CN104974136A - Pyrazole amide type compound and application thereof - Google Patents
Pyrazole amide type compound and application thereof Download PDFInfo
- Publication number
- CN104974136A CN104974136A CN201410131285.2A CN201410131285A CN104974136A CN 104974136 A CN104974136 A CN 104974136A CN 201410131285 A CN201410131285 A CN 201410131285A CN 104974136 A CN104974136 A CN 104974136A
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- China
- Prior art keywords
- alkyl
- halo
- hydrogen
- carbonyl
- alkoxyl group
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- 0 *c(cc1)ccc1Cl Chemical compound *c(cc1)ccc1Cl 0.000 description 2
- BYFMLTGRQULLHE-UHFFFAOYSA-N CCc1n[n](C)c(C(C2(C)C(Cc(cn3)ccc3Oc3ccc(C(F)(F)F)cc3)CC2)=O)c1Cl Chemical compound CCc1n[n](C)c(C(C2(C)C(Cc(cn3)ccc3Oc3ccc(C(F)(F)F)cc3)CC2)=O)c1Cl BYFMLTGRQULLHE-UHFFFAOYSA-N 0.000 description 1
- MYGAJZBZLONIBZ-UHFFFAOYSA-N COC(c1cccnc1Cl)=O Chemical compound COC(c1cccnc1Cl)=O MYGAJZBZLONIBZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a pyrazole amide type compound. The structure of the compound is shown by the following general formula shown in the specification, and the definition of each substituent group in the formula is described in the specification. The compound with the general formula has broad-spectrum bactericidal and insecticidal activity in the agricultural field, and has a very good prevention effect on various germs including cucumber mildew, wheat powdery mildew, corn rust, rice blast, cucumber gray mold and the like. Particularly, the compound still has a very good control effect on the corn rust at a relatively low dosage. Meanwhile, part of the compound disclosed by the invention also has relatively good insecticidal activity, and can be used for controlling armyworms, plutella xylostella, peach aphids and tetranychus cinnabarinus.
Description
Technical field
The invention belongs to agricultural bactericidal, field of pesticides.Relate to a kind of pyrazol acid amide compounds and uses thereof particularly.
Background technology
Patent US4950668A discloses the N-benzyl pyrazole acidamide derivatives such as tebufenpyrad (tebufenpyrad) and has pesticide and miticide actility.The N-benzyl pyrazole acidamide derivative that patent US5039693A discloses the phenoxy group replacements such as Tolfenpyrad (tolfenpyrad) has pesticide and miticide actility.The pyrazole amide analog derivative that patent CN1927860A discloses benzene dibenzyl has pesticide and miticide actility.All report without fungicidal activity.The pyrazole amide analog derivative that patent WO02083647A1 discloses containing xenyl has sterilization, desinsection and acaricidal activity.
Patent US5039693 discloses the compound of following general formula, has pesticide and miticide actility, but this patent does not disclose it has fungicidal activity.
Patent EP0394043A1, US5264448A disclose the compound of following general formula, have pesticide and miticide actility; The compound that JP2001064176 also discloses following general formula only uses as slimming agents.Wherein: A=pyrazole ring, B is pyridine ring, identical with this general formula (I) compound portion, however, and the not any fungicidal activity report of these three patents.
Patent EP0365925A1 discloses the compound of following general formula, has pesticide and miticide actility, although compound is identical with this general formula (I) compound portion in patent, this patent is also reported without any fungicidal activity.
Patent WO2009024342A2 discloses in the compound of following general formula and particular compound CK1(patent and is numbered 1.581), part of compounds under 0.02% active constituent content to wheat powdery mildew, net blotch of barley, brown rust of wheat, wheat balck shank preventive effect is minimum is 50%.
Patent WO02089583A1 discloses compound and the particular compound Tolfenpyrad (being numbered No.4 in patent) of following general formula, No.5 is numbered) in CK2(patent, No.2 is numbered in CK3(patent), be numbered No.1 in CK4(patent), there is fungicidal activity.
Patent WO02083647A1 discloses in the compound of following general formula and particular compound CK5(patent and is numbered No.18), there is sterilization, pesticide and miticide actility.
Also disclose following compound in patent WO2013064079, there is fungicidal activity.
Patent US4968805(EP329020) report following Compound C K10 and there is good desinsection under 500ppm, kill mite and fungicidal activity.Part of compounds also has good desinsection, kills mite and fungicidal activity under 50ppm.
The compound of above patent report all belongs to Pyrazole Acyl benzylamine compound.
Numbering 169 (CK11), 519 (CK12) in the patent CN103081916(patent of the present inventor's application) and CN103087041 (compound 98 in patent, CK13) disclose following compound, there is good fungicidal activity.
In prior art, the compound of structure as shown in general formula of the present invention has no report.
Summary of the invention
Modern agricultural production needs the novel pesticide continually developing out novel structure, excellent performance.The object of the present invention is to provide a kind of pyrazol acid amide compounds that just can control multiple germ, insect under very little dosage, it can be used for the medicine of preparation control germ and insect evil mite in agricultural or other field.
Technical scheme of the present invention is as follows:
The invention provides a kind of pyrazol acid amide compounds, compound structure is as shown in general formula:
Wherein: Q is selected from
or
When Q (C=O) NAB-is connected to 5 of pyridine ring, compound is as shown in general formula I; When Q (C=O) NAB-is connected to 4 of pyridine ring, compound is as shown in general formula I I; When Q (C=O) NAB-is connected to 3 of pyridine ring, compound is as shown in general formula Ш:
In formula:
A is selected from hydrogen, hydroxyl, formyl radical, C
1-C
12alkyl, halo C
1-C
12alkyl, C
1-C
12alkoxyl group, halo C
1-C
12alkoxyl group, C
3-C
12cycloalkyl, C
1-C
12alkylthio, C
2-C
12enylsulfanyl, C
2-C
12thiazolinyl, C
2-C
12alkynyl, halo C
2-C
12thiazolinyl, halo C
2-C
12alkynyl, C
1-C
12alkoxy C
1-C
12alkyl, halo C
1-C
12alkoxy C
1-C
12alkyl, C
1-C
12alkylthio C
1-C
12alkyl, halo C
1-C
12alkylthio C
1-C
12alkyl, C
1-C
12alkyl sulphinyl, halo C
1-C
12alkyl sulphinyl, C
1-C
12alkyl sulphonyl, halo C
1-C
12alkyl sulphonyl, C
1-C
12alkyl amino sulfonyl, two (C
1-C
12alkyl) amino-sulfonyl, C
1-C
12alkylsulfonyl aminocarbonyl, C
1-C
12alkyl-carbonyl-amino alkylsulfonyl, C
3-C
12cycloalkyloxycarbonyl, C
1-C
12alkyl-carbonyl, halo C
1-C
12alkyl-carbonyl, C
1-C
12alkoxy carbonyl, halo C
1-C
12alkoxy carbonyl, C
1-C
12alkyl-carbonyl C
1-C
12alkyl, C
1-C
12alkoxy carbonyl C
1-C
12alkyl, C
1-C
12alkyl amino-carbonyl, two (C
1-C
12alkyl) aminocarboxyl, C
2-C
12allyloxycarbonyl, C
2-C
12alkynyloxycar bonyl, C
1-C
12alkoxy C
1-C
12alkoxy carbonyl, C
1-C
12alkylamino sulfenyl, two (C
1-C
12alkyl) amino sulfenyl, (mixing) aryl carbonyl C that is unsubstituted or that replaced further by the following group of 1-5
1-C
6alkyl, (mixing) aryl carbonyl, (mixing) aryloxycarbonyl, (mixing) aryl C
1-C
6alkyloxycarbonyl or (mixing) aryl C
1-C
6alkyl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen and pyridine ring 3,4 or 5 carbon are directly connected
2cR
ar
b-or-CH
2cR
ar
bcR
ar
b-;
R
a, R
bmay be the same or different, be selected from hydrogen, C respectively
1-C
12alkyl, C
3-C
12cycloalkyl, C
2-C
12thiazolinyl, C
2-C
12alkynyl, halo C
2-C
12thiazolinyl, halo C
2-C
12alkynyl, C
1-C
12alkoxy C
1-C
12alkyl, aryl C that is unsubstituted or that replaced further by 1-5 following group
1-C
6alkyl or heteroaryl C
1-C
6alkyl: halogen, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group, or Ra, R
bc is formed with the carbon be connected
3-C
8ring;
X is selected from O or S;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C respectively
1-C
12alkyl, halo C
1-C
12alkyl, C
1-C
12alkoxyl group, halo C
1-C
12alkoxyl group, C
3-C
12cycloalkyl, C
2-C
12thiazolinyl, C
2-C
12alkynyl, C
2-C
12alkene oxygen base, halo C
2-C
12alkene oxygen base, C
2-C
12alkynyloxy group, halo C
2-C
12alkynyloxy group, C
1-C
12alkylthio, halo C
1-C
12alkylthio, C
1-C
12alkoxy C
1-C
12alkyl, halo C
1-C
12alkoxy C
1-C
12alkyl, C
1-C
12alkylthio C
1-C
12alkyl, halo C
1-C
12alkylthio C
1-C
12alkyl, C
1-C
12alkyl sulphinyl, halo C
1-C
12alkyl sulphinyl, C
1-C
12alkyl sulphonyl, halo C
1-C
12alkyl sulphonyl, C
1-C
12alkyl amino sulfonyl, C
1-C
12alkylamino, halo C
1-C
12alkylamino, two (C
1-C
12alkyl) amino, C
1-C
12alkoxy carbonyl, CONH
2, C
1-C
12alkyl amino-carbonyl, two (C
1-C
12alkyl) aminocarboxyl, cyano group C
1-C
12alkoxyl group, C
1-C
12alkoxy carbonyl C
1-C
12alkyl, C
1-C
12alkyl amino-carbonyl C
1-C
12alkyl or two (C
1-C
12alkyl) aminocarboxyl C
1-C
12alkyl;
R
6, R
6', R
7may be the same or different, be selected from hydrogen, halogen, nitro, cyano group, C respectively
1-C
12alkyl, halo C
1-C
12alkyl, C
3-C
12cycloalkyl, C
1-C
12alkoxyl group, halo C
1-C
12alkoxyl group, C
1-C
12alkylthio, halo C
1-C
12alkylthio, C
2-C
12thiazolinyl, halo C
2-C
12thiazolinyl, C
2-C
12alkynyl, halo C
2-C
12alkynyl, C
3-C
12alkene oxygen base, halo C
3-C
12alkene oxygen base, C
3-C
12alkynyloxy group, halo C
3-C
12alkynyloxy group, C
1-C
12alkyl sulphinyl, halo C
1-C
12alkyl sulphinyl, C
1-C
12alkyl sulphonyl, halo C
1-C
12alkyl sulphonyl, C
1-C
12alkyl-carbonyl, halo C
1-C
12alkyl-carbonyl, C
1-C
12alkyl-carbonyl oxygen base, C
1-C
12alkyl-carbonyl-amino, C
1-C
12alkyl sulphonyl oxygen base, C
1-C
12alkoxy carbonyl, C
1-C
12alkoxy carbonyl C
1-C
12alkyl, C
1-C
12alkoxycarbonyl amino, C
1-C
12alkoxy C
1-C
12alkoxyl group or C
1-C
12alkoxy carbonyl C
1-C
12alkoxyl group;
R
8be selected from hydrogen, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxy C
1-C
8alkyl, cyano group C
1-C
8alkyl or C
3-C
6cycloalkyl, the unsubstituted or aryl that replaced further by the following group of 1-5 or heteroaryl: halogen, cyano group, nitro, C
1-C
6alkyl, C
1-C
6alkoxyl group, C
1-C
6alkylthio, C
3-C
6cycloalkyl, C
2-C
6thiazolinyl, C
2-C
6alkynyl, halo C
1-C
6alkyl, halo C
1-C
6alkoxyl group, halo C
1-C
6alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
6thiazolinyl, halo C
2-C
6alkynyl, C
1-C
6alkyl sulphinyl, C
1-C
6alkyl sulphonyl, C
1-C
6alkylamino, two (C
1-C
6alkyl) amino, C
1-C
6alkyl-carbonyl, C
1-C
6alkoxy carbonyl, C
1-C
6alkyl amino-carbonyl, unsubstituted or be independently selected from by 1-5 the aryl or heteroaryl that following group replaces further: hydrogen, halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
9be selected from hydrogen, halogen, cyano group, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, cyano group C
1-C
8alkyl, cyano group C
1-C
8alkoxyl group, C
3-C
8alkene oxygen base, halo C
3-C
8alkene oxygen base, C
3-C
8alkynyloxy group, halo C
3-C
8alkynyloxy group, C
1-C
8alkylthio, halo C
1-C
8alkylthio, C
1-C
8alkyl sulphinyl, halo C
1-C
12alkyl sulphinyl, C
1-C
8alkyl sulphonyl, halo C
1-C
8alkyl sulphonyl, phenyl that is unsubstituted or that be independently selected from following group replace further by 1-5: halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
1-C
8alkylthio, C
3-C
8cycloalkyl, C
2-C
8thiazolinyl, C
2-C
8alkynyl, halo C
1-C
8alkylthio, halo C
3-C
8cycloalkyl, halo C
2-C
8thiazolinyl, halo C
2-C
8alkynyl, C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl, C
1-C
8alkylamino, two (C
1-C
8alkyl) amino, C
1-C
8alkyl-carbonyl, C
1-C
8alkoxy carbonyl or C
1-C
8alkyl amino-carbonyl;
R
10be selected from hydrogen, halogen, cyano group, nitro, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
1-C
8alkylthio, halo C
1-C
8alkylthio, C
1-C
8alkyl sulphinyl, halo C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl or halo C
1-C
8alkyl sulphonyl;
R
10' be selected from hydrogen, halogen, cyano group, C
1-C
8alkyl, halo C
1-C
8alkyl, cyano group C
1-C
8alkyl or C
3-C
6cycloalkyl;
And the present invention does not comprise following 3 compounds (Chemistry & Biology.2010, compd A and B in the compound 2 in 17:686-694 and WO9924404):
The preferred compound of the present invention as shown in general formula I, II or III, wherein
A is selected from hydrogen, hydroxyl, formyl radical, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
3-C
8cycloalkyl, C
1-C
8alkylthio, C
2-C
8enylsulfanyl, C
2-C
8thiazolinyl, C
2-C
8alkynyl, halo C
2-C
8thiazolinyl, halo C
2-C
8alkynyl, C
1-C
8alkoxy C
1-C
8alkyl, halo C
1-C
8alkoxy C
1-C
8alkyl, C
1-C
8alkylthio C
1-C
8alkyl, halo C
1-C
8alkylthio C
1-C
8alkyl, C
1-C
8alkyl sulphinyl, halo C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl, halo C
1-C
8alkyl sulphonyl, C
1-C
8alkyl amino sulfonyl, two (C
1-C
8alkyl) amino-sulfonyl, C
1-C
8alkylsulfonyl aminocarbonyl, C
1-C
8alkyl-carbonyl-amino alkylsulfonyl, C
3-C
8cycloalkyloxycarbonyl, C
1-C
8alkyl-carbonyl, halo C
1-C
8alkyl-carbonyl, C
1-C
8alkoxy carbonyl, halo C
1-C
8alkoxy carbonyl, C
1-C
8alkyl-carbonyl C
1-C
8alkyl, C
1-C
8alkoxy carbonyl C
1-C
8alkyl, C
1-C
8alkyl amino-carbonyl, two (C
1-C
8alkyl) aminocarboxyl, C
2-C
8allyloxycarbonyl, C
2-C
8alkynyloxycar bonyl, C
1-C
8alkoxy C
1-C
8alkoxy carbonyl, C
1-C
8alkylamino sulfenyl, two (C
1-C
8alkyl) amino sulfenyl, (mixing) aryl carbonyl C that is unsubstituted or that replaced further by the following group of 1-3
1-C
6alkyl, (mixing) aryl carbonyl, (mixing) aryloxycarbonyl, (mixing) aryl C
1-C
6alkyloxycarbonyl or (mixing) aryl C
1-C
6alkyl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen and pyridine ring 3,4 or 5 carbon are directly connected
2cR
ar
b-or-CH
2cR
ar
bcR
ar
b-;
R
a, R
bmay be the same or different, be selected from hydrogen, C respectively
1-C
8alkyl, C
3-C
8cycloalkyl, C
2-C
8thiazolinyl, C
2-C
8alkynyl, halo C
2-C
8thiazolinyl, halo C
2-C
8alkynyl, C
1-C
8alkoxy C
1-C
8alkyl, aryl C that is unsubstituted or that replaced further by 1-3 following group
1-C
4alkyl or heteroaryl C
1-C
4alkyl: halogen, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group; Or R
a, R
bc is formed with the carbon be connected
3-C
8ring;
X is selected from O or S;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C respectively
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
3-C
8cycloalkyl, C
2-C
8thiazolinyl, C
2-C
8alkynyl, C
2-C
8alkene oxygen base, halo C
2-C
8alkene oxygen base, C
2-C
8alkynyloxy group, halo C
2-C
8alkynyloxy group, C
1-C
8alkylthio, halo C
1-C
8alkylthio, C
1-C
8alkoxy C
1-C
8alkyl, halo C
1-C
8alkoxy C
1-C
8alkyl, C
1-C
8alkylthio C
1-C
8alkyl, halo C
1-C
8alkylthio C
1-C
8alkyl, C
1-C
8alkyl sulphinyl, halo C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl, halo C
1-C
8alkyl sulphonyl, C
1-C
8alkyl amino sulfonyl, C
1-C
8alkylamino, halo C
1-C
8alkylamino, two (C
1-C
8alkyl) amino, C
1-C
8alkoxy carbonyl, CONH
2, C
1-C
8alkyl amino-carbonyl, two (C
1-C
8alkyl) aminocarboxyl, cyano group C
1-C
8alkoxyl group, C
1-C
8alkoxy carbonyl C
1-C
8alkyl, C
1-C
8alkyl amino-carbonyl C
1-C
8alkyl or two (C
1-C
8alkyl) aminocarboxyl C
1-C
8alkyl;
R
6, R
6', R
7may be the same or different, be selected from hydrogen, halogen, nitro, cyano group, C respectively
1-C
8alkyl, halo C
1-C
8alkyl, C
3-C
6cycloalkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
1-C
8alkylthio, halo C
1-C
8alkylthio, C
2-C
8thiazolinyl, halo C
2-C
8thiazolinyl, C
2-C
8alkynyl, halo C
2-C
8alkynyl, C
3-C
8alkene oxygen base, halo C
3-C
8alkene oxygen base, C
3-C
8alkynyloxy group, halo C
3-C
8alkynyloxy group, C
1-C
8alkyl sulphinyl, halo C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl, halo C
1-C
8alkyl sulphonyl, C
1-C
8alkyl-carbonyl, halo C
1-C
8alkyl-carbonyl, C
1-C
8alkyl-carbonyl oxygen base, C
1-C
8alkyl-carbonyl-amino, C
1-C
8alkyl sulphonyl oxygen base, C
1-C
8alkoxy carbonyl, C
1-C
8alkoxy carbonyl C
1-C
8alkyl, C
1-C
8alkoxycarbonyl amino, C
1-C
8alkoxy C
1-C
8alkoxyl group or C
1-C
8alkoxy carbonyl C
1-C
8alkoxyl group;
R
8be selected from hydrogen, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxy C
1-C
3alkyl, cyano group C
1-C
6alkyl or C
3-C
6cycloalkyl, the unsubstituted or aryl that replaced further by the following group of 1-5 or heteroaryl: halogen, cyano group, nitro, C
1-C
4alkyl, C
1-C
4alkoxyl group, C
1-C
4alkylthio, C
3-C
6cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, halo C
1-C
4alkyl, halo C
1-C
4alkoxyl group, halo C
1-C
4alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
4thiazolinyl, halo C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkyl-carbonyl, C
1-C
4alkoxy carbonyl, C
1-C
4alkyl amino-carbonyl, unsubstituted or be independently selected from by 1-5 the phenyl or pyridyl that following group replaces further: hydrogen, halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
9be selected from hydrogen, halogen, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group, halo C
1-C
6alkoxyl group, cyano group C
1-C
6alkyl, cyano group C
1-C
6alkoxyl group, halo C
1-C
6alkylthio, halo C
1-C
6alkyl sulphinyl, halo C
1-C
6alkyl sulphonyl, phenyl that is unsubstituted or that be independently selected from following group replace further by 1-5: halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group, halo C
1-C
6alkoxyl group, C
1-C
6alkylthio, C
3-C
6cycloalkyl, C
2-C
6thiazolinyl, C
2-C
6alkynyl, halo C
1-C
6alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
6thiazolinyl, halo C
2-C
6alkynyl, C
1-C
6alkyl sulphinyl, C
1-C
6alkyl sulphonyl, C
1-C
6alkylamino, two (C
1-C
6alkyl) amino, C
1-C
6alkyl-carbonyl, C
1-C
6alkoxy carbonyl or C
1-C
6alkyl amino-carbonyl;
R
10be selected from hydrogen, halogen, cyano group, nitro, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group, halo C
1-C
6alkoxyl group, C
1-C
6alkylthio, halo C
1-C
6alkylthio, C
1-C
6alkyl sulphinyl, halo C
1-C
6alkyl sulphinyl, C
1-C
6alkyl sulphonyl or halo C
1-C
6alkyl sulphonyl;
R
10' be selected from hydrogen, halogen, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, cyano group C
1-C
6alkyl or C
3-C
6cycloalkyl.
The present invention further preferred compound as shown in general formula I, II or III, wherein
A is selected from hydrogen, C
1-C
4alkyl, C
1-C
4alkoxy carbonyl, C
1-C
4alkoxy carbonyl C
1-C
4alkyl, C
1-C
4alkoxy carbonyl, C
1-C
4alkyl-carbonyl C
1-C
4alkyl;
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen and pyridine ring 3,4 or 5 carbon are directly connected
2cR
ar
b-or-CH
2cR
ar
bcR
ar
b-;
R
a, R
bmay be the same or different, be selected from hydrogen, methyl or ethyl respectively;
X is selected from O or S;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C respectively
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, C
3-C
4cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, C
2-C
4alkene oxygen base, halo C
2-C
4alkene oxygen base, C
2-C
4alkynyloxy group, halo C
2-C
4alkynyloxy group, C
1-C
4alkylthio, halo C
1-C
4alkylthio, C
1-C
4alkoxy C
1-C
4alkyl, halo C
1-C
4alkoxy C
1-C
4alkyl, C
1-C
4alkylthio C
1-C
4alkyl, halo C
1-C
4alkylthio C
1-C
4alkyl, C
1-C
4alkyl sulphinyl, halo C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, halo C
1-C
4alkyl sulphonyl, C
1-C
4alkyl amino sulfonyl, C
1-C
4alkylamino, halo C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkoxy carbonyl, CONH
2, C
1-C
4alkyl amino-carbonyl, two (C
1-C
4alkyl) aminocarboxyl, cyano group C
1-C
12alkoxyl group, C
1-C
4alkoxy carbonyl C
1-C
4alkyl, C
1-C
4alkyl amino-carbonyl C
1-C
4alkyl or two (C
1-C
4alkyl) aminocarboxyl C
1-C
4alkyl;
R
6, R
6', R
7may be the same or different, be selected from hydrogen, halogen, nitro, cyano group, C respectively
1-C
4alkyl, halo C
1-C
4alkyl, C
3-C
6cycloalkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, C
1-C
4alkylthio, halo C
1-C
4alkylthio, C
2-C
4thiazolinyl, C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkyl-carbonyl or C
1-C
4alkoxy C
1-C
4alkoxyl group;
R
8be selected from hydrogen, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxy C
1-C
3alkyl, cyano group C
1-C
4alkyl, C
3-C
6cycloalkyl, the unsubstituted or aryl that replaced further by the following group of 1-5 or heteroaryl: halogen, cyano group, nitro, C
1-C
4alkyl, C
1-C
4alkoxyl group, C
1-C
4alkylthio, C
3-C
6cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, halo C
1-C
4alkyl, halo C
1-C
4alkoxyl group, halo C
1-C
4alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
4thiazolinyl, halo C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkyl-carbonyl, C
1-C
4alkoxy carbonyl, C
1-C
4alkyl amino-carbonyl, unsubstituted or be independently selected from by 1-5 the phenyl or pyridyl that following group replaces further: hydrogen, halogen, cyano group, nitro, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
9be selected from hydrogen, halogen, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, cyano group C
1-C
4alkyl, cyano group C
1-C
4alkoxyl group, halo C
1-C
4alkylthio, halo C
1-C
4alkyl sulphinyl, halo C
1-C
4alkyl sulphonyl, phenyl that is unsubstituted or that be independently selected from following group replace further by 1-5: halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, C
1-C
4alkylthio, C
3-C
6cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, halo C
1-C
4alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
4thiazolinyl, halo C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkyl-carbonyl, C
1-C
4alkoxy carbonyl or C
1-C
4alkyl amino-carbonyl;
R
10be selected from hydrogen, halogen, cyano group, nitro, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, C
1-C
4alkylthio, halo C
1-C
4alkylthio, C
1-C
4alkyl sulphinyl, halo C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl or halo C
1-C
4alkyl sulphonyl;
R
10' be selected from hydrogen, halogen, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, cyano group C
1-C
4alkyl or C
3-C
6cycloalkyl.
