CN108191844A - The activity of the resisting tobacco mosaic virus of the 2- methyl butyne amine acylated derivatives of the dithienyl pyridine structure containing 2,6- - Google Patents
The activity of the resisting tobacco mosaic virus of the 2- methyl butyne amine acylated derivatives of the dithienyl pyridine structure containing 2,6- Download PDFInfo
- Publication number
- CN108191844A CN108191844A CN201810046640.4A CN201810046640A CN108191844A CN 108191844 A CN108191844 A CN 108191844A CN 201810046640 A CN201810046640 A CN 201810046640A CN 108191844 A CN108191844 A CN 108191844A
- Authority
- CN
- China
- Prior art keywords
- activity
- thiophene
- mosaic virus
- tobacco mosaic
- bases
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The activity of the resisting tobacco mosaic virus of class compound is acylated the present invention relates to 2 methyl 4 (5 (3 (2 base of thiophene) pyridyl group) thiophene, 2 base) 3 alkynes of fourth, 2 amine.Wherein R=2 chlorphenyls；2 aminomethyl phenyls；Phenyl；2 methoxyphenyls；2 fluorophenyls；2,4 3,5-dimethylphenyls.In 500ppm formulation rates, passivation activity, therapeutic activity and protection activity are showed to tobacco mosaic virus (TMV).
Description
(1) technical field
The present invention relates to 2- methyl -4- (5- (3- (thiophene -2- bases) pyridyl group) thiophene -2- bases) butyl- 3- alkynes -2- amine acyl groups
Change the activity of the resisting tobacco mosaic virus of class compound.
(2) background technology
Tobacco mosaic virus disease is one of Main Tobacco Diseases, and harm is big, and prevention is difficult, it is prevented there is no effectively at present
Drug, the Main Preventive Measures taken have the disease-resistant tobacco bred of selection, improve nutrition of the host resistance, and anti-aphid is disease-resistant, kills cause of disease
It improves disease-resistant and applies chemoprophylaxis, prophylactic agent can be divided into natural class and non-natural class.Due to natural class chemoprophylaxis effect
Not satisfactory, it is difficult to obtain in addition, and cost is higher, therefore the non-natural class disease-resistance substance for synthesizing some high-efficiency low-toxicities necessitates.
Traditional commercialization chemistry anti-plant virus agent for example Ningnanmycin, Ribavirin, Physcion, DHT, DADHT,
Chlorobromide isocyanuric acid and Moroxydine Hydrochloride when application because its limited efficacy due to by larger limitation.The work of China's scientific research in recent years
Author achieves major progress in the innovative research work of anti-plant virus agent, it is found that many has anti-phytoviral activity
Compound, as toxic fluoride phosphate and first thiophene lure amine.Effective at present and satisfactory anti-plant virus agent functionization kind is not much
(it is the agriculture chemical registration of the Yi Huo Ministry of Agriculture close with traditional anti-plant virus agent Ningnanmycin in its preventive effect of field practical application]), especially
The therapeutic medicament of its special efficacy is less, it is therefore desirable to more efficient, the safe and environmental-friendly anti-plant virus agent service of exploitation
In the development of China's agricultural.
To the research for focusing primarily upon such compound optoelectronic properties to 1,3- dithienyl pyridine derivates at present,
But without any 2- methyl -4- (5- (3- (thiophene -2- bases) pyridyl group) thiophene -2- specifically recorded mentioned in this patent
Base) butyl- 3- alkynes -2- amine acylation class compound, more without any resisting tobacco mosaic virus for specifically recording these compounds
Activity.
(3) invention content
The object of the present invention is to provide a kind of 2- methyl -4- (5- (3- (thiophene -2- bases) pyridyl group) thiophene -2- bases) butyl-
3- alkynes -2- amine is acylated class compound and its preparation method and application.
The present invention is the following general formula (1) compound：
Wherein R=2- chlorphenyls；2- aminomethyl phenyls；Phenyl；2- methoxyphenyls；2- fluorophenyls；2,4- 3,5-dimethylphenyls.
In 500ppm formulation rates, passivation activity, therapeutic activity and protection activity are showed to tobacco mosaic virus (TMV).
