is ethyl acetate and petroleum ether (boiling range 60-90 DEG C) to residue column chromatography, and volume ratio is 1：3) purification
Obtain product 42.2g, i.e. (2- (4- chlorophenoxies) pyridin-4-yl) methanol.Yellow liquid.1(300MHz, internal standard TMS are molten for H-NMR
Agent CDCl3)δ(ppm):3.95(bs,1H),4.70(s,2H),6.87(d,1H),6.98(d,1H),7.14(d,2H),7.34
(d,2H),8.11(d,1H).
3) preparation of 4- chloromethyls -2- (4- chlorophenoxies) pyridine
At 0 DEG C, the 350ml dichloromethane to 23.5g (0.1mol) (2- (4- chlorophenoxies) pyridin-4-yl) methanol is molten
In liquid, Deca 17.9g (0.15mol) thionyl chloride is finished, and reaction 4h is stirred at room temperature, and TLC is monitored after completion of the reaction, decompression
Excessive thionyl chloride is steamed, residue adds water, ethyl acetate extraction, organic faciess Jing washings successively, saturated sodium bicarbonate are washed, satisfied
Wash with salt, be dried, filter, precipitation obtains product 22.8g, i.e. 4- chloromethyls -2- (4- chlorophenoxies) pyridine.White solid.
Fusing 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) preparation of 2- (2- (4- chlorophenoxies) pyridin-4-yl) acetonitrile
At 40 DEG C, 2.7g (55mmol) Cyanogran. is dissolved in 300ml dimethyl sulfoxide, is then added thereto to
13.9g (50mmol) 4- chloromethyl -2- (4- chlorophenoxies) pyridines, add the 18- crown-s 6 of catalytic amount, and reactant mixture is warming up to
80 DEG C of reaction 2h, TLC are monitored after completion of the reaction, reactant liquor are poured into water, toluene extraction, organic faciess Jing washings successively, saturation
Salt is washed, and is dried, and is filtered, precipitation, and (eluant is ethyl acetate and petroleum ether (boiling range 60-90 DEG C), volume to residue column chromatography
Than for 1：3) purification obtains product 11.2g, i.e. 2- (2- (4- chlorophenoxies) pyridin-4-yl) acetonitrile.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- (preparations of 2- (4- chlorophenoxy pyridin-4-yls) ethamine
By 2.4g (0.01mol) 2- (2- (4- chlorophenoxies) pyridin-4-yl) acetonitrile, Raney nickel (1.0g), 25% ammonia
The mixture of 10ml and ethanol 50ml compositions stirring reaction 3-15h under hydrogen atmosphere, room temperature, TLC are monitored after completion of the reaction, are filtered
Raney nickel, removes solvent under reduced pressure and obtains rufous viscous liquid 2.3g, yield 95.0%.Brown oil.1H-NMR
(300MHz, internal standard TMS, solvent C DCl3)δ(ppm):1.46(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 15：The preparation of compound 103-2
To in the 10ml acetonitrile solutions of 0.3g (1.0mmol) 2- (2- (4- chlorophenoxies) pyridin-4-yl) ethamine, three are added
Ethamine 0.2g (1.5mmol), stirring is lower to add 3,4- dichloros isothiazolo acyl chloride 0.3g (1.2mmol), and 80 DEG C are warming up to after adding
Reaction 2h, TLC are monitored after completion of the reaction, precipitation, and (eluant is ethyl acetate and petroleum ether (boiling range 60-90 to residue column chromatography
DEG C), volume ratio is 1：2) purification obtains product 0.4g, i.e. compound 103-2, yellow oily liquid.Yield 91.0%, colorless oil
Thing.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):3.07(t,2H),3.85(q,2H),6.90(bs,1H),
6.96(t,1H),7.04(d,2H),7.34(d,2H),7.61(d,1H),8.07(d,1H).
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：
4-7 (pink solid, 124.0 DEG C)：δ7.01(d,1H),7.09(d,2H),7.37(d,2H),8.16(dd,1H),
8.31(s,1H),8.47(bs,1H).
16-1 (yellow solid, 102.7 DEG C)：δ4.63(d,2H),7.13(t,1H),7.22(t,1H),7.41(d,2H),
7.73(dd,1H),8.19(d,1H).
16-6 (yellow oily liquid)：δ4.62(d,2H),6.94(d,1H),7.06(d,1H),7.35(d,2H),7.40
(d,2H),7.74(d,1H),8.16(d,1H).
