CN105566148B - A kind of quaternary ammonium compound and its application - Google Patents

A kind of quaternary ammonium compound and its application Download PDF

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Publication number
CN105566148B
CN105566148B CN201410539916.4A CN201410539916A CN105566148B CN 105566148 B CN105566148 B CN 105566148B CN 201410539916 A CN201410539916 A CN 201410539916A CN 105566148 B CN105566148 B CN 105566148B
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hydrogen
alkyl
halogen
ethyl
methyl
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CN105566148A (en
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杨吉春
吴峤
崔东亮
关爱莹
马宏娟
刘长令
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Abstract

The invention belongs to field of agricultural herbicide, and in particular to a kind of quaternary ammonium compound and its application.Quaternary ammonium compound is as shown in logical formula (I), logical formula (I) compound has good activity of weeding, the weeds such as barnyard grass, piemarker, green bristlegrass, youth-and-old-age can be efficiently controlled, good herbicidal effect is obtained with low dosage, and before seedling, to corn, cotton, after seedling is to wheat, corn safety.

Description

A kind of quaternary ammonium compound and its application
Technical field
The invention belongs to field of agricultural herbicide, and in particular to a kind of quaternary ammonium compound and its application.
Background technology
Patent EP0638843A2, US3080327A disclose the compound of below formula, are used as developer and denatured ethyl alcohol Additive.
X is halogen, hydroxyl and substituted benzoic acid etc..
Its Patent EP0638843A2 specifications page 5 disclose compound A (numbering is I-4 in patent).
In the prior art, the compound as shown in the logical formula (I) of the present invention has no that its activity of weeding is reported.
The content of the invention
For development of new herbicide to solve the problems, such as increasingly serious Herbicid resistant, the present invention provides a kind of quaternary ammonium salt Class compound and its application.
To achieve the above object, the technical solution adopted by the present invention is：
The present invention provides a kind of containing quaternary ammonium compound, as shown in logical formula (I)：
In formula：
R1、R2、R3It may be the same or different and be respectively selected from hydrogen, halogen, C1-C12Alkyl, C1-C12Haloalkyl, C3-C12Cycloalkanes Base, C1-C12Alkoxy, C1-C12Halogenated alkoxy, C1-C12It is halogenated alkylthio, unsubstituted or be independently selected from by 1-4 following Aryl, the heteroaryl of substituent group：Halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxy or halo C1-C6Alkoxy；
R4、R5It may be the same or different and be respectively selected from hydrogen, C1-C12Alkyl, C1-C12Haloalkyl or C3-C12Cycloalkyl；
R6Selected from hydrogen, C1-C12Alkyl, aryl, heteroaryl unsubstituted or that be independently selected from following substituent group by 1-4 Base：Halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxy or halo C1-C6Alkoxy；
R7Selected from hydrogen, C1-C12Alkyl, C1-C12Haloalkyl, (CH2)nCO2R8Or (CH2)nOR8；
N is selected from 0,1 or 2；
R8Selected from C1-C12Alkyl；
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9：
R9Selected from hydrogen, halogen, C1-C12Alkyl, C1-C12Haloalkyl, C1-C12Alkoxy, C1-C12Halogenated alkoxy, C1- C12Alkoxy C1-C12Alkyl, C2-C12Alkenyl, C3-C12Cycloalkyl or C1-C12Halogenated alkylthio；
R10Selected from hydrogen, halogen, C1-C12Alkyl, C1-C12Alkoxy, C2-C12Alkenyl, C1-C12Haloalkyl or C1-C12Halogen For alkoxy；Or R9、R10Five-membered ring or hexatomic ring can be formed；
R11Selected from CH or N；
R12、R13、R14、R17、R30It is respectively selected from hydrogen, halogen or C1-C12Alkyl；
R15、R16、R23、R24It is respectively selected from hydrogen, halogen or C1-C12Alkyl, C1-C12Haloalkyl, C1-C12Alkoxy, C1- C12Halogenated alkoxy, C1-C12Alkoxy C1-C12Alkyl, C2-C12Alkenyl, C3-C12Cycloalkyl or C1-C12Halogenated alkylthio；R18 Selected from C1-C12Alkyl, C1-C12Haloalkyl, phenyl, pyridine unsubstituted or that be independently selected from following substituent group by 1-4 Base, pyrimidine radicals, pyrazolyl, thiazolyl, quinolyl, benzoxazolyl or quinoxalinyl：Halogen, nitro, cyano group, C1-C6Alkyl, Halo C1-C6Alkyl, C1-C6Alkoxy or halo C1-C6Alkoxy；
R19、R20、R22It is respectively selected from hydrogen, halogen, C1-C12Alkyl, C1-C12Haloalkyl, C1-C12Alkoxy or C1-C12Halogen For alkoxy；
R21Selected from hydrogen, halogen or NH2；
R25Selected from hydrogen, halogen, nitro, C1-C12Alkyl, C1-C12Haloalkyl, C1-C12Alkoxy, C1-C12Haloalkoxy Base, C1-C12Alkoxy C1-C12Alkyl, C2-C12Alkenyl, C3-C12Cycloalkyl or C1-C12Halogenated alkylthio；
R26、R27What be may be the same or different is respectively selected from hydrogen, C1-C12Alkyl or C1-C12Alkoxy；
R28Selected from O or S；
R29Selected from hydrogen, halogen, pyrimidine radicals that is unsubstituted or being independently selected from following substituent group by 1-4：Halogen, C1- C6Alkyl or C1-C6Alkoxy；
R31Selected from halogen, C1-C12Alkyl, C1-C12Haloalkyl, C1-C12Alkoxy or C1-C12Halogenated alkoxy；
R32Selected from hydrogen, C1-C12Alkyl, pyridine radicals or benzene unsubstituted or that be independently selected from following substituent group by 1-4 Base：Halogen, C1-C6Alkyl or halo C1-C6Alkyl.
