CN110357872A - A kind of pyrazoles oxime compound and its preparation method and application of the structure of substituted-phenyl containing thiazole - Google Patents
A kind of pyrazoles oxime compound and its preparation method and application of the structure of substituted-phenyl containing thiazole Download PDFInfo
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- CN110357872A CN110357872A CN201910748952.4A CN201910748952A CN110357872A CN 110357872 A CN110357872 A CN 110357872A CN 201910748952 A CN201910748952 A CN 201910748952A CN 110357872 A CN110357872 A CN 110357872A
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- substituted
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- thiazole
- phenyl containing
- pyrazoles oxime
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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
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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)
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- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The present invention relates to pyrazoles oxime compounds (I) of a kind of structure of substituted-phenyl containing thiazole and its preparation method and application.It is condensed to yield with thiazole substituted-phenyl methyl chloride (II) and pyrazoles oxime (III).The pyrazoles oxime compound of the structure of substituted-phenyl containing thiazole has 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 oxime compound of the structure of substituted-phenyl containing thiazole
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.
Pyrazoles oximes structure is a kind of common biocidal activity segment, representation compound such as fenpyroximate:
Substituted thiazole is the Typical reactive segment in drug molecule and pesticide molecule, can effectively change compound
Physicochemical property, and the compound containing thiazole ring has stronger physiological activity in vivo.Thus set in new molecule
It may be effective active building block in meter.
By being expected to pyrazoles oxime and thiazole substituted-phenyl structures to form to obtain the noval chemical compound with insecticidal activity.
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
A kind of pyrazoles oxime compound of the structure of substituted-phenyl containing thiazole, 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 of structure of substituted-phenyl containing thiazole
Oxime compound, with general formula I,
Preferably, a kind of pyrazoles oxime compound of structure of substituted-phenyl containing thiazole has the following structure:
The second aspect of the present invention provides a kind of preparation of the pyrazoles oxime compound of above-mentioned structure of substituted-phenyl containing thiazole
Method comprising following steps:
Compound III is dissolved in organic solvent, acid binding agent is added, then in the mixing that intermediate II and a small amount of solvent is added
Liquid, last ice bath reaction a period of time, mother liquor are concentrated under reduced pressure, and gained residue isolates and purifies to obtain target compound.
Preferably, the acid binding agent is selected from triethylamine, sodium carbonate, potassium carbonate, sodium bicarbonate, cesium carbonate, the solvent choosing
From acetonitrile, N,N-dimethylformamide (DMF), acetone, dimethyl sulfoxide (DMSO).
Preferably, a kind of pyrazoles oxime compound of the structure of substituted-phenyl containing thiazole the preparation method is as follows:
Wherein, intermediate thiazole methyl chlorine synthesis reference literature report conventional method (Molecules, 2017,22,
1925)；Pyrazoles oxime intermediate synthesis reference literature report conventional method (J.Agric.Food Chem.2008,56,
10805-10810)。
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 oxime compound of structure of substituted-phenyl containing thiazole disclosed by the invention has 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:
In 100mL round-bottomed flask, 4mmol compound III a is dissolved in 30mL acetonitrile, 10mmol potassium carbonate is then added,
5mmol intermediate II a is added thereto under room temperature, finishes, is heated to reflux 12 hours.Reaction solution is cooled to room temperature, is taken out
Filter, mother liquor are concentrated under reduced pressure, and gained residue obtains target compound Ia through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3)
δ: 7.87 (s, 1H, CH=N), 7.83~7.86 (m, 2H, Ar-H), 7.35 (s, 1H, Thiazole-H), 7.08~7.11 (m,
2H, Ar-H), 6.94~6.98 (m, 2H, Ar-H), 6.82~6.86 (m, 2H, Ar-H), 5.30 (s, 2H, CH2),3.61(s,
3H,N-CH3),2.37(s,3H,CH3).
Embodiment 2:
In 100mL round-bottomed flask, 4mmol compound III a is dissolved in 30mL acetonitrile, 8mmol cesium carbonate, room is then added
6mmol intermediate II b is added under the conditions of temperature thereto, finishes, is heated to reflux 16 hours.Decompression boils off solvent, and residue is through column
Chromatography purifies to obtain I b of target compound；1H NMR(400MHz,CDCl3) δ: 7.87 (s, 1H, CH=N), 7.80~7.83
(m, 2H, Ar-H), 7.41 (s, 1H, Thiazole-H), 7.37 (d, J=8.4Hz, 2H, Ar-H), 7.08 (d, J=8.4Hz,
2H, Ar-H), 6.78 (d, J=8.4Hz, 2H, Ar-H), 5.32 (s, 2H, CH2),3.60(s,3H,N-CH3),2.39(s,3H,
CH3).