16-22 (white solid, 118.9 DEG C)：δ4.63(d,2H),6.95(d,1H),7.08(d,1H),7.36(d,2H),
7.41(d,2H),7.75(d,1H),8.16(d,1H).
16-22 (yellow solid, 123.8 DEG C)：δ4.63(d,2H),8.18(d,1H),7.00(d,1H),7.26(d,3H),
7.66(d,2H), 7.79(dd,1H).
16-82 (white solid, 116.4 DEG C)：δ4.63(d,2H),7.03(d,1H),7.15(d,2H),7.30(q,1H),
7.48(d,1H),7.78(dd,1H),8.10(d,1H).
16-121 (yellow oily liquid)：δ4.62(d,2H),8.15(d,1H),7.01(d,1H),7.25(d,3H),
7.67(d,2H),7.81(dd,1H).
28-4 (yellow solid, 108.4 DEG C)：δ1.65(d,3H),5.29(q,1H),6.93(d,1H),7.03(d,1H),
7.15(t,4H),7.71(dd,1H),8.20(s,1H).
46-2 (yellow oily liquid)：δ3.10(t,2H),3.85(q,2H),6.91(bs,1H),6.99(t,1H),7.05
(dd,2H),7.33(d,2H),7.57(d,1H),8.08(d,1H).
46-8 (white solid, 146.8 DEG C)：δ3.08(t,2H),3.82(q,2H),6.92(bs,1H),6.95(t,1H),
7.06(d,2H),7.36(d,2H),7.63(dd,1H),8.06(d,1H).
46-14 (yellow oily liquid)：δ3.08(t,2H),3.87(q,2H),5.33(bs,1H),6.95(d,1H),
7.08(t,1H),7.10(d,1H),7.41(m,2H),7.60(d,1H),8.09(t,1H).
76-13 (yellow solid, 122.6 DEG C)：δ7.01(t,1H),7.11(d,2H),7.41(d,2H),7.69(d,2H),
8.55(bs,1H).
95-12 (white solid, 98.6 DEG C)：δ1.60(s,3H),5.29(q,1H),6.93(d,1H),7.03(d,2H),
7.09(d,3H),7.72(d,1H),8.21(bs,1H).
103-2：δ3.07(t,2H),3.85(q,2H),6.90(bs,1H),6.96(t,1H),7.04(d,2H),7.34
(d,2H),7.61(d,1H),8.07(d,1H).
113-8 (white solid, 105.7 DEG C)：δ4.60(d,2H),8.17(d,1H),7.02(d,1H),7.27(d,3H),
7.68(d,2H),7.80(dd,1H).
113-15 (white solid, 129.1 DEG C)：δ4.65(d,2H),7.01(d,1H),7.25(d,3H),7.64(d,
2H),7.77(dd,1H),8.17(d,1H).
113-16 (yellow solid, 119.7 DEG C)：δ4.81(d,2H),7.06(d,1H),7.25(d,2H),7.64(s,
1H),7.80(d,1H),8.08(d,1H).
123-1 (yellow oily liquid)：δ3.10(t,2H),3.87(q,2H),5.30(bs,1H),6.97(d,1H),
7.09(q,2H),7.12(d,1H),7.42(m,2H),7.60(dd,1H),8.08(t,1H).
123-2 (white solid, 113.6 DEG C)：δ3.08(t,2H),3.86(q,2H),6.91(bs,1H),6.99(t,
1H),7.04(d,2H),7.35(d,2H),7.59(d,1H),8.06(d,1H).
Biological activity determination embodiment
The compounds of this invention to agriculture field in various pathogenic bacterias all show good activity, also show
Worm acaricidal activity.
Embodiment 16：Bactericidal activity is determined
With the compounds of this invention sample various 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, will test compound sample with the solvent being adapted to (solvent
Species such as acetone, methanol, DMF etc., and select according to its solvability to sample) dissolving, it is configured to desired concn and treats
Survey liquid.Under ultra-clean working environment, prepare liquid is added in the micropore of 96 well culture plates, then pathogen is bred into liquid suspension
It is added thereto, the culture plate after process is cultivated in being placed on constant incubator.Investigated after 24 hours, during investigation, estimated cause of disease
Bacterium brood body sprouts or growing state, and the sprouting according to control treatment or growing state, evaluates compound bacteriostatic activity.