R33、R34Selected from hydrogen, halogen, nitro, C1-C12Alkyl, C1-C12Haloalkyl, C1-C12Alkoxy or C1-C12Halo Alkoxy；
R35Selected from hydrogen, C1-C12Alkyl, C1-C12Haloalkyl, C1-C12Alkoxy or C1-C12Halogenated alkoxy；
The present invention more more preferred compound is：In logical formula (I)
R1、R2、R3It may be the same or different and be respectively selected from hydrogen, halogen, C1-C12Alkyl, C1-C12Haloalkyl, C3-C12Cycloalkanes Base, C1-C12Alkoxy, C1-C12Halogenated alkoxy or C1-C12Halogenated alkylthio；
R4、R5It may be the same or different and be respectively selected from hydrogen, C1-C12Alkyl, C1-C12Haloalkyl or C3-C12Cycloalkyl；
R6Selected from hydrogen, C1-C12Alkyl, aryl, heteroaryl unsubstituted or that be independently selected from following substituent group by 1-4 Base：Halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxy or halo C1-C6Alkoxy；
R7Selected from hydrogen, C1-C12Alkyl, C1-C12Haloalkyl, (CH2)nCO2R8Or (CH2)nOR8；
N is selected from 0,1 or 2；
R8Selected from C1-C12Alkyl；
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9；
R9Selected from hydrogen, halogen, C1-C12Alkyl, C1-C12Haloalkyl, C1-C12Alkoxy, C1-C12Halogenated alkoxy, C1- C12Alkoxy C1-C12Alkyl or C2-C12Alkenyl；
R10Selected from hydrogen, halogen, C1-C12Alkyl or C2-C12Alkenyl；Or R9、R10Hexatomic ring can be formed；R11Selected from CH or N；
R12、R13、R14、R17、R30It is respectively selected from hydrogen, halogen or C1-C12Alkyl；
R15、R16、R23、R24It is respectively selected from hydrogen, halogen or C1-C12Alkyl；
R18Selected from C1-C12Alkyl, C1-C12It is haloalkyl, unsubstituted or following substituent group is independently selected from by 1-4 Phenyl, pyridine radicals, quinolyl, benzoxazolyl or quinoxalinyl：Halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkane Base, C1-C6Alkoxy or halo C1-C6Alkoxy；
R19、R20、R22It is respectively selected from hydrogen or halogen；
R21Selected from hydrogen, halogen or NH2；
R25Selected from hydrogen, halogen or nitro；
R26、R27What be may be the same or different is respectively selected from hydrogen, C1-C12Alkyl or C1-C12Alkoxy；
R28Selected from O or S；
R29Selected from hydrogen, halogen, pyrimidine radicals that is unsubstituted or being independently selected from following substituent group by 1-4：Halogen, C1- C6Alkyl or C1-C6Alkoxy；
R31Selected from halogen or C1-C12Alkyl；
R32Selected from hydrogen, C1-C12Alkyl, pyridine radicals that is unsubstituted or being independently selected from following substituent group by 1-4：Halogen Element, C1-C6Alkyl or halo C1-C6Alkyl.
R33、R34Selected from hydrogen, halogen, C1-C12Alkyl, C1-C12Haloalkyl, C1-C12Alkoxy or C1-C12Haloalkoxy Base；
R35Selected from hydrogen, C1-C12Alkyl, C1-C12Haloalkyl or C1-C12Alkoxy；
More preferred compound is the present invention again：In logical formula (I)
R1、R2、R3It may be the same or different and be respectively selected from hydrogen, halogen, C1-C8Alkyl, C1-C8Haloalkyl, C3-C8Cycloalkyl, C1-C8Alkoxy, C1-C8Halogenated alkoxy or C1-C8Halogenated alkylthio；
R4、R5It may be the same or different and be respectively selected from hydrogen, C1-C8Alkyl, C1-C8Haloalkyl or C3-C8Cycloalkyl；
R6Selected from hydrogen, C1-C8Alkyl, aryl, heteroaryl unsubstituted or that be independently selected from following substituent group by 1-4： Halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy or halo C1-C4Alkoxy；
R7Selected from hydrogen, C1-C8Alkyl, C1-C8Haloalkyl, (CH2)nCO2R8Or (CH2)nOR8；
N is selected from 0,1,2；
R8Selected from C1-C8Alkyl；
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9；
R9Selected from hydrogen, halogen, C1-C8Alkyl, C1-C8Haloalkyl, C1-C8Alkoxy, C1-C8Halogenated alkoxy, C1-C8Alkane Epoxide C1-C8Alkyl or C2-C8Alkenyl；
R10Selected from hydrogen, halogen, C1-C8Alkyl or C2-C8Alkenyl；Or R9、R10Hexatomic ring can be formed；
R11Selected from CH or N；
R12、R13、R14、R17、R30It is respectively selected from hydrogen, halogen or C1-C8Alkyl；
R15、R16、R23、R24It is respectively selected from hydrogen, halogen or C1-C8Alkyl；
R18Selected from C1-C8Alkyl, C1-C8It is haloalkyl, unsubstituted or following substituent group is independently selected from by 1-4 Phenyl, pyridine radicals, quinolyl, benzoxazolyl or quinoxalinyl：Halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkane Base, C1-C4Alkoxy or halo C1-C4Alkoxy；
R19、R20、R22It is respectively selected from hydrogen or halogen；
R21Selected from hydrogen, halogen or NH2；
R25Selected from hydrogen, halogen or nitro；
R26、R27What be may be the same or different is respectively selected from hydrogen, C1-C8Alkyl or C1-C8Alkoxy；
R28Selected from O or S；
R29Selected from hydrogen, halogen, pyrimidine radicals that is unsubstituted or being independently selected from following substituent group by 1-4：Halogen, C1- C4Alkyl or C1-C4Alkoxy；
R31Selected from halogen or C1-C8Alkyl；
R32Selected from hydrogen, C1-C8Alkyl, pyridine radicals that is unsubstituted or being independently selected from following substituent group by 1-4：Halogen Element, C1-C6Alkyl or halo C1-C6Alkyl.
