CN105566148A - Quaternary ammonium salt compound and application thereof - Google Patents
Quaternary ammonium salt compound and application thereof Download PDFInfo
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- CN105566148A CN105566148A CN201410539916.4A CN201410539916A CN105566148A CN 105566148 A CN105566148 A CN 105566148A CN 201410539916 A CN201410539916 A CN 201410539916A CN 105566148 A CN105566148 A CN 105566148A
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Abstract
Belonging to the field of agricultural herbicides, the invention in particular relates to a quaternary ammonium salt compound and application thereof. The quaternary ammonium salt compound is shown as general formula (I). The general formula (I) compound has very good herbicidal activity, can effectively control barnyard grass, Abutilon theophrasti, Green Bristlegrass Herb, Zinnia elegans and other weeds, can achieve a good weeding effect under a low dosage, and is safe to corn and cotton before emergence and safe to wheat and corn after emergence. (general formula (I)).
Description
Technical field
The invention belongs to field of agricultural herbicide, be specifically related to a kind of quaternary ammonium compound and application thereof.
Background technology
Patent EP0638843A2, US3080327A disclose the compound of following general formula, as photographic developer and Denatured alcohol additive.
X is the phenylformic acid etc. of halogen, hydroxyl and replacement.
Its Patent EP0638843A2 specification sheets page 5 discloses compd A (being numbered I-4 in patent).
In prior art, the compound as shown in general formula of the present invention (I) has no its weeding activity report.
Summary of the invention
In order to development of new weedicide is to solve day by day serious Herbicid resistant problem, the invention provides a kind of quaternary ammonium compound and application thereof.
For achieving the above object, the technical solution used in the present invention is:
The invention provides a kind of containing quaternary ammonium compound, as shown in general formula (I):
In formula:
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl, C
3-C
12cycloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12halogenated alkylthio, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
4, R
5may be the same or different and be selected from hydrogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl or C
3-C
12cycloalkyl;
R
6be selected from hydrogen, C
1-C
12alkyl, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
7be selected from hydrogen, C
1-C
12alkyl, C
1-C
12haloalkyl, (CH
2) nCO
2r
8or (CH
2) nOR
8;
N is selected from 0,1 or 2;
R
8be selected from C
1-C
12alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9:
R
9be selected from hydrogen, halogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12alkoxy C
1-C
12alkyl, C
2-C
12thiazolinyl, C
3-C
12cycloalkyl or C
1-C
12halogenated alkylthio;
R
10be selected from hydrogen, halogen, C
1-C
12alkyl, C
1-C
12alkoxyl group, C
2-C
12thiazolinyl, C
1-C
12haloalkyl or C
1-C
12halogenated alkoxy; Or R
9, R
10five-ring or six-ring can be formed;
R
11be selected from CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen or C respectively
1-C
12alkyl;
R
15, R
16, R
23, R
24be selected from hydrogen, halogen or C respectively
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12alkoxy C
1-C
12alkyl, C
2-C
12thiazolinyl, C
3-C
12cycloalkyl or C
1-C
12halogenated alkylthio; R
18be selected from C
1-C
12alkyl, C
1-C
12haloalkyl, unsubstituted or that be independently selected from following group replace by 1-4 phenyl, pyridyl, pyrimidyl, pyrazolyl, thiazolyl, quinolyl, benzoxazolyl or quinoxalinyl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
19, R
20, R
22be selected from hydrogen, halogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy;
R
21be selected from hydrogen, halogen or NH
2;
R
25be selected from hydrogen, halogen, nitro, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12alkoxy C
1-C
12alkyl, C
2-C
12thiazolinyl, C
3-C
12cycloalkyl or C
1-C
12halogenated alkylthio;
R
26, R
27what may be the same or different is selected from hydrogen, C respectively
1-C
12alkyl or C
1-C
12alkoxyl group;
R
28be selected from O or S;
R
29be selected from hydrogen, halogen, pyrimidyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
6alkyl or C
1-C
6alkoxyl group;
R
31be selected from halogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy;
R
32be selected from hydrogen, C
1-C
12alkyl, unsubstituted or by 1-4 be independently selected from following group replace pyridyl or phenyl: halogen, C
1-C
6alkyl or halo C
1-C
6alkyl.
R
33, R
34be selected from hydrogen, halogen, nitro, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy;
The more preferred compound of the present invention is: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl, C
3-C
12cycloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy or C
1-C
12halogenated alkylthio;
R
4, R
5may be the same or different and be selected from hydrogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl or C
3-C
12cycloalkyl;
R
6be selected from hydrogen, C
1-C
12alkyl, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
7be selected from hydrogen, C
1-C
12alkyl, C
1-C
12haloalkyl, (CH
2) nCO
2r
8or (CH
2) nOR
8;
N is selected from 0,1 or 2;
R
8be selected from C
1-C
12alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9;
R
9be selected from hydrogen, halogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12alkoxy C
1-C
12alkyl or C
2-C
12thiazolinyl;
R
10be selected from hydrogen, halogen, C
1-C
12alkyl or C
2-C
12thiazolinyl; Or R
9, R
10six-ring can be formed; R
11be selected from CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen or C respectively
1-C
12alkyl;
R
15, R
16, R
23, R
24be selected from hydrogen, halogen or C respectively
1-C
12alkyl;
R
18be selected from C
1-C
12alkyl, C
1-C
12haloalkyl, unsubstituted or that be independently selected from following group replace by 1-4 phenyl, pyridyl, quinolyl, benzoxazolyl or quinoxalinyl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
19, R
20, R
22be selected from hydrogen or halogen respectively;
R
21be selected from hydrogen, halogen or NH
2;
R
25be selected from hydrogen, halogen or nitro;
R
26, R
27what may be the same or different is selected from hydrogen, C respectively
1-C
12alkyl or C
1-C
12alkoxyl group;
R
28be selected from O or S;
R
29be selected from hydrogen, halogen, pyrimidyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
6alkyl or C
1-C
6alkoxyl group;
R
31be selected from halogen or C
1-C
12alkyl;
R
32be selected from hydrogen, C
1-C
12alkyl, pyridyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
6alkyl or halo C
1-C
6alkyl.