Antifungal Activity in Vitro (being represented with the suppression ratio) test result of part of compounds is as follows：
Suppression ratio to rice blast fungus：
When liquor strength is 25mg/L, the suppression ratio of compound 4-7,16-1,16-22,28-4,46-2,103-2 etc. is
100%；When liquor strength is 8.3mg/L, the suppression ratio of compound 4-7 etc. is 100%；When liquor strength is 2.8mg/L, chemical combination
The suppression ratio of thing 4-7 etc. is 100%.
(2) live body protection activity is determined
Assay method is as follows：Using the potted plant assay method of live body, will test compound sample with a small amount of solvent (solvent
Species such as acetone, methanol, DMF etc., and select according to its solvability to sample, the volume ratio of quantity of solvent and spouting liquid
Equal to or less than 0.05) dissolving, diluted with the water containing 0.1% Tween 80, be configured to desired concn prepare liquid.Spray in crop
On machine, prepare liquid is sprayed on disease host plant (host plant is the standard Potted orchard in warm indoor cultivation), 24 hours
After carry out disease inoculation.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, and the disease plant for not needing moisturizing culture is directly connect in greenhouse
Plant and cultivate.After fully morbidity is compareed, (usually week age) carries out compound protection effect assessment.
The live body protection activity test result of part of compounds is as follows：
Live body preventive effect to cucumber downy mildew：
When liquor strength is 400mg/L, the preventive effect of compound 4-7,16-7,16-22,16-121,46-14,123-2 etc. is equal
For 100%, the preventive effect of compound 113-16 etc. is 98%；
When liquor strength is 100mg/L, the preventive effect of compound 4-7 etc. reaches 100%.
Live body preventive effect to corn rust：
When liquor strength is 400mg/L, the preventive effect of compound 4-7 etc. is 100%, and the preventive effect of compound 16-1 etc. is
More than 80%.
Live body preventive effect to cucumber anthracnose：
When liquor strength is 400mg/L, compound 16-1,16-7,16-22,16-82,16-121,46-2,46-8,46-
14th, the preventive effect of 103-2,113-8,113-15,123-1 etc. is 100%, and the preventive effect of compound 16-6,28-4,95-12 etc. is
98%；
When liquor strength is 100mg/L, the preventive effect of compound 16-1,16-7,16-22,103-2 etc. is 100%, compound
The preventive effect of 46-2 etc. is 95%, and the preventive effect of compound 16-6 etc. is 85%；
When liquor strength is 25mg/L, the preventive effect of compound 16-7 etc. is 98%, and the preventive effect of compound 16-22 etc. is
The preventive effect of 95%, compound 16-1 etc. is 90%；
When liquor strength is 6.25mg/L, the preventive effect of compound 16-7 etc. is 90%, and the preventive effect of compound 16-1 etc. is
The preventive effect of 85%, compound 16-22 etc. is 80%；
When liquor strength is 3.13mg/L, the preventive effect of compound 16-7 etc. is 90%.
Antifungal Activity in Vitro of the table 147 to rice blast
Live body protection activity of the table 148 to cucumber downy mildew
Live body protection activity of the table 149 to corn rust
Live body protection activity of the table 150 to cucumber anthracnose
Embodiment 17：Acaricidal activity is determined
Testing compound acetone/methanol (1：1) after mixed solvent dissolving, with the water containing 0.1% (wt) Tween 80
Concentration needed for being diluted to.With Tetranychus cinnabarinus as target, insecticidal activity assay is carried out using airbrush nebulizations.It is concrete to determine
Method：Take two panels true leaf Kidney bean Seedling, after connecting Tetranychus cinnabarinus into demodicid mite and investigating radix, carry out whole strain with airbrush aerosol apparatus at
Reason, pressure (are roughly equal to 0.7kg/cm for 10psi2), spouting liquid is 5ml.3 repetitions are often processed, standard sight room after process, is placed in,
After 72 hours, investigation survival demodicid mite number, calculates mortality rate.
It is as follows to the partial test result of Tetranychus cinnabarinus：
When liquor strength is 600mg/L, compound 16-22,28-4 etc. are 100% to Tetranychus cinnabarinus fatality rate.