R33、R34Selected from hydrogen, halogen, C1-C8Alkyl, C1-C8Haloalkyl, C1-C8Alkoxy or C1-C8Halogenated alkoxy；
R35Selected from hydrogen, C1-C8Alkyl, C1-C8Haloalkyl or C1-C8Alkoxy；
The further preferred compound of the present invention is：In logical formula (I)
R1、R2、R3It may be the same or different and be respectively selected from hydrogen, halogen, C1-C6Alkyl, C1-C6Haloalkyl, C3-C6Cycloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy or C1-C6Halogenated alkylthio；
R4、R5It may be the same or different and be respectively selected from hydrogen, C1-C6Alkyl, C1-C6Haloalkyl or C3-C6Cycloalkyl；
R6Selected from hydrogen, C1-C6Alkyl, aryl, heteroaryl unsubstituted or that be independently selected from following substituent group by 1-4： Halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkyl, C1-C4Alkoxy or halo C1-C4Alkoxy；
R7Selected from hydrogen, C1-C6Alkyl, C1-C6Haloalkyl, (CH2)nCO2R8Or (CH2)nOR8；
N is selected from 0,1,2；
R8Selected from C1-C6Alkyl；
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9；
R9Selected from hydrogen, halogen, C1-C6Alkyl, C1-C6Haloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkane Epoxide C1-C6Alkyl or C2-C6Alkenyl；
R10Selected from hydrogen, halogen, C1-C6Alkyl or C2-C6Alkenyl；Or R9、R10Hexatomic ring can be formed；
R11Selected from CH or N；
R12、R13、R14、R17、R30It is respectively selected from hydrogen, halogen or C1-C6Alkyl；
R15、R16、R23、R24It is respectively selected from hydrogen, halogen or C1-C6Alkyl；
R18Selected from C1-C6Alkyl, C1-C6It is haloalkyl, unsubstituted or following substituent group is independently selected from by 1-4 Phenyl, pyridine radicals, quinolyl, benzoxazolyl or quinoxalinyl：Halogen, nitro, cyano group, C1-C4Alkyl, halo C1-C4Alkane Base, C1-C4Alkoxy or halo C1-C4Alkoxy；
R19、R20、R22It is respectively selected from hydrogen or halogen；
R21Selected from hydrogen, halogen or NH2；
R25Selected from hydrogen, halogen or nitro；
R26、R27What be may be the same or different is respectively selected from hydrogen, C1-C6Alkyl or C1-C6Alkoxy；
R28Selected from O or S；
R29Selected from hydrogen, halogen, pyrimidine radicals that is unsubstituted or being independently selected from following substituent group by 1-4：Halogen, C1- C4Alkyl or C1-C4Alkoxy；
R31Selected from halogen or C1-C4Alkyl；
R32Selected from hydrogen, C1-C4Alkyl, pyridine radicals that is unsubstituted or being replaced by 1-4 halogen.
R33、R34Selected from hydrogen, halogen, C1-C6Alkyl, C1-C6Haloalkyl, C1-C6Alkoxy or C1-C6Halogenated alkoxy；
R35Selected from hydrogen, C1-C6Alkyl, C1-C6Haloalkyl or C1-C6Alkoxy；
Present invention compound still further preferably is：In logical formula (I)
R1、R2、R3It may be the same or different and be respectively selected from hydrogen, halogen, methyl, ethyl, propyl group, isopropyl, cyclopropyl, tertiary fourth Base, methoxyl group, trifluoromethoxy, difluoro-methoxy, trifluoromethyl or difluoromethyl；
R4、R5It may be the same or different and be respectively selected from hydrogen, methyl, ethyl or propyl group；
R6Selected from hydrogen, methyl, ethyl, propyl group, butyl, unsubstituted or be independently selected from following substituent group by 1-4 Phenyl：Halogen, nitro, cyano group or C1-C3Alkyl；
R7Selected from hydrogen, (CH2)nCO2R8Or (CH2)nOR8；
N is selected from 0,1,2；
R8Selected from C1-C4Alkyl；
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9；
R9Selected from hydrogen, fluorine, chlorine, methyl, ethyl, the tert-butyl group, trifluoromethyl, methoxyl group, trifluoromethoxy or methoxy methyl Base ether；
R10Selected from hydrogen；Or R9、R10Phenyl ring can be formed；
R11Selected from CH or N；
R12、R13、R14、R17、R30It is respectively selected from hydrogen, halogen, methyl, ethyl, isopropyl or the tert-butyl group；
R15、R16、R23、R24It is respectively selected from hydrogen, fluorine, chlorine, methyl, ethyl, isopropyl or the tert-butyl group；
R18Selected from methyl, ethyl, isopropyl, the tert-butyl group, trifluoromethyl, difluoromethyl, unsubstituted or independent by 1-3 Phenyl, pyridine radicals, quinolyl, benzoxazolyl or quinoxalinyl selected from following substituent group：Fluorine, chlorine, nitro, cyano group, first Base, ethyl, the tert-butyl group, trifluoromethyl, difluoromethyl, trichloromethyl, methoxyl group, trifluoromethoxy or difluoro-methoxy；
R19、R20、R22It is respectively selected from hydrogen, fluorine or chlorine；
R21Select NH2；
R25Selected from hydrogen, fluorine, chlorine or nitro；
R26、R27What be may be the same or different is respectively selected from hydrogen or methoxyl group；
R28Selected from O or S；
R29Selected from hydrogen, fluorine, chlorine or 4,6- dimethoxy -2- pyrimidine radicals；
R31Selected from halogen, methyl, ethyl, isopropyl or the tert-butyl group；
R32Selected from hydrogen, methyl, ethyl, pyridine radicals that is unsubstituted or being replaced by 1-4 chlorine atom.
