CN101298435B - O-formammidotiazol-benzamide compounds and use thereof - Google Patents
O-formammidotiazol-benzamide compounds and use thereof Download PDFInfo
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- CN101298435B CN101298435B CN2007100111786A CN200710011178A CN101298435B CN 101298435 B CN101298435 B CN 101298435B CN 2007100111786 A CN2007100111786 A CN 2007100111786A CN 200710011178 A CN200710011178 A CN 200710011178A CN 101298435 B CN101298435 B CN 101298435B
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- 0 **C(c1cc(*)cc(*)c1NC(c1cc(*)n[n]1-c1ncccc1Cl)=O)=O Chemical compound **C(c1cc(*)cc(*)c1NC(c1cc(*)n[n]1-c1ncccc1Cl)=O)=O 0.000 description 1
Abstract
The invention discloses anthranilic diamide compounds and application thereof; the structures of the compounds are showed by a general formula I; the definitions of each substitutional group are seen in an instruction; the anthranilic diamide compounds of the invention have broad-spectrum insecticidal activity and is very effective to lepidopterous pests which include European corn borers, sugarcane borers, codling moths, lessorapple-worms and gypsy moths; the activity is especially better to diamond back moths; better effect can be obtained under low dosage. Simultaneously, a part of the compounds also have better sterilizing activity and can be used for controlling rice blasts, cucumber downy mildews and anthraxes.
Description
Technical field
The invention belongs to agricultural insecticidal, sterilant field.Relate to a kind of O-formammidotiazol-benzamide compounds and application thereof specifically.
Background technology
O-formammidotiazol-benzamide compounds (ryania acceptor class) is effective sterilant of the control lepidoptera pest developed in recent years.
The compound that has insecticidal activity is as follows disclosed among the patent WO2001070671:
The compound that has insecticidal activity is as follows disclosed among the patent WO03015519:
The compound that has insecticidal activity is as follows disclosed among the patent WO2004033468:
The compound that has insecticidal activity is as follows disclosed among the patent WO2004067528:
Above patent (application) though in all disclosed compounds with The compounds of this invention similarity is arranged, still there is significant difference in structure, and related compound is not all seen the report with fungicidal activity in the document.
Summary of the invention
The object of the present invention is to provide a kind of O-formammidotiazol-benzamide compounds that under very little dosage, just can control various disease and pests, it can be applicable to agricultural and goes up disease and insect pest with the control crop.
Technical scheme of the present invention is following:
The present invention provides a kind of O-formammidotiazol-benzamide compounds, shown in general formula I:
In the formula:
A is selected from CR
12Or N; R
12Be selected from hydrogen or halogen;
X is selected from O, S or NR
16R
16=H, CN, OCH
3Or NHCH
3
Y is selected from NR
X, O or S;
R
1, R
2Can be identical or different, be selected from hydrogen, halogen, cyanic acid, nitro, C respectively
1-C
6Alkyl, C
2-C
6Thiazolinyl, C
2-C
6Alkynyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, C
1-C
6Alkane alkylsulfonyl, C
1-C
6Alkyl-carbonyl, C
1-C
6Alkoxy C
1-C
6Alkyl, C
1-C
6Alkoxy carbonyl, C
1-C
6Alkoxy carbonyl C
1-C
6Alkyl, halo C
1-C
6Alkoxy C
1-C
6Alkyl, unsubstituted or by the substituted amino of following group, amino C
1-C
6Alkyl, aryl, aryloxy, aryl C
1-C
6Alkyl, fragrant C
1-C
6Alkyl oxy, heteroaryl, heteroaryl C
1-C
6Alkyl, heteroaryl C
1-C
6Alkoxyl group: halogen, nitro, cyanic acid, C
1-C
6Alkyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group, halo C
1-C
6Alkoxyl group, C
1-C
6Alkylthio or C
1-C
6Alkyl-carbonyl;
R
3Be selected from halogen, CSNH
2, OCH
2CN, 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
6Alkane alkylsulfonyl, halo C
1-C
6Alkane alkylsulfonyl, C
1-C
6Alkyl-carbonyl, C
1-C
6Alkoxyl group oximido, C
1-C
6Alkoxy C
1-C
6Alkyl, halo C
1-C
6Alkoxy C
1-C
6Alkyl, halo C
1-C
6Alkoxy C
1-C
6Alkoxyl group, C
1-C
6Alkylthio C
1-C
6Alkyl, halo C
1-C
6Alkylthio C
1-C
6Alkyl, C
2-C
6Alkene oxygen base, halo C
2-C
6Alkene oxygen base, OCH
2Ph, C
1-C
6Alkylamino C
1-C
6Alkoxyl group, halo C
1-C
6Alkylamino C
1-C
6Alkoxyl group, C
1-C
6Alkylamino, halo C
1-C
6Alkylamino, C
1-C
6Alkane sulfuryl amino, halo C
1-C
6The alkane sulfuryl amino or
R
13Be selected from hydrogen, C
1-C
6Alkyl, halo C
1-C
6Alkyl; R
14Be selected from C
1-C
6Alkyl, halo C
1-C
6Alkyl;
R
4Be selected from C
1-C
6Alkyl, halo C
1-C
6Alkyl, C
2-C
6Thiazolinyl, halo C
2-C
6Thiazolinyl, C
2-C
6Alkynyl, halo C
2-C
6Alkynyl, C
1-C
6Alkoxyl group, halo C
1-C
6Alkoxyl group, cyanic acid, NHCSNH
2, C (=NH) NH
2, C (=NH) NHNO
2, unsubstituted or by the substituted aryl of following group, aryloxy or heteroaryl: halogen, nitro, cyanic acid, C
1-C
6Alkyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group, halo C
1-C
6Alkoxyl group, C
1-C
6Alkylthio or C
1-C
6Alkyl-carbonyl or
Or
R
15Be selected from hydrogen, C
1-C
6Alkyl, halo C
1-C
6Alkyl, NR
Y, OR
Y, SR
YR
16Be selected from hydrogen, cyanic acid, NO
2Or C
1-C
6Alkoxy carbonyl; R
YBe selected from hydrogen, C
1-C
6Alkyl, C
1-C
6Alkyl-carbonyl, C
1-C
6Alkoxy carbonyl, C
1-C
6Alkane alkylsulfonyl, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl; R
XCan be selected from hydrogen, C
1-C
6Alkyl, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl or and R
YForm five circle or six annulus;
Perhaps R
4Be selected from B-Z-Q or B-ZM, wherein:
B is selected from CH
2, CH
2CH
2, CH
2CH
2CH
2, CH
2CH
2CH
2CH
2, CH (CH
3), CH (CH
3) CH
2, CH (CH
3) CH (CH
3), CH (CH
3) CH
2CH
2, CH
2CH (CH
3) CH
2, CH
2CO, CH (CH
3) CO, CH
2CH
2CO, CH
2CH
2CH
2CO, CH
2CH
2OCH
2, CH
2CH
2OCH
2CH
2, CH
2CH
2NHCH
2CH
2, CH
2CH
2SCH
2CH
2, CH
2CH
2SOCH
2CH
2, CH
2CH
2SO
2CH
2CH
2, CH
2CH
2OCH
2CO, CH
2CH
2NHCH
2CO, CH
2COCH
2, NHCH
2, NHCH
2CH
2, OCH
2, N=CHCH=N, N=C (CH
3) C (CH
3)=N, N (CH
3) CH
2CH
2N (CH
3),
Work as R
4When being selected from B-Z-Q, Z is selected from O, S or NH, and Q is selected from any among the Q1-Q29 as follows; Or R
4When being selected from B-Z-Q, B-Z-is selected from O, S or NH, and Q is selected from any among the Q1-Q29 as follows;
R
8Be selected from hydrogen, halogen, cyanic acid, nitro, C
1-C
6Alkyl, C
2-C
6Thiazolinyl, C
2-C
6Alkynyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, C
1-C
6Alkane alkylsulfonyl, C
1-C
6Alkyl-carbonyl, C
1-C
6Alkoxy C
1-C
6Alkyl, C
1-C
6Alkoxy carbonyl, C
1-C
6Alkoxy carbonyl C
1-C
6Alkyl, halo C
1-C
6Alkoxy C
1-C
6Alkyl, unsubstituted or by the substituted amino of following group, C
1-C
6Alkyl, aryl, aryloxy, aryl C
1-C
6Alkyl, fragrant C
1-C
6Alkyl oxy, heteroaryl, heteroaryl C
1-C
6Alkyl, heteroaryl C
1-C
6Alkoxyl group: halogen, nitro, cyanic acid, C
1-C
6Alkyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group, halo C
1-C
6Alkoxyl group, C
1-C
6Alkylthio or C
1-C
6Alkyl-carbonyl;
R
9Be selected from halogen, CSNH
2, OCH
2CN, C
1-C
6Alkyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group, halo G
1-C
6Alkoxyl group, C
1-C
6Alkylthio, halo C
1-C
6Alkylthio, C
1-C
6Alkane alkylsulfonyl, halo C
1-C
6Alkane alkylsulfonyl, C
1-C
6Alkyl-carbonyl, C
1-C
6Alkoxyl group oximido, halo C
1-C
6Alkoxy C
1-C
6Alkoxyl group, C
1-C
6Alkoxy C
1-C
6Alkyl, halo C
1-C
6Alkoxy C
1-C
6Alkyl, C
1-C
6Alkylthio C
1-C
6Alkyl, halo C
1-C
6Alkylthio C
1-C
6Alkyl, C
2-C
6Alkene oxygen base, halo C
2-C
6Alkene oxygen base, OCH
2Ph, C
1-C
6Alkylamino C
1-C
6Alkoxyl group, halo C
1-C
6Alkylamino C
1-C
6Alkoxyl group, C
1-C
6Alkylamino, halo C
1-C
6Alkylamino, C
1-C
6Alkane sulfuryl amino or halo C
1-C
6The alkane sulfuryl amino;
R
10Be selected from cyanic acid or C
1-C
6Alkyl-carbonyl;
R
11Be selected from C
1-C
6Alkylthio, C
1-C
6Alkane alkylsulfonyl, C
1-C
6Alkyl sulfinyl, halo C
1-C
6Alkylthio, halo G
1-C
6Alkyl sulfinyl or halo C
1-C
6The alkane alkylsulfonyl;
Work as R
4When being selected from B-ZM, Z is selected from NR
17: R
17Be selected from H
2, (CH
3)
2Or (C
2H
5)
2
M is selected from HCl, CH
3CO
2H, CF
3CO
2H, Hydrocerol A, DL-oxysuccinic acid, tartrate, toxilic acid, phenylformic acid, Phenylsulfonic acid or Whitfield's ointment;
R
5, R
6, R
7Can be identical or different, be selected from hydrogen, halogen, cyanic acid, nitro, C respectively
1-C
6Alkyl, C
2-C
6Thiazolinyl, C
2-C
6Alkynyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, C
1-C
6Alkane alkylsulfonyl, C
1-C
6Alkyl-carbonyl, C
1-C
6Alkoxy C
1-C
6Alkyl, C
1-C
6Alkoxy carbonyl, C
1-C
6Alkoxy carbonyl C
1-C
6Alkyl or halo C
1-C
6Alkoxy C
1-C
6Alkyl.
