CN1986533A - Preparation and application of alkenyl amide cluster compound - Google Patents
Preparation and application of alkenyl amide cluster compound Download PDFInfo
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- CN1986533A CN1986533A CN 200710000633 CN200710000633A CN1986533A CN 1986533 A CN1986533 A CN 1986533A CN 200710000633 CN200710000633 CN 200710000633 CN 200710000633 A CN200710000633 A CN 200710000633A CN 1986533 A CN1986533 A CN 1986533A
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Abstract
The present invention is preparation and application of alkenyl amide cluster compounds obtained based on cluster effect principle. The alkenyl amide cluster compounds have the structural general expression as shown, novel structure and excellent bioactivity. For example, they may be used in preventing and controlling plant diseases caused by Puccinia striifomis, Urocystis agropyri, Rhizoctonia solani, Rhizoctonia cerealis, etc. Some of the alkenyl amide cluster compounds possesse certain herbicidal activity on Echinochloa crusgalli, Digitaria sanguinalis, Setaria viridis, etc.
Description
Technical field
The present invention relates to synthetic duster compound with agricultural biological activity.Relate in particular to the preparation and the application of alkenyl amide cluster compound.
Background technology
In recent years, scientist finds in the research of active oligosaccharides, if after the active oligosaccharides small molecules of a kind of parent made duster compound, its activity can increase (J.Am.Chem.Soc., 1999,121,8174 sometimes greatly; " carbohydrate chemistry " Kong Fanzuo writes, Science Press 2005).The multiple-effect valency part that bunch closes generation can interact with the multidigit point of acceptor, thereby produces synergistic effect, and its bonding force and specificity are strengthened.(Science，2001，291(23)：2357-2364)
Before this, the patent (CN2006100780634) that the existing utilization bunch method of closing is carried out the novel pesticide initiative relates to the synthetic of duster compounds such as Affirm (Merck Co.) and fluorine worm nitrile.But the disclosed compound of above-mentioned patent does not fall into the present invention.
Summary of the invention
The objective of the invention is to according to the cluster effect principle, select suitable parent compound to screen the potential pesticide molecule by synthetic its various duster compounds.
Technical scheme of the present invention is as follows:
The invention provides the duster compound of a class acrylamide, shown in general formula (I):
In the formula:
G is selected from one of following group:
R ' is H, halogen atom, (not) replacement C
1-C
12Alkyl, (not) replaces C
3-C
8Cycloalkyl, (not) replaces C
2-C
12Thiazolinyl, (not) replaces C
3-C
8Cycloalkenyl group, (not) replaces C
2-C
12That alkynyl, (not) replace is nitrogenous, oxygen, sulphur C
1-C
12Alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle, (not) substituted biphenyl etc.
M=2, D can be
L also can be the structure that top D lists, and also can be selected from one of following group:
R
1For H, (not) replace C
1-C
18Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
18Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
18Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
18Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
18Alkylidene group, (not) replace contains sulfonic C
1-C
18Alkylidene group etc.;
R
2For (not) replaces C
1-C
18Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
18Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
18Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
18Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
18Alkylidene group, (not) replace contains sulfonic C
1-C
18Alkylidene group etc.;
R
3, R
4Can be identical or different, be selected from (not) respectively and replace C
1-C
18Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
18Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
18Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
18Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
18Alkylidene group, (not) replace contains sulfonic C
1-C
18Alkylidene group etc.
R
5Be H, halogen, (not) replaces C
1-C
8Alkyl, (not) replaces C
3-C
8Cycloalkyl, (not) replaces C
2-C
8Thiazolinyl, (not) replaces C
3-C
8Cycloalkenyl group, (not) replaces C
2-C
8That alkynyl, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle,
n＝0，1，2
When m=3, D can be
L is the same.
When m=4, D can be
L is the same.
R
6For (not) replaces C
1-C
8Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
8Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
8That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkylidene group, (not) replaces arylidene, and (not) replaces inferior heterocyclic base
Look actual needs, middle interconnecting piece divides and can only be made up of D or L portion.
