CN104151308A - Preparation method and application of 1,2,3-thiadiazole pyrazole oxime ether compounds - Google Patents
Preparation method and application of 1,2,3-thiadiazole pyrazole oxime ether compounds Download PDFInfo
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- CN104151308A CN104151308A CN201410315416.2A CN201410315416A CN104151308A CN 104151308 A CN104151308 A CN 104151308A CN 201410315416 A CN201410315416 A CN 201410315416A CN 104151308 A CN104151308 A CN 104151308A
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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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- 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
- A01N43/82—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 three ring hetero atoms
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Abstract
The invention relates to a preparation method and an application of 1,2,3-thiadiazole pyrazole oxime ether compounds. The preparation method comprises the following step: condensing parazole-containing hydroxyl oxime (II) with substituted substituent 5- chloromethyl-1,2,3- thiadiazole (III) to obtain the 1,2,3-thiadiazole pyrazole oxime ether compounds. The 1,2,3-thiadiazole pyrazole oxime ether compounds I have effective prevention and control effects on harmful insects and can be used for preparing pesticides in the fields such as agriculture and gardening.
Description
Technical field
The invention belongs to pesticide field, be specifically related to a kind of containing 1,2,3-thiadiazoles Pyrazole Oxime Esters and preparation method and purposes.
Background technology
The control of insect is the core realm of pesticide science research all the time, and being widely used of sterilant makes most insects obtain effective improvement.But along with the continuous expansion of sterilant application scale, the resistance problem of traditional pesticide species highlights day by day, adds the continuous appearance of new disease and pest, make the continuation research and development of novel pesticide become inevitable choice.
Pyrazole ring and 1,2,3-Thiadiazole are common in sterilant, miticide and sterilant, are the active building blocks of agricultural chemical compound design.By oxime ether, pyrazole ring and 1,2,3-Thiadiazole are connected to the compound that is expected to obtain having potential desinsection, sterilization and acaricidal activity.
Summary of the invention
The object of this invention is to provide for various insects and there is good prevention effect, and efficient, safety, an eco-friendly class are containing 1,2,3-thiadiazoles Pyrazole Oxime Esters, to meet Crop protection to efficient pesticides demand.
Another object of the present invention is to provide the preparation method of above-claimed cpd.
A further object of the invention is to provide above-claimed cpd in the purposes of preparing aspect sterilant.
The object of the invention can reach by following measures:
1,2, the 3-thiadiazoles Pyrazole Oxime Esters that contains of the present invention, is characterized in that possessing the structure as shown in formula I:
Wherein, on phenyl ring, the position of substitution represents with 2～4;
R
1for H, Cl, Br, F, CH
3, OCH
3, NO
2, CF
3or OCF
3;
R
2for methyl, ethyl, n-propyl, sec.-propyl or
wherein, R
3be selected from H, Cl, F, CH
3, OCH
3or CF
3)
This 1,2, the preparation method of 3-thiadiazoles Pyrazole Oxime Esters, it is characterized in that the compound shown in formula I by the compound shown in general formula II and general formula III under acid binding agent effect in aprotic polar solvent condensation obtain:
Wherein, on phenyl ring, the position of substitution represents with 2～4;
R
1for H, Cl, Br, F, CH
3, OCH
3, NO
2, CF
3or OCF
3;
R
2for methyl, ethyl, n-propyl, sec.-propyl or
wherein, R
3be selected from H, Cl, F, CH
3, OCH
3or CF
3)
Wherein acid binding agent is: pyridine, picoline, triethylamine, diisopropylethylamine (DIEA), 4-N, N-lutidine (DMAP), the one in salt of wormwood or cesium carbonate.The consumption of acid binding agent is generally 1.5～10 times of compound molar weight shown in general formula II.
Wherein aprotic polar solvent is: DMF (DMF), N,N-dimethylacetamide (DMA), DMSO, dioxane, the one in acetonitrile or hexamethylphosphoramide (HMPA).
The molar weight of its formula of III compound is 0.9～1.9 times of general formula II compound molar weight.
General formula II compound reference literature (Eur.J.Med.Chem., (2013) 60,376-385; Bioorg.Med.Chem.Lett., 2005 (15), 3307-3312.) synthetic the obtaining of method;
General formula III compound reference literature (Chinese invention patent: CN101891709) method is synthetic to be obtained.
