CN107445947B - One kind containing the pyrazoles oxime ether compound and its preparation method and application of 1,2,3- triazole biphenyl structures - Google Patents
One kind containing the pyrazoles oxime ether compound and its preparation method and application of 1,2,3- triazole biphenyl structures Download PDFInfo
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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Abstract
The present invention relates to a kind of pyrazoles oxime ether compounds (I) and its preparation method and application for containing 1,2,3- triazole biphenyl structures.It is condensed to yield with 1,2,3- triazole Biphenylmethyl chlorine (II) with pyrazolyl aldoxime (III).The pyrazoles oxime ether compound for containing 1,2,3- triazole biphenyl structures has effective control efficiency to harmful insect, which is used to prepare 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 9 oxime derivate of biphenyl structures containing triazole and
Preparation method and use.
Background technique
Prevention and treatment and inhibition insect pest are the core contents of pesticide science research field.Various types of insecticides are widely used
Insect pest is set to be constantly in controllable state.But the scale used with insecticide constantly expands and uses the gradually increasing of time
Long, pest starts to develop drug resistance to traditional pesticide gradually or even cross-resistance.In addition as new insect pest constantly goes out
It is existing, so that the research and development that continues of novel pesticide becomes inevitable choice.
Nitrogen-containing heterocycle compound is widely used in terms of agricultural production, and Pyrazole Oxime Esters important contain as a kind of
Nitrogen heterocyclic has excellent desinsection, mite killing isoreactivity, and wherein typicalness compound has fenpyroximate, in pesticide field
It plays an important role in terms of desinsection.
In recent years, there are some researchs to report pyrazol oxime ether derivatives and show good desinsection and acaricidal action.Such as
The pyrazoles oxime compound A and B containing 1,3,4- thiadiazoles heterocycle structures of the synthesis such as Dai shows aphid, acarid and diamondback moth etc.
Excellent desinsection, acaricidal activity out, when proof load is 100 μ g/mL, compound A and B is to the killing activity of aphid
100%；Compound A and B is respectively 100% and 90% to the killing activity of acarid；Killing rate of the compound A and B to diamondback moth
Respectively 60% and 100% (Bioorg.Med.Chem.Lett.2016,26,3818-3821).
1,2,3- 3-triazole compounds are also a kind of important nitrogen-containing heterocycle compound, it may have good bioactivity,
As Mao et al. compound C reported shows preferable preventive effect (J.Pestic.Sci.2015,40,138-142) to mosquito.
Therefore, it in order to further find the compound with excellent bioactivity from Pyrazole Oxime Esters, uses
1,2,3- triazole group and pyrazoles oxime skeleton are reasonably engaged togather by active group joining method, the invention discloses
One kind has the pyrazoles oxime ether compound containing 1,2,3- triazole biphenyl structures 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
One kind contains the pyrazoles oxime ether derivatives of 1,2,3- triazole biphenyl structures, to meet crop protection to efficient pesticides demand.
It is a further object of the present invention to provide the preparation methods of above compound.
A further object of the present invention is to provide purposes of the above compound in terms of preparing insecticide.
In order to solve the above technical problems, the first aspect of the present invention provides one kind containing 1,2,3- triazole biphenyl structures
Pyrazoles oxime ether derivatives, with general formula I,
Preferably, the pyrazoles oxime ether derivatives containing 1,2,3- triazole biphenyl structures have the following structure:
The present invention provides the preparation method of the above-mentioned pyrazoles oxime ether derivatives for containing 1,2,3- triazole biphenyl structures, special
Sign is to include the following steps:
Compound III is dissolved in organic solvent, acid binding agent is added, then intermediate II, finally heated one section of reaction is being added
Time filters after being cooled to room temperature reaction solution, and mother liquor is concentrated under reduced pressure, and gained residue obtains target through column chromatographic isolation and purification
Compound,
Wherein, R:F；Cl；Br,I；H；CH3；OCH3；OCF3。
Preferably, the acid binding agent is selected from sodium carbonate, cesium carbonate, sodium bicarbonate, pyridine, triethylamine, potassium carbonate；It is described to have
Solvent is selected from dimethyl sulfoxide (DMSO), acetone, tetrahydrofuran (THF), acetonitrile, Isosorbide-5-Nitrae-dioxane, N, N- dimethyl methyl
Amide (DMF), n,N-dimethylacetamide (DMA), 2- butanone.Heating reaction temperature is 45 DEG C~120 DEG C, the reaction time 8
Hour~30 hours.