R
33, R
34be selected from hydrogen, halogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
12alkyl, C
1-C
12haloalkyl or C
1-C
12alkoxyl group;
The present invention more comparatively preferred compound is: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, C respectively
1-C
8alkyl, C
1-C
8haloalkyl, C
3-C
8cycloalkyl, C
1-C
8alkoxyl group, C
1-C
8halogenated alkoxy or C
1-C
8halogenated alkylthio;
R
4, R
5may be the same or different and be selected from hydrogen, C respectively
1-C
8alkyl, C
1-C
8haloalkyl or C
3-C
8cycloalkyl;
R
6be selected from hydrogen, C
1-C
8alkyl, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
7be selected from hydrogen, C
1-C
8alkyl, C
1-C
8haloalkyl, (CH
2)
ncO
2r
8or (CH
2)
noR
8;
N is selected from 0, and 1,2;
R
8be selected from C
1-C
8alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9;
R
9be selected from hydrogen, halogen, C
1-C
8alkyl, C
1-C
8haloalkyl, C
1-C
8alkoxyl group, C
1-C
8halogenated alkoxy, C
1-C
8alkoxy C
1-C
8alkyl or C
2-C
8thiazolinyl;
R
10be selected from hydrogen, halogen, C
1-C
8alkyl or C
2-C
8thiazolinyl; Or R
9, R
10six-ring can be formed;
R
11be selected from CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen or C respectively
1-C
8alkyl;
R
15, R
16, R
23, R
24be selected from hydrogen, halogen or C respectively
1-C
8alkyl;
R
18be selected from C
1-C
8alkyl, C
1-C
8haloalkyl, unsubstituted or that be independently selected from following group replace by 1-4 phenyl, pyridyl, quinolyl, benzoxazolyl or quinoxalinyl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
19, R
20, R
22be selected from hydrogen or halogen respectively;
R
21be selected from hydrogen, halogen or NH
2;
R
25be selected from hydrogen, halogen or nitro;
R
26, R
27what may be the same or different is selected from hydrogen, C respectively
1-C
8alkyl or C
1-C
8alkoxyl group;
R
28be selected from O or S;
R
29be selected from hydrogen, halogen, pyrimidyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
4alkyl or C
1-C
4alkoxyl group;
R
31be selected from halogen or C
1-C
8alkyl;
R
32be selected from hydrogen, C
1-C
8alkyl, pyridyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
6alkyl or halo C
1-C
6alkyl.
R
33, R
34be selected from hydrogen, halogen, C
1-C
8alkyl, C
1-C
8haloalkyl, C
1-C
8alkoxyl group or C
1-C
8halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
8alkyl, C
1-C
8haloalkyl or C
1-C
8alkoxyl group;
The present invention further preferred compound is: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, C respectively
1-C
6alkyl, C
1-C
6haloalkyl, C
3-C
6cycloalkyl, C
1-C
6alkoxyl group, C
1-C
6halogenated alkoxy or C
1-C
6halogenated alkylthio;
R
4, R
5may be the same or different and be selected from hydrogen, C respectively
1-C
6alkyl, C
1-C
6haloalkyl or C
3-C
6cycloalkyl;
R
6be selected from hydrogen, C
1-C
6alkyl, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
7be selected from hydrogen, C
1-C
6alkyl, C
1-C
6haloalkyl, (CH
2)
ncO
2r
8or (CH
2)
noR
8;
N is selected from 0, and 1,2;
R
8be selected from C
1-C
6alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9;
R
9be selected from hydrogen, halogen, C
1-C
6alkyl, C
1-C
6haloalkyl, C
1-C
6alkoxyl group, C
1-C
6halogenated alkoxy, C
1-C
6alkoxy C
1-C
6alkyl or C
2-C
6thiazolinyl;
R
10be selected from hydrogen, halogen, C
1-C
6alkyl or C
2-C
6thiazolinyl; Or R
9, R
10six-ring can be formed;
R
11be selected from CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen or C respectively
1-C
6alkyl;
R
15, R
16, R
23, R
24be selected from hydrogen, halogen or C respectively
1-C
6alkyl;
R
18be selected from C
1-C
6alkyl, C
1-C
6haloalkyl, unsubstituted or that be independently selected from following group replace by 1-4 phenyl, pyridyl, quinolyl, benzoxazolyl or quinoxalinyl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
19, R
20, R
22be selected from hydrogen or halogen respectively;
R
21be selected from hydrogen, halogen or NH
2;
R
25be selected from hydrogen, halogen or nitro;
R
26, R
27what may be the same or different is selected from hydrogen, C respectively
1-C
6alkyl or C
1-C
6alkoxyl group;
R
28be selected from O or S;
R
29be selected from hydrogen, halogen, pyrimidyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
4alkyl or C
1-C
4alkoxyl group;
R
31be selected from halogen or C
1-C
4alkyl;
R
32be selected from hydrogen, C
1-C
4alkyl, unsubstituted or by the pyridyl of 1-4 halogen substiuted.
R
33, R
34be selected from hydrogen, halogen, C
1-C
6alkyl, C
1-C
6haloalkyl, C
1-C
6alkoxyl group or C
1-C
6halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
6alkyl, C
1-C
6haloalkyl or C
1-C
6alkoxyl group;
The present invention further preferred compound is: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, methyl, ethyl, propyl group, sec.-propyl, cyclopropyl, the tertiary butyl, methoxyl group, trifluoromethoxy, difluoro-methoxy, trifluoromethyl or difluoromethyl respectively;
R
4, R
5may be the same or different and be selected from hydrogen, methyl, ethyl or propyl group respectively;
R
6be selected from hydrogen, methyl, ethyl, propyl group, butyl, phenyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, nitro, cyano group or C
1-C
3alkyl;
R
7be selected from hydrogen, (CH
2)
ncO
2r
8or (CH
2)
noR
8;
N is selected from 0, and 1,2;
R
8be selected from C
1-C
4alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9;
R
9be selected from hydrogen, fluorine, chlorine, methyl, ethyl, the tertiary butyl, trifluoromethyl, methoxyl group, trifluoromethoxy or methoxymethyl ether;
R
10be selected from hydrogen; Or R
9, R
10phenyl ring can be formed;
R
11be selected from CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen, methyl, ethyl, sec.-propyl or the tertiary butyl respectively;
R
15, R
16, R
23, R
24be selected from hydrogen, fluorine, chlorine, methyl, ethyl, sec.-propyl or the tertiary butyl respectively;
R
18be selected from methyl, ethyl, sec.-propyl, the tertiary butyl, trifluoromethyl, difluoromethyl, unsubstituted or that be independently selected from following group replace by 1-3 phenyl, pyridyl, quinolyl, benzoxazolyl or quinoxalinyl: fluorine, chlorine, nitro, cyano group, methyl, ethyl, the tertiary butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methoxyl group, trifluoromethoxy or difluoro-methoxy;
R
19, R
20, R
22be selected from hydrogen, fluorine or chlorine respectively;
R
21select NH
2;
R
25be selected from hydrogen, fluorine, chlorine or nitro;
R
26, R
27what may be the same or different is selected from hydrogen or methoxyl group respectively;
R
28be selected from O or S;
R
29be selected from hydrogen, fluorine, chlorine or 4,6-dimethoxy-2-pyrimidyl;
R
31be selected from halogen, methyl, ethyl, sec.-propyl or the tertiary butyl;
R
32be selected from hydrogen, methyl, ethyl, pyridyl that is unsubstituted or that replaced by 1-4 chlorine atom.