R33、R34Selected from hydrogen, halogen, C1-C4Alkyl, C1-C4Haloalkyl, C1-C4Alkoxy or C1-C4Halogenated alkoxy；
R35Selected from hydrogen, C1-C4Alkyl, C1-C4Haloalkyl or C1-C4Alkoxy；
Present invention compound still more preferably is：In logical formula (I)
R1、R2、R3It may be the same or different and be respectively selected from hydrogen, halogen, methyl, ethyl, propyl group, isopropyl, cyclopropyl, tertiary fourth Base, methoxyl group, trifluoromethoxy, difluoro-methoxy, trifluoromethyl or difluoromethyl；
R4、R5It may be the same or different and be respectively selected from hydrogen, methyl, ethyl or propyl group；
R6Selected from hydrogen, methyl, ethyl, propyl group, phenyl that is unsubstituted or being independently selected from following substituent group by 1-4： Halogen, nitro, cyano group or C1-C3Alkyl；
R7Selected from hydrogen, (CH2)nCO2R8Or (CH2)nOR8；
N is selected from 0,1,2；
R8Selected from methyl or ethyl.
Q is selected from one of group as follows：
Present invention compound again still more preferably is：In logical formula (I)
R1、R2、R3It may be the same or different and be respectively selected from hydrogen, halogen, methyl or ethyl；
R4、R5It may be the same or different and be respectively selected from hydrogen, methyl or ethyl；
R6Selected from phenyl that is unsubstituted or being independently selected from following substituent group by 1-4：Halogen, nitro, cyano group or C1- C3Alkyl；
R7Selected from hydrogen or (CH2)nCO2R8；
N is selected from 0 or 1；
R8Selected from methyl or ethyl.
Q is selected from Q1-4, Q2-1, Q2-2, Q2-3, Q3-7, Q3-8, Q6-1, Q6-2, Q8-1, Q8-2 or Q9-1.
The highly preferred compound of the present invention is：In logical formula (I)
R1、R2It is respectively selected from methyl or ethyl；
R3Selected from hydrogen；
R4、R5It may be the same or different and be respectively selected from methyl or ethyl；
R6Selected from unsubstituted phenyl；
R7Selected from hydrogen or (CH2)nCO2R8；
N is selected from 1；
R8Selected from ethyl；
Q is selected from Q1-4, Q2-3, Q3-7, Q6-1, Q8-1 or Q9-1.
In the definition of logical formula (I) compound given above, collect term used and be typically defined as follows：
Halogen：Refer to fluorine, chlorine, bromine or iodine.Alkyl：Straight or branched alkyl, such as methyl, ethyl, propyl group, isopropyl, just Butyl or the tert-butyl group.Cycloalkyl：Substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopenta or cyclohexyl.Substituent is such as Methyl, halogen etc..Haloalkyl：Straight or branched alkyl, the hydrogen atom on these alkyl can be partly or entirely by halogen atom Replaced, for example, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl etc..Alkoxy：Straight chain or Branched alkyl, is connected in structure through oxygen atom key.Halogenated alkoxy：Straight or branched alkoxyl, on these alkoxies Hydrogen atom partly or entirely can be replaced by halogen atom.For example, chloromethane epoxide, dichloro methoxyl group, trichloromethoxy, fluorine methoxy Base, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group, trifluoro ethoxy etc..Halogenated alkylthio：Straight or branched alkylthio group, Hydrogen atom on these alkyl partly or entirely can be replaced by halogen atom.For example, chloromethane sulfenyl, dichloro methyl mercapto, trichlorine Methyl mercapto, fluorine methyl mercapto, difluoro methyl mercapto, trifluoromethylthio, chlorine fluorine methyl mercapto etc..Alkenyl：Straight or branched alkenes, such as second Alkenyl, 1- acrylic, 2- acrylic and different cyclobutenyls, pentenyl and hexenyl isomers.Alkenyl also includes many alkenes, such as 1,2- allene base and 2,4- hexadienyls.Aryl：Polynary aromatic group, such as phenyl, naphthyl.Heteroaryl is to contain one or more The heteroatomic five-membered ring of N, O, S or hexatomic ring.Such as furyl, pyrazolyl, thiazolyl, pyridine radicals, pyrimidine radicals, pyrazinyl, rattle away Piperazine base, triazine radical, quinolyl etc..
The present invention part of compounds can be illustrated with the particular compound listed in table 1, but the present invention and not only limit In these compounds.
Wherein R3=H, R6=Ph
Table 1
Numbering R1 R2 R4 R5 R7 Q
1 CH3 CH3 CH3 CH3 H Q1-4
2 CH3 CH3 CH3 CH3 H Q2-1
3 CH3 CH3 CH3 CH3 H Q2-2
4 CH3 CH3 CH3 CH3 H Q2-3
5 CH3 CH3 CH3 CH3 H Q3-7
6 CH3 CH3 CH3 CH3 H Q3-8
7 CH3 CH3 CH3 CH3 H Q6-1
8 CH3 CH3 CH3 CH3 H Q6-2
9 CH3 CH3 CH3 CH3 H Q8-1
10 CH3 CH3 CH3 CH3 H Q8-2
11 CH3 CH3 CH3 CH3 H Q9-1
12 CH2CH3 CH2CH3 CH3 CH3 H Q1-4
13 CH2CH3 CH2CH3 CH3 CH3 H Q2-1
14 CH2CH3 CH2CH3 CH3 CH3 H Q2-2
15 CH2CH3 CH2CH3 CH3 CH3 H Q2-3
16 CH2CH3 CH2CH3 CH3 CH3 H Q3-7
17 CH2CH3 CH2CH3 CH3 CH3 H Q3-8
18 CH2CH3 CH2CH3 CH3 CH3 H Q6-1
19 CH2CH3 CH2CH3 CH3 CH3 H Q6-2
20 CH2CH3 CH2CH3 CH3 CH3 H Q8-1
21 CH2CH3 CH2CH3 CH3 CH3 H Q9-1
22 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q1-4
23 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q2-1
24 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q2-2
25 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q2-3
26 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q3-7
27 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q3-8
28 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q6-1
29 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q6-2
30 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q8-1
31 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H Q9-1
32 CH3 CH3 CH2CH3 CH2CH3 H Q1-4
33 CH3 CH3 CH2CH3 CH2CH3 H Q2-1
34 CH3 CH3 CH2CH3 CH2CH3 H Q2-2
35 CH3 CH3 CH2CH3 CH2CH3 H Q2-3
36 CH3 CH3 CH2CH3 CH2CH3 H Q3-7
37 CH3 CH3 CH2CH3 CH2CH3 H Q3-8
38 CH3 CH3 CH2CH3 CH2CH3 H Q6-1
39 CH3 CH3 CH2CH3 CH2CH3 H Q6-2
40 CH3 CH3 CH2CH3 CH2CH3 H Q8-1
41 CH3 CH3 CH2CH3 CH2CH3 H Q9-1
42 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q1-4
43 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q2-1
44 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q2-2
45 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q2-3
46 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q3-7
47 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q3-8
48 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q6-1
49 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q6-2
50 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q8-1
51 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q8-2
52 CH3 CH3 CH3 CH3 CH2CO2C2H5 Q9-1
53 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q1-4
54 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q2-1
55 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q2-2
56 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q2-3
57 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q3-7
58 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q3-8
59 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q6-1
60 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q6-2
61 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q8-1
