CN107163008A - The oxoethanol ramification of carboxylic esters of 2 { [(3 heterocyclic radical) acryloyl group] phenyl } amino 2 and its application - Google Patents

The oxoethanol ramification of carboxylic esters of 2 { [(3 heterocyclic radical) acryloyl group] phenyl } amino 2 and its application Download PDF

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CN107163008A
CN107163008A CN201710486195.9A CN201710486195A CN107163008A CN 107163008 A CN107163008 A CN 107163008A CN 201710486195 A CN201710486195 A CN 201710486195A CN 107163008 A CN107163008 A CN 107163008A
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compound
solution
added
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antioxidant
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CN107163008B (en
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唐孝荣
刘辉
高扬
严映坤
杨建�
李唯
李唯一
曾义
张燕
陈绍玲
吴敏
陈宇
周贵华
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Jiangsu Guojiao New Materials Co ltd
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Xihua University
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Abstract

The present invention relates to amides compound and its preparation method and application, and in particular to the oxoethanol ramification of carboxylic esters of 2 { [(3 heterocyclic radical) acryloyl group] phenyl } amino 2 and its application.Present invention solves the technical problem that being to provide a kind of amides compound that can be used as antioxidant and agricultural insecticide.The structural formula of the compound is as shown in formula I.The present invention splices principle using bio-active group, heterocyclic compound is introduced into amide compound, some novel structures, the reactive compound of superior activity or active lead compound are found that, so as to establish preferable basis for the initiative of novel antioxidant and insecticide.

Description

2- { [(3- heterocyclic radicals) acryloyl group] phenyl } amino -2- oxoethanol carboxylic acid esters Derivative and its application
Technical field
The present invention relates to amides compound and its preparation method and application, and in particular to 2- { [(3- heterocyclic radicals) acryloyls Base] phenyl } amino -2- oxoethanols ramification of carboxylic esters and its application.
Background technology
Antioxidant effectively can delay or suppress many materials, particularly biological big point of sugar, fat, protein, nucleic acid etc. The oxidation deterioration of son, quite varied application is suffered from many fields：(1) in terms of food processing, antioxidant can suppress Oxidation of Fat and Oils, prevents it from becoming sour, frequently as food oxydating resistance additive；(2) in life science and medical domain, antioxidant energy Interior free yl is removed, slows down the formation of peroxidation state, various diseases caused by prevention and treatment free radical improve machine Body immunocompetence, so as to protect health；(3) in chemical industrial field, antioxidant adds as the stability of chemical products Plus agent, the antioxygenic property of product is improved, so as to extend its service life.Because antioxidant is in industrial and agricultural production and daily life Irreplaceable effect is all played in work, therefore, the research and development of the efficient, antioxidant of economy, low toxicity have very Important meaning.
On the other hand, long-term a large amount of use of agricultural chemicals particularly insecticide not only pollutes environment, destroys the ecological balance, It also results in serious " 3R " (residual, resistance and pest resurgence) and " three cause " (carcinogenic, teratogenesis shape and mutagenesis) problem.This A little problems cause the mankind and widely paid close attention to, how to efficiently solve these problems be facing mankind it is one long-term and it is arduous Task.So, huge challenge is faced with agricultural chemicals, and in the case that the mankind be unable to do without agricultural chemicals, finds high to harmful organism Effect, and drop production solution thing safe, degradable in the environment to non-target organism to human health and ecological environment security " environment with Humorous agricultural chemicals " or " environment friendly agricultural " focus into pesticide research and forward position.
Amides compound has extensive bioactivity, including sterilization, anti-oxidant, plant growth regulating etc..Therefore, exist In the past few decades, it is had made extensive and intensive studies, it was found that many new and effective compounds, but also constantly Have structure novelty, mode of action uniqueness, excellent performance, it is efficient to harmful organism, to non-target organism safety, in the environment easily drop Solve and catabolite is reported human health and the kind of ecological environment security.