R
33, R
34be selected from hydrogen, halogen, C
1-C
4alkyl, C
1-C
4haloalkyl, C
1-C
4alkoxyl group or C
1-C
4halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
4alkyl, C
1-C
4haloalkyl or C
1-C
4alkoxyl group;
The present invention further preferred compound is: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, methyl, ethyl, propyl group, sec.-propyl, cyclopropyl, the tertiary butyl, methoxyl group, trifluoromethoxy, difluoro-methoxy, trifluoromethyl or difluoromethyl respectively;
R
4, R
5may be the same or different and be selected from hydrogen, methyl, ethyl or propyl group respectively;
R
6be selected from hydrogen, methyl, ethyl, propyl group, phenyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, nitro, cyano group or C
1-C
3alkyl;
R
7be selected from hydrogen, (CH
2)
ncO
2r
8or (CH
2)
noR
8;
N is selected from 0, and 1,2;
R
8be selected from methyl or ethyl.
Q is selected from one of group as follows:
The present invention more further preferred compound be: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, methyl or ethyl respectively;
R
4, R
5may be the same or different and be selected from hydrogen, methyl or ethyl respectively;
R
6be selected from phenyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, nitro, cyano group or C
1-C
3alkyl;
R
7be selected from hydrogen or (CH
2)
ncO
2r
8;
N is selected from 0 or 1;
R
8be selected 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 general formula (I)
R
1, R
2be selected from methyl or ethyl respectively;
R
3be selected from hydrogen;
R
4, R
5may be the same or different and be selected from methyl or ethyl respectively;
R
6be selected from unsubstituted phenyl;
R
7be selected from hydrogen or (CH
2)
ncO
2r
8;
N is selected from 1;
R
8be selected from ethyl;
Q is selected from Q1-4, Q2-3, Q3-7, Q6-1, Q8-1 or Q9-1.
In the definition of general formula (I) compound provided above, collect term used and be generally defined as follows:
Halogen: refer to fluorine, chlorine, bromine or iodine.Alkyl: straight or branched alkyl, such as methyl, ethyl, propyl group, sec.-propyl, normal-butyl or the tertiary butyl.Cycloalkyl: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl.Substituting group is as methyl, halogen etc.Haloalkyl: straight or branched alkyl, the hydrogen atom on these alkyl can partly or entirely replace by halogen atom, such as, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl etc.Alkoxyl group: straight or branched alkyl, is connected in structure through Sauerstoffatom key.Halogenated alkoxy: straight or branched alkoxyl group, the hydrogen atom on these alkoxyl groups can partly or entirely replace by halogen atom.Such as, chlorine methoxyl group, dichloro methoxyl group, trichloromethoxy, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group, trifluoro ethoxy etc.Halogenated alkylthio: straight or branched alkylthio, the hydrogen atom on these alkyl can partly or entirely replace by halogen atom.Such as, chloromethane sulfenyl, dichloromethane sulfenyl, trichloro-methylthio, fluorine methylthio group, difluoro methylthio group, trifluoromethylthio, chlorine fluorine methylthio group etc.Thiazolinyl: straight or branched alkene class, such as vinyl, 1-propenyl, 2-propenyl and different butenyls, pentenyl and hexenyl isomers.Thiazolinyl also comprises polyenoid class, as 1,2-propadiene base and 2,4-hexadienyl.Aryl: polynary aromatic group, as phenyl, naphthyl.Heteroaryl is containing the heteroatomic five-ring of one or more N, O, S or six-ring.Such as furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl etc.
Part of compounds of the present invention can illustrate by the particular compound listed in table 1, but the present invention is not limited in these compounds.
Wherein R
3=H, R
6=Ph
Table 1
| Numbering | R 1 | R 2 | R 4 | R 5 | R 7 | Q |
| 1 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q1-4 |
| 2 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q2-1 |
| 3 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q2-2 |
| 4 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q2-3 |
| 5 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q3-7 |
| 6 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q3-8 |
| 7 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q6-1 |
| 8 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q6-2 |
| 9 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q8-1 |
| 10 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q8-2 |
| 11 | CH 3 | CH 3 | CH 3 | CH 3 | H | Q9-1 |
| 12 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q1-4 |
| 13 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q2-1 |
| 14 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q2-2 |
| 15 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q2-3 |
| 16 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q3-7 |
| 17 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q3-8 |
| 18 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q6-1 |
| 19 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q6-2 |
| 20 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q8-1 |
| 21 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | H | Q9-1 |
| 22 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q1-4 |
| 23 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q2-1 |
| 24 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q2-2 |
| 25 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q2-3 |
| 26 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q3-7 |
| 27 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q3-8 |
| 28 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q6-1 |
| 29 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q6-2 |
| 30 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q8-1 |
| 31 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q9-1 |
| 32 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q1-4 |
| 33 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q2-1 |
| 34 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q2-2 |
| 35 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q2-3 |
| 36 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q3-7 |
| 37 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q3-8 |
| 38 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q6-1 |
| 39 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q6-2 |
| 40 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q8-1 |
| 41 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | H | Q9-1 |
| 42 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q1-4 |
| 43 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q2-1 |
| 44 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q2-2 |
| 45 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q2-3 |
| 46 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q3-7 |
| 47 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q3-8 |
| 48 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q6-1 |
| 49 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q6-2 |
| 50 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q8-1 |
| 51 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q8-2 |
| 52 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q9-1 |
| 53 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q1-4 |
| 54 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q2-1 |
| 55 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q2-2 |
| 56 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q2-3 |
| 57 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q3-7 |
| 58 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q3-8 |
| 59 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q6-1 |
| 60 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q6-2 |
| 61 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q8-1 |
| 62 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2CO 2C 2H 5 | Q9-1 |
| 63 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q1-4 |
| 64 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q2-1 |
| 65 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q2-2 |
| 66 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q2-3 |
| 67 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q3-7 |
| 68 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q3-8 |
| 69 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q6-1 |
| 70 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q6-2 |
| 71 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q8-1 |
| 72 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q9-1 |
| 73 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q1-4 |
| 74 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q2-1 |
| 75 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q2-2 |
| 76 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q2-3 |
| 77 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q3-7 |
| 78 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q3-8 |
| 79 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q6-1 |
| 80 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q6-2 |
| 81 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q8-1 |
| 82 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CO 2C 2H 5 | Q9-1 |
| 83 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q1-4 |