…
And steric isomer
In comparatively preferred general formula (I) compound,
L is selected from one of following group:
R
1For H, (not) replace C
1-C
12Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
12Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
12That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
12Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
12Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
12Alkylidene group, (not) replace contains sulfonic C
1-C
12Alkylidene group etc.;
R
2For (not) replaces C
1-C
12Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
12Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
12That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
12Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
12Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
12Alkylidene group, (not) replace contains sulfonic C
1-C
12Alkylidene group etc.;
R
3, R
4Can be identical or different, be selected from (not) respectively and replace C
1-C
12Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
12Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
12That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
12Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
12Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
12Alkylidene group, (not) replace contains sulfonic C
1-C
12Alkylidene group etc.
R
5Be H, halogen, (not) replaces C
1-C
6Alkyl, (not) replaces C
3-C
8Cycloalkyl, (not) replaces C
2-C
6Thiazolinyl, (not) replaces C
3-C
6Cycloalkenyl group, (not) replaces C
2-C
6That alkynyl, (not) replace is nitrogenous, oxygen, sulphur C
1-C
6Alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle,
n＝0，1，2
In further preferred general formula (I) compound,
L is selected from one of following group:
R
1For H, (not) replace C
1-C
8Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
8Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
8That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
8Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
8Alkylidene group, (not) replace contains sulfonic C
1-C
8Alkylidene group etc.;
R
2For (not) replaces C
1-C
8Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
8Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
8That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
8Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
8Alkylidene group, (not) replace contains sulfonic C
1-C
8Alkylidene group etc.;
R
3, R
4Can be identical or different, be selected from (not) respectively and replace C
1-C
8Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
8Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
8That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
8Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
8Alkylidene group, (not) replace contains sulfonic C
1-C
8Alkylidene group etc.
R
5Be H, halogen, (not) replaces C
1-C
4Alkyl, (not) replaces C
3-C
8Cycloalkyl, (not) replaces C
2-C
4Thiazolinyl, (not) replaces C
3-C
8Cycloalkenyl group, (not) replaces C
2-C
4That alkynyl, (not) replace is nitrogenous, oxygen, sulphur C
1-C
6Alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle,
n＝0，1，2
In the definition of the general formula compound among the present invention (I), compile the following substituting group of used term general proxy:
" alkyl " comprises the alkyl group of straight or branched.Typical alkyl has methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, iso-octyl, nonyl, decyl, undecyl, dodecyl and other.
" cycloalkyl " refers to the compound of fatty family ring structure, as cyclopropane, tetramethylene, pentamethylene, hexanaphthene, suberane, cyclooctane and other.
" thiazolinyl " refers to undersaturated hydrocarbon group, contains one or two pair key on the straight or branched.
" cycloalkenyl group " refers to the aliphatics ring and contains one or two pair key, as inferior cyclopentenes, inferior tetrahydrobenzene, 1, and the inferior tetrahydrobenzene of 4-and other.
" alkynyl " refers to undersaturated hydrocarbon group, contains one or two triple bond in the straight or branched.
" alkylidene group " comprises the alkylidene group of straight or branched.Typical alkylidene group has methylene radical, ethylidene, inferior n-propyl, isopropylidene, inferior normal-butyl, inferior sec-butyl, the inferior tertiary butyl, inferior n-pentyl, isopentylidene, inferior n-hexyl, inferior n-heptyl, inferior iso-octyl, nonamethylene, inferior decyl, inferior undecyl, inferior dodecyl and other.
" cycloalkylidene " refers to the compound of fatty family ring structure, as inferior cyclopropane, inferior tetramethylene, inferior pentamethylene, inferior hexanaphthene, inferior suberane, inferior cyclooctane and other.
" alkenylene " refers to undersaturated hydrocarbon group, contains one or two pair key on the straight or branched.
" inferior cycloalkenyl group " refers to the aliphatics ring and contains one or two pair key, as inferior cyclopentenes, inferior tetrahydrobenzene, 1, and the inferior tetrahydrobenzene of 4-and other.
" alkynylene " refers to undersaturated hydrocarbon group, contains one or two triple bond in the straight or branched.
" aryl " refers to monocycle or polynuclear compound, or benzene, naphthalene, indenes, anthracene, dicyclopentadiene and to dihydrobenzene, fluorenes, acenaphthene, phenanthrene and azulene.