Up to the present, it yet there are no the report that amides compound is used as antioxidant and agricultural insecticide.
The content of the invention
Present invention solves the technical problem that being to provide a kind of amide-type that can be used as antioxidant and agricultural insecticide Compound.
2- { [(3- heterocyclic radicals) acryloyl group] phenyl } amino -2- oxoethanol ramification of carboxylic esters of the present invention, its Structural formula is as shown in formula I：
Wherein, R1ForR2For C1-C4 Alkyl；R3For hydrogen or halogen；R4For hydrogen or halogen；X is O or S.
It is preferred that, R1For
It is furthermore preferred that R2For methyl.
Preferred structure formula is as shown in formula I -1 or formula I -2：
The present invention also provides purposes of the compounds of this invention in antioxidant is prepared.
The compound of the present invention, with excellent antioxygenic property, can be used as antioxidant.
The present invention also provides purposes of the compounds of this invention in agricultural pests are killed.
The compound of the present invention, it is also possible to make insecticide, have to agricultural pests such as mythimna separata, Tetranychus cinnabarinus, Culex pipiens pallens Preferable cytotoxicity.It is therefore preferable that the agricultural pests are mythimna separata, Tetranychus cinnabarinus or Culex pipiens pallens.
The present invention splices principle using bio-active group, heterocyclic compound is introduced into amide compound, it was found that one A little structures are novel, the reactive compound of superior activity or active lead compound, so as to be novel antioxidant and insecticide Preferable basis has been established in initiative.
Embodiment
The present invention provides compound of the structural formula as shown in formula I：
Wherein, R1ForR2For C1-C4 Alkyl；R3For hydrogen or halogen；R4For hydrogen or halogen；X is O or S.
It is preferred that, R1ForR2For C1-C4 alkyl.
It is preferred that, R1ForR2For first Base；R3For hydrogen or halogen；R4For hydrogen or halogen；X is O or S.
Preferably, R1ForR2 For methyl.
Position on phenyl ring can be ortho position, meta or contraposition etc., preferably meta or Contraposition, i.e., preferred structure formula is as shown in formula I -1 or formula I -2：
The following is some currently preferred compounds.
The compound of the present invention, can be obtained, its reaction principle is as follows using conventional preparation method：
The compound of the present invention, with excellent antioxygenic property, can be used as antioxidant.
The compound of the present invention, it is also possible to make insecticide, have to agricultural pests such as mythimna separata, Tetranychus cinnabarinus, Culex pipiens pallens Preferable cytotoxicity.
The embodiment of the present invention is further described with reference to embodiment, not therefore by present invention limit System is among described scope of embodiments.
The synthesis of the compound 1~5 of embodiment 1
1st, the synthetic method of compound 1
(1) 3- aminoacetophenones (0.01mol) are dissolved in after absolute ethyl alcohol (10mL), be added in 50mL three-necked bottles, then NaOH ethanol solution (10%, 5mL) is added to the solution.Under conditions of stirring and ice-water bath, by furfural (0.01mol) Above-mentioned solution is slowly added into the mixture of absolute ethyl alcohol (10mL), controlling reaction temperature is maintained at 0-5 DEG C, and passes through thin layer Silica gel plate (TLC) detects terminal.After the completion of reaction, appropriate distilled water (there are a large amount of solids to separate out) is added into reactant mixture, The pH value of solution is adjusted to about 7 with 10%HCl, the solid of precipitation is filtered and distillation water washing, obtained crude product is used Recrystallized with absolute ethyl alcohol, obtain intermediate.
(2) homemade intermediate (0.005mol) is dissolved in dichloromethane (10mL), be added in 50mL three-necked bottles, then will Triethylamine (3mL) is added in the solution.Under conditions of stirring and ice-water bath, by acetoxy acetyl chloride (0.015mol) and The mixed liquor of dichloromethane (5mL) is slowly instilled in three-necked bottle with constant pressure funnel, and controlling reaction temperature is maintained at 0-5 DEG C, And terminal is detected by thin layer silica gel plate (TLC).After the completion of reaction, washed successively with hydrochloric acid (10%) and sodium hydroxide (10%) Reaction solution is washed, vacuum distillation removes solvent (dichloromethane), obtains crude product, then is recrystallized with absolute ethyl alcohol, that is, obtains product.