Compound of Formula I has good control activity to insect, thereby compound of the present invention can be used as preparing sterilant, and then the plant such as protection agricultural, gardening.Described insect has lepidoptera pest as bollworm, beet armyworm, small cabbage moth, cabbage caterpillar, Cnaphalocrocis medinali(rice leaf roller) and striped rice borer etc., homoptera pest is as leafhopper, plant hopper, earthworm worm, aleyrodid etc., Diptera pest is as housefly, Liriomyza, mosquito class etc., the insects such as Orthoptera and Coleoptera etc.Certainly the harmful organism that, compound of the present invention can be prevented and treated is not limited to above-mentioned scope of giving an example.
Be used as the sterilant in the fields such as agricultural, gardening during when the compound of the present invention being represented by general formula I, can be used alone, or use in the mode of insect-killing composition, as taking formula I as activeconstituents, add that the conventional inert ingredient in this area is processed into aqueous emulsion, suspension agent, water dispersion granule, missible oil etc.
Conventional inert ingredient comprises: liquid vehicle, as water; Organic solvent is as toluene, dimethylbenzene, hexalin, methyl alcohol, butanols, ethylene glycol, acetone, dimethyl formamide, acetic acid, methyl-sulphoxide, animal and plant oil and lipid acid; Conventional superficiality agent, as emulsifying agent and dispersion agent, comprises anion surfactant, cats product, nonionogenic tenside and amphoterics.Other auxiliary agent, as wetting agent, thickening material etc.
When the compound of the present invention being represented by general formula I is used as the activeconstituents in sterilant, the content in described sterilant can be selected in 0.1% to 99.5% scope, and can determine suitable active component content according to dosage form and application process.Conventionally, contain 5% to 50% (weight percent, lower same) described activeconstituents in aqueous emulsion, preferably its content is 10% to 40%; In suspension agent, contain 5% to 50% activeconstituents, preferably its content is 5% to 40%.
For Utilization of pesticides of the present invention, can select conventional application method, as cauline leaf spraying, used for ponds, soil treatment and seed treatment etc.For example, when adopting cauline leaf when spraying, as the compound being represented by general formula I of activeconstituents can working concentration scope be aqueous emulsion, suspension agent, water dispersion granule, the missible oil of 1 to 1000 μ g/mL, preferably its concentration is 1 to 500 μ g/mL.
1,2, the 3-thiadiazoles Pyrazole Oxime Esters that contains disclosed by the invention has good prevention effect to harmful insect, therefore can be used to the sterilant for the preparation of fields such as agricultural, gardening.
Embodiment
For the ease of to further understanding of the present invention, the embodiment providing has below done more detailed description to it.These embodiment only are not used for limiting scope of the present invention or implementation principle for narration.
Embodiment 1:
Synthetic (the R in general formula II of Compound I a
1for 4-C (CH
3)
3, R in general formula III
2for CH
3)
In a reaction flask, add 5mmol compound ii, 5.5mmol compound III, 10mmol Carbon Dioxide caesium and 60mL DMF, be heated to 90 DEG C of reaction 20h.Stop heating, cooling, suction filtration, mother liquor revolves and steams to dry, and gained resistates, taking petrol ether/ethyl acetate (V:V=15:1) as eluent, separates to obtain target compound Ia, yield 71.4% by silica gel column chromatography;
1hNMR (400MHz, CDCl
3): δ 7.78 (s, 1H, CH=N), 7.31 (d, J=8.8Hz, 2H, Ar-H), 6.80 (d, J=8.4Hz, 2H, Ar-H), 5.22 (s, 2H, CH
2), 3.59 (s, 3H, N-CH
3), 2.65 (s, 3H, CH
3), 2.38 (s, 3H, CH
3), 1.30 (s, 9H ,-C (CH
3)
3).
Embodiment 2:
Synthetic (the R in general formula II of compounds ib
1for 4-OCF
3, R in general formula III
2for CH
3)
In a reaction flask, add 5mmol compound ii, 9mmol compound III, 10mmol DIPEA and 60mLDMSO, be heated to 90 DEG C of reaction 15h.Stop heating, cooling, mother liquor revolves and steams to dry, and gained resistates, taking petrol ether/ethyl acetate (V:V=15:1) as eluent, separates to obtain target compound Ib, yield 65.3% by silica gel column chromatography;
1h NMR (400MHz, CDCl
3): δ 7.80 (s, 1H, CH=N), 7.19 (d, J=8.4Hz, 2H, Ar-H), 6.91 (d, J=9.2Hz, 2H, Ar-H), 5.20 (s, 2H, CH
2), 3.63 (s, 3H, N-CH
3), 2.67 (s, 3H, CH
3), 2.39 (s, 3H, CH
3).