" heterocyclic base " refers to monocycle or polycyclic furans, thiophene, pyrroles, piperazine, oxazole, isoxzzole, different thiadiazoles, thiazole, pyrazoles, imidazoles, 1,2,3-triazoles, 1,1,4-triazole, tetrazolium, 1,2, the 3-thiadiazoles, 1,1,4-thiadiazoles, 1,3, the 4-thiadiazoles, 1,1,4-thiadiazoles, 1,3, the 4-thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,1,4-triazine, 1,1,4,5-tetrazine, cumarone, thionaphthene, indoles, the benzisoxa oxazole, benzoxazoles, benzisothiazole, benzothiazole, benzopyrazoles, benzoglyoxaline, benzotriazole, 1,2-methylenedioxyphenyl, ethylene dioxy base benzene, quinoline and isoquinoline 99.9.
" aralkyl " refers in alkyl group side chain or the straight chain and is called aralkyl by the formed part that contains aryl of aryl replacement.
" the assorted alkyl of virtue " refers in alkyl group side chain or the straight chain and is called aralkyl by the formed part that contains aryl of heterocyclic base replacement.
In the compound of the present invention,, L portion forms steric isomer (representing different configurations with Z and E respectively) owing to having the linker that contains carbon-to-carbon double bond and carbon-nitrogen double bond functional group.Compound of the present invention comprises the mixture of Z type and E-isomer and any ratio thereof.
The present invention can be prepared by following method by the represented compound of general formula (I):
Method 1: with G is G
1In time, give an example
In the above-mentioned reaction, Z
1Be leavings group, be selected from halogen, hydroxyl, oxyalkyl.
With chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, tetrahydrofuran (THF), dioxane, acetone, or inert solvent such as butanone is a solvent, as triethylamine, pyridine, yellow soda ash exist down under alkaline condition, control reaction temperature can generate the represented compound of general formula (I) in 1 hour～12 hours at-40 ℃～reaction solution reflux temperature.Alkali-free exists down also can make object.
Method 2:
In the above-mentioned reactant, Z
2Be leavings group, be selected from halogen, hydroxyl etc.
Reactant is a solvent with toluene, DMSO or DMF in the presence of sodium hydride or alkaline, and control reaction temperature stirs and can generate the represented compound of general formula (I) in 1 hour～12 hours at-40 ℃～0 ℃.
Work as m=2, when the connection portion is made of L, can the present invention be described with the compound of listing in the following table 1, but limit the present invention.
Table 1
When m=3, (L or choosing or do not select) can illustrate the present invention with the compound of listing in the following table 2, but do not limit the present invention.
Table 2
Embodiment
With specific embodiment method of the present invention is further described below.
Example 1: the preparation of compound 2
At room temperature, amicarthiazol adds in the reaction flask, to wherein adding 100 milliliters of THF, at N behind the 5.16g purifying
2Protection under, drip the 1.33g oxalyl chloride.After dropwising, continued stirring reaction 4 hours.With NaHCO
3Solution washing filters, and drying gets the 3.67g white solid matter, yield 67%.Fusing point: 145-147 ℃.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm2.47(6H，s)，7.02(2H，m)，7.22(4H，m)，7.62(4H，m)，8.02(4H，m)。
Example 2: the preparation of compound 3
Synthetic with reference to aforesaid method, get white solid matter.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm?2.45(6H，s)，3.07(2H，s)7.00(2H，m)，7.24(4H，m)，7.64(4H，m)，8.00(4H，m)。
Example 3: the preparation of compound 4
Synthetic with reference to aforesaid method, get white solid matter.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm?2.46-2.47(10H，t)，7.03(2H，m)，7.25(4H，m)，7.66(4H，m)，8.03(4H，m)。
Example 4: the preparation of compound 7
Synthetic with reference to aforesaid method, get white solid matter.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm1.57(4H，m)，2.18(4H，m)，2.46(6H，s)，7.01(2H，m)，7.23(4H，m)，7.65(4H，m)，8.04(4H，m)。
Example 5: the preparation of compound 13
At room temperature, amicarthiazol adds in the reaction flask, to wherein adding 60 milliliters of THF, at N behind the 2.85g purifying
2Protection under, add the 1.01g p-phthaloyl chloride, stirring reaction 4 hours.With NaHCO
