CN109553605A - Pyrazol acid amide compounds of the biphenyl structures containing tetrazole and its preparation method and application - Google Patents
Pyrazol acid amide compounds of the biphenyl structures containing tetrazole and its preparation method and application Download PDFInfo
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- CN109553605A CN109553605A CN201811480609.8A CN201811480609A CN109553605A CN 109553605 A CN109553605 A CN 109553605A CN 201811480609 A CN201811480609 A CN 201811480609A CN 109553605 A CN109553605 A CN 109553605A
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- Prior art keywords
- acid amide
- amide compounds
- structures containing
- tetrazole
- compound
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
Abstract
The present invention relates to pyrazol acid amide compounds (I) of a kind of biphenyl structures containing tetrazole and its preparation method and application.It is condensed to yield by substituent group pyrazoles formoxyl chlorine (II) and tetrazole diphenylmethyl amine (III).The pyrazol acid amide compounds of the biphenyl structures containing tetrazole have effective control efficiency to harmful insect, which can be used for preparing the insecticide in the fields such as agricultural, gardening.
Description
Technical field
The present invention relates to chemical pesticide fields, and in particular to a kind of pyrazol acid amide chemical combination of the biphenyl structures containing tetrazole
Object and its preparation method and application.
Background technique
The prevention and treatment of pest is the core realm of pesticide science research all the time, and insecticide is widely used so that most evils
Worm has obtained effective improvement.But with the continuous expansion of insecticide application scale, the resistance problems of traditional pesticide species are increasingly
It highlights, in addition the emergence of new pest and disease damage, so that the research and development that continues of novel pesticide becomes inevitable choice.
Pyrazole ring is widely used in terms of agricultural production, and pyrazole compound has excellent desinsection, mite killing isoreactivity, pyrrole
Azoles heterocycle is widely introduced into agricultural chemical compound molecule, right such as pyrazole amide insecticidal/acaricidal agent tebufenpyrad and Tolfenpyrad
Acarid, aphid etc. have excellent killing activity (Biochim.Biophys.Acta 1998,1364,236-244).
Tetrazole is also a kind of important nitrogen-containing heterocycle, is played an important role in terms of the desinsection of pesticide field.In recent years
Carry out some researchs and reports tetrazole derivative with good insecticidal effect.
Therefore, it in order to further find the compound with excellent bioactivity from pyrazol acid amide compounds, uses
Pyrazole amide group and tetrazole skeleton are reasonably engaged togather by active group joining method, and the invention discloses one kind
The pyrazol acid amide compounds of the phenyl structure containing tetrazole with agricultural insecticidal application value.
Summary of the invention
It is and efficient, safe, environmental-friendly the object of the present invention is to provide there is excellent control efficiency for various pests
The pyrazol acid amide compounds of one kind biphenyl structures containing tetrazole, to meet crop protection to efficient pesticides demand.
A further object of the present invention is to provide purposes of the above compound in terms of preparing insecticide.
It is a further object of the present invention to provide the preparation methods of above compound.
In order to solve the above technical problems, the first aspect of the present invention provides a kind of pyrazoles acyl of biphenyl structures containing tetrazole
Aminated compounds, with general formula I,
Wherein, R=4-OCH3C6H4,4-FC6H4,2,4-F2C6H3,CH3,C2H5。
Preferably, the pyrazol acid amide compounds of the biphenyl structures containing tetrazole have the following structure:
The second aspect of the present invention provides the preparation side of the pyrazol acid amide compounds of the above-mentioned biphenyl structures containing tetrazole
Method comprising following steps:
Compound III is dissolved in organic solvent, acid binding agent is added, then in addition intermediate II, one section of final reaction
Between, reaction solution is filtered, mother liquor is concentrated under reduced pressure, and gained residue isolates and purifies to obtain target compound,
Wherein, R=4-OCH3C6H4,4-FC6H4,2,4-F2C6H3,CH3,C2H5
Preferably, the acid binding agent is selected from DIPEA, pyridine, triethylamine, sodium carbonate, and the solvent is selected from acetonitrile, DMF, two
Chloromethanes, 1,2- dichloroethanes.The heating reaction temperature is 0 DEG C -82 DEG C, and the reaction time is 8-13 hours.
Preferably, the pyrazol acid amide compounds of the biphenyl structures containing tetrazole the preparation method is as follows:
Wherein, tetrazole Biphenylmethyl amine intermediate III can refer to the side of document (J.Med.Chem.1998,41,2390)
Method synthesizes to obtain；The e of intermediate II a~II can refer to the side of document (J.Agric.Food Chem.2013,61,8730-8736)
Method synthesizes to obtain.