Embodiment 3:
Synthetic (the R in general formula II of Compound I c
1for 4-F, R in general formula III
2for CH
3)
In a reaction flask, add 5mmol compound ii, 7.5mmol compound III, 10mmol salt of wormwood and 60mL acetonitrile, heating reflux reaction 20 hours.Stop heating, cooling, filter, mother liquor revolves and steams to dry, and gained resistates, taking petrol ether/ethyl acetate (V:V=25:1) as eluent, separates to obtain target compound Ic, yield 60.5% by silica gel column chromatography;
1hNMR (400MHz, CDCl
3): δ 7.76 (s, 1H, CH=N), 6.96-7.00 (m, 2H, Ar-H), 6.82-6.85 (m, 2H, Ar-H), 5.20 (s, 2H, CH
2), 3.59 (s, 3H, N-CH
3), 2.64 (s, 3H, CH
3), 2.35 (s, 3H, CH
3).
Embodiment 4:
Synthetic (the R in general formula II of Compound I d
1for 3-F, R in general formula III
2for CH
3)
In a reaction flask, add 5mmol compound ii, 8mmol compound III, 11mmol DMAP and 50mL acetonitrile, heating reflux reaction 18 hours.Stop heating, cooling, filter, mother liquor revolves and steams to dry, and gained resistates, taking petrol ether/ethyl acetate (V:V=15:1) as eluent, separates to obtain target compound Id, yield 61.2% by silica gel column chromatography;
1hNMR (400MHz, CDCl
3): δ 7.80 (s, 1H, CH=N), 7.22-7.26 (m, 1H, Ar-H), 6.79-6.83 (m, 1H, Ar-H), 6.61-6.65 (m, 2H, Ar-H), 5.21 (s, 2H, CH
2), 3.60 (s, 3H, N-CH
3), 2.64 (s, 3H, CH
3), 2.37 (s, 3H, CH
3).
Embodiment 5:
Synthetic (the R in general formula II of Compound I e
1for 3-Cl, R in general formula III
2for CH
3)
In a reaction flask, add 5mmol compound ii, 8mmol compound III, 12mmol DIPEA and 50mL1,4-dioxane, is heated to 90 DEG C of reaction 20h.Stop heating, cooling, mother liquor revolves and steams to dry, and gained resistates, taking petrol ether/ethyl acetate (V:V=15:1) as eluent, separates to obtain target compound Ie, yield 62.8% by silica gel column chromatography;
1h NMR (400MHz, CDCl
3): δ 7.77 (s, 1H, CH=N), 7.16-7.20 (m, 1H, Ar-H), 7.04 (d, J=7.6Hz, 1H, Ar-H), 6.86 (s, 1H, Ar-H), 6.72 (d, J=8.0Hz, 1H, Ar-H), 5.17 (s, 2H, CH
2), 3.57 (s, 3H, N-CH
3), 2.60 (s, 3H, CH
3), 2.33 (s, 3H, CH
3).
Embodiment 6:
Synthetic (the R in general formula II of Compound I f
1for 4-I, R in general formula III
2for CH
3)
In a reaction flask, add 5mmol compound ii, 9mmol compound III, 10mmol DMAP and 50mL DMF, be heated to 90 DEG C of reaction 16h.Stop heating, cooling, mother liquor revolves and steams to dry, and gained resistates, taking petrol ether/ethyl acetate (V:V=20:1) as eluent, separates to obtain target compound If, yield 64.6% by silica gel column chromatography;
1h NMR (400MHz, CDCl
3): δ 7.77 (s, 1H, CH=N), 7.58 (d, J=8.8Hz, 2H, Ar-H), 6.65 (d, J=8.8Hz, 2H, Ar-H), 5.19 (s, 2H, CH
2), 3.59 (s, 3H, N-CH
3), 2.65 (s, 3H, CH
3), 2.36 (s, 3H, CH
3).
Embodiment 7:
Synthetic (the R in general formula II of Compound I g
1for 2-CH
3, R in general formula III
2for n-Pr)
In a reaction flask, add 5mmol compound ii, 7.5mmol compound III, 10mmol Anhydrous potassium carbonate and 60mL acetonitrile, be heated to the 20h that refluxes.Stop heating, cooling, suction filtration, mother liquor revolves and steams to dry, and gained resistates, taking petrol ether/ethyl acetate (V:V=15:1) as eluent, separates to obtain target compound Ia by silica gel column chromatography.Faint yellow oily matter, yield 54.6%,
1h NMR (400MHz, CDCl
3): δ 7.71 (s, 1H, CH=N), 7.22 (d, J=6.4Hz, 1H, Ar-H), 7.00～7.11 (m, 2H, ArH), 6.53 (d, J=8.0Hz, 1H, Ar-H), 5.22 (s, 2H, CH
2), 3.60 (s, 3H, N-CH3), 2.97 (t, J=7.2Hz, 2H, CH
2), 2.39 (s, 3H, CH
3), 2.37 (s, 3H, CH3), 1.76～1.86 (m, 2H, CH
2), 0.98 (t, J=7.2Hz, 3H, CH
3).