| 84 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q2-1 |
| 85 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q2-2 |
| 86 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q2-3 |
| 87 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q3-7 |
| 88 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q3-8 |
| 89 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q6-1 |
| 90 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q6-2 |
| 91 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q8-1 |
| 92 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q8-2 |
| 93 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q9-1 |
| 94 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q1-4 |
| 95 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q2-1 |
| 96 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q2-2 |
| 97 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q2-3 |
| 98 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q3-7 |
| 99 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q3-8 |
| 100 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q6-1 |
| 101 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q6-2 |
| 102 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q8-1 |
| 103 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OC 2H 5 | Q9-1 |
| 104 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q1-4 |
| 105 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q2-1 |
| 106 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q2-2 |
| 107 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q2-3 |
| 108 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q3-7 |
| 109 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q3-8 |
| 110 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q6-1 |
| 111 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q6-2 |
| 112 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q8-1 |
| 113 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q9-1 |
| 114 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q1-4 |
| 115 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q2-1 |
| 116 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q2-2 |
| 117 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q2-3 |
| 118 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q3-7 |
| 119 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q3-8 |
| 120 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q6-1 |
| 121 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q6-2 |
| 122 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q8-1 |
| 123 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OC 2H 5 | Q9-1 |
| 124 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q1-4 |
| 125 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q2-1 |
| 126 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q2-2 |
| 127 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q2-3 |
| 128 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q3-7 |
| 129 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q3-8 |
| 130 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q6-1 |
| 131 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q6-2 |
| 132 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q8-1 |
| 133 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q8-2 |
| 134 | CH 3 | CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q9-1 |
| 135 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q1-4 |
| 136 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q2-1 |
| 137 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q2-2 |
| 138 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q2-3 |
| 139 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q3-7 |
| 140 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q3-8 |
| 141 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q6-1 |
| 142 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q6-2 |
| 143 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q8-1 |
| 144 | CH 2CH 3 | CH 2CH 3 | CH 3 | CH 3 | CH 2OCH 3 | Q9-1 |
| 145 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q1-4 |
| 146 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q2-1 |
| 147 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q2-2 |
| 148 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q2-3 |
| 149 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q3-7 |
| 150 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q3-8 |
| 151 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q6-1 |
| 152 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q6-2 |
| 153 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q8-1 |
| 154 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q9-1 |
| 155 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q1-4 |
| 156 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q2-1 |
| 157 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q2-2 |
| 158 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q2-3 |
| 159 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q3-7 |
| 160 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q3-8 |
| 161 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q6-1 |
| 162 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q6-2 |
| 163 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q8-1 |
| 164 | CH 3 | CH 3 | CH 2CH 3 | CH 2CH 3 | CH 2OCH 3 | Q9-1 |
General formula of the present invention (I) compound can be prepared by the following method, and outside indicating, in reaction formula, each group definition is the same.
General formula (I) compound can be obtained by the sour condensation shown in the villaumite shown in general formula (II) and general formula (III).
React and carry out in suitable solvent, suitable solvent can be selected from benzene,toluene,xylene, acetone, tetrahydrofuran (THF), acetonitrile, DMF, N-Methyl pyrrolidone, methylene dichloride, chloroform, ethylene dichloride or ethyl acetate, methyl alcohol, ethanol etc.Reaction can be carried out under having alkali or alkali-free to exist, and when reacting under having alkali to exist, can accelerated reaction carry out.Described alkali can be selected from alkalimetal hydride, as sodium hydride; Alkali metal hydroxide, as sodium hydroxide or potassium hydroxide; Alkaline carbonate, as sodium carbonate or salt of wormwood; Organic bases, as pyridine, DMAP, triethylamine, N-methylpyrrole or diisopropyl ethyl amine etc.Between the suitable solvent boiling point temperature that temperature of reaction is selected in extremely can reacting at-10 DEG C, be generally 0 ~ 100 DEG C.Reaction times is 30 minutes to 20 hours, usual 1 ~ 10 hour.
Compound shown in general formula (II) can be obtained by currently known methods, specifically see US3080327A: preparation process is, by (IV) and (V) in suitable solvent or frit reaction generate (II).Suitable solvent can be selected from methylene dichloride, chloroform, tetracol phenixin, sherwood oil or toluene, dimethylbenzene etc.Temperature of reaction between room temperature to suitable solvent boiling point temperature, can be generally 20 ~ 200 DEG C.Reaction times is 30 minutes to 30 hours, usual 5 ~ 24 hours.(V) the benzyl chlorine shown in all has commercially available.
Compound shown in general formula (IV) can be obtained by currently known methods, specifically see US3080327A.
Compound of the present invention can control the weeds such as barnyard grass, youth-and-old-age, Herba Setariae Viridis, piemarker effectively, under low dosage, just can obtain good effect.Good to crop safety, especially to corn safety, agriculturally can be used as weedicide.Therefore the present invention also comprises general formula (I) compound for controlling the purposes of weeds.
Present invention also offers a kind of herbicidal composition, said composition is using general formula (I) compound as active ingredient, and the weight percentage of the active ingredient in composition is 0.1-99%.Therefore the present invention also comprises said composition for controlling the purposes of weeds.
Composition of the present invention can adopt the known method of those skilled in the art to prepare corresponding formulation.Active ingredient can contain the mixture of single compound of the present invention or several compound.
Carrier system in the present composition meets the material of following condition: it and activeconstituents are convenient to be applied to pending site after preparing, such as, can be plant, seed or soil; Or be conducive to storage, transport or operation.Carrier can be solid or liquid, comprises and is generally gas but the material being compressed into liquid, and in preparation herbicidal composition, carrier used all can use usually.
Suitable solid carrier comprises clay and silicate (such as diatomite, talcum, attapulgite, pure aluminium silicate (kaolin), montmorillonite and the mica of natural synthesis; ), calcium carbonate, calcium sulfate, ammonium sulfate, the silicon oxide of synthesis, synthetic calcium silicate, synthetic aluminium silicate, natural resin, synthesis resin (natural resin, the resin of synthesis are as coumarone resin, polyvinyl chloride and styrene polymer and multipolymer), solid polystream phenol, pitch or wax (as beeswax, paraffin).