The present invention more further preferred compound as shown in general formula I, II or III, wherein
Fixing amide nitrogen atom is through the link position of B and pyridine ring 3,4 or 5 carbon atoms; reduce the protection domain of R8 on Q substituting group further, (in general formula I-A, I-B, II-A, Ш-A, R8 is selected from hydrogen, C to obtain six kinds of formulas such as I-A, I-B, I-C, I-D, II-A or Ш-A respectively simultaneously
1-C
4alkyl or C
3-C
6cycloalkyl, i.e. R
8'; In general formula I-C, I-D, R8 is selected from phenyl that is unsubstituted or that independently replaced further by 1-5 substituting group or pyridyl):
Therefore, in the present invention, further preferred compound is: in general formula I-A, I-B, I-C, I-D, II-A or Ш-A
A is selected from hydrogen;
R
a, R
bmay be the same or different, be selected from hydrogen, methyl or ethyl respectively;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, C respectively
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
6, R
6', R
7may be the same or different, be selected from hydrogen, halogen, nitro, cyano group, C respectively
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group or C
1-C
4alkyl-carbonyl;
R
8' be selected from hydrogen, C
1-C
4alkyl or C
3-C
6cycloalkyl;
R
9be selected from hydrogen, halogen, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, cyano group C
1-C
3alkyl, cyano group C
1-C
3alkoxyl group, halo C
1-C
3alkylthio, halo C
1-C
3alkyl sulphinyl, halo C
1-C
3alkyl sulphonyl, phenyl that is unsubstituted or that be independently selected from following group replace further by 1-3: halogen, cyano group, nitro, C
1-C
4alkyl, C
1-C
4alkoxyl group, C
1-C
4alkylthio, C
3-C
6cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, halo C
1-C
4alkyl, halo C
1-C
4alkoxyl group, halo C
1-C
4alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
4thiazolinyl, halo C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkyl-carbonyl, C
1-C
4alkoxy carbonyl or C
1-C
4alkyl amino-carbonyl;
R
10be selected from hydrogen, halogen, cyano group, nitro, C
1-C
4alkyl, halo C
1-C
4alkyl, halo C
1-C
4alkylthio or halo C
1-C
4alkyl sulphinyl;
R
10' be selected from hydrogen, halogen, cyano group, C
1-C
4alkyl or halo C
1-C
4alkyl;
R
11, R
12, R
13, R
14may be the same or different, be selected from hydrogen, halogen, cyano group, C respectively
1-C
4alkyl, halo C
1-C
4alkyl or halo C
1-C
4alkoxyl group;
Y is selected from N or CR
15, wherein R
15be selected from hydrogen, halogen, C
1-C
4alkyl or halo C
1-C
4alkyl.
The present invention further in preferred compound the compound substituent shown in mutual-through type I-A, I-B, I-C, I-D, II-A or Ш-A be preferably:
A, R
a, R
b, R
6, R
6', R
7all be selected from hydrogen;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, C respectively
1-C
4alkyl, halo C
1-C
4alkyl or C
1-C
4alkoxyl group;
R
8' be selected from C
1-C
4alkyl;
R
9be selected from halogen, C
1-C
4alkyl or halo C
1-C
4alkyl;
R
10or R
10' be selected from hydrogen, halogen or C
1-C
4alkyl;
R
11, R
12, R
13, R
14may be the same or different, be selected from hydrogen or halogen respectively;
Y is selected from N.
Further the compound substituent shown in mutual-through type I-A, I-B, I-C, I-D, II-A or Ш-A is more preferably in preferred compound in the present invention:
A, R
a, R
b, R
6, R
6', R
7all be selected from hydrogen;
In general formula I-A, R
1, R
10be selected from hydrogen or halogen; R
2be selected from hydrogen, halogen or C
1-C
4alkyl; R
3be selected from hydrogen, halogen or halo C
1-C
4alkyl; R
4be selected from hydrogen, halogen, C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkyl; R
5be selected from hydrogen; R
8', R
9be selected from C
1-C
4alkyl;
In general formula I-B, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from halogen; R
8' be selected from C
1-C
4alkyl; R
9be selected from C
1-C
4alkyl or halo C
1-C
4alkyl; R
10' be selected from hydrogen or C
1-C
4alkyl;
In general formula I-C, Y=N; R
1be selected from hydrogen or halo C
1-C
4alkyl; R
2be selected from hydrogen or halogen; R
3, R
5, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen, halogen, C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkyl; R
9, R
11be selected from halogen;
In general formula I-D, Y=N; R
1, R
3, R
5be selected from hydrogen or halogen; R
2, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen or C
1-C
4alkyl; R
9, R
11be selected from halogen;
In general formula I I-A, R
1, R
2, R
3, R
5be selected from hydrogen; R
4, R
10be selected from halogen; R
8', R
9be selected from C
1-C
4alkyl;
In general formula III-A, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from hydrogen or halogen; R
8', R
9be selected from C
1-C
4alkyl; R
10be selected from halogen.
The present invention further in preferred compound the compound substituent shown in mutual-through type I-A, I-B, I-C, I-D, II-A or Ш-A more more preferably:
A, R
a, R
b, R
6, R
6', R
7all be selected from hydrogen;
In general formula I-A, R
1, R
10be selected from hydrogen or chlorine; R
2be selected from hydrogen, chlorine or methyl; R
3be selected from hydrogen, chlorine or trifluoromethyl; R
4be selected from hydrogen, chlorine, methyl, methoxyl group or trifluoromethyl; R
5be selected from hydrogen; R
8' be selected from methyl; R
9be selected from methyl or ethyl;
In general formula I-B, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from chlorine; R
8' be selected from methyl; R
9be selected from methyl or trifluoromethyl; R
10' be selected from hydrogen or methyl;
In general formula I-C, Y=N; R
1be selected from hydrogen or trifluoromethyl; R
2be selected from hydrogen or chlorine; R
3, R
5, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen, chlorine, methyl, methoxyl group or trifluoromethyl; R
9be selected from bromine; R
11be selected from chlorine;
In general formula I-D, Y=N; R
1, R
3, R
5be selected from hydrogen or chlorine; R
2, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen or methyl; R
9be selected from bromine; R
11be selected from chlorine;
In general formula I I-A, R
1, R
2, R
3, R
5be selected from hydrogen; R
4, R
10be selected from chlorine; R
8' be selected from methyl; R
9be selected from methyl or ethyl;
In general formula III-A, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from hydrogen or chlorine; R
8', R
9be selected from methyl; R
10be selected from chlorine.
The present invention is further being preferably of the compound substituent shown in mutual-through type I-A, I-B, I-C or I-D in preferred compound further:
A, R
a, R
b, R
6, R
6', R
7all be selected from hydrogen;
In general formula I-A, R
1, R
10be selected from hydrogen or chlorine; R
2be selected from hydrogen, chlorine or methyl; R
3be selected from hydrogen, chlorine or trifluoromethyl; R
4be selected from hydrogen, chlorine, methyl, methoxyl group or trifluoromethyl; R
5be selected from hydrogen; R
8' be selected from methyl; R
9be selected from methyl or ethyl;
In general formula I-B, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from chlorine; R
8', R
9, R
10' be selected from methyl;
In general formula I-C, Y=N; R
1be selected from hydrogen or trifluoromethyl; R
2be selected from hydrogen or chlorine; R
3, R
5, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen, chlorine or methyl; R
9be selected from bromine; R
11be selected from chlorine;
In general formula I-D, Y=N; R
1, R
3, R
5be selected from hydrogen or chlorine; R
2, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen or methyl; R
9be selected from bromine; R
11be selected from chlorine;
In general formula III-A, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from hydrogen or chlorine; R
8', R
9be selected from methyl; R
10be selected from chlorine.
In the definition of the general formula I provided, II or Ш compound, collect the following substituting group of term general proxy used above:
Halogen: refer to fluorine, chlorine, bromine or iodine.Alkyl: straight or branched alkyl, such as methyl, ethyl, propyl group, sec.-propyl or the tertiary butyl.Cycloalkyl: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl.Substituting group is as methyl, halogen etc.Haloalkyl: straight or branched alkyl, the hydrogen atom on these alkyl can partly or entirely replace by halogen atom, such as, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl etc.Alkoxyl group: straight or branched alkyl, is connected in structure through Sauerstoffatom key.Halogenated alkoxy: straight or branched alkoxyl group, the hydrogen atom on these alkoxyl groups can partly or entirely replace by halogen atom.Such as, chlorine methoxyl group, dichloro methoxyl group, trichloromethoxy, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group, trifluoro ethoxy etc.Alkylthio: straight or branched alkyl, is connected in structure through sulphur atom key.Halogenated alkylthio: straight or branched alkylthio, hydrogen atom on these alkyl can partly or entirely replace by halogen atom, such as chloromethane sulfenyl, dichloromethane sulfenyl, trichloro-methylthio, fluorine methylthio group, difluoro methylthio group, trifluoromethylthio, chlorine fluorine methylthio group etc.Cyanoalkyl: CN-alkyl, such as CNCH
3, CNC
2h
5.Cyano alkoxy: CN-alkoxyl group, such as CNCH
3o, CNC
2h
5o.Thiazolinyl: straight or branched alkene class, such as vinyl, 1-propenyl, 2-propenyl and different butenyls, pentenyl and hexenyl isomers.Thiazolinyl also comprises polyenoid class, as 1,2-propadiene base and 2,4-hexadienyl.Haloalkenyl group: straight or branched alkene class, the hydrogen atom on these thiazolinyls can partly or entirely replace by halogen atom.Alkynyl: straight or branched alkynes class, such as ethynyl, 1-proyl, 2-propynyl and different butynyl, pentynyl and hexynyl isomers.Alkynyl also comprises the group be made up of multiple triple bond, as 2,5-hexadiyne base.Halo alkynyl: straight or branched alkynes class, the hydrogen atom on these alkynyls can partly or entirely replace by halogen atom.Alkene oxygen base: straight or branched alkene class, is connected in structure through Sauerstoffatom key.Enylsulfanyl: straight or branched alkene class, is connected in structure through sulphur atom key.As CH
2=CHCH
2s-.Haloalkene oxygen base: straight or branched alkene oxygen base, the hydrogen atom on these alkene oxygen bases can partly or entirely replace by halogen atom.Alkynyloxy group: straight or branched alkynes class, is connected in structure through Sauerstoffatom key.Halo alkynyloxy group: straight or branched alkynyloxy group, the hydrogen atom on these alkynyloxy groups can partly or entirely replace by halogen atom.Allyloxycarbonyl: as CH
2=CHCH
2oCO-etc.Alkynyloxycar bonyl: as CH ≡ CCH
2oCO-etc.Alkylamino: straight or branched alkyl, is connected in structure through nitrogen-atoms key.Haloalkylamino: straight or branched alkylamino, the hydrogen atom on these alkyl can partly or entirely be replaced by halogen atom lock.Alkyl sulphinyl: straight or branched alkyl is connected in structure, as methylsulfinyl through sulfinyl (-SO-).Alkylsulfinyl: straight or branched alkyl sulphinyl, the hydrogen atom on its alkyl can partly or entirely replace by halogen atom.Alkyl sulphonyl: straight or branched alkyl is through alkylsulfonyl (-SO
2-) be connected in structure, as methyl sulphonyl.Halogenated alkyl sulfonyl: straight or branched alkyl sulphonyl, the hydrogen atom on its alkyl can partly or entirely replace by halogen atom.Alkyl-carbonyl: alkyl is connected in structure, as CH through carbonyl
3cO-, CH
3cH
2cO-.Halogenated alkyl carbonyl: the hydrogen atom on the alkyl of alkyl-carbonyl can partly or entirely replace by halogen atom, as CF
3cO-.Alkyl-carbonyl-amino: as CH
3cONH-, CH
3cH
2nHCONH-.Alkyl sulphonyl oxygen base: alkyl-S (O)
2-O-.Alkoxy carbonyl: alkyl-O-CO-, as CH
3oCO-, C
2h
5oCO-.Alkyl-carbonyl oxygen base: such as CH
3cOO-, CH
3cH
2nHCOO-.Halo alkoxy carbonyl: the hydrogen atom on the alkyl of alkoxy carbonyl can partly or entirely replace by halogen atom, as ClCH
2cH
2oCO-, CF
3cH
2oCO-etc.Alkoxy carbonyl alkyl: alkoxy carbonyl-alkyl-, such as CH
3oCOCH
2-.Alkoxycarbonyl amino: alkyl-O-CO-NH-.Alkoxyalkyl: alkyl-O-alkyl-, such as CH
3oCH
2-.Alkyloxy-alkoxy: alkyl-O-alkyl-O-, such as CH
3oCH
2o-.Dialkyl amido: such as (CH
3)
2nH-, (C
2h
5)
2nH-.Halogenated alkoxy alkyl: the hydrogen atom on the alkyl of alkoxyalkyl can partly or entirely replace by halogen atom.As ClCH
2cH
2oCH
2-.Alkylthio alkyl: alkyl-S-alkyl-, such as CH
3sCH
2-.Haloalkylthioalkyl: the hydrogen atom on the alkyl of alkylthio alkyl can partly or entirely replace by halogen atom, as ClCH
2cH
2sCH
2-, CF
3cH
2sCH
2-etc.Alkyl amino sulfonyl: alkyl-NH-SO
2-.Dialkyl amino sulfonyl: (alkyl)
2-N-SO
2-.Alkylsulfonyl aminocarbonyl: alkyl-SO
2-NH-CO-.Alkyl amino alkyl carbonyl: such as CH
3nH
2cOCH
2-.Alkoxycarbonylalkoxy: alkyl-O-CO-alkyl-O-.Alkyl-carbonyl-amino alkylsulfonyl: alkyl-CO-NH-SO
2-.Cycloalkyloxycarbonyl: as ring propoxycarbonyl, cyclohexyloxy carbonyl etc.Alkylcarbonylalkyl: alkyl-CO-alkyl-.Alkyl amino-carbonyl: alkyl-NH-CO-, such as CH
3nHCO-, (CH
3)
2nCO-.Dialkyl amino carbonyl: (alkyl)
2-NH-CO-, such as (CH
3)
2-N-CO-, (C
2h
5)
2-N-CO-.Alkoxyalkoxycarbonyl: as CH
3o CH
2cH
2oCO-etc.Alkylamino sulfenyl: as CH
3nHS-, C
2h
5nHS-.Dialkyl amido sulfenyl: as (CH
3)
2nS-, (C
2h
5)
2nS-.Aryl moiety in (mixing) aryl alkyl carbonyl, (mixing) aryl carbonyl, (mixing) aryloxycarbonyl, (mixing) arylalkyl oxygen base carbonyl, (mixing) arylalkyl comprises phenyl or naphthyl etc.Heteroaryl is containing the heteroatomic five-ring of one or more N, O, S or six-ring.Such as furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl etc.(mixing) aryl alkyl carbonyl: as PhCOCH
2-.(mixing) aryl carbonyl: as benzoyl, 4-chlorobenzene formacyl, picolinoyl, pyrimidine formyl radical, pyrazoyl etc.(mixing) aryloxycarbonyl: as phenyloxycarbonyl, 4-cHorophenoxycarbonyl, 4-nitrophenoxy carbonyl, naphthoxycarbonyl, pyridyloxy carbonyl, 2-pyrimidinyl oxy carbonyl etc.(mixing) arylalkyl oxygen base carbonyl: as benzyloxycarbonyl, 4-chlorobenzyl oxygen base carbonyl, 4-trifluoromethyl benzyl oxygen base carbonyl, picolyl oxygen base carbonyl etc.(mixing) arylalkyl: as phenmethyl, styroyl, to chlorophenylmethyl,
deng.
Table 1 lists R in general formula I, II or Ш respectively to table 4
8, R
9, R
10, R
a, R
bthe concrete substituting group of part, but they are not limited only to these substituting groups, and in general formula I, II or Ш, other substituting groups are as previously mentioned.
Table 1R
8substituting group
Table 2R
9substituting group
Table 3R
10(R
10') substituting group
| R 10 | R 10 |
| H | CF 3 |
| Cl | OCF 3 |
| Br | NO 2 |
| CH 3 | CH 2Cl |
| OCH 3 | CN |
| SCH 3 | SO 2CH 3 |
| SCF 3 | SOCF 3 |
Table 4R
a(R
b) substituting group
Part of compounds of the present invention can illustrate by the particular compound listed in table 5-table 116, but does not limit the present invention.In general formula compound I-A, I-B, I-C, I-D, II-A or Ш-A related to, R
6=R
6'=H.
General formula I-A chemical formula is as follows, and substituting group involved in general formula is see table 5-19, and concrete representation compound refers to each table,
Table 5: work as A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=R
7during=H, R
1, R
2, R
3, R
4, R
5substituting group is in table 5, and be corresponding in turn to the 1-180 of table 5, representation compound is numbered 5-1-5-180.
Table 5
| Numbering | R 1 | R 2 | R 3 | R 4 | R 5 |
| 1 | H | H | H | H | H |
| 2 | H | F | H | H | H |
| 3 | H | H | F | H | H |
| 4 | H | H | H | F | H |
| 5 | H | Cl | H | H | H |
| 6 | H | H | Cl | H | H |
| 7 | H | H | H | Cl | H |
| 8 | H | Br | H | H | H |
| 9 | H | H | Br | H | H |
| 10 | H | H | H | Br | H |
| 11 | H | I | H | H | H |
| 12 | H | H | I | H | H |
| 13 | H | H | H | I | H |
| 14 | H | CH 3 | H | H | H |
| 15 | H | H | CH 3 | H | H |
| 16 | H | H | H | CH 3 | H |
| 17 | H | OCH 3 | H | H | H |
| 18 | H | H | OCH 3 | H | H |
| 19 | H | H | H | OCH 3 | H |
| 20 | H | CF 3 | H | H | H |
| 21 | H | H | CF 3 | H | H |
| 22 | H | H | H | CF 3 | H |
| 23 | H | OCF 3 | H | H | H |
| 24 | H | H | OCF 3 | H | H |
| 25 | H | H | H | OCF 3 | H |
| 26 | H | NO 2 | H | H | H |
| 27 | H | H | NO 2 | H | H |
| 28 | H | H | H | NO 2 | H |
| 29 | H | CN | H | H | H |
| 30 | H | H | CN | H | H |
| 31 | H | H | H | CN | H |
| 32 | H | CH(CH 3) 2 | H | H | H |
| 33 | H | H | CH(CH 3) 2 | H | H |
| 34 | H | H | H | CH(CH 3) 2 | H |
| 35 | H | H | H | t-Bu | H |
| 36 | H | SCH 3 | H | H | H |
| 37 | H | H | SCH 3 | H | H |
| 38 | H | H | H | SCH 3 | H |
| 39 | H | SCF 3 | H | H | H |
| 40 | H | H | SCF 3 | H | H |
| 41 | H | H | H | SCF 3 | H |
| 42 | H | COCH 3 | H | H | H |
| 43 | H | H | COCH 3 | H | H |
| 44 | H | H | H | COCH 3 | H |
| 45 | H | SOCH 3 | H | H | H |
| 46 | H | H | SOCH 3 | H | H |
| 47 | H | H | H | SOCH 3 | H |
| 48 | H | SO 2CH 3 | H | H | H |
| 49 | H | H | SO 2CH 3 | H | H |
| 50 | H | H | H | SO 2CH 3 | H |
| 51 | H | OCHF 2 | H | H | H |
| 52 | H | H | OCHF 2 | H | H |
| 53 | H | H | H | OCHF 2 | H |
| 54 | H | CO 2CH 3 | H | H | H |
| 55 | H | H | CO 2CH 3 | H | H |
| 56 | H | H | H | CO 2CH 3 | H |
| 57 | H | N(CH 3) 2 | H | H | H |
| 58 | H | H | N(CH 3) 2 | H | H |
| 59 | H | H | H | N(CH 3) 2 | H |
| 60 | H | N(C 2H 5) 2 | H | H | H |
| 61 | H | H | N(C 2H 5) 2 | H | H |
| 62 | H | H | H | N(C 2H 5) 2 | H |
| 63 | H | NHCOCH 3 | H | H | H |
| 64 | H | H | NHCOCH 3 | H | H |
| 65 | H | H | H | NHCOCH 3 | H |
| 66 | H | NHSO 2CH 3 | H | H | H |
| 67 | H | H | NHSO 2CH 3 | H | H |
| 68 | H | H | H | NHSO 2CH 3 | H |
| 69 | H | OCH 2CH=CH 2 | H | H | H |
| 70 | H | H | OCH 2CH=CH 2 | H | H |
| 71 | H | H | H | OCH 2CH=CH 2 | H |
| 72 | H | OCH 2C≡CH | H | H | H |
| 73 | H | H | OCH 2C≡CH | H | H |
| 74 | H | H | H | OCH 2C≡CH | H |
| 75 | H | F | F | H | H |
| 76 | H | F | H | F | H |
| 77 | F | F | H | H | H |
| 78 | H | F | H | H | F |
| 79 | H | H | F | F | H |
| 80 | F | H | F | H | H |
| 81 | H | Cl | Cl | H | H |
| 82 | H | Cl | H | Cl | H |
| 83 | Cl | Cl | H | H | H |
| 84 | H | Cl | H | H | Cl |
| 85 | H | H | Cl | Cl | H |
| 86 | Cl | H | Cl | H | H |
| 87 | H | NO 2 | H | NO 2 | H |
| 88 | NO 2 | NO 2 | H | H | H |
| 89 | H | NO 2 | H | H | NO 2 |
| 90 | NO 2 | H | NO 2 | H | H |
| 91 | H | CN | H | CN | H |
| 92 | CN | CN | H | H | H |
| 93 | H | CN | H | H | CN |
| 94 | CN | H | CN | H | H |
| 95 | H | CH 3 | CH 3 | H | H |
| 96 | H | CH 3 | H | CH 3 | H |
| 97 | CH 3 | CH 3 | H | H | H |
| 98 | H | CH 3 | H | H | CH 3 |
| 99 | H | H | CH 3 | CH 3 | H |
| 100 | CH 3 | H | CH 3 | H | H |
| 101 | H | CF 3 | H | CF 3 | H |
| 102 | CF 3 | CF 3 | H | H | H |
| 103 | H | CF 3 | H | H | CF 3 |
| 104 | CF 3 | H | CF 3 | H | H |
| 105 | H | OCF 3 | H | OCF 3 | H |
| 106 | OCF 3 | OCF 3 | H | H | H |
| 107 | H | OCF 3 | H | H | OCF 3 |
| 108 | OCF 3 | H | OCF 3 | H | H |
| 109 | H | CH 3 | Cl | H | H |
| 110 | H | CH 3 | H | Cl | H |
| 111 | H | H | Cl | CH 3 | H |
| 112 | H | Cl | H | CH 3 | H |
| 113 | Cl | CH 3 | H | H | H |
| 114 | H | CH 3 | H | H | Cl |
| 115 | H | Br | CH 3 | H | H |
| 116 | H | H | CH 3 | Cl | H |
| 117 | H | CH 3 | NO 2 | H | H |
| 118 | H | CH 3 | H | NO 2 | H |
| 119 | H | CH 3 | H | OCH 3 | H |
| 120 | NO 2 | CH 3 | H | H | H |
| 121 | H | Cl | H | CF 3 | H |
| 122 | CF 3 | Cl | H | H | H |
| 123 | H | Cl | H | NO 2 | H |
| 124 | NO 2 | Cl | H | H | H |
| 125 | H | CF 3 | H | Br | H |
| 126 | H | CF 3 | H | NO 2 | H |
| 127 | H | H | CF 3 | NO 2 | H |
| 128 | H | H | CF 3 | Cl | H |
| 129 | H | CF 3 | H | CN | H |
| 130 | H | Cl | H | CN | H |
| 131 | H | NO 2 | H | CN | H |
| 132 | H | NO 2 | H | CH 3 | H |
| 133 | H | NO 2 | H | CF 3 | H |
| 134 | H | NO 2 | H | Cl | H |
| 135 | Cl | NO 2 | H | H | H |
| 136 | H | H | NO 2 | CH 3 | H |
| 137 | H | H | NO 2 | Cl | H |
| 138 | H | CN | F | H | H |
| 139 | H | CN | H | NO 2 | H |
| 140 | H | CN | H | Cl | H |
| 141 | CH 3 | CN | H | H | H |
| 142 | H | Cl | Cl | Cl | H |
| 143 | Cl | Cl | Cl | H | H |
| 144 | Cl | Cl | H | Cl | H |
| 145 | H | Cl | H | Cl | Cl |
| 146 | Cl | H | Cl | Cl | H |
| 147 | H | CH 3 | H | CH 3 | CH 3 |
| 148 | H | OCH 3 | H | OCH 3 | OCH 3 |
| 149 | H | Cl | Cl | B r | H |
| 150 | H | F | H | F | Cl |
| 151 | H | CH 3 | H | Br | Br |
| 152 | H | CF 3 | H | Cl | Cl |
| 153 | H | CF 3 | H | Br | Br |
| 154 | H | F | H | Cl | Br |
| 155 | H | Cl | H | NO 2 | Cl |
| 156 | H | Br | H | NO 2 | Br |
| 157 | H | Cl | H | CN | Cl |
| 158 | H | Cl | H | CF 3 | Cl |
| 159 | H | Br | H | CF 3 | Br |
| 160 | H | Cl | CH 3 | H | Cl |
| 161 | H | Cl | H | CONH 2 | Cl |
| 162 | H | Cl | H | CO 2CH 3 | Cl |
| 163 | H | Cl | H | NHCOCH 3 | Cl |
| 164 | H | Cl | H | OCF 3 | Cl |
| 165 | H | Br | H | F | Br |
| 166 | H | Br | H | CH 3 | Br |
| 167 | H | Cl | H | COCH 3 | Cl |
| 168 | Cl | Cl | H | NO 2 | H |
| 169 | H | F | H | F | Cl |
| 170 | H | Cl | H | CF 3 | Br |
| 171 | H | CH 3 | H | NO 2 | Cl |
| 172 | H | CH 3 | H | NO 2 | Br |
| 173 | H | CH 3 | H | Cl | NO 2 |
| 174 | H | CH 3 | H | Br | NO 2 |
| 175 | H | NO 2 | H | CF 3 | Cl |
| 176 | H | NO 2 | H | CF 3 | Br |
| 177 | H | F | H | Br | Br |
| 178 | H | CN | H | Cl | Cl |
| 179 | H | CN | H | Br | Br |
| 180 | F | F | F | H | F |
Table 6: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
a=R
b=R
7during=H, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 6-1-6-180.
