CN104557710A - Preparation and application of pyrazole oxime compound containing multi-substituent pyrazole structure - Google Patents
Preparation and application of pyrazole oxime compound containing multi-substituent pyrazole structure Download PDFInfo
- Publication number
- CN104557710A CN104557710A CN201410820503.3A CN201410820503A CN104557710A CN 104557710 A CN104557710 A CN 104557710A CN 201410820503 A CN201410820503 A CN 201410820503A CN 104557710 A CN104557710 A CN 104557710A
- Authority
- CN
- China
- Prior art keywords
- compound
- pyrazole
- substituent
- pyrazoles
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 0 CC(CC1)**1c1ccc(CON=Cc(c(C)n[n]2*)c2Oc2ccccc2)cc1 Chemical compound CC(CC1)**1c1ccc(CON=Cc(c(C)n[n]2*)c2Oc2ccccc2)cc1 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Landscapes
- 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)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention relates to a preparation and an application of a pyrazole oxime compound (I) containing a multi-substituent pyrazole structure. The pyrazole oxime compound is obtained by condensation of pyrazole hydroxyl oxime (II) and a 1,3-dimethyl-5-aryloxy-pyrazole-4-methyl bromide(chloride) intermediate (II). The pyrazole oxime compound (I) containing the multi-substituent pyrazole structure has effective prevention and control effects on harmful insects and can be used for preparing insecticides in the fields of agriculture, gardens and the like.
Description
Technical field
The invention belongs to pesticide field, be specifically related to a kind of pyrazoles oxime compounds containing multi-substituent pyrrazole structure and its production and use.
Background technology
The control of insect is the key areas of pesticide science research all the time, and widely using of sterilant makes most of insect obtain effectively preventing.
Pyrazoles oximes structure is the common biocidal activity fragment of a class, and wherein representative compound fenpyroximate, it can be used to prevent and treat multiple phytophagy mite, as red spider, fistula mite, leeched line mite etc.
Along with the widespread use of fenpyroximate, regional and national at some, some insect creates resistance to fenpyroximate, and meanwhile, new insect pest constantly occurs again, and this makes the continuation of novel pesticide research and develop becomes inevitable choice.
By the combination by multi-substituent pyrazole heterocycle group and pyrazoles oxime, be expected to the new compound obtaining having insecticidal activity.
Summary of the invention
The object of this invention is to provide, for various insect, there is excellent prevention effect, and efficiently, safety, an eco-friendly class containing the pyrazoles oxime compounds of multi-substituent pyrrazole structure, 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 and is preparing the purposes in sterilant.
The object of the invention reaches by following measures:
Pyrazoles oxime compounds containing multi-substituent pyrrazole structure of the present invention, is characterized in that the structure possessed as shown in formula I:
Wherein, on phenyl ring, the position of substitution represents with 2 ~ 4 or 2 ' ~ 4 ';
R
1(or R
2) be H, Cl, Br, F, I, CH
3, OCH
3or OCF
3in a kind of monosubstituted base of group, or be the disubstituted of above-mentioned any two kinds of groups composition;
R
1(or R
2) the position of substitution on phenyl ring can in 2 (2 ') position or 3 (3 ') position or 4 (4 ') position.
Such is containing the pyrazoles oxime compounds preparation method of multi-substituent pyrrazole structure, it is characterized in that the compound shown in formula I by general formula II and 1,3-dimethyl-5-aryloxy-pyrazoles-4-monobromomethane (chlorine) intermediate (III) under acid binding agent effect in aprotic polar solvent condensation obtain:
Wherein, on phenyl ring, the position of substitution represents with 2 ~ 4 or 2 ' ~ 4 ';
R
1(or R
2) be H, Cl, Br, F, I, CH
3, OCH
3or OCF
3in a kind of monosubstituted base of group, or be the disubstituted of above-mentioned any two kinds of groups composition;
R
1(or R
2) the position of substitution on phenyl ring can in 2 (2 ') position or 3 (3 ') position or 4 (4 ') position.
Acid binding agent is: pyridine, sodium bicarbonate, triethylamine, diisopropylethylamine (DIEA), 4-N, N-lutidine (DMAP), sodium carbonate, salt of wormwood and cesium carbonate; The consumption of acid binding agent is generally 1.2 ~ 15 times of compound molar weight shown in general formula II.