Compound of Formula I has excellent prevention and treatment activity to insect, thus the compound of the present invention can be used as preparing desinsection
Agent, and then protect the plants such as agricultural, gardening.The insect include lepidoptera pest for example bollworm, beet armyworm, diamondback moth,
Cabbage caterpillar, rice leaf roller and striped rice borer etc.；Homoptera pest such as leafhopper, plant hopper, earthworm worm, aleyrodid, the scale insect of Psyllidae etc.；
Diptera pest such as housefly, Liriomyza, mosquito class etc.；The locust etc. of Orthoptera, longicorn, chafer, weevil, bean weevil of coleoptera etc.
Pest etc.；The stinkbug etc. of Semiptera.Certainly, the harmful organism that the compound of the present invention can prevent and treat is not limited to the range of the example above.
When the compound of the present invention indicated by general formula I is used as the insecticide in the fields such as agricultural, gardening, can individually make
With, or used in a manner of Pesticidal combination, such as using Formulas I as active constituent, in addition insecticides adjuvant commonly used in the art is processed into
Aqueous emulsion, suspending agent, water dispersion granule, missible oil etc..
Common insecticides adjuvant includes: liquid-carrier, such as water；Organic solvent such as toluene, dimethylbenzene, cyclohexanol, methanol, fourth
Alcohol, ethylene glycol, acetone, dimethylformamide, acetic acid, dimethyl sulfoxide, animal and plant oil and fatty acid；Common surface agent is such as
Emulsifier and dispersing agent, including anionic surfactant, cationic surfactant, nonionic surfactant and both sexes table
Face activating agent；Other auxiliary agents, such as wetting agent, thickener.
When being used as the active constituent in insecticide by the compound of the present invention that general formula I is indicated, in the insecticide
Content is selected in the range of 0.1% to 99.5%, and can determine activity appropriate according to dosage form and method of administration
Component content.In general, preferably it contains containing active constituent described in 5% to 50% (weight percent, similarly hereinafter) in aqueous emulsion
Amount is 10% to 40%；In suspending agent containing 5% to 50% active constituent, preferably its content be 5% to 40%.
Common application method may be selected in use for insecticide of the invention, as cauline leaf is spraying, used for ponds, native
Earth processing and seed treatment etc..For example, when spraying using cauline leaf, the compound indicated by general formula I as active constituent
Can be used concentration range be 1 to 1000 μ g/mL aqueous emulsion, suspending agent, water dispersion granule, missible oil, preferably its concentration be 1 to
500μg/mL。
The pyrazol acid amide compounds of the biphenyl structures disclosed by the invention containing tetrazole have harmful insect excellent
Control efficiency, therefore can be used to prepare the insecticide for fields such as agricultural, gardening.
Specific embodiment
Above scheme is described further below in conjunction with specific embodiment.It should be understood that these embodiments are for illustrating
The present invention and be not limited to limit the scope of the invention.Implementation condition used in the examples can be done according to the condition of specific producer
Further adjustment, the implementation condition being not specified is usually the condition in routine experiment.
Embodiment 1:
5mmol compound III is dissolved in 30mL DMF, 15mmol DIPEA (n,N-diisopropylethylamine) then is added.Room
Intermediate II a 6mmol is added under the conditions of temperature thereto, finishes, is stirred at room temperature 11 hours.Stop reaction, reaction solution is poured into Sheng
In the beaker for having 100mL water, ethyl acetate extraction, anhydrous sodium sulfate is dry, and to doing, gained residue chromatographs vacuum rotary steam through column
It isolates and purifies to obtain target compound Ia.1H NMR(400MHz,CDCl3):δ8.66(s,1H,Tetrazole-H),8.16(d,J
=8.8Hz, 2H, Ar-H), 7.86 (d, J=2.0Hz, 1H, Ar-H), 6.99~7.73 (m, 6H, Ar-H and NH), 4.77
(d, J=6.0Hz, 2H, CH2),4.24(s,3H,N-CH3),3.95(s,3H,OCH3).