62 CH2CH3 CH2CH3 CH3 CH3 CH2CO2C2H5 Q9-1
63 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q1-4
64 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q2-1
65 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q2-2
66 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q2-3
67 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q3-7
68 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q3-8
69 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q6-1
70 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q6-2
71 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q8-1
72 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q9-1
73 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q1-4
74 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q2-1
75 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q2-2
76 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q2-3
77 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q3-7
78 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q3-8
79 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q6-1
80 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q6-2
81 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q8-1
82 CH3 CH3 CH2CH3 CH2CH3 CH2CO2C2H5 Q9-1
83 CH3 CH3 CH3 CH3 CH2OC2H5 Q1-4
84 CH3 CH3 CH3 CH3 CH2OC2H5 Q2-1
85 CH3 CH3 CH3 CH3 CH2OC2H5 Q2-2
86 CH3 CH3 CH3 CH3 CH2OC2H5 Q2-3
87 CH3 CH3 CH3 CH3 CH2OC2H5 Q3-7
88 CH3 CH3 CH3 CH3 CH2OC2H5 Q3-8
89 CH3 CH3 CH3 CH3 CH2OC2H5 Q6-1
90 CH3 CH3 CH3 CH3 CH2OC2H5 Q6-2
91 CH3 CH3 CH3 CH3 CH2OC2H5 Q8-1
92 CH3 CH3 CH3 CH3 CH2OC2H5 Q8-2
93 CH3 CH3 CH3 CH3 CH2OC2H5 Q9-1
94 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q1-4
95 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q2-1
96 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q2-2
97 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q2-3
98 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q3-7
99 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q3-8
100 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q6-1
101 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q6-2
102 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q8-1
103 CH2CH3 CH2CH3 CH3 CH3 CH2OC2H5 Q9-1
104 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q1-4
105 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q2-1
106 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q2-2
107 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q2-3
108 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q3-7
109 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q3-8
110 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q6-1
111 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q6-2
112 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q8-1
113 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OC2H5 Q9-1
114 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q1-4
115 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q2-1
116 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q2-2
117 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q2-3
118 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q3-7
119 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q3-8
120 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q6-1
121 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q6-2
122 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q8-1
123 CH3 CH3 CH2CH3 CH2CH3 CH2OC2H5 Q9-1
124 CH3 CH3 CH3 CH3 CH2OCH3 Q1-4
125 CH3 CH3 CH3 CH3 CH2OCH3 Q2-1
126 CH3 CH3 CH3 CH3 CH2OCH3 Q2-2
127 CH3 CH3 CH3 CH3 CH2OCH3 Q2-3
128 CH3 CH3 CH3 CH3 CH2OCH3 Q3-7
129 CH3 CH3 CH3 CH3 CH2OCH3 Q3-8
130 CH3 CH3 CH3 CH3 CH2OCH3 Q6-1
131 CH3 CH3 CH3 CH3 CH2OCH3 Q6-2
132 CH3 CH3 CH3 CH3 CH2OCH3 Q8-1
133 CH3 CH3 CH3 CH3 CH2OCH3 Q8-2
134 CH3 CH3 CH3 CH3 CH2OCH3 Q9-1
135 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q1-4
136 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q2-1
137 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q2-2
138 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q2-3
139 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q3-7
140 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q3-8
141 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q6-1
142 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q6-2
143 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q8-1
144 CH2CH3 CH2CH3 CH3 CH3 CH2OCH3 Q9-1
145 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q1-4
146 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q2-1
147 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q2-2
148 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q2-3
149 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q3-7
150 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q3-8
151 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q6-1
152 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q6-2
153 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q8-1
154 CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2OCH3 Q9-1
155 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q1-4
156 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q2-1
157 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q2-2
158 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q2-3
159 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q3-7
160 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q3-8
161 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q6-1
162 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q6-2
163 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q8-1
164 CH3 CH3 CH2CH3 CH2CH3 CH2OCH3 Q9-1
The logical formula (I) compound of the present invention can be prepared by the following method, and outer except as otherwise indicating, each group definition is same in reaction equation Before.
Logical formula (I) compound can be made as leading to the villaumite shown in formula (II) with the acid condensation shown in logical formula (III).
Reaction in suitable solvent carry out, suitable solvent may be selected from benzene,toluene,xylene, acetone, tetrahydrofuran, Acetonitrile, N,N-dimethylformamide, 1-METHYLPYRROLIDONE, dichloromethane, chloroform, dichloroethanes or ethyl acetate, methanol, second Alcohol etc..Reaction can be carried out in the presence of alkali or alkali-free, when being reacted in the presence of alkali, and reaction can be accelerated to carry out. Described alkali can be selected from alkali metal hydride, such as sodium hydride；Alkali metal hydroxide, such as sodium hydroxide or potassium hydroxide；Alkali Metal carbonate, such as sodium carbonate or potassium carbonate；Organic bases, such as pyridine, DMAP, triethylamine, N- methylpyrroles Or diisopropyl ethyl amine etc..Reaction temperature can be led between -10 DEG C of suitable solvent boiling point temperature selected into reacting It is often 0~100 DEG C.Reaction time is 30 minutes to 20 hours, usual 1~10 hour.