Table 7: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=H, R
a=R
b=R
7during=H, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 7-1-7-180.
Table 8:A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 8-1-8-180.
Table 9: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 9-1-9-180.
Table 10: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=H, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 10-1-10-180.
Table 11:A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 11-1-11-180.
Table 12: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 12-1-12-180.
Table 13: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=H, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 13-1-13-180.
Table 14: work as A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 14-1-14-180.
Table 15: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 15-1-15-180.
Table 16: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=H, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 16-1-16-180.
Table 17: work as A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
7=H, R
a=R
b=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 17-1-17-180.
Table 18: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
7=H, R
a=R
b=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 18-1-18-180.
Table 19: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=H, R
7=H, R
a=R
b=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 19-1-19-180.
General formula I-B chemical formula is as follows, and substituting group involved in general formula is see table 20-34, and concrete representation compound refers to each table,
Table 20: work as A=H, R
8'=CH
3, R
9=CF
3, R
10'=H, R
a=R
b=R
7during=H, R
1, R
2, R
3, R
4, R
5substituting group, in table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 20-1-20-180.
Table 21: work as A=H, R
8'=CH
3, R
9=CHF
2, R
10'=H, R
a=R
b=R
7during=H, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 21-1-21-180.
Table 22: work as A=H, R
8'=CH
3, R
9=CH
3, R
10'=CH
3, R
a=R
b=R
7during=H, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 22-1-22-180.
Table 23: work as A=H, R
8'=CH
3, R
9=CF
3, R
10'=H, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 23-1-23-180.
Table 24: work as A=H, R
8'=CH
3, R
9=CHF
2, R
10'=H, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 24-1-24-180.
Table 25: work as A=H, R
8'=CH
3, R
9=CH
3, R
10'=CH
3, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 25-1-25-180.
Table 26: work as A=H, R
8'=CH
3, R
9=CF
3, R
10'=H, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 26-1-26-180.
Table 27: work as A=H, R
8'=CH
3, R
9=CHF
2, R
10'=H, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 27-1-27-180.
Table 28: work as A=H, R
8'=CH
3, R
9=CH
3, R
10'=CH
3, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 28-1-28-180.
Table 29: work as A=H, R
8'=CH
3, R
9=CF
3, R
10'=H, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 29-1-29-180.
Table 30: work as A=H, R
8'=CH
3, R
9=CHF
2, R
10'=H, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 30-1-30-180.
Table 31: work as A=H, R
8'=CH
3, R
9=CH
3, R
10'=CH
3, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 31-1-31-180.
Table 32: work as A=H, R
8'=CH
3, R
9=CF
3, R
10'=H, R
7=H, R
a=R
b=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 32-1-32-180.
Table 33: work as A=H, R
8'=CH
3, R
9=CHF
2, R
10'=H, R
7=H, R
a=R
b=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 33-1-33-180.
Table 34: work as A=H, R
8'=CH
3, R
9=CH
3, R
10'=CH
3, R
7=H, R
a=R
b=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 34-1-34-180.
General formula I-C chemical formula is as follows, and substituting group involved in general formula is see table 35-59, and concrete representation compound refers to each table,
Table 35: work as A=H, R
7=H, R
1=R
2=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14in table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 35-1-35-32.
Table 35
| Numbering | Y | R 9 | R 10 | R 11 | R 12 | R 13 | R 14 |
| 1 | N | OCH 2CF 3 | H | Cl | H | H | H |
| 2 | N | OCH 2CF 3 | H | Br | H | H | H |
| 3 | N | OCHF 2 | H | Cl | H | H | H |
| 4 | N | OCHF 2 | H | Br | H | H | H |
| 5 | N | CF 3 | H | Cl | H | H | H |
| 6 | N | CF 3 | H | Br | H | H | H |
| 7 | N | Cl | H | Cl | H | H | H |
| 8 | N | Cl | H | Br | H | H | H |
| 9 | N | Cl | H | Cl | H | CF 3 | H |
| 10 | N | Cl | H | Cl | H | CN | H |
| 11 | N | Cl | H | Cl | H | Cl | H |
| 12 | N | Cl | H | Cl | H | Cl | Cl |
| 13 | N | Br | H | Cl | H | H | H |
| 14 | N | Br | H | Br | H | H | H |
| 15 | N | Br | H | Cl | H | CF 3 | H |
| 16 | N | Br | H | Cl | H | CN | H |
| 17 | N | Br | H | Cl | H | Cl | H |
| 18 | N | Br | H | Cl | H | Cl | Cl |
| 19 | N | CN | H | Cl | H | H | H |
| 20 | N | CN | H | Br | H | H | H |
| 21 | N | OCH 3 | H | Cl | H | H | H |
| 22 | N | OCH 3 | H | Br | H | H | H |
| 23 | N | CH 3 | H | Cl | H | H | H |
| 24 | N | CH 3 | H | Br | H | H | H |
| 25 | N | C 2H 5 | H | Cl | H | H | H |
| 26 | N | C 2H 5 | H | Br | H | H | H |
| 27 | N | OCH 2CH=CH 2 | H | Cl | H | H | H |
| 28 | N | Propynyloxy base | H | Cl | H | H | H |
| 29 | N | OCH 2CN | H | Cl | H | H | H |
| 30 | C-Cl | CN | CF 3 | Cl | H | CF 3 | H |
| 31 | C-Cl | CN | SCF 3 | Cl | H | CF 3 | H |
| 32 | CH | CH 3 | H | Cl | H | H | H |
Table 36: work as A=H, R
7=H, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 36-1-36-32.
Table 37: work as A=H, R
7=H, R
4=CH
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 37-1-37-32.
Table 38: work as A=H, R
7=H, R
4=NO
2, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 38-1-38-32.
Table 39: work as A=H, R
7=H, R
4=F, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 39-1-39-32.
Table 40: work as A=H, R
7=H, R
4=CF
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 40-1-40-32.
Table 41: work as A=H, R
7=H, R
4=OCH
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 41-1-41-32.
Table 42: work as A=H, R
7=H, R
4=t-Bu, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 42-1-42-32.
Table 43: work as A=H, R
7=H, R
4=CN, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 43-1-43-32.
Table 44: work as A=H, R
7=H, R
2=Cl, R
1=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 44-1-44-32.
Table 45: work as A=H, R
7=H, R
1=Cl, R
2=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 45-1-45-32.
Table 46: work as A=H, R
7=H, R
1=CF
3, R
2=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 46-1-46-32.
Table 47: work as A=H, R
7=H, R
2=CH
3, R
4=Cl, R
1=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 47-1-47-32.
Table 48: work as A=H, R
7=H, R
2=R
4=Cl, R
1=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 48-1-48-32.
Table 49: work as A=H, R
7=H, R
3=R
5=Cl, R
1=R
2=R
4during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 49-1-49-32.
Table 50: work as A=H, R
7=H, R
1=R
4=Cl, R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 50-1-50-32.
Table 51: work as A=H, R
7=H, R
1=R
3=Cl, R
2=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 51-1-51-32.
Table 52: work as A=H, R
7=H, R
2=R
5=Cl, R
1=R
3=R
4during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 52-1-52-32.
Table 53: work as A=H, R
7=H, R
2=Cl, R
4=CF
3, R
1=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 53-1-53-32.
Table 54: work as A=H, R
7=H, R
2=Cl, R
4=NO
2, R
1=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 54-1-54-32.
Table 55: work as A=H, R
7=H, R
1=CF
3, R
2=Cl, R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 55-1-55-32.
Table 56: work as A=H, R
7=H, R
2=R
5=Cl, R
4=CF
3, R
1=R
3during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 56-1-56-32.
Table 57: work as A=H, R
7=Cl, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 57-1-57-32.
Table 58: work as A=CH
3, R
7=Cl, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 58-1-58-32.
Table 59: work as A=CH
2ph, R
7=Cl, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 59-1-59-32.
General formula I-D chemical formula is as follows, and substituting group involved in general formula is see table 60-94, and concrete representation compound refers to each table,
Table 60: work as A=H, Ra=R
b=R
7=H, R
1=R
2=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 60-1-60-32.
Table 61: work as A=H, Ra=R
b=R
7=H, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 61-1-61-32.
Table 62: work as A=H, Ra=R
b=R
7=H, R
4=CH
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 62-1-62-32.
Table 63: work as A=H, Ra=R
b=R
7=H, R
4=NO
2, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 63-1-63-32.
Table 64: work as A=H, Ra=R
b=R
7=H, R
4=F, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 64-1-64-32.
Table 65: work as A=H, Ra=R
b=R
7=H, R
4=CF
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 65-1-65-32.
Table 66: work as A=H, Ra=R
b=R
7=H, R
4=OCH
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 66-1-66-32.
Table 67: work as A=H, Ra=R
b=R
7=H, R
4=t-Bu, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 67-1-67-32.
Table 68: work as A=H, Ra=R
b=R
7=H, R
4=CN, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 68-1-68-32.
Table 69: work as A=H, Ra=R
b=R
7=H, R
2=Cl, R
1=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 69-1-69-32.
Table 70: work as A=H, Ra=R
b=R
7=H, R
1=Cl, R
2=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 70-1-70-32.
Table 71: work as A=H, Ra=R
b=R
7=H, R
1=CF
3, R
2=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 71-1-71-32.
Table 72: work as A=H, Ra=R
b=R
7=H, R
2=R
4=Cl, R
1=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, the 1-32 representation compound being corresponding in turn to table 35 is numbered 72-1-72-32.
Table 73: work as A=H, R
7=H, R
3=R
5=Cl, R
1=R
2=R
4during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 73-1-73-32.
Table 74: work as A=H, Ra=R
b=R
7=H, R
1=R
4=Cl, R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 74-1-74-32.
Table 75: work as A=H, Ra=R
b=R
7=H, R
1=R
3=Cl, R
2=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 75-1-75-32.
Table 76: work as A=H, Ra=R
b=R
7=H, R
2=R
5=Cl, R
1=R
3=R
4during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 76-1-76-32.
Table 77: work as A=H, Ra=R
b=R
7=H, R
2=Cl, R
4=CF
3, R
1=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 77-1-77-32.
Table 78: work as A=H, Ra=R
b=R
7=H, R
2=Cl, R
4=NO
2, R
1=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 78-1-78-32.
Table 79: work as A=H, Ra=R
b=R
7=H, R
2=CH
3, R
4=Cl, R
1=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 79-1-79-32.
Table 80: work as A=H, Ra=R
b=R
7=H, R
1=CF
3, R
2=Cl, R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 80-1-80-32.
Table 81: work as A=H, Ra=R
b=R
7=H, R
2=R
5=Cl, R
4=CF
3, R
1=R
3during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 81-1-81-32.
Table 82: work as A=H, Ra=R
b=H, R
7=Cl, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 82-1-82-32.
Table 83: work as A=CH
3, Ra=R
b=H, R
7=Cl, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 83-1-83-32.
Table 84: work as A=CH
2ph, Ra=R
b=H, R
7=Cl, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 84-1-84-32.
Table 85: work as A=H, Ra=CH
3, R
b=R
7=H, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 85-1-85-32.
Table 86: work as A=H, Ra=CH
3, R
b=R
7=H, R
1=R
2=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 86-1-86-32.
Table 87: work as A=H, Ra=CH
3, R
b=R
7=H, R
4=CF
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 87-1-87-32.
Table 88: work as A=H, Ra=CH
3, R
b=R
7=H, R
4=CH
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 88-1-88-32.
Table 89: work as A=H, Ra=R
b=CH
3, R
7=H, R
4=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 89-1-89-32.
Table 90: work as A=H, Ra=R
b=CH
3, R
7=H, R
1=R
2=R
3=R
4=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 90-1-90-32.
Table 91: work as A=H, Ra=R
b=CH
3, R
7=H, R
4=CF
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 91-1-91-32.
Table 92: work as A=H, Ra=R
b=CH
3, R
7=H, R
4=CH
3, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 92-1-92-32.
Table 93: work as A=H, Ra=CH
3, R
b=H, R
4=R
7=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 93-1-93-32.
Table 94: work as A=H, Ra=R
b=CH
3, R
4=R
7=Cl, R
1=R
2=R
3=R
5during=H, substituting group Y, R
9, R
10, R
11, R
12, R
13, R
14consistent with table 35, be corresponding in turn to the 1-32 of table 35, representation compound is numbered 94-1-94-32.
General formula I I-A chemical formula is as follows, and substituting group involved in general formula is see table 95-102, and concrete representation compound refers to each table,
Table 95: work as A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=R
7during=H, R
1, R
2, R
3, R
4, R
5substituting group, in table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 95-1-95-180.
Table 96: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
a=R
b=R
7during=H, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 96-1-96-180.
Table 97:A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 97-1-97-180.
Table 98: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 98-1-98-180.
Table 99:A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 99-1-99-180.
Table 100: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 100-1-100-180.
Table 101: work as A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 101-1-101-180.
Table 102: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 102-1-102-180.
General formula Ш-A chemical formula is as follows, and substituting group involved in general formula is see table 103-116, and concrete representation compound refers to each table,
Table 103: work as A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=R
7during=H, R
1, R
2, R
3, R
4, R
5substituting group, in table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 103-1-103-180.
Table 104: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
a=R
b=R
7during=H, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 104-1-104-180.
Table 105:A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 105-1-105-180.
Table 106: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
a=R
b=H, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 106-1-106-180.
Table 107:A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 107-1-107-180.
Table 108: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
b=R
7=H, R
a=CH
3time, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 108-1-108-180.
Table 109: work as A=H, R
8'=CH
3, R
9=CH
3, R
10=Cl, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 109-1-109-180.
Table 110: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 5, be corresponding in turn to the 1-180 of table 5, representation compound is numbered 110-1-110-180.
Table 111: work as A=H, R
8'=CH
3, R
9=C
2h
5, R
10=Cl, R
b=H, R
a=CH
3, R
7during=Cl, substituent R
1, R
2, R
3, R
4, R
5consistent with table 111, be corresponding in turn to the 1-140 of table 111, representation compound is numbered 111-1-111-140.
Table 111
Table 112: in general formula I-A, work as R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=Rb=R
7=R
1=R
2=R
3=R
5during=H, R
4=Cl, substituent A is in table 111, and be corresponding in turn to the 1-140 of table 111, representation compound is numbered 112-1-112-180.
Table 113: in general formula I-A, work as R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=R
7=R
1=R
2=R
3=R
5=H, R
4during=H, substituent A is consistent with table 111, and be corresponding in turn to the 1-140 of table 111, representation compound is numbered 113-1-113-180.
Table 114: in general formula I-A, work as R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=R
7=R
1=R
2=R
3=R
5=H, R
4=CF
3time, substituent A is consistent with table 111, and be corresponding in turn to the 1-140 of table 111, representation compound is numbered 114-1-114-180.
Table 115: in general formula I-B, work as R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=R
7=R
1=R
2=R
3=R
5=H, R
4=CH
3time, substituent A is consistent with table 111, and be corresponding in turn to the 1-140 of table 111, representation compound is numbered 115-1-115-180.
Table 116: in general formula I-B, work as R
8'=CH
3, R
9=CH
3, R
10=Cl, R
a=R
b=R
7=R
1=R
2=R
3=R
5=H, R
4=OCH
3time, substituent A is consistent with table 111, and be corresponding in turn to the 1-140 of table 111, representation compound is numbered 116-1-116-180.
The preparation method of compound of Formula I of the present invention is as follows, the preparation of general formula I I and III compound can be prepared with reference to compound of Formula I method, and difference starting raw material is replaced 6-chlorine apellagrin (M-1) be changed to replacement 2-chloroisonicotinic acid and replace 2-chlorine apellagrin.
Compound of Formula I of the present invention is prepared in accordance with the following methods, and reaction formula is as follows, and in formula, each group unless otherwise indicated defines ditto:
Intermediate H and L is obtained by reacting compound of Formula I in the basic conditions in suitable solvent.
The suitable optional potassium hydroxide freely of alkali, sodium hydroxide, sodium carbonate, salt of wormwood, sodium bicarbonate, triethylamine, pyridine, sodium methylate, sodium ethylate, sodium hydride, potassium tert.-butoxide or sodium tert-butoxide etc.
React and carry out in suitable solvent, the suitable optional tetrahydrofuran (THF) freely of solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile, toluene, dimethylbenzene, benzene, DMF, N-Methyl pyrrolidone, methyl-sulphoxide, acetone or butanone etc.
Temperature of reaction between room temperature to solvent boiling point temperature, can be generally 20-100 DEG C.
Reaction times is 30 minutes to 20 hours, usual 1-10 hour.
Intermediate L is commercially available or press known method preparation, concrete preparation can refer to document Annalen der Chemie JustusLiebig ' s, 536,97(1938), Bull.Soc.Chim.France, 293 (1966), the method preparation that describes such as US4950668, JP2292263, JP2053776, JP4069361 or JP4069379.
Intermediate H is different according to A, B definition, is divided into following three kinds of situations preparation:
The first situation:
As A=H,
1) the carbon nitrogen singly-bound that is directly connected of B=amide nitrogen atom and pyridine ring 3,4 or 5 carbon atoms, referring to the method preparation described in patent WO9924404.
2) B=-CH
2cR
ar
bin-time, referring to the method preparation described in patent WO9404527, US20110054173 or WO2011022.Or be prepared as follows:
In formula, U is leavings group, is halogen or hydroxyl etc.
Intermediate H-1 and H-2, under suitable alkali exists, at suitable temperature, reacts 30 minutes to 20 hours, usual 1-10 hour, obtained intermediate H-3 in suitable solvent; H-3 obtains H-4 through red aluminium reducing, and this step working method is referring to patent EP1840128; H-4 and sulfur oxychloride react obtained H-5, and this is normal experiment method; H-5 and sodium cyanide react, obtained H-6, this step working method referring to patent WO2007045989, WO2009115257, according to Journal of OrganicChemistry, 71 (21), 8023-8027; 2006, 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, obtains H-7 by H-6; Finally, H-7 obtains intermediate H through hydrogenating reduction at suitable catalyzer under existing with ammoniacal liquor, and concrete preparation can reference literature 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, the method p.18 described in (1947) is carried out.Suitable catalyzer can be selected from Raney's nickel, palladium carbon or platinum oxide etc.
Intermediate source is as follows: intermediate H-1 and H-2 all has commercially available, or conventionally prepares.
The suitable optional potassium hydroxide freely of alkali, sodium hydroxide, sodium carbonate, salt of wormwood, sodium bicarbonate, triethylamine, pyridine, sodium methylate, sodium ethylate, sodium hydride, potassium tert.-butoxide or sodium tert-butoxide etc.
React and carry out in suitable solvent, the suitable optional tetrahydrofuran (THF) freely of solvent, Isosorbide-5-Nitrae-dioxane, acetonitrile, toluene, dimethylbenzene, benzene, DMF, N-Methyl pyrrolidone, methyl-sulphoxide, acetone or butanone etc.
Temperature of reaction between room temperature to solvent boiling point temperature, can be generally 20-100 DEG C.
Reaction times is 30 minutes to 20 hours, usual 1-10 hour.
3) B=-CH
2cR
ar
bcR
ar
bin-time, preparation method is as follows:
H-8 is prepared with reference to Synthesis, (9), 727-9 by H-7; 1983 or Tetrahedron Letters, 39 (51), 9455-9456; The method described in 1998 is carried out; The same B=-CH of H-13 method is prepared by H-8
2cR
ar
b-time corresponding steps.