Wherein aprotic polar solvent is: DMF (DMF), N,N-dimethylacetamide (DMA), DMSO, Isosorbide-5-Nitrae-dioxane, acetonitrile and hexamethylphosphoramide (HMPA).
Wherein the molar weight of compound III is 0.95 ~ 1.6 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., method synthesis 2005 (15), 3307-3312.) obtains;
It is active that compound of Formula I has excellent control to insect, and thus compound of the present invention can be used as preparing sterilant, and then the plant such as protecting agriculture, gardening.Described insect has mythimna separata, carmine spider mite etc.Certainly, the harmful organism that compound of the present invention can be prevented and treated is not limited to the scope of above-mentioned citing.
When being used as the sterilant in the fields such as agricultural, gardening when the compound of the present invention represented by general formula I, can be used alone, or use in the mode of insect-killing composition, as with formula I for 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 represented by general formula I is used as the activeconstituents in sterilant, the content in described sterilant can be selected in the scope of 0.1% to 99.5%, and can determine suitable active component content according to dosage form and application process.Usually, containing the activeconstituents described in 5% to 50% (weight percent, lower same) in aqueous emulsion, preferably its content is 10% to 40%; Containing the activeconstituents of 5% to 50% in suspension agent, preferably its content is 5% to 40%.
For Utilization of pesticides of the present invention, the application method commonly used can be selected, as cauline leaf spraying, used for ponds, soil treatment and seed treatment etc.Such as, when adopting cauline leaf spraying, as activeconstituents the compound represented by general formula I can working concentration scope be aqueous emulsion, suspension agent, water dispersion granule, the missible oil of 1 to 1000 μ g/mL.
Pyrazoles oxime compounds containing multi-substituent pyrrazole structure disclosed by the invention has excellent 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 provided below has done more detailed description to it.These embodiments only are not used for limiting scope of the present invention or implementation principle for describing.
Embodiment 1:
Synthesis (X=Cl, the R of chemical compounds I a
1=H, R
2=4-Cl)
In reaction flask, add pyrazoles oxime intermediate II a 5mmol, 1,3-dimethyl-5-phenoxy group-pyrazoles-4-methyl chloride intermediate III 6mmol and 25mL acetonitrile, under stirring, drop into 9mmol salt of wormwood wherein, by the mixture reflux 12 hours of gained.Stop heating.Filter, by mother liquor concentrations to dry, silica gel mixed sample dress post separating-purifying obtains target compound I a.
1H NMR(400MHz,CDCl
3):δ7.61(s,1H,CH＝N),7.30-7.34(m,2H,ArH),7.09-7.20(m,3H,ArH),6.89(d,J＝8.0Hz,2H,Ar-H),6.83(d,J＝8.0Hz,2H,Ar-H),4.67(s,2H,CH
2),3.60(s,3H,N-CH
3),3.55(s,3H,N-CH
3),2.36(s,3H,CH
3),2.25(s,3H,CH
3).
Embodiment 2:
Synthesis (synthesis of reference compound Ia, wherein X=Cl, the R of compoundsⅰb
1=4-Cl, R
2=4-Cl)
In reaction flask, add pyrazoles oxime intermediate II b 4mmol, 13-dimethyl-5-phenoxy group-pyrazoles-4-methyl chloride intermediate III 4.4mmol and 15mL DMF, under stirring, drop into 5mmol cesium carbonate wherein, by the mixture reflux 12 hours of gained.Stop heating.Filter, by mother liquor concentrations to dry, chromatography column separating-purifying obtains target compound I b.
1H NMR(400MHz,CDCl
3):δ7.59(s,1H,CH＝N),7.27(d,J＝8.0Hz,2H,Ar-H),7.19(d,J＝8.0Hz,2H,Ar-H),6.82(d,J＝8.0Hz,4H,Ar-H),4.65(s,2H,CH
2),3.59(s,3H,N-CH
3),3.55(s,3H,N-CH
3),2.33(s,3H,CH
3),2.24(s,3H,CH
3).