Embodiment 8:
The insecticidal activity screening of sample to aphid
Take a certain amount of medicine, adding 1mL DMSO dissolves, add two of emulsifying agent TW-20, fully stir with glass stick, it is dissolved mutually, add again after appropriate distilled water, again fully stir, be made into the liquid (liquid of other concentration can be obtained by the liquid dilution of 500 μ g/mL) of 500 μ g/mL.Plant with aphid was flooded for 5 seconds in above-mentioned liquid, get rid of unnecessary liquid, plant is inserted in water-absorbing sponge, and cover plant with lens, with gauze sealing, after 24 hours and 48 hours, check respectively mortality ratio and statistical correction mortality ratio, each compound repeats 3 times, contrast only adds emulsifying agent and solvent in distilled water, stirs.
Embodiment 9:
Sample is to becoming the acaricidal activity screening of mite
When the dwarf bean being for experiment grows to two true leaves, selection growing way is relatively more neat, leaf area 5cm
2the plant of left and right, plant height 10cm left and right connects worm, and every strain worm amount is controlled at 120 left and right.Connect worm and after 24 hours, carry out chemicals treatment.Take a certain amount of medicine sample in 100mL beaker, add 1mL acetone (or other applicable solvent).Add two emulsifying agent TW-20, fully stir with glass stick, it is dissolved mutually, then after adding distil water, again fully stir, be made into the liquid of 200 μ g/mL.Chemicals treatment adopts plant pickling process, the plant with tetranychid is flooded for 5 seconds in above-mentioned liquid, and after plant is taken out from liquid, shake, gets rid of unnecessary liquid gently, then moves in water planting cylinder, places at room temperature.Difference check result after 24 hours and 48 hours.Each compound repeats 3 times, averages.
Embodiment 10:
The insecticidal activity screening of sample to small cabbage moth
The leaf dipping method that adopts international resistance Action Committee (IRAC) to propose.On analytical balance, take 2mg medicine sample in 10mL small beaker, add 50 μ L dimethyl formamides (for analytical pure) and dissolve, add 10mL water and make 200 μ g/mL liquids.With straight peen ophthalmology tweezers dippings cabbage leaves, time 2-3 second, get rid of remaining liquid.Each 1, totally 3, each sample.Be successively placed in treatment paper by sample flag sequence.After liquid is dry, put into the long straight type pipe of the markd 10cm of tool, access diamondback moth larvae in 2 age, builds the mouth of pipe with gauze.Test is processed and is placed in standard treatment chamber, 48h check result (chitin inhibitor will be observed 4 days).
The insecticidal activity data (Mortality, %) of table 1.Ia-Ig
The demonstration of insecticidal activity test result, part target compound shows good desinsection and acaricidal activity, in the time that test concentrations is 200 μ g/mL, its chemical compounds I a, I b, I c, I d, I e and I f are respectively 95,100 to the prevention effect of aphid, 99,98,100 and 95%; In the time that test concentrations is 200 μ g/mL, its chemical compounds I a, I c and I e are fine to the inhibiting rate of small cabbage moth, all reach 100%; In the time that test concentrations is 200 μ g/mL, its compoundsⅰb, I d and I f are to becoming the inhibiting rate of mite to be respectively 80,80 and 90%.Above data show, introduce 1,2 of replacement in pyrazoles oxime activity unit structure, and 3-thiadiazoles heterocycle has expanded its insecticidal spectrum, and part of compounds can be used as agricultural chemicals lead compound and makes further Exploration and Research.
Claims (7)
1. one kind contains 1,2,3-thiadiazoles Pyrazole Oxime Esters, it is characterized in that possessing the structure as shown in formula I:
Wherein, on phenyl ring, the position of substitution represents with 2～4;
R
1for H, Cl, Br, F, CH
3, OCH
3, NO
2, CF
3or OCF
3;
R
2for methyl, ethyl, n-propyl, sec.-propyl or
wherein, R
3be selected from H, Cl, F, CH
3, OCH
3or CF
3.
2. one kind as claimed in claim 1ly contains 1,2, the preparation method of 3-thiadiazoles Pyrazole Oxime Esters, is characterized in that, the compound shown in formula I by the compound shown in general formula II and general formula III under acid binding agent effect in aprotic polar solvent condensation obtain:
Wherein, on phenyl ring, the position of substitution represents with 2～4;
R
1for H, Cl, Br, F, CH
3, OCH
3, NO
2cF
3or OCF
3;
R
2for methyl, ethyl, n-propyl, sec.-propyl or
wherein, R
3be selected from H, Cl, F, CH
3, OCH
3or CF
3.