Suitable liquid vehicle comprises water; Alcohol is (as Virahol and ethanol; Ketone is as acetone, methyl ethyl ketone, methyl isopropyl Ketone, cyclohexyl ketone), the mixing of one or more in ether, aromatic hydrocarbons (as benzene,toluene,xylene), petroleum fractions (as kerosene and mineral oil), hydrochloric ether (as tetracol phenixin, tetrachloroethylene and trieline).
Composition is usually processed into the form of enriched material and with this for transport, is diluted before administration by user.Having of a small amount of supporting surfactant helps dilution.Like this, according to having at least a kind of carrier to be preferably tensio-active agent in composition of the present invention.Such as composition can contain at least two kinds of carriers, and wherein at least one is tensio-active agent.
Tensio-active agent can be emulsifying agent, dispersion agent or wetting agent; It can be tensio-active agent that is non-ionic or ion.The example of suitable tensio-active agent comprises sodium salt or the calcium salt of polyacrylic acid and lignosulfonic acid; Containing the lipid acid of at least 12 carbon atoms or the condenses of aliphatic amide or acid amides and oxyethane and/or propylene oxide in molecule.The condenses of glycol, sorbyl alcohol, sucrose or pentaerythritol fatty ester and these esters and oxyethane and/or propylene oxide; Fatty alcohol or alkylphenol are as paraoctyl phenol or the condenses to octyl group cresylol and oxyethane and/or propylene oxide; The vitriol of these condensation products and sulfonate; In the molecule at least containing the sulfuric acid of 10 carbon atoms or the basic metal of sulphonate or alkaline earth salt, particular certain cancers, such as sulfuric acid laurate sodium, the secondary alkyl ester sodium of sulfuric acid, sulfonated castor oil sodium salt, alkyl aryl sulfonic acid ester sodium, as pelopon A.
The example of composition of the present invention is wettable powder, pulvis, granule, aqua, emulsible enriching agent, emulsion, aerosol and smoke substance.Wettable powder usually containing the activeconstituents of 25-75% weight, and usually except solid inert carrier except, also contains the dispersion agent of 3-10% weight, and if desired can add the stablizer of 0-10% weight and/or other additive as permeate agent or tackiness agent.Pulvis can be usually has the composition similar to wettable powder but the pulvis enriching agent not having dispersion agent, more further with solid carrier dilution, obtains usually containing the composition of the activeconstituents of 0.5-10% weight.Granula is prepared into usually has 10 to 100 orders (1.676-0.152mm) size, and available agglomerating or implantttion technique preparation.Usual granula is containing the activeconstituents of 0.5-75% weight and the additive (additive is as stablizer, tensio-active agent or slowly-releasing modifying agent) of 0-10% weight.Can emulsion concentrate in addition to the solvents, when needed usually containing cosolvent, 1-50%W/V activeconstituents, 2-20%W/V emulsifying agent and other additive of 0-20%W/V (additive is as stablizer, permeate agent or corrosion inhibitor).Suspension enriching agent activeconstituents, the dispersion agent of 0.5-15% weight, other additive (additive is as defoamer, corrosion inhibitor, stablizer, permeate agent and tackiness agent) of 0.1-10% weight usually containing 10-75% weight.
Water dispersant and emulsion, such as, by the composition that dilute with water obtains according to wettable powder of the present invention or enriched material, also list the scope of the invention in.Said emulsion can have water-in-oil or oil-in-water two types.
By adding other one or more weedicides in the composition, the activity of more wide spectrum can be had than independent general formula (I) compound.In addition, other weedicide the weeding activity of mutual-through type (I) compound can have synergism, also can by general formula (I) compound and other herbicide mixture, in mixture, the content scope of effective constituent is very large, in mixture, active constituent content is generally at 1%-95%, and comparatively suitable content is at 5%-60%.
The advantage that the present invention has: adopt general formula of the present invention (I) compound as the composition of active ingredient, effectively can control weeds, this compounds can effectively control the weeds such as barnyard grass, piemarker, Herba Setariae Viridis, youth-and-old-age as weedicide, and to corn, cotton before seedling, to wheat, corn safety after seedling, agriculturally can be used as weedicide.
Embodiment
Following specific embodiment is used for further illustrating the present invention, but the present invention is limited to absolutely not these examples.(except as otherwise indicate outside, raw materials used all have commercially available)
Synthetic example
The preparation of embodiment 1 compound (63)
1) preparation of intermediate (VII-1)
By soluble in water for 10g sodium carbonate (0.1mol), 200ml toluene is added after dissolving, add 10g2,6-Diethyl Aniline (0.068mol), under ice bath, drip 7.7g chloroacetyl chloride (0.068mol), stirring at room temperature 2 hours, TLC monitoring reaction is complete, reaction mixture suction filtration, washing, sherwood oil is washed, and obtains pink solid (VII-1).Fusing point 122-124 DEG C
2) preparation of intermediate (IV-1)
13g (VII-1) (0.058mol) is added 500ml there-necked flask, add 200ml acetonitrile, add 12g salt of wormwood (0.087mol), drip 4.2g diethylamine (0.058mol), reflux 3 hours, solution becomes pale yellow muddiness.After reacting completely, reaction mixture suction filtration, filtrate precipitation obtains yellow solid (IV-1).Fusing point 78-80 DEG C.
3) preparation of intermediate (II-1)
11g (IV-1) (0.042mol) is added 250ml bottle, adds 5.3g (V-1), add 25ml toluene, back flow reaction 24 hours.Have a small amount of solid to separate out after cooling, add ethyl acetate backflow 1 hour, solution becomes white opacity, and suction filtration after cooling, obtains white solid (II-1), fusing point 174-176 DEG C.