3Solution washing filters, and drying gets the 1.78g white solid matter, yield 60%.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm?2.46(6H，s)，7.02(2H，m)，7.24(4H，m)，7.62(4H，m)，8.03(4H，m)，8.14(4H，s)。
Example 6: the preparation of compound 14
Synthetic with reference to aforesaid method, get white solid matter.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm2.45(6H，s)，7.04(2H，m)，7.24(4H，m)，7.60(1H，m)，7.66(4H，m)，8.03(4H，m)，8.20(2H，m)，8.64(1H，s)。
Example 7: the preparation of compound 15
Synthetic with reference to aforesaid method, get white solid matter.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm2.44(6H，s)，7.00(2H，m)，7.23(4H，m)，7.62(4H，m)，7.69(2H，m)，8.00(4H，m)，8.13(2H，m)。
Example 8: the preparation of compound 59
At room temperature, 3.03g amicarthiazol, 0.31gNaH add in the reaction flask, to wherein adding 80 milliliters of methylene dichloride, drip, and stirring reaction is 3 hours under the ice bath, drips 1.4g1 then, the 4-dibromobutane.After dropwising, reflux 10 hours.With saturated Na
2CO
3Solution washing is used ethyl acetate extraction, steams the molten post of crossing, and gets 2.3g yellow oily liquid, yield 68%.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm1.52(4H，m)，2.47(6H，s)，3.06(4H，m)，4.00(2H，t)，7.02(2H，m)，7.24(4H，m)，7.64(4H，m)，8.03(2H，s)。
Example 9: the preparation of compound 211
The 3.7g carboxin of at room temperature packing into adds the benzene of 15ml again, adds the 2.2g SULPHURYL CHLORIDE in batches, after the processing the 3.6g intermediate product.Add 0.96gK
2CO
3With 0.41g ethylene glycol, refluxed 2 hours.The reaction after product is with chloroform and water washing, steams moltenly, and recrystallization gets target product 2.12g.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm3.24(4H，m)，3.54(4H，m)，4.04(4H，s)，4.63(4H，m)，7.02(2H，m)，7.24(4H，m)，7.64(4H，m)，8.03(2H，m)。
Example 10: the preparation of compound 212
At room temperature, amicarthiazol adds in the reaction flask behind the 3.84g purifying, to wherein adding 60 milliliters of trielines, under alkaline condition, adds 0.92g 2,4,6-trichloro-triazine, stirring reaction 24 hours.Filter, washing, drying gets the 2.03g white solid matter, yield 46%.
Nuclear magnetic data (
1HNMR, 300MHz, interior mark TMS, solvent DMSO)
δppm2.47(9H，s)，4.08(3H，s)，7.05(3H，m)，7.27(6H，m)，7.68(6H，6H)，7.98(3H，m)。
Other compounds synthesize with reference to the reaction method of respective type.
Example of formulations (add-on of active ingredient is metered into after rolling over hundred in the prescription, and all percentage compositions are weight percentage)
Example 11:40% aq suspension
Compound 2 (content 95%) 30%
Dodecyl sodium naphthalene sulfonate 5%
Hemicellulose 3%
Propylene oxide 7%
Water supply 100%
Example 12:15% suspension agent
Compound 4 (content 95%) 15%
Methyl naphthalene sulfonate formaldehyde condensate 8%
Neusilin 0.1%
White carbon black 0.3%
Ethylene glycol 5%
Defoamer a little
Water complements to 100%
Biological activity determination
Example 13: fungicidal activity is measured
With The compounds of this invention the various fungus diseases of plant are measured.Adopt live body (in vivo) test method(s):
Adopt the potted plant measuring method of live body.In generation, surveyed the former medicinal small amount of acetone dissolving of compound, is diluted to required concentration with the water that contains 0.1% tween 80.Spray pesticide carries out the disease inoculation after dried slightly to plant examination material, put into hot-house culture, makes to infect and continues, wait to contrast abundant morbidity after (being generally week age) carry out assessment surveys.
The result of partial test is as follows:
During 300ppm, puccinia striiformis (Puccinia striifomis.) preventive effect there is compound 2,3,4,7,14 etc. greater than 90% compound.
During 300ppm, wheat bar ustilago (Urocystis agropyri) preventive effect there is compound 4,13,14,15,211 etc. greater than 90% compound.
Example 14: fungicidal activity is measured
Adopt bacterium dish growth diameter assay method to carry out toxicity test.In generation, surveyed the former medicinal small amount of acetone dissolving of compound, is diluted to required concentration with the water that contains 0.1% tween 80.After making toxic substratum, connect bacterium.Investigate after cultivating a week.
