CN110845487B - 3- (triazole biphenyl methoxyl) pyrazole amide compound containing isoxazole structure and preparation method and application thereof - Google Patents
3- (triazole biphenyl methoxyl) pyrazole amide compound containing isoxazole structure and preparation method and application thereof Download PDFInfo
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- CN110845487B CN110845487B CN201911130818.4A CN201911130818A CN110845487B CN 110845487 B CN110845487 B CN 110845487B CN 201911130818 A CN201911130818 A CN 201911130818A CN 110845487 B CN110845487 B CN 110845487B
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- C07—ORGANIC CHEMISTRY
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
- A01N43/80—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 1,2
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Abstract
The invention relates to a 3- (triazole biphenyl methoxyl) pyrazole amide compound containing an isoxazole structure, a preparation method and application thereof (I), and a preparation method and application thereof. Obtained by condensing substituted pyrazolecarbonyl chloride (II) and isoxazolyl methylamine (III). The 3- (triazole biphenyl methoxyl) pyrazole amide compound containing the isoxazole structure has an effective control effect on harmful insects, and can be used for preparing insecticides in the fields of agriculture, horticulture and the like.
Description
Technical Field
The invention relates to the field of chemical pesticides, in particular to a 3- (triazole biphenyl methoxyl) pyrazole amide compound containing an isoxazole structure, and a preparation method and application thereof.
Background
The prevention and control of pests have been the core field of pesticide science research, and the wide use of pesticides enables most pests to be effectively treated. However, with the continuous expansion of the application scale of the pesticide, the problem of the drug resistance of the traditional pesticide varieties becomes more and more prominent, and the continuous research and development of new pesticides become a necessary choice in addition to the continuous emergence of new plant diseases and insect pests.
Pyrazole rings are used as important heterocyclic rings and have wide application in the field of pesticides, pyrazole compounds have excellent insecticidal and acaricidal activities, and the pyrazole heterocyclic rings are widely introduced into pesticide compound molecules, such as pyrazole insecticide tolfenpyrad and pyrazole acaricide fenpyroximate.
Isoxazole rings play an important role as important heterocycles in the field of agricultural chemicals, and in recent years, isoxazole compounds have been reported to exhibit excellent insecticidal activity.
Therefore, in order to further search compounds with excellent biological activity from pyrazole derivatives and reasonably and organically combine a pyrazole skeleton and an isoxazole unit, the invention discloses a 3- (triazole biphenyl methoxyl) pyrazole amide compound containing an isoxazole structure, which has agricultural insecticidal application value.
Disclosure of Invention
The invention aims to provide a 3- (triazole biphenyl methoxyl) pyrazole amide compound containing an isoxazole structure, which has excellent control effect on various pests, is efficient, safe and environment-friendly, and meets the requirement of crop protection on high-efficiency pesticides.
It is a further object of the present invention to provide the use of the above compounds in the preparation of insecticides.
Another object of the present invention is to provide a process for the preparation of the above compounds.
In order to solve the technical problems, the invention provides a 3- (triazole biphenyl methoxyl) pyrazole amide compound containing an isoxazole structure, which has a structure shown in a general formula I,
preferably, the 3- (triazole biphenyl methoxy) pyrazole amide compound containing the isoxazole structure has the following structure:
the second aspect of the present invention provides a preparation method of the above 3- (triazole biphenyl methoxy) pyrazole amide compound containing an isoxazole structure, which comprises the following steps:
dissolving a compound III in an organic solvent, adding an acid-binding agent, adding an intermediate II, finally reacting for a period of time, carrying out suction filtration on a reaction solution, carrying out reduced pressure concentration on a mother solution, separating and purifying obtained residues to obtain a target compound,
preferably, the acid scavenger is selected from triethylamine, pyridine, 4-Dimethylaminopyridine (DMAP) and sodium bicarbonate, and the solvent is selected from chloroform, dichloromethane, N-Dimethylformamide (DMF), N-Dimethylacetamide (DMA) and acetonitrile.
Preferably, the preparation method of the 3- (triazole biphenyl methoxyl) pyrazole amide compound containing the isoxazole structure comprises the following steps:
wherein, the intermediate III of the 5-aryl isoxazole-3-methylamine can be synthesized by the method of the reference literature (Chemical Reagents 2004,26, 99-100); substituted pyrazolylchloride intermediates ii were synthesized according to the methods described in the literature (j.agric.food chem.2013,61, 8730-8736).
The compound of the general formula I has excellent control activity on insects, so that the compound can be used for preparing pesticides to protect plants in agriculture, horticulture and the like. Of course, the pests which the compounds of the invention can control are not limited to the above exemplified ranges.