Light brown powder solid；IR(KBr)νmax(cm-1):3448,1738,1709,1654,1600,1556,1483, 1384,972,761,728；1H NMR(400MHz,DMSO-d6)δ(ppm):10.35(s,1H),8.26(s,1H),7.95(d,J =1.2Hz, 1H), 7.88 (dd, J1=1.2Hz, J2=1.6Hz, 1H), 7.80 (d, J=8.0Hz, 1H), 7.60 (d, J= 15.2Hz, 1H), 7.53 (t, J=8.0Hz, 1H), 7.47 (d, J=15.6Hz, 1H), 7.13 (d, J=3.2Hz, 1H), 6.72 (dd,J1=1.6Hz, J2=2.0Hz, 1H), 4.69 (s, 2H), 2.15 (s, 3H)；13C NMR(100MHz,DMSO-d6)δ (ppm):188.71(1C),170.55(1C),166.37(1C),151.49(1C),146.81(1C),139.43(1C), 138.51(1C),131.12(1C),129.94(1C),124.12(1C),123.95(1C),119.19(1C),118.83(1C), 117.96(1C),113.67(1C),62.98(1C),20.95(1C)；HRMS(ESI)m/z:Calcd for C17H16NO5[M+H ]+:314.1023,Found:314.1022.
2nd, the synthetic method of compound 2
(1) 3- aminoacetophenones (0.01mol) are dissolved in after absolute ethyl alcohol (10mL), be added in 50mL three-necked bottles, then NaOH ethanol solution (10%, 5mL) is added to the solution.Under conditions of stirring and ice-water bath, by thiophene -2-formaldehyde The mixture of (0.01mol) and absolute ethyl alcohol (10mL) is slowly added into above-mentioned solution, and controlling reaction temperature is maintained at 0-5 DEG C, And terminal is detected by thin layer silica gel plate (TLC).After the completion of reaction, appropriate distilled water is added into reactant mixture (has a large amount of Solid is separated out), the pH value of solution is adjusted to about 7 with 10%HCl, the solid of precipitation is filtered and distillation water washing is used, obtained To crude product recrystallized with absolute ethyl alcohol, obtain intermediate.
(2) homemade intermediate (0.005mol) is dissolved in dichloromethane (10mL), be added in 50mL three-necked bottles, then will Triethylamine (3mL) is added in the solution.Under conditions of stirring and ice-water bath, by acetoxy acetyl chloride (0.015mol) and The mixed liquor of dichloromethane (5mL) is slowly instilled in three-necked bottle with constant pressure funnel, and controlling reaction temperature is maintained at 0-5 DEG C, And terminal is detected by thin layer silica gel plate (TLC).After the completion of reaction, washed successively with hydrochloric acid (10%) and sodium hydroxide (10%) Reaction solution is washed, vacuum distillation removes solvent (dichloromethane), obtains crude product, then is recrystallized with absolute ethyl alcohol, that is, obtains product.
Pale yellow powder shape solid；IR(KBr)νmax(cm-1):3432,3338,1735,1707,1650,1578,1560, 1487,1384,966,797,699；1H NMR(400MHz,DMSO-d6)δ(ppm):10.34 (s, 1H), 8.22 (t, J= 2.0Hz, 1H), 7.95 (d, J=15.2Hz, 1H), 7.91-7.89 (m, 1H), 7.85-7.83 (m, 1H), 7.82 (d, J= 4.8Hz, 1H), 7.71 (d, J=3.6Hz, 1H), 7.54 (t, J=7.6Hz, 1H), 7.48 (d, J=15.2Hz, 1H), 7.23- 7.21(m,1H),4.69(s,2H),2.15(s,3H)；13C NMR(100MHz,DMSO-d6)δ(ppm):188.84(1C), 170.55(1C),166.36(1C),140.12(1C),139.40(1C),138.53(1C),137.50(1C),133.67(1C), 131.01(1C),129.87(1C),129.26(1C),124.22(1C),124.15(1C),120.62(1C),119.21(1C), 62.99(1C),20.95(1C)；HRMS(ESI)m/z:Calcd for C17H16NO4S[M+H]+:330.0795,Found: 330.0790.