200ppm is to dry thread Pyrenomycetes (Rhizoctonia solani). and preventive effect has compound 2,3,4,7,211 etc. greater than 90% compound.
200ppm has compound 2,4,13,7,14,211 etc. to rhizoctonia cerealis (Rhizoctonia cerealis) preventive effect greater than 90% compound.
Example 15: weeding activity is measured
Carrying out weeding activity with compound of the present invention measures.With non-irrigated barnyard grass (Echinochloa crusgalli), lady's-grass (Digitariasanguinalis), Herba Setariae Viridis (Setaria viridis) is tested object.Measure behind the seedling, seed germination also grew 10-15 days.Select examination material of the same size to handle.In generation, surveys compound and dissolves with suitable solvent (generally using acetone), and its preparation is directly used water dissolution, the processing of spraying then.In handling 2 weeks or the investigation of 3 weeks.
At 300g/ha, compound 211 grades have certain inhibition activity to above-mentioned weeds.
Claims (7)
1. the duster compound of a class acrylamide compound, shown in general formula (I):
In the formula:
G is selected from one of following group:
R ' is H, halogen atom, (not) replacement C
1-C
12Alkyl, (not) replaces C
3-C
8Cycloalkyl, (not) replaces C
2-C
12Thiazolinyl, (not) replaces C
3-C
8Cycloalkenyl group, (not) replaces C
2-C
12That alkynyl, (not) replace is nitrogenous, oxygen, sulphur C
1-C
12Alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle, (not) substituted biphenyl etc.
Work as m=2, D can be
L also can be the structure that top D lists, and also can be selected from one of following group :-CHR
1-,
R
1For H, (not) replace C
1-C
18Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
18Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
18Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
18Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
18Alkylidene group, (not) replace contains sulfonic C
1-C
18Alkylidene group etc.;
R
2For (not) replaces C
1-C
18Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
18Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
18Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
18Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
18Alkylidene group, (not) replace contains sulfonic C
1-C
18Alkylidene group etc.;
R
3, R
4Can be identical or different, be selected from (not) respectively and replace C
1-C
18Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
18Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
18Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
18Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
18Alkylidene group, (not) replace contains sulfonic C
1-C
18Alkylidene group etc.
R
5Be H, halogen, (not) replaces C
1-C
8Alkyl, (not) replaces C
3-C
8Cycloalkyl, (not) replaces C
2-C
8Thiazolinyl, (not) replaces C
3-C
8Cycloalkenyl group, (not) replaces C
2-C
8That alkynyl, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle,
n＝0，1，2
When m=3, D can be
L is the same.
When m=4, D can be
L is the same.
R
6For (not) replaces C
1-C
8Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
8Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
8That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkylidene group, (not) replaces arylidene, and (not) replaces inferior heterocyclic base
Look actual needs, middle interconnecting piece divides and can only be made up of D or L portion.
...
And steric isomer.
2. compound according to claim 1 is characterized in that: in the general formula (I)
L is selected from one of following group :-CHR
1-,
R
1For H, (not) replace C
1-C
12Alkylidene group, (not) replaces C
8-C
3Cycloalkylidene, (not) replaces C
2-C
12Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
12That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
12Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
12Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
12Alkylidene group, (not) replace contains sulfonic C
1-C
12Alkylidene group etc.;
R
2For (not) replaces C
1-C
12Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
12Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
12That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
12Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
12Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
12Alkylidene group, (not) replace contains sulfonic C
1-C
12Alkylidene group etc.;
R
3, R
4Can be identical or different, be selected from (not) respectively and replace C
1-C
12Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
12Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
12That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
12Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
12Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
12Alkylidene group, (not) replace contains sulfonic C
1-C
12Alkylidene group etc.