The second situation:
As A ≠ H, be that raw material obtains by the intermediate of A=H, concrete operations are carried out see the method described in WO2004093800A.
General formula I, II or Ш compound demonstrate excellent activity to the multiple germ in agricultural or other field, also demonstrate good activity to insect evil mite.Therefore, technical scheme of the present invention also comprises the purposes that general formula I, II or Ш compound are used as to prepare sterilant, insecticidal/acaricidal agent in agricultural or other field.
The example of the disease mentioned below is only used for the present invention is described, but never limits the present invention.
General formula I, II or Ш compound can be used for preventing and treating following disease: oomycetes diseases, as oidium (cucumber downy mildew, oilseed rape downy mildew, downy mildew, beet oidium, downy mildew of sugarcane, tobacco downy mildew, pea oidium, sponge gourd oidium, wax gourd oidium, muskmelon downy mildew, cabbage oidium, downy mildew of spinach, radish oidium, downy mildew of garpe, onion mildew), white rust (white rust of colza, cabbage white blister), samping off (rape samping off, Tobacco seedling diseases, tomato samping off, capsicum samping off, eggplant samping off, cucumber samping off, cotton seedling samping off), phytophthora rot (capsicum phytophthora rot, sponge gourd phytophthora rot, wax gourd phytophthora rot), epidemic disease (broad bean epidemic disease, Cucumber Blight, pumpkin epidemic disease, wax gourd epidemic disease, watermelon epidemic disease, muskmelon blight, capsicum epidemic disease, leek epidemic disease, garlic epidemic disease, Cotton blight), late blight (the late blight of potato, tomato late blight) etc., imperfect fungi disease, as blight (sweet potato blight, cotton wilt, sesame blight, castor-oil plant blight, tomato wilt, Kidney bean blight, cucumber fusarium axysporum, sponge gourd blight, pumpkin blight, wax gourd blight, watermelon blight, Muskmelon Fusarium wilt, capsicum wilt, faba bean Fusarium wilt, rape blight, soybean Fusariuming disease), root rot (Fusarium solani, Fructus Solani melongenae root maize ear rot, Bean Root maize ear rot, cucumber root rot, Root of Balsampear maize ear rot, cotton black root rot, root rot of Vicia faba), damping-off (cotton seedling blight, sesame damping-off, capsicum damping-off, cucumber rhizoctonia rot, Chinese cabbage damping-off), anthrax (anthracnose of sorghum, cotton anthracnose, bluish dogbane anthrax, jute anthrax, anthracnose of flax, Colletotricum destructivum, mulberry anthrax, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, balsam pear anthrax, summer squash anthrax, wax gourd anthrax, watermelon anthrax, muskmelon anthrax, lichee anthrax), verticillium (cotton verticillium wilt, Sunflower Receptacle verticillium, tomato verticillium, capsicum verticillium, eggplant verticillium wilt), black spot (summer squash black spot, wax gourd black spot, muskmelon black spot), gray mold (cotton boll gray mold, bluish dogbane gray mold, graw mold of tomato, Botrytis cinerea, Kidney bean gray mold, celery gray mold, spinach gray mold, Kiwifruit gray mold), brown spot (cotton brown spot, jute brown spot, beet cercospora leaf spot, the cercospora brown spot of peanut, capsicum brown spot, wax gourd brown spot, Soybean Brown Spot pinta, septorial brown spot of sunflower, pea brown spot, broad bean brown spot), black spot (the false black spot of flax, alternaria stem rot of colza, sesame black spot, Sunflower Receptacle black spot, castor-oil plant black spot, tomato black spot, capsicum black spot, eggplant black spot, Kidney bean black spot, cucumber black spot, celery black spot, carrot black rot, black rot of carrot, melanose or canker of apple, the cercospora black spot of peanut), spot blight (spotted wilt of tomato, cayenne pepper spots rot, celery septoria disease), early blight (early blight of tomato, capsicum early blight, eggplant early blight, target, early blight of celery), ring spot (soybean ring spot, sesame ring spot, Kidney bean ring spot), leaf blight (sesame leaf rot, Sunflower Leaf rot, watermelon leaf rot, Muskmelon leaf rot), base rot disease (tomato base rot disease, Kidney bean base rot disease), and other (Helminthosporium carbonum, bluish dogbane waist folding is sick, rice blast, the black sheath of chestnut is sick, sugarcane eye spot, cotton boll aspergillosis, peanut crown rot, soybean stem rot, soybean diplostomiasis, muskmelon leaf blight, Peanut Web Blotch Disease, the red leaf spot of tea, pepper white star disease, Leaf of Chinese Waxgourd pinta, celery Black Rotten, spinach heartrot, bluish dogbane leaf mold, bluish dogbane spot disease, jute stem pinta, purple spot of soybean, Alternaria sesami, castor-oil plant graywall, dark brown leaf spot, cercospora leaf spot of egg plant, Kidney bean red spot disease, balsam pear leukodermia, watermelon spot disease, jute withered rotten disease, Sunflower Root stem rot, Kidney bean charcoal rot, soybean target spot is sick, eggplant rod spore leaf spot, Leaf Spot Caused by Corynespora cassiicola on Cucumber, leaf muld of tomato, eggplant leaf mold, broad bean reddish macules etc.) etc., basidiomycetes disease, as rust (stripe rust of wheat, the stem rust of wheat, wheat leaf rust, Peanut Rust, rust of sunflower, sugarcane rust, leek rust, rust of onion, chestnut rust, soybean rust), smut (maize head smut, corn smut, head smut of sorghum, sorghum loose smut, covered kernel smut of kaoliang, high beam column smut disease, chestnut kernel smut, smut of sugarcane, Bean rust disease) and other (as wheat hypochnus, rice sheath blight diseases etc.) etc., ascomycetes disease, as Powdery Mildew (wheat powdery mildew, rape Powdery Mildew, sesame Powdery Mildew, Sunflower Receptacle Powdery Mildew, beet powdery mildew, eggplant Powdery Mildew, powdery mildew of pea, sponge gourd Powdery Mildew, squash marble dust, Pumpkin powdery mildew, wax gourd Powdery Mildew, melon powdery mildew, uncinula necator, broad bean Powdery Mildew), sclerotium disease (flax sclerotium disease, sclerotinia rot of colza, soybean sclerotinia crown rot, peanut sclerotium disease, tobacco sclerotium disease, capsicum sclerotium disease, eggplant sclerotium disease, bean sclerotinia rot, pea sclerotium disease, cucumber timberrot, balsam pear sclerotium disease, wax gourd sclerotinia, watermelon sclerotium disease, celery sclerotium disease), black spot (scab of apple, pear scab) etc.Especially, to corn rust, rice blast, gray mold of cucumber and cucumber downy mildew, at lower doses still there is good prevention effect.
General formula I, II or Ш compound can be used for preventing and treating following insect: Coleoptera (Coleoptera) (beetle): bean weevil belongs to kind of (Acanthoscelides spp.) (curculionid), acanthoscelides obtectus (Acanthoscelides obtectus) (common pea weevil), Emerald ash borer (Agrilus planipennis) (emerald ash borer, Agrilus planipennis), acupuncture needle Eimeria kind (Agriotes spp.) (wireworm), Anoplophora glabripenis (Anoplophora glabripennis) (Asia psacotheahilaris), cotton boll resembles and belongs to kind of (Anthonomus spp.) (Culculionidae), Mexico's cotton boll resembles (Anthonomus grandis) (bollworm), cocoon honeybee belongs to kind of (an Aphidius spp.), weevil belongs to kind of (Apion spp.) (curculionid), sugarcane cockchafer belongs to kind of (Apogonia spp.) (grub), black suede cockchafer (Atacnius sprctulus) (smaller velvety chafer), Atomaria linearis (Atomaria linearis) (little beet beetle (pygmy mangold beetle), cucumber beetle belongs to kind of (an Aulacophore spp.), beet resembles (Bothynoderes punctiventris) (beet tails curculionid), bean weevil belongs to kind of (Bruchus spp.) (curculionid), pea weevil (Bruchuspisorum) (pea weevil), Cacoesia belongs to kind of (a Cacoesia spp.), Callosobruchus maculatus (Callosobruchus maculatus) (southern cowpea curculionid), pineapple bug (Carpophilus hemipteras) (dried-frait beetle), beet tortoise beetle (Cassida vittata), it Bos kind (Ccrostcrna spp.), Ccrotoma belongs to kind of (Ccrotoma spp.) (chrysomonad (chrysomcids)), beans chrysomelid (Cerotomatrifur cata) (the chrysomelid worm of beans), tortoise resembles and belongs to kind of (Ceutorhynchus spp.) (curculionid), Chinese cabbage seed tortoise resembles (Ceutorhynchusassimilis) (Chinese cabbage weevil (cabbage seedpod weevil)), turnip tortoise resembles (Ceutorhynchus napi) (Caulis et Folium Brassicae capitatae curculionid (cabbage curculio)), phyllotreta kind (Chaetocnema spp.) (chrysomonad), Colaspis belongs to kind of (Colaspis spp.) (a native beetle), Conoderus scalaris, Conoderus stigmosus, Lee resembles (Conotrachelus nenuphar) (plum cone weevil), Cotinusnitidis (Green june beetle (Green June beetle)), officinalis scotellaris (Crioceris asparagi) (officinalis beetle), rusty grain beetle (Cryptolestes ferrugincus) (rust paddy beetle (rusty grainbeetle)), Cryptolestes pusillus (Cryptolestes pusillus) (flat ostomatid), Cryptolestes turcicus Grouville (Cryptolestes turcicus) (Turkey paddy beetle (Turkish grain beetle)), Ctenicera belongs to kind of (Ctenicera spp.) (nematode), Curculio kind (Curculio spp.) (curculionid), round end rhinoceros cockchafer belongs to kind of (Cyclocephala spp.) (grub), close some withe resembles (Cylindrocpturus adspersus) (Sunflower Receptacle grass curculionid (sunflower stem weevil)), mango leaf-cutting resembles (Deporaus marginatus) (mango leaf-cutting curculionid (mango leaf-cutting weevil)), lader beetle stupid (Dermesteslardarius) (lader beetle is stupid), white abdomen skin stupid (Dermestes maculates) (white abdomen skin is stupid), chrysomelid genus kind of (Diabrotica spp.) (chrysomelid), mexican bean ladybird (Epilachna varivcstis) (Mexico beans beetle), moth stem weevil (raustinus cubae), pale collar resembles (Hylobius pales) (pales weevil (pales weevil)), Phytonomus kind (Hypera spp.) (curculionid), alfalfa leaf resembles (Hyperapostica) (alfalfa weevil), Hyperdoes belongs to kind of (Hyperdoes spp.) (Argentinian stem weevil (a Hyperodes weevil)), coffee cherry little stupid (Hypothenemus hampei) (coffee cherry beetle), little stupid genus kind of (Ips spp.) (sour jujube shin little stupid (engravers)) of tooth, lasioderma serricorne (Lasioderma serricorne) (cigarette beetle), colorado potato bug (Leptinotarsa decemlineata) (Colorado potato beetle), Liogenys fuscus, Liogenys suturalis, rice water weevil (Lissorhoptrus oryzophilus) (rice water weevil), the stupid genus of powder kind of (Lyctus spp.) (the stupid beetle of wooden stupid moth/powder (powder post beetles)), Maecolaspis joliveti, Megascelis belong to kind of (a Megascelis spp.), corn click beetle (Melanotus communis), nitidulid belongs to kind of (Meligethesspp.), rape nitidulid (Meligethes aeneus) (brevitarsis (blossom beetle)), May beetle (Melolonthamelolontha) (typical European chafer), Oberea brevis, linear cylinder longicorn (Oberea linearis), coconut palm moth rhinoceros cockchafer (Oryctesrhinoceros) (date palm beetle (date palm beetle)), trade saw-toothed grain beetle (Oryzaephilus mercator) (market saw-toothed grain beetle (merchant grain beetle)), saw-toothed grain beetle (Oryzaephilus surinamensis) (sawtooth paddy beetle (sawtoothcd grainbcctlc)), beak weevil belongs to kind of (Otiorhynchus spp.) (curculionid), black angle scotellaris (Oulema melanopus) (cereal leaf beetle (cereal leafbeetle)), Oulema oryzae (Oulema oryzae), the short beak of rose resembles and belongs to kind of (Pantomorus spp.) (curculionid), food phyllobranchia cockchafer belongs to kind of (a Phyllophaga spp.) (May/June chafer), Phvllophaga cuyabana, striped flea beetle kind (Phyllotreta spp.) (chrysomonad), apple tiger resembles and belongs to kind of (a Phynchites spp.), Japan popillia flavosellata fairmaire (Popillia japonica) (Japanese beetle), large space between muscles stupid (Prostephanus truncates) (large space between muscles long stupid (larger grain borer)), paddy stupid (Rhizoperthadominica) (the little moth of paddy (lesser grain borer)), root gill cockchafer belongs to kind of (Rhizotrogus spp.) (European chafer (Eurpoeanchafer)), Rhynchophorus kind (Rhynchophorus spp.) (curculionid), little stupid genus kind of (Scolytus spp.) (wooden stupid moth), Shenophorus belongs to kind of (Shenophorus spp.) (grain weevil), pea leaf resembles (Sitona lincatus) (pealeaf weevil (pca leafweevil)), Sitophilus kind (Sitophilus spp.) (grain weevil first), grain weevil (Sitophilus granaries) (paddy worm (granary weevil)), rice weevil (Sitophilus oryzae) (rice weevil first (rice weevil)), medicinal material ostomatid (Stegobium paniceum) (Stegobium paniceum (drugstore beetle)), Tribolium kind (Tribolium spp.) (flour beetle), red flour beetle (Tribolium castaneum) (red flour beetle (red flour beetle)), assorted plan paddy moistens (Tribolium confusum) (confused flour beetle (confused flour beetle)), piebald skin stupid (Trogoderma variabile) (warehouse skin stupid (warehouse beetle)) and Zabrus tenebioides.
Dermaptera (Dcrmaptcra) (earwig).
Neuroptera (Dictyoptera) (cockroach): Groton bug (Blattella germanica) (Groton bug (German cockroach)), oriental cockroach (Blatta orientalis) (Blatta seu periplaneta), Pennsylvania wood Lian (Parcoblatta pennylvanica), periplaneta americana (Periplaneta americana) (America roach consumptive disease (American cockroach)), Australian cockroach (Periplaneta australoasiae) (Australian cockroach (Australian cockroach)), periplaneta brunnea (Pcriplancta brunnca) (periplaneta brunnea (brown cockroach)), smoke Perilpaneta americana (Periplaneta fuliginosa) (Peroplaneta fluligginosa (smokybrown cockroach)), the green blattaria of sugarcane (Pyncoselussuninamensis) (sugarcane Lian (Surinam cockroach)) and long palpus blattaria (Supella longipalpa) (brown band blattaria (brownbandedcockroach)).
Diptera (Diptera) (fly): Aedes kind (Aedes spp.) (mosquito), alfalfa is dived fly (Agromyza frontella) (alfalfa dive fly (alfalfa blotch leafminer)), Hippelates kind ((Agromyza spp.) (Liriomyza), by Anastrepha kind (Anastrephaspp.) (fruit bat), Caribbean is by trypetid (Anastrepha suspensa) (Caribbean is by trypetid (Caribbean fruit fly)), Anopheles kind (Anopheles spp.) (mosquito), Bactrocera kind (Batrocera spp.) (fruit bat), melon trypetid (Bactrocera cucurbitae) (melon fly), citrus fruit fly (Bactrocera dorsalis) (oriental fruit fly), little bar Anastrepha kind (Ceratitis spp.) (fruit bat), the little bar trypetid in Mediterranean Sea (Ceratitis capitata) (medfly), Chrysops kind (Chrysops spp.) (deer horsefly), Callitroga's kind (Cochliomyiaspp.) (screw worm fly larva), Ying uranotaenia kind (Contarinia spp.) (Ying mosquito), Culex kind (Culex spp.) (mosquito), Ye Ying uranotaenia kind (Dasineura spp.) (Ying mosquito), You Cai Ye Ying mosquito (Dasineura brassicae) (Juan Xin Cai Ying mosquito), Delia kind (Delia spp.), delia platura (Delia platura) (root maggot (seedcorn maggot)), Drosophila kind (Drosophila spp.) (vinegar fly), Fannia kind (Fannia spp.) (housefly), anthomyia canicularis (Fannia canicularis) (Fannia canicularis (little house fly)), anthomyia scalaris (Fannia scalaris) (anthomyia scalaris), large horse botfly (Gasterophilus intestinalis) (horse botfly), Gracillia perseae, Haematobia irritans (Haematobia irritans) (horn fly), Hylemyia kind (Hylemyia spp.) (root maggot (root maggot)), heel fly (Hypoderma lineatum) (laiu wire rope torsalo (common cattle grub)), Liriomyza kind (Liriomyza spp.) (Liriomyza), wild cabbage liriomyza bryoniae (Liriomyza brassica) (Liriomyza that crawls (serpentine leafminer)), sheep hippoboscid (Melophagusovinus) (sheepked), fly belongs to kind of (Musca spp.) (housefly (a muscid fly)), face fly (Musca autumnalis) (face fly (facefly)), housefly (Vusca domestica) (housefly (house fly)), Oestrus ovis (Oestrus ovis) (sheep nose fly (sheep bot fly)), Europe frit fly (Oscinella frit) (Oscinella frit), beet spring fly (Pegomyia betae) (spinach leaf miner (beetleafminer)), wheat fly belongs to kind of (a Phorbia spp.), carrot fly (Psila rosae) (Radix Dauci Sativae rust fly (carrotrust fly)), cherry fruit bat (Rhagoletis cerasi) (cherry fruit bat (cherry fruit fly)), Rhagoletis pomonella (Rhagoletis pomonella) (apple maggots (apple maggot)), wheat midge (Sitodiplosis mosellana) (orange wheat flower mosquito (orange wheat blossommidge)), tatukira (stomoxys calcitruns) (tatukira (stable fly)), the gadfly belongs to kind of (Tahanus spp.) (horse botfly) and a large uranotaenia kind (Tipula spp.) (daddy-longlegs).
Hemiptera (Hemiptera) (stinkbug): intend green stinkbug (Acrosternum hilare) (green stinkbug (green stink bug)), America paddy chinch bug (Blissus leucopterus) (chinch bug (chinch bug)), potato pretty fleahopper (Calocoris norvegicus) (potato fleahopper (potato mirid)), cimex hemipterus (Cimex hemipterus) (cimex hemipterus (tropical bed bug)), bedbug (Cimexlectularius) (bedbug (bed hug)), Daghertus fasciatus, Dichelops furcatus, cotton the red stinkbug of black wing (Dysdercussuturellus) (red cotton bug (cotton stainer)), Edessa meditabunda, Europe Eurygasterspp (Eurygaster maura) (paddy worm (cerealbug)), Euschistus heros, brown smelly stinkbug (Euschistus servus) (brown stinkbug (brown stink bug)), iS-One angle fleahopper (Helopeltis antonii), tea angle fleahopper (Helopeltis theivora) (tea blight plantbug), stinkbug belongs to kind of (Lagynotomus spp.) (stinkbug), large Leptocorisa spp (Leptocorisa oratorius), different Leptocorisa spp (Leptocorisa varicornis), Lygus Hahn kind (Lygusspp.) (fleahopper (plant bug)), beanpod lygus bug (Lygus hesperus) (western tarnished plant bug), the graceful powder stinkbug of the rose of Sharon (Maconellicoccus hirsutus), Neurocolpus longirostris, Nezara viridula smaragdula Fabricius. (Nezara viridula) (southern green stinkbug), Phytocoris kind (PhyLocoris spp.) (fleahopper), fleahopper (Phytocoris californicus) is planted in California, Phytocoris relativus, Piezodorus guildingi, four line fleahoppers (Poecilocapsus lineatus) (fourlined plant bug), Psallus vaccinicola, Pseudacysta perseae, Scaptocoris castanea and Triatoma kind (Triatoma spp.) (cone nose worm (bloodsuckingconenose bug) of sucking blood/hunt stinkbug (kissing bug)).
Homoptera (Homoptera) (aphid, a red-spotted lizard, aleyrodid, leafhopper): acyrthosiphum pisim (Acrythosiphonpisum) (acyrthosiphum pisim (peaaphid)), adelgid belongs to kind of (Adelges spp.) (adelgids), wild cabbage aleyrodid (Aleurodes proletella) (Caulis et Folium Brassicae capitatae aleyrodid), Aleurodicus dispersus (Aleurodicus disperses), velvet aleyrodid (Aleurothrixus flccosus) (whitefly in bt cotton (woolly whitefly)), white wheel armored scale belongs to kind of (an Aluacaspis spp.), Amrasca bigutella bigutella, froghopper belongs to kind of (Aphrophora spp.) (leafhopper (leafhopper)), California red scale (Aonidiella aurantii) (the red a red-spotted lizard in California (California red scale)), Aphis kind (Aphis spp.) (aphid), cotten aphid (Aphis gossypii) (cotton aphid), apple aphid (Aphis pomi) (apple aphid), eggplant is without net aphid (Aulacorthitm solani) (foxglove aphid (foxglove aphid)), Aleyrodes kind (Bemisia spp.) (aleyrodid), Bemisia argentifolii (Bemisia argentifolii), sweet potato whitefly (Bemisia tabaci) (sweetpotato whitefly), Diuraphis noxia (Brachycolusnoxius) (Russian aphid (Russian aphid)), officinalis tubule aphid (Brachycorynclia asparagi) (officinalis aphid (asparagusaphid)), Brevennia rehi, brevicoryne brassicae (Brevicoryne brassicae) (Caulis et Folium Brassicae capitatae aphid), lecanium belongs to kind of (Ceroplastesspp.) (a red-spotted lizard), ceroplastes rubens (Ceroplastes rubens) (red wax scale), snow armored scale belongs to kind of (Chionaspis spp.) (a red-spotted lizard), Aspidiotus belongs to kind of (Chrysomphalus spp.) (a red-spotted lizard), soft wax a red-spotted lizard belongs to kind of (Coccus spp.) (a red-spotted lizard), the pink bad aphid (Dysaphisplantaginea) of apple (rosy apple aphid), green jassids belongs to kind of (Empoasca spp.) (leafhopper), apple aphid (Eriosomalanigerum) (woolly apple aphid), blow cotton a red-spotted lizard (Icerya purchasi) (cottony cushion scale), mango yellow line leafhopper (Idioscopus nitidulus) (mango leafhopper), small brown rice planthopper (Laodelphax striatellus) (smaller brownplanthopper), lepidosaphes shimer kind (Lepidosaphes spp.), long tube Aphis kind (Macrosiphum spp.), root of Beijing euphorbia Macrosiphus spp (Macrosiphum euphorbiae) (potato aphid (potato aphid)), grain aphid (Macrosiphum granarium) (Britain's wheat aphid (English grain aphid)), rose aphid (Macrosiphum rosae) (rose aphid (rose aphid)), four line leafhopper (Macrosteles quadrilineatus) (Aster tataricus leafhopper (aster leafhopper)), Mahanarva frimbiolata, Acyrthosiphon dirhodum (Metopolophium dirhodum) (rose wheat aphid (rose grain aphid)), Midis longicornis, black peach aphid (Myzuspersicae) (black peach aphid (green peach aphid)), rice green leafhopper belongs to kind of (Nephotettix spp.) (leafhopper), rice green leafhopper (Nephotettix cinctipes) (greenery cicada (green leafhopper)), brown paddy plant hopper (Nilaparvata lugens) (brownplanthopper), chaff sheet armored scale (Parlatoria pergandii) (chaff scale), ebony armored scale (Parlatoria ziziphi) (ebonyscale), popcorn wing plant hopper (Peregrinus maidis) (corn delphacid), froghopper belongs to kind of (Philaenus spp.) (spittle insects), grape phylloxera (Phylloxera vitifoliae) (grape phylloxera), Physokermes piceae (Physokermes piceae) (spruce budscale), stern line mealybug belongs to kind of (Planococcus spp.) (mealybug), mealybug belongs to kind of (Pseudococcus spp.) (mealybug), the clean mealybug of pineapple (Pscudococcus brcvipcs) (pinc apple mcalybug), theatre armored scale (Quadraspidiotus perniciosus) (san jose scale (San Jose scale)), aphid a red-spotted lizard belongs to kind of (Rhapalosiphum spp.) (aphid), corn tree louse (Rhapalosiphum maida) (corn leaf aphids (corn leaf aphid)), rhopalosiphum padi (Rhapalosiphum padi) (oatbird-cherry aphid), pearl lecanium belongs to kind of (Saissetia spp.) (a red-spotted lizard), olive pearl lecanium (Saissetia oleae) (black a red-spotted lizard), green bugs (Schizaphis graminum) (green bugs (gr eenbug)), grain aphid (Sitobion avenge) (Britain's wheat aphid), white backed planthopper (Sogatella furcifera) (white-backedplanthopper), variegation Aphis kind (Therioaphis spp.) (aphid), line lecanium belongs to kind of (Toumeyella spp.) (a red-spotted lizard), sound Aphis kind (Toxoptera spp.) (aphid), trialeurodes vaporariorum belongs to kind of (Trialeurodes spp.) (aleyrodid), Trialeurodes vaporariorum Westwood (Trialeurodesvaporariorum) (greenhouse whitefly (greenhouse whitefly)), knot wing trialeurodes vaporariorum (Trialeurodesabutiloneus) (bandedwing whitefly), point armored scale belongs to kind of (Unaspis spp.) (a red-spotted lizard), vow sharp clam (Unaspisyanonensis) (arrow a red-spotted lizard (arrowhead scale)) and Zulia entreriana.