Comparatively preferred compound is among the present invention: in the general formula I
A is selected from CR
12Or N; R
12Be selected from hydrogen or halogen;
X is selected from O, S or NR
16R
16=H, CN, OCH
3, NHCH
3
Y is selected from NR
X, O or S;
R
1, R
2Can be identical or different, be selected from hydrogen, halogen, cyanic acid, nitro, C respectively
1-C
3Alkyl, halo C
1-C
3Alkyl, C
1-C
3Alkoxyl group, C
1-C
3Alkylthio, C
1-C
3Alkane alkylsulfonyl, C
1-C
3Alkyl-carbonyl, C
1-C
3Alkoxy C
1-C
3Alkyl, C
1-C
3Alkoxy carbonyl, C
1-C
3Alkoxy carbonyl C
1-C
3Alkyl, do not replace or substituted amino C
1-C
3Alkyl, amino, its substituting group is selected from halogen, nitro, cyanic acid, C
1-C
3Alkyl, halo C
1-C
3Alkyl, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group, C
1-C
3Alkylthio or C
1-C
3Alkyl-carbonyl;
R
3Be selected from halogen, CS NH
2, OCH
2CN, C
1-C
3Alkyl, halo C
1-C
3Alkyl, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group, C
1-C
3Alkylthio, halo C
1-C
3Alkylthio, C
1-C
3Alkane alkylsulfonyl, halo C
1-C
3Alkane alkylsulfonyl, C
1-C
3Alkyl-carbonyl, C
1-C
3Alkoxyl group oximido, C
1-C
3Alkoxy C
1-C
3Alkyl, halo C
1-C
3Alkoxy C
1-C
3Alkyl, halo C
1-C
3Alkoxy C
1-C
3Alkoxyl group, C
1-C
3Alkylthio C
1-C
3Alkyl, halo C
1-C
3Alkylthio C
1-C
3Alkyl, C
2-C
3Alkene oxygen base, halo C
2-C
3Alkene oxygen base, OCH
2Ph, C
1-C
3Alkylamino C
1-C
3Alkoxyl group, halo C
1-C3 alkylamino C
1-C
3Alkoxyl group, C
1-C
3Alkylamino, halo C
1-C
3Alkylamino, C
1-C
3Alkane sulfuryl amino, halo C
1-C
3The alkane sulfuryl amino or
R
13Be selected from hydrogen, C
1-C
3Alkyl, halo C
1-C
3Alkyl; R
14Be selected from C
1-C
3Alkyl, halo C
1-C
3Alkyl;
R
4Be selected from C
1-C
3Alkyl, halo C
1-C
3Alkyl, C
2-C
3Thiazolinyl, halo C
2-C
3Thiazolinyl, C
2-C
3Alkynyl, halo C
2-C
3Alkynyl, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group, cyanic acid, NHCSNH
2, C (=NH) NH
2, C (=NH) NHNO
2, unsubstituted or by the further substituted aryl of following group, aryloxy or heteroaryl: halogen, nitro, cyanic acid, C
1-C
3Alkyl, halo C
1-C
3Alkyl, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group, C
1-C
3Alkylthio or C
1-C
3Alkyl-carbonyl or
Or
R
15Be selected from hydrogen, C
1-C
6Alkyl, halo C
1-C
6Alkyl, NR
Y, OR
Y, SR
YR
16Be selected from hydrogen, cyanic acid, NO
2Or C
1-C
6Alkoxy carbonyl; R
YBe selected from hydrogen, C
1-C
6Alkyl, C
1-C
6Alkyl-carbonyl, C
1-C
6Alkoxy carbonyl, C
1-C
6Alkane alkylsulfonyl, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl; R
XCan be selected from hydrogen, C
1-C
6Alkyl, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl or and R
YForm five circle or six annulus;
Perhaps R
4Be selected from B-Z-Q or B-ZM, wherein:
B is selected from CH
2, CH
2CH
2, CH
2CH
2CH
2, CH
2CH
2CH
2CH
2, CH (CH
3), CH (CH
3) CH
2, CH (CH
3) CH (CH
3), CH
2CO, CH (CH
3) CO, CH
2CH
2CO, CH
2CH
2OCH
2, CH
2CH
2OCH
2CH
2, CH
2CH
2NHCH
2CH
2, CH
2CH
2SCH
2CH
2, CH
2CH
2SOCH
2CH
2, CH
2CH
2SO
2CH
2CH
2, CH
2CH
2OCH
2CO, CH
2CH
2NHCH
2CO, CH
2COCH
2, NHCH
2, NHCH
2CH
2, OCH
2, N=CHCH=N, N=C (CH
3) C (CH
3)=N, N (CH
3) CH
2CH
2N (CH
3),
Work as R
4When being selected from B-Z-Q, Z is selected from O, S or NH, and Q is selected among the Q1-Q29 any one; Or R
4When being selected from B-Z-Q, B-Z-is selected from O, S or NH, and Q is selected among the Q1-Q29 any one;
R
8Be selected from hydrogen, halogen, cyanic acid, nitro, C
1-C
3Alkyl, C
2-C
3Thiazolinyl, C
2-C
3Alkynyl, C
1-C
3Haloalkyl, C
1-C
3Alkoxyl group, C
1-C
3Alkylthio, C
1-C
3Alkane alkylsulfonyl, C
1-C
3Alkyl-carbonyl, C
1-C
3Alkoxy C
1-C
3Alkyl, C
1-C
3Alkoxy carbonyl, C
1-C
3Alkoxy carbonyl C
1-C
3Alkyl, C
1-C
3Halogenated alkoxy C
1-C
3Alkyl, unsubstituted or by the substituted amino of following group, C
1-C
3Alkyl, aryl, aryloxy, aryl C
1-C
3Alkyl, fragrant C
1-C
3Alkyl oxy, heteroaryl, heteroaryl C
1-C
3Alkyl, heteroaryl C
1-C
3Alkoxyl group: halogen, nitro, cyanic acid, C
1-C
3Alkyl, halo C
1-C
3Alkyl, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group, C
1-C
3Alkylthio or C
1-C
3Alkyl-carbonyl;
R
9Be selected from halogen, CSNH
2, OCH
2CN, C
1-C
3Alkyl, halo C
1-C
3Alkyl, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group, C
1-C
3Alkylthio, halo C
1-C
3Alkylthio, C
1-C
3Alkane alkylsulfonyl, halo C
1-C
3Alkane alkylsulfonyl, C
1-C
3Alkyl-carbonyl, C
1-C
3Alkoxyl group oximido, halo C
1-C
3Alkoxy C
1-C
3Alkoxyl group, C
1-C
3Alkoxy C
1-C
3Alkyl, halo C
1-C
3Alkoxy C
1-C
3Alkyl, C
1-C
3Alkylthio C
1-C
3Alkyl, halo C
1-C
3Alkylthio C
1-C
3Alkyl, C
2-C
3Alkene oxygen base, halo C
2-C
3Alkene oxygen base, OCH
2Ph, C
1-C
3Alkylamino C
1-C
3Alkoxyl group, halo C
1-C
3Alkylamino C
1-C
3Alkoxyl group, C
1-C
3Alkylamino, halo C
1-C
3Alkylamino, C
1-C
3Alkane sulfuryl amino or halo C
1-C
3The alkane sulfuryl amino;
R
10Be selected from cyanic acid or C
1-C
3Alkyl-carbonyl;
R
11Be selected from C
1-C
3Alkylthio, C
1-C
3Alkane alkylsulfonyl, C
1-C
3Alkyl sulfinyl, halo C
1-C
3Alkylthio, halo C
1-C
3Alkyl sulfinyl, halo C
1-C
3The alkane alkylsulfonyl;
Work as R
4When being selected from B-ZM, Z is selected from NR
17R
17Be selected from H
2, (CH
3)
2Or (C
2H
5)
2
M is selected from HCl, CH
3CO
2H, CF
3CO
2H, Hydrocerol A, DL-oxysuccinic acid, tartrate, toxilic acid, phenylformic acid, Phenylsulfonic acid or Whitfield's ointment;
R
5, R
6, R
7Can be identical or different, be selected from hydrogen, halogen, cyanic acid, nitro, C respectively
1-C
3Alkyl, C
2-C
3Thiazolinyl, C
2-C
3Alkynyl, halo C
1-C
3Alkyl, C
1-C
3Alkoxyl group, C
1-C
3Alkylthio, C
1-C
3Alkane alkylsulfonyl, C
1-C
3Alkyl-carbonyl, C
1-C
3Alkoxy C
1-C
3Alkyl, C
1-C
3Alkoxy carbonyl, C
1-C
3Alkoxy carbonyl C
1-C
3Alkyl or halo C
1-C
3Alkoxy C
1-C
3Alkyl.