Embodiment 3:
In 100mL round-bottomed flask, 4mmol compound III b is dissolved in 30mL DMF, 12mmol bicarbonate is then added
Sodium is added 4mmol intermediate II b thereto under room temperature, finishes, be heated to reflux 18 hours.Decompression boils off solvent, residue
I c of target compound is obtained through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3) δ: 7.88 (s, 1H, CH=N), 7.83
(d, J=8.8Hz, 2H, Ar-H), 7.42 (s, 1H, Thiazole-H), 7.39 (d, J=8.8Hz, 2H, Ar-H), 7.34 (d, J
=2.4Hz, 1H, Ar-H), 7.07~7.10 (m, 1H, Ar-H), 6.60 (d, J=8.8Hz, 1H, Ar-H), 5.28 (s, 2H,
CH2),3.64(s,3H,N-CH3),2.36(s,3H,CH3).
Embodiment 4:
In 100mL round-bottomed flask, 6mmol compound III b is dissolved in 30mL acetone, 15mmol cesium carbonate is then added,
Intermediate II c 7mmol is added thereto under room temperature, finishes, temperature rising reflux reacts 20 hours.Stop reaction, filters, it is female
For liquid vacuum rotary steam to doing, gained residue obtains target compound Id through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3)
δ: 8.16~8.22 (m, 1H, Ar-H), 7.88 (s, 1H, CH=N), 7.64 (d, J=2.0Hz, 1H, Ar-H), 7.36 (s, 1H,
), Thiazole-H 6.88~7.10 (m, 3H, Ar-H), 6.60 (d, J=8.4Hz, 1H, Ar-H), 5.28 (s, 2H, CH2),
3.65(s,3H,N-CH3),2.36(s,3H,CH3).
Embodiment 5:
In 100mL round-bottomed flask, 5mmol compound III c is dissolved in 20mL DMF, is added thereto under room temperature
5mmol intermediate II b and 14mmol sodium carbonate, finishes, and is warming up to 90 DEG C, reacts 22 hours.Stop reaction, reaction solution is depressurized
For revolving to doing, gained residue obtains target compound Ie through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3)δ:7.89
(s, 1H, CH=N), 7.83 (d, J=8.4Hz, 2H, Ar-H), 7.42 (s, 1H, Thiazole-H), 7.36~7.40 (m, 4H,
), Ar-H 6.76 (d, J=8.8Hz, 2H, Ar-H), 5.29 (s, 2H, CH2),3.61(s,3H,N-CH3),2.37(s,3H,CH3).
Embodiment 6:
In 100mL round-bottomed flask, 5mmol compound III d is dissolved in 25mL DMSO, is added thereto under room temperature
8mmol intermediate II d and 30mmol triethylamine, finishes, and is warming up to 105 DEG C, reacts 12 hours.Stop reaction, reaction solution is subtracted
For pressure revolving to doing, gained residue obtains target compound If through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3)δ:
7.88 (s, 1H, CH=N), 7.76 (d, J=8.8Hz, 2H, Ar-H), 7.54 (d, J=8.4Hz, 2H, Ar-H), 7.43 (s, 1H,
), Thiazole-H 7.22 (d, J=8.8Hz, 2H, Ar-H), 6.81 (d, J=8.8Hz, 2H, Ar-H), 5.29 (s, 2H, CH2),
3.61(s,3H,N-CH3),2.37(s,3H,CH3).
Embodiment 7:
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
1~500 μ g/mL of concentration.
Insecticidal activity test result shows that all compounds all have preferable mythimna separate.It is 500 in proof load
When μ g/mL (table 1), the f of chemical compounds I a~I is respectively 100%, 100%, 100%, 100%, 100% to the killing effect of mythimna separata
With 100%.
The insecticidal activity data of table 1.Ia-If
The above experimental data shows reasonably to combine thiazole substituted-phenyl unit one with pyrazoles oxime 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 to continue to be engaged in the molecule of novel pyrazole oxime compound from now on to set
Meter, 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 pyrazoles oxime compound I of the structure of substituted-phenyl containing thiazole, it is characterised in that have such as flowering structure:
2. a kind of preparation method of the pyrazoles oxime compound I of the structure of substituted-phenyl containing thiazole, it is characterised in that method is as follows:
3. a kind of pyrazoles oxime compound I of the structure of substituted-phenyl containing thiazole as described in claim 1 is preparing insecticide side
The purposes in face, it is characterised in that: the compound is used alone；Or used in a manner of Pesticidal combination, i.e., it is to live with compound I
Property ingredient, 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 oxime compound I of the structure of substituted-phenyl containing thiazole as claimed in claim 3 is preparing insecticide side
The purposes in face, 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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