Hymenoptera (Hymenoptera) (ant, wasp and honeybee): Myrmecina kind (Acromyrrmex spp.), Xinjiang cabbage sawfly (Athalia rosae), leaf ant belongs to kind of (Atta spp.) (an Ieafcutting ants), black ant belongs to kind of (Camponotus spp.) (carpented ant (carpenterant)), Diprion kind (Diprion spp.) (sawfly (sawfly)), ant belongs to kind of (Formica spp.) (ant), Argentine ant (Iridomyrmex humilis) (Argentineant), Monomorium subspecies (Monomorium ssp.), MonomoriumMayr (Monomoriumminumum) (little black ant), kitchen ant (Monomorium pharaonis) (little red ant (Pharaoh ant)), Neodiprion kind (Neodiprion spp.) (sawfly), Pogonomyrmex kind (Pogonomyrmex spp.) (harvester ant), hornet belongs to kind of (Polistes spp.) (wasp (a paper wasp)), Solenopsis kind (Solenopsis spp.) (fiery ant), odorous antenna (Tapoinoma sessile) (odorous antenna (odoroushouse ant)), Tetramorium kind (Tetranomorium spp.) (Pavement Ant (pavement ant)), Vespula kind (Vespulaspp.) (yellow jacket (yellow jacket)) and Xylocopa kind (Xylocopa spp.) (carpenter bee (carpenter bee)).
Isoptera (Isoptera) (termite): formosanes belongs to kind of (a Coptotcrmcs spp.), bent jaw termite (Coptotermes curvignathus), France termite (Coptotermes frenchii), Coptotermes formosanus Shtrari． (Coptotermes formosanus) (Formosan subterraneantermite), angle Cryptotermes kind (Cornitermes spp.) (proboscis termite (nasute termite)), sand Cryptotermes kind (Cryptotermesspp.) (dry-wood termite), different Cryptotermes kind (Heterotermes spp.) (desert Soil termites (desert subterranean termite)), golden yellow different termite ((IIeterotermes aureus), kalotermitid belongs to kind of (Kalotermes spp.) (dry-wood termite), principal columns of a hall Cryptotermes kind (Incistitermes spp.) (dry-wood termite), Macrotermes kind (Macrotermes spp.) (cultivation termite (fungus growingtermite)), edge kalotermitid belongs to kind of ((Marginitermes spp.) (dry-wood termite), saw Cryptotermes kind (Microcerotermes spp.) (careless termite (harvester termite)), the little termite of rice wheat (Microtermes obesi), former angle Cryptotermes kind (Procornitermes spp.), Reticulitermes kind (Reticulitermes spp.) (Soil termites), Reticulitermes banyulensis, meadow reticulitermes flavipe (Reticulitermes grassei), yellow limb reticulitermes flavipe (Reticulitermes flavipes) (east Soil termites), beautiful little Huang reticulitermes flavipe (Reticulitermes hageni), west reticulitermes flavipe (Reticulitermes hesperus) (west Soil termites), Sang Te reticulitermes flavipe (Reticulitermes santonensis), dwell northern reticulitermes flavipe (Reticulitermes speratus), U.S. black shin reticulitermes flavipe (Reticulitermestibialis), U.S. little black reticulitermes flavipe (Reticulitermes virginicus), proboscis Reticulitermes kind (Schedorhinotermes spp.) and ancient Cryptotermes kind (Zootermopsis spp.) (rotten kalotermitid).
Lepidopteran (Lepidoptera) (moth and butterfly): Achoea janata, Adoxophyes spp belongs to kind of (an Adoxophyes spp.), adoxophyes moth (Adoxophyes orana), tiger belongs to kind of (Agrotis spp.) (cutworm) on ground, little cutworm ((Agrotis ipsilon) (black cutworm), cotton leaf ripple noctuid (Alabama argillacea) (cotton leafworm (cotton leafworm)), Amorbia cuneana, Amyelosistransitella (navel orangeworm), Anacamptodes defectaria, sliver gelechiid (Anarsia lineatella) (peach twigborer), jute bridge night high (Anomis sabulijera) (jute looper), Anticarsia (Anticarsia gemmatalis) (velvetbeancaterpillar), fruittree leafroller (Archips argyrospila) (fruit tree leafroller), rose leaf roller (Archips rosana) (rose leaf roller), moth belongs to kind of (Ar gyrotaenia spp.) (a tortricid moths) volume, tangerine Argyrotaenia spp (Argyrotaeniacitrana) (citrus leaf-roller (orange tortrix)), Autographa gamma, Bonagota cranaodcs, Cnaphalocrocis medinali(rice leaf roller) (Borbo cinnara) (rice leaf folder), cotton leaf lyonetid (Bucculatrix thurberiella) (cotton leafperforator), thin moth belongs to kind of (Caloptilia spp.) (leaf miner), Capua reticulana, peach fruit moth (Carposina niponensis) (peach fruit moth (peachfruit moth)), straw borer spp kind (Chilo spp.), Chlumetia transversa Walker (Chlumetia transversa) (mango shootborer), rose Choristoneura spp (Choristoneura rosaceana) (oblique banded leaf roller), Noctua kind (Chrysodeixisspp.), cnaphalocrocis medinalls guenee (Cnaphalocerus medinalis) (meadow leaf roller (grass leafroller)), beans Pier kind (Coliasspp.), lichee litchi (Conpomorpha cramerella), fragrance wooden stupid moth (Cossus cossus) (wooden stupid moth), Crambus Fabricius kind (Crambus spp.) (Sod webworms), Lee's small kernel-eating insect (Cydia funebrana) (Li Guoe (plum fruit moth)), oriental fruit months (Cydia molesta) (east heart-eating worm (oriental fruit moth)), pea moth pod high (Cydia nignicana) (peamoth), the stupid moth of apple (Cydia pomonella) (codling moth (codling moth)), Darna diducta, Diaphania kind (Diaphania spp.) (stem borer (stem borer)), snout moth's larva belongs to kind of (Diatr aea spp.) (stem borer (a stalk bor er)), little sugarcane borer (Diatraea saccharalis) (sugarcane borer), Diatraea grandiosella (Diatraea graniosella) (southwester cornborer), Earias kind (Earias spp.) (bollworm), earias insulana (Earias insulata) (Egyptian bollworm), earias fabia (Earias vit.ella) (rough northern bollworm), Ecdytopopha aurantianum, South America maize seedling phycitid (Elasmopalpus lignosellus) (lesser cornstalk borer), shallow brown apple moth (Epiphysias postruttana) (lightbrown apple moth), meal moth belongs to kind of (Ephestia spp.) (a powder snout moth's larva), meal moth (Ephestia cautella) (almond moth), tobacco powder sp (Ephestia elutella) (tobacco snout moth's larva (tobbaco moth)), Mediterranean flour moth (Ephestiakuehniella) (Mediterranean flour moth), Epimeces belongs to kind of (an Epimeces spp.), steinernema at night (Epinotiaaporema), Skipper of plantains (Erionota thrax) (banana skipper), ligustrum fine tortricidae (Eupoecilia ambiguella) (grape berry moth (grape berry moth)), former cutworm (Euxoa auxiliaris) (army cutworm), Agrotis kind (Feltiaspp.) (cutworm), angle sword Noctua kind (Gortyna spp.) (stem borer), east moth fruit moth (Grapholita molesta) (peach (apricot) sub-heart-eating worm (oriental fruit moth)), treble cut snout moth (Hedylepta indicata) (bean pyralid (bean leaf webber)), blue or green Eimeria kind (Helicoverpa spp.) (noctuid), bollworm (Helicoverpa armigera) (cotton bollworm), paddy real noctuid (Helicoverpa zea) (Pyrausta nubilalis (Hubern). ridge (snout moth's larva ridge worm/bollworm)), Heliothis kind (Heliothis spp.) (noctuid), Heliothis virescens (Heliothis virescens) (tobacco budworm), Hellula undalis (Hellula undalis) (cabbage webworm), Indarbela belongs to kind of (Indarbela spp.) (a root moth), the stupid moth of tomato (Keiferia lycopersicella) (tomato pinworm), the white wing of eggplant wild snout moth's larva (Leucinodes orbonalis) (eggplant fruit borer), pear leaf blister moth (Leucoptera malifoliella), thin moth belongs to kind of (a Lithocollectis spp.), grape olethreutid (Lobesia botrana) (grape fruit moth), Loxagrotis belongs to kind of (Loxagrotis spp.) (noctuid), beans white line cutworm (Loxagrotis albicosta) (western bean cutworm), gypsymoth (Lymantria dispar) (gypsy moth), apple leaf miner (Lyonetiaclerkella) (apple leaf miner (apple leafminer)), oil palm bag moth (Mahasena corbetti) (oil palm bagworm), Malacosoma kind (Malacosoma spp.) (tentcaterpillars), lopper worm (Mamestra brassicae) (dish march moth (cabbage armyworm)), the wild snout moth's larva (Marucatestulalis) of beanpod (the wild snout moth's larva of beans), bag moth (Metisa plana) (bagworm), Mythimna unipuncta (true armyworm), Neoleucinodes elegantalis (little tomato moth (small tomato borer)), 3 water snout moth's larvas (Nymphula depunctalis) (Cnaphalocrocis medinali(rice leaf roller) (rice caseworm)), winter looper (Operophthera brumata) (winter moth), European corn borer (Ostrinianubilalis) (European corn borer (European corn borer)), Oxydia vesulia, the brown volume moth of boundary (Pandemis cerasana) (common glucose leaf roller (common currant tortrix)), apple brown bortrix (Pandemis heparana) (brown apple tortrix), Africa Bodhidharma swallowtail butterfly (Papilio demodocus), Pectinophora gossypiella (Pectinophora gossypiella) (pink bollworm (pink bollworm)), boundary Noctua kind (Peridroma spp.) (cutworm), variegated cutworm (Peridroma saucia) (variegated cutworm), coffee leafminer (Perileucoptera coffeella) (white coffee leafminer), phthorimaea operculella (Phthorimaeaoperculella) (potato tuber moth), citrus leaf lyonetid (Phyllocnisitis citrella), thin moth belongs to kind of (Phyllonorycterspp.) (leaf miner), small white (Pieris rapae) (external cabbage caterpillar (imported cabbageworm)), the first green noctuid of mat (Plathypena scabra), India paddy spot moth (Plodia interpunctella) (Indian meal moth), diamond-back moth (Plutellaxylostella) (diamondback moth), grape berry moth (Polychrosis viteana) (grape berry moth), tangerine fruit ermine moth (Prays endocarps), Fructus oleae europaeae ermine moth (Prsys oleae) (olive moth), mythimna separata belongs to kind of (Pseudaletia spp.) (noctuid), Pseudaletia unipunctata (armyworm), soybean noctuid (Pseudoplusia includens) (soybean looper), looper (Rachiplusia nu), yellow rice borer (Scirpophaga incertulas), high genus at moth stem night kind of (Sesamia spp.) (stem borer), Sesamia inferens (Sesamia inferens) (pink rice stemborer), powder stem snout moth's larva (Sesamia nonagrioides), the brown slug moth of copper stain (Setora nitens), gelechiid (Sitotroga cerealella) (Angoumois grain moth), pilleriana (Sparganothispilleriana), Spodoptera kind (Spodoptera spp.) (armyworm), beet armyworm (Spodoptera exigua) (beet armyworm (beet armyworm)), noctuid (Spodoptcra fugipcrda) (armyworm in autumn (fall armyworm)) is coveted on meadow, south spodoptera (Spodoptera oridania) (southern armyworm (southern armyworm)), emerging Noctua kind (Synanthedonspp.) (root moth), Thecla basilides, Thermisia gemmatalis, casemaking clothes moth (Tineola bisselliella) (webbing clothesmoth), cabbage looper (Trichoplusia ni) (cabbage looper), Liriomyza brponiae (Tuts absoluta), Yponomeuta kind (Yponomeuta spp.), the stupid moth of coffee leopard (Zeuzeracoffeae) (red branch borer) and Zeuzera pyrina (the stupid moth of pears leopard (leopard moth)).
Mallophaga ((Mallophaga) poultry louse (chewing lice)): sheep poultry louse (Bovicola ovis) (sheep biting louse), fiery menopon gallinae (Menacanthus stramineus) (chick poultry louse (chicken body louse)) and shaft louse (Menopongallinea) (common hen house (common hen house)).
Orthoptera (Orthoptera) (grasshopper, locust and cricket): blackspot arna Zhong (Anabrus simplex) (rub a katydid (Mormoncricket)), mole cricket (Gryllotalpidae) (mole cricket (mole cricket)), Asiatic migrotory locust (Locusta migratoria), grasshopper belongs to kind of (Melanoplus spp.) (grasshopper), guiding principle wing spinelet Zhong (Microcentrum retinerve) (angle wing katydid (angular wingedkatydid)), Pterophylla belongs to kind of (Pterophylla spp.) (katydid), chistocerca gregaria, fork-tail katydid (Scudderiafurcata) (fork-tail shrubbery tree Zhong (fork tailed bush katydid)) and black angle oncus locust (Valanga nigricorni).
Anoplura (Phthiraptera) (sucking lice (sucking louse)): sucking louse belongs to kind of (Haematopinus spp.) (ox louse and a pig lice), sheep jaw lice (Linognathus ovillus) (sheep lice (sheep louse)), head louse (Pediculus humanus capitis) (body louse), pediculus humanus corporis (Pediculus humanus humanus) (body louse) and crab louse (Pthirus pubis) (crab louse (crab louse)).
Siphonaptera (Siphonaptera) (flea): ctenocephalides canis (Ctenocephal ides canis) (dog flea), ctenocephalides felis (Ctenocephalides felis) (cat flea) and Pulex irritans (Pulex irritans) (human flea).
Thysanoptera (thrips): cigarette brown thrip (Frankliniella fusca) (tobacco thrip), western classical architecture (Frankliniellaoccidentalis) (western flower thrips), Frankliniella shultzei, Williams flower thrips (Frankliniellawilliamsi) (corn thrips (corn thrip)), greenhouse thrips (IIeliothrips haemorrhaidalis) (greenhouse thrip), Riphiphorothrips cruentatus, hard Thrips kind (Scirtothrips spp), balloonflower root thrips (Scirtothrips cirri) (citrusthrip), Scirothrips dorsalis (Scirtothrips dorsalis) (yellow tea thrips), Taeniothrips rhopalantennalis and Thrips kind (Thrips spp.).
Thysanura (Thysanura) (moth (bristletail)): silverfish belongs to kind of (Lepisma spp.) (stupid worm (silverfish)) and special mess silverfish belongs to kind of (Thermobia spp.) (a special mess fish).
Acarina (Acarina) (mite (mite) and cicada (tick)): Wu Shi honeybee shield mite (Acarapsis woodi) (honeybee Tracheal mite (tracheal mite of honeybee)), Tyroglyphus kind (Acarus spp.) (food mites), Acarus siro (Acarus siro) (paddy mite (grainmite)), mango bud mite (Aceria mangiferae) (mango bud mite), peronium Eriophyes kind (Aculops spp.), Aculops lycopersici (Aculops lycopersici) (tomato russet mite), Aculops pelekasi, tangerine peronium goitre mite (Aculus pelekassi), Si Shi stings goitre mite (Aculus schlechtendali) (apple thorn goitre mite (apple rust mite)), lone star tick (Amblyommaamcricanum) (lone star tick), Boophilus kind (Boophilus spp.) (tick), avette short hairs tick (Brevipalpusobovatus) (privet mite), purplish red short hairs mite (Brevipalpus phoenicis) (red and black flat mite), fat tick belongs to kind of (Demodex spp.) (a mange mites), Dermacentor kind (Dermacentorspp.) (hard tick), America dog tick (Dermacentorvariabilis) (american dog tick), dermatophagoides pteronyssinus (Dermatophagoides pteronyssinus) (house dust mite), Eotetranychus kind (Eotetranycus spp.), Eotetranychus carpini (Eotetranychus carpini) (yellow spider mite (yellow spider mite)), Epitrimerus kind (Epitimerus spp.), Eriophyes kind (Eriophyes spp.), hard tick belongs to kind an of (work, odes spp.) (tick), Panonychus citri belongs to kind of ((a Metatetranycus spp.), notoedres cati (Notoedres cati), Oligonychus kind (Oligonychus spp.), coffee unguiculus mite (Oligonychus coffee), ilex Oligonychus (Oligonychus ilicus) (southernred mi te), Panonychus citri belongs to kind of (a Panonychus spp.), Jie-Li enzyme-SQ (Panonychus cirri) (orange spider (citrus red mite)), panonychus ulmi (Panonychus ulmi) (European red spider (European red mite)), tangerine wrinkle leaf thorn goitre (Phyllocoptruta oleivora) (citrusrust mite), Polyphagotarsonemus latus Banks (Polyphagotarsonemun latus) (broad mite (broad mite)), brown dog tick (Rhipicephalus sanguineus) (brown dog tick (brown dog tick)), root mite belongs to kind of (Rhizoglyphus spp.) (root mite (bulbmite)), itch mite (Sarcoptes scabiei) (itch mite), avocado apical cap goitre mite (Tegolophus perseaflorae), Tetranychus kind (Tetranychus spp.), T.urticae Koch (Tetranychus urticae) (2 spider mites (twospotted spider mite)) and Di Shi watt of mite (Varroa destructor) (honeybee mite).
Nematoda (nematode): Aphelenchoides kind (Aphelenchoides spp.) (bud and leaf and pine wood nematode (bud and leaf & pine wood nematode)), thorn Turbatrix kind (Belonolaimus spp.) (sting nematodes), little loop wire Eimeria kind (Criconemella spp.) (ring nematodes), heart worm (Dirofilaria immitis) (dog heartworm), Ditylenchus kind (Ditylenchus spp.) (stem and bulb eelworm), sour jujube rubber-insulated wire Eimeria kind (Heterodera spp.) (cyst nematode), corn Cyst nematode (Heterodera zeae) (corn cyst nematode), Hirschmanniella kind (Hirschmanniella spp.) (rootnematodes), tie Turbatrix kind (Hoplolaimus spp.) (lance nematodes), Meloidogyne kind (Meloidogynespp.) (root knot nematode), Meloidogyne incognita ((Meloidogyne incognita) (root knot nematode), Onchocerca caecutiens (Onchocercavolvulus) (hook-tail worm), Pratylenchidae belongs to kind of (PraLylenchus spp.) (rotten nematode (a lesion nematode)), perforation line Eimeria kind (Radopholus spp.) (similes thorne (burrowing nematode)) and banana reniform nematode (Rotylenchusreniformis) (kidney-shaped nematode).
Symphyla (comprehensive insects): kahikatea worm (Scutigerella immaculata).
Especially, to small cabbage moth, mythimna separata, aphid, carmine spider mite, at lower doses still there is good prevention effect.
Due to the characteristic that it is positive, above-claimed cpd can be advantageously used in protecting agriculture and the important crop of horticulture, domestic animal and breeding stock, and the environment that often goes of the mankind avoids the injury of germ, insect evil mite.
For obtaining ideal effect, the consumption of compound changes because of various factors, the formulation of the crop of such as compound used therefor, pre-protection, the type of harmful organism, gradient of infection, weather condition, application method, employing.
The compound dosage of per hectare 10 grams-5 kilograms can provide sufficient control.
The present invention also comprises using general formula I, II or Ш compound as the sterilization of active ingredient, insecticide acaricide composition.In this sterilization, insecticide acaricide composition, the weight percentage of active ingredient is between 0.5-99%.Acceptable carrier in agricultural, forestry, health is also comprised in this sterilization, insecticide acaricide composition.
Composition of the present invention can the form of preparation be used.General formula I, II or Ш compound are dissolved or dispersed in carrier as active ingredient or are mixed with preparation to be easier to dispersion as sterilization, desinsection when using.Such as: these chemicals can be made into wettable powder, oil suspending agent, aqueous suspension, aqueous emulsion, aqua or missible oil etc.In these compositions, at least add a kind of liquid or solid carrier, and suitable tensio-active agent can be added when needed.
Technical scheme of the present invention also comprises the method for control germ, insect evil mite: sterilization of the present invention, insecticide acaricide composition are imposed on described germ, insect evil mite or its growth medium.The comparatively suitable effective amount of usual selection is per hectare 10 grams to 1000 grams, and preferably having effective amount is per hectare 20 grams to 500 grams.
For some application, such as, one or more other sterilant, Insecticides (tech) & Herbicides (tech), plant-growth regulator or fertilizer etc. agriculturally can be added in sterilization of the present invention, insecticide acaricide composition, additional advantage and effect can be produced thus.
Should it is clear that, in claim limited range of the present invention, can various conversion and change be carried out.
Embodiment
Following specific embodiment is used for further illustrating the present invention, but the present invention is limited to absolutely not these examples.(except as otherwise indicate outside, raw materials used all have commercially available)
Synthetic example
Embodiment 1: the preparation of intermediate 2-(6-(4-chlorophenoxy) pyridin-3-yl) ethamine
1) preparation of 6-(4-chlorophenoxy) nicotinic acid methyl ester
To the 350ml N of 25.6g (0.2mol) para-chlorophenol, in dinethylformamide solution, add the sodium hydride 103g (3.0mol) of 70% in batches, in stirring at room temperature reaction 4h, then add 34.2g (0.2mol) 6-chlorine apellagrin methyl esters wherein in batches, finish, reaction mixture is warming up to 100 DEG C of reaction 10h, TLC monitoring after completion of the reaction, reaction solution is poured into water, extraction into ethyl acetate, organic phase is successively through washing, saturated salt is washed, dry, filter, precipitation, after resistates cooled and solidified, filter, petroleum ether, brown solid 42.0g is obtained after drying, i.e. 6-(4-chlorophenoxy) nicotinic acid methyl ester.Fusing point: 64-66 DEG C.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 3.92 (3H, s), 6.75 (1H, d), 6.96 (1H, d), 7.11 (2H, d), 7.37 (2H, d), 8.30 (1H, d), 8.81 (1H, s).