Embodiment 3:
Synthesis (synthesis of reference compound Ia, wherein X=Br, the R of chemical compounds I c
1=3-F, R
2=4-Cl)
Pyrazoles oxime intermediate II c 3mmol, 1 is added in reaction flask, 3-dimethyl-5-phenoxy group-pyrazoles-4-monobromomethane intermediate III 4.4mmol and 25mL1,4-dioxane, 18mmol 4-N is dropped into wherein under stirring, N dimethylamine yl pyridines (DMAP), is heated to 80 DEG C of reactions 19 hours by the mixture of gained.Stop heating.Filter, filtrate be concentrated into dry, chromatography column separating-purifying obtains target compound I c.
1H NMR(400MHz,CDCl
3):δ7.60(s,1H,CH＝N),7.20(d,J＝8.0Hz,2H,Ar-H),6.98-7.02(m,2H,Ar-H),6.82-6.87(m,4H,Ar-H),4.67(s,2H,CH
2),3.60(s,3H,N-CH
3),3.56(s,3H,N-CH
3),2.35(s,3H,CH
3),2.26(s,3H,CH
3).
Embodiment 4:
Synthesis (synthesis of reference compound Ia, wherein X=Br, the R of chemical compounds I d
1=4-OCF
3, R
2=4-Cl)
Pyrazoles oxime intermediate II d 2mmol, 1 is added in reaction flask, 3-dimethyl-5-phenoxy group-pyrazoles-4-monobromomethane intermediate III 3mmol and 15mL N, N-N,N-DIMETHYLACETAMIDE, drop into 5mmol salt of wormwood wherein under stirring, the mixture of gained is slowly warming up to 80 DEG C of reactions 16 hours, after being chilled to room temperature, filter, collect filtrate, concentrating under reduced pressure obtains crude product, obtains final product Id through column chromatography.
1H NMR(400MHz,CDCl
3):δ7.61(s,1H,CH＝N),7.17-7.21(m,4H,ArH),6.90(d,J＝12.0Hz,2H,Ar-H),6.83(d,J＝8.0Hz,2H,Ar-H),4.64(s,2H,CH
2),3.61(s,3H,N-CH
3),3.56(s,3H,N-CH
3),2.34(s,3H,CH
3),2.24(s,3H,CH
3).
Embodiment 5:
Synthesis (synthesis of reference compound Ia, wherein X=Br, the R of chemical compounds I e
1=2-Cl, R
2=2,4-Cl
2)
Pyrazoles oxime intermediate II e 4mmol, 1 is added in reaction flask, 3-dimethyl-5-phenoxy group-pyrazoles-4-monobromomethane intermediate III 5.6mmol and 20mL DMSO, drop into 6mmol salt of wormwood wherein under stirring, the mixture of gained is heated to 80 DEG C of reactions 18 hours, stops heating.Filter, by mother liquor concentrations to dry, silica gel mixed sample dress post separating-purifying obtains target compound I e.
1H NMR(400MHz,CDCl
3):δ7.56(s,1H,CH＝N),7.46(d,J＝8.0Hz,1H,Ar-H),7.40(s,1H,ArH),7.00-7.18(m,3H,Ar-H),6.66-6.71(m,2H,Ar-H),4.64(s,2H,CH
2),3.63(s,3H,N-CH
3),3.58(s,3H,N-CH
3),2.34(s,3H,CH
3),2.23(s,3H,CH
3).
Embodiment 6:
Synthesis (synthesis of reference compound Ia, wherein X=Br, the R of chemical compounds I f
1=2-F, R
2=2,4-Cl
2)
Pyrazoles oxime intermediate II f 6mmol, 1 is added in reaction flask, 3-dimethyl-5-phenoxy group-pyrazoles-4-monobromomethane intermediate III 8mmol and 30mL Isosorbide-5-Nitrae-dioxane, drops into 18mmol pyridine under stirring wherein, the mixture of gained is heated to 85 DEG C of reactions 13 hours, stops heating.Filter, by mother liquor concentrations to dry, silica gel mixed sample dress post separating-purifying obtains target compound I f.
1H NMR(400MHz,CDCl
3):δ7.57(s,1H,CH＝N),7.40(s,1H,ArH),7.16-7.20(m,1H,Ar-H),6.98-7.09(m,3H,Ar-H),6.68-6.77(m,2H,Ar-H),4.62(s,2H,CH
2),3.65(s,3H,N-CH
3),3.57(s,3H,N-CH
3),2.32(s,3H,CH
3),2.23(s,3H,CH
3).