Compound shown in logical formula (II) can be made by known method, referring specifically to US3080327A：Preparation process is to incite somebody to action (IV) with (V) in suitable solvent or frit reaction generation (II).Suitable solvent may be selected from dichloromethane, chloroform, tetrachloro Change carbon, petroleum ether or toluene, dimethylbenzene etc..Reaction temperature can in room temperature between suitable solvent boiling point temperature, usually 20 ~200 DEG C.Reaction time is 30 minutes to 30 hours, usual 5~24 hours.(V) benzyl chloride shown in is commercially available.
Compound shown in logical formula (IV) can be made by known method, referring specifically to US3080327A.
The compound of the present invention can efficiently control the weeds such as barnyard grass, youth-and-old-age, green bristlegrass, piemarker, under low dosage It is obtained with good effect.It is good to crop safety, especially to corn safety, it agriculturally can be used as herbicide.Therefore It is used for the purposes for controlling weeds present invention additionally comprises logical formula (I) compound.
Present invention also offers a kind of Herbicidal combinations, said composition is using logical formula (I) compound as active component, combination The weight percentage of active component in thing is 0.1-99%.Therefore it is used to control weeds present invention additionally comprises said composition Purposes.
The composition of the present invention can prepare corresponding formulation using method well known to those skilled in the art.Activearm Divide the mixture of the single compound or several compounds that can contain the present invention.
Carrier system in the present composition meets the material of following conditions：It is easy to be applied to after preparing with active component Pending site, for example, can be plant, seed or soil；Or be conducive to storing, transport or operating.Carrier can be solid Body or liquid, including be usually gas but be compressed into the material of liquid, generally carrier used in Herbicidal combinations are prepared It can be used.
Suitable solid carrier includes the clay and silicate (such as diatomite, talcum, Attagel, silicic acid naturally synthesized Aluminium (kaolin), montmorillonite and mica；), calcium carbonate, calcium sulfate, ammonium sulfate, synthesis silica, synthetic calcium silicate, synthesis silicon Sour aluminium, natural resin, resin (natural resin, the resin such as cumarone resin of synthesis, polyvinyl chloride and the benzene second of synthesis Alkene polymer and copolymer), solid polystream phenol, pitch or wax (such as beeswax, paraffin).
Suitable liquid-carrier includes water；Alcohol (such as isopropanol and ethanol；Ketone such as acetone, methyl ethyl ketone, isopropyl methyl Ketone, cyclohexyl ketone), ether, aromatic hydrocarbons (such as benzene,toluene,xylene), petroleum distillate (such as kerosene and mineral oil), chlorohydrocarbon (such as tetrachloro Change carbon, perchloroethylene and trichloro ethylene) in one or more of mixing.
Composition is generally processed into the form of concentrate and is used to transport with this, by user that its is dilute before administration Release.The presence of a small amount of supporting surfactant contributes to dilution.So, according in the composition of the present invention at least one Plant carrier and be preferably surfactant.For example composition can contain at least two carriers, and wherein at least one is surfactant.
Surfactant can be emulsifying agent, dispersant or wetting agent；It can be that non-ionic or ion surface is lived Property agent.The example of suitable surfactant includes the sodium salt or calcium salt of polyacrylic acid and lignin sulfonic acid；Containing at least in molecule The aliphatic acid or fatty amine or acid amides of 12 carbon atoms and oxirane and/or the condensation product of expoxy propane.Glycol, sorbierite, Sucrose or pentaerythritol fatty ester and these esters and oxirane and/or the condensation product of expoxy propane；Fatty alcohol or alkylbenzene Phenol such as POP or to octyl group cresols and oxirane and/or the condensation product of expoxy propane；The sulphur of these condensation products Hydrochlorate and sulfonate；At least alkali metal or alkali salt of the sulfuric acid containing 10 carbon atoms or sulphonic acid ester, excellent in the molecule Select sodium salt, such as sulfuric acid laurate sodium, the secondary Arrcostab sodium of sulfuric acid, sulfonated castor oil sodium salt, alkyl aryl sulfonic acid ester sodium, such as ten Dialkyl benzene sulfonic acids sodium salt.
The example of the composition of the present invention is wettable powder, pulvis, granule, aqua, emulsifiable concentrating agents, breast Agent, aerosol and smoke agent.The active component of the wettable powder generally weight containing 25-75%, and generally remove solid inert carrier Outside, the also dispersant containing 3-10% weight, and if desired can add the stabilizer and/or other additives of 0-10% weight Such as bleeding agent or sticker.Pulvis generally can be the pulvis concentration with the composition similar to wettable powder but without dispersant Agent, is further diluted with solid carrier, obtains the composition of the active component of the usual weight containing 0.5-10%.Granula is generally made It is standby into 10 to 100 mesh (1.676-0.152mm) size, and the preparation of agglomerating or injection technique can be used.Usual granula contains 0.5- The active component of 75% weight and additive (additive such as stabilizer, surfactant or the sustained release improvement of 0-10% weight Agent).Emulsifiable concentrating agents in addition to the solvents, usually contains cosolvent, 1-50%W/V active components, 2-20%W/V breasts when needed Agent and the other additives of 0-20%W/V (additive such as stabilizer, bleeding agent or corrosion inhibitor).Suspension concentrating agents generally contains There are other additive (additives of the active component, the dispersant of 0.5-15% weight, 0.1-10% weight of 10-75% weight Such as defoamer, corrosion inhibitor, stabilizer, bleeding agent and sticker).
Water dispersant and emulsion, the group for example obtained by the wettable powder or concentrate that are diluted with water according to the present invention Compound, is also included in the scope of the invention.Described emulsion can have two types of Water-In-Oil or oil-in-water.
, can be than single logical formula (I) compound by adding other one or more herbicides in the composition With broader spectrum of activity.In addition, other herbicides can the activity of weeding of mutual-through type (I) compound there is synergistic effect, also may be used By logical formula (I) compound and other herbicide mixtures, the changes of contents scope of active ingredient is very big in mixture, in mixture effectively into Divide content general in 1%-95%, convenient content is in 5%-60%.