The further preferred compound of the present invention is: in the general formula I
A is selected from CR
12Or N; R
12Be selected from H or Cl;
X is selected from O, S or NR
16R
16=H, CN, OCH
3Or NHCH
3
Y is selected from NR
X, O or S;
R
1, R
2Can be identical or different, be selected from hydrogen, halogen, cyanic acid, nitro, methyl, OCH respectively
3, SO
2CH
3, COCH
3, CO
2CH
3, NHCH
3
R
3Be selected from halogen, CSNH
2, OCH
2CN, C
1-C
3Alkyl, halo C
1-C
3Alkyl, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group, C
1-C
3Alkylthio, halo C
1-C
3Alkylthio, C
1-C
3Alkane alkylsulfonyl, halo C
1-C
3Alkane alkylsulfonyl, C
1-C
3Alkyl-carbonyl, C
1-C
3Alkoxyl group oximido, C
1-C
3Alkoxy C
1-C
3Alkyl, halo C
1-C
3Alkoxy C
1-C
3Alkyl, halo C
1-C
3Alkoxy C
1-C
3Alkoxyl group, C
1-C
3Alkylthio C
1-C
3Alkyl, halo C
1-C
3Alkylthio C
1-C
3Alkyl, OCH
2Ph or
R
13Be selected from hydrogen, C
1-C
3Alkyl, halo C
1-C
3Alkyl; R
14Be selected from C
1-C
3Alkyl, halo C
1-C
3Alkyl;
R
4Be selected from C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group, cyanic acid, NHCSNH
2, C (=NH) NH
2, C (=NH) NHNO
2, unsubstituted or by the further substituted aryl of following group, aryloxy or heteroaryl: halogen, nitro, cyanic acid, C
1-C
3Alkyl, halo C
1-C
3Alkyl, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group, C
1-C
3Alkylthio or C
1-C
3Alkyl-carbonyl or
Or
R
15Be selected from hydrogen, C
1-C
6Alkyl, halo C
1-C
6Alkyl, NR
Y, OR
Y, SR
YR
16Be selected from hydrogen, cyanic acid, NO
2Or C
1-C
6Alkoxy carbonyl; R
YBe selected from hydrogen, C
1-C
6Alkyl, C
1-C
3Alkyl-carbonyl, C
1-C
3Alkoxy carbonyl, C
1-C
3Alkane alkylsulfonyl, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl; R
XCan be selected from hydrogen, C
1-C
3Alkyl, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl or and R
YForm five circle or six annulus;
Perhaps R
4Be selected from B-Z-Q or B-ZM, wherein:
B is selected from CH
2, CH
2CH
2, CH
2CH
2CH
2, CH
2CH
2CH
2CH
2, CH (CH
3), CH (CH
3) CH
2, CH (CH
3) CH (CH
3), CH
2CO, CH (CH
3) CO, CH
2CH
2CO, CH
2CH
2OCH
2, CH
2CH
2OCH
2CH
2, CH
2CH
2NHCH
2CH
2, CH
2CH
2SCH
2CH
2, CH
2CH
2SOCH
2CH
2, CH
2CH
2SO
2CH
2CH
2, CH
2CH
2OCH
2CO, CH
2CH
2NHCH
2CO, CH
2COCH
2, NHCH
2, NHCH
2CH
2, OCH
2, N=CHCH=N, N=C (CH
3) C (CH
3)=N, N (CH
3) CH
2CH
2N (CH
3),
Work as R
4When being selected from B-Z-Q, Z is selected from O, S or NH, and Q is selected among the Q1-Q29 any one; Or R
4When being selected from B-Z-Q, B-Z-is selected from O, S or NH, and Q is selected among the Q1-Q29 any one;
R
8Be selected from hydrogen, halogen or cyanic acid;
R
9Be selected from halogen, OCH
2CN, halo C
1-C
3Alkyl or halo C
1-C
3Alkoxyl group;
R
10Be selected from cyanic acid or C
1-C
3Alkyl-carbonyl;
R
11Be selected from C
1-C
3Alkylthio, C
1-C
3Alkane alkylsulfonyl, C
1-C
3Alkyl sulfinyl, halo C
1-C
3Alkylthio, halo C
1-C
3Alkyl sulfinyl or halo C
1-C
3The alkane alkylsulfonyl;
Work as R
4When being selected from B-ZM, Z is selected from NR
17R
17Be selected from H
2, (CH
3)
2Or (C
2H
5)
2
M is selected from HCl, CH
3CO
2H, CF
3CO
2H, Hydrocerol A, DL-oxysuccinic acid, tartrate, toxilic acid, phenylformic acid, Phenylsulfonic acid or Whitfield's ointment;
R
5, R
6, R
7Can be identical or different, be selected from hydrogen, halogen, cyanic acid, nitro, C respectively
1-C
3Alkyl or halo C
1-C
3Alkyl.
The further preferred compound of the present invention is: in the general formula I
A is selected from CR
12Or N; R
12Be selected from H or Cl;
X is selected from O, S or NR
16R
16=H, CN, OCH
3Or NHCH
3
Y is selected from NR
X, O or S;
R
1Be selected from H, halogen or methyl;
R
2Be selected from H, halogen or cyanic acid;
R
3Be selected from halogen, CF
3Or OCH
2CF
3
R
4Be selected from cyanic acid, NHCSNH
2, C (=NH) NH
2, C (=NH) NHNO
2, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group or
Or
R
15Be selected from hydrogen, C
1-C
3Alkyl, halo C
1-C
3Alkyl, NR
Y, OR
Y, SR
YR
16Be selected from hydrogen, cyanic acid, NO
2Or C
1-C
3Alkoxy carbonyl; R
YBe selected from hydrogen, C
1-C
3Alkyl, C
1-C
3Alkyl-carbonyl, C
1-C
3Alkoxy carbonyl, C
1-C
3Alkane alkylsulfonyl, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl; R
XCan be selected from hydrogen, C
1-C
3Alkyl, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl or and R
YForm five circle or six annulus;
Perhaps R
4Be selected from B-Z-Q or B-ZM, wherein:
B is selected from CH
2, CH
2CH
2, CH
2CH
2CH
2, CH
2CH
2CH
2CH
2, CH (CH
3), CH (CH
3) CH
2, CH (CH
3) CH (CH
3), CH
2CO, CH (CH
3) CO, CH
2CH
2CO, CH
2CH
2OCH
2, CH
2CH
2OCH
2CH
2, CH
2CH
2NHCH
2CH
2, CH
2CH
2SCH
2CH
2, CH
2CH
2SOCH
2CH
2, CH
2CH
2SO
2CH
2CH
2, CH
2CH
2OCH
2CO, CH
2CH
2NHCH
2CO, CH
2COCH
2, NHCH
2, NHCH
2CH
2, OCH
2, N=CHCH=N, N=C (CH
3) C (CH
3)=N, N (CH
3) CH
2CH
2N (CH
3);
Work as R
4When being selected from B-Z-Q, Z is selected from O, S or NH, and Q is selected among the Q1-Q29 any one; Or R
4When being selected from B-Z-Q, B-Z-is selected from O, S or NH, and Q is selected among the Q1-Q29 any one;
R
8Be selected from H, halogen or cyanic acid;
R
9Be selected from halogen, CF
3Or OCH
2CF
3
R
10Be selected from CN or COCH
3
R
11Be selected from SCH
3, SCH
2F, SCHF
2, SCF
3, SC
2H
5, SCH
2CH
2Cl, SOCH
3, SOCH
2F, SOCHF
2, SOCF
3, SOC
2H
5, SOCH
2CH
2Cl, SO
2CH
3, SO
2CH
2F, SO
2CHF
2, SO
2CF
3, SO
2C
2H
5Or SO
2CH
2CH
2Cl;
Work as R
4When being selected from B-ZM, Z is selected from NR
17R
17Be selected from H
2, (CH
3)
2Or (C
2H
5)
2
M is selected from HCl, CH
3CO
2H, CF
3CO
2H, Hydrocerol A, DL-oxysuccinic acid, tartrate, toxilic acid, phenylformic acid, Phenylsulfonic acid or Whitfield's ointment;
R
5, R
6, R
7Can be identical or different, be selected from H, Cl or CF respectively
3
The further preferred again compound of the present invention is: in the general formula I
A is selected from CR
12Or N; R
12Be selected from H or Cl;
X is selected from O, S or NR
16R
16=H, CN, OCH
3Or NHCH
3
Y is selected from NR
X, O or S;
R
1Be selected from H, halogen or methyl;
R
2Be selected from H, halogen or cyanic acid;
R
3Be selected from Cl, Br or CF
3
R
4Be selected from cyanic acid, NHCSNH
2, C (=NH) NH
2, C (=NH) NHNO
2, C
1-C
3Alkoxyl group, halo C
1-C
3Alkoxyl group or
Or
R
15Be selected from H, methyl or CF
3, NR
Y, OR
Y, SR
YR
16Be selected from hydrogen, cyanic acid, NO
2Or C
1-C
3Alkoxy carbonyl; R
YBe selected from hydrogen, C
1-C
3Alkyl, COCH
3, CO
2CH
3, SO
2CH
3, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl; R
XCan be selected from hydrogen, C
1-C
3Alkyl, chloro-pyridine methyl, chloro thiazole methyl, tetrahydrofuran methyl or and R
YForm five circle or six annulus;
Perhaps R
4Be selected from B-Z-Q or B-ZM, wherein:
B is selected from CH
2, CH
2CH
2, CH
2CH
2CH
2, CH
2CH
2CH
2CH
2, CH (CH
3), CH (CH
3) CH
2, CH (CH
3) CH (CH
3), CH
2CO, CH (CH
3) CO, CH
2CH
2CO, CH
2CH
2OCH
2, CH
2CH
2OCH
2CH
2, CH
2CH
2NHCH
2CH
2, CH
2CH
2SCH
2CH
2, CH
2CH
2SOCH
2CH
2, CH
2CH
2SO
2CH
2CH
2, CH
2CH
2OCH
2CO, CH
2CH
2NHCH
2CO, CH
2COCH
2, N=CHCH=N, N=C (CH
3) C (CH
3)=N, N (CH
3) CH
2CH
2N (CH
3);
Work as R
4When being selected from B-Z-Q, Z is selected from O, S or NH, and Q is selected among the Q1-Q29 any one; Or R
4When being selected from B-Z-Q, B-Z-is selected from O, S or NH, and Q is selected among the Q1-Q29 any one;
R
8Be selected from H, halogen or cyanic acid;
R
9Be selected from Cl, Br or CF
3
R
10Be selected from CN or COCH
3
R
11Be selected from SCH
2F, SCHF
2, SCF
3, SC
2H
5, SOCH
2F, SOCHF
2, SOCF
3, SOC
2H
5, SO
2CH
2F, SO
2CHF
2, SO
2CF
3Or SO
2C
2H
5
Work as R
4When being selected from B-ZM, Z is selected from NR
17R
17Be selected from H
2, (CH
3)
2Or (C
2H
5)
2
M is selected from HCl, CH
3CO
2H, CF
3CO
2H, Hydrocerol A, DL-oxysuccinic acid, tartrate, toxilic acid, phenylformic acid, Phenylsulfonic acid or Whitfield's ointment;
R
5, R
6, R
7Can be identical or different, be selected from H, Cl or CF respectively
3
In the definition of the compound of Formula I that provides above, it is following to compile used term General Definition:
Not replacing all substituting groups of expression all is hydrogen.
Substituent number can be 1～2 in the substituted amido.
Substituent number can be 1～5 in substituted phenyl, phenoxy, the benzyloxy.
Halogen: refer to fluorine, chlorine, bromine or iodine.
Alkyl: straight or branched alkyl, for example methyl, ethyl, propyl group, sec.-propyl or the tertiary butyl.
Haloalkyl: the straight or branched alkyl, the Wasserstoffatoms on these alkyl can partly or entirely be replaced by halogen atom, for example, haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl or trifluoromethyl.
Alkoxyl group: the straight or branched alkyl is connected on the structure through the Sauerstoffatom key.