Embodiment 7:
Sample screens the insecticidal activity of carmine spider mite
Adopt the spray method that international resistance Action Committee (IRAC) proposes.Examination target is supplied to be carmine spider mite.The Broad Bean Leaves being about to be connected to carmine spider mite is sprayed process under Potter spray tower, and after process, carmine spider mite is placed in 24 ~ 27 DEG C and observes indoor cultivation, 48h " Invest, Then Investigate " result.Touch polypide with writing brush, be reactionlessly considered as dead worm.Initial trial concentration 500 μ g/mL (liquid of other concentration can be diluted by the liquid of 500 μ g/mL and obtain).
Embodiment 8:
Sample screens the insecticidal activity of mythimna separata
Adopt the leaf dipping method that international resistance Action Committee (IRAC) proposes.Supply examination target to be mythimna separata, naturally dry in the shade after fully infiltrating in the liquid prepared by appropriate leaf of Semen Maydis, put into the culture dish being lined with filter paper, connect mythimna separata 3 larva in mid-term in age 10/ware, be placed in 24-27 DEG C of observation indoor cultivation, 2d " Invest, Then Investigate " result.Touch polypide with writing brush, be reactionlessly considered as dead worm.Initial trial concentration 500 μ g/mL (liquid of other concentration can be diluted by the liquid of 500 μ g/mL and obtain).
The insecticidal activity data (Mortality, %) of table 1.Ia-If
Insecticidal activity test result shows, and partial target thing shows carmine spider mite and good kills activity, and when test concentrations is 500 μ g/mL, wherein the prevention effect of compoundsⅰb to carmine spider mite reaches 75%; When test concentrations is 500 μ g/mL, wherein chemical compounds I f presents certain restraining effect to mythimna separata.Above data show, introduce in pyrazoles oxime modular construction and have multi-substituent pyrazoles active fragments, some target compound of gained demonstrates inhibition to carmine spider mite, mythimna separata, and part of compounds can be used as agricultural chemicals guide and does research deep further.
Claims (7)
1., containing a pyrazoles oxime compounds for multi-substituent pyrrazole structure, it is characterized in that the structure possessed as shown in formula I:
Wherein, on phenyl ring, the position of substitution represents with 2 ~ 4;
R is H, Cl, Br, F, I, CH
3, OCH
3or OCF
3in a kind of monosubstituted base of group, or be the disubstituted of above-mentioned any two kinds of groups composition;
R the position of substitution on phenyl ring can two or three-digit or 4.
2. the preparation method containing the pyrazoles oxime compounds of multi-substituent pyrrazole structure, it is characterized in that: the compound shown in formula I by general formula II and 1,3-dimethyl-5-aryloxy-pyrazoles-4-monobromomethane (chlorine) intermediate (III) under acid binding agent effect in aprotic polar solvent condensation obtain:
Wherein, on phenyl ring, the position of substitution represents with 2 ~ 4 or 2 ' ~ 4 ';
R
1, R
2for H, Cl, Br, F, I, CH
3, OCH
3or OCF
3in a kind of monosubstituted base of group, or be the disubstituted of above-mentioned any two kinds of groups composition;
R
1, R
2the position of substitution on phenyl ring is in 2 (2 ') position or 3 (3 ') position or 4 (4 ') position.
3. preparation method according to claim 2, is characterized in that, wherein acid binding agent is pyridine, sodium bicarbonate, triethylamine, diisopropylethylamine (DIEA), 4-N, N-lutidine (DMAP), sodium carbonate, the one in salt of wormwood or cesium carbonate; 1.2 ~ 15 times that the consumption of acid binding agent is compound molar weight shown in general formula II.
4. preparation method according to claim 2, it is characterized in that, wherein aprotic polar solvent is: 1,4-dioxane, DMF (DMF), acetonitrile, DMSO, the one in N,N-dimethylacetamide (DMA) or hexamethylphosphoramide (HMPA).
5. synthetic method according to claim 2, is characterized in that, wherein the molar weight of compound III is 0.95 ~ 1.6 times of general formula II compound molar weight.
6. compound according to claim 1 is preparing the purposes in sterilant, it is characterized in that: this compound is used alone; Or use in the mode of insect-killing composition, namely with formula I for activeconstituents, add that the conventional inert ingredient in this area is processed into aqueous emulsion, suspension agent, water dispersion granule, missible oil etc.