2) preparation of (6-(4-chlorophenoxy) pyridin-3-yl) methyl alcohol
At 0 DEG C, to in the 500ml anhydrous ether solution of 52.6g (0.2mol) 6-(4-chlorophenoxy) nicotinic acid methyl ester, drip the red aluminium toluene solution 74.5g (0.24mol) of 65%, finish, in stirring at room temperature reaction 4h, then at 0 DEG C, drip 10% sodium hydroxide solution prepared in advance wherein, until reaction mixture becomes clarification, then 35 DEG C of reaction 2h are warming up to, TLC monitoring after completion of the reaction, reaction solution is poured into water, toluene extracts, organic phase is successively through washing, saturated salt is washed, dry, filter, precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:3) purifying obtains product 42.2g, i.e. (6-(4-chlorophenoxy) pyridin-3-yl) methyl alcohol.White solid.Fusing point: 100-102 DEG C.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 3.20 (1H, bs), 4.56 (2H, s), 6.87 (1H, d), 7.04 (2H, d), 7.33 (2H, d), 7.69 (1H, d), 8.06 (1H, s).
3) preparation of 5-chloromethyl-2-(4-chlorophenoxy) pyridine
At 0 DEG C, to in the 350ml dichloromethane solution of 23.5g (0.1mol) (6-(4-chlorophenoxy) pyridin-3-yl) methyl alcohol, drip 17.9g (0.15mol) sulfur oxychloride, finish, in stirring at room temperature reaction 4h, TLC monitoring after completion of the reaction, decompression steams excessive sulfur oxychloride, resistates adds water, extraction into ethyl acetate, organic phase is successively through washing, and saturated sodium bicarbonate is washed, saturated salt is washed, drying, filters, precipitation, obtain product 22.8g, i.e. 5-chloromethyl-2-(4-chlorophenoxy) pyridine.White solid.Fusing point: 78-80 DEG C.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 4.55 (2H, s), 6.94 (1H, d), 7.09 (2H, d), 7.36 (2H, d), 7.75 (1H, d), 8.15 (1H, s).
4) preparation of 2-(6-(4-chlorophenoxy) pyridin-3-yl) acetonitrile
At 40 DEG C, 2.69g (55mmol) sodium cyanide is dissolved in 300ml dimethyl sulfoxide (DMSO), then 13.9g (50mmol) 5-chloromethyl-2-(4-chlorophenoxy) pyridine is added wherein, add the 18-hat-6 of catalytic amount, reaction mixture is warming up to 80 DEG C of reaction 2h, TLC monitoring after completion of the reaction, reaction solution is poured into water, toluene extracts, organic phase is successively through washing, saturated salt is washed, dry, filter, precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:3) purifying obtains product 11.2g, i.e. 2-(6-(4-chlorophenoxy) pyridin-3-yl) acetonitrile.White solid.Fusing point: 100-102 DEG C.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 3.70 (2H, s), 6.97 (1H, d), 7.08 (2H, d), 7.37 (2H, d), 7.71 (1H, d), 8.10 (1H, s).
5) 2-(preparation of 6-(4-chlorophenoxy pyridin-3-yl) ethamine
By 2.44g(0.01mol) 2-(6-(4-chlorophenoxy) pyridin-3-yl) acetonitrile, Raney nickel (1.0g), 25% ammoniacal liquor 10ml and ethanol 50ml composition mixture hydrogen atmosphere, stirred at ambient temperature reaction 3-15 hour, TLC monitoring after completion of the reaction, filtering Raney nickel, remove solvent under reduced pressure and obtain pale green viscous shape liquid 2.30g, yield 95.0%.Colorless oil.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.46 (2H, bs), 2.70 (2H, t), 2.94 (2H, t), 6.87 (1H, d), 7.07 (2H, dd), 7.34 (2H, dd), 7.55 (1H, dd), 8.02 (1H, d).
Embodiment 2: the preparation of compound 5-7
To in the 10ml acetonitrile solution of 0.25g (1.0mmol) 2-(6-(4-chlorophenoxy) pyridin-3-yl) ethamine, add triethylamine 0.15g (1.5mmol), 4-chloro-1 is added under stirring, 3-dimethyl-4-pyrazol formyl chloride 0.23g (1.2mmol), 83 DEG C of reaction 2h are warming up to after adding, TLC monitoring after completion of the reaction, by reaction solution precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:4) purifying obtains product 0.28g, i.e. compound 5-7.Pale yellow oil.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 2.22 (3H, s), 2.90 (2H, t), 3.68 (2H, m), 4.10 (3H, s), 6.89 (1H, d), 6.90 (1H, d), 7.07 (2H, d), 7.34 (2H, d), 7.62 (1H, d), 8.05 (1H, s).
Embodiment 3: the preparation of compound 7-7
To in the 10ml acetonitrile solution of 0.25g (1.0mmol) 2-(6-(4-chlorophenoxy) pyridin-3-yl) ethamine, add triethylamine 0.15g (1.5mmol), 3-ethyl-1-methyl-5-pyrazol formyl chloride 0.21g (1.2mmol) is added under stirring, 80 DEG C of reaction 2h are warming up to after adding, TLC monitoring after completion of the reaction, by reaction solution precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:4) purifying obtains product 0.28g, i.e. compound 7-7.Colorless oil.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 3.02 (2H, t), 3.94 (2H, m), 6.58 (1H, s), 6.83 (1H, s), 6.92 (1H, d), 7.07 (2H, d), 7.26 (1H, s), 7.35 (2H, d), 8.11 (1H, dd), 8.48 (1H, s).
Embodiment 4: the preparation of compound 37-13
To 0.23g (1.0mmol) 2-(6-(4-methylphenoxy) pyridin-3-yl) ethamine (preparation method's reference as above embodiment 3, difference is that starting raw material para-chlorophenol is replaced with p-methyl phenol) 10ml acetonitrile solution in, add triethylamine 0.15g (1.5mmol), the bromo-1-(3-chloropyridine of 3--2-base is added under stirring)-1-pyrazoles-5-formyl chloride 0.39g (1.2mmol), 80 DEG C of reaction 2h are warming up to after adding, TLC monitoring after completion of the reaction, by reaction solution precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:4) purifying obtains product 0.30g, i.e. compound 37-13.Colorless oil.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 2.36 (3H, s), 2.78 (2H, t), 3.54 (2H, m), 6.64 (1H, s), 6.82 (1H, d), 7.01 (2H, d), 7.20 (2H, d), 7.48 (2H, m), 7.94 (2H, d), 8.44 (1H, s).
Embodiment 5: the preparation of intermediate 2-(2-(4-chlorophenoxy) pyridin-3-yl) ethamine
1) preparation of 2-(4-chlorophenoxy) nicotinic acid methyl ester
To the 350ml N of 25.6g (0.2mol) para-chlorophenol, in dinethylformamide solution, add the sodium hydride 103g (3.0mol) of 70% in batches, in stirring at room temperature reaction 4h, then add 34.2g (0.2mol) 2-chlorine apellagrin methyl esters wherein in batches, finish, reaction mixture is warming up to 100 DEG C of reaction 10h, TLC monitoring after completion of the reaction, reaction solution is poured into water, extraction into ethyl acetate, organic phase is successively through washing, saturated salt is washed, dry, filter, precipitation, after resistates cooled and solidified, filter, petroleum ether, brown solid 42.0g is obtained after drying, i.e. 2-(4-chlorophenoxy) nicotinic acid methyl ester.White solid.Fusing point: 125.8 DEG C.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 3.95 (3H, s), 7.10 (2H, d), 7.37 (2H, d), 8.26 (2H, d).
2) preparation of (2-(4-chlorophenoxy) pyridin-3-yl) methyl alcohol
At 0 DEG C, to in the 500ml anhydrous ether solution of 52.6g (0.2mol) 2-(4-chlorophenoxy) nicotinic acid methyl ester, drip the red aluminium toluene solution 74.5g (0.24mol) of 65%, finish, in stirring at room temperature reaction 4h, then at 0 DEG C, drip 10% sodium hydroxide solution prepared in advance wherein, until reaction mixture becomes clarification, then 35 DEG C of reaction 2h are warming up to, TLC monitoring after completion of the reaction, reaction solution is poured into water, toluene extracts, organic phase is successively through washing, saturated salt is washed, dry, filter, precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:3) purifying obtains product 42.2g, i.e. (2-(4-chlorophenoxy) pyridin-3-yl) methyl alcohol.Brown solid.Fusing point: 95.1 DEG C.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) 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-chloromethyl-2-(4-chlorophenoxy) pyridine
At 0 DEG C, to in the 350ml dichloromethane solution of 23.5g (0.1mol) (6-(4-chlorophenoxy) pyridine-2-base) methyl alcohol, drip 17.9g (0.15mol) sulfur oxychloride, finish, in stirring at room temperature reaction 4h, TLC monitoring after completion of the reaction, decompression steams excessive sulfur oxychloride, resistates adds water, extraction into ethyl acetate, organic phase is successively through washing, and saturated sodium bicarbonate is washed, saturated salt is washed, drying, filters, precipitation, obtain product 22.8g, i.e. 3-chloromethyl-2-(4-chlorophenoxy) pyridine.Faint yellow solid.Fusing point: 51.1 DEG C.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) 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-chlorophenoxy) pyridin-3-yl) acetonitrile
At 40 DEG C, 2.69g (55mmol) sodium cyanide is dissolved in 300ml dimethyl sulfoxide (DMSO), then 13.9g (50mmol) 6-chloromethyl-2-(4-chlorophenoxy) pyridine is added wherein, add the 18-hat-6 of catalytic amount, reaction mixture is warming up to 80 DEG C of reaction 2h, TLC monitoring after completion of the reaction, reaction solution is poured into water, toluene extracts, organic phase is successively through washing, saturated salt is washed, dry, filter, precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:3) purifying obtains product 11.2g, i.e. 2-(2-(4-chlorophenoxy) pyridin-3-yl) acetonitrile.White solid.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) 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-chlorophenoxy) pyridin-3-yl) ethamine
By 2.44g(0.01mol) 2-(2-(4-chlorophenoxy) pyridin-3-yl) acetonitrile, Raney nickel (1.0g), 25% ammoniacal liquor 10ml and ethanol 50ml composition mixture hydrogen atmosphere, stirred at ambient temperature reaction 3-15 hour, TLC monitoring after completion of the reaction, filtering Raney nickel, remove solvent under reduced pressure and obtain pale green viscous shape liquid 2.30g, yield 95.0%.Light green oil.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.46 (2H, bs), 2.94 (2H, t), 3.08 (2H, t), 6.53 (1H, d), 7.35 (1H, d), 7.40 (1H, dd), 7.48 (2H, dd), 7.61 (2H, dd).
Embodiment 6: the preparation of compound 103-1
To in the 10ml acetonitrile of 0.25g (1.0mmol) 2-(2-(4-chlorophenoxy) pyridin-3-yl) ethamine, add triethylamine 0.15g (1.5mmol), 4-chloro-1 is added under stirring, 3-dimethyl-5-pyrazol formyl chloride 0.23g (1.2mmol), 80 DEG C of reaction 2h are warming up to after adding, TLC monitoring after completion of the reaction, by reaction solution precipitation, resistates column chromatography (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C), and volume ratio is 1:4) purifying obtains product 0.28g.I.e. compound 103-1.White solid.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 2.21 (3H, s), 3.06 (2H, t), 3.81 (2H, m), 4.07 (1H, s), 6.77 (1H, s), 6.97 (1H, d), 7.03 (1H, d), 7.35 (2H, d), 7.59 (1H, d), 8.05 (1H, s).
Embodiment 7: the preparation of intermediate 2-(4-(4-chlorophenoxy) pyridin-4-yl) ethamine
1) preparation of 2-(4-chlorophenoxy) iso methyl nicotinate
To the 350ml N of 25.6g (0.2mol) para-chlorophenol, in dinethylformamide solution, add the sodium hydride 103g (3.0mol) of 70% in batches, in stirring at room temperature reaction 4h, then add 34.2g (0.2mol) 2-chloroisonicotinic acid methyl esters wherein in batches, finish, reaction mixture is warming up to 100 DEG C of reaction 10h, TLC monitoring after completion of the reaction, reaction solution is poured into water, extraction into ethyl acetate, organic phase is successively through washing, saturated salt is washed, dry, filter, precipitation, after resistates cooled and solidified, filter, petroleum ether, brown solid 42.0g is obtained after drying, i.e. 2-(4-chlorophenoxy) iso methyl nicotinate.Fusing point: 64-66 DEG C.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) 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-chlorophenoxy) pyridin-4-yl) methyl alcohol
At 0 DEG C, to in the 500ml anhydrous ether solution of 52.6g (0.2mol) 2-(4-chlorophenoxy) iso methyl nicotinate, drip the red aluminium toluene solution 74.5g (0.24mol) of 65%, finish, in stirring at room temperature reaction 4h, then at 0 DEG C, drip 10% sodium hydroxide solution prepared in advance wherein, until reaction mixture becomes clarification, then 35 DEG C of reaction 2h are warming up to, TLC monitoring after completion of the reaction, reaction solution is poured into water, toluene extracts, organic phase is successively through washing, saturated salt is washed, dry, filter, precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:3) purifying obtains product 42.2g, i.e. (2-(4-chlorophenoxy) pyridin-4-yl) methyl alcohol.Yellow liquid.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 3.95 (1H, bs), 4.70 (2H, s), 6.87 (1H, d), 6.98 (1H, d), 7.14 (2H, d), 7.34 (2H, d), 8.11 (1H, d).
3) preparation of 4-chloromethyl-2-(4-chlorophenoxy) pyridine
At 0 DEG C, to in the 350ml dichloromethane solution of 23.5g (0.1mol) (2-(4-chlorophenoxy) pyridin-4-yl) methyl alcohol, drip 17.9g (0.15mol) sulfur oxychloride, finish, in stirring at room temperature reaction 4h, TLC monitoring after completion of the reaction, decompression steams excessive sulfur oxychloride, resistates adds water, extraction into ethyl acetate, organic phase is successively through washing, and saturated sodium bicarbonate is washed, saturated salt is washed, drying, filters, precipitation, obtain product 22.8g, i.e. 4-chloromethyl-2-(4-chlorophenoxy) pyridine.White solid.Fusing point: 78-80 DEG C.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) 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-chlorophenoxy) pyridin-4-yl) acetonitrile
At 40 DEG C, 2.69g (55mmol) sodium cyanide is dissolved in 300ml dimethyl sulfoxide (DMSO), then 13.9g (50mmol) 4-chloromethyl-2-(4-chlorophenoxy) pyridine is added wherein, add the 18-hat-6 of catalytic amount, reaction mixture is warming up to 80 DEG C of reaction 2h, TLC monitoring after completion of the reaction, reaction solution is poured into water, toluene extracts, organic phase is successively through washing, saturated salt is washed, dry, filter, precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:3) purifying obtains product 11.2g, i.e. 2-(2-(4-chlorophenoxy) pyridin-4-yl) acetonitrile.White solid.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) 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-(preparation of 2-(4-chlorophenoxy pyridin-4-yl) ethamine
By 2.44g(0.01mol) 2-(2-(4-chlorophenoxy) pyridin-4-yl) acetonitrile, Raney nickel (1.0g), 25% ammoniacal liquor 10ml and ethanol 50ml composition mixture hydrogen atmosphere, stirred at ambient temperature reaction 3-15 hour, TLC monitoring after completion of the reaction, filtering Raney nickel, remove solvent under reduced pressure and obtain reddish-brown viscous liquid 2.30g, yield 95.0%.Brown oil.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.46 (2H, bs), 2.70 (2H, t), 2.94 (2H, t), 6.87 (1H, d), 7.07 (2H, dd), 7.34 (2H, dd), 7.55 (1H, dd), 8.02 (1H, d).
Embodiment 8: the preparation of compound 95-7
To in the 10ml acetonitrile of 0.25g (1.0mmol) 2-(2-(4-chlorophenoxy) pyridin-4-yl) ethamine, add triethylamine 0.15g (1.5mmol), 4-chloro-1 is added under stirring, 3-dimethyl-5-pyrazol formyl chloride 0.23g (1.2mmol), 80 DEG C of reaction 2h are warming up to after adding, TLC monitoring after completion of the reaction, by reaction solution precipitation, resistates column chromatography (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C), and volume ratio is 1:4) purifying obtains product 0.28g.I.e. compound 95-7.White solid.
1h-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ (ppm): 2.07 (3H, s), 3.00 (2H, s), 3.74 (2H, s), 4.09 (3H, s), 6.81 (2H, d), 7.09 (3H, d), 7.03 (1H, d), 7.36 (2H, d), 8.21 (1H, s).
Embodiment 9: the preparation of intermediate 6-(4-4-trifluoromethylphenopendant)-3-aminopyridine
1) preparation of 6-(4-4-trifluoromethylphenopendant)-3-nitropyridine
10g (0.062mol) p-trifluoromethyl-phenol is joined in the there-necked flask of 250mL, adds 50mL DMF and make it dissolve, stirred at ambient temperature 10min, then add 2.3g (0.095mol) NaH, continue at room temperature to stir 3h.To be mixed complete after, add 10g (0.062mol) 2-chloro-5-nitropyridine, slowly be warming up to 80 DEG C, after TLC question response completes (about 3h), be cooled to room temperature, add 1000mL water, a large amount of solid is had to separate out, suction filtration, dry, obtain pale solid product 16.8g, yield: 94%.
1H NMR(300MHz,CDCl
3)δ8.90(d,J=2.8Hz,1H),8.41(dd,J=9.0,2.8Hz,1H),7.60(d,J=8.5Hz,2H),7.20(d,J=8.4Hz,2H),7.02(d,J=9.0Hz,1H).
2) preparation of 6-(4-4-trifluoromethylphenopendant)-3-aminopyridine
2.0g (7.0mmol) 6-(4-4-trifluoromethylphenopendant)-3-nitropyridine is joined in the there-necked flask of 150mL, add 20mL AcOH, then add 1.37g (0.021mol) zinc powder in batches, 3h is reacted under room temperature, after TLC question response completes, outstanding steaming except desolventizing, drip NaOH(5%) to be adjusted to PH aobvious neutral for the aqueous solution, with the extraction into ethyl acetate of 3 × 20mL, the anhydrous MgSO of organic phase
4drying, obtains light red oil product 1.3g through column chromatography, yield 81% after outstanding steaming.
Embodiment 10: the preparation of compound 40-13
1.3g6-(4-4-trifluoromethylphenopendant)-3-amido pyridine (5.16mmol) is dissolved in 10mL CH
2cl
2in, add 1mL triethylamine, under normal temperature, stir 10min, then drip the CH of the bromo-1-of 1.66g (5.16mmol) 3-(3-chloropyridine-2-base)-1H-pyrazoles-5-formyl chloride
2cl
2solution, reacts 2h under room temperature.After TLC question response completes, outstanding steaming removes desolventizing, adds 30mL water, with the extraction into ethyl acetate of 3 × 10mL, and the anhydrous MgSO of organic phase
4drying, obtains pale red solid 2.17g through column chromatography, m.p.193-195 DEG C, yield 78% after outstanding steaming.
1H NMR(400MHz,CDCl
3)δ8.49(dd,J=4.7,1.5Hz,1H),8.42(s,1H),8.14(d,J=11.6Hz,2H),7.94(dd,J=8.1,1.5Hz,1H),7.64(d,J=8.5Hz,2H),7.45(dd,J=8.1,4.7Hz,1H),7.20(d,J=8.5Hz,2H),6.99–6.94(m,2H).
Other compounds of the present invention can be prepared with reference to above embodiment.
The physical data of part of compounds and nuclear magnetic data (
1hNMR, 300MHz, interior mark TMS, ppm) as follows:
5-1: colorless oil.δ(CDCl
3):2.20(s,3H),2.92(t,2H),3.69(dd,2H),4.15(s,3H),6.65(s,1H),6.95(d,1H),7.09–7.05(m,2H),7.33–7.26(m,3H),7.67(dd,1H),8.02(d,1H).
5-6: colorless oil.δ(CDCl
3):2.23(s,3H),2.92(t,2H),3.70(dd,2H),4.11(s,3H),6.74(s,1H),6.92(d,1H),7.02(dd,1H),7.21–7.12(m,2H),7.32(t,1H),7.63(dd,1H),8.08(d,1H).
5-7: colorless oil.δ(CDCl
3):3.02(2H,t),3.94(2H,m),6.58(1H,s),6.83(1H,s),6.92(1H,d),7.07(2H,d),7.26(1H,s),7.35(2H,d),8.11(1H,dd),8.48(1H,s)。
5-16：δ(CDCl
3):2.23(s,3H).2.36(s,3H),2.89(t,2H),3.69(dd,2H),4.11(s,3H),6.74(s,1H),6.86(d,1H),7.02(d,2H),7.20(d,2H),7.58(dd,1H),8.06(d,1H).
5-19: colorless oil.δ(CDCl
3):2.21(s,3H),2.88(t,2H),3.67(dd,2H),3.81(s,3H),4.10(s,3H),6.72(s,1H),6.83(d,1H),6.95–6.89(m,2H),7.09–7.01(m,2H),7.56(dd,1H),8.04(d,1H).
5-21: colorless oil.δ(CDCl
3):2.22(s,3H),2.92(t,2H),3.70(dd,2H),4.11(s,3H),6.74(s,1H),6.95(d,1H),7.32(d,1H),7.39(s,1H),7.48(dt,2H),7.65(dd,1H),8.07(d,1H).
5-22: white solid.δ(CDCl
3):2.23(s,3H),2.94(t,2H),3.71(dd,2H),4.11(d,3H),6.76(s,1H),6.98(d,1H),7.35–7.14(m,2H),7.66(d,3H),8.10(s,1H).
5-83: white solid.δ(CDCl
3):2.22(s,3H),2.91(t,2H),3.73–3.66(dd,2H),4.11(s,3H),6.73(s,1H),6.98(d,1H),7.23–7.15(m,2H),7.40(d,1H),7.65(d,1H),8.02(s,1H).
5-110: colorless oil.δ(CDCl
3):2.14(s,3H),2.21(s,3H),2.88(t,2H),3.68(dd,2H),4.11(d,3H),6.72(s,1H),6.87(d,1H),6.97(d,1H),7.18(dd,1H),7.25(dd,1H),7.59(dd,1H),8.01(d,1H).
7-7: colorless oil.δ(CDCl
3):3.02(2H,t),3.94(2H,m),6.58(1H,s),6.83(1H,s),6.92(1H,d),7.07(2H,d),7.26(1H,s),7.35(2H,d),8.11(1H,dd),8.48(1H,s)。
7-21: colorless oil.δ(CDCl
3):1.22(t,3H),2.61(q,2H),2.87(t,2H),3.61(q,2H),4.09(s,3H),6.05(s,1H),6.20(s,1H),6.90(d,1H),7.07(d,2H),7.35(d,2H),7.59(dd,1H),8.02(s,1H).
20-7: colorless oil.δ(CDCl
3):2.87(t,2H),3.65(dd,2H),3.95(s,3H),6.07(s,1H),6.89(d,1H),7.06(d,2H),7.35(d,2H),7.59(dd,1H),7.94(s,1H),8.03(s,1H).