(4) specific embodiment
The substantive distinguishing features of the present invention can emerge from, but it is not construed as appointing the present invention from following embodiments
What is limited.The compounds of this invention (I) synthetic route is：
Embodiment 1：N- (2- methyl 4- (5- (3- (thiophene -2- bases) pyridyl group) thiophene -2- bases) butyl- 3- alkynes -2- bases) is adjacent
Chlorobenzamide (1a)
0.04 mole of acyl chloride is added in 50 milliliters of reaction bulbs, 10 milliliters of dioxane through Non-aqueous processing stir, and add in
0.01 mole of 2- methyl 4- (5- (3- (thiophene -2- bases) pyridyl group) thiophene -2- bases) butyl- 3- alkynes -2- amine, is stirred at room temperature to original
Shots (amine) disappear substantially, new point no longer changes, about 24 hours.Concentration, handles to obtain sterling through column chromatography.
Embodiment 2：N- (2- methyl 4- (5- (3- (thiophene -2- bases) pyridyl group) thiophene -2- bases) butyl- 3- alkynes -2- bases) is adjacent
Methyl benzamide (1b)
0.03 mole of o-methyl-benzene formyl chloride of addition in 50 milliliters of reaction bulbs, 20 milliliters of dioxane through Non-aqueous processing,
0.5 milliliter of triethylamine, stirring, is added portionwise 0.015 mole of 2- methyl 4- (5- (3- (thiophene -2- bases) pyridyl group) thiophene -2-
Base) butyl- 3- alkynes -2- amine, it is stirred at room temperature to raw material point (amine) disappearance, new point substantially and no longer changes, about 24 hours.Concentration, through column
Image processing obtains sterling.
It has synthesized compound (1) in a similar way, the physical parameter result of compound and tobacco mosaic virus (TMV) has been pressed down
Rate processed is shown in Table 1.
Embodiment 4 tests tobacco mosaic virus (TMV) inhibiting rate
Live body protective effect：3~5 consistent leaf phase Nicotiana glutinosas of growing way are chosen, are limited with main lobe arteries and veins, it is with writing brush that medicament is light
Left half leaf is applied to, right half leaf applies clear water control, often handles 5 repetitions.Processing is placed on observation ward, dries rear full leaf frictional inoculation
Tobacco mosaic virus (TMV).After 2~3d, half leaf withered spot number of record left and right, calculates preventive effect respectively.
Live body therapeutic effect：：3~5 consistent leaf phase Nicotiana glutinosas of growing way are chosen, full leaf frictional inoculation TMV is left after drying
Half leaf spreads medicament, and right half leaf applies clear water control, often handles 5 repetitions.After 2~3d, half leaf withered spot number of record left and right, is counted respectively
Calculate preventive effect.
Live body passivation：TMV viruses after Passivation Treatment and medicament mixed liquor are applied to left half leaf of Nicotiana glutinosa, the right side half
Leaf sets the control of homogenous quantities concentration Virus eliminating medicine water mixed liquid, often handles 5 repetitions.After 2~3d, half leaf withered spot of left and right is recorded respectively
Number calculates preventive effect.
The physical property of 1 compound of table (1) is characterized to tobacco mosaic virus (TMV) inhibiting rate (%；Concentration：500ppm)
Claims (2)
1. a kind of 2- methyl -4- (5- (3- (thiophene -2- bases) pyridyl group) thiophene -2- bases) butyl- 3- alkynes -2- amine is acylated class chemical combination
Object, it is characterised in that it is the compound of logical formula (I)：
Wherein R=2- chlorphenyls；2- aminomethyl phenyls；Phenyl；2- methoxyphenyls；2- fluorophenyls；2,4- 3,5-dimethylphenyls.