Embodiment 2:
4mmol compound III is dissolved in 20mL methylene chloride, 20mmol pyridine is then added, is added thereto under room temperature
Enter intermediate II b 6mmol.It finishes, is heated to reflux 10 hours.Stop reaction, by reaction solution vacuum rotary steam to dry, gained remnants
Object obtains target compound Ib through column chromatographic isolation and purification.1H NMR(400MHz,CDCl3):δ8.66(s,1H,Tetrazole-
), H 8.16 (d, J=8.4Hz, 2H, Ar-H), 7.78~7.82 (m, 2H, Ar-H), 7.58 (d, J=8.8Hz, 2H, Ar-H),
7.12~7.24 (m, 3H, Ar-H and NH), 4.78 (d, J=6.0Hz, 2H, CH2),4.25(s,3H,N-CH3).
Embodiment 3:
6mmol compound III is dissolved in 20mL acetonitrile, 30mmol pyridine is then added.In being added thereto under condition of ice bath
II c 9mmol of mesosome, finishes, and is heated to reflux 13 hours.Stop reaction, by reaction solution vacuum rotary steam to dry, gained residue warp
Column chromatographic isolation and purification obtains target compound Ic.1H NMR(400MHz,CDCl3):δ8.66(s,1H,Tetrazole-H),
8.16 (d, J=8.4Hz, 2H, Ar-H), 7.58 (d, J=8.8Hz, 2H, Ar-H), 6.91~7.51 (m, 4H, Ar-H and
), NH 4.77 (d, J=6.0Hz, 2H, CH2),4.27(s,3H,N-CH3).
Embodiment 4:
10mmol compound III is dissolved in 25mL methylene chloride, 30mmol triethylamine is then added.To it under condition of ice bath
Middle addition intermediate II d 13mmol, finishes, and continues ice bath stirring 8 hours.Stop reaction, by reaction solution vacuum rotary steam to dry,
Gained residue obtains target compound Id through column chromatographic isolation and purification.1H NMR(400MHz,CDCl3):δ8.66(s,1H,
), Tetrazole-H 8.15 (d, J=8.8Hz, 2H, Ar-H), 7.56 (d, J=8.4Hz, 2H, Ar-H), 7.17 (brs, 1H,
), NH 4.73 (d, J=6.0Hz, 2H, CH2),4.15(s,3H,N-CH3),2.25(s,3H,CH3).
Embodiment 5:
20mmol compound III is dissolved in 30mL 1,38mmol sodium carbonate is then added in 2- dichloroethanes.Under condition of ice bath
Intermediate II e 18mmol is added thereto, finishes, continues to be stirred at room temperature 12 hours.Stop reaction, by reaction solution vacuum rotary steam
To doing, gained residue obtains target compound Ie through column chromatographic isolation and purification.1H NMR(400MHz,CDCl3):δ8.66(s,
1H, Tetrazole-H), 8.15 (d, J=8.8Hz, 2H, Ar-H), 7.56 (d, J=8.4Hz, 2H, Ar-H), 7.18 (brs,
1H, NH), 4.73 (d, J=6.0Hz, 2H, CH2),4.15(s,3H,N-CH3), 2.66 (q, J=7.6Hz, 2H, CH2),1.25
(t, J=7.6Hz, 3H, CH3).
Embodiment 6:
Sample screens the insecticidal activity of mythimna separata
The leaf dipping method for using international resistance Action Committee (IRAC) to propose: for examination target for mythimna separata, i.e., by appropriate corn
Leaf dries in the shade naturally after sufficiently infiltrating in the medical fluid prepared, is put into the culture dish for being lined with filter paper, connects mythimna separata 3 age mid-term larva 10
Head/ware is placed in 24-27 DEG C of observation ward and cultivates, investigation result after 48h.Polypide is touched with writing brush, it is reactionless to be considered as dead worm.Examination
Test 500 μ g/mL of concentration (medical fluid of other concentration can be diluted by the medical fluid of 500 μ g/mL and be obtained).
Insecticidal activity test result shows that all compounds show mythimna separate.It is 500 μ g/ in test concentrations
When mL (table 1), compound Ia-Ie is preferable to the insecticidal activity of mythimna separata, and killing rate are respectively 100%, 100%, 100%,
100% and 100%.
The preliminary insecticidal activity data of table 1.Ia-Ie
The above experimental data shows reasonably to combine tetrazole biphenyl structures one with pyrazole amide activity unit
It rises, obtained noval chemical compound shows good bioactivity, and the type compound is optional to be used as desinsection guide, makees further
Structure derivative and structure activity study.These experimental datas are also the molecule for continuing to be engaged in novel pyrazole amides compound from now on
Design, synthesis provide important theoretical foundation with bioactivity research.