Preferably, the preparation method of the pyrazoles oxime ether derivatives containing 1,2,3- triazole biphenyl structures, including walk as follows
It is rapid:
Wherein, intermediate 1,2,3- triazole Biphenylmethyl chlorine can refer to document (J.Med.Chem.1998,41,2390-
2410；Chin.Chem.Lett.2014,25,1014-1016 method) synthesizes to obtain；The synthesis of intermediate pyrazole formaldoxime is joined
According to conventional method (Bioorg.Med.Chem.Lett.2016,26,4504-4507) reported in the literature.
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 pyrazoles oxime ether derivatives of the biphenyl structures of triazole containing 1,2,3- disclosed by the invention have harmful insect excellent
Good 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 a is dissolved in 25mL DMSO, 8mmol sodium carbonate is then added, is added thereto under room temperature
Enter intermediate II 6mmol, finish, is heated to 120 DEG C and reacts 16 hours.Reaction solution is cooled to room temperature, is filtered, mother liquor decompression is dense
Contracting, gained residue obtain target compound I through column chromatographic isolation and purificationa；1H NMR(400MHz,CDCl3): δ 8.02 (d, J=
8.4Hz, 2H, Ar-H), 7.81 (s, 3H, Triazole-H and C=NH), 7.58~7.61 (m, 1H, Ar-H), 7.37 (d, J
=8.4Hz, 2H, Ar-H), 7.16~7.20 (m, 1H, Ar-H), 6.94~6.98 (m, 1H, Ar-H), 6.62~6.64 (m, 1H,
Ar-H),5.01(s,2H,CH2),3.63(s,3H,CH3),2.35(s,3H,CH3).
Embodiment 2:
3mmol compound III b is dissolved in 25mL acetone, 5mmol cesium carbonate is then added, is added thereto under room temperature
Intermediate II 3mmol, finishes, temperature rising reflux, reacts 10 hours.Reaction solution is cooled to room temperature, is filtered, mother liquor is concentrated under reduced pressure,
Gained residue obtains target compound I through column chromatographic isolation and purificationb；1H NMR(400MHz,CDCl3): δ 8.02 (d, J=
8.4Hz, 2H, Ar-H), 7.83 (s, 1H, N=CH), 7.81 (d, J=2.4Hz, 2H, Triazole-H), 7.39 (d, J=
8.4Hz, 2H, Ar-H), 6.61~7.26 (m, 4H, Ar-H), 5.02 (s, 2H, CH2),3.61(s,3H,CH3),2.36(s,3H,
CH3).
Embodiment 3:
7mmol compound III c is dissolved in 30mL THF, 8mmol intermediate II and 8mmol is added thereto under room temperature
Sodium bicarbonate finishes, and is warming up to 45 DEG C, reacts 13 hours.Stop reaction, by reaction solution vacuum rotary steam to dry, gained residue
Target compound I is obtained through column chromatographic isolation and purificationc；1H NMR(400MHz,CDCl3): δ 8.02 (d, J=8.4Hz, 2H, Ar-H),
7.83 (s, 1H, N=CH), 7.81 (s, 2H, Triazole-H), 7.38 (d, J=8.4Hz, 2H, Ar-H), 6.74~7.23 (m,
4H,Ar-H),5.02(s,2H,CH2),3.60(s,3H,CH3),2.36(s,3H,CH3).
Embodiment 4:
5mmol compound III d is dissolved in 35mL acetonitrile, under room temperature thereto be added 8mmol intermediate II and
13mmol pyridine finishes, and heating reflux reaction 16 hours.Stop reaction, by reaction solution vacuum rotary steam to dry, gained residue warp
Column chromatographic isolation and purification obtains target compound Id；1H NMR(400MHz,CDCl3): δ 8.03 (d, J=8.4Hz, 2H, Ar-H),
7.81 (s, J=2.4Hz, 3H, Triazole-H and N=CH), 7.39 (d, J=8.8Hz, 2H, Ar-H), 6.96~7.01
(m, 2H, Ar-H), 6.82~6.86 (m, 2H, Ar-H), 5.03 (s, 2H, CH2),3.61(s,3H,CH3),2.36(s,3H,
CH3).
Embodiment 5:
4mmol compound III e is dissolved in 30mL acetonitrile, 7mmol triethylamine is then added, is added thereto under room temperature
Intermediate II 4.4mmol, finishes, and temperature rising reflux reacts 17 hours.Stop reaction, by reaction solution vacuum rotary steam to doing, gained is residual
Excess obtains target compound Ie through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3): δ 8.03 (d, J=8.4Hz, 2H,
), Ar-H 7.81 (s, 3H, Triazole-H, N=CH), 7.37~7.41 (m, 4H, Ar-H), 6.76 (d, J=8.8Hz, 2H,
Ar-H),5.01(s,2H,CH2),3.61(s,3H,CH3),2.36(s,3H,CH3).