3rd, the synthetic method of compound 3
(1) 4- aminoacetophenones (0.01mol) are dissolved in after absolute ethyl alcohol (10mL), be added in 50mL three-necked bottles, then NaOH ethanol solution (10%, 5mL) is added to the solution.Under conditions of stirring and ice-water bath, by furfural (0.01mol) Above-mentioned solution is slowly added into the mixture of absolute ethyl alcohol (10mL), controlling reaction temperature is maintained at 0-5 DEG C, and passes through thin layer Silica gel plate (TLC) detects terminal.After the completion of reaction, appropriate distilled water (there are a large amount of solids to separate out) is added into reactant mixture, The pH value of solution is adjusted to about 7 with 10%HCl, the solid of precipitation is filtered and distillation water washing, obtained crude product is used Recrystallized with absolute ethyl alcohol, obtain intermediate.
(2) homemade intermediate (0.005mol) is dissolved in dichloromethane (10mL), be added in 50mL three-necked bottles, then will Triethylamine (3mL) is added in the solution.Under conditions of stirring and ice-water bath, by acetoxy acetyl chloride (0.015mol) and The mixed liquor of dichloromethane (5mL) is slowly instilled in three-necked bottle with constant pressure funnel, and controlling reaction temperature is maintained at 0-5 DEG C, And terminal is detected by thin layer silica gel plate (TLC).After the completion of reaction, washed successively with hydrochloric acid (10%) and sodium hydroxide (10%) Reaction solution is washed, vacuum distillation removes solvent (dichloromethane), obtains crude product, then is recrystallized with absolute ethyl alcohol, that is, obtains product.
Brown crystal；IR(KBr)νmax(cm-1):3447,3324,1747,1711,1652,1605,1567,1528, 1470,1384,966,820；1H NMR(400MHz,DMSO-d6)δ(ppm):10.49 (s, 1H), 8.08 (d, J=8.8Hz, 2H), 7.92 (d, J=1.6Hz, 1H), 7.75 (d, J=8.8Hz, 2H), 7.55 (s, 2H), 7.10 (d, J=3.2Hz, 1H), 6.69(dd,J1=1.6Hz, J2=2.0Hz, 1H), 4.69 (s, 2H), 2.13 (s, 3H)；13C NMR(100MHz,DMSO-d6)δ (ppm):187.43(1C),170.55(1C),166.60(1C),151.69(1C),146.55(1C),143.27(1C), 132.95(1C),130.48(1C),130.20(2C),119.19(2C),119.05(1C),117.29(1C),113.57(1C), 63.05(1C),20.90(1C)；HRMS(ESI)m/z:Calcd for C17H16NO5[M+H]+:314.1023,Found: 314.1020.
4th, the synthetic method of compound 4
(1) 4- aminoacetophenones (0.01mol) are dissolved in after absolute ethyl alcohol (10mL), be added in 50mL three-necked bottles, then NaOH ethanol solution (10%, 5mL) is added to the solution.Under conditions of stirring and ice-water bath, by thiophene -2-formaldehyde The mixture of (0.01mol) and absolute ethyl alcohol (10mL) is slowly added into above-mentioned solution, and controlling reaction temperature is maintained at 0-5 DEG C, And terminal is detected by thin layer silica gel plate (TLC).After the completion of reaction, appropriate distilled water is added into reactant mixture (has a large amount of Solid is separated out), the pH value of solution is adjusted to about 7 with 10%HCl, the solid of precipitation is filtered and distillation water washing is used, obtained To crude product recrystallized with absolute ethyl alcohol, obtain intermediate.