The basic principles, main features and advantages of the present invention have been shown and described above.The technology of the industry
Personnel only illustrate the present invention it should be appreciated that the present invention is not limited by examples detailed above described in examples detailed above and specification
Principle, various changes and improvements may be made to the invention without departing from the spirit and scope of the present invention, these variation and
Improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention is by appended claims and its is equal
Object defines.
Claims (4)
1. a kind of pyrazol acid amide compounds I of biphenyl structures containing tetrazole, it is characterised in that structure are as follows:
2. a kind of preparation method of the pyrazol acid amide compounds of the biphenyl structures containing tetrazole as described in claim 1,
It is characterized in that method is as follows:
3. the pyrazol acid amide compounds I of the biphenyl structures containing tetrazole is in terms of preparing insecticide as described in claim 1
Purposes, it is characterised in that: the compound be used alone；Or used in a manner of Pesticidal combination, i.e., it is activity with compound I
Ingredient, in addition insecticides adjuvant commonly used in the art is processed into aqueous emulsion, suspending agent, water dispersion granule, missible oil.
4. the pyrazol acid amide compounds I of the biphenyl structures containing tetrazole is in terms of preparing insecticide as claimed in claim 3
Purposes, it is characterised in that: when compound I is used as the active constituent in insecticide, content in the insecticide can be
It is selected in the range of 0.1% to 99.5%.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110845487A (en) * | 2019-11-19 | 2020-02-28 | 南通大学 | 3- (triazole biphenyl methoxyl) pyrazole amide compound containing isoxazole structure and preparation method and application thereof |
| CN111253313A (en) * | 2020-02-26 | 2020-06-09 | 青岛恒宁生物科技有限公司 | Method for preparing pyrazole amide compounds by using microreactor |
| CN111592526A (en) * | 2020-06-20 | 2020-08-28 | 南通大学 | Preparation and application of 3- (chloropyridine methoxyaryl) -1-methylpyrazole compound containing azole heterocyclic structure |
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| CN1028713C (en) * | 1987-04-24 | 1995-06-07 | 三菱化成株式会社 | Pyrazole derivatve, insechicidal or miticidal composition |
| CN103081916A (en) * | 2011-11-02 | 2013-05-08 | 中国中化股份有限公司 | Application of pyrazole amide compound as agricultural bactericide |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1028713C (en) * | 1987-04-24 | 1995-06-07 | 三菱化成株式会社 | Pyrazole derivatve, insechicidal or miticidal composition |
| CN103081916A (en) * | 2011-11-02 | 2013-05-08 | 中国中化股份有限公司 | Application of pyrazole amide compound as agricultural bactericide |
| WO2013064079A1 (en) * | 2011-11-02 | 2013-05-10 | 中国中化股份有限公司 | Use of compound of pyrazole amides as agricultural fungicide |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110845487A (en) * | 2019-11-19 | 2020-02-28 | 南通大学 | 3- (triazole biphenyl methoxyl) pyrazole amide compound containing isoxazole structure and preparation method and application thereof |
| CN110845487B (en) * | 2019-11-19 | 2022-12-09 | 南通大学 | 3- (triazole biphenyl methoxyl) pyrazole amide compound containing isoxazole structure and preparation method and application thereof |
| CN111253313A (en) * | 2020-02-26 | 2020-06-09 | 青岛恒宁生物科技有限公司 | Method for preparing pyrazole amide compounds by using microreactor |
| CN111253313B (en) * | 2020-02-26 | 2023-09-26 | 青岛恒宁生物科技有限公司 | Method for preparing pyrazole amide compound by utilizing microreactor |
| CN111592526A (en) * | 2020-06-20 | 2020-08-28 | 南通大学 | Preparation and application of 3- (chloropyridine methoxyaryl) -1-methylpyrazole compound containing azole heterocyclic structure |
| CN111592526B (en) * | 2020-06-20 | 2022-06-10 | 南通大学 | Preparation and application of 3- (chloropyridine methoxyaryl) -1-methylpyrazole compound containing azole heterocyclic structure |
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Application publication date: 20190402 Assignee: DONGLI (NANTONG) CHEMICALS Co.,Ltd. Assignor: NANTONG University Contract record no.: X2022980025083 Denomination of invention: Pyrazole amides containing tetrazolium biphenyl structure and their preparation methods and applications Granted publication date: 20210302 License type: Common License Record date: 20221208 |
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