CN110407828A - A kind of pyrazoles -5- amide derivatives of the structure containing oxazole and its preparation method and application - Google Patents
A kind of pyrazoles -5- amide derivatives of the structure containing oxazole and its preparation method and application Download PDFInfo
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- CN110407828A CN110407828A CN201910763701.3A CN201910763701A CN110407828A CN 110407828 A CN110407828 A CN 110407828A CN 201910763701 A CN201910763701 A CN 201910763701A CN 110407828 A CN110407828 A CN 110407828A
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- pyrazoles
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- oxazole
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- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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Abstract
The present invention relates to pyrazoles -5- amide derivatives (I) of a kind of structure containing oxazole and its preparation method and application.It is condensed to yield by pyrazoles formoxyl chlorine (II) and oxazole methyl amine (III).A kind of pyrazoles -5- the amide derivatives of structure containing oxazole 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 pyrazoles -5- amide derivatives of the structure containing oxazole and
Preparation method and use.
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.
Substituted pyrazolecarboxylic ring is widely used in terms of agricultural production, and pyrazole compound has excellent desinsection, mite killing etc. living
Property, pyrazole heterocycle is widely introduced into agricultural chemical compound molecule, such as pyrazole amide insecticidal/acaricidal agent tebufenpyrad and azoles worm acyl
Amine has excellent killing activity to acarid, aphid etc..
Oxazole ring is also a kind of important nitrogen-containing heterocycle, and oxazole analog derivative is played an important role in pesticide field, closely
There are numerous research report oxazole analog derivatives that there is good insecticidal activity over year.
Therefore, it in order to further find the compound with excellent bioactivity from pyrazole amide analog derivative, uses
Pyrazole amide skeleton and oxazole unit are reasonably organically engaged togather by active group joining method, the invention discloses
One kind has the pyrazoles -5- amide derivatives of the structure containing oxazole of 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 structure containing oxazole, 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 -5- amides of structure containing oxazole
Derivative, with general formula I,
Preferably, a kind of pyrazoles -5- amide derivatives of structure containing oxazole have the following structure:
The second aspect of the present invention provides a kind of preparation side of the pyrazoles -5- amide derivatives of above-mentioned structure containing oxazole
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,
Preferably, the acid binding agent is selected from pyridine, triethylamine and n,N-diisopropylethylamine (DIPEA), the solvent choosing
From N,N-dimethylformamide (DMF), methylene chloride and chloroform.The heating reaction temperature is 0 DEG C -80 DEG C, when reaction
Between be 9-20 hours.
Preferably, a kind of pyrazoles -5- amide derivatives of structure containing oxazole the preparation method is as follows:
Wherein, 2- aryl oxazole -4- methylamine intermediate III can refer to document (Chin.Chem.Lett.2015,26,
672) method synthesizes to obtain；Pyrazol formyl chloride intermediate II reference literature (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。
A kind of pyrazoles -5- the amide derivatives of structure containing oxazole disclosed by the invention prevent harmful insect with excellent
Effect is controlled, 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:
4mmol compound III a is dissolved in 30mL chloroform, 20mmol pyridine is then added, under subsequent condition of ice bath to
Intermediate II a 6mmol is wherein added.It finishes, continues ice bath and react 9 hours.Stop reaction, by reaction solution vacuum rotary steam to dry,
Gained residue obtains target compound Ia through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3): δ 8.46~8.47 (m,
1H, Py-H), 8.03~8.08 (m, 2H, Ar-H), 7.93 (d, J=8.8Hz, 2H, Ar-H), 7.86~7.88 (m, 1H, Py-
), H 7.77 (s, 1H, Oxazole-H), 7.61 (s, 1H, Oxazole-H), 7.45 (d, J=8.8Hz, 2H, Ar-H), 7.34-
7.39(m,1H,Py-H),7.12-7.17(m,2H,Ar-H),6.96(s,1H,NH),6.29(s,1H,Pyrazole-H),5.29
(s,2H,CH2), 4.45 (d, J=5.2Hz, 2H, CH2).
Embodiment 2:
3mmol compound III a is dissolved in 30mL methylene chloride, then addition 2mL triethylamine, to it under subsequent condition of ice bath
Middle addition intermediate II b 5mmol.It finishes, heating reflux reaction 15 hours.Stop reaction, by reaction solution vacuum rotary steam to dry,
Gained residue obtains target compound Ib through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3): δ 8.46~8.47 (m,
1H, Py-H), 7.86~7.97 (m, 5H, Py-H, Ar-H and Oxazole-H), 7.61 (s, 1H, Oxazole-H), 7.51
(d, J=2.0Hz, 1H, Ar-H), 7.45 (d, J=8.4Hz, 2H, Ar-H), 7.32-7.38 (m, 2H, Py-H and Ar-H),
6.99(s,1H,NH),6.30(s,1H,Pyrazole-H),5.32(s,2H,CH2), 4.45 (d, J=5.6Hz, 2H, CH2).