(2) homemade intermediate (0.005mol) is dissolved in dichloromethane (10mL), be added in 50mL three-necked bottles, then will Triethylamine (3mL) is added in the solution.Under conditions of stirring and ice-water bath, by acetoxy acetyl chloride (0.015mol) and The mixed liquor of dichloromethane (5mL) is slowly instilled in three-necked bottle with constant pressure funnel, and controlling reaction temperature is maintained at 0-5 DEG C, And terminal is detected by thin layer silica gel plate (TLC).After the completion of reaction, washed successively with hydrochloric acid (10%) and sodium hydroxide (10%) Reaction solution is washed, vacuum distillation removes solvent (dichloromethane), obtains crude product, then is recrystallized with absolute ethyl alcohol, that is, obtains product.
Yellow crystals；IR(KBr)νmax(cm-1):3441,1709,1649,1598,1541,1384,958,820；1H NMR (400MHz,DMSO-d6)δ(ppm):10.50 (s, 1H), 8.12 (d, J=8.4Hz, 2H), 7.91 (d, J=15.2Hz, 1H), 7.80 (d, J=5.2Hz, 1H), 7.77 (d, J=8.4Hz, 2H), 7.70 (d, J=3.2Hz, 1H), 7.59 (d, J=15.2Hz, 1H),7.21(dd,J1=3.6Hz, J2=3.6Hz, 1H), 4.71 (s, 2H), 2.15 (s, 3H)；13C NMR(100MHz,DMSO- d6)δ(ppm):187.51(1C),170.51(1C),166.57(1C),143.27(1C),140.30(1C),136.68(1C), 133.10(1C),132.97(1C),130.71(1C),130.25(2C),129.16(1C),120.74(1C),119.20(2C), 63.05(1C),20.90(1C)；HRMS(ESI)m/z:Calcd for C17H16NO4S[M+H]+:330.0795,Found: 330.0788.
5th, the synthetic method of compound 5
(1) 4- aminoacetophenones (0.01mol) are dissolved in after absolute ethyl alcohol (10mL), be added in 50mL three-necked bottles, then NaOH ethanol solution (10%, 5mL) is added to the solution.Under conditions of stirring and ice-water bath, by 3- pyridine carboxaldehydes The mixture of (0.01mol) and absolute ethyl alcohol (10mL) is slowly added into above-mentioned solution, and controlling reaction temperature is maintained at 0-5 DEG C, And terminal is detected by thin layer silica gel plate (TLC).After the completion of reaction, appropriate distilled water is added into reactant mixture (has a large amount of Solid is separated out), the pH value of solution is adjusted to about 7 with 10%HCl, the solid of precipitation is filtered and distillation water washing is used, obtained To crude product recrystallized with absolute ethyl alcohol, obtain intermediate.
(2) homemade intermediate (0.005mol) is dissolved in dichloromethane (10mL), be added in 50mL three-necked bottles, then will Triethylamine (3mL) is added in the solution.Under conditions of stirring and ice-water bath, by acetoxy acetyl chloride (0.015mol) and The mixed liquor of dichloromethane (5mL) is slowly instilled in three-necked bottle with constant pressure funnel, and controlling reaction temperature is maintained at 0-5 DEG C, And terminal is detected by thin layer silica gel plate (TLC).After the completion of reaction, washed successively with hydrochloric acid (10%) and sodium hydroxide (10%) Reaction solution is washed, vacuum distillation removes solvent (dichloromethane), obtains crude product, then is recrystallized with absolute ethyl alcohol, that is, obtains product.