Claims (10)
1. a kind of different thiazoles compound, it is characterised in that：Shown in compound structure below formula D：
In general formula D when B is connected to 5 of hexa-atomic aromatic rings, compound is as shown in formula I；When B is connected to hexa-atomic aromatic rings
When 4, as shown in formula II, when B is connected to 3 of hexa-atomic aromatic rings, compound is as shown in general formula III for compound：
In formula：
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C1-C12Alkane
Base, halo C1-C12Alkyl, C1-C12Alkoxyl, halo C1-C12Alkoxyl, C3-C12Cycloalkyl, C2-C12Thiazolinyl, C2-C12Alkynyl,
C2-C12Alkenyloxy group, halo C2-C12Alkenyloxy group, C2-C12Alkynyloxy group, halo C2-C12Alkynyloxy group, C1-C12Alkylthio group, halo C1-C12
Alkylthio group, C1-C12Alkoxy C1-C12Alkyl, halo C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12Alkyl, halogen
For C1-C12Alkylthio group C1-C12Alkyl, C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl sulfonyl
Base, halo C1-C12Alkyl sulphonyl, C1-C12Alkyl amino sulfonyl, C1-C12Alkyl amino, halo C1-C12Alkyl amino, two
(C1-C12Alkyl) amino, C1-C12Alkoxy carbonyl, CONH2、C1-C12Alkyl amino-carbonyl, two (C1-C12Alkyl) amino carbonyl
Base, cyano group C1-C12Alkoxyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkyl amino-carbonyl C1-C12Alkyl or two
(C1-C12Alkyl) amino carbonyl C1-C12Alkyl；
X is selected from O or S；
R6、R6′、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C12Alkyl, halo C1-C12Alkyl, C3-
C12Cycloalkyl, C1-C12Alkoxyl, halo C1-C12Alkoxyl, C1-C12Alkylthio group, halo C1-C12Alkylthio group, C2-C12Thiazolinyl,
Halo C2-C12Thiazolinyl, C2-C12Alkynyl, halo C2-C12Alkynyl, C3-C12Alkenyloxy group, halo C3-C12Alkenyloxy group, C3-C12Alkynes oxygen
Base, halo C3-C12Alkynyloxy group, C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphonyl, halogen
For C1-C12Alkyl sulphonyl, C1-C12Alkyl-carbonyl, halo C1-C12Alkyl-carbonyl, C1-C12Alkyl carbonyl epoxide, C1-C12Alkyl
Carbonylamino, C1-C12Alkyl sulphonyl epoxide, C1-C12Alkoxy carbonyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkane
Epoxide carbonyl amino, C1-C12Alkoxy C1-C12Alkoxyl or C1-C12Alkoxy carbonyl C1-C12Alkoxyl；
R8Selected from hydrogen, halogen, cyano group, C1-C8Alkyl, halo C1-C8It is alkyl, unsubstituted or further by the following group of 1-5
Substituted phenyl：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxyl or
Halo C1-C8Alkoxyl；
R9Selected from hydrogen, halogen, cyano group, C1-C8Alkyl, phenyl that is unsubstituted or being further substituted with by 1-5 following group：Halogen
Element, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxyl or halo C1-C8Alcoxyl
Base；
A is selected from hydrogen, hydroxyl, formoxyl, C1-C12Alkyl, halo C1-C12Alkyl, C1-C12Alkoxyl, halo C1-C12Alkoxyl,
C3-C12Cycloalkyl, C2-C12Thiazolinyl, C2-C12Alkynyl, halo C2-C12Thiazolinyl, halo C2-C12Alkynyl, C1-C12Alkoxy C1-C12
Alkyl, halo C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl,
C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphonyl, halo C1-C12Alkyl sulphonyl,
C1-C12Alkyl amino sulfonyl, two (C1-C12Alkyl) amino-sulfonyl, C1-C12Alkylsulfonyl aminocarbonyl, C1-C12Alkyl
Carbonylamino sulfonyl, C3-C12Cycloalkyloxycarbonyl, C1-C12Alkyl-carbonyl, halo C1-C12Alkyl-carbonyl, C1-C12Alcoxyl
Base 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-C12Allyloxycarbonyl, C2-C12Alkynyloxycar bonyl, C1-C12
Alkoxy C1-C12Alkoxy carbonyl, (miscellaneous) aryl carbonyl C that is unsubstituted or being further substituted with by 1-5 following group1-C6Alkane
Base, (miscellaneous) aryl carbonyl, (miscellaneous) aryloxycarbonyl, (miscellaneous) aryl C1-C6Alkyloxycarbonyl or (miscellaneous) aryl C1-C6Alkyl：Halogen
Element, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl or halo C1-C6Alkoxyl；
B is the substituent group being joined directly together by 3,4 or 5 carbon atoms of amide nitrogen atom and hexa-atomic aromatic rings ,-CRaRb、-
CH2CRaRb- or-CH2CRaRbCRaRb-；
Ra、RbMay be the same or different, be respectively selected from hydrogen, C1-C12Alkyl, C3-C12Cycloalkyl, C2-C12Thiazolinyl, C2-C12Alkynyl, halogen
For C2-C12Thiazolinyl, halo C2-C12Alkynyl, C1-C12Alkoxy C1-C12It is alkyl, unsubstituted or entered one by the following group of 1-5
The aryl C that step replaces1-C6Alkyl or heteroaryl C1-C6Alkyl：Halogen, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl
Or halo C1-C6Alkoxyl；Or Ra, RbWith the carbon composition C being connected3-C8Ring；
W is selected from CH or N.