7. pyrazoles oxime compounds according to claim 6 is preparing the purposes in sterilant, it is characterized in that: when the compound of the present invention represented by general formula I is used as the activeconstituents in sterilant, the content in described sterilant can be selected in the scope of 0.1% to 99.5%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410820503.3A CN104557710B (en) | 2014-12-25 | 2014-12-25 | The preparation and application of the pyrazoles oxime compound of the pyrrazole structure containing multi-substituent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410820503.3A CN104557710B (en) | 2014-12-25 | 2014-12-25 | The preparation and application of the pyrazoles oxime compound of the pyrrazole structure containing multi-substituent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104557710A true CN104557710A (en) | 2015-04-29 |
| CN104557710B CN104557710B (en) | 2017-12-15 |
Family
ID=53074886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410820503.3A Active CN104557710B (en) | 2014-12-25 | 2014-12-25 | The preparation and application of the pyrazoles oxime compound of the pyrrazole structure containing multi-substituent |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104557710B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106243039A (en) * | 2016-07-29 | 2016-12-21 | 南通大学 | Preparation method and application containing the pyrazoles oxime compound of 1 methyl 3 ethyl 4 chlorine 5 formoxyl pyrrazole 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 |
| CN106432216A (en) * | 2016-08-01 | 2017-02-22 | 南通大学 | Preparation method and application of pyrazol amide compound containing 5-aryl isoxazole structure |
| 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 |
| CN110305115A (en) * | 2019-08-19 | 2019-10-08 | 南通大学 | The preparation and application of pyrazoles 9 oxime derivate of the one kind containing 1- (6- chloropyrazine -2- base) -3- methoxyl group pyrazoles unit |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0361827A1 (en) * | 1988-09-29 | 1990-04-04 | Sumitomo Chemical Company, Limited | Pyrazole compounds, method for production thereof, use thereof and intermediates for production thereof |
| EP0391685A1 (en) * | 1989-04-07 | 1990-10-10 | Ube Industries, Ltd. | Pyrazoleoxime derivatives and insecticides, acaricides and fungicides |
| WO2006000311A1 (en) * | 2004-06-26 | 2006-01-05 | Merial Ltd. | 1-arylpyrazole derivatives pesticidal agents |
| CN1844103A (en) * | 2006-03-22 | 2006-10-11 | 南开大学 | Pyrazol oxime ether derivatives and preparation process and use thereof |
| CN104193683A (en) * | 2014-07-25 | 2014-12-10 | 南通大学 | Pyrazole oxime derivative containing dichloropropene as well as preparation method and application method of derivative |
-
2014
- 2014-12-25 CN CN201410820503.3A patent/CN104557710B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0361827A1 (en) * | 1988-09-29 | 1990-04-04 | Sumitomo Chemical Company, Limited | Pyrazole compounds, method for production thereof, use thereof and intermediates for production thereof |
| EP0391685A1 (en) * | 1989-04-07 | 1990-10-10 | Ube Industries, Ltd. | Pyrazoleoxime derivatives and insecticides, acaricides and fungicides |
| WO2006000311A1 (en) * | 2004-06-26 | 2006-01-05 | Merial Ltd. | 1-arylpyrazole derivatives pesticidal agents |
| CN1844103A (en) * | 2006-03-22 | 2006-10-11 | 南开大学 | Pyrazol oxime ether derivatives and preparation process and use thereof |
| CN104193683A (en) * | 2014-07-25 | 2014-12-10 | 南通大学 | Pyrazole oxime derivative containing dichloropropene as well as preparation method and application method of derivative |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106432081B (en) * | 2016-07-26 | 2020-03-31 | 南通大学 | Preparation method and application of pyrazole oxime ether compound containing 4-chloro-3-ethyl-1-methylpyrazole structure |
| CN106243039A (en) * | 2016-07-29 | 2016-12-21 | 南通大学 | Preparation method and application containing the pyrazoles oxime compound of 1 methyl 3 ethyl 4 chlorine 5 formoxyl pyrrazole structure |
| CN106243039B (en) * | 2016-07-29 | 2020-03-31 | 南通大学 | Preparation method and application of pyrazole oxime compound containing 1-methyl-3-ethyl-4-chloro-5-formylpyrazole structure |
| CN106432216A (en) * | 2016-08-01 | 2017-02-22 | 南通大学 | Preparation method and application of pyrazol amide compound containing 5-aryl isoxazole structure |