Halogenated alkoxy: the straight or branched alkoxyl group, the Wasserstoffatoms on these alkoxyl groups can partly or entirely be replaced by halogen atom.For example, halogenated alkoxy such as chlorine methoxyl group, dichloro methoxyl group, trichlorine methoxyl group, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group or trifluoro ethoxy.
Thiazolinyl: straight or branched also can have two key, for example vinyl or allyl groups on any position.
Alkynyl: straight or branched also can have triple bond on any position, for example ethynyl or propargyl.
Aryl moiety in aryl and aralkyl, aromatic yl alkenyl, sweet-smelling alkynyl, aryloxy and the aryloxy alkyl comprises phenyl or naphthyl.
The indication heteroaryl is to contain one or more N, O, the heteroatomic 5 yuan of rings of S or 6 yuan of rings among the present invention.For example pyridine, furans, pyrimidine, pyrazine, pyridazine, triazine, quinoline or cumarone.
In compound of the present invention, because carbon-to-carbon double bond is connected different substituting groups and can forms steric isomer (representing different configurations with Z and E respectively) with the two keys of carbon-nitrogen.The present invention includes the mixture of Z type isomer and E-isomer and any ratio thereof.
Can the present invention be described with the compound of listing in the following table 1-table 5, but not limit the present invention.
I-I (R
4When not being selected from B-Z-Q or B-ZM)
Table 1
Table 2
| Numbering | R 2 | R 3 | X | Y | B | Z | R 8 | R 9 |
| 2-1 | Cl | Cl | O | NH | CH 2CH 2 | NH | Cl | Cl |
| 2-2 | Cl | Cl | O | NH | CH 2CH 2 | NH | Cl | Br |
| 2-3 | Cl | Cl | O | NH | CH 2CH 2 | NH | Cl | CF 3 |
| 2-4 | Cl | Br | O | NH | CH 2CH 2 | NH | Cl | Br |
| 2-5 | Cl | Br | O | NH | CH 2 | NH | Cl | Br |
| 2-6 | Cl | Br | O | NH | CH 2CH 2CH 2 | NH | Cl | Br |
| 2-7 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | Cl | Br |
| 2-8 | Cl | Br | O | NH | CH 2CH 2CH 2CH 2 | NH | Cl | Br |
| 2-9 | Cl | CF 3 | O | NH | CH 2CH 2 | NH | Cl | Br |
| 2-10 | Cl | CF 3 | O | NH | CH 2CH 2 | NH | Cl | CF 3 |
| 2-1l | Cl | CF 3 | O | NH | CH 2CH 2 | NH | CN | Cl |
| 2-12 | Cl | CF 3 | O | NH | CH 2CH 2 | NH | CN | Br |
| 2-13 | Cl | CF 3 | O | NH | CH 2CH 2 | NH | CN | CF 3 |
| 2-14 | CN | Cl | O | NH | CH 2CH 2 | NH | Cl | Cl |
| 2-15 | CN | Cl | O | NH | CH 2CH 2 | NH | Cl | Br |
| 2-16 | CN | Br | O | NH | CH 2CH 2 | NH | Cl | Cl |
| 2-17 | CN | Br | O | NH | CH 2CH 2 | NH | Cl | Br |
| 2-18 | CN | CF 3 | O | NH | CH 2CH 2 | NH | Cl | Cl |
| 2-19 | CN | CF 3 | O | NH | CH 2CH 2 | NH | Cl | Br |
| 2-20 | CN | CF 3 | O | NH | CH 2CH 2 | NH | CN | Cl |
| 2-21 | CN | CF 3 | O | NH | CH 2CH 2 | NH | CN | Br |
| 2-22 | CN | CF 3 | O | NH | CH 2CH 2 | NH | CN | CF 3 |
| 2-23 | Cl | Br | O | NH | CH 2CH 2CH 2 | NH | Cl | Cl |
| 2-24 | Cl | Br | O | NH | CH 2CH 2CH 2 | NH | Cl | Br |
| 2-25 | CN | Br | O | NH | CH 2CH 2CH 2 | NH | Cl | Br |
| 2-26 | CN | Br | O | NH | CH 2CH 2CH 2 | NH | Cl | CF 3 |
| 2-27 | Cl | Br | O | NH | CH 2CH 2CH 2CH 2 | NH | Cl | Cl |
| 2-28 | Cl | Br | O | NH | CH 2CH 2CH 2CH 2 | NH | Cl | Br |
| 2-29 | CN | Br | O | NH | CH 2CH 2CH 2CH 2 | NH | Cl | Br |
| 2-30 | CN | Br | O | NH | CH 2CH 2CH 2CH 2 | NH | Cl | CF 3 |
| 2-31 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | Cl | Cl |
| 2-32 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | Cl | Br |
| 2-33 | CN | Br | O | NH | CH(CH 3)CH 2 | NH | Cl | Br |
| 2-34 | CN | Br | O | NH | CH(CH 3)CH 2 | NH | Cl | CF 3 |
| 2-35 | Cl | Br | O | NH | CH(CH 3)CH(CH 3) | NH | Cl | Cl |
| 2-36 | Cl | Br | O | NH | CH(CH 3)CH(CH 3) | NH | Cl | Br |
| 2-37 | CN | Br | O | NH | CH(CH 3)CH(CH 3) | NH | Cl | Br |
| 2-38 | CN | Br | O | NH | CH(CH 3)CH(CH 3) | NH | Cl | CF 3 |
| 2-39 | Cl | Br | O | NH | CH(CH 3)CH 2CH 2 | NH | Cl | Cl |
| 2-40 | Cl | Br | O | NH | CH 2CH(CH 3)CH 2 | NH | Cl | Br |
| 2-41 | CN | Br | O | NH | CH(CH 3)CH 2CH 2 | NH | Cl | Br |
| 2-42 | CN | Br | O | NH | CH 2CH(CH 3)CH 2 | NH | Cl | CF 3 |
| 2-43 | Cl | Br | S | O | CH 2CH 2 | O | Cl | Cl |
| 2-44 | Cl | Br | S | O | CH 2CH 2 | O | Cl | Br |
| 2-45 | Cl | Br | S | O | CH 2CH 2CH 2 | O | Cl | Cl |
| 2-46 | Cl | Br | S | O | CH 2CH 2CH 2 | O | Cl | Br |
| 2-47 | Cl | Br | S | O | CH(CH 3)CH 2 | O | Cl | Br |
| 2-48 | CN | Br | S | O | CH(CH 3)CH 2 | O | Cl | Br |
| 2-49 | Cl | Br | S | NH | CH 2CH 2 | O | Cl | Cl |
| 2-50 | Cl | Br | O | NH | CH 2CH 2 | O | Cl | Br |
| 2-51 | Cl | Br | O | NH | CH 2CH 2CH 2 | O | Cl | Cl |
| 2-52 | Cl | Br | O | NH | CH 2CH 2CH 2 | O | Cl | Br |
| 2-53 | Cl | Br | O | NH | CH(CH 3)CH 2 | O | Cl | Br |
| 2-54 | CN | Br | O | NH | CH(CH 3)CH 2 | O | Cl | Br |
| 2-55 | Cl | Br | O | NH | CH 2CH 2 | S | Cl | Cl |
| 2-56 | Cl | Br | O | NH | CH 2CH 2 | S | Cl | Br |
| 2-57 | Cl | Br | O | NH | CH 2CH 2CH 2 | S | Cl | Cl |
| 2-58 | Cl | Br | O | NH | CH 2CH 2CH 2 | S | Cl | Br |
| 2-59 | Cl | Br | O | NH | CH(CH 3)CH 2 | S | Cl | Br |
| 2-60 | CN | Br | O | NH | CH(CH 3)CH 2 | S | Cl | Br |
| 2-61 | Cl | Br | O | O | CH 2CH 2 | O | Cl | Cl |
| 2-62 | Cl | Br | O | O | CH 2CH 2 | O | Cl | Br |
| 2-63 | Cl | Br | O | O | CH 2CH 2CH 2 | O | Cl | Cl |
| 2-64 | Cl | Br | O | O | CH 2CH 2CH 2 | O | Cl | Br |
| 2-65 | Cl | Br | O | S | CH(CH 3)CH 2 | O | Cl | Br |
| 2-66 | CN | Br | O | S | CH(CH 3)CH 2 | O | Cl | Br |
Table 3
| Numbering | R 2 | R 3 | X | Y | B | Z | R 10 | R 11 |
| 3-1 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SCF 3 |
| 3-2 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SCH 2F |
| 3-3 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SOCF 3 |
| 3-4 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SOCH 2F |
| 3-5 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SOCHF 2 |
| 3-6 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SOC 2H 5 |
| 3-7 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SO 2CF 3 |
| 3-8 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SO 2CH 2F |
| 3-9 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SO 2CHF 2 |
| 3-10 | Cl | Br | O | NH | CH 2CH 2 | NH | CN | SOC 2H 5 |
| 3-11 | Cl | Br | O | NH | CH 2CH 2 | NH | COCH 3 | SOCF 3 |
| 3-12 | Cl | Br | O | NH | CH 2CH 2 | NH | COCH 3 | SOCH 2F |
| 3-13 | Cl | Br | O | NH | CH 2CH 2 | NH | COCH 3 | SOCHF 2 |
| 3-14 | Cl | Br | O | NH | CH 2CH 2 | NT 1 | CN | SOCF 3 |
| 3-15 | Cl | Br | O | NH | CH 2CH 2 | NT 1 | CN | SOCH 2F |
| 3-16 | Cl | Br | O | NH | CH 2CH 2 | NT 1 | CN | SOCHF 2 |
| 3-17 | Cl | Br | O | NH | CH 2CH 2 | NT 2 | CN | SOCF 3 |
| 3-18 | Cl | Br | O | NH | CH 2CH 2 | NT 2 | CN | SOC 2H 5 |
| 3-19 | Cl | Br | O | NH | CH 2CH 2 | NT 2 | CN | SOCH 2F |
| 3-20 | Cl | Br | O | NH | CH 2CH 2 | NT 3 | CN | SOC 2H 5 |
| 3-21 | Cl | Br | O | NH | CH 2CH 2 | NT 3 | CN | SOCF 3 |
| 3-22 | Cl | Br | O | NH | CH 2CH 2 | NT 3 | CN | SOCH 2F |
| 3-23 | Cl | Br | O | NH | NHCH 2 | NH | CN | SOCF 3 |
| 3-24 | Cl | Br | O | NH | NHCH 2CH 2 | NH | CN | SOCF 3 |
| 3-25 | Cl | Br | O | NH | OCH 2 | NH | CN | SOCF 3 |
| 3-26 | Cl | Br | O | NH | OCH 2CH 2 | NH | CN | SOCF 3 |
| 3-27 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SCF 3 |
| 3-28 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SCH 2F |
| 3-29 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SOCF 3 |
| 3-30 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SOCH 2F |
| 3-31 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SOCHF 2 |
| 3-32 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SOC 2H 5 |
| 3-33 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SO 2CF 3 |
| 3-34 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SO 2CH 2F |