2. compound according to claim 1, it is characterised in that：In formula I, II or III
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C1-C8Alkane
Base, halo C1-C8Alkyl, C1-C8Alkoxyl, halo C1-C8Alkoxyl, C3-C8Cycloalkyl, C2-C8Thiazolinyl, C2-C8Alkynyl, C2-C8
Alkenyloxy group, halo C2-C8Alkenyloxy group, C2-C8Alkynyloxy group, halo C2-C8Alkynyloxy group, C1-C8Alkylthio group, halo C1-C8Alkylthio group,
C1-C8Alkoxy C1-C8Alkyl, halo C1-C8Alkoxy C1-C8Alkyl, C1-C8Alkylthio group C1-C8Alkyl, halo C1-C8Alkylthio group
C1-C8Alkyl, C1-C8Alkyl sulphinyl, halo C1-C8Alkyl sulphinyl, C1-C8Alkyl sulphonyl, halo C1-C8Alkyl
Sulfonyl, C1-C8Alkyl amino sulfonyl, C1-C8Alkyl amino, halo C1-C8Alkyl amino, two (C1-C8Alkyl) amino, C1-
C8Alkoxy carbonyl, CONH2、C1-C8Alkyl amino-carbonyl, two (C1-C8Alkyl) amino carbonyl, cyano group C1-C8Alkoxyl, C1-C8
Alkoxy carbonyl C1-C8Alkyl, C1-C8Alkyl amino-carbonyl C1-C8Alkyl or two (C1-C8Alkyl) amino carbonyl C1-C8Alkyl；
X is selected from O or S；
R6、R6′、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C8Alkyl, halo C1-C8Alkyl, C3-
C6Cycloalkyl, C1-C8Alkoxyl, halo C1-C8Alkoxyl, C1-C8Alkylthio group, halo C1-C8Alkylthio group, C2-C8Thiazolinyl, halo
C2-C8Thiazolinyl, C2-C8Alkynyl, halo C2-C8Alkynyl, C3-C8Alkenyloxy group, halo C3-C8Alkenyloxy group, C3-C8Alkynyloxy group, halo C3-
C8Alkynyloxy group, C1-C8Alkyl sulphinyl, halo C1-C8Alkyl sulphinyl, C1-C8Alkyl sulphonyl, halo C1-C8Alkyl sulphur
Acyl group, C1-C8Alkyl-carbonyl, halo C1-C8Alkyl-carbonyl, C1-C8Alkyl carbonyl epoxide, C1-C8Alkyl-carbonyl-amino, C1-C8Alkane
Base sulfonyl epoxide, C1-C8Alkoxy carbonyl, C1-C8Alkoxy carbonyl C1-C8Alkyl, C1-C8Alkoxycarbonyl amino, C1-C8
Alkoxy C1-C8Alkoxyl or C1-C8Alkoxy carbonyl C1-C8Alkoxyl；
R8Selected from hydrogen, halogen, cyano group, C1-C6Alkyl, halo C1-C6It is alkyl, unsubstituted or further by the following group of 1-5
Substituted phenyl：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl or
Halo C1-C6Alkoxyl；
R9Selected from hydrogen, halogen, cyano group, C1-C6Alkyl, phenyl that is unsubstituted or being further substituted with by 1-5 following group：Halogen
Element, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl or halo C1-C6Alcoxyl
Base；
A is selected from hydrogen, hydroxyl, formoxyl, C1-C8Alkyl, halo C1-C8Alkyl, C1-C8Alkoxyl, halo C1-C8Alkoxyl, C3-C8
Cycloalkyl, C2-C8Thiazolinyl, C2-C8Alkynyl, halo C2-C8Thiazolinyl, halo C2-C8Alkynyl, C1-C8Alkoxy C1-C8Alkyl, halo
C1-C8Alkoxy C1-C8Alkyl, C1-C8Alkylthio group C1-C8Alkyl, halo C1-C8Alkylthio group C1-C8Alkyl, C1-C8Alkyl sulfenyl
Base, halo C1-C8Alkyl sulphinyl, C1-C8Alkyl sulphonyl, halo C1-C8Alkyl sulphonyl, C1-C8Alkyl sulfonyl amino
Base, two (C1-C8Alkyl) amino-sulfonyl, C1-C8Alkylsulfonyl aminocarbonyl, C1-C8Alkyl-carbonyl-amino sulfonyl, C3-C8
Cycloalkyloxycarbonyl, C1-C8Alkyl-carbonyl, halo C1-C8Alkyl-carbonyl, C1-C8Alkoxy carbonyl, halo C1-C8Alkoxyl carbonyl
Base, C1-C8Alkyl-carbonyl C1-C8Alkyl, C1-C8Alkoxy carbonyl C1-C8Alkyl, C1-C8Alkyl amino-carbonyl, two (C1-C8Alkane
Base) amino carbonyl, C2-C8Allyloxycarbonyl, C2-C8Alkynyloxycar bonyl, C1-C8Alkoxy C1-C8It is alkoxy carbonyl, unsubstituted