4) preparation of compound (63)
0.1g potassium hydroxide (0.0018mol) is dissolved in 25ml methyl alcohol, add 0.7g (II-1) (0.0018mol), stirring at room temperature 1 hour, suction filtration, filtering Repone K, 0.5g (III-1) (0.0018mol) is added filtrate, reflux 10 minutes, precipitation, adds 10ml ether, stirring at room temperature adularescent solid generates, suction filtration.Fusing point 168 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm0.86 (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 embodiment 2 compound (15)
Preparation method is with reference to embodiment 1 the 4th) step.White solid, fusing point 230.5 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.07 (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 embodiment 3 compound (31)
Preparation method is with reference to embodiment 1 the 4th) step.White solid, fusing point 165 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.12 (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 embodiment 4 compound (32)
Preparation method is with embodiment 1.White solid, fusing point 171 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm0.78 (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 embodiment 5 compound (35)
Preparation method is with reference to embodiment 1 the 4th) step.White solid, fusing point 185.3 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.47 (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 embodiment 6 compound (36)
Preparation method is with reference to embodiment 1 the 4th) step.Red solid, fusing point 93 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.20 (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 embodiment 7 compound (38)
Preparation method is with reference to embodiment 1 the 4th) step.Gray solid, fusing point 116.2 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.47 (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 embodiment 8 compound (40)
Preparation method is with reference to embodiment 1 the 4th) step.White solid, fusing point is greater than 250 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.15 (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 embodiment 9 compound (41)
Preparation method is with reference to embodiment 1 the 4th) step.White solid, fusing point 139 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.13 (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 embodiment 10 compound (73)
1) preparation of compound (VII-3)
By 12.1g2,6-xylidine (0.1mol) adds in 500ml there-necked flask, add 20.7g salt of wormwood (0.15mol), 200ml acetonitrile, 10g ethyl chloroacetate (0.083mol) is dripped under stirring at room temperature, stirring at room temperature 2 hours, suction filtration, filtrate precipitation obtains the thick product of 13g, is added 150ml toluene, and being dissolved in water by 9.8g sodium carbonate (0.093mol) adds in reaction flask, chloroacetyl chloride is dripped under stirring at room temperature, stirring at room temperature 2 hours, washing, namely organic layer precipitation obtains (VII-3).
Remaining steps is with embodiment 1 corresponding steps.Brown solid, fusing point 77 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm0.81 (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 embodiment 11 compound (76)
Preparation method is with reference to embodiment 1 the 4th) step.Yellow solid, fusing point 220.2 DEG C.1H-NMR (300MHz, interior mark 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 embodiment 12 compound (81)
Preparation method is with reference to embodiment 1 the 4th) step.Gray solid, fusing point 91 DEG C.1H-NMR (300MHz, interior mark TMS, solvent C DCl
3) δ ppm1.16 (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
The indoor Herbicidal of embodiment 13
The former medicinal acetone solution of testing compound that above-described embodiment obtains, then be diluted to required concentration with the water containing 0.1% tween 80.Quantitative weed seed is sowed at respectively diameter be 7cm be equipped with in the dixie cup of Nutrition Soil, broadcast rear earthing 1cm, in hot-house culture after suppression, trickle, thinning after emerging, field planting (gramineous weeds 10-20 strain/cup, broadleaf weeds 2-4 strain/cup), treat the gramineous weeds 2-3 leaf phase, broadleaf weeds grows to 2-4 leaf period, carries out cauline leaf spraying process (spray pressure 1.95kg/cm by test design dosage track type crops sprayer (Britain EngineerResearchLtd. designs production)
2, spouting liquid 50mL/m
2, crawler track speeds 1.48km/h).3 repetitions are established in test.After liquid natural air drying, be placed in greenhouse and manage according to a conventional method, the situation of growing of routine observation examination material, and according to practical situation, periodical visual inspection investigation reagent agent is to the preventive effect of weeds after process.Preventive effect grade scale: 0 is invalid, 100 for killing weeds completely or seriously suppressing.
According to above method, the weeding activity of part of compounds is in table 2 ~ table 3.By before the compounds of this invention seedling visible in table to corn, cotton, to wheat, corn safety after seedling.
General sieve weeding activity (the dispenser dosage 1000ga.i./hm of table 2 part of compounds
2)
The deep screening Herbicide activity data of table 3 part of compounds
Claims (10)
1. a quaternary ammonium compound, is characterized in that: quaternary ammonium compound is as shown in general formula (I):
In formula:
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl, C
3-C
12cycloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12halogenated alkylthio, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
4, R
5may be the same or different and be selected from hydrogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl or C
3-C
12cycloalkyl;
R
6be selected from hydrogen, C
1-C
12alkyl, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
7be selected from hydrogen, C
1-C
12alkyl, C
1-C
12haloalkyl, (CH
2) nCO
2r
8or (CH
2) nOR
8;
N is selected from 0,1 or 2;
R
8be selected from C
1-C
12alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9:
R
9be selected from hydrogen, halogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12alkoxy C
1-C
12alkyl, C
2-C
12thiazolinyl, C
3-C
12cycloalkyl or C
1-C
12halogenated alkylthio;
R
10be selected from hydrogen, halogen, C
1-C
12alkyl, C
1-C
12alkoxyl group, C
2-C
12thiazolinyl, C
1-C
12haloalkyl or C
1-C
12halogenated alkoxy; Or R
9, R
10five-ring or six-ring can be formed;
R
11be selected from CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen or C respectively
1-C
12alkyl;
R
15, R
16, R
23, R
24be selected from hydrogen, halogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12alkoxy C
1-C
12alkyl, C
2-C
12thiazolinyl, C
3-C
12cycloalkyl or C
1-C
12halogenated alkylthio;
R
18be selected from C
1-C
12alkyl, C
1-C
12haloalkyl, unsubstituted or that be independently selected from following group replace by 1-4 phenyl, pyridyl, pyrimidyl, pyrazolyl, thiazolyl, quinolyl, benzoxazolyl or quinoxalinyl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
19, R
20, R
22be selected from hydrogen, halogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy;
R
21be selected from hydrogen, halogen or NH
2;
R
25be selected from hydrogen, halogen, nitro, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12alkoxy C
1-C
12alkyl, C
2-C
12thiazolinyl, C
3-C
12cycloalkyl or C
1-C
12halogenated alkylthio;
R
26, R
27what may be the same or different is selected from hydrogen, C respectively
1-C
12alkyl or C
1-C
12alkoxyl group;
R
28be selected from O or S;
R
29be selected from hydrogen, halogen, pyrimidyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
6alkyl or C
1-C
6alkoxyl group;
R
31be selected from halogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy;
R
32be selected from hydrogen, C
1-C
12alkyl, unsubstituted or by 1-4 be independently selected from following group replace pyridyl or phenyl: halogen, C
1-C
6alkyl or halo C
1-C
6alkyl;
R
33, R
34be selected from hydrogen, halogen, nitro, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy.