When the compound of the invention represented by the general formula I is used as an insecticide in the fields of agriculture, horticulture and the like, the compound can be used alone or in the form of an insecticidal composition, for example, the compound is prepared into an aqueous emulsion, a suspending agent, a water dispersible granule, an emulsion and the like by taking the formula I as an active ingredient and adding pesticide auxiliaries commonly used in the field.
Commonly used pesticide adjuvants include liquid carriers such as water; organic solvents such as toluene, xylene, cyclohexanol, methanol, butanol, ethylene glycol, acetone, dimethylformamide, acetic acid, dimethyl sulfoxide, animal and vegetable oils and fatty acids; common surfactants such as emulsifiers and dispersants, including anionic surfactants, cationic surfactants, nonionic surfactants, and amphoteric surfactants; other adjuvants, such as wetting agents, thickeners, and the like.
When the compound of the present invention represented by the general formula I is used as an active ingredient in an insecticide, the content in the insecticide is selected in the range of 0.1% to 99.5%, and an appropriate content of the active ingredient may be determined according to the formulation form and the application method. In general, the aqueous emulsion contains 5% to 50% (by weight, the same applies hereinafter) of the active ingredient, preferably 10% to 40%; the suspension concentrate contains 5% to 50% of active ingredient, preferably 5% to 40%.
For the use of the insecticide of the present invention, a commonly used application method such as stem and leaf spraying, water surface application, soil treatment, seed treatment, and the like can be selected. For example, when spray application from stems and leaves is employed, the compounds of the formula I as active ingredients can be used in the concentration range from 1 to 1000. Mu.g/mL in water emulsions, suspensions, water-dispersible granules, emulsifiable concentrates, preferably in concentrations from 1 to 500. Mu.g/mL.
The 3- (triazole biphenyl methoxyl) pyrazole amide compound containing the isoxazole structure disclosed by the invention has an excellent control effect on harmful insects, and therefore, the compound can be used for preparing insecticides used in the fields of agriculture, horticulture and the like.
Detailed Description
The above-described scheme is further illustrated below with reference to specific examples. It should be understood that these examples are for illustrative purposes and are not intended to limit the scope of the present invention. The conditions used in the examples may be further adjusted according to the conditions of the particular manufacturer, and the conditions not specified are generally the conditions in routine experiments.
Example 1:
5mmol of compound IIIa are dissolved in 30mL of chloroform, followed by addition of 20mmol of triethylamine and subsequent addition of 7mmol of intermediate II under ice-bath conditions. After the addition was completed, the ice-bath reaction was continued for 10 hours. Stopping the reaction, carrying out reduced pressure rotary evaporation on the reaction liquid until the reaction liquid is dried, and carrying out column chromatography separation on the obtained crude product to obtain a target Ia; 1 H NMR(400MHz,CDCl 3 ):δ8.47～8.49(m,1H,Py-H),8.08(d,J＝8.8Hz,2H,Ar-H),7.88～7.91(m,1H,Py-H),7.81(s,2H,Triazole-H),7.70～7.74(m,2H,Ar-H),7.56(d,J＝8.4Hz,2H,Ar-H),7.37～7.40(m,1H,Py-H),7.13～7.17(m,2H,Ar-H),6.43(s,1H,Isoxazole-H),6.28(s,1H,Pyrazole-H),5.35(s,2H,CH 2 ),4.60(d,J＝6.0Hz,2H,CH 2 ).
example 2:
4mmol of compound IIIb are dissolved in 20mL of dichloromethane, followed by addition of 30mmol of pyridine and subsequent addition of 4mmol of intermediate II thereto under ice-bath conditions. After the addition, the reaction was heated under reflux for 18 hours. Stopping the reaction, carrying out reduced pressure rotary evaporation on the reaction liquid until the reaction liquid is dried, and carrying out column chromatography separation on the obtained crude product to obtain a target object Ib; 1 H NMR(400MHz,CDCl 3 ):δ8.48(d,J＝4.4Hz,1H,Py-H),8.09(d,J＝8.4Hz,2H,Ar-H),7.89(d,J＝8.0Hz,1H,Py-H),7.82(s,2H,Triazole-H),7.67(d,J＝8.4Hz,2H,Ar-H),7.56(d,J＝8.4Hz,2H,Ar-H),7.43(d,J＝8.4Hz,2H,Ar-H),7.37～7.40(m,1H,Py-H),6.94(s,1H,NH),6.48(s,1H,Isoxazole-H),6.30(s,1H,Pyrazole-H),5.35(s,2H,CH 2 ),4.61(d,J＝6.0Hz,2H,CH 2 ).