Advantage for present invention：, can be effective using the logical formula (I) compound of the present invention as the composition of active component Control weeds, such compound can effectively control the weeds such as barnyard grass, piemarker, green bristlegrass, youth-and-old-age, and before seedling as herbicide To corn, cotton, after seedling agriculturally can be used as herbicide to wheat, corn safety.
Embodiment
Specific examples below is used for further illustrating the present invention, but the present invention is limited to absolutely not these examples.(except as otherwise note It is bright outer, raw materials used to be commercially available)
Synthetic example
The preparation of the compound of embodiment 1 (63)
1) preparation of intermediate (VII-1)
10g sodium carbonate (0.1mol) is soluble in water, 200ml toluene is added after dissolving, 10g2,6- diethylanilines is added 7.7g chloracetyl chlorides (0.068mol) are added dropwise under (0.068mol), ice bath, are stirred at room temperature 2 hours, TLC monitoring reactions are finished, instead Mixture suction filtration is answered, is washed, petroleum ether is washed, and obtains pink solid (VII-1).122-124 DEG C of fusing point
2) preparation of intermediate (IV-1)
13g (VII-1) (0.058mol) is added into 500ml there-necked flasks, 200ml acetonitriles are added, 12g potassium carbonate is added (0.087mol), is added dropwise 4.2g diethylamine (0.058mol), is heated to reflux 3 hours, solution is changed into pale yellow muddiness.Reaction is complete Afterwards, reactant mixture suction filtration, filtrate precipitation obtains yellow solid (IV-1).78-80 DEG C of fusing point.
3) preparation of intermediate (II-1)
11g (IV-1) (0.042mol) is added 250ml bottles, 5.3g (V-1) is added, 25ml toluene, back flow reaction is added 24 hours.There is a small amount of solid to separate out after cooling, plus ethyl acetate backflow 1 hour, solution becomes white opacity, and suction filtration after cooling is obtained White solid (II-1), 174-176 DEG C of fusing point.
4) preparation of compound (63)
0.1g potassium hydroxide (0.0018mol) is dissolved in 25ml methanol, 0.7g (II-1) (0.0018mol), room is added Temperature stirring 1 hour, suction filtration filters out potassium chloride, and 0.5g (III-1) (0.0018mol) is added into filtrate, flows back 10 minutes, precipitation, 10ml ether is added, white solid generation, suction filtration has been stirred at room temperature.168 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, solvent CDCl3)δppm0.86(9H,m),1.02(3H,t),1.22(6H,m),1.42(6H,m),2.16(1H,m),2.50(2H,m), 2.58(4H,m),2.76(2H,t),3.55(2H,s),3.65(2H,s),7.21(1H,s),7.23(3H,t),7.30(6H,s), 8.00(1H,s),8.56(1H,s)。
The preparation of the compound of embodiment 2 (15)
Preparation method is with reference to the 4) step of embodiment 1 the.White solid, 230.5 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, Solvent C DCl3)δppm1.07(6H,t),1.42(6H,t),2.43(4H,m),3.46(4H,m),4.46(6H,s),6.77(3H, d),7.19(2H,d),7.42(6H,m),8.86(1H,s)。
The preparation of the compound of embodiment 3 (31)
Preparation method is with reference to the 4) step of embodiment 1 the.White solid, 165 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, it is molten Agent CDCl3)δppm1.12(6H,t),1.47(6H,t),2.53(4H,d),3.56(4H,m),3.85(6H,s),4.14(2H, s),4.81(2H,d),7.16(2H,d),7.19(2H,d),7.33(2H,d),7.54(4H,s)。
The preparation of the compound of embodiment 4 (32)
Preparation method be the same as Example 1.White solid, 171 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, solvent C DCl3) δppm0.78(3H,d),0.99(3H,d),1.20(3H,t),1.34(3H,s),1.43(6H,t),2.00(1H,m),2.16 (6H,s),2.70(2H,d),3.54(4H,m),4.13(2H,s),4.76(2H,s),7.17(3H,d),7.50(6H,s),7.88 (1H,s),8.43(1H,s)。
The preparation of the compound of embodiment 5 (35)
Preparation method is with reference to the 4) step of embodiment 1 the.White solid, 185.3 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, Solvent C DCl3)δppm1.47(6H,t),2.20(6H,s),3.52(2H,d),3.57(4H,t),4.50(2H,s),4.85(2H, s),6.82(1H,d),7.22(4H,m),7.47(1H,d),7.54(5H,d),8.89(1H,s)。
The preparation of the compound of embodiment 6 (36)
Preparation method is with reference to the 4) step of embodiment 1 the.Red solid, 93 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, it is molten Agent CDCl3)δppm1.20(3H,s),1.47(6H,t),2.50(6H,s),3.58(4H,m),4.11(1H,dd),4.49(2H, m),6.75(8H,m),7.21(2H,d),7.55(4H,d),8.02(1H,s)。
The preparation of the compound of embodiment 7 (38)
Preparation method is with reference to the 4) step of embodiment 1 the.Gray solid, 116.2 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, Solvent C DCl3)δppm1.47(6H,t),2.20(6H,t),3.49(4H,m),3.60(2H,s),4.71(2H,s),7.04(2H, s),7.14(2H,s),7.20(3H,m),7.43(1H,m),7.54(5H,m),7.90(1H,s),8.86(1H,s)。
The preparation of the compound of embodiment 8 (40)
Preparation method is with reference to the 4) step of embodiment 1 the.White solid, fusing point is more than 250 DEG C.1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δppm1.15(3H,t),1.48(3H,t),2.16(6H,s),3.28(4H,m),4.12(2H,s),4.49 (2H,s),6.78(1H,s),7.13(3H,s),7.56(5H,m),8.02(1H,s),8.16(2H,d),8.39(1H,d),8.56 (1H,s)。
The preparation of the compound of embodiment 9 (41)
Preparation method is with reference to the 4) step of embodiment 1 the.White solid, 139 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, it is molten Agent CDCl3)δppm1.13(6H,t),2.16(6H,s),3.53(4H,m),3.58(2H,s),3.85(3H,s),4.73(2H, s),7.16(4H,d),7.33(2H,d),7.52(4H,m),8.53(1H,s)。
The preparation of the compound of embodiment 10 (73)
1) preparation of compound (VII-3)
By 12.1g2,6- dimethylanilines (0.1mol) are added in 500ml there-necked flasks, add 20.7g potassium carbonate (0.15mol), 200ml acetonitriles are stirred at room temperature lower dropwise addition 10g ethyl chloroacetates (0.083mol), are stirred at room temperature 2 hours, suction filtration, Filtrate precipitation obtains 13g crude products, is added into 150ml toluene, and 9.8g sodium carbonate (0.093mol) is dissolved in water and adds reaction In bottle, lower dropwise addition chloracetyl chloride is stirred at room temperature, is stirred at room temperature 2 hours, wash, organic layer precipitation is produced (VII-3).