| 3-35 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SO 2CHF 2 |
| 3-36 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SOC 2H 5 |
| 3-37 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | COCH 3 | SOCF 3 |
| 3-38 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | COCH 3 | SOCH 2F |
| 3-39 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | COCH 3 | SOCHF 2 |
| 3-40 | Cl | Br | O | NH | CH(CH 3)CH 2 | NT 1 | CN | SOCF 3 |
| 3-41 | Cl | Br | O | NH | CH(CH 3)CH 2 | NT 1 | CN | SOCH 2F |
| 3-42 | Cl | Br | O | NH | CH(CH 3)CH 2 | NT 1 | CN | SOCHF 2 |
| 3-43 | Cl | Br | O | NH | CH(CH 3)CH 2 | NT 2 | CN | SOCF 3 |
| 3-44 | Cl | Br | O | NH | CH(CH 3)CH 2 | NT 2 | CN | SOC 2H 5 |
| 3-45 | Cl | Br | O | NH | CH(CH 3)CH 2 | NT 2 | CN | SOCH 2F |
| 3-46 | Cl | Br | O | NH | CH(CH 3)CH 2 | NT 3 | CN | SOC 2H 5 |
| 3-47 | Cl | Br | O | NH | CH(CH 3)CH 2 | NT 3 | CN | SOCF 3 |
| 3-48 | Cl | Br | O | NH | CH(CH 3)CH 2 | NT 3 | CN | SOCH 2F |
| 3-49 | Cl | Br | O | NH | CH 2 | NH | CN | SCF 3 |
| 3-50 | Cl | Br | O | NH | CH 2 | NH | CN | SCH 2F |
| 3-51 | Cl | Br | O | NH | CH 2 | NH | CN | SOCF 3 |
| 3-52 | Cl | Br | O | NH | CH 2CH 2CH 2 | NH | CN | SCF 3 |
| 3-53 | Cl | Br | O | NH | CH 2CH 2CH 2 | NH | CN | SCH 2F |
| 3-54 | Cl | Br | O | NH | CH 2CH 2CH 2CH 2 | NT 2 | CN | SOCHF 2 |
| 3-55 | Cl | Br | O | NH | CH 2CH 2CH 2CH 2 | NT 2 | CN | SOC 2H 5 |
| 3-56 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH | COCH 3 | SCF 3 |
| 3-57 | Cl | Br | O | NH | CH(CH 3)CH(CH 3) | NH | CN | SOCHF 2 |
| 3-58 | Cl | Br | O | NH | CH(CH 3)CH(CH 3) | NT 1 | CN | SOC 2H 5 |
| 3-59 | Cl | Br | O | NH | CH(CH 3)CH 2CH 2 | NH | CN | SCF 3 |
| 3-60 | Cl | Br | O | NH | CH 2CH(CH 3)CH 2 | NH | CN | SOCF 3 |
| 3-61 | Cl | Br | S | NH | CH(CH 3)CH 2 | NH | CN | SCF 3 |
| 3-62 | Cl | Br | S | NH | CH(CH 3)CH 2 | NH | CN | SCH 2F |
| 3-63 | Cl | Br | S | NH | CH(CH 3)CH 2 | NH | CN | SOCF 3 |
| 3-64 | Cl | Br | S | NH | CH(CH 3)CH 2 | NH | CN | SOCH 2F |
| 3-65 | Cl | Br | S | NH | CH(CH 3)CH 2 | NH | CN | SOCHF 2 |
| 3-66 | Cl | Br | S | NH | CH(CH 3)CH 2 | NH | CN | SOC 2H 5 |
| 3-67 | Cl | Br | S | NH | CH(CH 3)CH 2 | NH | CN | SO 2CF 3 |
| 3-68 | Cl | Br | S | NH | CH(CH 3)CH 2 | NH | CN | SO 2CH 2F |
| 3-69 | Cl | Br | O | O | CH(CH 3)CH 2 | NH | CN | SCF 3 |
| 3-70 | Cl | Br | O | O | CH(CH 3)CH 2 | NH | CN | SCH 2F |
| 3-71 | Cl | Br | O | O | CH(CH 3)CH 2 | NH | CN | SOCF 3 |
| 3-72 | Cl | Br | O | O | CH(CH 3)CH 2 | NH | CN | SOCH 2F |
| 3-73 | Cl | Br | O | O | CH(CH 3)CH 2 | NH | CN | SOCHF 2 |
| 3-74 | Cl | Br | O | O | CH(CH 3)CH 2 | NH | CN | SOC 2H 5 |
| 3-75 | Cl | Br | O | O | CH(CH 3)CH 2 | NH | CN | SO 2CF 3 |
| 3-76 | Cl | Br | O | O | CH(CH 3)CH 2 | NH | CN | SO 2CH 2F |
| 3-77 | Cl | Cl | O | NH | CH 2CH 2 | NH | CN | SOCF 3 |
| 3-78 | Cl | Cl | O | NH | CH 2CH 2 | NH | CN | SOCH 2F |
| 3-79 | Cl | Cl | O | NH | CH 2CH 2 | NH | CN | SOCHF 2 |
| 3-80 | Cl | Cl | O | NH | CH(CH 3)CH 2 | NH | CN | SOCH 2F |
| 3-81 | Cl | Cl | O | NH | CH(CH 3)CH 2 | NH | CN | SOCHF 2 |
| 3-82 | Cl | CF 3 | O | NH | CH 2CH 2 | NH | CN | SOCF 3 |
| 3-83 | Cl | CF 3 | O | NH | CH 2CH 2 | NH | CN | SOCH 2F |
| 3-84 | Cl | CF 3 | O | NH | CH(CH 3)CH 2 | NH | CN | SOC 2H 5 |
| 3-85 | Cl | CF 3 | O | NH | CH(CH 3)CH 2 | NH | CN | SO 2CF 3 |
| 3-86 | Cl | CF 3 | O | NH | CH 2CH 2 | NT1 | CN | SOCF 3 |
| 3-87 | Cl | CF 3 | O | NH | CH 2CH 2 | NT 2 | CN | SOCF 3 |
| 3-88 | Cl | CF 3 | O | NH | CH 2CH 2 | NT 3 | CN | SOCF 3 |
| 3-89 | CN | Cl | O | NH | CH 2CH 2 | NH | CN | SOCF 3 |
| 3-90 | CN | Cl | S | NH | CH 2CH 2 | NH | CN | SOCH 2F |
| 3-91 | CN | Cl | S | NH | CH 2CH 2 | NH | CN | SOC 2H 5 |
| 3-92 | CN | Cl | O | NH | CH 2CH 2 | NT 1 | CN | SOCH 2F |
| 3-93 | CN | Cl | O | NH | CH 2CH 2 | NT 2 | CN | SOCH 2F |
| 3-94 | CN | Cl | O | NH | CH 2CH 2 | NT 3 | CN | SOCH 2F |
| 3-95 | CN | Cl | O | NH | CH 2CH 2 | NH | COCH 3 | SOCF 3 |
| 3-96 | CN | Cl | O | NH | CH(CH 3)CH 2 | NH | COCH 3 | SOCF 3 |
| 3-97 | CN | Cl | O | NH | CH(CH 3)CH 2 | NH | COCH 3 | SOCF 3 |
| 3-98 | CN | Cl | O | NH | CH 2CH 2 | NT 1 | COCH 3 | SOCF 3 |
| 3-99 | CN | Cl | O | NH | CH 2CH 2 | NT 2 | COCH 3 | SOCF 3 |
| 3-100 | CN | Cl | O | NH | CH 2CH 2 | NT 3 | COCH 3 | SOCF 3 |
| 3-101 | CN | Br | O | NH | CH 2CH 2 | NH | CN | SCF 3 |
| 3-102 | CN | Br | O | NH | CH 2CH 2 | NH | CN | SOCF 3 |
| 3-103 | CN | Br | O | NH | CH 2CH 2 | NH | CN | SOCH 2F |
| 3-104 | CN | CF 3 | O | NH | CH 2CH 2 | NT 1 | CN | SCF 3 |
| 3-105 | CN | CF 3 | O | NH | CH 2CH 2 | NT 2 | CN | SOCF 3 |
| 3-106 | CN | CF 3 | O | NH | CH 2CH 2 | NT 3 | CN | SOCH 2F |
| 3-107 | CN | CF 3 | O | NH | CH 2CH 2 | NH | CN | SOC 2H 5 |
| 3-108 | CN | CF 3 | O | NH | CH 2CH 2 | NH | CN | SOCH 2F |
| 3-109 | CN | CF 3 | O | NH | CH 2CH 2 | NH | CN | SOC 2H 5 |
| 3-110 | CN | Br | O | NH | CH 2CH 2CH 2 | NH | CN | SOCF 3 |
| 3-111 | CN | Br | O | NH | CH 2CH 2CH 2 | NH | CN | SOCH 2F |
| 3-112 | CN | Br | O | NH | CH 2CH 2CH 2CH 2 | NH | CN | SO 2CF 3 |
| 3-113 | CN | Br | O | NH | CH 2CH 2CH 2CH 2 | NH | CN | SO 2C 2H 5 |
| 3-114 | CN | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SOCF 3 |
| 3-115 | CN | Br | O | NH | CH(CH 3)CH 2 | NH | CN | SOCH 2F |
| 3-116 | CN | Br | O | NH | CH(CH 3)CH(CH 3) | NH | CN | SO 2CF 3 |
| 3-117 | CN | Br | O | NH | CH(CH 3)CH(CH 3) | NH | CN | SO 2C 2H 5 |
| 3-118 | CN | Br | O | NH | CH(CH 3)CH 2CH 2 | NH | CN | SO 2CF 3 |
| 3-119 | CN | Br | O | NH | CH 2CH(CH 3)CH 2 | NT 3 | CN | SO 2C 2H 5 |
| 3-120 | Cl | Br | O | NH | CH(CH 3) | NH | CN | SOCF 3 |
| 3-121 | Cl | Br | O | NH | CH 2CO | NH | CN | SOCF 3 |
| 3-122 | Cl | Br | O | NH | CH(CH 3)CO | NH | CN | SOCF 3 |
| 3-123 | Cl | Br | O | NH | CH 2CH 2CO | NH | CN | SOCF 3 |
| 3-124 | Cl | Br | O | NH | CH 2CH 2OCH 2 | NH | CN | SOCF 3 |
| 3-125 | Cl | Br | O | NH | CH 2CH 2OCH 2CH 2 | NH | CN | SOCF 3 |
| 3-126 | Cl | Br | O | NH | CH 2CH 2NHCH 2CH 2 | NH | CN | SOCF 3 |
| 3-127 | Cl | Br | O | NH | CH 2CH 2OCH 2CO | NH | CN | SOCF 3 |
| 3-128 | Cl | Br | O | NH | CH 2CH 2NHCH 2CO | NH | CN | SOCF 3 |
T in the table 3
1Representative
T
2Representative
T
3Representative
Table 4
Table 5
| Numbering | R 2 | R 3 | X | Y | B | Z | M |
| 5-1 | Cl | Cl | O | NH | CH 2CH 2 | NH 2 | HCl |
| 5-2 | Cl | Cl | O | NH | CH 2CH 2 | NH 2 | Hydrocerol A |
| 5-3 | Cl | Cl | O | NH | CH 2CH 2 | NH 2 | The DL-oxysuccinic acid |
| 5-4 | Cl | Cl | O | NH | CH 2CH 2 | NH 2 | CH 3CO 2H |
| 5-5 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | HCl |
| 5-6 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | Hydrocerol A |
| 5-7 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | The DL-oxysuccinic acid |
| 5-8 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | Tartrate |
| 5-9 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | Toxilic acid |
| 5-10 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | Phenylsulfonic acid |
| 5-11 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | Whitfield's ointment |
| 5-12 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | Phenylformic acid |
| 5-13 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | CF 3CO 2H |
| 5-14 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | CH 3CO 2H |
| 5-15 | CN | Br | O | NH | CH 2CH 2 | NH 2 | HCl |
| 5-16 | CN | Br | O | NH | CH 2CH 2 | NH 2 | Hydrocerol A |
| 5-17 | CN | Br | O | NH | CH 2CH 2 | NH 2 | The DL-oxysuccinic acid |
| 5-18 | CN | Br | O | NH | CH 2CH 2 | NH 2 | CH 3CO 2H |
| 5-19 | Cl | Br | O | NH | CH 2CH 2 | N(C 2H 5) 2 | HCl |
| 5-20 | Cl | Br | O | NH | CH 2CH 2 | N(C 2H 5) 2 | Hydrocerol A |
| 5-21 | Cl | Br | O | NH | CH 2CH 2 | N(C 2H 5) 2 | The DL-oxysuccinic acid |