R
5Be H, halogen, (not) replaces C
1-C
6Alkyl, (not) replaces C
3-C
8Cycloalkyl, (not) replaces C
2-C
6Thiazolinyl, (not) replaces C
3-C
6Cycloalkenyl group, (not) replaces C
2-C
6That alkynyl, (not) replace is nitrogenous, oxygen, sulphur C
1-C
6Alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle,
n＝0，1，2
3. compound according to claim 2 is characterized in that: in the general formula (I)
L is selected from one of following group :-CHR1-,
() do not replace C
1-C
8Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
8Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
8That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
8Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
8Alkylidene group, (not) replace contains sulfonic C
1-C
8Alkylidene group etc.;
R
2For (not) replaces C
1-C
8Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
8Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
8That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
8Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
8Alkylidene group, (not) replace contains sulfonic C
1-C
8Alkylidene group etc.;
R
3, R
4Can be identical or different, be selected from (not) respectively and replace C
1-C
8Alkylidene group, (not) replaces C
3-C
8Cycloalkylidene, (not) replaces C
2-C
8Alkenylene, (not) replaces C
3-C
8Inferior cycloalkenyl group, (not) replaces C
2-C
8That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C
1-C
8Alkylidene group, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains amido that (not) replaces
1-C
8Alkylidene group, alkylsulfonyl, the C that contains alkylsulfonyl that (not) replaces
1-C
8Alkylidene group, (not) replace contains sulfonic C
1-C
8Alkylidene group etc.
R
5Be H, halogen, (not) replaces C
1-C
4Alkyl, (not) replaces C
3-C
8Cycloalkyl, (not) replaces C
2-C
4Thiazolinyl, (not) replaces C
3-C
8Cycloalkenyl group, (not) replaces C
2-C
4That alkynyl, (not) replace is nitrogenous, oxygen, sulphur C
1-C
6Alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle,
n＝0，1，2
4. according to any described compound among the claim 1-3, it is characterized in that: (G is with G for the compound of general formula (I)
1Be example) make by following reaction:
In the above-mentioned reaction, Z
1Be leavings group, be selected from halogen, hydroxyl, oxyalkyl.
In the above-mentioned reactant, Z
2Be leavings group, be selected from halogen, hydroxyl etc.
5. the described compound of claim 1 is in the application of control crop germ.
6. the utilization of the described compound of claim 1 aspect controlling weeds.
7. a sterilization, herbicidal composition, it is characterized in that: contain described general formula 1 compound of claim 1 in the composition, the weight percentage of active ingredient is 0.1-99%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710000633 CN1986533A (en) | 2007-01-11 | 2007-01-11 | Preparation and application of alkenyl amide cluster compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710000633 CN1986533A (en) | 2007-01-11 | 2007-01-11 | Preparation and application of alkenyl amide cluster compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1986533A true CN1986533A (en) | 2007-06-27 |
Family
ID=38183489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200710000633 Pending CN1986533A (en) | 2007-01-11 | 2007-01-11 | Preparation and application of alkenyl amide cluster compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1986533A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610248A (en) * | 2014-12-25 | 2015-05-13 | 中国农业科学院植物保护研究所 | Multi-titer sulfonyl triazole compounds and application thereof |
| CN104610249A (en) * | 2014-12-25 | 2015-05-13 | 中国农业科学院植物保护研究所 | Bi-titer sulfonyl isoxazole derivative and application thereof |
| WO2016163379A1 (en) * | 2015-04-09 | 2016-10-13 | 住友化学株式会社 | Oxalyl amide compound and use thereof for noxious arthropod control |
| WO2016163383A1 (en) * | 2015-04-09 | 2016-10-13 | 住友化学株式会社 | Oxalyl amide compound and use thereof for noxious arthropod control |
-
2007
- 2007-01-11 CN CN 200710000633 patent/CN1986533A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610248A (en) * | 2014-12-25 | 2015-05-13 | 中国农业科学院植物保护研究所 | Multi-titer sulfonyl triazole compounds and application thereof |
| CN104610249A (en) * | 2014-12-25 | 2015-05-13 | 中国农业科学院植物保护研究所 | Bi-titer sulfonyl isoxazole derivative and application thereof |
| CN104610249B (en) * | 2014-12-25 | 2017-09-15 | 中国农业科学院植物保护研究所 | A kind of two potency sulfonyl isoxazole derivates and its application |
| CN104610248B (en) * | 2014-12-25 | 2018-07-20 | 中国农业科学院植物保护研究所 | A kind of multiple-effect valence sulfonyl triazoles class compound and its application |
| WO2016163379A1 (en) * | 2015-04-09 | 2016-10-13 | 住友化学株式会社 | Oxalyl amide compound and use thereof for noxious arthropod control |
| WO2016163383A1 (en) * | 2015-04-09 | 2016-10-13 | 住友化学株式会社 | Oxalyl amide compound and use thereof for noxious arthropod control |
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