Or (miscellaneous) the aryl carbonyl C being further substituted with by 1-3 following group1-C6Alkyl, (miscellaneous) aryl carbonyl, (miscellaneous) aryloxy group carbonyl
Base, (miscellaneous) aryl C1-C6Alkyloxycarbonyl or (miscellaneous) aryl C1-C6Alkyl：Halogen, nitro, cyano group, C1-C4Alkyl, halo
C1-C4Alkyl, C1-C4Alkoxyl or halo C1-C4Alkoxyl；
B is the substituent group ,-CR being joined directly together by 3,4 or 5 carbon atoms of amide nitrogen atom and hexa-atomic aromatic ringsaRb、-
CH2CRaRb- or-CH2CRaRbCRaRb-；
Ra、RbMay be the same or different, be respectively selected from hydrogen, C1-C8Alkyl, C3-C8Cycloalkyl, C2-C8Thiazolinyl, C2-C8Alkynyl, halo
C2-C8Thiazolinyl, halo C2-C8Alkynyl, C1-C8Alkoxy C1-C8It is alkyl, unsubstituted or be further substituted with by the following group of 1-3
Aryl C1-C4Alkyl or heteroaryl C1-C4Alkyl：Halogen, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxyl or halo
C1-C4Alkoxyl；Or Ra、RbWith the carbon composition C being connected3-C8Ring；
W is selected from CH or N.
3. compound according to claim 2, it is characterised in that：In formula I, II or III
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C1-C4Alkane
Base, halo C1-C4Alkyl, C1-C4Alkoxyl, halo C1-C4Alkoxyl, C3-C4Cycloalkyl, C2-C4Thiazolinyl, C2-C4Alkynyl, C2-C4
Alkenyloxy group, halo C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, halo C2-C4Alkynyloxy group, C1-C4Alkylthio group, halo C1-C4Alkylthio group,
C1-C4Alkoxy C1-C4Alkyl, halo C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group
C1-C4Alkyl, C1-C4Alkyl sulphinyl, halo C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, halo C1-C4Alkyl
Sulfonyl, C1-C4Alkyl amino sulfonyl, C1-C4Alkyl amino, halo C1-C4Alkyl amino, two (C1-C4Alkyl) amino, C1-
C4Alkoxy carbonyl, CONH2、C1-C4Alkyl amino-carbonyl, two (C1-C4Alkyl) amino carbonyl, cyano group C1-C12Alkoxyl, C1-C4
Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkyl amino-carbonyl C1-C4Alkyl or two (C1-C4Alkyl) amino carbonyl C1-C4Alkyl；
X is selected from O or S；
R6、R6′、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkyl, C3-
C6Cycloalkyl, C1-C4Alkoxyl, halo C1-C4Alkoxyl, C1-C4Alkylthio group, halo C1-C4Alkylthio group, C2-C4Thiazolinyl, C2-
C4Alkynyl, C1-C4Alkyl sulphinyl, C1-C4Alkyl sulphonyl, C1-C4Alkyl-carbonyl or C1-C4Alkoxy C1-C4Alkoxyl；
R8Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4It is alkyl, unsubstituted or further by the following group of 1-5
Substituted phenyl：Halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxyl or
Halo C1-C6Alkoxyl；
R9Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, phenyl that is unsubstituted or being further substituted with by 1-5 following group：Halogen
Element, cyano group, nitro, hydroxyl, amino, sulfydryl, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxyl or halo C1-C4Alcoxyl
Base；
A is selected from hydrogen, C1-C4Alkyl, C1-C4Alkoxy carbonyl, C1-C4Alkoxy carbonyl C1-C4Alkyl, C1-C4Alkoxy carbonyl,
C1-C4Alkyl-carbonyl C1-C4Alkyl；
B is the substituent group ,-CR being joined directly together by 3,4 or 5 carbon atoms of amide nitrogen atom and hexa-atomic aromatic ringsaRb、-
CH2CRaRb- or-CH2CRaRbCRaRb-；
Ra、RbMay be the same or different, be respectively selected from hydrogen, methyl or ethyl；
W is selected from CH or N.