| CN106432216B (en) * | 2016-08-01 | 2019-09-20 | 南通大学 | The preparation method and application of the pyrazol acid amide compounds of the isoxazole structure of aryl containing 5- |
| 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 |
| CN106946782B (en) * | 2017-02-08 | 2019-09-24 | 南通大学 | Pyrazole Oxime Esters of the biphenyl structures containing pyrazoles and its preparation method and application |
| CN110305115A (en) * | 2019-08-19 | 2019-10-08 | 南通大学 | The preparation and application of pyrazoles 9 oxime derivate of the one kind containing 1- (6- chloropyrazine -2- base) -3- methoxyl group pyrazoles unit |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104557710B (en) | 2017-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102445236B1 (en) | m-diamide-based compound and its preparation and application | |
| CN104557710A (en) | Preparation and application of pyrazole oxime compound containing multi-substituent pyrazole structure | |
| CN104892591B (en) | The preparation method and application of the pyrazoles oxime compound of the oxadiazole heterocycle structure containing 3 aryl 1,2,4 | |
| CN101935291B (en) | Cyano phthalic diamide compounds, preparation method thereof and use thereof as agricultural chemical pesticide | |
| CN104193727A (en) | Preparation and application of pyrazole oxime ether compound containing trifluoro methyl pyridine | |
| EA020755B1 (en) | Insecticidal compounds | |
| CN104151308B (en) | Preparation and application containing 1,2,3 thiadiazoles Pyrazole Oxime Esters | |
| CN108069984B (en) | Substituted five-membered heterocyclic compound containing pyrimido ring and preparation method and application thereof | |
| CN104119316B (en) | Pyridine phenyl ether compound and Synthesis and applications thereof | |
| CN106432081A (en) | Preparation method and application of pyrazole oxime ether compound containing 4-Cl-3-ethyl-1-methylpyrazole structure | |
| CN109879867B (en) | Preparation and application of pyrazole oxime ether compound containing 5-aryl oxazole structure | |
| CN113454063A (en) | 3-substituted phenylamidine compounds, preparation method and application thereof | |
| CN105037342A (en) | Pyrazole ether compound with herbicidal activity and application thereof | |
| CN104151309A (en) | Preparation and application of compound containing 1,3,4-thiadiazole parazole oxime ether | |
| CN105693710A (en) | Preparation and application of pyrazole oxime ether compound with 5-(4-fluorophenyl) isoxazole structure | |
| US8933234B2 (en) | O-amino benzonitrile compounds, method for preparing same and uses thereof | |
| EA004574B1 (en) | Oxime o-ether compounds and fungicides for agricultural and horticultural use | |
| CN104193683A (en) | Pyrazole oxime derivative containing dichloropropene as well as preparation method and application method of derivative | |
| CN105884744A (en) | Preparation and application of pyrazole oxime ester compound containing 2-chloropyridine structure | |
| CN113549053B (en) | Pyrazoloquine (azolyl) ether compound and application thereof | |
| CN109232534B (en) | Heterocyclic diarylamine-containing pyrazole formamide compound and preparation method and application thereof | |
| CN103951612A (en) | Oxime ether acetate compound and preparation method and application thereof | |
| CN104725348B (en) | Anthraniloyl alkyl iso (thio) urea compound and synthesis method and application thereof | |
| CN106349223B (en) | The preparation method and application of the pyrazoles oxime ether compound of the sulfide based structural containing pyrimidine | |
| EA019857B1 (en) | Insecticidal compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20190711 Address after: No. 9, Nantong City, Jiangsu, Jiangsu Patentee after: Center for technology transfer, Nantong University Address before: No. 9, Nantong City, Jiangsu, Jiangsu Patentee before: Nantong University |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20191016 Address after: 226000, Gangzha District, Jiangsu City, Gangzha province Nantong port industrial and Trade Park Patentee after: Nantong new silk monofilament Polytron Technologies Inc Address before: 226019 Jiangsu city of Nantong province sik Road No. 9 Patentee before: Center for technology transfer, Nantong University |