Yellow crystals；IR(KBr)νmax(cm-1):3440,1746,1705,1658,1611,1589,1478,1384,945, 804；1H NMR(400MHz,DMSO-d6)δ(ppm):10.52 (s, 1H), 9.04 (d, J=2.0Hz, 1H), 8.63 (dd, J1= 1.6Hz,J2=1.2Hz, 1H), 8.38-8.36 (m, 1H), 8.21 (d, J=8.8Hz, 2H), 8.11 (d, J=15.6Hz, 1H), 7.80–7.75(m,3H),7.51(dd,J1=4.4Hz, J2=4.8Hz, 1H), 4.72 (s, 2H), 2.15 (s, 3H)；13C NMR (100MHz,DMSO-d6)δ(ppm):187.76(1C),170.55(1C),166.65(1C),151.39(1C),150.80 (1C),143.51(1C),140.49(1C),135.54(1C),132.76(1C),131.07(1C),130.58(2C),124.38 (1C),124.24(1C),119.12(2C),63.04(1C),20.91(1C)；HRMS(ESI)m/z:Calcd for C18H17N2O4[M+H]+:325.1183,Found:325.1183.
The measure of the compounds of this invention insecticidal activity of test example 1
1st, for examination insect
The instar larvae of mythimna separata 3, Tetranychus cinnabarinus is into mite, the instar larvae of Culex pipiens pallens 3, they be it is indoor for many generations raise throughout the year it is quick Feel strain.
2nd, the assay method of mythimna separata
Testing sample is dissolved in dimethyl sulfoxide and certain concentration is diluted to the 0.1% Tween-80 aqueous solution, to be not added with The corresponding solution of testing sample is negative control.Maize leaf is cut into 2 × 4cm segment, taken after soaking 5s in solution to be measured Open, bottom is put into after draining and is covered with the culture dish of filter paper (6cm), access 15 first 3 instar larvaes, then it is 22 to place it in temperature ~24 DEG C, relative humidity is 60%, and light application time is 14:Continue to raise in 10h laboratory, record death condition after 24h, often One experiment in triplicate, and calculates corrected mortality with following equation：
3rd, the assay method of Tetranychus cinnabarinus
Testing sample is dissolved in dimethyl sulfoxide and certain concentration is diluted to the 0.1% Tween-80 aqueous solution, to be not added with The corresponding solution of testing sample is negative control.Gather the big Kidney bean leaf of insect density, carefully choose make health into mite (30~ 50) stay on blade face, taken away after the Kidney bean leaf with worm is immersed into solution 5s to be measured, the training that bottom is covered with filter paper is put into after draining Support in ware (6cm), be placed on temperature for 22~24 DEG C, relative humidity is 60%, and light application time is 14:10h laboratory relaying It is continuous to raise, death condition is recorded after 24h, each experiment in triplicate, and calculates corrected mortality with following equation：
4th, the assay method of Culex pipiens pallens
Using the method for world health organisation recommendations, testing sample is dissolved in dimethyl sulfoxide and with 0.1% Tween-80 water Solution is diluted to certain concentration, to be not added with the corresponding solution of testing sample as negative control.Every kind of solution 1mL is taken, is added respectively Enter into the 118mL wax dixie cups equipped with 99mL distilled water and 20 instar larvaes of Culex pipiens pallens 3, these dixie cups are placed on temperature For 22~24 DEG C, relative humidity is 60%, and light application time is 14:Continue to raise in 10h laboratory, dead feelings are recorded after 24h Condition, each experiment in triplicate, and calculates corrected mortality with following equation：
5th, result of the test
The desinsection of the compounds of this invention the results are shown in Table 1.
Table 1
a：The average value of three repetitions.
It was found from upper table 1, the compounds of this invention has preferable cytotoxicity to mythimna separata, Tetranychus cinnabarinus and Culex pipiens pallens.
The measure of the antioxygenic property of the compounds of this invention of test example 2
1st, instrument and reagent
721B type spectrophotometers, 1,1- diphenyl -2- picryls hydrazine (DPPH), 95% ethanol.
2nd, determination step
(1) preparation of DPPH and sample solution
0.0130 gram of DPPH is accurately weighed with assay balance, is settled to 95% ethanol in 500mL volumetric flasks, obtains concentration For 26mg/L solution；0.0100g testing samples accurately are weighed, is settled to 95% ethanol in 100mL volumetric flasks, obtains concentration For 100mg/L sample solution.