example 3:
5mmol of compound IIIc are dissolved in 25mL of DMF, 30mmol of 4-Dimethylaminopyridine (DMAP) are subsequently added, and 9mmol of intermediate II are subsequently added thereto under ice-bath conditions. After the addition, the temperature is raised to 90 ℃ for reaction for 22 hours. Stopping the reaction, carrying out rotary evaporation on the reaction liquid under reduced pressure until the reaction liquid is dried, and carrying out column chromatography separation on the obtained crude product to obtain the target compound Ic. 1 H NMR(400MHz,CDCl 3 ):δ8.47～8.49(m,1H,Py-H),8.09(d,J＝8.4Hz,2H,Ar-H),7.88～7.91(m,1H,Py-H),7.82(s,2H,Triazole-H),7.55～7.59(m,6H,Ar-H),7.37～7.40(m,1H,Py-H),6.93(s,1H,NH),6.49(s,1H,Isoxazole-H),6.29(s,1H,Pyrazole-H),5.35(s,2H,CH 2 ),4.60(d,J＝6.0Hz,2H,CH 2 ).
Example 4:
6mmol of compound IIId was dissolved in 35mL of DMA, followed by addition of 30mmol of triethylamine, and then 9mmol of intermediate II was added thereto under ice-bath conditions. After the addition, the mixture is heated to 80 ℃ for reaction for 20 hours. Stopping the reaction, carrying out rotary evaporation on the reaction liquid under reduced pressure until the reaction liquid is dried, and carrying out column chromatography separation on the obtained crude product to obtain the target object Id. 1 H NMR(400MHz,CDCl 3 ):δ8.46～8.48(m,1H,Py-H),8.07(d,J＝8.8Hz,2H,Ar-H),7.87～7.89(m,1H,Py-H),7.80(s,2H,Triazole-H),7.60(d,J＝8.4Hz,2H,Ar-H),7.54(d,J＝8.4Hz,2H,Ar-H),7.35～7.38(m,1H,Py-H),7.23(d,J＝8.0Hz,3H,Ar-H and NH),6.42(s,1H,Isoxazole-H),6.32(s,1H,Pyrazole-H),5.33(s,2H,CH 2 ),4.57(d,J＝5.6Hz,2H,CH 2 ),2.37(s,3H,Ar-CH 3 ).
Example 5:
3mmol of compound IIIe were dissolved in 30mL of acetonitrile, followed by addition of 25mmol of sodium bicarbonate, and then 3mmol of intermediate II was added thereto under ice-bath conditions.After the addition, the temperature is raised to 65 ℃ for reaction for 18 hours. Stopping the reaction, carrying out rotary evaporation on the reaction liquid under reduced pressure until the reaction liquid is dried, and carrying out column chromatography separation on the obtained crude product to obtain a target substance Ie. 1 H NMR(400MHz,CDCl 3 ):δ8.48(d,J＝4.8Hz,1H,Py-H),8.08(d,J＝8.4Hz,2H,Ar-H),7.89(d,J＝8.0Hz,1H,Py-H),7.81(s,2H,Triazole-H),7.66(d,J＝8.4Hz,2H,Ar-H),7.56(d,J＝8.4Hz,2H,Ar-H),7.36～7.39(m,1H,Py-H),7.02(s,1H,NH),6.95(d,J＝8.8Hz,2H,Ar-H),6.35(s,1H,Isoxazole-H),6.31(s,1H,Pyrazole-H),5.35(s,2H,CH 2 ),4.59(d,J＝5.2Hz,2H,CH 2 ),3.85(s,3H,Ar-OCH 3 ).
Example 6:
6mmol of the compound IIIf are dissolved in 30mL of dichloromethane, 25mmol of triethylamine are subsequently added, and 7mmol of the intermediate II are subsequently added thereto under ice-bath conditions. After the addition, the ice field stirring was continued for 12 hours. Stopping the reaction, carrying out rotary evaporation on the reaction liquid under reduced pressure until the reaction liquid is dried, and carrying out column chromatography separation on the obtained crude product to obtain the target compound If. 1 H NMR(400MHz,CDCl 3 ):δ8.49(d,J＝3.6Hz,1H,Py-H),8.15(d,J＝8.4Hz,1H,Ar-H),7.90(d,J＝8.8Hz,1H,Py-H),7.68～7.81(s,6H,Ar-H and Triazole-H),7.38～7.58(m,5H,Py-H and Ar-H),7.12(s,1H,NH),6.49(s,1H,Isoxazole-H),6.36(s,1H,Pyrazole-H),5.42(s,2H,CH 2 ),4.62(d,J＝5.2Hz,2H,CH 2 ).