2. according to compound according to claim 1, it is characterized in that: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl, C
3-C
12cycloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy or C
1-C
12halogenated alkylthio;
R
4, R
5may be the same or different and be selected from hydrogen, C respectively
1-C
12alkyl, C
1-C
12haloalkyl or C
3-C
12cycloalkyl;
R
6be selected from hydrogen, C
1-C
12alkyl, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
7be selected from hydrogen, C
1-C
12alkyl, C
1-C
12haloalkyl, (CH
2) nCO
2r
8or (CH
2) nOR
8;
N is selected from 0,1 or 2;
R
8be selected from C
1-C
12alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9;
R
9be selected from hydrogen, halogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group, C
1-C
12halogenated alkoxy, C
1-C
12alkoxy C
1-C
12alkyl or C
2-C
12thiazolinyl;
R
10be selected from hydrogen, halogen, C
1-C
12alkyl or C
2-C
12thiazolinyl; Or R
9, R
10six-ring can be formed; R
11be selected from
CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen or C respectively
1-C
12alkyl;
R
15, R
16, R
23, R
24be selected from hydrogen, halogen or C respectively
1-C
12alkyl;
R
18be selected from C
1-C
12alkyl, C
1-C
12haloalkyl, unsubstituted or that be independently selected from following group replace by 1-4 phenyl, pyridyl, quinolyl, benzoxazolyl or quinoxalinyl: halogen, nitro, cyano group, C
1-C
6alkyl, halo C
1-C
6alkyl, C
1-C
6alkoxyl group or halo C
1-C
6alkoxyl group;
R
19, R
20, R
22be selected from hydrogen or halogen respectively;
R
21be selected from hydrogen, halogen or NH
2;
R
25be selected from hydrogen, halogen or nitro;
R
26, R
27what may be the same or different is selected from hydrogen, C respectively
1-C
12alkyl or C
1-C
12alkoxyl group;
R
28be selected from O or S;
R
29be selected from hydrogen, halogen, pyrimidyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
6alkyl or C
1-C
6alkoxyl group;
R
31be selected from halogen or C
1-C
12alkyl;
R
32be selected from hydrogen, C
1-C
12alkyl, pyridyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
6alkyl or halo C
1-C
6alkyl;
R
33, R
34be selected from hydrogen, halogen, C
1-C
12alkyl, C
1-C
12haloalkyl, C
1-C
12alkoxyl group or C
1-C
12halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
12alkyl, C
1-C
12haloalkyl or C
1-C
12alkoxyl group.
3. according to compound according to claim 2, it is characterized in that: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, C respectively
1-C
8alkyl, C
1-C
8haloalkyl, C
3-C
8cycloalkyl, C
1-C
8alkoxyl group, C
1-C
8halogenated alkoxy or C
1-C
8halogenated alkylthio;
R
4, R
5may be the same or different and be selected from hydrogen, C respectively
1-C
8alkyl, C
1-C
8haloalkyl or C
3-C
8cycloalkyl;
R
6be selected from hydrogen, C
1-C
8alkyl, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
7be selected from hydrogen, C
1-C
8alkyl, C
1-C
8haloalkyl, (CH
2)
ncO
2r
8or (CH
2)
noR
8;
N is selected from 0, and 1,2;
R
8be selected from C
1-C
8alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9;
R
9be selected from hydrogen, halogen, C
1-C
8alkyl, C
1-C
8haloalkyl, C
1-C
8alkoxyl group, C
1-C
8halogenated alkoxy, C
1-C
8alkoxy C
1-C
8alkyl or C
2-C
8thiazolinyl;
R
10be selected from hydrogen, halogen, C
1-C
8alkyl or C
2-C
8thiazolinyl; Or R
9, R
10six-ring can be formed;
R
11be selected from CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen or C respectively
1-C
8alkyl;
R
15, R
16, R
23, R
24be selected from hydrogen, halogen or C respectively
1-C
8alkyl;
R
18be selected from C
1-C
8alkyl, C
1-C
8haloalkyl, unsubstituted or that be independently selected from following group replace by 1-4 phenyl, pyridyl, quinolyl, benzoxazolyl or quinoxalinyl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
19, R
20, R
22be selected from hydrogen or halogen respectively;
R
21be selected from hydrogen, halogen or NH
2;
R
25be selected from hydrogen, halogen or nitro;
R
26, R
27what may be the same or different is selected from hydrogen, C respectively
1-C
8alkyl or C
1-C
8alkoxyl group;
R
28be selected from O or S;
R
29be selected from hydrogen, halogen, pyrimidyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
4alkyl or C
1-C
4alkoxyl group;
R
31be selected from halogen or C
1-C
8alkyl;
R
32be selected from hydrogen, C
1-C
8alkyl, pyridyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
6alkyl or halo C
1-C
6alkyl;
R
33, R
34be selected from hydrogen, halogen, C
1-C
8alkyl, C
1-C
8haloalkyl, C
1-C
8alkoxyl group or C
1-C
8halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
8alkyl, C
1-C
8haloalkyl or C
1-C
8alkoxyl group.
4. according to compound according to claim 3, it is characterized in that: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, C respectively
1-C
6alkyl, C
1-C
6haloalkyl, C
3-C
6cycloalkyl, C
1-C
6alkoxyl group, C
1-C
6halogenated alkoxy or C
1-C
6halogenated alkylthio;
R
4, R
5may be the same or different and be selected from hydrogen, C respectively
1-C
6alkyl, C
1-C
6haloalkyl or C
3-C
6cycloalkyl;
R
6be selected from hydrogen, C
1-C
6alkyl, unsubstituted or that be independently selected from following group replace by 1-4 aryl, heteroaryl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
7be selected from hydrogen, C
1-C
6alkyl, C
1-C
6haloalkyl, (CH
2)
ncO
2r
8or (CH
2)
noR
8;
N is selected from 0, and 1,2;
R
8be selected from C
1-C
6alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9;
R
9be selected from hydrogen, halogen, C
1-C
6alkyl, C
1-C
6haloalkyl, C
1-C
6alkoxyl group, C
1-C
6halogenated alkoxy, C
1-C
6alkoxy C
1-C
6alkyl or C
2-C
6thiazolinyl;
R
10be selected from hydrogen, halogen, C
1-C
6alkyl or C
2-C
6thiazolinyl; Or R
9, R
10six-ring can be formed;
R
11be selected from CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen or C respectively
1-C
6alkyl;
R
15, R
16, R
23, R
24be selected from hydrogen, halogen or C respectively
1-C
6alkyl;
R
18be selected from C
1-C
6alkyl, C
1-C
6haloalkyl, unsubstituted or that be independently selected from following group replace by 1-4 phenyl, pyridyl, quinolyl, benzoxazolyl or quinoxalinyl: halogen, nitro, cyano group, C
1-C
4alkyl, halo C
1-C
4alkyl, C
1-C
4alkoxyl group or halo C
1-C
4alkoxyl group;
R
19, R
20, R
22be selected from hydrogen or halogen respectively;
R
21be selected from hydrogen, halogen or NH
2;
R
25be selected from hydrogen, halogen or nitro;
R
26, R
27what may be the same or different is selected from hydrogen, C respectively
1-C
6alkyl or C
1-C
6alkoxyl group;
R
28be selected from O or S;
R
29be selected from hydrogen, halogen, pyrimidyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, C
1-C
4alkyl or C
1-C
4alkoxyl group;
R
31be selected from halogen or C
1-C
4alkyl;
R
32be selected from hydrogen, C
1-C
4alkyl, unsubstituted or by the pyridyl of 1-4 halogen substiuted;
R
33, R
34be selected from hydrogen, halogen, C
1-C
6alkyl, C
1-C
6haloalkyl, C
1-C
6alkoxyl group or C
1-C
6halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
6alkyl, C
1-C
6haloalkyl or C
1-C
6alkoxyl group.