2- methyl -4- described in claim 1 2. (5- (3- (thiophene -2- bases) pyridyl group) thiophene -2- bases) butyl- 3- alkynes -2- amine acyls
The application of base class compound, it is characterised in that the inhibiting effect of tobacco mosaic virus (TMV).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810046640.4A CN108191844A (en) | 2018-01-16 | 2018-01-16 | The activity of the resisting tobacco mosaic virus of the 2- methyl butyne amine acylated derivatives of the dithienyl pyridine structure containing 2,6- |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810046640.4A CN108191844A (en) | 2018-01-16 | 2018-01-16 | The activity of the resisting tobacco mosaic virus of the 2- methyl butyne amine acylated derivatives of the dithienyl pyridine structure containing 2,6- |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108191844A true CN108191844A (en) | 2018-06-22 |
Family
ID=62590156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810046640.4A Pending CN108191844A (en) | 2018-01-16 | 2018-01-16 | The activity of the resisting tobacco mosaic virus of the 2- methyl butyne amine acylated derivatives of the dithienyl pyridine structure containing 2,6- |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108191844A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999011631A1 (en) * | 1997-09-04 | 1999-03-11 | Novartis Ag | Pyrimidin-2-oxy-4-one and pyrimidin-2-oxy-4-thione derivatives |
| CN104045622A (en) * | 2014-07-04 | 2014-09-17 | 南开大学 | Tobacco mosaic virus resistant activity of N-(4-(2,2':5',2'-terthienyl-5-yl)-methylbutyl-3-alkynyl-2-yl) substituted benzamide compound |
-
2018
- 2018-01-16 CN CN201810046640.4A patent/CN108191844A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999011631A1 (en) * | 1997-09-04 | 1999-03-11 | Novartis Ag | Pyrimidin-2-oxy-4-one and pyrimidin-2-oxy-4-thione derivatives |
| CN104045622A (en) * | 2014-07-04 | 2014-09-17 | 南开大学 | Tobacco mosaic virus resistant activity of N-(4-(2,2':5',2'-terthienyl-5-yl)-methylbutyl-3-alkynyl-2-yl) substituted benzamide compound |
Non-Patent Citations (3)
| Title |
|---|
| YOUQUAN ZHU ET AL.: ""Design, Synthesis and Biological Evaluation of Novel N-(4-([2,2":5",2 ""-Terthiophen]-5-yl)-2-methylbut-3-yn-2-yl) Benzamide Derivatives"", 《CHIN. J. CHEM.》 * |
| 吴志兵等: ""5-胺基-1-(3-氯-2-吡啶基)-4-(5-甲硫基-1,3,4-恶二唑-2-基)-吡唑衍生物的合成及抗烟草花叶病毒活性研究"", 《中国科学》 * |
| 张海利: ""新型抗病毒化合物和PPO抑制剂的设计、合成及生物活性研究"", 《万方学术期刊数据库》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5635644B2 (en) | Soil treatment agent or seed treatment agent containing a quinoline compound or a salt thereof as an active ingredient, or a method for controlling plant diseases using them | |
| JP6649967B2 (en) | Bactericidal composition | |
| CN107848959A (en) | The phenoxyphenylamidineand of halogen substitution and its purposes as fungicide | |
| CN104797564A (en) | Herbicidal and fungicidal 5-oxy-substituted 3-phenylisoxazoline-5-carboxamides and 5-oxy-substituted 3-phenylisoxazoline-5-thioamides | |
| CN103025723A (en) | Pyridinylcarboxylic acid derivatives as fungicides | |
| TW201234970A (en) | Active compound combinations | |
| CN104812751A (en) | Nitrogen-containing heterocyclic compounds for plant disease control | |
| KR20110044925A (en) | How to promote plant growth | |
| CN101835773A (en) | Novel imidazole derivatives | |
| CN104412985A (en) | Phenanthrene-containing heterocycle compound and preparation method and application in resisting plant virus | |
| JP6007360B2 (en) | Bacterial wilt resistance inducer and bacterial wilt control method | |
| CN104039146A (en) | 2-iodo Imidazole-derivatives | |
| CN108349895A (en) | Substituted 2- difluoromethyls-nicotine (thio) formailide derivative and its purposes as fungicide | |
| CN101835772B (en) | Novel imidazole derivatives | |
| BR112019007483B1 (en) | 4-SUBSTITUTED PHENYLAMINE DERIVATIVES AND THEIR USE TO PROTECT CROPS BY FIGHTING UNWANTED PHYTOPATHOGENIC MICROORGANISMS | |
| CN102958923A (en) | Heterocyclic alkanol derivatives as fungicides | |
| CN102985414A (en) | Heterocyclic thiosubstituted alkanol derivatives as fungicides | |
| CN108191844A (en) | The activity of the resisting tobacco mosaic virus of the 2- methyl butyne amine acylated derivatives of the dithienyl pyridine structure containing 2,6- | |
| CN105777807A (en) | Chalcone phosphonate derivative containingquinazoline and preparation method and application of chalcone phosphonate derivative | |
| CN106496212B (en) | A kind of pyrazoles connection oxadiazoles thio-ether type compounds and the preparation method and application thereof | |
| CN108347948A (en) | Include the active agent combinations of (thio) carboxamide derivative and Fungicidal compounds | |
| CN108191817A (en) | The activity of the resisting tobacco mosaic virus of the 2- methyl butyne amine acylated derivatives of the dithienyl benzene structure containing 1,3- | |
| CN109983000A (en) | The imidazolyl methyl-derivatives that new 5- replaces | |
| CN109232534B (en) | Heterocyclic diarylamine-containing pyrazole formamide compound and preparation method and application thereof | |
| CN107098869B (en) | Bisamide class compound of the base of oxadiazoles containing 1,3,4- and preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20180622 |