Embodiment 6:
5mmol compound III f is dissolved in 30mL Isosorbide-5-Nitrae-dioxane, 25mmol potassium carbonate is then added, under room temperature
Intermediate II 6mmol is added thereto, finishes, is warming up to 80 DEG C, reacts 8 hours.Stop reaction, filters, mother liquor vacuum rotary steam
To doing, gained residue obtains target compound If through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3):δ8.03(d,J
=8.4Hz, 2H, Ar-H), 7.81 (s, 3H, Triazole-H and N=CH), 7.58 (d, J=8.8Hz, 2H, Ar-H),
7.39 (d, J=8.4Hz, 2H, Ar-H), 6.65 (d, J=8.8Hz, 2H, Ar-H), 5.01 (s, 2H, CH2), 3.59 (s, 3H,
CH3), 2.35 (s, 3H, CH3).
Embodiment 7:
5mmol compound III g is dissolved in 20mL DMF, 20mmol sodium carbonate is then added, is added thereto under room temperature
Enter intermediate II 6mmol, finish, be warming up to 100 DEG C, reacts 30 hours.Stop reaction, filters, mother liquor vacuum rotary steam to dry, institute
It obtains residue and obtains target compound Ig through column chromatographic isolation and purification；1H NMR (400MHz, CDCl3): δ 8.01 (d, J=
8.4Hz, 2H, Ar-H), 7.83 (s, 1H, NCH), 7.81 (s, 2H, Triazole-H), 7.39 (d, J=8.4Hz, 2H, Ar-H),
7.07~7.32 (m, 3H, Ar-H), 6.88 (d, J=8.0Hz, 2H, Ar-H), 5.03 (s, 2H, CH2),3.59(s,3H,CH3),
2.61(s,3H,CH3).
Embodiment 8:
4mmol compound III h is dissolved in 25mL DMA, 6mmol sodium carbonate is then added, is added thereto under room temperature
Intermediate II 5mmol, finishes, and is warming up to 80 DEG C, reacts 26 hours.It filters, mother liquor vacuum rotary steam is to doing, and gained residue is through column
Chromatography purifies to obtain target compound Ih；1H NMR (400MHz, CDCl3): δ 8.01 (d, J=8.4Hz, 2H, Ar-H),
7.82 (s, 1H, N=CH), 7.80 (s, 2H, Triazole-H), 7.39 (d, J=8.4Hz, 2H, Ar-H), 7.08 (d, J=
8.4Hz, 2H, Ar-H), 6.77 (d, J=8.8Hz, 2H, Ar-H), 5.04 (s, 2H, CH2), 3.58 (s, 3H, CH3), 2.36 (s,
3H,CH3),2.30(s,3H,CH3).
Embodiment 9:
5mmol compound III i is dissolved in 20mL acetonitrile, 30mmol potassium carbonate is then added, is added thereto under room temperature
Enter intermediate II 8mmol, finish, temperature rising reflux reacts 28 hours.It filters, mother liquor vacuum rotary steam is to doing, and gained residue is through column
Chromatography purifies to obtain target compound Ii；1H NMR(400MHz,CDCl3): δ 8.02 (d, J=8.8Hz, 2H, Ar-H),
7.80 (d, J=6.0Hz, 3H, Triazole-H and N=CH), 7.41 (d, J=8.8Hz, 2H, Ar-H), 6.82 (s, 4H,
Ar-H),5.05(s,2H,CH2),3.76(s,3H,OCH3),3.62(s,3H,CH3),2.36(s,3H,CH3).
Embodiment 10:
5mmol compound III j is dissolved in 20mL 2- butanone, 5mmol sodium bicarbonate is then added, under room temperature to it
Middle addition intermediate II 4mmol, finishes, and temperature rising reflux reacts 20 hours.It filters, mother liquor vacuum rotary steam to dry, gained residue
Target compound Ij is obtained through column chromatographic isolation and purification；1H NMR(400MHz,CDCl3): δ 8.02 (d, J=8.8Hz, 2H, Ar-
H), 7.83 (s, 1H, N=CH), 7.81 (s, 2H, Triazole-H), 7.39 (d, J=8.8Hz, 2H, Ar-H), 7.15 (d, J=
9.2Hz, 2H, Ar-H), 6.88 (d, J=9.2Hz, 2H, Ar-H), 5.00 (s, 2H, CH2),3.63(s,3H,CH3),2.36(s,
3H,CH3).