| 5-22 | Cl | Br | O | NH | CH 2CH 2 | N(C 2H 5) 2 | CH 3CO 2H |
| 5-23 | Cl | Br | O | NH | CH 2 | NH 2 | HCl |
| 5-24 | Cl | Br | O | NH | CH 2 | NH 2 | Hydrocerol A |
| 5-25 | Cl | Br | O | NH | CH 2CH 2CH 2 | NH 2 | HCl |
| 5-26 | Cl | Br | O | NH | CH 2CH 2CH 2 | NH 2 | Hydrocerol A |
| 5-27 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH 2 | HCl |
| 5-28 | Cl | Br | O | NH | CH(CH 3)CH 2 | NH 2 | Hydrocerol A |
| 5-29 | Cl | Br | O | NH | CH(CH 3)CH 2CH 2 | NH 2 | HCl |
| 5-30 | Cl | Br | O | NH | CH(CH 3)CH 2CH 2 | NH 2 | Hydrocerol A |
| 5-31 | Cl | Br | O | NH | CH(CH 3)CH(CH 3) | NH 2 | HCl |
| 5-32 | Cl | Br | O | NH | CH(CH 3)CH(CH 3) | NH 2 | Hydrocerol A |
| 5-33 | Cl | Br | O | NH | CH(CH 3)CH 2CH 2 | N(C 2H 5) 2 | HCl |
| 5-34 | Cl | Br | O | NH | CH(CH 3)CH 2CH 2 | N(C 2H 5) 2 | Hydrocerol A |
| 5-35 | Cl | Br | O | NH | CH(CH 3)CH 2CH 2 | N(C 2H 5) 2 | Tartrate |
| 5-36 | Cl | Br | O | NH | CH(CH 3)CH 2CH 2 | N(C 2H 5) 2 | Toxilic acid |
| 5-37 | Cl | Br | O | NH | CH(CH 3)CH(CH 3) | N(CH 3) 2 | HCl |
| 5-38 | Cl | Br | O | NH | CH(CH 3)CH(CH 3) | N(CH 3) 2 | Hydrocerol A |
| 5-39 | Cl | Br | S | NH | CH 2CH 2 | NH 2 | CH 3CO 2H |
| 5-40 | Cl | Br | S | NH | CH 2CH 2 | NH 2 | HCl |
| 5-41 | Cl | Br | O | O | CH 2CH 2 | NH 2 | HCl |
| 5-42 | Cl | Br | O | O | CH 2CH 2 | NH 2 | CH 3CO 2H |
| 5-43 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | CH 3SO 3H |
| 5-44 | Cl | Cl | O | NH | CH 2CH 2 | NH 2 | Phenylsulfonic acid |
| 5-45 | Cl | Br | O | NH | CH 2CH 2 | NH 2 | Tosic acid |
Compound of Formula I of the present invention can prepare according to following method:
General formula I-I compound (is R in the compound of Formula I
4Do not comprise when being selected from B-Z-Q or B-ZM) can make by the oxazinone compounds shown in the general formula I I and substituted amine, alcohol or thiol reactant:
General formula I-II compound (is R
4During=B-Z-Q), can (Z be NH in the formula by I-I '
2, OH or SH) react under the triethylamine effect with acyl chlorides Q and to make:
General formula I-III compound (is R
4During=B-ZM), can (Z be NH by I-I '
2, N (CH
3)
2Or N (C
2H
5)
2) make with the M reaction:
The definition of each group is the same in the general formula.
Be reflected in the solvent and carry out, suitable is selected from like acetonitrile, THF, ether, methylene dichloride, chloroform, toluene etc.
Temperature of reaction is generally 20～100 ℃ between room temperature to solvent boiling point temperature.
Reaction times is 30 minutes to 20 hours, common 1～10 hour.
The midbody that the present invention relates to is following:
General formula I I is the oxazinone compounds, and relevant summary is seen Biorganic and Medicinal Chemistry 2000,8; 2095-2103. with J.Heterocyclic Chemistry 1999; 36,563-588, its preparation method is with reference to WO03015519, WO2005118552 method.
Adjacent amido benzoic acid derivative shown in the general formula III can be made through two steps by arylamine, with reference to following document: OrganicSyntheses, Coll.Vol.10, p.23 (2004); Vol.79, p.196 (2002); Adv.Heterocycl.Chem.1975,18,1-58; Journal of the Brazilian Chemical Society 2001,12 (3), 273-324; Angew.Chem.Int.Ed.Engl.1980,19,222-223.
The preparation method of the carboxylic acid cpd shown in the general formula I V is with reference to WO2006062978, WO03015519.
Compound of Formula I of the present invention all demonstrates high insecticidal activity to adult, larva and the ovum of harmful insect in agriculture, civilian and the animal technical field.Part of compounds shows fungicidal activity preferably.Therefore, the present invention comprises that also compound of Formula I is used as the application of sterilant and/or sterilant in agricultural and other field.
Especially, compound of Formula I has activity to following section and the important kind of purpose: lepidopteran (greedy Noctua, Heliothis, straw borer spp, Pericarpium Mali pumilae steinernema etc.).For example very effectively to European corn borer, sugarcane borer, codling moth, codling moth, gypsymoth etc., particularly active better to small cabbage moth, under very low dosage, just can obtain good effect.Simultaneously, part of compounds of the present invention also has excellent bactericidal activity, can be used for preventing and treating rice blast, cucumber downy mildew, anthrax.
Simultaneously, compound of Formula I has hypotoxicity to many useful insects and acarid, Mammals, fish, bird, and does not have phytotoxicity.
Because its positive characteristic, above-claimed cpd can be advantageously used in protection agricultural and important crop, domestic animal and the kind poultry of horticulture, and the human environment that often goes avoids the injury of harmful insect and fungi.
For obtaining ideal effect, the consumption of compound changes because of various factors, for example the formulation of the type of the crop of compound used therefor, protection in advance, harmful organism, gradient of infection, weather condition, application method, employing.
The compound dosage that per hectare 10 grams are-5 kilograms can provide sufficient control.
Another object of the present invention also relates to through using compound of Formula I, the insect in crop that control agricultural and horticulture are important and/or domestic animal and kind poultry and/or the human environment that often goes and/or the method for plant pathogenic fungi.Especially, the consumption of compound changes in per hectare 10 restrains-5 kilograms.
In order to be applied to agricultural, use the compsn that contains one or more compound of Formula I normally useful.
Therefore, another object of the present invention relates to and contains desinsection and/or the fungicidal compsn of one or more compound of Formula I as activeconstituents.
The type of service of compsn can be dry powder, wettable powder, missible oil, microemulsion, paste, granule, solution, suspension agent etc.: concrete application is depended in the selection of types of compositions.
Compsn is for example chosen wantonly in the presence of tensio-active agent with the currently known methods preparation, through diluting or the lytic activity material with solvent medium and/or solid diluent.
Available solid diluent or carrier for example are: silicon-dioxide, kaolin, wilkinite, talcum, zeyssatite, rhombspar, lime carbonate, Natural manganese dioxide, chalk, clay, synthetic silicate, attapulgite, sepiolite etc.
Beyond dewatering; The available liquid diluent also comprises like aromatics organic solvent (mixture of YLENE or korenyl, chlorobenzene etc.), paraffin (petroleum fractions), alcohols (methyl alcohol, propyl alcohol, butanols, octanol, glycerine); Ester class (ETHYLE ACETATE, isobutyl acetate etc.); Ketone (pimelinketone, acetone, methyl phenyl ketone, isophorone, ethyl pentyl group ketone etc.), amides (N, dinethylformamide, N-Methyl pyrrolidone etc.).
The available tensio-active agent is sodium, calcium, triethylamine or the triethanolamine salt of polyoxyethylene ester, sulfonated lignin of AS, alkylaryl sulphonate, polyoxyethylene alkylphenol, sorbyl alcohol etc.
Compsn also can contain special additive and be used for specific purpose, for example contains tackiness agent such as gum arabic, Z 150PH, Vinylpyrrolidone polymer etc.
The concentration of activeconstituents can be according to the preparation type of activeconstituents, application target, envrionment conditions and employing and in wide region, change in the above-mentioned compsn.Usually, the concentration range of activeconstituents is 1-90%, preferred 5-60%.