Example 7:
insecticidal activity screening of samples against armyworm
Leaf dipping method proposed by International Resistance Action Committee (IRAC) was used: the target for testing is armyworm, namely, a proper amount of corn leaves are fully soaked in prepared liquid medicine and then naturally dried in the shade, the corn leaves are placed into a culture dish filled with filter paper, 10 heads/dish of armyworm larvae in the 3-instar middle stage are connected, the corn leaves are placed into an observation room for culture at 24-27 ℃, and the result is investigated after 2 days. If the body of the insect is touched by a writing brush, the dead insect is determined to be no response. The test concentration was 500. Mu.g/mL (other concentrations of drug solution could be diluted with 500. Mu.g/mL).
Example 8:
screening of insecticidal Activity of samples against aphids
The spray method proposed by the International Resistance Action Committee (IRAC) was used: the test target is aphids, namely broad bean leaves connected with the aphids are sprayed under a Potter spray tower, the treated aphids are cultured in an observation room at the temperature of 20-22 ℃, and the result is investigated after 48 hours. If the body of the insect is touched by a writing brush, the dead insect is determined to be no response. The test concentration was 500. Mu.g/mL (the drug solution of other concentration can be diluted with 500. Mu.g/mL).
The insecticidal activity test data show that at a concentration of 500. Mu.g/mL, the insecticidal activity of the compounds Ia to ie against armyworm is 100%,100%,100%,100% and 100%, respectively (Table 1); in addition, the insecticidal effect of the compound if on aphids reaches 100% at the concentration of 500 mu g/mL.
Preliminary pesticidal Activity data for Ia-If
"-" means not determined
The experimental data show that the novel compound obtained by combining the substituted pyrazole ring and the isoxazole active unit shows excellent insecticidal activity, and important experimental data are provided for the continuous synthesis and biological activity research of novel pyrazole derivatives in the future.
The foregoing shows and describes the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited by the foregoing examples, which are provided to illustrate the principles of the invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention, which is also intended to be covered by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (4)
1. A3- (triazole biphenyl methoxyl) pyrazole amide compound I containing an isoxazole structure is characterized by having the following structure:
2. the preparation method of the 3- (triazole biphenyl methoxy) pyrazole amide compound I containing the isoxazole structure as claimed in claim 1, characterized in that the method is as follows:
3. the use of the isoxazole structure-containing 3- (triazole biphenylylmethoxy) pyrazole amide compound I according to claim 1 in the preparation of aphicide, characterized in that: the compound is used alone; or in the form of insecticidal compositions, namely, the compound I in claim 1 is used as an active ingredient, and is added with pesticide auxiliary agents commonly used in the field to be processed into aqueous emulsions, suspending agents, water dispersible granules and emulsifiable concentrates.
4. The use of the isoxazole structure-containing 3- (triazole biphenylylmethoxy) pyrazole amide compound I according to claim 3 in the preparation of aphicide, characterized in that: when compound I according to claim 1 is used as active ingredient of an aphicidal drug, the content in the aphicidal drug is selected in the range of 0.1% to 99.5%.
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| CN111253384B (en) * | 2020-04-01 | 2023-04-07 | 南通大学 | Preparation and application of 3-isoxazole methoxy pyrazole-5-amide containing substituted phenyl isoxazole unit |
| CN111560015B (en) * | 2020-05-27 | 2023-01-06 | 南通大学 | Preparation and application of 1,2,3-triazole benzyloxy pyrazole derivative containing 1,2,4-oxadiazole unit |
| CN111471042B (en) * | 2020-05-27 | 2023-01-06 | 南通大学 | Pyrazole compound containing substituted phenyl oxadiazole structure and preparation method and application thereof |
| CN111560010B (en) * | 2020-06-04 | 2022-11-01 | 南通大学 | Preparation and application of pyrazole oxime derivative containing triazole aryl methoxy pyrazole unit |
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| 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 |
| CN109553605A (en) * | 2018-12-05 | 2019-04-02 | 南通大学 | Pyrazol acid amide compounds of the biphenyl structures containing tetrazole and its preparation method and application |
| CN109678846A (en) * | 2018-12-13 | 2019-04-26 | 南通大学 | Pyrazol acid amide compounds of the triazole structure containing 1,2,3- and its preparation method and application |
| CN110407828A (en) * | 2019-08-19 | 2019-11-05 | 南通大学 | A kind of pyrazoles -5- amide derivatives of the structure containing oxazole and its preparation method and application |
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| 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 |
| CN109553605A (en) * | 2018-12-05 | 2019-04-02 | 南通大学 | Pyrazol acid amide compounds of the biphenyl structures containing tetrazole and its preparation method and application |
| CN109678846A (en) * | 2018-12-13 | 2019-04-26 | 南通大学 | Pyrazol acid amide compounds of the triazole structure containing 1,2,3- and its preparation method and application |
| CN110407828A (en) * | 2019-08-19 | 2019-11-05 | 南通大学 | A kind of pyrazoles -5- amide derivatives of the structure containing oxazole and its preparation method and application |
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