Embodiment 14:
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 3d.Polypide is touched with writing brush, it is reactionless to be considered as dead worm.Test
500 μ g/mL of concentration.
Embodiment 15:
Sample screens the insecticidal activity of aphid and brown paddy plant hopper
The spray-on process for using international resistance Action Committee (IRAC) to propose: for examination target for aphid and Tetranychus cinnabarinus, i.e.,
The spraying treatment under Potter spray tower by the Broad Bean Leaves for being connected to aphid and the rice seedlings for being connected to Tetranychus cinnabarinus respectively, after processing
Aphid and Tetranychus cinnabarinus are placed in 24-27 DEG C of observation ward and cultivate, and aphid is placed in 20-22 DEG C of observation ward and cultivates, and knot is investigated after 48h
Fruit.Polypide is touched with writing brush, it is reactionless to be considered as dead worm.500 μ g/mL of experimental concentration.
Insecticidal activity test result shows that all compounds all have preferable insecticidal activity.It is 500 μ in test concentrations
When g/mL (table 1), the j of chemical compounds I a~I is 100% to the killing effect of mythimna separata；The j of chemical compounds I a~I is living to the desinsection of aphid
Property is respectively 90%, 100%, 100%, 100%, 100%, 100%, 100%, 100%, 100% and 100%；Chemical compounds I a-
I j all shows preferable insecticidal activity to Tetranychus cinnabarinus, and inhibiting rate is respectively 90%, 100%, 100%, 100%, 90%,
80%, 100%, 100%, 100% and 100%.When test concentrations are 100 μ g/mL (table 1), chemical compounds I a, I b, I d, I e, I
F, I g, I h, I i and I j are respectively 100%, 80%, 80%, 80%, 100%, 80%, 100% to the killing effect of mythimna separata,
100% and 80%；Chemical compounds I b, I c, I d, I e, I f, I g, I i and I j are respectively 90%, 90% to the insecticidal activity of aphid,
90%, 90%, 95%, 95%, 100% and 90%；Chemical compounds I b and I g is 90% to the inhibiting rate of Tetranychus cinnabarinus.It is testing
When concentration is 20 μ g/mL (table 1), I b, I d, I f, I h and I i are respectively 70%, 60%, 100% to the killing effect of mythimna separata,
80% and 80%；Chemical compounds I d, I f and I i are 80%, 70% and 80% to the insecticidal activity of aphid.
The insecticidal activity data of table 1.Ia-Ij
The above experimental data shows reasonably to hold in the mouth 1,2,3- triazole biphenyl structures unit and pyrazoles oxime activity unit
It is connected together, obtains new compound and show excellent insecticidal activity, the type compound is optional to be used as desinsection guide, makees
Further structure derivative and bioactivity research.These experimental datas are also to continue to be engaged in the conjunction of novel pyrazole oxime ether derivatives from now on
Important theoretical foundation is provided at 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. the pyrazoles oxime ether compound I that one kind contains 1,2,3- triazole biphenyl structures, it is characterised in that structure are as follows:
2. a kind of preparation side of the pyrazoles oxime ether compound I of the biphenyl structures of triazole containing 1,2,3- as described in claim 1
Method, it is characterised in that method is as follows:
3. the pyrazoles oxime ether compound I of the biphenyl structures of triazole containing 1,2,3- kills mythimna separata in preparation as described in claim 1
With the purposes in terms of Tetranychus cinnabarinus drug, it is characterised in that: the compound is used alone；Or it is with compound I in claim 1
Active constituent, in addition insecticides adjuvant commonly used in the art is processed into the desinsection of aqueous emulsion, suspending agent, water dispersion granule, missible oil
The mode of composition uses.
4. the pyrazoles oxime ether compound I of the biphenyl structures of triazole containing 1,2,3- kills mythimna separata in preparation as claimed in claim 3
With the purposes in terms of Tetranychus cinnabarinus drug, it is characterised in that: compound I described in claim 1, which is used as, kills mythimna separata and cinnabar leaf
When the active constituent of mite drug, in the range of the content killed in mythimna separata and Tetranychus cinnabarinus drug is 0.1% to 99.5%
It is selected.
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| CN106946782A (en) * | 2017-02-08 | 2017-07-14 | 南通大学 | Pyrazole Oxime Esters of the biphenyl structures containing pyrazoles and its production and use |
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