4. compound according to claim 3, it is characterised in that：In formula I, II or III
Compound of the structure as shown in I-A, I-B, I-C, I-D, I-E, II-A, III-A and III-B：
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C4Alkane
Base, C1-C4Alkoxyl or halo C1-C4Alkoxyl；
R6、R6′、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkyl, C1-
C4Alkoxyl, halo C1-C4Alkoxyl, C1-C4Alkyl-carbonyl；
R8Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4Alkyl；
R9Selected from hydrogen, halogen, cyano group, C1-C4Alkyl；
A is selected from hydrogen；
Ra、RbMay be the same or different, be respectively selected from hydrogen, methyl or ethyl.
5. compound according to claim 4, it is characterised in that：
In formula I-A, I-B, I-C, I-D, I-E, II-A, III-A or III-B
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C4Alkane
Base, C1-C4Alkoxyl or halo C1-C4Alkoxyl；
R6、R6′、R7May be the same or different, be respectively selected from hydrogen, halogen, nitro, cyano group or C1-C4Alkyl；
R8Selected from hydrogen, halogen, cyano group, C1-C4Alkyl, halo C1-C4Alkyl；
R9Selected from hydrogen, halogen, cyano group, C1-C4Alkyl；
A is selected from hydrogen；
Ra、RbSelected from hydrogen.
6. compound according to claim 5, it is characterised in that：
In formula I-A, I-B, I-C, I-D, I-E, II-A, III-A or III-B
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C2Alkane
Base, C1-C4Alkoxyl or halo C1-C2Alkoxyl；
R6、R6′、R7May be the same or different, be respectively selected from hydrogen, halogen or C1-C4Alkyl；
R8Selected from hydrogen, halogen, cyano group, C1-C2Alkyl or halo C1-C2Alkyl；
R9Selected from hydrogen, halogen, cyano group or C1-C2Alkyl；
A is selected from hydrogen；
Ra、RbSelected from hydrogen.
7. compound according to claim 6, it is characterised in that：
In formula I-A, I-B, I-C, I-D, I-E, II-A, III-A or III-B
R1、R2、R3、R4、R5May be the same or different, be respectively selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C2Alkane
Base, C1-C4Alkoxyl；
R6、R6′、R7Selected from hydrogen；
R8Selected from halogen；
R9Selected from halogen；
A is selected from hydrogen；
Ra、RbSelected from hydrogen.
8. a kind of formula I, II or Ш compound according to claim 1 is used as system in agricultural, forestry or health field
Standby antibacterial, the purposes of insecticidal/acaricidal agent medicine.
9. a kind of sterilization and disinsection miticide composition, it is characterised in that：Containing formula I, II or Ш chemical combination as claimed in claim 1
Used as active component, in compositionss, the weight percentage of active component is 0.5-99% to thing.
10. a kind of anti-pathogen, the method for insect evil mite, it is characterised in that：By the compositionss described in the claim 9 of effective dose
Impose on described pathogenic bacteria, insect evil mite or its somatomedin.
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| CN1278803A (en) * | 1997-11-12 | 2001-01-03 | 拜尔公司 | Isothiazole carboxylic acid amides and the application thereof in order to proteot plants |
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