(2) 4mL DPPH solution and 1mL95% ethanol solutions is sequentially added in 10mL conical flasks, stable reaction is mixed Afterwards, using 95% ethanol as reference solution, its absorbance is determined at λ max=518nm, A is designated as0。
(3) 4mL DPPH solution and 1mL solution to be measured is sequentially added in 10mL conical flasks, shakes up, reacts at room temperature After 40min is stable, using 95% ethanol as reference solution, its absorbance is determined at wavelength X max=518nm, A is designated asS.Often One experiment in triplicate, and with following equation calculate antioxidant free radical scavenging activity Y (%)：
3rd, the measurement result of antioxygenic property
Measurement result is shown in Table 2.
Table 2 is when concentration is 100mg/L, clearance rate of the compound to DPPH free radicals
a：The average value of three repetitions.
It was found from upper table 2, the compounds of this invention to the clearance rate of DPPH free radicals all more than 85%, i.e., they have compared with Good antioxygenic property.

Claims (8)

1. compound of the structural formula as shown in formula I：
Wherein, R1ForR2For C1-C4 alkyl； R3For hydrogen or halogen；R4For hydrogen or halogen；X is O or S.
2. compound according to claim 1, it is characterised in that：R1For
3. compound according to claim 1 or 2, it is characterised in that：R2For methyl.
4. the compound according to any one of claims 1 to 3, it is characterised in that structural formula is as shown in formula I -1 or formula I -2：
5. compound according to claim 1, it is characterised in that its structural formula is as follows：
6. application of the compound described in any one of Claims 1 to 5 in antioxidant is prepared.
7. application of the compound in preventing and treating agricultural pests described in any one of Claims 1 to 5.
8. application of the compound in preventing and treating agricultural pests according to right wants 7, it is characterised in that：The agricultural pests are Mythimna separata, Tetranychus cinnabarinus or Culex pipiens pallens.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101402606A (en) * 2008-11-25 2009-04-08 中国农业大学 Nitrogen heterocyclic ring substituted arylpropenone compounds, preparation method and application thereof
CN101792413A (en) * 2010-01-25 2010-08-04 中国农业大学 (E)-1-aryl-5-phenyl-2-alkene-1-pentanone compounds and synthesis and application thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5250532A (en) * 1991-04-11 1993-10-05 Dowelanco 3,4,N-trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their use as insecticides
DE4330105A1 (en) * 1993-09-06 1995-03-09 Bayer Ag Use of ss-hetaryl-ss-oxopropionitriles as pesticides
JP3596032B2 (en) * 1994-07-06 2004-12-02 日産化学工業株式会社 Semicarbazone derivative
GB9910544D0 (en) * 1999-05-08 1999-07-07 Sorex Limited The treatment of pests using certain ethylenically-unsaturated carbonyl compounds
DE10106457A1 (en) * 2001-02-13 2002-08-14 Bayer Ag DELTA · 1 · -pyrrolines
CN101228872B (en) * 2008-02-28 2011-06-15 四川大学 Uses of chalcone synthesis on agricultural chemical
EP2922831B1 (en) * 2012-11-21 2017-10-18 Syngenta Participations AG Pesticidal compounds based on arylthiosulfonamide derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101402606A (en) * 2008-11-25 2009-04-08 中国农业大学 Nitrogen heterocyclic ring substituted arylpropenone compounds, preparation method and application thereof
CN101792413A (en) * 2010-01-25 2010-08-04 中国农业大学 (E)-1-aryl-5-phenyl-2-alkene-1-pentanone compounds and synthesis and application thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
MOHAMED RAMADAN EL SAYED ALY等: "Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 *
张恩等: "吡啶查尔酮衍生物的合成及抑制耐甲氧西林金黄色葡萄球菌活性评价", 《有机化学》 *

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