3. preparation method as claimed in claim 2, wherein acid binding agent is: pyridine, picoline, triethylamine, diisopropylethylamine (DIEA), 4-N, N-lutidine (DMAP), the one in salt of wormwood or cesium carbonate; The consumption of acid binding agent is generally 1.5～10 times of compound molar weight shown in general formula II.
4. preparation method as claimed in claim 2, wherein aprotic polar solvent is: DMF (DMF), N,N-dimethylacetamide (DMA), DMSO, dioxane, the one in acetonitrile or hexamethylphosphoramide (HMPA).
5. preparation method as claimed in claim 2, the molar weight of its formula of III compound is 0.9～1.9 times of general formula II compound molar weight.
6. compound as claimed in claim 1, in the purposes of preparing aspect sterilant, is characterized in that: this compound uses separately; Or use in the mode of insect-killing composition, taking formula I as activeconstituents, add that the conventional inert ingredient in this area is processed into aqueous emulsion, suspension agent, water dispersion granule, missible oil etc.
7. pyridine phenyl ether compound as claimed in claim 6 is in the purposes of preparing aspect sterilant, it is characterized in that: when the compound of the present invention being represented by general formula I is used as the activeconstituents in sterilant, the content in described sterilant can be selected in 0.1% to 99.5% scope.
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Cited By (10)
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| CN105753856A (en) * | 2016-03-08 | 2016-07-13 | 南通大学 | Preparation and application of difluoromethyl pyrazole compound comprising 1,3,4-oxadiazole structure |
| CN106432081A (en) * | 2016-07-26 | 2017-02-22 | 南通大学 | Preparation method and application of pyrazole oxime ether compound containing 4-Cl-3-ethyl-1-methylpyrazole structure |
| CN107428694A (en) * | 2015-03-19 | 2017-12-01 | 杜邦公司 | Antifungal pyrazoles |
| CN109879867A (en) * | 2019-03-06 | 2019-06-14 | 南通大学 | A kind of preparation and application of the Pyrazole Oxime Esters of the oxazole of aryl containing 5- structure |
| CN110003184A (en) * | 2019-02-01 | 2019-07-12 | 南通大学 | The preparation and application of pyrazoles oxime derivatives of the one kind containing 1,2,4- triazole structures |
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| CN107428694A (en) * | 2015-03-19 | 2017-12-01 | 杜邦公司 | Antifungal pyrazoles |
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| CN109879867A (en) * | 2019-03-06 | 2019-06-14 | 南通大学 | A kind of preparation and application of the Pyrazole Oxime Esters of the oxazole of aryl containing 5- structure |
| CN109879867B (en) * | 2019-03-06 | 2022-03-01 | 南通大学 | Preparation and application of pyrazole oxime ether compound containing 5-aryl oxazole structure |
| CN110128410A (en) * | 2019-04-30 | 2019-08-16 | 南通大学 | Pyrazole Oxime Esters of the structure containing difluoromethyl pyrazole and its preparation method and application |
| CN110092776A (en) * | 2019-04-30 | 2019-08-06 | 南通大学 | The pyrazoles oxime ester compound and its preparation method and application of the connection polyfluoro pyrrazole structure containing pyridine |
| CN110092776B (en) * | 2019-04-30 | 2021-09-07 | 南通大学 | Pyrazole oxime ester compound containing pyridine-difluoride pyrazole structure and preparation method and application thereof |
| CN110357872A (en) * | 2019-08-14 | 2019-10-22 | 南通大学 | A kind of pyrazoles oxime compound and its preparation method and application of the structure of substituted-phenyl containing thiazole |
| CN110437221A (en) * | 2019-08-27 | 2019-11-12 | 南通大学 | The pyrazole derivatives and its preparation method and application of the oxadiazoles unit of methyl containing aryloxy group |
| CN110437221B (en) * | 2019-08-27 | 2021-11-16 | 南通大学 | Pyrazole derivative containing aryloxy methyl oxadiazole unit and preparation method and application thereof |
| CN111635399A (en) * | 2020-07-01 | 2020-09-08 | 南通大学 | Pyrazole derivative containing thiadiazole heterocyclic unit and preparation method and application thereof |
| CN111635399B (en) * | 2020-07-01 | 2022-05-03 | 南通大学 | Pyrazole derivative containing thiadiazole heterocyclic unit and preparation method and application thereof |
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