Embodiment 3:
6mmol compound III b is dissolved in 30mL DMF, then addition 15mmol DIPEA, to it under subsequent condition of ice bath
Middle addition intermediate II a 7mmol.It finishes, is heated to 80 DEG C and reacts 20 hours.Stop reaction, by reaction solution vacuum rotary steam
To doing, gained residue obtains target compound Ic through column chromatographic isolation and purification.1H NMR(400MHz,CDCl3): δ 8.46~
8.48 (m, 1H, Py-H), 8.01~8.05 (m, 2H, Ar-H), 7.87~7.89 (m, 1H, Py-H), 7.72~7.82 (m, 3H,
Ar-H and Oxazole-H), 7.59 (s, 1H, Oxazole-H), 7.35~7.38 (m, 1H, Py-H), 7.21~7.26 (m,
1H, Ar-H), 7.09~7.15 (m, 3H, Ar-H and NH), 6.29 (s, 1H, Pyrazole-H), 5.28 (s, 2H, CH2),
4.45 (d, J=5.6Hz, 2H, CH2).
Embodiment 4:
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 2d.Polypide is touched with writing brush, it is reactionless to be considered as dead worm.Test
Concentration is 500 μ g/mL (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 insecticidal activity.It is 500 μ g/mL in proof load
When (table 1), chemical compounds I a, I b and I c are preferable to the insecticidal activity of mythimna separata, and killing rate are respectively 100%, 100% He
90%.
The preliminary insecticidal activity data of table 1.Ia-Ic
The above experimental data shows for substituted oxazoline structure and pyrazole amide activity unit to be reasonably combined, and obtains
New compound show good biological activity, these experimental datas are also that continue to be engaged in novel pyrazole amides from now on derivative
MOLECULE DESIGN, synthesis and the bioactivity research of object provide important structure choice mode and theoretical foundation.
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 pyrazoles -5- amide derivatives I of structure containing oxazole, it is characterised in that structure are as follows:
2. a kind of preparation method of the pyrazoles -5- amide derivatives I of the structure containing oxazole as described in claim 1, feature
It is that method is as follows:
3. a kind of pyrazoles -5- amide derivatives I of the structure containing oxazole as described in claim 1 is in terms of preparing insecticide
Purposes, it is characterised in that: the compound is used alone；Or used in a manner of Pesticidal combination, i.e., with compound I be activity at
Point, in addition insecticides adjuvant commonly used in the art is processed into aqueous emulsion, suspending agent, water dispersion granule, missible oil.
4. a kind of pyrazoles -5- amide derivatives I of the structure containing oxazole as claimed in claim 3 is in terms of preparing insecticide
Purposes, it is characterised in that: when compound I is used as the active constituent in insecticide, the content in the insecticide can be 0.1%
It is selected in the range of to 99.5%.
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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 |
| CN110845488A (en) * | 2019-11-19 | 2020-02-28 | 南通大学 | Preparation method and application of 3- (benzotriazole benzyloxy) pyrazole derivative containing aryl isoxazole |
| CN110922397A (en) * | 2019-11-19 | 2020-03-27 | 南通大学 | Preparation method and application of 3- (pyrazolylbiphenylmethoxy) pyrazole derivative containing substituted isoxazole unit |
| CN111253384A (en) * | 2020-04-01 | 2020-06-09 | 南通大学 | Preparation and application of 3-isoxazole methoxy pyrazole-5-amide containing substituted phenyl isoxazole unit |
| CN111285864A (en) * | 2020-04-01 | 2020-06-16 | 南通大学 | Preparation and application of p-chlorophenyl isoxazole methoxy pyrazole derivative containing isoxazole heterocyclic unit |
| CN111303140A (en) * | 2020-04-01 | 2020-06-19 | 南通大学 | Pyrazole derivative containing substituted isoxazole unit and preparation method and application thereof |
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Cited By (12)
| 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 |
| CN110845488A (en) * | 2019-11-19 | 2020-02-28 | 南通大学 | Preparation method and application of 3- (benzotriazole benzyloxy) pyrazole derivative containing aryl isoxazole |
| CN110922397A (en) * | 2019-11-19 | 2020-03-27 | 南通大学 | Preparation method and application of 3- (pyrazolylbiphenylmethoxy) pyrazole derivative containing substituted isoxazole unit |
| 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 |
| CN110922397B (en) * | 2019-11-19 | 2022-12-23 | 南通大学 | Preparation method and application of 3- (pyrazole biphenyl methoxy) pyrazole derivative containing substituted isoxazole unit |
| CN110845488B (en) * | 2019-11-19 | 2022-12-27 | 南通大学 | Preparation method and application of 3- (benzotriazole benzyloxy) pyrazole derivative containing aryl isoxazole |
| CN111253384A (en) * | 2020-04-01 | 2020-06-09 | 南通大学 | Preparation and application of 3-isoxazole methoxy pyrazole-5-amide containing substituted phenyl isoxazole unit |
| CN111285864A (en) * | 2020-04-01 | 2020-06-16 | 南通大学 | Preparation and application of p-chlorophenyl isoxazole methoxy pyrazole derivative containing isoxazole heterocyclic unit |
| CN111303140A (en) * | 2020-04-01 | 2020-06-19 | 南通大学 | Pyrazole derivative containing substituted isoxazole unit and preparation method and application thereof |
| CN111285864B (en) * | 2020-04-01 | 2022-10-11 | 南通大学 | Preparation and application of p-chlorophenyl isoxazole methoxy pyrazole derivative containing isoxazole heterocyclic unit |
| CN111303140B (en) * | 2020-04-01 | 2022-10-14 | 南通大学 | Pyrazole derivative containing substituted isoxazole unit and preparation method and application thereof |
| CN111253384B (en) * | 2020-04-01 | 2023-04-07 | 南通大学 | Preparation and application of 3-isoxazole methoxy pyrazole-5-amide containing substituted phenyl isoxazole unit |
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