22-7: white solid.δ(CDCl
3):2.26(s,3H),2.43(s,3H),2.87(t,2H),3.63(d,2H),3.70(s,3H),5.60(s,1H),6.88(d,1H),7.10–6.99(m,2H),7.39–7.29(m,2H),7.60(d,1H),8.02(d,1H).
35-13: white solid.δ(CDCl
3):6.87(d,1H),6.93(s,1H),7.09(d,2H),7.20(t,1H),7.38(d,2H),7.44(dd,1H),7.93(dd,1H),8.06(d,1H),8.10(s,1H),8.26(s,1H),8.48(dd,1H).
36-13: khaki color solid.δ(CDCl
3):6.86(d,1H),6.95(s,1H),7.06–7.00(m,2H),7.36–7.30(m,2H),7.43(dd,1H),7.93(dd,1H),8.07(dd,1H),8.12(d,1H),8.46(dd,1H),8.65(s,1H).
37-13: white solid.δ(CDCl
3):6.97(dd,3H),2.30(s,3H),7.19(d,2H),7.42(s,1H),7.65(dd,1H),8.02(dd,1H),8.23(d,1H),8.29(d,1H),8.52(d,1H),10.71(s,1H).
40-13: pale red solid.δ(CDCl
3):6.99–6.94(m,2H),7.20(d,2H),7.45(dd,1H),7.64(d,2H),7.94(dd,1H),8.14(d,2H),8.42(s,1H),8.49(dd,1H).
41-13: khaki color solid.δ(CDCl
3):3.80(s,3H),6.82(d,1H),6.91(d,3H),7.03(d,2H),7.43(dd,1H),7.93(dd,1H),8.02(d,1H),8.06(s,1H),8.30(s,1H),8.47(dd,1H).
46-13: white solid.δ(CDCl
3):6.93–6.88(m,2H),7.28(d,1H),7.36(s,1H),7.44(dd,2H),7.48(d,1H),7.94(dd,1H),8.04(dd,1H),8.08(d,1H),8.47(dd,1H),8.58(s,1H).
48-13: faint yellow solid.δ(CDCl
3):6.98–6.94(m,2H),7.12(d,1H),7.29(d,1H),7.44(dd,1H),7.47(d,1H),7.93(dd,1H),8.06(d,1H),8.11(d,1H),8.35(s,1H),8.48(dd,1H).
62-13: yellow oil.δ(CDCl
3):2.36(s,3H),2.78(t,2H),3.53(q,2H),6.32(s,1H),6.64(s,1H),6.82(d,1H),7.01(d,2H),7.21(d,2H),7.47(dd,2H),7.91(dd,2H),8.45(d,1H).
70-13: yellow oil.δ(CDCl
3):2.80(t,2H),3.54(dd,2H),6.37(s,1H),6.66(s,1H),6.88(d,1H),7.03(d,1H),7.16(dd,2H),7.32(t,1H),7.41(dd,1H),7.53(dd,1H),7.93–7.87(m,1H),7.98(d,1H),8.45(d,1H).
73-13: white solid.δ(CDCl
3):2.80(t,2H),3.55(dd,2H),6.28(s,1H),6.65(s,1H),6.95(d,1H),7.23–7.16(m,1H),7.42(d,1H),7.56(d,2H),7.74–7.70(m,1H),7.96–7.88(m,2H),8.44(d,1H).
95-7: yellow solid.δ(CDCl
3):2.07(3H,s),3.00(2H,s),3.74(2H,s),4.09(3H,s),6.81(2H,d),7.09(3H,d),7.03(1H,d),7.36(2H,d),8.21(1H,s).
96-7: white solid.δ(CDCl
3):2.07(3H,s),3.00(2H,s),3.74(2H,s),4.09(3H,s),6.81(2H,d),7.09(3H,d),7.03(1H,d),7.36(2H,d),8.21(1H,s).
103-1: white solid.δ2.21(s,3H),3.07(t,2H),3.82(q,2H),4.11(s,3H),6.79(bs,1H),6.95(t,1H),7.09(d,2H),7.17(d,1H),7.38(t,2H),7.59(dd,1H),8.05(dd,1H).
103-7: white solid.δ2.21(s,3H),3.06(t,2H),3.81(q,2H),4.07(s,3H),6.77(bs,1H),6.96(q,1H),7.06(t,2H),7.34(dd,2H),7.60(d,1H),8.04(dd,1H).
Biological activity determination
The compounds of this invention all shows good activity to the multiple germ in agriculture field, also demonstrates good pesticide and miticide actility.And with contrast medicament and carried out contrast test.Control compound comprises the CK1 to CK13 of background technology part, Tolfenpyrad, and with reference to prior art file synthesis following KC14 to KC23, structure is in table 117:
Table 117 control compound table
Embodiment 11: fungicidal activity measures
Antifungal Activity in Vitro or the test of live body protected effect has been carried out with the multiple fungal disease of the compounds of this invention sample to plant.Fungicidal activity measurement result is shown in following example.
(1) Antifungal Activity in Vitro measures
Measuring method is as follows: adopt high-throughput screening method, by test compound sample with the solvent be applicable to (kind of solvent as acetone, methyl alcohol, DMF etc., and according to its to the dissolving power of sample Selective dissolution, be mixed with desired concn liquid to be measured.Under ultra-clean Working environment, joined by liquid to be measured in the micropore of 96 well culture plates, then add wherein by pathogenic bacteria propagulum suspension, the culture plate after process is placed in constant incubator to be cultivated.Investigate after 24 hours, estimate pathogenic bacteria propagulum during investigation and sprout or growing state, and according to the sprouting of control treatment or growing state, assessing compound bacteriostatic activity.
Antifungal Activity in Vitro (representing with the inhibiting rate) test result of part of compounds is as follows:
Inhibiting rate to rice blast fungus:
When liquor strength is 25mg/L, the inhibiting rate of compound 5-1,5-6,5-7,5-16,5-19,5-21,5-22,5-110,73-13,103-7 etc. is 80%.
Carried out part of compounds and the active simultaneous test contrasting medicament, test result represents in "/" in Table 118(table does not test).
The Antifungal Activity in Vitro of table 118 pair rice blast
| Compound | 25ppm | Compound | 25ppm | Compound | 25ppm | Compound | 25ppm |
| 5-110 | 80 | 5-19 | 80 | CK1 | 0 | CK17 | 0 |
| 5-16 | 80 | 5-21 | 80 | CK10 | 0 | CK21 | 0 |
| 5-22 | 80 | 5-1 | 80 | CK11 | 0 | CK23 | 0 |
| 5-7 | 80 | 73-13 | 80 | CK14 | 0 | ||
| 5-6 | 80 | 103-7 | 80 | CK16 | 0 |
Inhibiting rate to botrytis cinerea pers:
When liquor strength is 25mg/L, the inhibiting rate of compound 5-19,5-21,5-22 etc. is 50%.
Carried out part of compounds and the active simultaneous test contrasting medicament, test result represents in "/" in Table 119(table does not test).
The Antifungal Activity in Vitro of table 119 pair gray mold of cucumber
| Compound | 25ppm | Compound | 25ppm | Compound | 25ppm | Compound | 25ppm |
| 5-22 | 50 | CK4 | 0 | CK14 | 0 | CK19 | 0 |
| 5-19 | 50 | CK7 | 0 | CK15 | 0 | CK20 | 0 |
| 5-21 | 50 | CK9 | 0 | CK16 | 0 | CK21 | 0 |
| CK1 | 0 | CK10 | 0 | CK17 | 0 | CK23 | 0 |
| CK3 | 0 | CK11 | 0 | CK18 | 0 |
(2) live body prolection measures
Measuring method is as follows: adopt the potted plant measuring method of live body, by test compound sample, with a small amount of solvent, (kind of solvent is as acetone, methyl alcohol, DMF etc., and according to it, dissolving power of sample is selected, the volume ratio of quantity of solvent and spouting liquid is equal to or less than 0.05) dissolve, dilute with the water containing 0.1% tween 80, be mixed with desired concn liquid to be measured.On crops sprayer, liquid to be measured is sprayed on disease host plant (host plant is the standard Potted orchard at warm indoor cultivation), after 24 hours, carry out disease inoculation.According to disease feature, cultivate being placed in phytotron after the disease plant inoculating needing temperature control moisturizing to cultivate, after disease completes and infects, immigration hot-house culture, the disease plant cultivated not needing moisturizing is directly cultivated at warm indoor inoculation.After contrasting fully morbidity, (being generally week age) carries out the assessment of compound protection effect.
The live body prolection 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 5-1,5-7,5-22,5-83,22-7,35-13,36-13,40-13,41-13,46-13,48-13,62-13,70-13,73-13 etc. is 100%;
When liquor strength is 100mg/L, the preventive effect of compound 5-1,5-7 etc. all reaches 100%, and the preventive effect of compound 5-22,5-83,70-13,73-13 etc. is 90-99%; The preventive effect of compound 62-13 etc. is 80-89%;
When liquor strength is 50mg/L, the preventive effect of compound 5-1,5-7 etc. all reaches 100%, and the preventive effect of compound 5-22,5-83 etc. is 90-99%, and the preventive effect of compound 73-13 etc. is 80-89%;
When liquor strength is 25mg/L, the preventive effect of compound 5-1 etc. all reaches 100%, and the preventive effect of compound 5-7,5-22 etc. is 90-99%;
When liquor strength is 12.5mg/L, the preventive effect of compound 5-1 etc. is 80-89%.
Carried out part of compounds and the active simultaneous test contrasting medicament, test result represents in "/" in Table 120(table does not test).
The live body prolection of table 120 pair cucumber downy mildew
| Compound | 400mg/L | 100mg/L | 50mg/L | 25mg/L | 12.5mg/L |
| 5-22 | 100 | 98 | 98 | 98 | 70 |
| 5-7 | 100 | 100 | 100 | 98 | 10 |
| 5-83 | 100 | 95 | 90 | 70 | / |
| 5-1 | 100 | 100 | 100 | 100 | 85 |
| 62-13 | 100 | 80 | 60 | 40 | / |
| 70-13 | 100 | 98 | 70 | 50 | / |
| 73-13 | 100 | 95 | 80 | 40 | / |
| CK1 | 0 | / | / | / | / |
| CK6 | 0 | / | / | / | / |
| CK7 | 0 | / | / | / | / |
| CK8 | 85 | / | / | / | / |
| CK9 | 100 | 30 | 20 | 0 | / |
| CK13 | 0 | / | / | / | / |
| CK17 | 0 | / | / | / | / |
| CK18 | 0 | / | / | / | / |
| CK19 | 0 | / | / | / | / |
| CK23 | 0 | / | / | / | / |
Live body preventive effect to corn rust:
When liquor strength is 400mg/L, the preventive effect of compound 5-1,5-6,5-22,5-110,7-7,36-13,48-13,70-13 etc. is 100%, the preventive effect of compound 5-7,103-1,103-7 etc. is 90-99%, and the preventive effect of compound 5-16,5-19,5-21,5-83,7-21,46-13,96-7 etc. is 80-89%;
When liquor strength is 100mg/L, the preventive effect of compound 5-1,36-13,48-13 etc. is 80-89%.
Carried out part of compounds and the active simultaneous test contrasting medicament, test result represents in "/" in Table 121(table does not test).
The live body prolection of table 121 pair corn rust
| Compound | 400mg/L | 100mg/L | 25mg/L | Compound | 400mg/L | 100mg/L | 25mg/L |
| 5-7 | 98 | 30 | 0 | CK10 | 60 | / | / |
| 5-6 | 100 | 40 | 0 | CK11 | 100 | 0 | / |
| 5-1 | 100 | 80 | 60 | CK13 | 100 | 0 | / |
| 36-13 | 100 | 85 | 60 | CK14 | 100 | 0 | / |
| 48-13 | 100 | 80 | 70 | CK15 | 0 | / | / |
| 70-13 | 100 | 50 | 0 | CK16 | 100 | 0 | / |
| 103-7 | 98 | 70 | 60 | CK17 | 0 | / | / |
| CK1 | 0 | / | / | CK18 | 0 | / | / |
| CK6 | 0 | / | / | CK19 | 0 | / | / |
| CK7 | 0 | / | / | CK20 | 95 | 0 | / |
| CK8 | 0 | / | / | CK21 | 100 | 0 | / |
| CK9 | 100 | 0 | / | CK23 | 0 | / | / |
Live body preventive effect to wheat powdery mildew:
When liquor strength is 400mg/L, the preventive effect of compound 5-16,5-110,36-13 etc. is 100%, and the preventive effect of compound 5-1,5-6,5-7,5-22,5-83 etc. is 80%;
When liquor strength is 100mg/L, the preventive effect of compound 5-83 etc. is 100%;
When liquor strength is 25mg/L, the preventive effect of compound 5-83 etc. is 100%;
When liquor strength is 6.25mg/L, the preventive effect of compound 5-83 etc. is 100%.
Carried out part of compounds and the active simultaneous test contrasting medicament, test result represents in "/" in Table 122(table does not test).
The live body prolection of table 122 pair wheat powdery mildew
| Compound | 400mg/L | 100mg/L | 25mg/L | Compound | 400mg/L | 100mg/L | 25mg/L |
| 5-110 | 100 | 0 | / | CK9 | 0 | / | / |
| 5-16 | 100 | 0 | / | CK10 | 0 | / | / |
| 5-22 | 80 | / | / | CK11 | 0 | / | / |
| 5-7 | 80 | / | / | CK13 | 0 | / | / |
| 5-6 | 80 | / | / | CK14 | 0 | / | / |
| 5-83 | 80 | / | / | CK15 | 40 | / | / |
| 5-1 | 80 | / | / | CK16 | 0 | / | / |
| 36-13 | 100 | 100 | 100 | CK17 | 0 | / | / |
| CK1 | 0 | / | / | CK18 | 0 | / | / |
| CK3 | 0 | / | / | CK19 | 0 | / | / |
| CK4 | 0 | / | / | CK20 | 0 | / | / |
| CK6 | 0 | / | / | CK21 | 0 | / | / |
| CK7 | 0 | / | / | CK22 | 0 | / | / |
| CK8 | 0 | / | / | CK23 | 0 | / | / |
Embodiment 12: pesticide and miticide actility measures
With the compounds of this invention, insecticidal activity assay test is carried out to several insect.Measuring method is as follows:
After testing compound dissolves with the mixed solvent of acetone/methanol (1:1), with containing 0.1%(wt) water of tween 80 is diluted to required concentration.
With small cabbage moth, black peach aphid, carmine spider mite for target, airbrush spray method is adopted to carry out insecticidal activity assay.
(1) determination of activity of small cabbage moth, is killed
Measuring method: leaf dish cabbage leaves punch tool being broken into diameter 2cm, the pressure of airbrush spraying process is that 10psi (is roughly equal to 0.7kg/cm
2), every leaf dish pros and cons spraying, spouting liquid is 0.5ml.Often process access after drying in the shade and try worm 10 2 ages, often process 3 times and repeat.Put into 25 DEG C, relative humidity 60 ~ 70% observation indoor cultivation after process, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.
As follows to the partial test result of small cabbage moth:
When liquor strength is 600mg/L, compound 5-16 etc. are 100% to small cabbage moth lethality rate.
Carried out part of compounds and the active simultaneous test contrasting medicament, test result represents in "/" in Table 123(table does not test).
The preventive effect of table 123 pair small cabbage moth
(2) determination of activity of black peach aphid, is killed
Measuring method: cut-off footpath 6cm culture dish, covers one deck filter paper at the bottom of ware, and drips appropriate tap water moisturizing.Clip suitable size (diameter is about 3cm) from the cabbage plant cultivating black peach aphid and the long cabbage leaves having 15 ~ 30 aphids, remove the aphid of alatae and face of blade, blade back is upwards placed in culture dish.The pressure of airbrush spraying process is 10psi (being roughly equal to 0.7kg/cm2), and spouting liquid is 0.5ml, often processes 3 times and repeats.Put into 25 DEG C, relative humidity 60 ~ 70% observation indoor cultivation after process, 48 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.
As follows to the partial test result of black peach aphid:
When liquor strength is 600mg/L, compound 5-6,5-7,5-16,5-19,5-22,5-110,7-7,7-21 etc. are 100% to the lethality rate of black peach aphid, compound 5-83,37-13 etc. are 80-89% to the lethality rate of black peach aphid, compound 36-13,48-13 etc. are 70-79% to the lethality rate of black peach aphid, compound 22-7, the lethality rate to black peach aphid such as 35-13,70-13,103-7 is 60-69%.
Carried out part of compounds and the active simultaneous test contrasting medicament, test result represents in "/" in Table 124(table does not test).
The preventive effect of table 124 pair black peach aphid
| Compound | 600mg/L | 100mg/L | Compound | 600mg/L | 100mg/L | Compound | 600mg/L | 100mg/L |
| 5-110 | 100 | 64 | 36-13 | 71 | / | CK9 | 0 | / |
| 5-16 | 100 | 11 | 37-13 | 83 | 73 | CK11 | 0 | / |
| 5-22 | 100 | 38 | 48-13 | 71 | / | CK12 | 0 | / |
| 5-7 | 100 | 0 | 70-13 | 67 | / | CK13 | 0 | / |
| 5-6 | 100 | 0 | 103-1 | 59 | / | CK14 | 28 | / |
| 5-83 | 81 | 45 | 103-7 | 67 | / | CK16 | 0 | / |
| 5-19 | 100 | 12 | CK1 | 0 | / | CK17 | 0 | / |
| 7-7 | 100 | 69 | CK5 | 0 | / | CK18 | 0 | / |
| 7-21 | 100 | 56 | CK6 | 0 | / | CK19 | 0 | / |
| 22-7 | 67 | / | CK7 | 0 | / | CK21 | 24 | / |
| 35-13 | 68 | / | CK8 | 0 | / | CK23 | 0 | / |
(3) determination of activity of carmine spider mite, is killed
Measuring method: get two panels true leaf Kidney bean seedling, connects carmine spider mite and becomes mite and after investigating radix, carry out whole strain process with airbrush atomizer, pressure is that 10psi (is roughly equal to 0.7kg/cm
2), spouting liquid is 0.5ml.Often process and repeat for 3 times, process is placed on standard sight room, and 72 hours " Invest, Then Investigate " survival mite numbers, calculate mortality ratio.
As follows to the partial test result of carmine spider mite:
When liquor strength is 600mg/L, compound 7-21,103-1 etc. are 100% to carmine spider mite lethality rate, and compound 5-16 etc. are 60-69% to carmine spider mite lethality rate.