The corresponding steps of remaining steps be the same as Example 1.Brown solid, 77 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, it is molten Agent CDCl3)δppm0.81(6H,d),1.22(6H,m),1.36(6H,s),2.01(1H,m),2.18(6H,m),2.72(2H, m),3.24(4H,m),4.07(4H,m),4.56(2H,s),7.01(1H,s),7.17(4H,m),7.51(4H,m),7.90(2H, s)。
The preparation of the compound of embodiment 11 (76)
Preparation method is with reference to the 4) step of embodiment 1 the.Yellow solid, 220.2 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, Solvent C DCl3) δ ppm1.33 (6H, t), 2.16 (6H, t), 3.20 (3H, t), 3.47 (4H, m), 3.85 (4H, d), 4.54 (6H, d),6.86(2H,s),7.25(4H,m),7.48(5H,s)。
The preparation of the compound of embodiment 12 (81)
Preparation method is with reference to the 4) step of embodiment 1 the.Gray solid, 91 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, it is molten Agent CDCl3)δppm1.16(6H,m),1.32(3H,t),2.21(6H,t),3.39(2H,m),3.50(2H,s),3.54(4H, m),3.64(2H,s),4.37(2H,d),6.92(1H,s),7.58(4H,m),7.61(4H,m),8.11(2H,d),8.45(2H, d)。
Biological activity determination
Herbicidal in the Room of embodiment 13
The testing compound active compound acetone solution that above-described embodiment is obtained, then diluted with the water containing 0.1% Tween 80 To required concentration.Quantitative weed seed is sowed in a diameter of 7cm dixie cup equipped with Nutrition Soil respectively, rear earthing is broadcast 1cm, suppression, after water drenching in hot-house culture, thinning after emerging, field planting (10-20 plants/cup of grassy weed, 2-4 plants of broad leaved weed/ Cup), treat the grassy weed 2-3 leaf phases, broad leaved weed length to 2-4 leaf periods, sprayed by experimental design dosage with crawler type crop Machine (Britain Engineer Research Ltd. designs production) carries out cauline leaf spraying treatment (atomisation pressure 1.95kg/cm2, spray Liquid measure 50mL/m2, crawler track speeds 1.48km/h).Experiment sets 3 repetitions.After after decoction natural air drying, it is placed in greenhouse routinely Method is managed, and routine observation tries the situation of growing of material, and according to actual conditions, reagent is supplied in periodical visual inspection investigation after processing Preventive effect of the agent to weeds.Preventive effect grade scale：0 is invalid, and 100 be to kill weeds completely or seriously suppress.
According to above method, the activity of weeding of part of compounds is shown in Table 2~table 3.The compounds of this invention seedling as can be seen from the table It is preceding to corn, cotton, after seedling is to wheat, corn safety.
General sieve activity of weeding (the dispenser dosage 1000g a.i./hm of the part of compounds of table 22)
The deep screening Herbicide activity data of the part of compounds of table 3

Claims (5)

1. a kind of quaternary ammonium compound, it is characterised in that：Quaternary ammonium compound is as shown in logical formula (I)：
In formula：
R1、R2、R3It may be the same or different and be respectively selected from hydrogen, halogen, methyl, ethyl, propyl group, isopropyl, cyclopropyl, the tert-butyl group, first Epoxide, trifluoromethoxy, difluoro-methoxy, trifluoromethyl or difluoromethyl；
R4、R5It may be the same or different and be respectively selected from hydrogen, methyl, ethyl or propyl group；
R6Selected from hydrogen, methyl, ethyl, propyl group, phenyl that is unsubstituted or being independently selected from following substituent group by 1-4：Halogen, Nitro, cyano group or C1-C3Alkyl；
R7Selected from hydrogen, (CH2)nCO2R8Or (CH2)nOR8；
N is selected from 0,1,2；
R8Selected from methyl or ethyl；
Q is selected from one of group as follows：
。
2. according to the compound described in claim 1, it is characterised in that：In logical formula (I)
R1、R2、R3It may be the same or different and be respectively selected from hydrogen, halogen, methyl or ethyl；
R4、R5It may be the same or different and be respectively selected from hydrogen, methyl or ethyl；
R6Selected from phenyl that is unsubstituted or being independently selected from following substituent group by 1-4：Halogen, nitro, cyano group or C1-C3Alkane Base；
R7Selected from hydrogen or (CH2)nCO2R8；
N is selected from 0 or 1；
R8Selected from methyl or ethyl；
Q is selected from Q1-4, Q2-1, Q2-2, Q2-3, Q3-7, Q3-8, Q6-1, Q6-2, Q8-1, Q8-2 or Q9-1.
3. according to the compound described in claim 2, it is characterised in that：In logical formula (I)
R1、R2It is respectively selected from methyl or ethyl；
R3Selected from hydrogen；
R4、R5It may be the same or different and be respectively selected from methyl or ethyl；
R6Selected from unsubstituted phenyl；
R7Selected from hydrogen or (CH2)nCO2R8；
N is selected from 1；
R8Selected from ethyl；
Q is selected from Q1-4, Q2-3, Q3-7, Q6-1, Q8-1 or Q9-1.
4. a kind of logical formula (I) compound according to claim 1 is used for the application for preparing weeds agent.
5. a kind of Herbicidal combinations, it is characterised in that：Active component, group are used as using the logical formula (I) compound described in claim 1 The weight percentage of active component in compound is 0.1-99%.
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