If desired, can in compsn, add can be compatible with compound of Formula I other activeconstituentss, for example other miticide/sterilants, mycocide, plant-growth regulator, microbiotic, weedicide, fertilizer.
The compound method of several kinds of formulations is exemplified below:
The preparation of suspension agent: active component content is 5%-35% in the common prescription.With water is medium, and former medicine, dispersion agent, suspending agent and antifreezing agent etc. are added in the sand mill, grinds, and processes suspension agent.
The preparation of aqueous emulsion: former medicine, solvent added with emulsifying agent be in the same place, make and be dissolved into even oil phase.Water, antifreezing agent etc. is mixed, becomes the homogeneous water.Under high-speed stirring, water is joined oil phase or oil phase is joined water, form the aqueous emulsion of good dispersibility.Aqueous emulsion active component content of the present invention is generally 5%-15%.Be the preparation emulsifiable concentrate, compound of the present invention is dissolvable in water a kind of or several mixed solvents, adds emulsifying agent again and strengthens the dispersion effect of compound in water.
The preparation of wettable powder:,, after ultrafine crusher is pulverized, promptly obtain the wettable powder product of predetermined content (for example 10%-40%) with thorough mixing such as former medicine, various tensio-active agent and solid diluents by the prescription requirement.For preparation is suitable for spraying the wettable powder of usefulness, compound of the present invention can with pressed powder such as clay, inorganic silicate, carbonate and wetting agent, tackiness agent and/or the dispersion agent composition mixture of porphyrize.
The preparation of water-dispersible granules: former medicine and powdery solid thinner, wetting spreader-sticker and tackiness agent etc. are mixed pulverizing; After adding the water kneading again; Add in the tablets press that the certain specification screen cloth is housed and carry out granulation, and then through dry, screening (pressing the screen cloth scope).Also can former medicine, dispersion agent, disintegrating agent and wetting agent and solid diluent be added in the sand mill, be medium milling with water, processes suspension agent, carries out spray drying granulation then, and formulation content is the 20%-30% granular product usually.
Embodiment
Following specific embodiment is used for further specifying the present invention, but the present invention is limited to these examples absolutely not.
Synthetic embodiment
Instance 1: the preparation of compound 1-12
Get 0.23 gram sodium hydride in 100 milliliters of reaction flasks, petroleum ether twice adds 40 milliliters of THFs, stirs to add NH down
2CN, reaction is not emitted to there being bubble, is warming up to 35 ℃ of reactions 10 minutes again, adds 0.5 gram II-I (WO03015519 is seen in preparation), stirring reaction 3 hours.After the TLC monitoring reaction finishes, behind the decompression precipitation, in reaction flask, pour 50 milliliters of saturated aqueous common salts into, divide with 60 milliliters of ETHYLE ACETATE to extract for three times, drying, precipitation, column chromatography get product 0.45 gram, i.e. compound 1-12.Yield 82.4%.
Instance 2: the preparation of compound 1-99
Get 0.5 gram II-I in 50 milliliters of reaction flasks, add 25 milliliters of acetonitriles, stir the 0.3 gram NH of adding down
2C (CH
3)=CHCN, temperature rising reflux reaction 8 hours.After the TLC monitoring reaction finishes, behind the decompression precipitation, in reaction flask, pour in 50 milliliters of saturated aqueous common salts, divide with 60 milliliters of ETHYLE ACETATE to extract for three times, drying, precipitation, column chromatography get product 0.39 gram, i.e. compound 1-99.Yield 66.1%.
Instance 3: the preparation of compound 2-4
Get 0.5 gram II-I in 50 milliliters of reaction flasks, add 25 milliliters of acetonitriles, stir the 0.03 gram quadrol of adding down, temperature rising reflux reaction 15 hours.After the TLC monitoring reaction finishes, behind the decompression precipitation, in reaction flask, pour in 50 milliliters of saturated aqueous common salts, divide with 60 milliliters of ETHYLE ACETATE to extract for three times, drying, precipitation, column chromatography get product 0.19 gram, i.e. compound 2-4.Yield 39.6%.
Other compounds of general formula I can make with preparation method provided by the invention.
The nuclear magnetic data of part of compounds (
1HNMR, 300MHz, interior mark TMS, solvent C DCl
3) as follows:
Compound 1-12: fusing point 118-120 ℃.δppm?2.08(3H，s)，7.34(1H，s)，7.37(1H，s)，7.63(1H，q)，7.70(1H，s)，8.02(1H，s)，8.19(1H，m)，8.52(1H，m)，11.71(1H，s)。
Compound 1-93: fusing point 178-179 ℃.δppm?0.91(3H，t)，1.12(3H，d)，1.46(2H，m)，2.13(3H，s)，3.98(1H，q)，6.02(1H，d)，7.12(1H，s)，7.14(1H，d)，7.31(1H，m)，7.36(1H，m)，7.82(1H，m)，8.44(1H，m)，10.24(1H，s)。
Compound 1-94: fusing point 182-183 ℃.δppm?0.93(3H，t)，1.13(3H，d)，1.46(2H，m)，2.15(3H，s)，3.97(1H，q)，6.03(1H，d)，7.12(1H，s)，7.16(1H，d)，7.32(1H，m)，7.38(1H，m)，7.84(1H，m)，8.43(1H，m)，10.26(1H，s)。
Compound 1-96: fusing point 213-215 ℃.δppm?2.16(3H，s)，2.18(3H，s)，5.18(1H，s)，7.39(1H，s)，7.53(1H，s)，7.61(1H，q)，7.79(1H，s)，8.02(1H，s)，8.17(1H，m)，8.51(1H，m)，9.90(1H，s)。
Compound 1-115: fusing point 234-235 ℃.δppm?1.28(3H，t)，2.21(3H，s)，2.28(3H，s)，4.15(2H，q)，4.53(1H，s)，7.03(1H，s)，7.35(1H，s)，7.39(1H，m)，7.56(1H，s)，7.83(1H，m)，7.93(1H，s)，8.37(1H，m)，10.01(1H，s)。
Compound 1-132: fusing point 120-121 ℃.δppm?2.13(3H，s)，3.97(2H，m)，6.75(1H，s)，7.03(1H，s)，7.18(1H，s)，7.22(1H，s)，7.37(1H，q)，7.85(1H，m)，7.56(1H，m)，8.44(1H，m)，9.66(1H，s)。
Compound 1-135: fusing point 131-132 ℃.δppm?2.18(3H，s)，3.97(2H，m)，6.75(1H，s)，7.03(1H，s)，7.18(1H，s)，7.22(1H，s)，7.37(1H，q)，7.85(1H，m)，7.56(1H，m)，8.44(1H，m)，9.66(1H，s)。
Compound 1-138: fusing point 176-177 ℃.δppm?2.16(3H，s)，2.82(2H，t)，3.60(2H，t)，3.86(3H，s)，3.87(3H，s)，6.14(1H，s)，6.74(3H，m)，7.10(2H，m)，7.23(1H，s)，7.37(1H，m)，7.83(1H，m)，7.56(1H，m)，8.44(1H，m)，10.10(1H，s)。
Compound 1-167: fusing point 153-154 ℃.δppm?2.18(3H，s)，3.79(3H，s)，4.16(2H，d)，6.65(1H，s)，7.04(1H，d)，7.38(3H，m)，7.85(1H，m)，8.44(1H，m)，9.91(1H，s)。
Compound 1-181: fusing point 111-112 ℃.δppm?1.23(2H，t)，2.15(3H，s)，2.88(2H，s)，3.43(2H，s)，7.18(2H，s)，7.32(1H，s)，7.36(2H，m)，7.82(1H，m)，8.42(1H，m)。
Compound 1-184: fusing point 128-129 ℃.δppm?1.03(6H，t)，1.25(2H，s)，2.18(3H，s)，2.57(4H，q)，2.63(2H，m)，3.42(2H，d)，6.95(1H，s)，7.09(1H，d)，7.23(1H，s)，7.36(2H，m)，7.82(1H，m)，8.45(1H，m)，10.37(1H，s)。
Compound 1-220: fusing point 138-139 ℃.δppm?2.16(3H，s)，3.19(2H，t)，3.39(2H，t)，4.01(1H，d)，7.38(1H，s)，7.40(2H，d)，7.60(1H，m)，8.16(1H，m)，8.50(1H，m)。
Compound 1-230: fusing point 170-171 ℃.δppm?1.171(1H，t)，2.17(3H，s)，2.50(2H，m)，3.26(2H，m)，7.37(1H，s)，7.39(1H，s)，7.49(1H，d)，7.61(1H，m)，8.16(1H，m)，8.49(1H，m)。
Compound 1-414: fusing point 229-230 ℃.δppm?2.05(3H，s)，3.38(4H，m)，3.66(4H，m)，6.89(1H，s)，7.02(1H，s)，7.30(1H，s)，7.38(1H，m)，7.85(1H，m)，8.46(1H，m)，10.19(1H，s)。
Compound 1-421: fusing point 137-138 ℃.δppm?1.27(3H，t)，1.72(4H，m)，1.99(3H，s)，2.45(4H，m)，4.40(1H，m)，4.16(2H，q)，6.91(1H，s)，7.01(1H，s)，7.36(2H，m)，7.83(1H，m)，8.43(1H，m)，10.12(1H，s)。
Compound 1-423: fusing point 137-138 ℃.δppm?1.21(3H，t)，1.43(4H，m)，2.09(2H，m)，2.16(3H，s)，3.14(2H，m)，4.02(2H，q)，4.25(1H，m)，7.31(3H，m)，7.63(1H，m)，8.18(1H，m)，8.49(1H，m)，10.28(1H，s)。
Compound 1-425: fusing point 216-217 ℃.δppm?1.82(2H，m)，2.16(3H，s)，3.08(2H，m)，3.92(2H，m)，5.88(2H，m)，7.22(1H，s)，7.37(1H，s)，7.42(1H，s)，7.63(1H，m)，8.17(1H，m)，8.47(1H，m)。
Compound 2-4: fusing point 258-259 ℃.δppm?2.17(6H，s)，3.21(4H，s)，7.39(2H，m)，7.48(2H，s)，7.56(2H，m)，8.13(2H，m)，8.42(2H，s)，8.46(2H，m)，10.22(2H，s)。
FORMULATION EXAMPLE (each component add-on is weight percentage).
Embodiment 4:30% compound 1-12 wettable powder
Compound 1-12 30%
Sodium lauryl sulphate 2%
Sodium lignosulfonate 3%
Naphthalene sulfonic acidformaldehyde condensation product 5%
Light calcium carbonate complements to 100%
With thorough mixing such as compound 1-12, various tensio-active agent and solid diluents, after ultrafine crusher is pulverized, promptly obtain 30% wettable powder product.