5. according to compound according to claim 4, it is characterized in that: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, methyl, ethyl, propyl group, sec.-propyl, cyclopropyl, the tertiary butyl, methoxyl group, trifluoromethoxy, difluoro-methoxy, trifluoromethyl or difluoromethyl respectively;
R
4, R
5may be the same or different and be selected from hydrogen, methyl, ethyl or propyl group respectively;
R
6be selected from hydrogen, methyl, ethyl, propyl group, butyl, phenyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, nitro, cyano group or C
1-C
3alkyl;
R
7be selected from hydrogen, (CH
2)
ncO
2r
8or (CH
2)
noR
8;
N is selected from 0, and 1,2;
R
8be selected from C
1-C
4alkyl;
Q is selected from one of group shown in following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9;
R
9be selected from hydrogen, fluorine, chlorine, methyl, ethyl, the tertiary butyl, trifluoromethyl, methoxyl group, trifluoromethoxy or methoxymethyl ether;
R
10be selected from hydrogen; Or R
9, R
10phenyl ring can be formed;
R
11be selected from CH or N;
R
12, R
13, R
14, R
17, R
30be selected from hydrogen, halogen, methyl, ethyl, sec.-propyl or the tertiary butyl respectively;
R
15, R
16, R
23, R
24be selected from hydrogen, fluorine, chlorine, methyl, ethyl, sec.-propyl or the tertiary butyl respectively;
R
18be selected from methyl, ethyl, sec.-propyl, the tertiary butyl, trifluoromethyl, difluoromethyl, unsubstituted or that be independently selected from following group replace by 1-3 phenyl, pyridyl, quinolyl, benzoxazolyl or quinoxalinyl: fluorine, chlorine, nitro, cyano group, methyl, ethyl, the tertiary butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methoxyl group, trifluoromethoxy or difluoro-methoxy;
R
19, R
20, R
22be selected from hydrogen, fluorine or chlorine respectively;
R
21select NH
2;
R
25be selected from hydrogen, fluorine, chlorine or nitro;
R
26, R
27what may be the same or different is selected from hydrogen or methoxyl group respectively;
R
28be selected from O or S;
R
29be selected from hydrogen, fluorine, chlorine or 4,6-dimethoxy-2-pyrimidyl;
R
31be selected from halogen, methyl, ethyl, sec.-propyl or the tertiary butyl;
R
32be selected from hydrogen, methyl, ethyl, pyridyl that is unsubstituted or that replaced by 1-4 chlorine atom;
R
33, R
34be selected from hydrogen, halogen, C
1-C
4alkyl, C
1-C
4haloalkyl, C
1-C
4alkoxyl group or C
1-C
4halogenated alkoxy;
R
35be selected from hydrogen, C
1-C
4alkyl, C
1-C
4haloalkyl or C
1-C
4alkoxyl group.
6. according to compound according to claim 5, it is characterized in that: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, methyl, ethyl, propyl group, sec.-propyl, cyclopropyl, the tertiary butyl, methoxyl group, trifluoromethoxy, difluoro-methoxy, trifluoromethyl or difluoromethyl respectively;
R
4, R
5may be the same or different and be selected from hydrogen, methyl, ethyl or propyl group respectively;
R
6be selected from hydrogen, methyl, ethyl, propyl group, phenyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, nitro, cyano group or C
1-C
3alkyl;
R
7be selected from hydrogen, (CH
2)
ncO
2r
8or (CH
2)
noR
8;
N is selected from 0, and 1,2;
R
8be selected from methyl or ethyl;
Q is selected from one of group as follows:
7. according to compound according to claim 6, it is characterized in that: in general formula (I)
R
1, R
2, R
3may be the same or different and be selected from hydrogen, halogen, methyl or ethyl respectively;
R
4, R
5may be the same or different and be selected from hydrogen, methyl or ethyl respectively;
R
6be selected from phenyl that is unsubstituted or that be independently selected from following group replace by 1-4: halogen, nitro, cyano group or C
1-C
3alkyl;
R
7be selected from hydrogen or (CH
2)
ncO
2r
8;
N is selected from 0 or 1;
R
8be selected 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.
8. according to compound according to claim 7, it is characterized in that: in general formula (I)
R
1, R
2be selected from methyl or ethyl respectively;
R
3be selected from hydrogen;
R
4, R
5may be the same or different and be selected from methyl or ethyl respectively;
R
6be selected from unsubstituted phenyl;
R
7be selected from hydrogen or (CH
2)
ncO
2r
8;
N is selected from 1;
R
8be selected from ethyl;
Q is selected from Q1-4, Q2-3, Q3-7, Q6-1, Q8-1 or Q9-1.
9. general formula according to claim 1 (I) compound is for the preparation of the application of weeds agent.
10. a herbicidal composition, is characterized in that: using general formula according to claim 1 (I) compound as active ingredient, and the weight percentage of the active ingredient in composition is 0.1-99%.
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| CN112079742A (en) * | 2020-09-04 | 2020-12-15 | 山东诚汇双达药业有限公司 | Method for preparing lidocaine through continuous reaction |
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| CN113979880A (en) * | 2021-11-15 | 2022-01-28 | 上海农帆生物科技有限公司 | Novel method for preparing dimethachlor |
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