Carried out part of compounds and the active simultaneous test contrasting medicament, test result represents in "/" in Table 125(table does not test).The preventive effect of table 125 pair carmine spider mite
| Compound | 600mg/L | 100mg/L | 10mg/L | Compound | 600mg/L | 100mg/L | 10mg/L |
| 5-110 | 55 | / | / | CK9 | 0 | / | / |
| 5-16 | 67 | / | / | CK11 | 7 | / | / |
| 7-21 | 100 | 51 | 28 | CK13 | 0 | / | / |
| 46-13 | 50 | / | / | CK15 | 0 | / | / |
| 103-1 | 100 | 67 | 63 | CK16 | 7 | / | / |
| CK1 | 0 | / | / | CK17 | 0 | / | / |
| CK6 | 0 | / | / | CK19 | 0 | / | / |
| CK7 | 0 | / | / | CK22 | 12 | / | / |
| CK8 | 0 | / | / | CK23 | 0 | / | / |
Claims (10)
1. a pyrazol acid amide compounds, shown in the following general formula of compound structure:
Wherein: Q is selected from
or
When Q (C=O) NAB-is connected to 5 of pyridine ring, compound is as shown in general formula I; When Q (C=O) NAB-is connected to 4 of pyridine ring, compound is as shown in general formula I I; When Q (C=O) NAB-is connected to 3 of pyridine ring, compound is as shown in general formula Ш:
In formula:
A is selected from hydrogen, hydroxyl, formyl radical, C
1-C
12alkyl, halo C
1-C
12alkyl, C
1-C
12alkoxyl group, halo C
1-C
12alkoxyl group, C
3-C
12cycloalkyl, C
1-C
12alkylthio, C
2-C
12enylsulfanyl, C
2-C
12thiazolinyl, C
2-C
12alkynyl, halo C
2-C
12thiazolinyl, halo C
2-C
12alkynyl, C
1-C
12alkoxy C
1-C
12alkyl, halo C
1-C
12alkoxy C
1-C
12alkyl, C
1-C
12alkylthio C
1-C
12alkyl, halo C
1-C
12alkylthio C
1-C
12alkyl, C
1-C
12alkyl sulphinyl, halo C
1-C
12alkyl sulphinyl, C
1-C
12alkyl sulphonyl, halo C
1-C
12alkyl sulphonyl, C
1-C
12alkyl amino sulfonyl, two (C
1-C
12alkyl) amino-sulfonyl, C
1-C
12alkylsulfonyl aminocarbonyl, C
1-C
12alkyl-carbonyl-amino alkylsulfonyl, C
3-C
12cycloalkyloxycarbonyl, C
1-C
12alkyl-carbonyl, halo C
1-C
12alkyl-carbonyl, C
1-C
12alkoxy carbonyl, halo C
1-C
12alkoxy carbonyl, C
1-C
12alkyl-carbonyl C
1-C
12alkyl, C
1-C
12alkoxy carbonyl C
1-C
12alkyl, C
1-C
12alkyl amino-carbonyl, two (C
1-C
12alkyl) aminocarboxyl, C
2-C
12allyloxycarbonyl, C
2-C
12alkynyloxycar bonyl, C
1-C
12alkoxy C
1-C
12alkoxy carbonyl, C
1-C
12alkylamino sulfenyl, two (C
1-C
12alkyl) amino sulfenyl, (mixing) aryl carbonyl C that is unsubstituted or that replaced further by the following group of 1-5
1-C
6alkyl, (mixing) aryl carbonyl, (mixing) aryloxycarbonyl, (mixing) aryl C
1-C
6alkyloxycarbonyl or (mixing) aryl C
1-C
6alkyl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen and pyridine ring 3,4 or 5 carbon are directly connected
2cR
ar
b-or-CH
2cR
ar
bcR
ar
b-;
R
a, R
bmay be the same or different, be selected from hydrogen, C respectively
1-C
12alkyl, C
3-C
12cycloalkyl, C
2-C
12thiazolinyl, C
2-C
12alkynyl, halo C
2-C
12thiazolinyl, halo C
2-C
12alkynyl, C
1-C
12alkoxy C
1-C
12alkyl, aryl C that is unsubstituted or that replaced further by 1-5 following group
1-C
6alkyl or heteroaryl C
1-C
6alkyl: halogen, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group, or Ra, R
bc is formed with the carbon be connected
3-C
8ring;
X is selected from O or S;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C respectively
1-C
12alkyl, halo C
1-C
12alkyl, C
1-C
12alkoxyl group, halo C
1-C
12alkoxyl group, C
3-C
12cycloalkyl, C
2-C
12thiazolinyl, C
2-C
12alkynyl, C
2-C
12alkene oxygen base, halo C
2-C
12alkene oxygen base, C
2-C
12alkynyloxy group, halo C
2-C
12alkynyloxy group, C
1-C
12alkylthio, halo C
1-C
12alkylthio, C
1-C
12alkoxy C
1-C
12alkyl, halo C
1-C
12alkoxy C
1-C
12alkyl, C
1-C
12alkylthio C
1-C
12alkyl, halo C
1-C
12alkylthio C
1-C
12alkyl, C
1-C
12alkyl sulphinyl, halo C
1-C
12alkyl sulphinyl, C
1-C
12alkyl sulphonyl, halo C
1-C
12alkyl sulphonyl, C
1-C
12alkyl amino sulfonyl, C
1-C
12alkylamino, halo C
1-C
12alkylamino, two (C
1-C
12alkyl) amino, C
1-C
12alkoxy carbonyl, CONH
2, C
1-C
12alkyl amino-carbonyl, two (C
1-C
12alkyl) aminocarboxyl, cyano group C
1-C
12alkoxyl group, C
1-C
12alkoxy carbonyl C
1-C
12alkyl, C
1-C
12alkyl amino-carbonyl C
1-C
12alkyl or two (C
1-C
12alkyl) aminocarboxyl C
1-C
12alkyl;
R
6, R
6', R
7may be the same or different, be selected from hydrogen, halogen, nitro, cyano group, C respectively
1-C
12alkyl, halo C
1-C
12alkyl, C
3-C
12cycloalkyl, C
1-C
12alkoxyl group, halo C
1-C
12alkoxyl group, C
1-C
12alkylthio, halo C
1-C
12alkylthio, C
2-C
12thiazolinyl, halo C
2-C
12thiazolinyl, C
2-C
12alkynyl, halo C
2-C
12alkynyl, C
3-C
12alkene oxygen base, halo C
3-C
12alkene oxygen base, C
3-C
12alkynyloxy group, halo C
3-C
12alkynyloxy group, C
1-C
12alkyl sulphinyl, halo C
1-C
12alkyl sulphinyl, C
1-C
12alkyl sulphonyl, halo C
1-C
12alkyl sulphonyl, C
1-C
12alkyl-carbonyl, halo C
1-C
12alkyl-carbonyl, C
1-C
12alkyl-carbonyl oxygen base, C
1-C
12alkyl-carbonyl-amino, C
1-C
12alkyl sulphonyl oxygen base, C
1-C
12alkoxy carbonyl, C
1-C
12alkoxy carbonyl C
1-C
12alkyl, C
1-C
12alkoxycarbonyl amino, C
1-C
12alkoxy C
1-C
12alkoxyl group or C
1-C
12alkoxy carbonyl C
1-C
12alkoxyl group;
R
8be selected from hydrogen, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxy C
1-C
8alkyl, cyano group C
1-C
8alkyl or C
3-C
6cycloalkyl, the unsubstituted or aryl that replaced further by the following group of 1-5 or heteroaryl: halogen, cyano group, nitro, C
1-C
6alkyl, C
1-C
6alkoxyl group, C
1-C
6alkylthio, C
3-C
6cycloalkyl, C
2-C
6thiazolinyl, C
2-C
6alkynyl, halo C
1-C
6alkyl, halo C
1-C
6alkoxyl group, halo C
1-C
6alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
6thiazolinyl, halo C
2-C
6alkynyl, C
1-C
6alkyl sulphinyl, C
1-C
6alkyl sulphonyl, C
1-C
6alkylamino, two (C
1-C
6alkyl) amino, C
1-C
6alkyl-carbonyl, C
1-C
6alkoxy carbonyl, C
1-C
6alkyl amino-carbonyl, unsubstituted or be independently selected from by 1-5 the aryl or heteroaryl that following group replaces further: hydrogen, halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
9be selected from hydrogen, halogen, cyano group, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, cyano group C
1-C
8alkyl, cyano group C
1-C
8alkoxyl group, C
3-C
8alkene oxygen base, halo C
3-C
8alkene oxygen base, C
3-C
8alkynyloxy group, halo C
3-C
8alkynyloxy group, C
1-C
8alkylthio, halo C
1-C
8alkylthio, C
1-C
8alkyl sulphinyl, halo C
1-C
12alkyl sulphinyl, C
1-C
8alkyl sulphonyl, halo C
1-C
8alkyl sulphonyl, phenyl that is unsubstituted or that be independently selected from following group replace further by 1-5: halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
1-C
8alkylthio, C
3-C
8cycloalkyl, C
2-C
8thiazolinyl, C
2-C
8alkynyl, halo C
1-C
8alkylthio, halo C
3-C
8cycloalkyl, halo C
2-C
8thiazolinyl, halo C
2-C
8alkynyl, C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl, C
1-C
8alkylamino, two (C
1-C
8alkyl) amino, C
1-C
8alkyl-carbonyl, C
1-C
8alkoxy carbonyl or C
1-C
8alkyl amino-carbonyl;
R
10be selected from hydrogen, halogen, cyano group, nitro, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
1-C
8alkylthio, halo C
1-C
8alkylthio, C
1-C
8alkyl sulphinyl, halo C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl or halo C
1-C
8alkyl sulphonyl;
R
10' be selected from hydrogen, halogen, cyano group, C
1-C
8alkyl, halo C
1-C
8alkyl, cyano group C
1-C
8alkyl or C
3-C
6cycloalkyl;
And the present invention does not comprise following 3 compounds:
2. compound according to claim 1, is characterized in that: described compound as shown in general formula I, II or Ш, wherein in general formula I, II or Ш,
A is selected from hydrogen, hydroxyl, formyl radical, C
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
3-C
8cycloalkyl, C
1-C
8alkylthio, C
2-C
8enylsulfanyl, C
2-C
8thiazolinyl, C
2-C
8alkynyl, halo C
2-C
8thiazolinyl, halo C
2-C
8alkynyl, C
1-C
8alkoxy C
1-C
8alkyl, halo C
1-C
8alkoxy C
1-C
8alkyl, C
1-C
8alkylthio C
1-C
8alkyl, halo C
1-C
8alkylthio C
1-C
8alkyl, C
1-C
8alkyl sulphinyl, halo C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl, halo C
1-C
8alkyl sulphonyl, C
1-C
8alkyl amino sulfonyl, two (C
1-C
8alkyl) amino-sulfonyl, C
1-C
8alkylsulfonyl aminocarbonyl, C
1-C
8alkyl-carbonyl-amino alkylsulfonyl, C
3-C
8cycloalkyloxycarbonyl, C
1-C
8alkyl-carbonyl, halo C
1-C
8alkyl-carbonyl, C
1-C
8alkoxy carbonyl, halo C
1-C
8alkoxy carbonyl, C
1-C
8alkyl-carbonyl C
1-C
8alkyl, C
1-C
8alkoxy carbonyl C
1-C
8alkyl, C
1-C
8alkyl amino-carbonyl, two (C
1-C
8alkyl) aminocarboxyl, C
2-C
8allyloxycarbonyl, C
2-C
8alkynyloxycar bonyl, C
1-C
8alkoxy C
1-C
8alkoxy carbonyl, C
1-C
8alkylamino sulfenyl, two (C
1-C
8alkyl) amino sulfenyl, (mixing) aryl carbonyl C that is unsubstituted or that replaced further by the following group of 1-3
1-C
6alkyl, (mixing) aryl carbonyl, (mixing) aryloxycarbonyl, (mixing) aryl C
1-C
6alkyloxycarbonyl or (mixing) aryl C
1-C
6alkyl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen and pyridine ring 3,4 or 5 carbon are directly connected
2cR
ar
b-or-CH
2cR
ar
bcR
ar
b-;
R
a, R
bmay be the same or different, be selected from hydrogen, C respectively
1-C
8alkyl, C
3-C
8cycloalkyl, C
2-C
8thiazolinyl, C
2-C
8alkynyl, halo C
2-C
8thiazolinyl, halo C
2-C
8alkynyl, C
1-C
8alkoxy C
1-C
8alkyl, aryl C that is unsubstituted or that replaced further by 1-3 following group
1-C
4alkyl or heteroaryl C
1-C
4alkyl: halogen, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group; Or R
a, R
bc is formed with the carbon be connected
3-C
8ring;
X is selected from O or S;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C respectively
1-C
8alkyl, halo C
1-C
8alkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
3-C
8cycloalkyl, C
2-C
8thiazolinyl, C
2-C
8alkynyl, C
2-C
8alkene oxygen base, halo C
2-C
8alkene oxygen base, C
2-C
8alkynyloxy group, halo C
2-C
8alkynyloxy group, C
1-C
8alkylthio, halo C
1-C
8alkylthio, C
1-C
8alkoxy C
1-C
8alkyl, halo C
1-C
8alkoxy C
1-C
8alkyl, C
1-C
8alkylthio C
1-C
8alkyl, halo C
1-C
8alkylthio C
1-C
8alkyl, C
1-C
8alkyl sulphinyl, halo C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl, halo C
1-C
8alkyl sulphonyl, C
1-C
8alkyl amino sulfonyl, C
1-C
8alkylamino, halo C
1-C
8alkylamino, two (C
1-C
8alkyl) amino, C
1-C
8alkoxy carbonyl, CONH
2, C
1-C
8alkyl amino-carbonyl, two (C
1-C
8alkyl) aminocarboxyl, cyano group C
1-C
8alkoxyl group, C
1-C
8alkoxy carbonyl C
1-C
8alkyl, C
1-C
8alkyl amino-carbonyl C
1-C
8alkyl or two (C
1-C
8alkyl) aminocarboxyl C
1-C
8alkyl;
R
6, R
6', R
7may be the same or different, be selected from hydrogen, halogen, nitro, cyano group, C respectively
1-C
8alkyl, halo C
1-C
8alkyl, C
3-C
6cycloalkyl, C
1-C
8alkoxyl group, halo C
1-C
8alkoxyl group, C
1-C
8alkylthio, halo C
1-C
8alkylthio, C
2-C
8thiazolinyl, halo C
2-C
8thiazolinyl, C
2-C
8alkynyl, halo C
2-C
8alkynyl, C
3-C
8alkene oxygen base, halo C
3-C
8alkene oxygen base, C
3-C
8alkynyloxy group, halo C
3-C
8alkynyloxy group, C
1-C
8alkyl sulphinyl, halo C
1-C
8alkyl sulphinyl, C
1-C
8alkyl sulphonyl, halo C
1-C
8alkyl sulphonyl, C
1-C
8alkyl-carbonyl, halo C
1-C
8alkyl-carbonyl, C
1-C
8alkyl-carbonyl oxygen base, C
1-C
8alkyl-carbonyl-amino, C
1-C
8alkyl sulphonyl oxygen base, C
1-C
8alkoxy carbonyl, C
1-C
8alkoxy carbonyl C
1-C
8alkyl, C
1-C
8alkoxycarbonyl amino, C
1-C
8alkoxy C
1-C
8alkoxyl group or C
1-C
8alkoxy carbonyl C
1-C
8alkoxyl group;
R
8be selected from hydrogen, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxy C
1-C
3alkyl, cyano group C
1-C
6alkyl or C
3-C
6cycloalkyl, the unsubstituted or aryl that replaced further by the following group of 1-5 or heteroaryl: halogen, cyano group, nitro, C
1-C
4alkyl, C
1-C
4alkoxyl group, C
1-C
4alkylthio, C
3-C
6cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, halo C
1-C
4alkyl, halo C
1-C
4alkoxyl group, halo C
1-C
4alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
4thiazolinyl, halo C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkyl-carbonyl, C
1-C
4alkoxy carbonyl, C
1-C
4alkyl amino-carbonyl, unsubstituted or be independently selected from by 1-5 the phenyl or pyridyl that following group replaces further: hydrogen, halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
9be selected from hydrogen, halogen, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group, halo C
1-C
6alkoxyl group, cyano group C
1-C
6alkyl, cyano group C
1-C
6alkoxyl group, halo C
1-C
6alkylthio, halo C
1-C
6alkyl sulphinyl, halo C
1-C
6alkyl sulphonyl, phenyl that is unsubstituted or that be independently selected from following group replace further by 1-5: halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group, halo C
1-C
6alkoxyl group, C
1-C
6alkylthio, C
3-C
6cycloalkyl, C
2-C
6thiazolinyl, C
2-C
6alkynyl, halo C
1-C
6alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
6thiazolinyl, halo C
2-C
6alkynyl, C
1-C
6alkyl sulphinyl, C
1-C
6alkyl sulphonyl, C
1-C
6alkylamino, two (C
1-C
6alkyl) amino, C
1-C
6alkyl-carbonyl, C
1-C
6alkoxy carbonyl or C
1-C
6alkyl amino-carbonyl;
R
10be selected from hydrogen, halogen, cyano group, nitro, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group, halo C
1-C
6alkoxyl group, C
1-C
6alkylthio, halo C
1-C
6alkylthio, C
1-C
6alkyl sulphinyl, halo C
1-C
6alkyl sulphinyl, C
1-C
6alkyl sulphonyl or halo C
1-C
6alkyl sulphonyl;
R
10' be selected from hydrogen, halogen, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, cyano group C
1-C
6alkyl or C
3-C
6cycloalkyl.
3. compound according to claim 2, is characterized in that: described compound as shown in general formula I, II or Ш, wherein in general formula I, II or Ш,
A is selected from hydrogen, C
1-C
4alkyl, C
1-C
4alkoxy carbonyl, C
1-C
4alkoxy carbonyl C
1-C
4alkyl, C
1-C
4alkoxyl group
Carbonyl, C
1-C
4alkyl-carbonyl C
1-C
4alkyl;
B is selected from carbon nitrogen the singly-bound ,-CH that amide nitrogen and pyridine ring 3,4 or 5 carbon are directly connected
2cR
ar
b-or-CH
2cR
ar
bcR
ar
b-;
R
a, R
bmay be the same or different, be selected from hydrogen, methyl or ethyl respectively;
X is selected from O or S;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, hydroxyl, cyano group, carboxyl, amino, nitro, C respectively
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, C
3-C
4cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, C
2-C
4alkene oxygen base, halo C
2-C
4alkene oxygen base, C
2-C
4alkynyloxy group, halo C
2-C
4alkynyloxy group, C
1-C
4alkylthio, halo C
1-C
4alkylthio, C
1-C
4alkoxy C
1-C
4alkyl, halo C
1-C
4alkoxy C
1-C
4alkyl, C
1-C
4alkylthio C
1-C
4alkyl, halo C
1-C
4alkylthio C
1-C
4alkyl, C
1-C
4alkyl sulphinyl, halo C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, halo C
1-C
4alkyl sulphonyl, C
1-C
4alkyl amino sulfonyl, C
1-C
4alkylamino, halo C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkoxy carbonyl, CONH
2, C
1-C
4alkyl amino-carbonyl, two (C
1-C
4alkyl) aminocarboxyl, cyano group C
1-C
12alkoxyl group, C
1-C
4alkoxy carbonyl C
1-C
4alkyl, C
1-C
4alkyl amino-carbonyl C
1-C
4alkyl or two (C
1-C
4alkyl) aminocarboxyl C
1-C
4alkyl;
R
6, R
6', R
7may be the same or different, be selected from hydrogen, halogen, nitro, cyano group, C respectively
1-C
4alkyl, halo C
1-C
4alkyl, C
3-C
6cycloalkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, C
1-C
4alkylthio, halo C
1-C
4alkylthio, C
2-C
4thiazolinyl, C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkyl-carbonyl or C
1-C
4alkoxy C
1-C
4alkoxyl group;
R
8be selected from hydrogen, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxy C
1-C
3alkyl, cyano group C
1-C
4alkyl, C
3-C
6cycloalkyl, the unsubstituted or aryl that replaced further by the following group of 1-5 or heteroaryl: halogen, cyano group, nitro, C
1-C
4alkyl, C
1-C
4alkoxyl group, C
1-C
4alkylthio, C
3-C
6cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, halo C
1-C
4alkyl, halo C
1-C
4alkoxyl group, halo C
1-C
4alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
4thiazolinyl, halo C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkyl-carbonyl, C
1-C
4alkoxy carbonyl, C
1-C
4alkyl amino-carbonyl, unsubstituted or be independently selected from by 1-5 the phenyl or pyridyl that following group replaces further: hydrogen, halogen, cyano group, nitro, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
9be selected from hydrogen, halogen, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, cyano group C
1-C
4alkyl, cyano group C
1-C
4alkoxyl group, halo C
1-C
4alkylthio, halo C
1-C
4alkyl sulphinyl, halo C
1-C
4alkyl sulphonyl, phenyl that is unsubstituted or that be independently selected from following group replace further by 1-5: halogen, cyano group, nitro, hydroxyl, amino, sulfydryl, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, C
1-C
4alkylthio, C
3-C
6cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, halo C
1-C
4alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
4thiazolinyl, halo C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkyl-carbonyl, C
1-C
4alkoxy carbonyl or C
1-C
4alkyl amino-carbonyl;
R
10be selected from hydrogen, halogen, cyano group, nitro, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, C
1-C
4alkylthio, halo C
1-C
4alkylthio, C
1-C
4alkyl sulphinyl, halo C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl or halo C
1-C
4alkyl sulphonyl;
R
10' be selected from hydrogen, halogen, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, cyano group C
1-C
4alkyl or C
3-C
6cycloalkyl.
4. compound according to claim 3, is characterized in that: described compound is as shown in general formula I-A, I-B, I-C, I-D, II-A or Ш-A:
In formula:
A is selected from hydrogen;
R
a, R
bmay be the same or different, be selected from hydrogen, methyl or ethyl respectively;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, C respectively
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
6, R
6', R
7may be the same or different, be selected from hydrogen, halogen, nitro, cyano group, C respectively
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group or C
1-C
4alkyl-carbonyl;
R
8' be selected from hydrogen, C
1-C
4alkyl or C
3-C
6cycloalkyl;
R
9be selected from hydrogen, halogen, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group, halo C
1-C
4alkoxyl group, cyano group C
1-C
3alkyl, cyano group C
1-C
3alkoxyl group, halo C
1-C
3alkylthio, halo C
1-C
3alkyl sulphinyl, halo C
1-C
3alkyl sulphonyl, phenyl that is unsubstituted or that be independently selected from following group replace further by 1-3: halogen, cyano group, nitro, C
1-C
4alkyl, C
1-C
4alkoxyl group, C
1-C
4alkylthio, C
3-C
6cycloalkyl, C
2-C
4thiazolinyl, C
2-C
4alkynyl, halo C
1-C
4alkyl, halo C
1-C
4alkoxyl group, halo C
1-C
4alkylthio, halo C
3-C
6cycloalkyl, halo C
2-C
4thiazolinyl, halo C
2-C
4alkynyl, C
1-C
4alkyl sulphinyl, C
1-C
4alkyl sulphonyl, C
1-C
4alkylamino, two (C
1-C
4alkyl) amino, C
1-C
4alkyl-carbonyl, C
1-C
4alkoxy carbonyl or C
1-C
4alkyl amino-carbonyl;
R
10be selected from hydrogen, halogen, cyano group, nitro, C
1-C
4alkyl, halo C
1-C
4alkyl, halo C
1-C
4alkylthio or halo C
1-C
4alkyl sulphinyl;
R
10' be selected from hydrogen, halogen, cyano group, C
1-C
4alkyl or halo C
1-C
4alkyl;
R
11, R
12, R
13, R
14may be the same or different, be selected from hydrogen, halogen, cyano group, C respectively
1-C
4alkyl, halo C
1-C
4alkyl or halo C
1-C
4alkoxyl group;
Y is selected from N or CR
15, wherein R
15be selected from hydrogen, halogen, C
1-C
4alkyl or halo C
1-C
4alkyl.
5. compound according to claim 4, is characterized in that: described compound is as in general formula I-A, I-B, I-C, I-D, II-A or Ш-A
A, R
a, R
b, R
6, R
6', R
7all be selected from hydrogen;
R
1, R
2, R
3, R
4, R
5may be the same or different, be selected from hydrogen, halogen, C respectively
1-C
4alkyl, halo C
1-C
4alkyl or C
1-C
4alkoxyl group;
R
8' be selected from C
1-C
4alkyl;
R
9be selected from halogen, C
1-C
4alkyl or halo C
1-C
4alkyl;
R
10or R
10' be selected from hydrogen, halogen or C
1-C
4alkyl;
R
11, R
12, R
13, R
14may be the same or different, be selected from hydrogen or halogen respectively;
Y is selected from N.
6. compound according to claim 5, is characterized in that: described compound as in general formula I-A, I-B, I-C, I-D, II-A or Ш-A,
A, R
a, R
b, R
6, R
6', R
7all be selected from hydrogen;
Wherein in general formula I-A, R
1, R
10be selected from hydrogen or halogen; R
2be selected from hydrogen, halogen or C
1-C
4alkyl; R
3be selected from hydrogen, halogen or halo C
1-C
4alkyl; R
4be selected from hydrogen, halogen, C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkyl; R
5be selected from hydrogen; R
8', R
9be selected from C
1-C
4alkyl;
In general formula I-B, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from halogen; R
8' be selected from C
1-C
4alkyl; R
9be selected from C
1-C
4alkyl or halo C
1-C
4alkyl; R
10' be selected from hydrogen or C
1-C
4alkyl;
In general formula I-C, Y=N; R
1be selected from hydrogen or halo C
1-C
4alkyl; R
2be selected from hydrogen or halogen; R
3, R
5, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen, halogen, C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkyl; R
9, R
11be selected from halogen;
In general formula I-D, Y=N; R
1, R
3, R
5be selected from hydrogen or halogen; R
2, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen or C
1-C
4alkyl; R
9, R
11be selected from halogen;
In general formula I I-A, R
1, R
2, R
3, R
5be selected from hydrogen; R
4, R
10be selected from halogen; R
8', R
9be selected from C
1-C
4alkyl;
In general formula III-A, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from hydrogen or halogen; R
8', R
9be selected from C
1-C
4alkyl; R
10be selected from halogen.
7. compound according to claim 6, is characterized in that: described compound as in general formula I-A, I-B, I-C, I-D, II-A or Ш-A,
A, R
a, R
b, R
6, R
6', R
7all be selected from hydrogen;
In general formula I-A, R
1, R
10be selected from hydrogen or chlorine; R
2be selected from hydrogen, chlorine or methyl; R
3be selected from hydrogen, chlorine or trifluoromethyl; R
4be selected from hydrogen, chlorine, methyl, methoxyl group or trifluoromethyl; R
5be selected from hydrogen; R
8' be selected from methyl; R
9be selected from methyl or ethyl;
In general formula I-B, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from chlorine; R
8' be selected from methyl; R
9be selected from methyl or trifluoromethyl; R
10' be selected from hydrogen or methyl;
In general formula I-C, Y=N; R
1be selected from hydrogen or trifluoromethyl; R
2be selected from hydrogen or chlorine; R
3, R
5, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen, chlorine, methyl, methoxyl group or trifluoromethyl; R
9be selected from bromine; R
11be selected from chlorine;
In general formula I-D, Y=N; R
1, R
3, R
5be selected from hydrogen or chlorine; R
2, R
10, R
12, R
13, H
14be selected from hydrogen; R
4be selected from hydrogen or methyl; R
9be selected from bromine; R
11be selected from chlorine;
In general formula I I-A, R
1, R
2, R
3, R
5be selected from hydrogen; R
4, R
10be selected from chlorine; R
8' be selected from methyl; R
9be selected from methyl or ethyl;
In general formula III-A, R
1, R
2, R
3, R
5be selected from hydrogen; R
4be selected from hydrogen or chlorine; R
8', R
9be selected from methyl; R
10be selected from chlorine.
8. a general formula I according to claim 1, II or Ш compound are used as the purposes preparing sterilant, Insecticiding-miticiding agent medicine in agricultural, forestry or health field.
9. a sterilization and disinsection miticide composition, is characterized in that: containing, for example general formula I according to claim 1, II or Ш compound as active ingredient, and in composition, the weight percentage of active ingredient is 0.5-99%.
10. prevent and treat a method for germ, insect evil mite, it is characterized in that: the composition according to claim 9 of significant quantity is imposed on described germ, insect evil mite or its growth medium.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113880765A (en) * | 2021-09-30 | 2022-01-04 | 南京林业大学 | Diphenyl ether group-containing 4- (1H-pyrazole-1-yl) biphenyl formamide compound and application thereof |
| US11641858B2 (en) | 2016-04-13 | 2023-05-09 | Redag Crop Protection Ltd. | Agricultural chemicals |
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| CN104974136B (en) | 2017-10-20 |
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