Embodiment 5:20% compound 1-96 suspension agent
Compound 1-96 20%
Condensation compound of methyl naphthalene sulfonic acid and formaldehyde 3%
The newborn 0201B 2% of farming
Nongru-700
#1%
XG 550 0.2%
Terepthaloyl moietie 5%
Water complements to 100%
With water is medium, and compound 1-96, dispersion agent, suspending agent and antifreezing agent etc. are added in the sand mill, grinds, and processes suspension agent.
Embodiment 6:60% compound 1-115 water-dispersible granules
Compound 1-115 60%
Naphthalenesulfonic acid-formaldehyde condensate 12%
N-methyl-oleoyl-Sodium taurine salt 8%
Vinylpyrrolidone polymer 2%
CMC 99.5 2%
Kaolin complements to 100%
Compound 1-115 and powdery solid thinner, wetting spreader-sticker and tackiness agent etc. are mixed pulverizing, after adding water again and mediating, add in the tablets press of 10-100 eye mesh screen and carry out granulation, and then through dry, screening (pressing the screen cloth scope).
Embodiment 7:10% compound 2-4 aqueous emulsion
Compound 2-4 10%
T 46155 (n
20) styroyl
Phenolic group oleic acid ester 8%
Calcium dodecylbenzene sulphonate 16%
Piperonyl butoxide 15%
Pimelinketone 10%
Sorbyl alcohol 5%
Water complements to 100%
Compound 2-4, solvent added with emulsifying agent be in the same place, make and be dissolved into even oil phase.Water, antifreezing agent etc. is mixed, becomes the homogeneous water.Under high-speed stirring, water is joined oil phase or oil phase is joined water, form the aqueous emulsion of good dispersibility.
Embodiment 8:25% compound 1-12 suspension agent
Compound 1-12 25%
The newborn 0201B 2.5% of farming
Farming breast 1,601 1%
Naphthalene sulfonic acidformaldehyde condensation product 2%
White carbon black 0.1%
Terepthaloyl moietie 5%
Water complements to 100%
With water is medium, and compound 1-12, dispersion agent, suspending agent and antifreezing agent etc. are added in the sand mill, grinds, and processes suspension agent.
Embodiment 9:20% compound 2-4 wettable powder
Compound 2-4 20%
Methanonaphthalene sodium sulfonate 6%
Naphthalene sulfonic acidformaldehyde condensation product 3%
Sodium lauryl sulphate 2%
White carbon black 5%
Farming breast 600
#0.5%
Light calcium carbonate complements to 100%
With thorough mixing such as compound 2-4, various tensio-active agent and solid diluents, after ultrafine crusher is pulverized, promptly obtain 20% wettable powder product.
Biological activity determination
Instance 10 fungicidal activities are measured
With The compounds of this invention the various fungus diseases of plant are tested.The method of test is following:
Adopt the potted plant measuring method of live body.The former medicinal small amount of acetone dissolving of testing compound is diluted to required concentration with the water that contains 0.1% tween 80.Spray pesticide carries out the disease inoculation after 24 hours to plant examination material.After the inoculation, plant is placed in the fixed temperature and humidity incubator, makes to infect and continue, wait to contrast abundant morbidity back (being generally week age) and carry out assessment surveys.
The partial test result is following:
When liquor strength is 25ppm; Compound 1-12,1-96,1-115,1-181,1-184,1-230,1-421,1-423,1-425 etc. reach more than 50% the preventive effect of rice blast; When liquor strength is 400ppm; Compound 1-93,1-94 etc. reach 98% to the cucumber downy mildew preventive effect, and the anthrax preventive effect is reached 90%.
Instance 11 pesticide and miticide actilities are measured
With The compounds of this invention several kinds of insects and mite class have been carried out the insecticidal activity assay test.Method for measuring is following:
After the mixed solvent dissolving of testing compound with acetone/methanol (1: 1), be diluted to required concentration with the water that contains 0.1% tween 80.
With mythimna separata (Leucania separata), small cabbage moth (Plutella xylostella) and culex pipiens pollens (Culex pippens pallens) 2 instar larvaes, black peach aphid (Myzus persicae), carmine spider mite (Tetranychus cinnabarinus) is target; Adopt airbrush spray method and immersion method (culex pipiens pallens larvae) to carry out insecticidal activity assay, the pressure that the airbrush spraying is handled is that 10psi (is roughly equal to 0.7kg/cm
2), spouting liquid is 0.5 milliliter.Handle the mortality ratio that 2-3 day is investigated target in the back.
The partial test result is following:
When liquor strength was 20ppm, compound 1-12,1-115,1-135,1-167,1-220 reached 100% to the small cabbage moth mortality ratio, and compound 1-96 reaches more than 80% the small cabbage moth mortality ratio; When liquor strength was 15ppm, compound 2-4 reached 100% to the small cabbage moth mortality ratio; When liquor strength was 5ppm, compound 1-132,1-138,1-181,1-184,1-414 reached 100% to the small cabbage moth mortality ratio.
Claims (6)
1. O-formammidotiazol-benzamide compounds, shown in general formula I:
Y is selected from NH;
R
1Be selected from methyl;
R
2Be selected from halogen;
R
3Be selected from Cl or Br;
R
4Be selected from cyanic acid,
R
15Be selected from methyl; R
16Be selected from cyanic acid or C
1-C
3Alkoxy carbonyl;
Perhaps R
4Be selected from B-Z-Q, wherein:
B is selected from CH
2CH
2, Z is selected from NH, and Q is selected from Q1:
R
8Be selected from Cl;
R
9Be selected from Br.
2. according to the described compound of Formula I of claim 1, it is characterized in that:
Y is selected from NH;
R
1Be selected from methyl;
R
2Be selected from Cl;
R
3Be selected from Br;
R
4Be selected from cyanic acid,
3. according to the described compound of Formula I of claim 1, it is characterized in that:
Y is selected from NH;
R
1Be selected from methyl;
R
2Be selected from Cl;
R
3Be selected from Br;
R
4Be selected from B-Z-Q, wherein: B is selected from CH
2CH
2, Z is selected from NH, and Q is selected from Q1:
R
8Be selected from Cl;
R
9Be selected from Br.
4. application that in agriculture field, prevents and treats germ according to claim 1 or 2 described compound of Formula I.
5. application according to claim 1,2 or 3 described compound of Formula I pest control in agriculture field.
6. a desinsection, fungicidal compsn, it is characterized in that: contain compound of Formula I as claimed in claim 1 and go up acceptable carrier with agricultural, the weight percentage of active ingredient is 0.5-90% in the compsn.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007100111786A CN101298435B (en) | 2007-04-30 | 2007-04-30 | O-formammidotiazol-benzamide compounds and use thereof |
| PCT/CN2008/070832 WO2008134970A1 (en) | 2007-04-30 | 2008-04-28 | Anthranilamide compounds and the use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007100111786A CN101298435B (en) | 2007-04-30 | 2007-04-30 | O-formammidotiazol-benzamide compounds and use thereof |
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| Publication Number | Publication Date |
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| CN101298435B true CN101298435B (en) | 2012-02-15 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102134238A (en) * | 2010-01-25 | 2011-07-27 | 中化蓝天集团有限公司 | Fluoromethoxypyrazole-containing 4H-benzo[1,3]oxazine-4-ketone compound as well as preparation method and application thereof |
| JP6025717B2 (en) * | 2010-06-15 | 2016-11-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | Novel ortho-substituted arylamide derivatives |
| CN102285964B (en) * | 2010-06-21 | 2013-11-27 | 中国中化股份有限公司 | Cyanobenzamide compound and application thereof |
| CN102285965B (en) * | 2010-06-21 | 2013-11-27 | 中国中化股份有限公司 | N-(cyanoalkyl) benzamide compound and application thereof |
| CN102285963B (en) * | 2010-06-21 | 2014-04-09 | 中国中化股份有限公司 | 3-methoxy pyrazolecarboxamide compound and application thereof |
| CN101967139B (en) * | 2010-09-14 | 2013-06-05 | 中化蓝天集团有限公司 | Fluoro methoxylpyrazole-containing o-formylaminobenzamide compound, synthesis method and application thereof |
| CN102060770A (en) * | 2010-12-27 | 2011-05-18 | 浙江工业大学 | Preparation and application of o-formamido-benzamide compound and intermediate thereof |
| CN103172613B (en) * | 2013-01-05 | 2015-09-09 | 南开大学 | One class contains anthranilic diamides derivative of N-cyano group sulfone (sulphur) imines and its production and use |
| CN104031025B (en) * | 2013-01-05 | 2017-02-22 | 南开大学 | O-formylamino benzamide derivatives containing sulfone (sulfur)imine and preparation method and uses thereof |
| CN103450154B (en) * | 2013-09-18 | 2016-01-20 | 南开大学 | Substituted pyrazolecarboxylic benzamide type bisamide derivatives of one class Sulfide-containing Hindered, N-cyano group sulphur (sulfone) imine structure and its production and use |
| CN107001325B (en) * | 2014-11-05 | 2020-06-16 | 江苏中旗科技股份有限公司 | O-formamido benzamide compound and application thereof |
| CN105037324B (en) * | 2015-05-27 | 2018-12-07 | 江苏中旗科技股份有限公司 | O-formammidotiazol-benzamide compounds and its application with insecticidal activity |
| CN105130969A (en) * | 2015-09-06 | 2015-12-09 | 青岛科技大学 | N-furfuryl amide insecticide |
| CN105198801A (en) * | 2015-10-30 | 2015-12-30 | 武汉工程大学 | N-(4-chloro-3-picolyl)-2-(3-methylbenzamide) benzamide as well as preparation method and application thereof |
| CN105254625B (en) * | 2015-11-06 | 2018-07-27 | 青岛科技大学 | One kind class compound of yl-benzamide containing chloro-thiazole and its application |
| CN105541794A (en) * | 2016-01-08 | 2016-05-04 | 南开大学 | Heptafluoroisopropyl-containing pyridyl pyrazole amide derivative and application thereof |
| CN107759561B (en) * | 2016-08-18 | 2021-04-02 | 江苏中旗科技股份有限公司 | O-formamido benzamide compound with insecticidal activity and application thereof |
| CN106317016A (en) * | 2016-08-24 | 2017-01-11 | 河北艾林国际贸易有限公司 | Insect cyclopropanecarboxamide compound and preparing method thereof and application |
| CN111269224A (en) * | 2020-02-25 | 2020-06-12 | 华东理工大学 | Sydneone or sydnonimine-containing diamide compound and preparation and application thereof |
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